KR20220094124A - Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device including the same. The present invention can provide an organic electroluminescent device with improved driving voltage, luminous efficiency and/or lifetime by including the organic electroluminescent compound according to the present application as a single host material or a specific combination of compounds according to the present application as a plurality of host materials.

Description

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

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

Eastman Kodak's Tang et al. first developed a TPD/Alq3 double-layer low-molecular 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. In many application fields such as TV and lighting, the OLED lifespan is facing the problem of insufficient, and high efficiency of OLED is still required. In general, the higher the luminance of the OLED, the shorter the lifespan of the OLED. Accordingly, OLEDs having high luminous efficiency and/or long lifespan are required for long-term use of the display and high resolution.

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.

Meanwhile, Korean Patent Application Laid-Open No. 2010-0133467 discloses a fluorene derivative compound, but does not specifically disclose a specific compound or a specific combination of host materials claimed in the present application. In addition, there is a need to develop a light-emitting material having improved performance, such as a low driving voltage, high luminous efficiency, and/or improved lifetime characteristics, compared to the compounds disclosed in the above patent documents.

Korean Patent Publication No. 2010-0133467 (published on December 21, 2010)

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

As a result of intensive research to solve the above technical problem, the present inventors have found that the organic electroluminescent compound represented by the following Chemical Formula 4 achieves the above object and completed the present invention. In addition, the present inventors have described a plurality of host materials, including a first host material including a compound represented by the following Chemical Formula 1, and a second host material including a compound represented by the following Chemical Formula 2 or Chemical Formula 3, as described above. The present invention was completed by finding that one object was achieved.

[Formula 1]

In Formula 1,

Ring A and Ring B are each independently a substituted or unsubstituted (C6-C30) arene, or a substituted or unsubstituted (3-30 membered) heteroarene;

L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

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

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

[Formula 2]

In Formula 2,

X ₂₁ and Y ₂₁ are each independently -N=, -NR ₃₁ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, and X ₂₁ and Y ₂₁ the other is -NR ₃₁ -, -O-, or -S-;

R ₂₁ and R ₃₁ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂₂ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -L-NR ₁ R ₂ , or -L ₂₁ -Ar ₂₁ ; may be linked with adjacent substituents to form a ring; provided that at least one of R ₂₂ to R ₂₉ is -L ₂₁ -Ar ₂₁ ;

L ₂₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₂₁ is each independently a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -NR ₃₂ R ₃₃ ;

R ₃₂ and R ₃₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted a fused ring group of a cyclic (3-30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;

L is a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, a substituted or unsubstituted divalent (C2-C30) aliphatic hydrocarbon group, or a fused ring group of a substituted or unsubstituted divalent (C3-C30) aliphatic ring and (C6-C30) aromatic ring;

R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl.

[Formula 3]

In Formula 3,

A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl; ;

one of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are linked to each other to form a single bond;

X ₁₅ to X ₂₂ that does not form a single bond, X ₁₁ to X ₁₄ , and X ₂₃ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted It may be a cyclic (3-30 membered) heteroaryl, or may be linked to an adjacent substituent to form a ring.

[Formula 4]

In Formula 4,

A ring and B ring are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring;

L ₁ is a single bond;

L ₂ is a single bond, or a substituted or unsubstituted (C6-C30)arylene;

Ar is substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;

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

인 치환기로 치환된 헤테로아릴인 경우는 제외하고, However, HAr

Except for the case of heteroaryl substituted with a phosphorus substituent,

wherein R ₃₀₀ is (C1-C30)alkyl, or (C6-C30)aryl;

The * represents the bonding position of the substituent,

The following compounds are also excluded.

The organic electroluminescent compound according to the present disclosure exhibits suitable performance for use in organic electroluminescent devices. In addition, by including the compound according to the present application as a single host material or a specific combination of the compound according to the present application as a plurality of host materials, a lower driving voltage, higher luminous efficiency and/or superior lifetime compared to a conventional organic electroluminescent device An organic electroluminescent device having characteristics is provided, and 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 transport material, an electron injection material, or the like.

