KR20240021108A - A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to multiple types of host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same, by including a specific combination of compounds according to the present disclosure as multiple types of host materials, or by including the compounds according to the present disclosure. It is possible to provide an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifespan characteristics compared to the organic electroluminescent device.

Description

Multiple types of host materials, organic electroluminescent compounds, and organic electroluminescent devices comprising the same

The present invention relates to multiple types of host materials, organic electroluminescent compounds, and organic electroluminescent devices containing the same.

Since Eastman Kodak's Tang et al. first developed a TPD/Alq3 double-layer small molecule green organic electroluminescent device (OLED) consisting of a light-emitting layer and a charge transport layer in 1987, research on organic electroluminescent devices has progressed rapidly and is now commercialized. reached. Currently, organic electroluminescent devices mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. In many application fields such as TV and lighting, the problem of insufficient OLED lifespan is faced, and high efficiency of OLED is still required. In general, the higher the luminance of an OLED, the shorter the lifespan of the OLED. Therefore, OLEDs with long lifespan are required for long-term use and high resolution of displays.

Meanwhile, Korean Patent Registration No. 1612164 discloses a compound in which an amine group is fused to a dibenzo moiety containing carbazole, fluorene, or a 5-membered heterocycle to form a ring, but the specific compounds and specific combinations claimed herein The host material is not specifically disclosed. In addition, there is a continuous need to develop light-emitting materials with improved performance, such as improved driving voltage, luminous efficiency, and/or lifetime characteristics compared to previously disclosed organic electroluminescent devices.

Korean Patent Publication No. 1612164 (announced on April 12, 2016)

The purpose of the present application is to provide a plurality of types of host materials that can provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and/or lifespan characteristics. Another object of the present application is to provide an organic electroluminescent compound with a new structure suitable for application to organic electroluminescent devices. Another object of the present application is to provide an organic electroluminescent device with significantly improved driving voltage, luminous efficiency and/or lifespan characteristics by including the compound or a specific combination of compounds of the present application.

As a result of intensive research to solve the above technical problems, the present inventors have discovered a plurality of types of hosts comprising one or more first host compounds represented by the following formula (1) and one or more second host compounds represented by the following formula (2) The present invention was completed by discovering that a material or a compound represented by any one of the following formulas 1' or formulas 2'-1 to 2'-4 achieves the above-mentioned object.

[Formula 1]

In Formula 1,

X is -O-, -S-, -N(R)-, C(R')(R")- or -Se-;

R, R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, - L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ), or R' and R" are connected to each other to form a ring. may be formed, and R' and R" may be the same or different from each other;

R ₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted aliphatic ring (C3-C30) and an aromatic ring (C6-C30), -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ ) -L ₃ -N-(Ar ₄ )(Ar ₅ ); Can be connected to adjacent substituents to form a ring;

However, at least one of R, R', R", and R ₁ to R ₁₃ is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N- (Ar ₄ )(Ar ₅ );

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

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

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

[Formula 2]

In Formula 2,

X ₁ to X ₃ are each independently -N= or -C(R ₂₀ )=, provided that at least one of X ₁ to X ₃ is N;

R ₂₀ 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, or substituted or unsubstituted ( It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30);

L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;

Ar ₆ to Ar ₈ are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or *-N-(R ₂₁ )(R ₂₂ ); Can be connected to adjacent substituents to form a ring; However, at least one of Ar ₆ to Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

R ₂₁ and R ₂₂ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or It is an unsubstituted (3-30 membered) heteroaryl.

[Formula 1']

In Formula 1',

X is -N(R)-, -C(R')(R")- or -Se-;

R, R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, - L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ), or R' and R" are connected to each other to form a ring. may be formed, and R' and R" may be the same or different from each other;

R ₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted aliphatic ring (C3-C30) and an aromatic ring (C6-C30), -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ ) -L ₃ -N-(Ar ₄ )(Ar ₅ ); Can be connected to adjacent substituents to form a ring;

However, at least one of R, R', R", and R ₁ to R ₁₃ is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N- (Ar ₄ )(Ar ₅ );

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

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

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

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

[Formula 2'-3] [Formula 2'-4]

In the above formulas 2'-1 to 2'-4,

T is O or S;

_{X 1} ' to ) heteroaryl;

L ₄ ' to L ₆ ' are each independently a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium;

Ar ₇ ' and Ar ₈ ' are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl;

In the above formula 2'-1,

X ₆ ' to X ₈ ' are each independently hydrogen, _{deuterium ,} or -L ₇ -Ar ₉ , provided that at least _one of X ₆ ' to

_{When _ _ _ _} phenyl, biphenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium; However, when L ₇ is a single bond, Ar ₉ is naphthyl substituted or unsubstituted with deuterium;

_{When _ _ _ _} phenyl, biphenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium;

_{When _ _ _ _} phenyl, or naphthyl substituted or unsubstituted with deuterium;

However, when X ₈ ' is -L ₇ -Ar ₉ and is phenyl, at least one of Ar ₇ ' and Ar ₈ ' is dibenzofuranyl or dibenzothiophenyl;

In the above formula 2'-2,

X ₈ ' is -L ₇ -Ar ₉ , and X ₅ ' and X ₇ ' are each independently hydrogen or deuterium;

L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, and Ar ₉ is hydrogen, phenyl substituted or unsubstituted with deuterium, or ratio substituted or unsubstituted with deuterium. phenyl, or naphthyl substituted or unsubstituted with deuterium or phenyl;

However, when L ₇ is a single bond, Ar ₉ is naphthyl substituted or unsubstituted with deuterium;

In the above formula 2'-3

X ₅ ', X ₆ ' and X ₈ ' are each independently hydrogen _{, deuterium or} -L ₇ -Ar ₉ , provided that at least _one of X ₅ ', and;

L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, and Ar ₉ is phenyl substituted or unsubstituted with deuterium or naphthyl, or unsubstituted or substituted with deuterium. Biphenyl, or naphthyl substituted or unsubstituted with deuterium;

_However , _{in the case where} It is unsubstituted dibenzofuranyl;

In the above formula 2'-4,

X ₅ ' to X ₇ ' are each independently hydrogen, deuterium, or -L ₇ -Ar ₉ , provided that at least one of X ₅ ' to X ₇ ' is -L ₇ -Ar ₉ ;

L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, Ar ₉ is phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, Or it is naphthyl substituted or unsubstituted with deuterium.

