KR20240028926A - 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 with improved lifespan characteristics compared to the organic electroluminescent device of

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 Publication Nos. 2019-0113663 and 2015-0036736 disclose carbazole derivative compounds, but do not specifically disclose the specific compounds and specific combinations of host materials claimed herein. In addition, there is a continuous need to develop light-emitting materials with improved performance, such as improved lifespan characteristics, compared to previously disclosed organic electroluminescent devices.

Korean Patent Publication No. 2019-0113663 (published on October 8, 2019) Korean Patent Publication No. 2015-0036736 (published on April 7, 2015)

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 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 whose lifespan characteristics are significantly improved 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 that the first A plurality of types of host materials, wherein at least one of the host compound and the second host compound contains deuterium; It includes at least one type of first host compound represented by Formula 12 below and at least one type of second host compound represented by Formula 13 below, wherein the first host compound and the second host compound are of multiple types that do not contain deuterium. host material; Alternatively, the present invention was completed by discovering that a compound represented by the following formula (11) achieves the above-mentioned purpose.

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N;

R _a is hydrogen, deuterium, or a carbazole group represented by the following formula 1-1;

Ar ₁ to Ar ₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or a carbazole group represented by the following formula 1-1;

However, at least one of R _a and Ar ₁ to Ar ₃ is a carbazole group represented by the following formula 1-1;

[Formula 1-1]

In Formula 1-1,

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

Any one of R ₅ to R ₈ is connected to L ₁ , R ₁ to R ₄ , and R ₅ to R ₈ not connected to L ₁ are each independently hydrogen, deuterium, substituted or unsubstituted (C1- C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

Ar ₄ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl.

[Formula 2]

In Formula 2,

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

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

X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring.

[Formula 11]

In Formula 11 above,

X' ₁ to X' ₃ are each independently N or CR'_a; However, at least two of X' ₁ to X' ₃ are N;

R' _a is hydrogen or deuterium;

Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl, or are represented by the following formula (A); However, at least one of Ar' ₁ to Ar' ₃ is represented by the following formula (A);

[Formula A]

In Formula A,

L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene;

Cz is substituted or unsubstituted carbazolilene;

L' ₂ is substituted or unsubstituted (C6-C12)arylene;

HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl.

[Formula 12]

In Formula 12 above,

X' ₁ to X' ₃ are each independently N or CH; However, at least two of X' ₁ to X' ₃ are N;

Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with (C6-C30)aryl, or are represented by the following formula (A); However, at least one of Ar' ₁ to Ar' ₃ is represented by the following formula (A);

[Formula A]

In Formula A,

L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene;

Cz is substituted or unsubstituted carbazolilene;

L' ₂ is substituted or unsubstituted (C6-C12)arylene;

HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl.

[Formula 13]

In Formula 13 above,

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

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

X' ₁₁ to X' ₁₄ , X' ₂₃ to X' ₂₆ , and _{X' 15 to} It is substituted or unsubstituted (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring.

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, an organic electroluminescent device exhibiting significantly improved lifespan characteristics compared to a conventional organic electroluminescent device can be manufactured. .

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

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.

The present application includes a first host compound comprising at least one compound represented by Formula 1 and a second host compound comprising one or more compounds represented by Formula 2, and at least one of the first host compound and the second host compound One relates to a plurality of types of host materials containing deuterium, and an organic electroluminescent element containing the host materials. According to one aspect of the present application, the first host compound may not contain deuterium, and the second host compound may contain deuterium. According to another aspect of the present application, both the first host compound and the second host compound may contain deuterium.

The present application relates to an organic electroluminescent compound represented by Formula 11, an organic electroluminescent material containing the same, and an organic electroluminescent device.

The present application includes a plurality of host materials including a first host compound including one or more types of compounds represented by Formula 12 and a second host compound including one or more types of compounds represented by Formula 13, and the host materials. It relates to an organic electroluminescent device. According to one aspect of the present application, the first host compound including the compound represented by Formula 12 and the second host compound including the compound represented by Formula 13 do not contain deuterium.

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” refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, with 3 to 20 carbon atoms being preferred, and 3 to 7 carbon atoms being more preferred. 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, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, di Benzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, Spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyldihydrophenanthrenyl, etc. 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” refers to an aryl group having 3 to 30 ring skeleton atoms and containing one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P. 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, benzofuropyrimidi Nyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzoyl Pyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, Benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, Benzocarbazolyl, dibenzocarbazolyl, phenoxazolyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazoli There are fused ring heteroaryls such as nyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi Nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imy 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 aryl, substituted arylene, substituted heteroaryl, substituted dibenzofuranyl, substituted dibenzothiophenyl, substituted carbazolyl, and substituted carbazolilene. The substituents are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alky Nyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7 membered)heterocycloalkyl, (C6-C30)aryl Substituted or unsubstituted with one or more of oxy, (C6-C30)arylthio, deuterium and (C6-C30)aryl, (3-30 membered)heteroaryl, one or more of deuterium and (3-30 membered)heteroaryl Substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30) Alkyldi(C6-C30)arylsilyl, fused ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, amino, mono- or di- (C1-C30)alkylamino, mono- or di- (C2-C30)alkenylamino, (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, (C1-C30)alkyl (C6-C30)arylamino, mono- or di- (3-30 membered)heteroarylamino, (C1-C30)alkyl (3-30 membered)heteroarylamino, (C2-C30)alkenyl (C6-C30) )Arylamino, (C2-C30)alkenyl (3-30 members)heteroarylamino, (C6-C30)aryl (3-30 members)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30) ) Alkoxycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30) At least one selected from the group consisting of alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl, which are deuterated. Further substitutions may be made. According to one aspect of the present application, the substituents are each independently: deuterium; (C6-C25)aryl substituted or unsubstituted with deuterium; and at least one selected from the group consisting of (5-25 membered) heteroaryl substituted or unsubstituted with deuterium. According to another aspect of the present application, the substituents are each independently deuterium; (C6-C18)aryl substituted or unsubstituted with deuterium; and at least one selected from the group consisting of (5-20 membered) heteroaryl substituted or unsubstituted with deuterium. For example, the substituent may be one or more selected from the group consisting of deuterium, phenyl, naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl, and these substituents 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 and P, preferably one or more heteroatoms selected from N, O and S. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring substituted or unsubstituted with one or more phenyls, a phenanthrene ring, an indole ring, a xanthene ring, etc.