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

As used herein, "(C1-C30)alkyl" means a straight-chain or branched chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein it is preferably 1 to 10 carbon atoms, and 1 to 6 carbon atoms. more preferably. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl and the like. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, preferably O, S and cycloalkyl containing one or more heteroatoms selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. As used herein, “(C6-C30)aryl”, “(C6-C30)arylene” or “(C6-C30)arene” refers to a monocyclic or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. meaning, and may be partially saturated. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, di Benzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, sp Robbiefluorenyl, spiro[fluorene-benzofluoren]yl, spiro[cyclopenten-fluoren]yl, spiro[dihydroinden-fluoren]yl, azulenyl, tetramethyldihydrophenanthrenyl, etc. have. Specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3 -Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [a] fluorenyl, benzo [b] fluorenyl, benzo [c] fluorenyl, dibenzo fluorenyl, 2- Biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p- Terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9- fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p- tert -butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4" -tert -butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9, 9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11, 11-dimethyl-4-benzo [a] fluorenyl, 11,11-dimethyl-5-benzo [a] fluorenyl, 11,11-dimethyl-6-benzo [a] fluorenyl, 11,11- Dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl- 10-benzo [a] fluorenyl, 11,11-dimethyl-1-benzo [b ] fluorenyl, 11,11-dimethyl-2-benzo [b] fluorenyl, 11,11-dimethyl-3-benzo [b] fluorenyl, 11,11-dimethyl-4-benzo [b] flu Orenyl, 11,11-dimethyl-5-benzo [b] fluorenyl, 11,11-dimethyl-6-benzo [b] fluorenyl, 11,11-dimethyl-7-benzo [b] fluorenyl , 11,11-dimethyl-8-benzo [b] fluorenyl, 11,11-dimethyl-9-benzo [b] fluorenyl, 11,11-dimethyl-10-benzo [b] fluorenyl, 11 , 11-dimethyl-1-benzo [c] fluorenyl, 11,11-dimethyl-2-benzo [c] fluorenyl, 11,11-dimethyl-3-benzo [c] fluorenyl, 11,11 -Dimethyl-4-benzo [c] fluorenyl, 11,11-dimethyl-5-benzo [c] fluorenyl, 11,11-dimethyl-6-benzo [c] fluorenyl, 11,11-dimethyl -7-benzo [c] fluorenyl, 11,11-dimethyl-8-benzo [c] fluorenyl, 11,11-dimethyl-9-benzo [c] fluorenyl, 11,11-dimethyl-10 -benzo [c] fluorenyl, 11,11-diphenyl-1-benzo [a] fluorenyl, 11,11-diphenyl-2-benzo [a] fluorenyl, 11,11-diphenyl- 3-benzo [a] fluorenyl, 11,11-diphenyl-4-benzo [a] fluorenyl, 11,11-diphenyl-5-benzo [a] fluorenyl, 11,11-diphenyl -6-benzo [a] fluorenyl, 11,11-diphenyl-7-benzo [a] fluorenyl, 11,11-diphenyl-8-benzo [a] fluorenyl, 11,11-di Phenyl-9-benzo [a] fluorenyl, 11,11-diphenyl-10-benzo [a] fluorenyl, 11,11-diphenyl-1-benzo [b] fluorenyl, 11,11- Diphenyl-2-benzo [b] fluorenyl, 11,11-diphenyl-3-benzo [b] fluorenyl, 11,11-diphenyl-4-benzo [b] fluorenyl, 11,11 -diphenyl-5-benzo [b] fluorenyl, 11,11-diphenyl-6-benzo [b] fluorenyl, 11,11-diphenyl-7-benzo [b] fluorenyl, 11, 11-diphenyl-8-benzo [b] fluorenyl, 11,11-diphenyl-9-benzo [b] fluorenyl, 11,11-diphenyl-10-benzo [b] fluorenyl, 11 , 11-diphenyl-1-benzo [c] fluorenyl, 11,11-diphenyl-2-benzo [c] fluorenyl, 11,1 1-diphenyl-3-benzo [c] fluorenyl, 11,11-diphenyl-4-benzo [c] fluorenyl, 11,11-diphenyl-5-benzo [c] fluorenyl, 11 , 11-diphenyl-6-benzo [c] fluorenyl, 11,11-diphenyl-7-benzo [c] fluorenyl, 11,11-diphenyl-8-benzo [c] fluorenyl, 11,11-diphenyl-9-benzo [c] fluorenyl, 11,11-diphenyl-10-benzo [c] fluorenyl, 9,9,10,10-tetramethyl-9,10-di Hydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro- 3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, and the like.

As used herein, "(3-30 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, di Benzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphtho Furopyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl , benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, Benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, di Benzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazole phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidi and fused ring heteroaryls such as nyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imi Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1 -isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-qui Nolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8- Isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7 -yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7 -Phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-arc Lidinyl, 2-oxazolyl, 4-oxa Zolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrole-3- Yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methyl Pyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2 -Methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -Butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzo Thiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl , 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuran yl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzo Furanyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]- Benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b] -benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b ]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3- b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1 -b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2, 1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2 ,1-b]- Benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b] -benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b ]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2- b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3 -b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2, 3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2 ,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[2,1-b]-benzothiophenyl, 5-naphtho-[ 2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho- [2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro [3,2-d] pyrimidinyl, 6-benzofuro [3,2-d] pyrimidinyl, 7-benzofuro [3,2-d] pyrimidinyl, 8-benzofuro [3,2- d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl , 7-benzothio [3,2-d] pyrimidinyl, 8-benzothio [3,2-d] pyrimidinyl, 9-benzothio [3,2-d] pyrimidinyl, 2-benzofuro [3,2-d] pyrazinyl, 6-benzofuro [3,2-d] pyrazinyl, 7-benzofuro [3,2-d] pyrazinyl, 8-benzofuro [3,2-d] pyra Zinyl, 9-benzofuro [3,2-d] pyrazinyl, 2-benzothio [3,2-d] pyrazinyl, 6-benzothio [3,2-d] pyrazinyl, 7-benzothio [3 ,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluoro Renyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2 -dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. are mentioned. As used herein, “halogen” includes F, Cl, Br and I atoms.

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

In the description of "substituted or unsubstituted" as used herein, 'substitution' means that a hydrogen atom in one functional group is replaced by another atom or another functional group (ie, a substituent), and two or more of the substituents are substituted with a connected group It also includes being For example, "a substituent to which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as one heteroaryl substituent or two heteroaryl substituents connected. As used herein, substituted alkyl, substituted alkenyl, substituted aryl, substituted arene, substituted arylene, substituted heteroaryl, substituted heteroarene, substituted heteroarylene, substituted dibenzofuranyl, substituted Dibenzothiophenyl, substituted carbazolyl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted aliphatic ring and The substituents of the fused ring group of the aromatic ring, the substituted divalent aliphatic hydrocarbon group, or the fused ring group of the substituted divalent aliphatic ring and the aromatic ring are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy , (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3- C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, substituted with one or more (C6-C30)aryl or unsubstituted (3-30 membered)heteroaryl, (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30) unsubstituted or substituted with one or more (3-30 membered)heteroaryl )Arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C3-C30) aliphatic ring and (C6-C30) aromatic fused cyclic groups of rings, amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C2-C30)alkenylamino, (C1-C30)alkyl(C2-C30)alkenylamino, Substituted or unsubstituted mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di- (3-30 membered)heteroarylamino, (C1-C30) C30) alkyl (3-30 membered) heteroarylamino, (C2-C30) alkenyl (C6-C30) arylamino, (C2-C30) alkenyl (3-30 membered) heteroarylamino, (C6-C30) Aryl (3-30 membered) heteroarylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6- At least one selected from the group consisting of C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl, which may be further substituted with deuterium. According to an aspect of the present application, the substituents are each independently deuterium, (C1-C20)alkyl, (5-25 membered) heteroaryl unsubstituted or substituted with one or more (C6-C25)aryl, one or more (5- 25-membered) at least one selected from the group consisting of (C6-C25)aryl unsubstituted or substituted with heteroaryl, and tri(C6-C25)arylsilyl, which may be further substituted with deuterium. According to another aspect of the present application, the substituents are each independently deuterium, (C1-C10)alkyl, (5-25 membered) heteroaryl unsubstituted or substituted with one or more (C6-C18)aryl, one or more (5 At least one selected from the group consisting of (C6-C20) aryl unsubstituted or substituted with -20 membered) heteroaryl, and tri (C6-C18) arylsilyl, which may be further substituted with deuterium. For example, the substituents are each independently deuterium, methyl, phenyl unsubstituted or substituted with dibenzofuranyl, naphthyl unsubstituted or substituted with dibenzofuranyl, biphenyl unsubstituted or substituted with dibenzofuranyl, Phenanthrenyl, chrysenyl, triphenylenyl, phenyl-substituted or unsubstituted pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl-substituted carbazolyl, dibenzocarbazolyl, phenyl-substituted phenanthrooxa It may be at least one selected from the group consisting of zolyl, 23-membered heteroaryl, and triphenylsilyl, and these may be further substituted with deuterium.