By including a specific combination of compounds according to the present disclosure as a plurality of host materials, or by including the compounds according to the present disclosure, organic electroluminescent devices exhibit significantly improved driving voltage, luminous efficiency and/or lifespan characteristics compared to conventional organic electroluminescent devices. Electroluminescent devices can be manufactured.

1 to 5 are representative chemical formulas of organic electroluminescent compounds according to the present application.

The present application is described in more detail below, but this is for illustrative purposes only and should not be construed as limiting the scope of the present application.

As used herein, “organic electroluminescent compound” refers to a compound that can be used in an organic electroluminescent device and, if necessary, may be included in any layer constituting the organic electroluminescent device.

As used herein, “organic electroluminescent material” refers to a material that can be used in an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent materials include hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials (including host materials and dopant materials), electron buffer materials, hole blocking materials, It may be an electron transfer material, an electron injection material, etc.

As used herein, “plural types of host materials” refers to a host material containing a combination of two or more compounds that can be included in any light-emitting layer constituting the organic electroluminescent device, and before being included in the organic electroluminescent device (e.g. For example, it may refer to both the material included (e.g., before deposition) and the material included (e.g., after deposition). For example, the plurality of host materials of the present application are a combination of two or more host materials, and may optionally further include common materials included in organic electroluminescent materials. Two or more types of compounds included in the plurality of host materials of the present application may be included together in one light-emitting layer, or may be included in different light-emitting layers. For example, the two or more types of host materials may be mixed or co-deposited, or may be deposited individually.

As used herein, “(C1-C30)alkyl” refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms, where 1 to 20 carbon atoms are preferred, and 1 to 10 carbon atoms are more preferred. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl, etc. As used herein, “(C3-C30)cycloalkyl(lene)” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, where 3 to 20 carbon atoms are preferred, and 3 to 7 carbon atoms are more preferred. desirable. 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 contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si and P, preferably O and S. and N, and include cycloalkyl containing one or more heteroatoms selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, “(C6-C30)aryl(lene)” refers to a single-ring or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms, and may be partially saturated. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, and benzofluorene. Nyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobiflu These include orenyl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyldihydrophenanthrenyl, and cumenyl. 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, dibenzofluorenyl, 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-quarterphenyl, 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]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[ b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b] Fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluore Nyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11, 11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11 -Diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11, 11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11 , 11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl , 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluore Nyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl orenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c] Fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c ]Fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[ c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl -9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9 , 10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc.

As used herein, “(3-30 membered) heteroaryl (len)” has 3 to 30 ring skeleton atoms and contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se and Ge. It means containing an aryl (lene) group. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl herein includes forms in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and also includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, and tetrazinyl. , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. single ring heteroaryl, 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, phenoxazolyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyridyl. There are fused ring heteroaryls such as midinyl, 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-quinolyl 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-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole- 1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3 -Methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl , 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho- [1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho -[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naph to-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1- Naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4 -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]-benzofuran 1, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzo furanyl, 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 midinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9- Benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2- d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzo Thio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d] Pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-ger Mafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. As used herein, “halogen” includes F, Cl, Br and I atoms.

Additionally, “ortho (o-)”, “meta (m-)”, and “para (p-)” are prefixes that indicate the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other. For example, when the substituents are in the 1st and 2nd positions in a benzene substituent, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions. For example, in a benzene substituent, when the substituents are at the 1st and 3rd positions, it is called a meta position. Para indicates that two substituents are at the 1 and 4 positions. For example, in a benzene substituent, when the substituents are at the 1 and 4 positions, it is called the para position.

In the description of "substituted or unsubstituted" described herein, 'substitution' means replacing a hydrogen atom in a certain functional group with another atom or another functional group (i.e., a substituent), and substitution with a group where two or more substituents among the substituents are connected. It also includes becoming. For example, “a substituent group in which two or more substituents are connected” may be pyridine-triazine. That is, pyridine-triazine may be interpreted as one heteroaryl substituent or as two heteroaryl substituents connected. In the formulas herein, substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, The substituents of substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted trialylsilyl, and fused ring groups of substituted aliphatic rings and aromatic rings are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl unsubstituted or substituted with one or more (C6-C30)aryl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl unsubstituted or substituted with one or more (C6-C30)aryls; (C6-C30)aryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; Substituted or unsubstituted mono- or di- (C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, which may be further substituted with deuterium. According to one aspect of the present application, the substituents are each independently: deuterium; cyano; (C1-C20)alkyl; (C6-C25)aryl; (5-25 members) heteroaryl; Substituted or unsubstituted di(C6-C25)arylamino; and (C6-C25)ar(C1-C20)alkyl. According to another aspect of the present application, the substituents are each independently deuterium; cyano; (C1-C10)alkyl; (C6-C20)aryl; (5-20 won) heteroaryl; Di(C6-C18)arylamino substituted or unsubstituted with deuterium; and (C6-C18)ar(C1-C10)alkyl. For example, the substituents include deuterium, cyano, methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, fluorenyl, phenylfluorenyl, cumenyl, isopropyl substituted with phenyl, triphenylsilyl, carboxylic acid. It may be one or more selected from the group consisting of zolyl, dibenzofuranyl, dibenzothiophenyl, phenylbiphenylamino, and diphenylamino, and may be further substituted with one or more deuterium.