As used herein, heteroaryl and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si, and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 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 compound represented by Formula 1 herein will be described in more detail as follows.

In Formula 1, X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N. According to one aspect of the present application, any two of X ₁ to X ₃ are N, and the other is CR _a . According to another aspect of the present application, X ₁ to X ₃ are all N.

In Formula 1, R _a is hydrogen, deuterium, or a carbazole group represented by Formula 1-1.

In Formula 1, Ar ₁ to Ar ₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or a carbazole group represented by Formula 1-1. According to one aspect of the present application, Ar ₁ to Ar ₃ are each independently a (C6-C25)aryl substituted or unsubstituted with one or more of hydrogen, deuterium, deuterium, and (3-30 membered)heteroaryl, or the above formula It is a carbazole group represented by 1-1. Specifically, (C6-C30)aryl in Ar ₁ to Ar ₃ is each independently phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, triphenylenyl, and phenanthrenyl. or a combination thereof, and the substituent of the substituted (C6-C30)aryl in Ar ₁ to Ar ₃ may be at least one selected from the group consisting of deuterium and (3-30 membered) heteroaryl. For example, Ar ₁ to Ar ₃ may each independently be hydrogen, deuterium, dibenzofuranyl, or dibenzothiophenyl-substituted or unsubstituted phenyl, biphenyl, terphenyl, or quarterphenyl, etc. It can be further replaced with .

In Formula 1, at least one of R _a and Ar ₁ to Ar ₃ is a carbazole group represented by Formula 1-1. According to one aspect of the present application, any one of R _a and Ar ₁ to Ar ₃ is a carbazole group represented by Formula 1-1.

In Formula 1-1, L ₁ is a single bond, or substituted or unsubstituted (C6-C30)arylene. According to one aspect of the present application, L ₁ is a single bond, or (C6-C25)arylene substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. According to another aspect of the present application, L ₁ is a single bond or (C6-C18)arylene substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl. For example, L ₁ may be a single bond, phenylene, or biphenylene substituted or unsubstituted with phenyl, and these may be further substituted with deuterium.

In Formula 1-1, any one of R ₅ to R ₈ is connected to L ₁ , R ₁ to R ₄ , and R ₅ to R ₈ not connected to L ₁ are each independently hydrogen, deuterium, or substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, R ₁ to R ₈ are each independently hydrogen, deuterium, (C6-C25)aryl substituted or unsubstituted with deuterium, or (5-25 membered) heterosubstituted or unsubstituted with deuterium. It's Aril. According to another aspect of the present application, R ₁ to R ₈ are each independently hydrogen, deuterium, (C6-C25)aryl substituted or unsubstituted with deuterium, or (13-membered)heteroaryl substituted or unsubstituted with deuterium. am. For example, R ₁ to R ₈ are each independently hydrogen, deuterium, phenyl, biphenyl, phenanthrenyl, terphenyl, quarterphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dibenzofuranyl, carboxylic acid. It may be zolyl, dibenzothiophenyl, or a combination thereof, and they may be further substituted with deuterium.

In Formula 1-1, Ar ₄ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, Ar ₄ is (C6-C25)aryl substituted or unsubstituted with one or more of deuterium and (3-30 membered) heteroaryl, or (5-25 membered) aryl substituted or unsubstituted by deuterium. It is heteroaryl. According to another aspect of the present application, Ar ₄ is (C6-C18)aryl substituted or unsubstituted with one or more of deuterium and (13-membered) heteroaryl, or (13-membered)heteroaryl substituted or unsubstituted with deuterium. . Specifically, Ar ₄ may be substituted or unsubstituted, phenyl, biphenyl, terphenyl, dibenzofuranyl, or dibenzothiophenyl, and each of these substituents is independently substituted or unsubstituted with deuterium or deuterium. It may be one or more selected from the group consisting of dibenzofuranyl, dibenzothiophenyl substituted or unsubstituted with deuterium, and carbazolyl substituted or unsubstituted with deuterium. For example, Ar ₄ may be phenyl, biphenyl, terphenyl, dibenzofuranyl, or dibenzothiophenyl, substituted or unsubstituted with dibenzofuranyl or dibenzothiophenyl, which may be further substituted with deuterium. there is.

Chemical Formula 1-1 according to an example of the present application may be represented by Chemical Formula A-1 below.

[Formula A-1]

In Formula A-1,

L' ₁ is a single bond or substituted or unsubstituted (C6-C12)arylene;

L' ₂ is substituted or unsubstituted (C6-C12)arylene;

Y is -O-, -S-, or -N(R' ₁ )-;

R' ₁ is substituted or unsubstituted (C6-C12)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl;

R' ₁₁ to R' ₁₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C12)aryl, or substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or It is unsubstituted dibenzothiophenyl;

n is an integer from 1 to 3, m is an integer from 1 to 4;

When m and n are integers of 2 or more, each of R' ₁₁ to R' ₁₄ may be the same or different from each other.