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

As used herein, heteroaryl, heteroarylene, and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted (C1-C30 ) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino , substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino One or more may be combined.

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

In Formula 1, ring A and ring B are each independently a substituted or unsubstituted (C6-C30) arene, or a substituted or unsubstituted (3-30 membered) heteroarene. According to an aspect of the present application, ring A and ring B are each independently a substituted or unsubstituted (C6-C25) arene, or a substituted or unsubstituted (5-25 membered) heteroarene. According to another embodiment of the present application, the A ring and the B ring are each independently an unsubstituted (C6-C18) arene or an unsubstituted (5-20 membered) heteroarene. For example, the A ring and the B ring may each independently be a benzene ring, a naphthalene ring, a phenanthrene ring, or a pyridine ring.

In Formula 1, L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene. According to one aspect of the present application, L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5-25 membered)heteroarylene. According to another aspect of the present application, L ₁ and L ₂ are each independently single bond, unsubstituted (C6-C18)arylene, or unsubstituted (5-20 membered)heteroarylene. For example, L ₁ and L ₂ are each independently It may be a single bond or phenylene or the like.

In Formula 1, Ar 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, Ar is a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, Ar is (C6-C18)aryl unsubstituted or substituted with one or more of deuterium and cyano; or (5-20 membered)heteroaryl unsubstituted or substituted with one or more of deuterium, cyano and (C6-C18)aryl. For example, Ar may be phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl substituted with phenyl, which may be further substituted with one or more of deuterium and cyano.

In Formula 1, HAr is a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl. According to one aspect of the present application, HAr is a substituted or unsubstituted nitrogen-containing (5-18 membered)heteroaryl. According to another aspect of the present application, HAr is a substituted nitrogen-containing (5-18 membered)heteroaryl. Specifically, HAr is substituted or unsubstituted, pyridyl, triazinyl, pyrimidinyl, quinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, benzofuropyrimidinyl, carbazolyl , dibenzothiophenyl, benzothiophenyl, dibenzofuranyl, benzofuranyl, naphthyridinyl, benzonaphthofuranyl or benzonaphthothiophenyl. For example, HAr can be a substituted triazinyl, or a substituted pyrimidinyl, and the like; The substituents of the substituted triazinyl and the substituted pyrimidinyl are each independently phenyl unsubstituted or substituted with dibenzofuranyl; naphthyl unsubstituted or substituted with dibenzofuranyl; biphenyl unsubstituted or substituted with dibenzofuranyl; fluorenyl substituted with one or more of methyl, phenyl and naphthyl; phenanthrenyl; chrysenyl; dibenzofuranyl; dibenzothiophenyl; phenyl-substituted phenanthrooxazolyl; phenyl-substituted carbazolyl; dibenzocarbazolyl; and at least one selected from the group consisting of nitrogen-containing 23-membered heteroaryl, preferably any two, and the substituent may be further substituted with at least one of deuterium and cyano.

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

In the above formula, R ₁₀₁ to R ₁₅₀ 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 substituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl (C6 -C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted (C3-C30) is a fused ring group of an aliphatic ring of (C6-C30) and an aromatic ring of (C6-C30), or -L-NR ₁ R ₂ . For example, R ₁₀₁ to R ₁₅₀ may be hydrogen.

In the above formula, HAr, Ar, L ₁ , L ₂ , L, R ₁ and R ₂ are as defined in Formula 1.

In Formula 2, X ₂₁ and Y ₂₁ are each independently -N=, -NR ₃₁ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=; The other of X ₂₁ and Y ₂₁ is -NR ₃₁ -, -O-, or -S-. According to an aspect of the present application, X ₂₁ and Y ₂₁ are each independently -N=, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, X ₂₁ and Another one of Y ₂₁ is -O- or -S-.

and R ₃₁ is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl.

In Formula 2, R ₂₁ 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 ₂₁ is a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another embodiment of the present application, R ₂₁ is unsubstituted (C6-C18)aryl, or unsubstituted (5-20 membered)heteroaryl. For example, R ₂₁ may be phenyl, naphthyl, biphenyl, pyridyl, quinolyl, or isoquinolyl.

In Formula 2, R ₂₂ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -L-NR ₁ R ₂ , or -L ₂₁ -Ar ₂₁ ; may be linked with adjacent substituents to form a ring; However, at least one of R ₂₂ to R ₂₉ is -L ₂₁ -Ar ₂₁ . According to an aspect of the present application, R ₂₂ to R ₂₉ are each independently hydrogen, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 membered) heteroaryl, or -L ₂₁ - Ar ₂₁ ; However, at least one of R ₂₂ to R ₂₉ is -L ₂₁ -Ar ₂₁ . According to another aspect of the present application, R ₂₂ to R ₂₉ are each independently hydrogen or -L ₂₁ -Ar ₂₁ ; However, at least one of R ₂₂ to R ₂₉ is -L ₂₁ -Ar ₂₁ . For example, any one of R ₂₂ to R ₂₉ may be -L ₂₁ -Ar ₂₁ , and the rest may be hydrogen.