As used herein, the ring formed by connecting adjacent substituents refers to a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring formed by connecting or fusion of two or more adjacent substituents. do. The ring may preferably be a substituted or unsubstituted (3-25 membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof, and even more preferably (C6-C18)aryl and ( It may be a (5-25 membered) monocyclic or polycyclic aromatic ring substituted or unsubstituted with one or more of 5-25 membered heteroaryl. Additionally, the ring formed may contain one or more heteroatoms selected from B, N, O, S, Si, P, Se and Ge, preferably one or more heteroatoms selected from N, O, S and Se. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring substituted or unsubstituted with one or more phenyls, a phenanthrene ring, an indole ring, a xanthene ring, a benzopyridine ring, and a benzothienopyridine. It may be a ring, a dibenzothiophene ring, a dibenzofuran ring, a naphthalene ring, a benzofluorene ring, a benzothiophene ring, a benzofuran ring, an indene ring, a carbazole ring, etc.

As used herein, heteroaryl(lene) and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si, P, Se, and Ge. 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 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (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 member) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3-30 member) heteroarylamino. More than one 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 first host compound represented by Formula 1, and the second host material includes It includes at least one second host compound represented by Formula 2.

The first host compound, which is a host material according to one embodiment, may be represented by Formula 1 above.

In Formula 1, R)-, C(R')(R")- or -Se-.

Wherein R, R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ), or R' and R" are connected to each other to form a ring. may be formed, and R' and R" may be the same or different from each other. According to one aspect of the present application, R, R' and R" are each independently substituted or unsubstituted (C1-C20)alkyl, -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ). According to another aspect of the present application, R, R' and R" are each independently unsubstituted (C1-C10)alkyl, -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N( Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ). For example, R is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )- L ₃ -N-(Ar ₄ )(Ar ₅ ), and R' and R" may be methyl.

In Formula 1, R ₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted. Substituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, Substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30) ) Arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ - N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ); It can be connected to adjacent substituents to form a ring. For example, R ₁ to R ₁₃ are each independently hydrogen, deuterium, -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ).

In Formula 1, at least one of R, R', R" and R ₁ to R ₁₃ is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ - N-(Ar ₄ )(Ar ₅ ). According to one aspect of the present application, one or both of R, R', R" and R ₁ to R ₁₃ are each -L ₁ -N-(Ar ₁ ) (Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ).

In Formula 1, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or 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, substituted or unsubstituted (C6-C25)arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C18)arylene, or unsubstituted (5-20 membered) heteroarylene. The substituents of the substituted arylene and substituted heteroarylene may each independently be one or more selected from the group consisting of deuterium, (C6-C30)aryl, and di(C6-C30)arylamino. For example, L ₁ and L ₂ may each independently be a single bond, substituted or unsubstituted phenylene, unsubstituted naphthylene, unsubstituted dibenzofuranylene, etc., and the substituent of the substituted phenylene is deuterium. , phenyl, naphthyl, diphenylamino substituted or unsubstituted with deuterium, and phenylbiphenylamino.

In Formula 1, L ₃ is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one aspect of the present application, L ₃ is substituted or unsubstituted (C6-C25)arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L ₃ is (C6-C18)arylene substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. For example, L ₃ may be phenylene substituted or unsubstituted with one or more of deuterium and phenyl.

In Formula 1, Ar ₁ to Ar ₅ are each independently selected from substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, or substituted or unsubstituted (C3-C30). It is a fused ring group of an aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-25 membered) heteroaryl. According to another aspect of the present application, Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C18)aryl, or (5-20 membered) heteroaryl substituted or unsubstituted with (C6-C18)aryl. am. The substituents of the substituted aryl are selected from the group consisting of deuterium, (C1-C30)alkyl, (C6-C30)aryl, (3-30 membered)heteroaryl, and (C6-C30)ar(C1-C30)alkyl. There may be more than one. Specifically, Ar ₁ to Ar ₅ are each independently substituted or unsubstituted, phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, spirobifluorenyl, Quarterphenyl, cumenyl, carbazolyl, phenanthrenyl, benzophenanthrenyl, chrysenyl, triphenylenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofluorenyl, benzothiazolyl, It may be benzoxazolyl, benzimidazolyl, naphthooxazolyl, benzonaphthooxazolyl, naphthothiazolyl, benzonaphthothiazolyl, or naphthoimidazolyl. For example, Ar ₁ to Ar ₅ are each independently substituted or unsubstituted phenyl, naphthyl, o-biphenyl, m-biphenyl, p-biphenyl, naphthylphenyl, phenylnaphthyl, phenanthrenyl, Dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, o-terphenyl, m-terphenyl, o-quaterphenyl, dibenzofuranyl substituted or unsubstituted with phenyl, dibenzothiophenyl, phenyl It may be carbazolyl, dibenzoselenophenyl, benzonaphthofuranyl, etc., and the substituent of the substituted phenyl may be one or more selected from the group consisting of deuterium, dibenzofuranyl, carbazolyl, isopropyl substituted with phenyl, and cumenyl. and these may be further substituted with deuterium.

According to one aspect of the present application, Formula 1 may be represented by one or more of the following Formulas 1-1 to 1-28.

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

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

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10]

[Formula 1-11] [Formula 1-12]

[Formula 1-13] [Formula 1-14]

[Formula 1-15] [Formula 1-16]

[Formula 1-17] [Formula 1-18]

[Formula 1-19] [Formula 1-20]

[Formula 1-21] [Formula 1-22]

[Formula 1-23] [Formula 1-24]

[Formula 1-25] [Formula 1-26]

[Formula 1-27] [Formula 1-28]

In Formulas 1-1 to 1-28, the definitions and preferred embodiments of X, R ₁ to R ₁₃ , L ₁ to L ₃ , and Ar ₁ to Ar ₅ are the same as in Formula 1.

The second host compound, which is another host material according to one embodiment, may be represented by Formula 2 above.