According to one aspect of the present application, the deuterium substitution rate in one compound represented by Formula 1 may be about 30% to about 100%, preferably about 40% to about 100%, and more preferably about 50% to about 50%. It may be about 100%, more preferably about 60% to about 100%. According to another aspect of the present application, Formula 1 may include one or more hydrogen. That is, the deuterium substitution rate in one compound represented by Formula 1 may be about 30% to less than 100%, preferably about 40% to less than 100%, more preferably about 50% to less than 100%, and even more. Preferably, it may be about 60% or more and less than about 100%. The upper limit of the substitution rate may be 100% or less than 100%, for example, about 99%. That is, the compound of Formula 1 may be a compound in which hydrogen is completely or partially replaced with deuterium. The compound of Formula 1 substituted with the deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and an organic electroluminescent device containing the compound can exhibit improved lifespan characteristics.

According to one aspect of the present application, the compound represented by Formula 1 may be one or more selected from the following compounds, but is not limited to these.

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

In Formula 2, A ₁ and A ₂ are each independently substituted or unsubstituted, (C6-C30)aryl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, preferably substituted or unsubstituted. , (C6-C25)aryl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl. According to one aspect of the present application, A ₁ and A ₂ are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, or Fluorenyl, unsubstituted or substituted with one or more of unsubstituted naphthyl, deuterium, (C1-C30)alkyl, and (C6-C30)aryl, deuterium, (C1-C30)alkyl, and (C6-C30)aryl. One or more substituted or unsubstituted benzofluorenyl, triphenylenyl substituted or unsubstituted with deuterium, fluoranthenyl substituted or unsubstituted with deuterium, phenanthrenyl substituted or unsubstituted with deuterium, substituted with deuterium or It may be unsubstituted dibenzofuranyl, carbazolyl substituted or unsubstituted with deuterium, dibenzothiophenyl substituted or unsubstituted with deuterium, or a combination thereof. Specifically, A ₁ and A ₂ are each independently substituted or unsubstituted, phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl, m-terphenyl, o-terphenyl. , naphthyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl. At this time, the substituents of the substituents may be one or more of deuterium, (C6-C30)aryl, and (3-30 membered)heteroaryl, and preferably deuterium, (C6-C18)aryl, and (5-20 membered)heteroaryl. It may be one or more of aryl. For example, A ₁ and A ₂ are each independently phenyl substituted or unsubstituted with one or more of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; naphthyl substituted or unsubstituted with phenyl; p-biphenyl; m-biphenyl; o-biphenyl; o-terphenyl; m-terphenyl; p-terphenyl; triphenylenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; Alternatively, it may be carbazolyl substituted or unsubstituted with one or more of phenyl and naphthyl, which may be further substituted with deuterium.

In Formula 2, any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are connected to each other to form a single bond. X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. According to one aspect of the present application, X ₁₁ to X ₁₄ , X ₂₃ to X ₂₆ , and _{X 15 to} It may be aryl, or substituted or unsubstituted (5-30 membered) heteroaryl. For example, X ₁₁ to X ₁₄ , X ₂₃ to X ₂₆ , and X ₁₅ to X ₂₂ that do not form a single bond may be hydrogen or deuterium. As an example, at least 4 of X ₁₁ to X ₂₆ may be deuterium.

According to one aspect _of the present application, at least one of X ₁₁ , X ₁₈ , X ₁₉ and there is.

According to an example of the present application, in one compound represented by Formula 2, the deuterium substitution rate is about 40% to about 100%, preferably about 50% to about 100%, more preferably about 60% to about 100%. , and even more preferably from about 70% to about 100%. According to another example of the present application, Formula 2 may include one or more deuterium. That is, in one compound represented by Formula 2, the deuterium substitution rate is about 40% to less than 100%, preferably about 50% to less than 100%, more preferably about 60% to less than 100%, and even more preferably is about 70% or more and less than 100%. The upper limit of the substitution rate may be 100% or less than 100%, for example, about 99%. That is, the compound of Formula 2 may be a compound in which hydrogen is completely or partially replaced with deuterium.

According to an example of the present application, the deuterium substitution rate _of X ₁₁ to Typically, it may be about 55% to about 100%. According to another example of the present application, one or more of X ₁₁ to X ₂₆ may be hydrogen. That is, the deuterium substitution rate _of X ₁₁ to It may be less than 100%. The upper limit of the substitution rate may be 100% or less than 100%, for example, about 99%.

The compound of Formula 2 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy due to deuteration, and an organic electroluminescent device containing the compound can exhibit improved lifespan characteristics.

Formula 2 according to an example of the present application may be represented by any one of the following Formulas 2-1 to 2-8.

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

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

[Formula 2-5] [Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Formulas 2-1 to 2-8, A ₁ , A ₂ and X ₁₁ to X ₂₆ are as defined in Formula 2.

According to one aspect of the present application, the compound represented by Formula 2 may be one or more selected from the following compounds, but is not limited to these.

In the above compounds, Dn means that n hydrogens are replaced with deuterium.

According to another embodiment of the present invention, the present application provides an organic electroluminescent compound represented by Formula 11. The compound represented by Formula 11 herein will be described in more detail as follows.

In Formula 11, X' ₁ to X' ₃ are each independently N or CR'_a; However, at least two of X' ₁ to X' ₃ are N. According to one aspect of the present application, any two of X' ₁ to X' ₃ are N, and the other is CR' _a . According to another aspect of the present application, X' ₁ to X' ₃ are all N. R' _a is hydrogen or deuterium.