Each of L ₂₁ is 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, each L ₂₁ is independently a single bond, or a substituted or unsubstituted (C6-C25)arylene. According to another aspect of the present application, each L ₂₁ is independently a single bond, or an unsubstituted (C6-C18)arylene. For example, L ₂₁ may each independently be a single bond, phenylene, or naphthylene.

Ar ₂₁ is each independently a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted cyclic (3-30 membered) heteroaryl, or -NR ₃₂ R ₃₃ . According to an aspect of the present application, Ar ₂₁ is each independently a fused ring group of a substituted or unsubstituted (C3-C25) aliphatic ring and a (C6-C18) aromatic ring, a substituted or unsubstituted (C6-C30) )aryl, substituted or unsubstituted (5-25 membered)heteroaryl, or -NR ₃₂ R ₃₃ . According to another aspect of the present application, Ar ₂₁ is each independently a fused ring group of an unsubstituted (C3-C18) aliphatic ring and a (C6-C18) aromatic ring, substituted or unsubstituted with (C1-C10)alkyl cyclic (C6-C30)aryl, or -NR ₃₂ R ₃₃ .

R ₃₂ and R ₃₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or It is a fused ring group of an unsubstituted (3-30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring. According to an aspect of the present application, R ₃₂ and R ₃₃ are each independently a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, R ₃₂ and R ₃₃ are each independently, (C6-C25)aryl unsubstituted or substituted with (C1-C6)alkyl, or (C6-C18)aryl unsubstituted or substituted (5-20 won) Heteroaryl. For example, R ₃₂ and R ₃₃ are each independently phenyl, naphthyl, biphenyl, dimethyl fluorenyl, diphenylfluorenyl, phenanthrenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl , terphenyl, dibenzofuranyl unsubstituted or substituted with phenyl, dibenzothiophenyl unsubstituted or substituted with phenyl, or benzonaphthofuranyl.

L is a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, a substituted or unsubstituted divalent (C2-C30) aliphatic hydrocarbon group, or a fused ring group of a substituted or unsubstituted divalent (C3-C30) aliphatic ring and (C6-C30) aromatic ring.

wherein R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl.

Specifically, Ar ₂₁ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl , substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzo[c]phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentain-fluoren]yl, substituted or unsubstituted spiro[dihydroinden-fluoren]yl, substituted or unsubstituted spiro[benzo fluorene-fluoren]yl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, or substituted or unsubstituted benzonaphthofuranyl; Phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, dimethylfluorenyl, diphenyl At least selected from the group consisting of fluorenyl, dimethylbenzofluorenyl, phenanthrenyl, dibenzothiophenyl substituted or unsubstituted with phenyl, benzonaphthofuranyl, and dibenzofuranyl substituted or unsubstituted with phenyl It may be amino substituted with one substituent.

According to an aspect of the present application, Chemical Formula 2 may be represented by any one of the following Chemical Formulas.

In the above formula, X ₂₁ , Y ₂₁ , L ₂₁ , Ar ₂₁ , and R ₂₁ to R ₂₉ are as defined in Formula 2.

In Formula 3, A ₁ and A ₂ are each independently a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted cyclic carbazolyl. According to an aspect of the present application, A ₁ and A ₂ are each independently a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl. According to another aspect of the present application, A ₁ and A ₂ are each independently deuterium, (C1-C6)alkyl, (C6-C25)aryl, (5-20 membered)heteroaryl and tri(C6-C18)arylsilyl one or more of substituted or unsubstituted (C6-C25)aryl; dibenzofuranyl unsubstituted or substituted with one or more of deuterium and (C6-C18)aryl; dibenzothiophenyl unsubstituted or substituted with one or more of deuterium and (C6-C18)aryl; or carbazolyl unsubstituted or substituted with one or more of deuterium and (C6-C18)aryl. For example, A ₁ and A ₂ are each independently deuterium, methyl, phenyl unsubstituted or substituted with pyridyl, dibenzofuranyl, dibenzothiophenyl, or triphenylsilyl; naphthyl; biphenyl; phenylnaphthyl; naphthylphenyl; terphenyl; triphenylenyl; phenyl substituted with triphenylenyl; dimethyl fluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; phenyl-substituted or unsubstituted dibenzofuranyl; phenyl-substituted or unsubstituted dibenzothiophenyl; or carbazolyl unsubstituted or substituted with phenyl or naphthyl, which may be further substituted with deuterium.

In Formula 3, one of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are connected to each other to form a single bond. X ₁₅ to X ₂₂ that does not form a single bond, X ₁₁ to X ₁₄ , and X ₂₃ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted It may be a cyclic (3-30 membered) heteroaryl, or may be linked to an adjacent substituent to form a ring. According to an aspect of the present application, one that does not form a single bond among X ₁₅ to X ₂₂ , X ₁₁ to X ₁₄ , and X ₂₃ to X ₂₆ are each independently hydrogen, deuterium, or unsubstituted (5) -20 membered) heteroaryl, or may be linked with an adjacent substituent to form a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. For example, those that do not form a single bond among X ₁₅ to X ₂₂ , X ₁₁ to X ₁₄ , and X ₂₃ to X ₂₆ are each independently hydrogen; heavy hydrogen; dibenzothiophenyl unsubstituted or substituted with deuterium; Alternatively, it may be dibenzofuranyl substituted or unsubstituted with deuterium, or may be connected to an adjacent substituent to form a benzene ring substituted or unsubstituted with deuterium.

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

In the above compounds, D means deuterium, and n means the number of deuterium.

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

In the above compounds, Dn means that n hydrogens are substituted with deuterium, n is an integer of 1 or more, and the number of hydrogens in each compound is set as the upper limit. n is preferably an integer of 4 or more, more preferably an integer of 8 or more. When deuterated to a number greater than or equal to the lower limit, the bond dissociation energy according to deuteration increases, thereby increasing the stability of the compound, and when the compound is used in an organic electroluminescent device, improved lifespan characteristics may be exhibited.