In Formula 2, X ₁ to X ₃ are each independently -N= or -C(R ₂₀ )=, provided that at least one of X ₁ to X ₃ is N. According to one aspect of the present application, at least two of X ₁ to X ₃ are N. According to another aspect of the present application, all of X ₁ to X ₃ are N.

R ₂₀ 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, or substituted or unsubstituted It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30). For example, R ₂₀ may be hydrogen or deuterium.

In Formula 2, L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted It is a (3-30 won) heteroarylene. According to one aspect of the present application, L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C6-C25)arylene, or substituted or unsubstituted (5-25 membered) heteroarylene. According to another aspect of the present application, L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C6-C18)arylene, or substituted or unsubstituted (5-20 membered) heteroarylene. For example, L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted, phenylene, naphthylene, biphenylene, naphthylphenylene, phenylnaphthylene, fluorenylene, phenanthrenylene, It may be pyridylene, carbazolilene, dibenzofuranylene, dibenzothiophenylene, benzonaphthothiophenylene, naphthooxazolylene, naphthothiazolilene, or benzonaphthofuranylene.

In Formula 2, Ar ₆ to Ar ₈ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or Unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl. , substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6- C30) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or *-N-(R ₂₁ )(R ₂₂ ); It can be connected to adjacent substituents to form a ring, provided that at least one of Ar ₆ to Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl. According to one aspect of the present application, Ar ₆ to Ar ₈ are each independently substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-25 membered)heteroaryl, or substituted or unsubstituted tri. (C6-C25)arylsilyl. According to another aspect of the present application, Ar ₆ to Ar ₈ are each independently substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-18 membered) heteroaryl, or substituted or unsubstituted (5-18 membered) heteroaryl. It is tri(C6-C18)arylsilyl.

As an example, at least one of Ar ₆ to Ar ₈ may be substituted or unsubstituted (5-30 membered) heteroaryl, and preferably at least two of Ar ₆ to Ar ₈ are substituted or unsubstituted (5-30 membered) heteroaryl. circle) may be heteroaryl.

For example, Ar ₆ to Ar ₈ may all be substituted or unsubstituted (C6-C30)aryl.

Specifically, Ar ₆ to Ar ₈ are each independently substituted or unsubstituted, phenyl, naphthyl, p-biphenyl, m-biphenyl, o-biphenyl, o-terphenyl, m-terphenyl, p -Terphenyl, triphenylsilyl, triphenylgermanyl, dibenzofuranyl, dibenzothiophenyl, benzoselenophenyl, fluorenyl, spirobifluorenyl, carbazolyl, phenanthrenyl, benzophenanthrenyl, Chrysenyl, triphenylenyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofluorenyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, naphthooxazolyl, benzonaphthooxa It may be zolyl, naphthothiazolyl, benzonaphthothiazolyl, or naphthoimidazolyl. For example, Ar ₆ to Ar ₈ are each independently substituted or unsubstituted, phenyl, naphthyl, p-biphenyl, m-biphenyl, o-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, triphenylsilyl, triphenylgermanyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, phenanthrenyl, chry It may be cenyl, triphenylenyl, carbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzonaphthooxazolyl, benzonaphthothiazolyl, or naphthoselenazolyl. Here, the substituents of the substituents may be one or more selected from deuterium, cyano, methyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylsilyl, fluorenyl, dibenzothiophenyl, and dibenzofuranyl. .

According to one aspect of the present application, at least one of Ar ₆ to Ar ₈ may be any one selected from the following formulas 2-1 to 2-17.

[Formula 2-1] [Formula 2-2] [Formula 2-3]

[Formula 2-4] [Formula 2-5]

[Formula 2-6] [Formula 2-7]

[Formula 2-8] [Formula 2-9]

[Formula 2-10] [Formula 2-11]

[Formula 2-12] [Formula 2-13]

[Formula 2-14] [Formula 2-15]

[Formula 2-16] [Formula 2-17]

In Formulas 2-1 to 2-17,

T is O, S, C(R ₁₇ )(R ₁₈ ), N(R ₁₉ ), or Se;

Y ₁ and Y ₂ are each independently -N=, -N(R ₂₁ )-, -O-, -S-, or -Se-; provided that one of Y ₁ and Y ₂ is -N=, and the other of Y ₁ and Y ₂ is -N(R ₂₁ )-, -O-, -S-, or -Se-;

R ₁ to R ₁₅ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(R ₂₂ )(R ₂₃ ); Can be connected to adjacent substituents to form a ring;

R ₂₂ and R ₂₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or It is unsubstituted (3-30 membered) heteroaryl;

R ₁₇ to R ₁₉ and R ₂₁ are each independently selected from substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) hetero is aryl; Can be connected to adjacent substituents to form a ring;

L ₈ is a single bond, substituted or unsubstituted (C6-C30)arylene or substituted or unsubstituted (3-30 membered)heteroarylene;

Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

a and d are integers from 1 to 5, b, e', f, i, and o' are integers from 1 to 3, and c, e, h, f', l, i', and o are integers from 1 to 3. is an integer of 4, d' is an integer of 1 to 6, g, j, k, m, and n' are integers of 1 or 2, and g', j', m', and n are 1;

When a to m, o, d' to f', i', n', and o' are integers of 2 or more, each of R ₁ to R ₁₅ may be the same or different from each other;

* is the connection position with L ₄ to L ₆ in Chemical Formula 2.

As an example, T may be O, S, Se, or CR ₁₇ R ₁₈ , where R ₁₇ and R ₁₈ are each independently substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C6) -C30) It may be aryl.

For example, one of Y ₁ and Y ₂ may be -N=, and the other of Y ₁ and Y ₂ may be -O-, -S-, or -Se-.