In Formula 11, Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl, or are represented by Formula A; However, at least one of Ar' ₁ to Ar' ₃ is represented by the above formula (A). According to one aspect of the present application, Ar' ₁ to Ar' ₃ are each independently (C6-C18)aryl substituted or unsubstituted with deuterium, or are represented by Formula A above. According to another aspect of the present application, any one of Ar' ₁ to Ar' ₃ is represented by the above formula (A). For example, Ar' ₁ to Ar' ₃ may each independently be represented by Formula A above, or may be phenyl, biphenyl, or terphenyl, and these may be further substituted with deuterium.

In Formula A, L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene. For example, L' ₁ may be a single bond.

In Formula A, Cz is substituted or unsubstituted carbazolilene. According to one aspect of the present application, Cz is carbazolilene substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. For example, Cz is carbazolilene substituted or unsubstituted with one or more of deuterium and phenyl.

In Formula A, L' ₂ is substituted or unsubstituted (C6-C12)arylene. According to one aspect of the present application, L' ₂ is (C6-C12)arylene substituted or unsubstituted with deuterium. For example, L' ₂ may be phenylene unsubstituted or substituted with deuterium.

In Formula A, HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl. For example, HAr can be dibenzofuranyl or dibenzothiophenyl, which can be further substituted with deuterium.

According to one aspect of the present application, Chemical Formula A of the present application may be represented by the following Chemical Formula A-1.

[Formula A-1]

In Formula A-1, the definitions and preferred embodiments of L' ₁ and L' ₂ are the same as in Formula A.

In Formula A-1, Y is -O-, -S-, or -N(R' ₁ )-. For example, Y is -O- or -S-.

In Formula A-1, R' ₁ is substituted or unsubstituted (C6-C12)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzo. It is thiophenyl.

In Formula A-1, R' ₁₁ to R' ₁₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C12)aryl, or substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted. carbazolyl, or substituted or unsubstituted dibenzothiophenyl. According to one aspect of the present application, R' ₁₁ to R' ₁₄ are each independently hydrogen, deuterium, or (C6-C12)aryl substituted or unsubstituted with deuterium. For example, R' ₁₁ to R' ₁₄ may each independently be hydrogen, deuterium, or phenyl unsubstituted or substituted with deuterium.

In Formula A-1, n is each independently an integer of 1 to 3, m is each independently an integer of 1 to 4, and each of R' ₁₁ to R' ₁₄ may be the same or different from each other. .

According to one aspect of the present application, the compound represented by Formula 11 is the compound C-51 to C-65, C-67 to C-85, C-87 to C-150, C-196 to C-200, and It may be selected from the group consisting of C-226 to C-236, but is not limited to these.

According to another embodiment of the present invention, the present application is a plurality 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 Formula 12 of the present application and , the second host compound is represented by Formula 13 of the present application, and the first host compound and the second host compound do not contain deuterium.

The compound represented by Formula 12 herein will be described in more detail as follows.

In Formula 12, X' ₁ to X' ₃ are each independently N or CH; However, at least two of X' ₁ to X' ₃ are N. According to one aspect of the present application, X' ₁ to X' ₃ are all N.

In Formula 12, Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with (C6-C30)aryl, or are represented by Formula A; However, at least one of Ar' ₁ to Ar' ₃ is represented by the above formula (A). According to one aspect of the present application, Ar' ₁ to Ar' ₃ are each independently unsubstituted (C6-C18)aryl or represented by Formula A above. According to another aspect of the present application, any one of Ar' ₁ to Ar' ₃ is represented by the above formula (A). For example, Ar' ₁ to Ar' ₃ may each independently be represented by Formula A above, or may be phenyl, biphenyl, or terphenyl.

In Formula A, L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene. For example, L' ₁ may be a single bond.

In Formula A, Cz is substituted or unsubstituted carbazolilene. According to one aspect of the present application, Cz is carbazolilene substituted or unsubstituted with one or more of (C6-C30)aryl. For example, Cz is carbazolilene substituted or unsubstituted with phenyl.

In Formula A, L' ₂ is substituted or unsubstituted (C6-C12)arylene. According to one aspect of the present application, L' ₂ is unsubstituted (C6-C12)arylene. For example, L' ₂ may be unsubstituted phenylene.

In Formula A, HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl. For example, HAr can be unsubstituted dibenzofuranyl or unsubstituted dibenzothiophenyl.

According to one aspect of the present application, the compound represented by Formula 12 is the compound C-51 to C-65, C-67 to C-85, C-87 to C-130, C-196 to C-200, and It may be selected from the group consisting of C-227 to C-236, but is not limited to these.

A more detailed description of the compound represented by Formula 13 herein is as follows.

In Formula 13, A' ₁ and A' ₂ are each independently substituted or unsubstituted, (C6-C30)aryl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and are preferably substituted or It may be unsubstituted, (C6-C25)aryl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl. Specifically, A' ₁ and A' ₂ are each independently, substituted or unsubstituted, phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl, m-terphenyl, o- It may be terphenyl, naphthyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, phenanthrenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl. At this time, the substituents of the above substituents may be one or more of (C6-C30)aryl and (3-30 membered)heteroaryl, preferably one or more of (C6-C18)aryl and (5-20 membered)heteroaryl. . For example, A' ₁ and A' ₂ are each independently phenyl unsubstituted or substituted with one or more of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; naphthyl substituted or unsubstituted with phenyl; p-biphenyl; m-biphenyl; o-biphenyl; o-terphenyl; m-terphenyl; p-terphenyl; triphenylenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; Alternatively, it may be carbazolyl substituted or unsubstituted with one or more of phenyl and naphthyl.