At least one of the compounds C-1 to C-222 and at least one of the compounds H-1 to H-220 and H2-1 to H2-178 may be combined to be used in an organic electroluminescent device.

In addition, the present application provides an organic electroluminescent compound represented by the following formula (4).

[Formula 4]

In Formula 4,

A ring and B ring are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring;

L ₁ is a single bond;

L ₂ is a single bond, or a substituted or unsubstituted (C6-C30)arylene;

Ar is substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;

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

인 치환기로 치환된 헤테로아릴인 경우는 제외하고, However, HAr

Except for the case of heteroaryl substituted with a phosphorus substituent,

wherein R ₃₀₀ is (C1-C30)alkyl, or (C6-C30)aryl;

The * represents the bonding position of the substituent,

The following compounds are also excluded.

According to one aspect of the present application, in Formula 4, ring A and ring B are each independently an unsubstituted benzene ring, an unsubstituted naphthalene ring, or an unsubstituted phenanthrene ring.

According to an aspect of the present application, in Formula 4, L ₁ and L ₂ are a single bond.

According to an aspect of the present application, in Formula 4, Ar is unsubstituted (C6-C18)aryl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, or phenyl-substituted carbazolyl, (C6-C18)aryl may be, for example, phenyl, naphthyl, or biphenyl.

According to an aspect of the present application, in Formula 4, HAr is a substituted nitrogen-containing (5-10 membered) heteroaryl. For example, HAr may be a substituted triazinyl, and the substituent of the substituted triazinyl is phenyl unsubstituted or substituted with dibenzofuranyl, naphthyl unsubstituted or substituted with dibenzofuranyl, dibenzofura Biphenyl substituted or unsubstituted with nyl, phenanthrenyl, chrysenyl, dibenzofuranyl, dibenzothiophenyl, phenanthrooxazolyl substituted with phenyl, carbazolyl substituted with phenyl, dibenzocarbazolyl, and nitrogen It may be at least one selected from the group consisting of containing 23-membered heteroaryl, preferably any two.

The compound represented by Formula 4 may be at least one selected from the group consisting of compounds C-1 to C-145, C-156 to C-161, and C-195 to C-222, but are limited thereto not.

Each of the compounds represented by Formula 1 or 4 according to the present application may be prepared by a synthetic method known to those skilled in the art. For example, the compound represented by Formula 1 or 4 may be prepared with reference to the following reaction scheme, but is not limited thereto. The compound represented by Formula 2 may be prepared with reference to a synthesis method known to those skilled in the art, and in particular, a synthesis method disclosed in a number of patent documents may be used. For example, it may be synthesized with reference to the method disclosed in Korean Patent Application Laid-Open No. 2017-0022865 (published on March 2, 2017), but is not limited thereto.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, A ring, B ring, L ₁ , L ₂ , Ar, and HAr are as defined in Formula 1 or 4.

Although exemplary synthesis examples of the compounds represented by Formula 1 or 4 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 , 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 above reaction proceeds even if other substituents defined in Formula 1 or 4 are bound in addition to the substituents specified in the examples.

The present application is a positive electrode; cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer includes a plurality of types of host materials according to the present disclosure, to provide an organic electroluminescent device. The first host material and the second host material of the present disclosure may be included in one light emitting layer, or may be included in each other light emitting layer among the plurality of light emitting layers. In the plurality of host materials of the present application, the compound represented by Formula 1 and the compound represented by Formula 2 are in a ratio of about 1:99 to about 99:1, preferably in a ratio of about 10:90 to about 90:10. , More preferably, it may be included in a ratio of about 30:70 to about 70:30. In addition, the compound represented by Formula 1 and the compound represented by Formula 2 in a desired ratio are put in a shaker and mixed, put in a glass tube, melted by heating, and then collected, or dissolved in a solvent, etc. can be combined.

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. As a dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants may be used, and a phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but may be a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt). , optionally, it may be an ortho-metalation complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and in some cases more preferably, ortho-metalated iridium complex compounds.

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

[Formula 101]

In Formula 101,

L is any one selected from the following structures 1 to 3;

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; Adjacent substituents may be linked to each other to form a ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted quinoline together with pyridine unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

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

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

s is an integer from 1 to 3.

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

In addition, the present application provides an organic electroluminescent material including the organic electroluminescent compound of Formula 4, and an organic electroluminescent device including the material. The material may be made of the organic electroluminescent compound of the present application alone, or may further include conventional materials included in the organic electroluminescent material.

The organic electroluminescent compound of Formula 4 of the present application is an emission layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer (interlayer), a hole blocking layer and electrons It may be included in at least one layer of the blocking layer, and in some cases, preferably, at least one of a light emitting layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer can be included in When used in the light emitting layer, the organic electroluminescent compound of Formula 4 of the present application may be included as a host material. If necessary, the organic electroluminescent compound herein can be used as a co-host material.

The organic electroluminescent device according to the present application includes an anode; cathode; and one or more organic material layers interposed between the anode and the cathode. The organic layer includes a light emitting layer, and is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. It may further include one or more floors. Each of the above layers may further consist of several layers.

Each of the anode and the cathode may be formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. Depending on the type of material forming the anode and the cathode, the organic electroluminescent device may be a top emission type, a bottom emission type, or a double side emission type. Also, the hole injection layer may be further doped with a P-dopant, and the electron injection layer may be further doped with an n-dopant.

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

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

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

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

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

An electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. In the electron buffer layer, a plurality of layers may be used for the purpose of controlling electron injection and improving interfacial properties between the light emitting layer and the electron injection layer, and two compounds may be used for each layer at the same time. A plurality of layers may be used for the hole blocking layer or the electron transport layer, and a plurality of compounds may be used for each layer.

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

Further, in the organic electroluminescent device of the present application, it is also preferable to arrange a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant on at least one surface of a pair of electrodes. In this way, since the electron transport compound is reduced to an anion, it is easy to inject and transfer electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to a cation, it is easy to inject and transport holes from the mixing region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using the reducing dopant layer as a charge generating layer, it is possible to manufacture an organic electroluminescent device emitting white light having two or more light emitting layers.