For example, R ₁ to R ₁₅ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered)heteroaryl, or substituted or unsubstituted It may be a substituted tri(C6-C30)arylsilyl, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-25 membered)heteroaryl, or substituted or It may be unsubstituted tri(C6-C25)arylsilyl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18)aryl, substituted or unsubstituted (5-18 membered) heteroaryl, or It may be substituted or unsubstituted tri(C6-C18)arylsilyl. For example, R ₁ to R ₁₅ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted Naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted dibenzofuranyl, substituted Alternatively, it may be unsubstituted dibenzothiophenyl, or substituted or unsubstituted benzonaphthooxazolyl.

As an example, Ar ₈ may be substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (5-30 membered)heteroaryl, preferably substituted or unsubstituted (C6-C25)aryl or It may be substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18)aryl or substituted or unsubstituted (5-18 membered) heteroaryl. For example, Ar ₈ is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted It may be unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. At this time, the substituents of the substituents may be at least one selected from deuterium, cyano, methyl, phenyl, triphenylsilyl, and triphenylgermanyl.

According to another embodiment of the present invention, the present disclosure provides an organic electroluminescent compound represented by Formula 1', and an organic electroluminescent device containing the same.

In formula 1', X is -N(R)-, -C(R')(R")-, or -Se-. In formula ₁ ', The definition and preferred embodiment of R ₁₃ are the same as in Formula 1 above.

According to another embodiment of the present invention, the present application provides an organic electroluminescent compound represented by any one of Formulas 2'-1 to 2'-4, and an organic electroluminescent device containing the same. Formula 1 or 1' The compound represented by may be one or more selected from the following compounds, but is not limited to these.

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

The compound represented by any one of the above formulas 2'-1 to 2'-4 may be one or more selected from the following compounds, but is not limited to these.

Compounds represented by Formula 1 or 1' herein can be prepared by synthetic methods known to those skilled in the art, for example, by referring to Schemes 1 to 6 below, but are not limited thereto.

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

[Scheme 6]

In Schemes 1 to 6, R', R", L ₁ to L ₃ , and Ar ₁ to Ar ₅ are each defined in Formula 1.

Although exemplary synthesis examples of compounds represented by Formula 1 or 1' have been described above, these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, and Suzuki cross-coupling. reaction, Wittig 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. Those skilled in the art will easily understand that the above reaction proceeds even if other substituents defined in Formula 1 or 1' are combined in addition to the substituents specified in the specific synthesis examples.

The host compound represented by Formula 2 herein may be manufactured by referring to a synthesis method known to those skilled in the art, for example, the synthesis method disclosed in Korean Patent Publication No. 10-2020-0092879, etc., but is not limited thereto.

Host compounds represented by formulas 2'-1 to 2'-4 herein include, for example, Korean Patent Publication No. 10-2014-0099082, International Publication WO 2015/169412 A1, Korean Patent Publication No. 10- It can be manufactured by referring to the synthesis method disclosed in 2018-0112962, etc., but is not limited thereto.

Hereinafter, an organic electroluminescent device using the plurality of host materials and/or organic electroluminescent compounds described above will be described.

An organic electroluminescent device according to one embodiment includes an anode; cathode; and at least one light-emitting layer between the anode and the method, wherein at least one layer of the light-emitting layer comprises at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2. It may contain multiple types of host materials including. At this time, the weight ratio of the first host compound and the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30. , more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

The plurality of host materials of the present application may be included in the same organic layer, for example, the same light-emitting layer, or may be included in different light-emitting layers.

According to another example, an organic electroluminescent compound represented by Formula 1' or any one of Formulas 2'-1 to 2'-4 of the present application may be used as a host material of a light emitting layer, a hole injection layer material, a hole transport layer material, and a hole auxiliary layer. It may be included as a material, a light emitting auxiliary layer material, or an electron blocking layer material.

In addition to the light emitting layer, the organic layer is one selected from the group consisting of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. It may include more than one layer. The organic layer may further include an amine-based compound and/or azine-based compound in addition to the light-emitting material of the present application. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting layer, the light-emitting auxiliary layer, or the electron blocking layer is an amine-based compound, for example, an arylamine-based compound, a styrylarylamine-based compound, etc. It may include an injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material, and an electron blocking material. Additionally, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include an azine-based compound as an electron transport material, electron injection material, electron buffer material, and hole blocking material. In addition, the organic layer is one or more metals selected from the group consisting of Group 1, Group 2, 4th period transition metals, 5th period transition metals, lanthanide metals, and d-transition organic metals, or one or more metals containing such metals. It may further include a complex compound.

Multiple types of host materials according to one example may be used as light-emitting materials for a white organic light emitting device. The white organic electroluminescent device is arranged in a side-by-side or stacking manner depending on the arrangement of the R (red), G (green), YG (yellow green), or B (blue) light emitting units. , or a color conversion material (CCM) method, various structures have been proposed. Additionally, the plurality of host materials according to one example may also be used in an organic electroluminescent device including quantum dots (QDs).

The anode (positive electrode) and cathode (cathode) may each be formed of a transparent conductive material or a transflective or reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device may be a top emitting type, a bottom emitting type, or a double-sided emitting type.

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be comprised of multiple layers 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. Two compounds may be used simultaneously for each layer. Additionally, the hole injection layer may be doped with p-dopant. 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, thereby trapping excitons within the light-emitting layer and preventing light emission leakage. The hole transport layer or the electron blocking layer may be comprised of multiple layers, and multiple compounds may be used in each layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be composed of multiple layers for the purpose of controlling electron injection and improving the interface characteristics between the light-emitting layer and the electron injection layer, and each layer may be composed of two compounds simultaneously. The hole blocking layer is a layer located between the electron transport layer (or electron injection layer) and the light-emitting layer and prevents holes from reaching the cathode. This can improve the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or the electron transport layer may also be comprised of multiple layers, and multiple compounds may be used for each layer. Additionally, the electron injection layer may be doped with n-dopant.