In Formula 13, any one of X' ₁₅ to X' ₁₈ and any one of X' ₁₉ to X' ₂₂ are connected to each other to form a single bond. X' ₁₁ to X' ₁₄ , X' ₂₃ to X' ₂₆ , and _{X' 15 to} It is substituted or unsubstituted (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. According to one aspect of the present application, X' ₁₁ to X' ₁₄ , X' _{23 to} X' ₂₆ , and X' ₁₅ to It may be C6-C30)aryl, or substituted or unsubstituted (5-30 membered)heteroaryl. For example, X' ₁₁ to X' ₁₄ , X' ₂₃ to X' ₂₆ , and X' ₁₅ to X' ₂₂ that do not form a single bond may be hydrogen.

According to one aspect of the present application, the compound represented by Formula 13 may be one or more selected from the group consisting of compounds H2-146 to H2-290, but is not limited thereto.

According to another embodiment of the present invention, the present disclosure provides three or more types of host materials including one or more first host compounds and one or more second host compounds. The structural skeletons of the first host compound and the second host compound are the same, but the number of hydrogens and the number of deuteriums in each compound are different.

According to one aspect of the present application, the first host compound may not contain deuterium, and the second host compound may contain deuterium.

According to one aspect of the present application, the skeletons of the first host compound and the second host compound are represented by Formula 2.

According to one aspect of the present application, the plurality of host materials further include a third host compound, and the third host compound is represented by the following formula 1-11.

[Formula 1-11]

In Formula 1-11,

X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N;

R _a is hydrogen or deuterium,

Ar ₁ to Ar ₃ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl.

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

An organic electroluminescent device according to one embodiment includes a first electrode; second electrode; and at least one light-emitting layer interposed between the first electrode and the second electrode, wherein at least one layer of the light-emitting layer includes the plurality of host materials of the present application.

According to one aspect of the present application, the plurality of host materials of the present application include one or more first host compounds represented by Formula 1, and one or more second host compounds represented by Formula 2, for example, It contains at least one compound from C-1 to C-236 as a first host compound and at least one compound from H2-1 to H2-290 as a second host compound, and these plural types of host materials are formed in the same organic layer. , for example, may be included in a light-emitting layer, or may be included in different light-emitting layers.

According to one aspect of the present application, the plurality of host materials of the present application include one or more first host compounds represented by Formula 12, and one or more second host compounds represented by Formula 13, for example, 1 At least one compound among host compounds C-51 to C-65, C-67 to C-85, C-87 to C-130, C-196 to C-200, and C-227 to C-236 and at least one compound from H2-146 to H2-290, which is a second host compound, and these plural types of host materials may be included in the same organic layer, for example, a light-emitting layer, or may be included in different light-emitting layers. there is.

According to another example, the present disclosure may include the organic electroluminescent compound represented by Formula 11 as a host material, electron transport layer material, or electron buffer layer material in the light emitting layer.

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).

One of the first electrode and the second electrode may be a positive electrode (anode) and the other may be a negative electrode (cathode). At this time, the first electrode and the second electrode 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.

Compounds represented by Formula 1, 11 or 12 herein can be prepared by synthetic methods known to those skilled in the art, for example, by referring to Schemes 1-1 to 1-3 below, but are not limited thereto. .

[Reaction Scheme 1-1]

[Scheme 1-2]

[Scheme 1-3]

_{In Schemes 1-1} to _{1-3 , X 1 to}

Compounds represented by Formula 2 or 13 according to the present application can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 2 can be prepared by referring to Scheme 2 below, but is not limited thereto.

[Scheme 2]

In Scheme 2, A _{1 ,} A ₂ , and X ₁₁ to The maximum number is set as the upper limit.

Exemplary synthesis examples of compounds represented by Formulas 1, 2, 11, 12 or 13 have been described above, but these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, and Miyaura borylation reaction. , 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- It is based on a mediated reductive cyclization reaction, etc., and those skilled in the art will easily understand that the reaction proceeds even if other substituents defined in Formula 1, 2, 11, 12, or 13 are combined in addition to the substituents specified in the specific synthesis example.

Additionally, deuterated compounds of formulas 1, 2 and 11 can be prepared in a similar manner using deuterated precursor materials or, more generally, in the presence of a Lewis acid H/D exchange catalyst such as aluminum trichloride or ethyl aluminum chloride. It can be prepared by treating a non-deuterated compound with a deuterated solvent, D6-benzene. Additionally, the degree of deuteration can be controlled by varying reaction conditions such as reaction temperature. For example, the number of deuteriums in Formulas 1, 2, and 11 can be adjusted by adjusting the reaction temperature and time, acid equivalent, etc.

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 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 a plurality of host materials according to the present application for a detailed understanding of the present application, and the present application is not limited to the examples below.

[Example 1] Preparation of compound C-52

Compound 1-1 (7.0 g, 13.07 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.8 g, 14.38 mmol), and tetrakis(triphenylphosphine)palladium in a flask. (0) (0.5 g, 0.39 mmol), potassium carbonate (4.5 g, 32.68 mmol), 65 mL of toluene, 16 mL of ethanol, and 16 mL of distilled water were added and dissolved, and then refluxed and stirred at 120°C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and separated by column chromatography to obtain compound C-52 (3.2 g, yield: 38%).