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

Formation of each layer of the organic electroluminescent device of the present application is a dry film deposition method such as vacuum deposition, sputtering, plasma, ion plating, inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. Any one of the wet film forming methods of When the first host compound and the second host compound of the present application are formed into a film, a co-deposition or mixed vapor deposition is performed.

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

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

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

[Synthesis Example 1] Preparation of compound C-6

compound 1-1 synthesis of

9H-fluoren-9-one (10 g, 55 mmol), p-toluenesulfonyl hydrazide (15.5 g, 83 mmol), and 550 mL of toluene were added and dissolved in a flask, followed by stirring at 80° C. for 2 hours. . Thereafter, phenylboronic acid (10.1 g, 83 mmol) and potassium carbonate (15.3 g, 110 mmol) were added, and the mixture was refluxed at 110° C. for 5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain Compound 1-1 (9.7 g, Yield: 72 %).

compound C-6 synthesis of

Compound 1-1 (5.0 g, 20.6 mmol) and 200 mL of tetrahydrofuran (THF) were added and dissolved in a flask, and then 2.5M n-BuLi in hexane (10.7 mL, 26.8 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. did. After 2 hours, 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (9.6 g, 26.8 mmol) was added and at room temperature for 3 hours stirred. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-6 (8 g, yield: 69 %).

[Synthesis Example 2] Preparation of compound C-5

compound 2-1 synthesis of

Compound 1-1 (4.7 g, 19 mmol) and 190 mL of THF were dissolved in a flask, and then 2.5M n-BuLi in hexane (10 mL, 25 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. After 2 hours, 2,4-dichloro-6-phenyl-1,3,5-triazine (5.7 g, 25 mmol) was added and stirred at room temperature for 3 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound 2-1 (4.7 g, yield: 56 %).

compound C-5 synthesis of

In a flask, compound 2-1 (4.2 g, 9.7 mmol), 2-(chrysen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.1 g, 11.6 mmol), tetrakis (triphenylphosphine) palladium (0) (0.56 g, 0.48 mmol), potassium carbonate (3.4 g, 24 mmol), toluene 48 mL, ethanol 12 mL, and water 12 mL were added and dissolved. It was refluxed for 2.5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-5 (2.5 g, yield: 41 %).

[Synthesis Example 3] Preparation of compound C-145

Compound 2-1 (4.6 g, 11 mmol), 2-(5-(dibenzo[b,d]furan-1-yl)naphthalen-1-yl)-4,4,5,5-tetramethyl in a flask -1,3,2-dioxaborolane (5.0 g, 12 mmol), tetrakis (triphenylphosphine) palladium (0) (0.62 g, 0.5 mmol), potassium carbonate (3.7 g, 27 mmol), toluene 56 mL, 14 mL of ethanol, and 14 mL of water were added and dissolved, followed by refluxing for 3.5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-145 (2.6 g, yield: 35%).

[Synthesis Example 4] Preparation of compound C-26

compound 4-1 synthesis of

Compound 1-1 (15 g, 62 mmol) and 800 mL of THF were dissolved in a flask, and then 2.5M n-BuLi in hexane (32 mL, 80 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. After 2 hours, 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (22.2 g, 80 mmol) was added and stirred at room temperature for 18 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound 4-1 (7.0 g, yield: 23 %).

compound C-26 synthesis of

In a flask, compound 4-1 (3.0 g, 6.2 mmol), dibenzofuran-1-boronic acid (1.5 g, 6.8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.36 g, 0.31 mmol), Potassium carbonate (2.1 g, 15 mmol), toluene 32 mL, ethanol 8 mL, and water 8 mL were added and dissolved, followed by refluxing for 2.5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-26 (2.0 g, yield: 52 %).

[Synthesis Example 5] Preparation of compound C-101

compound 5-1 synthesis of

9H-fluoren-9-one (10 g, 55 mmol), p-toluenesulfonyl hydrazide (15.5 g, 83 mmol), and 550 mL of toluene were added and dissolved in a flask, followed by stirring at 80° C. for 2 hours. . Thereafter, dibenzofuran-1-boronic acid (17.6 g, 83 mmol) and potassium carbonate (15.3 g, 110 mmol) were added and refluxed at 110° C. for 5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound 5-1 (7 g, yield: 38 %).

compound C-101 synthesis of

Compound 5-1 (7.5 g, 20.6 mmol) and 220 mL of THF were dissolved in a flask, and then 2.5M n-BuLi in hexane (11.6 mL, 29 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. After 2 hours, 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29 mmol) was added and stirred at room temperature for 3 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-101 (7.9 g, yield: 62 %).

[Synthesis Example 6] Preparation of compound C-66

compound 6-1 synthesis of

9H-fluoren-9-one (10 g, 55 mmol), p-toluenesulfonyl hydrazide (15.5 g, 83 mmol), and 550 mL of toluene were added and dissolved in a flask, followed by stirring at 80° C. for 2 hours. . After that, naphthalen-2-ylboronic acid (14 g, 83 mmol) and potassium carbonate (15.3 g, 110 mmol) were added and refluxed at 110° C. for 3 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound 6-1 (9.0 g, yield: 56 %).

compound C-66 synthesis of

Compound 6-1 (4.0 g, 13.7 mmol), and 137 mL of THF were dissolved in a flask, and then 2.5M n-BuLi in hexane (7.1 mL, 17.7 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. After 2 hours, 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (6.4 g, 17.7 mmol) was added and at room temperature for 3 hours stirred. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-66 (1.8 g, yield: 21 %).

[Synthesis Example 7] Preparation of compound C-161

In a flask, compound 2-1 (3.0 g, 7 mmol), 2-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenanthro [ 3,4-d]oxazole (2.9 g, 7 mmol), tetrakis(triphenylphosphine)palladium(0) (0.4 g, 0.3 mmol), potassium carbonate (2.4 g, 17 mmol), toluene 34 mL, 8.5 mL of ethanol and 8.5 mL of water were added thereto to dissolve, and then refluxed for 2.5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-161 (3.0 g, yield: 53 %).