The light-emitting auxiliary layer is a layer located between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is located between the anode and the light-emitting layer, it facilitates injection and/or transfer of holes or electrons. It can be used to block overflow, and when the light-emitting auxiliary layer is located between the cathode and the light-emitting layer, it can be used to facilitate injection and/or transfer of electrons or to block overflow of holes. In addition, the hole auxiliary layer is located between the hole transport layer (or hole injection layer) and the light emitting layer, and may have the effect of smoothing or blocking the transfer speed (or injection speed) of holes, thereby maintaining charge balance. ) can be adjusted. When an organic electroluminescent device includes two or more hole transport layers, the additional hole transport layer may be used as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have the effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

In the organic electroluminescent device of the present application, one or more layers selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer are placed on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as “surface layers”). ) is desirable to place. Specifically, it is preferable to dispose a chalcogenide (including oxide) layer of silicon and aluminum on the anode surface on the light-emitting medium layer side, and a metal halide layer or metal oxide layer on the cathode surface on the light-emitting medium layer side. Stabilization of the operation of the organic electroluminescent device can be achieved by the surface layer. _Preferred examples _{of the} chalcogenide include _SiO Rare earth metals, etc., and preferred examples of metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, etc.

Additionally, in the organic electroluminescent device of the present application, it is also preferable to dispose 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, the electron transfer compound is reduced to an anion, making it easy to inject and transfer electrons from the mixed region to the light-emitting medium. Additionally, since the hole transport compound is oxidized to become a cation, it becomes easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Additionally, an organic electroluminescent device that emits white light and has two or more light-emitting layers can be manufactured by using a reducing dopant layer as a charge generation layer.

The organic electroluminescent device according to one example may further include one or more dopants in the light emitting layer.

As the dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants can be used, and phosphorescent dopants are 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 metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). , preferably in some cases, may be an ortho-metalized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably in some cases, It may be an ortho-metalated iridium complex compound.

A compound represented by the following formula (101) may be used as a dopant included in the organic electroluminescent device of the present application, but is not limited thereto.

[Formula 101]

In the above formula 101,

L is any one selected from structures 1 to 3 below;

[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 substituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; It can be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, substituted or unsubstituted quinoline with pyridine, substituted or unsubstituted benzopyridine, substituted or unsubstituted benzothienopyridine, may form a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzopuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a 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 substituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; It can be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, with benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or may form unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopuropyridine, 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 or unsubstituted (C6-C30)aryl; Adjacent substituents may be connected to each other to form a substituted or unsubstituted ring;

s is an integer from 1 to 3.

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

Each layer of the organic electroluminescent device of the present invention is formed using dry film deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, or inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating. Any one of the wet film forming methods can be applied. When forming a film of the organic electroluminescent compound of the present application, or the first host compound and the second host compound, the process is carried out by co-deposition or mixed deposition.

In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the materials forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, and the solvent is used to dissolve or disperse the materials forming each layer. It can be anything, as long as there is no problem with the tabernacle.

In addition, the organic electroluminescent device of the present invention can be used to manufacture a display device, such as a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, such as an outdoor or indoor lighting device. It is possible.

Below, for a detailed understanding of the present application, we will look at the manufacturing method and physical properties of the compound according to the present application, the production method of the compound according to the present application, its physical properties, and the emission characteristics of the organic electroluminescent compound or OLED containing multiple types of host materials according to the present application, referring to the representative compounds of the present application. . However, the following examples merely illustrate the characteristics of an OLED containing an organic electroluminescent compound or multiple types of host materials according to the present application for a detailed understanding of the present application, and the present application is not limited to the examples below.

[Example 1] Preparation of Compound C-1

1) Synthesis of Compound A-2

Compound A-1 (4 g, 12 mmol), 4-bromo-2-iodobenzene (9.9 g, 34.8 mmol), CuI (1.15 g, 6 mmol), ethylenediamine (EDA) (1.4 g, 23 mmol), K ₃ PO ₄ (7.6 g, 35.8 mmol), and 60 mL of toluene were added and stirred at 130°C for 12 hours. It was cooled to room temperature and the organic layer was extracted with ethyl acetate. Residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain Compound A-2 (5 g, yield: 85%).

2) Synthesis of Compound C-1

Compound A-2 (3 g, 6.2 mmol), Compound A-3 (2.5 g, 7.4 mmol), Pd ₂ (dba) ₃ (283 mg, 0.31 mmol), S-Phos (203 mg, 0.496 mmol) in a flask. , NaOtBu (1.2 g, 124 mmol), and 126 mL of o-xylene were added and stirred at 160°C for 12 hours. It was cooled to room temperature and the organic layer was extracted with ethyl acetate. Residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound C-1 (2 g, yield: 44%).

[Example 2] Preparation of Compound C-2

Compound A-2 (2.0 g, 4.121 mol), diphenylamine (0.83 g, 4.944 mmol), NaOtBu (0.79 g, 8.242 mmol), S-Phos (135 mg, 0.329 mmol), and Pd ₂ (dba) in a flask. ) ₃ (188 mg, 0.206 mmol) was dissolved in 20 mL of xylene and stirred under reflux at 130°C for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate. Residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound C-2 (1.4 g, yield: 66%).

[Example 3] Preparation of compound E-27

Compound A-4 (8.3 g, 14.45 mmol), Compound 2 (4.6 g, 36.14 mmol), Pd(OAc) ₂ (0.32 g, 1.445 mmol), S-Phos (1.2 g, 2.891 mmol), and Cs in a flask. ₂ CO ₃ (14.1 g, 43.37 mmol) was dissolved in 80 mL of o-xylene, 20 mL of 1,4-dioxane, and 20 mL of H ₂ O, and stirred under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, MeOH was added thereto, the solid was filtered, dissolved in chlorobenzene, and then filtered through silica to obtain compound E-27 (2.5 g, yield: 28%).