[Example 2] Preparation of compound C-112

Compound 1-1 (4.6 g, 8.59 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.3) in a flask g, 9.45 mmol), tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.26 mmol), potassium carbonate (3.0 g, 21.48 mmol), 43 mL of toluene, 10 mL of ethanol, and 10 mL of distilled water. After dissolving, it was refluxed and stirred at 120°C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and separated by column chromatography to obtain compound C-112 (2.0 g, yield: 33%).

[Example 3] Preparation of Compound C-2

2-Chloro-4,6-diphenyl-1,3,5-triazine (15 g, 56.0 mmol), (9-phenyl-9H-carbazol-2-yl)boronic acid (19.3 g, 19.3 mmol) was added to the flask. mmol), tetrakis(triphenylphosphine)palladium(0) (3.2 g, 2.8 mmol), potassium carbonate (19.4 g, 140.0 mmol), 260 mL of toluene, 65 mL of ethanol, and 65 mL of water were added and incubated at 120°C. Stirred for 2 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 (13.6 g, yield: 51%).

[Example 4] Preparation of compound C-152

2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10 g, 25.7 mmol) and (9-phenyl-9H-carbazol-2-yl)boron in a flask. Acid (8.9 g, 30.9 mmol), tetrakis(triphenylphosphine)palladium(0) (1.5 g, 1.3 mmol), potassium carbonate (9 g, 64.4 mmol), 130 mL of toluene, 32 mL of ethanol, and 32 mL of water. mL was added and stirred at 120°C for 2 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-152 (7.9 g, yield: 56%).

[Example 5] Preparation of compound C-94

Compound 5-1 (5.9 g, 11.02 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.0 g, 11.02 mmol), and tetrakis(triphenylphosphine)palladium in a flask. (0) (635 mg, 0.55 mmol), potassium carbonate (4.6 g, 33.06 mmol), 55 mL of toluene, 27 mL of ethanol, and 27 mL of distilled water were added and dissolved, and then refluxed and stirred at 120°C for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and separated by column chromatography to obtain compound C-94 (4.7 g, yield: 67%).

[Example 6] Preparation of compound C-62

In a reaction vessel, compound 6-1 (6.0 g, 11.21 mmol), compound 6-2 (3.9 g, 14.57 mmol), tetrakis(triphenylphosphine)palladium (390 mg, 0.34 mmol), potassium carbonate (3.9 g, 28.01 mmol), 56 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-62 (4.9 g, yield: 68%).

[Example 7] Preparation of compound C-226-D17

Compound C-62 was synthesized by selecting deuteration methods disclosed in Korean Patent Publication Nos. 10-2283849 and 10-1427457, and compound C-226-D17 (34 g, yield: 77.2%) was obtained. .

[Example 8] Preparation of compound C-226-D10

In a reaction vessel, compound 8-1 (7.0 g, 13.07 mmol), compound 8-2 (4.4 g, 15.69 mmol), tetrakis(triphenylphosphine)palladium (450 mg, 0.39 mmol), potassium carbonate (4.5 g, 32.68 mmol) mmol), 65 mL of toluene, 16 mL of ethanol, and 16 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-226-D10 (3.3 g, yield: 39%).

[Example 9] Preparation of compound C-227

In a reaction vessel, compound 9-1 (9.5 g, 15.53 mmol), compound 9-2 (5.0 g, 18.64 mmol) , tetrakis(triphenylphosphine)palladium (540 mg, 0.47mmol), potassium carbonate (5.4g, 38.84 mmol), 77 mL of toluene, 19 mL of ethanol, and 19 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-227 (8.5 g, yield: 76%).

[Example 10] Preparation of compound C-228

Compound 10-1 in a reaction vessel (7.0 g, 11.45 mmol), Compound 10-2 ( 3.7 g, 13.74 mmol), tetrakis(triphenylphosphine)palladium (400 mg, 0.34 mmol), potassium carbonate (4.0 g, 28.62 mmol), toluene 57 mL , 14 mL of ethanol, and 14 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-228 (3.0 g, yield: 37%).

[Example 11] Preparation of compound C-229

In a reaction vessel, compound 11-1 (4.3 g, 7.03 mmol), compound 11-2 (2.3 g, 8.44 mmol), tetrakis(triphenylphosphine)palladium (240 mg, 0.21 mmol), potassium carbonate (2.4 g, 17.58 mmol), 35 mL of toluene, 9 mL of ethanol, and 9 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. After purification by column chromatography, compound C-229 was obtained. (2.0 g, yield: 40%) was obtained.

[Example 12] Preparation of compound C-230

In a reaction vessel, compound 12-1 (3.0 g, 5.60 mmol), compound 12-2 (2.5 g, 7.28 mmol), tetrakis(triphenylphosphine)palladium (190 mg, 0.17 mmol), potassium carbonate (1.9 g, 14.01 mmol), 28 mL of toluene, 7 mL of ethanol, and 7 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-230 (2.7 g, yield: 67%).

[Example 13] Preparation of compound C-231

In a reaction vessel, compound 13-1 (4.3 g, 7.03 mmol), compound 13-2 ( 2.3 g, 8.44 mmol), tetrakis(triphenylphosphine)palladium (240 mg, 0.21 mmol), potassium carbonate (2.4 g, 17.58 mmol), 35 mL of toluene, 9 mL of ethanol, and 9 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-231 (2.0 g, yield: 40%).

[Example 14] Preparation of Compound C-91

In a reaction vessel, compound 14-1 (3.9 g, 13.80 mmol), compound 14-2 (5.0 g, 12.66 mmol), palladium acetate (140 mg, 0.63 mmol), 2-dicyclohexylphosphino-2',6' -Dimethoxybiphenyl (520 mg, 1.25 mmol), sodium tert -butoxide (1.8 g, 18.82 mmol), and 62 mL of o-xylene were added, followed by refluxing and stirring for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-91 (6.4 g, yield: 80%).