[Synthesis Example 8] Preparation of compound C-151

In a flask, 2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine (10 g, 28 mmol), 4,4,5,5 -tetramethyl-2-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,2-dioxaborolane (15.0 g, 33 mmol), tetrakis(triphenylphos Pin) palladium (0) (1.6 g, 1.4 mmol), potassium carbonate (9.6 g, 70 mmol), toluene 140 mL, ethanol 35 mL, and water 35 mL were added and dissolved, followed by refluxing for 2.5 hours. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-151 (8.5 g, yield: 47 %).

[Synthesis Example 9] Preparation of compound C-194

Compound 1-1 (10 g, 41 mmol) and 410 mL of THF were dissolved in a flask, and then 2.5M n-BuLi in hexane (21.6 mL, 54 mmol) was slowly added dropwise at -78°C under a nitrogen atmosphere. After 2 hours, 2,4-dichloro-6-(dibenzo[b,d]furan-1-yl)-1,3,5-triazine (17 g, 53.6 mmol) was added and stirred at room temperature for 18 hours. . When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-194 (6.2 g, yield: 21 %).

[Synthesis Example 10] Preparation of compound C-222

In a flask, compound 2-1 (10.4 g, 24 mmol), 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole (4.0 g, 12 mmol), Pd ₂ dba ₃ (0.55 g) , 0.6 mmol), P(t-Bu) ₃ (0.6 mL, 1.2 mmol), NaOtBu (2.9 g, 30 mmol), and o-xylene 120 mL were added and dissolved, followed by reflux for 1 hour. When the reaction was completed, the organic layer was extracted with ethyl acetate. The organic layer was dried to remove residual moisture using magnesium sulfate, and separated by column chromatography to obtain compound C-222 (5.2 g, yield: 60 %).

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

[Device Examples 1 to 9] Preparation of OLED according to the present invention

An OLED device according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω/□) on a glass for OLED (Giomatec) substrate was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then placed in isopropanol and stored before use. Next, after mounting the ITO substrate in the substrate holder of the vacuum deposition equipment, the compound HI-1 is put into a cell in the vacuum deposition equipment, the compound HT-1 is put into another cell, and the two materials are evaporated at different rates to form the compound A hole injection layer was deposited by doping the compound HI-1 to a thickness of 10 nm in an amount of 3 wt% based on the total amount of HI-1 and compound HT-1 . Then, a compound HT-1 as a first hole transport layer 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 first host material and the second host material shown in Table 1 as hosts in a cell in the vacuum deposition equipment, and putting compound D-71 as a dopant in another cell, the two host materials were mixed at a rate of 1:1. A light emitting layer having a thickness of 40 nm was deposited on the second hole transport layer by evaporating and simultaneously evaporating the dopant material at different rates to dope the dopant in an amount of 3 wt% with respect to the total amount of the host and the dopant. Subsequently, 35 nm of compound ETL-1 : EIL-1 was deposited as an electron transport layer on the light emitting layer at a weight ratio of 50:50. Then, as an electron injection layer, compound EIL-1 was deposited to a thickness of 2 nm on the electron transport layer, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition equipment to prepare an OLED device. . For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

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

An OLED was manufactured in the same manner as in Device Example 1, except that the second host compound of Table 1 was used alone as a host of the light emitting layer.

As described above, the driving voltage, luminous efficiency, luminous color, and light intensity based on 5,000 nit luminance of the OLEDs manufactured in Comparative Example 1 and Device Examples 1 to 9 based on 1,000 nit luminance fall from 100% to 95% (Lifetime: T95) is shown in Table 1 below.

[Table 1]

[Device Examples 10 to 14] Preparation of green light emitting OLED according to the present invention

An OLED was manufactured in the same manner as in Device Example 1, except that the second hole transport layer, the light emitting layer, and the electron transport layer were deposited as follows. As the second hole transport layer, the compound HT-3 was put into another cell in the vacuum deposition equipment, and the cell was evaporated by applying an electric current to deposit a second hole transport layer having a thickness of 30 nm on the first hole transport layer. After the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows. As a light emitting layer, each of the first hosts listed in Table 2 below as hosts in two cells in the vacuum deposition equipment and a second host, and after putting the compound PGD as a dopant in another cell, the two host materials are evaporated at different rates of 2:1 and the dopant materials are evaporated at different rates at the same time to the total amount of the host and the dopant. A light emitting layer having a thickness of 40 nm was deposited on the hole transport layer by doping a dopant in an amount of 10 wt %. Subsequently, 35 nm of compound ETL-1 : EIL-1 as an electron transport material was deposited on the light emitting layer in a weight ratio of 40:60.

As described above, the driving voltage, luminous efficiency, and luminous color based on 1,000 nit luminance of the OLEDs manufactured in Device Examples 10 to 14 are shown in Table 2 below.

[Table 2]

From Tables 1 and 2, an organic electroluminescent device including a compound of a specific combination according to the present application as a host material, compared to an organic electroluminescent device using a conventional compound as a single host material (Comparative Example 1), a lower driving voltage , it can be confirmed that high luminous efficiency and/or improved lifespan characteristics are exhibited. That is, it can be seen that the light emitting properties of the organic electroluminescent compounds of the present application are superior to those of conventional materials. In addition, it can be seen that the device using the compound for an organic electroluminescent material according to the present application as a host material for light emission exhibits excellent luminous efficiency characteristics.

The compounds used in the device Examples and Comparative Examples are shown in Table 3 below.