[Example 4] Preparation of compound E-43

Compound A-5 (15.7 g, 37.35 mmol), Compound 3 (11 g, 29.88 mmol), Pd(pph ₃ ) ₄ (2.1 g, 1.867 mmol), and K ₂ CO ₃ (15.4 g, 112.0 mmol) in a flask. was dissolved in 55 mL of EtOH, 55 mL of H ₂ O, and 220 mL of toluene and stirred under reflux for 2 hours. After the reaction was completed, it was cooled to room temperature, MeOH was added thereto, the solid was filtered, dissolved in chlorobenzene, and then filtered through silica to obtain compound E-43 (4 g, yield: 17%).

[Device Manufacturing Examples 1 and 2] Manufacture of OLED by co-depositing the first host compound and the second host compound according to the present application

An OLED according to the present disclosure was manufactured. First, the transparent electrode ITO thin film (10Ω/□) on the OLED glass (manufactured by Geomatec) substrate was ultrasonic cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, compound HI-1 was put into a cell in the vacuum evaporation equipment and compound HT-1 was put into another cell, and then the two materials were evaporated at different rates to form the compound. Compound HI-1 was doped to a thickness of 10 nm in an amount of 3% by weight based on the total amount of HI-1 and compound HT-1, and a hole injection layer was deposited. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. Each of the first and second host compounds listed in Table 1 below were placed as hosts in two cells in the vacuum deposition equipment, and compound D-39 was placed as a dopant in another cell, and then the two host materials were added as 1: A 40 nm thick light-emitting layer was deposited on the second hole transport layer by evaporating at a rate of 1 and simultaneously evaporating the dopant material at different rates and doping the dopant in an amount of 3% by weight based on the total amount of host and dopant. . Subsequently, Compound ET-1 and Compound EI-1 as electron transport materials were evaporated at a weight ratio of 50:50 to deposit an electron transport layer with a thickness of 35 nm on the emitting layer. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Comparative Example 1] Manufacturing of OLED containing a single host

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

As described above, the driving voltage, luminous efficiency, luminous color, and light intensity based on 10,000 nit luminance of the organic electroluminescent devices manufactured in Device Manufacturing Examples 1 and 2 and Comparative Example 1 decreased from 100% to 95%. The time taken to fall (life: T95) was measured and shown in Table 1 below.

[Table 1]

From Table 1, the OLED using multiple host materials including the compound represented by Formula 1 of the present application and the compound represented by Formula 2 of the present application has a lower driving voltage compared to the OLED using the compound of Formula 2 as a single host material. , it can be confirmed that it exhibits high luminous efficiency and long lifespan characteristics.

[Device Manufacturing Examples 3 and 4] Manufacturing of OLED by depositing the host compound according to the present application

An OLED according to the present disclosure was manufactured. First, the transparent electrode ITO thin film (10Ω/□) on the OLED glass (manufactured by Geomatec) substrate was ultrasonic cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, compound HI-1 was put into a cell in the vacuum evaporation equipment and compound HT-1 was put into another cell, and then the two materials were evaporated at different rates to form the compound. Compound HI-1 was doped to a thickness of 10 nm in an amount of 3% by weight based on the total amount of HI-1 and compound HT-1, and a hole injection layer was deposited. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. The host compound listed in Table 2 below was placed as a host in a cell in the vacuum evaporation equipment, and compound D-39 was placed as a dopant in another cell, and then the dopant material was evaporated at different rates to determine the total amount of host and dopant. A 40 nm thick light emitting layer was deposited on the second hole transport layer by doping the dopant in an amount of 3% by weight. Subsequently, a 35 nm thick electron transport layer was deposited on the light emitting layer using compound ET-1 and compound EI-1 as electron transport materials at a weight ratio of 50:50. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Comparative Example 2] Preparation of OLED containing comparative compound as host

An OLED was manufactured in the same manner as Device Manufacturing Example 3, except that the host compound shown in Table 2 below was used as the host of the light-emitting layer.

As described above, the driving voltage, luminous efficiency, luminous color, and light intensity based on 10,000 nit luminance of the organic electroluminescent devices manufactured in Device Examples 3 and 4 and Comparative Example 2 decreased from 100% to 95%. The time taken to fall (life: T95) was measured and shown in Table 2 below.

[Table 2]

From Table 2, the OLED using a compound represented by any one of the formulas 2'-1 to 2'-4 of the present application as a host material has a low driving voltage, high luminous efficiency, and long-term field compared to OLED using a comparative compound as a host material. It can be confirmed that it exhibits lifespan characteristics.

Compounds used in the device manufacturing examples and comparative examples are shown in Table 3 below.

[Table 3]

Claims (13)

A plurality of types of host materials including one or more first host compounds and one or more second host compounds, wherein the first host compound is represented by the following formula (1) and the second host compound is represented by the following formula (2) , host material for multiple species:
[Formula 1]

In Formula 1,
X is -O-, -S-, -N(R)-, C(R')(R")- or -Se-;
R, R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, - L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ), or R' and R" are connected to each other to form a ring. may be formed, and R' and R" may be the same or different from each other;
R ₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted aliphatic ring (C3-C30) and an aromatic ring (C6-C30), -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ ) -L ₃ -N-(Ar ₄ )(Ar ₅ ); Can be connected to adjacent substituents to form a ring;
However, at least one of R, R', R", and R ₁ to R ₁₃ is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N- (Ar ₄ )(Ar ₅ );
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
L ₃ is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C3-C30) aliphatic ring, and (C6) -C30) aromatic ring fused ring group, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
[Formula 2]