[Example 15] Preparation of compound C-232

In a reaction vessel, compound 15-1 (3.5 g, 12.64 mmol), compound 15-2 (5.0 g, 10.54 mmol), palladium acetate (240 mg, 1.05 mmol), 2-dicyclohexylphosphino-2',6' -Dimethoxybiphenyl (870 mg, 2.11 mmol), sodium tert -butoxide (2.0 g, 21.07 mmol), and 53 mL of o-xylene were added, followed by refluxing and stirring for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-232 (6.4 g, yield: 80%).

[Example 16] Preparation of compound C-123

In a reaction vessel, compound 16-1 (5 g, 9.34 mmol), compound 16-2 (3.5 g, 10.27 mmol), tetrakis(triphenylphosphine)palladium (320 mg, 0.28 mmol), potassium carbonate (3.2 g, 23.34 mmol), 47 mL of toluene, 12 mL of ethanol, and 12 mL of distilled water were added and stirred at 120°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-123 (3.5 g, yield: 52%).

[Example 17] Preparation of compound C-122

Compound 17-1 (5.0 g, 9.34 mmol), compound 17-2 (3.85 g, 11.2 mmol), tetrakis(triphenylphosphine)palladium (0.32 g, 0.28 mmol), potassium carbonate (3.2 g, 23.35 mmol) in a flask. mmol), 46 mL of toluene, 12 mL of ethanol, and 12 mL of distilled water were added and dissolved, and then refluxed and stirred for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and separated by column chromatography to obtain compound C-122 (3.4 g, yield: 51%).

[Example 18] Preparation of compound C-236

In a reaction vessel, compound 18-1 (4.5 g, 13.07 mmol), compound 18-2 (7 g, 13.07 mmol), tetrakis(triphenylphosphine)palladium (750 mg, 0.653 mmol), potassium carbonate (5.4 g, 39.22 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of distilled water were added, and then refluxed and stirred at 140°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-236 (1.4 g, yield: 14%).

[Example 19] Preparation of compound C-233

In a reaction vessel, compound 19-1 (1.9 g, 7.097 mmol), compound 19-2 (3.8 g, 7.097 mmol), tetrakis(triphenylphosphine)palladium (410 mg, 0.354 mmol), potassium carbonate (3 g, 21.29 mmol), 40 mL of toluene, 10 mL of ethanol, and 10 mL of distilled water were added, and then refluxed and stirred at 140°C for 2 hours. After the reaction was completed, the reaction was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-233 (3 g, yield: 66%).

[Example 20] Preparation of Compound C-93

Compound 20-1 (5 g, 12.55 mmol), Compound 20-2 (3.8 g, 13.80 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.57 g, 0.627 mmol), sodium tert -butoxide ( 60 mL of toluene was added to 1.8 g, 18.82 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.51 g, 1.255 mmol), and then refluxed and stirred at 120°C for 1 hour. . After completion of the reaction, it was cooled to room temperature and then filtered through Celite. Afterwards, it was distilled under reduced pressure and separated by column chromatography to obtain compound C-93 (2 g, yield: 24%).

[Example 21] Preparation of compound C-92

Compound 21-1 (5 g, 12.55 mmol), Compound 21-2 (3.8 g, 13.80 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.57 g, 0.627 mmol), sodium tert -butoxide ( 1.8 g, 18.82 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.51 g, 1.255 mmol) were added with 60 mL of toluene and stirred under reflux at 120°C for 1 hour. After completion of the reaction, it was cooled to room temperature and then filtered through Celite. Afterwards, it was distilled under reduced pressure and separated by column chromatography to obtain compound C-92 (4.4 g, yield: 54%).

[Example 22] Preparation of compound C-234

Compound 22-1 (5 g, 10.53 mmol), Compound 22-2 (3.2 g, 11.59 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.48 g, 0.526 mmol), sodium tert -butoxide ( 55 mL of toluene was added to 1.5 g, 15.80 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.43 g, 1.053 mmol), and then refluxed and stirred at 120°C for 1 hour. After completion of the reaction, it was cooled to room temperature and then filtered through Celite filter. Afterwards, it was distilled under reduced pressure and separated by column chromatography to obtain compound C-234 (4.5 g, yield: 59%).

[Example 23] Preparation of compound C-235

Compound 23-1 (5 g, 10.53 mmol), Compound 23-2 (3.2 g, 11.59 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.48 g, 0.526 mmol), sodium tert -butoxide ( 55 mL of toluene was added to 1.5 g, 15.80 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.43 g, 1.053 mmol), and then refluxed and stirred at 120°C for 1 hour. After completion of the reaction, it was cooled to room temperature and then filtered through Celite. Afterwards, it was distilled under reduced pressure and separated by column chromatography to obtain compound C-235 (4.3 g, yield: 56%).

[Device Examples 1 to 12] Manufacturing of green OLED by depositing multiple types of host materials 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 as a first hole transport layer was deposited to a thickness of 80 nm on the hole injection layer. 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 30 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-130 was placed as a dopant in another cell, and then the two host materials were mixed in 1: The second hole transport layer is evaporated at a rate of 2 (first host: second host) and simultaneously evaporates the dopant material at a different rate to dope the dopant in an amount of 10% by weight based on the total amount of the host and dopant. A 40 nm thick light emitting layer was deposited on top. Next, a 35 nm thick electron transport layer was deposited on the emitting layer by evaporating the compound ETL-1 : EIL-1 as an electron transport material at a weight ratio of 40:60. Next, compound EIL-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] Preparation of OLED containing a comparative compound as a host

An OLED was manufactured in the same manner as Device Example 1, except that each of the first and second host compounds listed in Table 1 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 60,000 nit luminance of the OLEDs manufactured in Device Examples 1 to 12 and Comparative Example 1 based on 1,000 nit luminance decrease from 100% to 80%. (Life: T80) is shown in Table 1 below.