[Table 3]

Claims (14)

A plurality of types of host materials, including a first host material including a compound represented by Formula 1 below, and a second host material including a compound represented by Formula 2 or Formula 3 below:
[Formula 1]

In Formula 1,
Ring A and Ring B are each independently a substituted or unsubstituted (C6-C30) arene, or a substituted or unsubstituted (3-30 membered) heteroarene;
L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
HAr is a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;
[Formula 2]

In Formula 2,
X ₂₁ and Y ₂₁ are each independently -N=, -NR ₃₁ -, -O-, or -S-, provided that any one of X ₂₁ and Y ₂₁ is -N=, and X ₂₁ and Y ₂₁ the other is -NR ₃₁ -, -O-, or -S-;
R ₂₁ and R ₃₁ are each independently a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30 membered)heteroaryl;
R ₂₂ 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, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -L-NR ₁ R ₂ , or -L ₂₁ -Ar ₂₁ ; may be linked with adjacent substituents to form a ring;
provided that at least one of R ₂₂ to R ₂₉ is -L ₂₁ -Ar ₂₁ ;
L ₂₁ is each independently a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₂₁ is each independently a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -NR ₃₂ R ₃₃ ;
R ₃₂ and R ₃₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted a fused ring group of a cyclic (3-30 membered) heteroaryl, or a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;
L is a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 membered) heteroarylene, a substituted or unsubstituted divalent (C2-C30) aliphatic hydrocarbon group, or a fused ring group of a substituted or unsubstituted divalent (C3-C30) aliphatic ring and a (C6-C30) aromatic ring;
R ₁ and R ₂ are each independently hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl.
[Formula 3]

In Formula 3,
A ₁ and A ₂ are each independently a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, or a substituted or unsubstituted carbazolyl; ;
one of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are linked to each other to form a single bond;
X ₁₅ to X ₂₂ that does not form a single bond, X ₁₁ to X ₁₄ , and X ₂₃ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted It may be a cyclic (3-30 membered) heteroaryl, or may be linked with an adjacent substituent to form a ring. 2. The substituted heteroarylene, substituted dibenzofura of claim 1, wherein said substituted alkyl, substituted alkenyl, substituted aryl, substituted arene, substituted arylene, substituted heteroaryl, substituted heteroarene, substituted heteroarylene, substituted dibenzofura nyl, substituted dibenzothiophenyl, substituted carbazolyl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted The substituents of the fused ring group of the aliphatic ring and the aromatic ring, the substituted divalent aliphatic hydrocarbon group, or the fused ring group of the substituted divalent aliphatic ring and the aromatic ring are each independently deuterium, halogen, cyano, carboxyl, Nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio , (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, one or more (C6-C30 (3-30 membered)heteroaryl unsubstituted or substituted with aryl, (C6-C30)aryl unsubstituted or substituted with one or more (3-30 membered)heteroaryl, tri(C1-C30)alkylsilyl, tri (C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, (C3-C30) aliphatic ring and (C6- A fused ring group of an aromatic ring of C30), amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C2-C30)alkenylamino, (C1-C30)alkyl (C2-C30) Alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di- (3-30 membered)heteroarylamino , (C1-C30) alkyl (3-30 membered) heteroarylamino, (C2-C30) alkenyl (C6-C30) arylamino, (C2-C30) alkenyl (3-30 membered) heteroarylamino, ( C6-C30) aryl (3-30 membered) heteroarylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) Arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl , at least one selected from the group consisting of (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl, a plurality of kinds of host materials. According to claim 1, wherein the formula (1) is represented by any one of the following formula, a plurality of types of host material:

In the above formula,
R ₁₀₁ to R ₁₅₀ 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 substituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl (C6 -C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted (C3-C30) is a fused ring group of an aliphatic ring and an aromatic ring of (C6-C30), or -L-NR ₁ R ₂ ,
HAr, Ar, L ₁ , L ₂ , L, R ₁ and R ₂ are as defined in claim 1. According to claim 1, wherein HAr in Formula 1 is substituted or unsubstituted pyridyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted Quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted carba Jolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl , a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl, a plurality of host materials. According to claim 1, wherein the formula 2 is represented by any one of the following formula, a plurality of types of host material:

In the above formula,
X ₂₁ , Y ₂₁ , L ₂₁ , Ar ₂₁ , and R ₂₁ to R ₂₉ are as defined in claim 1. The method according to claim 1, wherein Ar ₂₁ in Formula 2 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted substituted or unsubstituted benzo[c]phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentain-fluoren]yl, substituted or unsubstituted spiro[dihydroinden-fluoren]yl, substituted or unsubstituted spiro[benzofluorene-fluoren]yl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothio phenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, or substituted or unsubstituted benzonaphtho furanyl; Phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, dimethylfluorenyl, diphenyl At least selected from the group consisting of fluorenyl, dimethylbenzofluorenyl, phenanthrenyl, dibenzothiophenyl substituted or unsubstituted with phenyl, benzonaphthofuranyl, and dibenzofuranyl substituted or unsubstituted with phenyl A plurality of types of host material, which is amino substituted with one substituent. According to claim 1, wherein the compound represented by Formula 1 is at least one selected from the following compounds, a plurality of types of host material.

In the above compounds, D means deuterium, and n means the number of deuterium. According to claim 1, wherein the compound represented by Formula 2 is at least one selected from the following compounds, a plurality of types of host material.

The plurality of host materials according to claim 1, wherein the compound represented by Formula 3 is at least one selected from the following compounds.

In the above compounds, Dn means that n hydrogens have been replaced with deuterium, n is an integer greater than or equal to 1, and the number of hydrogens in each compound is set as the upper limit. anode; cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of types of host materials according to claim 1 . An organic electroluminescent compound represented by the following formula (4):
[Formula 4]

In Formula 4,
A ring and B ring are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring;
L ₁ is a single bond;
L ₂ is a single bond, or a substituted or unsubstituted (C6-C30)arylene;
Ar is substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;
HAr is a substituted or unsubstituted nitrogen-containing (3-20 membered) heteroaryl;
However, HAr

Except for the case of heteroaryl substituted with a phosphorus substituent,
wherein R ₃₀₀ is (C1-C30)alkyl, or (C6-C30)aryl;
The * represents the bonding position of the substituent,
The following compounds are also excluded.

The organic electroluminescent compound according to claim 11, wherein the compound represented by Formula 4 is selected from the following compounds.

In the above compounds, D means deuterium, and n means the number of deuterium. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 11 . An organic electroluminescent device comprising the organic electroluminescent material according to claim 13 .

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