In Formula 2,
X ₁ to X ₃ are each independently -N= or -C(R ₂₀ )=, provided that at least one of X ₁ to X ₃ is N;
R ₂₀ 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, or substituted or unsubstituted ( It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30);
L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;
Ar ₆ to Ar ₈ are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or *-N-(R ₂₁ )(R ₂₂ ); Can be connected to adjacent substituents to form a ring; However, at least one of Ar ₆ to Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₂₁ and R ₂₂ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or It is an unsubstituted (3-30 membered) heteroaryl. The method of claim 1, wherein substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, The substituents of substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted trialylsilyl, and fused ring groups of substituted aliphatic rings and aromatic rings are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl unsubstituted or substituted with one or more (C6-C30)aryl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl unsubstituted or substituted with one or more (C6-C30)aryls; (C6-C30)aryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; Substituted or unsubstituted mono- or di- (C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. The host material according to claim 1, wherein Formula 1 is represented by one or more of the following Formulas 1-1 to 1-28:
[Formula 1-1] [Formula 1-2]

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

[Formula 1-5] [Formula 1-6]

[Formula 1-7] [Formula 1-8]

[Formula 1-9] [Formula 1-10]

[Formula 1-11] [Formula 1-12]

[Formula 1-13] [Formula 1-14]

[Formula 1-15] [Formula 1-16]

[Formula 1-17] [Formula 1-18]

[Formula 1-19] [Formula 1-20]

[Formula 1-21] [Formula 1-22]

[Formula 1-23] [Formula 1-24]

[Formula 1-25] [Formula 1-26]

[Formula 1-27] [Formula 1-28]

In Formulas 1-1 to 1-28,
X, R ₁ to R ₁₃ , L ₁ to L ₃ , and Ar ₁ to Ar ₅ are as defined in claim 1. The method of claim 1, wherein Ar ₁ to Ar ₅ in Formula 1 and Ar ₆ to Ar ₈ in Formula 2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenyl. Biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl , substituted or unsubstituted quaterphenyl, substituted or unsubstituted cumenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted chry. Cenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofluore Nyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted benzonaphthooxazolyl , substituted or unsubstituted naphthothiazolyl, substituted or unsubstituted benzonaphthothiazolyl, or substituted or unsubstituted naphthoimidazolyl. The host material according to claim 1, wherein the compound represented by Formula 1 is at least one selected from the group consisting of the following compounds.

The host material according to claim 1, wherein the compound represented by Formula 2 is one or more selected from the following compounds.

An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layer includes the plurality of host materials according to claim 1. Organic electroluminescent compound represented by the formula 1':
[Formula 1']

In Formula 1',
X is -N(R)-, -C(R')(R")- or -Se-;
R, R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, - L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N-(Ar ₄ )(Ar ₅ ), or R' and R" are connected to each other to form a ring. may be formed, and R' and R" may be the same or different from each other;
R ₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted aliphatic ring (C3-C30) and an aromatic ring (C6-C30), -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ ) -L ₃ -N-(Ar ₄ )(Ar ₅ ); Can be connected to adjacent substituents to form a ring;
However, at least one of R, R', R", and R ₁ to R ₁₃ is -L ₁ -N-(Ar ₁ )(Ar ₂ ) or -L ₂ -N(Ar ₃ )-L ₃ -N- (Ar ₄ )(Ar ₅ );
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
L ₃ is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C3-C30) aliphatic ring, and (C6) -C30) aromatic ring fused ring group, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. The organic electroluminescent compound according to claim 8, wherein the compound represented by Formula 1' is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 8. Organic electroluminescent compound represented by any one of the following formulas 2'-1 to 2'-4:
[Formula 2'-1] [Formula 2'-2]

[Formula 2'-3] [Formula 2'-4]

In the above formulas 2'-1 to 2'-4,
T is O or S;
_{X 1} ' to ) heteroaryl;
L ₄ ' to L ₆ ' are each independently a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium;
Ar ₇ ' and Ar ₈ ' are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl;
In the above formula 2'-1,
X ₆ ' to X ₈ ' are each independently hydrogen, _{deuterium ,} or -L ₇ -Ar ₉ , provided that at least _one of X ₆ ' to
_{When _ _ _ _} phenyl, biphenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium; However, when L ₇ is a single bond, Ar ₉ is naphthyl substituted or unsubstituted with deuterium;
_{When _ _ _ _} phenyl, biphenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with deuterium;
_{When _ _ _ _} phenyl, or naphthyl substituted or unsubstituted with deuterium;
However, when X ₈ ' is -L ₇ -Ar ₉ and is phenyl, at least one of Ar ₇ ' and Ar ₈ ' is dibenzofuranyl or dibenzothiophenyl;
In the above formula 2'-2,
X ₈ ' is -L ₇ -Ar ₉ , and X ₅ ' and X ₇ ' are each independently hydrogen or deuterium;
L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, and Ar ₉ is hydrogen, phenyl substituted or unsubstituted with deuterium, or ratio substituted or unsubstituted with deuterium. phenyl, or naphthyl substituted or unsubstituted with deuterium or phenyl;
However, when L ₇ is a single bond, Ar ₉ is naphthyl substituted or unsubstituted with deuterium;
In the above formula 2'-3
X ₅ ', X ₆ ' and X ₈ ' are each independently hydrogen _{, deuterium or} -L ₇ -Ar ₉ , provided that at least _one of X ₅ ', and;
L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, and Ar ₉ is phenyl substituted or unsubstituted with deuterium or naphthyl, or unsubstituted or substituted with deuterium. Biphenyl, or naphthyl substituted or unsubstituted with deuterium;
_However , _{in the case where} It is unsubstituted dibenzofuranyl;
In the above formula 2'-4,
X ₅ ' to X ₇ ' are each independently hydrogen, deuterium, or -L ₇ -Ar ₉ , provided that at least one of X ₅ ' to X ₇ ' is -L ₇ -Ar ₉ ;
L ₇ is a single bond, phenylene substituted or unsubstituted with deuterium, or naphthylene substituted or unsubstituted with deuterium, Ar ₉ is phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, Or it is naphthyl substituted or unsubstituted with deuterium. The organic electroluminescent compound according to claim 11, wherein the compound represented by any one of Formulas 2'-1 to 2'-4 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 11.

Images