[Table 1]

As shown in Table 1, the organic electroluminescent device (Device Examples 1 to 12) using multiple types of host materials according to the present application is superior to the organic electroluminescent device (Comparative Example 1) including a conventional host combination. It was confirmed that it exhibited longevity characteristics.

The lifespan of green light-emitting organic electroluminescent devices is generally shorter than that of red light-emitting devices. In order to improve the lifespan characteristics of a green light-emitting organic electroluminescent device, a compound into which a deuterated moiety was introduced was used. It is not limited by theory, but when an organic electroluminescent compound is replaced with deuterium, the zero point vibration energy of the compound is lowered and the bond dissociation energy (BDE) in the compound is increased. Stability can be increased.

[Device Examples 13 to 17] Preparation of green OLED by depositing the organic electroluminescent compound according to the present application

An OLED was manufactured in the same manner as Device Example 1, except that the light-emitting layer was deposited as follows. The host compound listed in Table 2 below is placed as a host in a cell in the vacuum evaporation equipment, and compound D-130 is placed as a dopant in another cell. Then, the host and dopant materials are evaporated simultaneously at different rates to form the 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 10% by weight based on the total amount.

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

An OLED was manufactured in the same manner as Device Example 13, except that the host compound listed 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 20,000 nit luminance of the OLEDs manufactured in Device Examples 13 to 17 and Comparative Example 2 based on 1,000 nit luminance fall from 100% to 80%. (Life: T80) is shown in Table 2 below.

[Table 2]

As shown in Table 2, the organic electroluminescent device (Device Examples 13 to 17) using the organic electroluminescent compound according to the present application as a single host material was compared to the organic electroluminescent device (Comparative Example 2) containing a conventional compound. It was confirmed that it showed excellent lifespan characteristics compared to

[Device Examples 18 to 21] Preparation of OLED containing the organic electroluminescent compound according to the present application as a host material

An OLED was manufactured in the same manner as in Device Example 1, except that the compounds listed in Table 3 below were used alone as host materials for the light-emitting layer, and Compound D-150 was used as a dopant.

The driving voltage, luminous efficiency, luminous color based on 1,000 nits luminance of the organic electroluminescent device according to device examples 18 to 21 manufactured as described above, and the time until the light intensity based on 20,000 nit luminance falls from 100% to 80%. (Life: T80) is shown in Table 3 below.

[Table 3]

[Device Examples 22 to 30] Manufacturing of green OLED by depositing multiple types of host materials according to the present application

An OLED was manufactured in the same manner as Device Example 1, except that each of the first and second host compounds shown in Table 4 below was used as the host of the light emitting layer.

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

An OLED was manufactured in the same manner as Device Example 25, except that each of the first and second host compounds listed in Table 4 below was used as the host of the light emitting layer.

As described above, the driving voltage, luminous efficiency, luminance color, and light intensity based on 60,000 nit luminance of the OLEDs manufactured in Device Examples 22 to 30 and Comparative Example 3 based on 1,000 nit luminance decrease from 100% to 80%. (Life: T80) is shown in Table 4 below.

[Table 4]

As shown in Table 4, the organic electroluminescent device (Device Examples 22 to 30) using multiple types of host materials according to the present application is superior to the organic electroluminescent device (Comparative Example 3) including a conventional host combination. It was confirmed that it exhibited longevity characteristics.

[Device Examples 31 to 34] Manufacturing of green OLED by depositing multiple types of host materials according to the present application

An OLED was manufactured in the same manner as Device Example 1, except that each of the first host compound, second host compound, and third host compound (1:1:1) shown in Table 5 below was used as the host of the light emitting layer. did.

The driving voltage, luminous efficiency, luminous color, and light intensity based on 60,000 nit luminance of the organic electroluminescent devices according to device examples 31 to 34 manufactured as described above drop from 100% to 80%. The time (life: T80) is shown in Table 5 below.

[Table 5]

As shown in Table 5 above, an organic electroluminescent device employing a compound of the same structure as one of the host materials of the light-emitting layer, a deuterated compound and a non-deuterated compound, has excellent driving voltage and/or high efficiency and /or has long life characteristics and can be manufactured at relatively reduced manufacturing costs.

Compounds used in the device examples and comparative examples are shown in Table 6 below.

[Table 6]

Claims (26)

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): , a plurality of types of host materials, wherein at least one of the first host compound and the second host compound contains deuterium:
[Formula 1]

In Formula 1,
X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N;
R _a is hydrogen, deuterium, or a carbazole group represented by the following formula 1-1;
Ar ₁ to Ar ₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or a carbazole group represented by the following formula 1-1;
However, at least one of R _a and Ar ₁ to Ar ₃ is a carbazole group represented by the following formula 1-1;
[Formula 1-1]

In Formula 1-1,
L ₁ is a single bond, or substituted or unsubstituted (C6-C30)arylene;
Any one of R ₅ to R ₈ is connected to L ₁ , R ₁ to R ₄ , and R ₅ to R ₈ not connected to L ₁ are each independently hydrogen, deuterium, substituted or unsubstituted (C1- C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
Ar ₄ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
[Formula 2]

In Formula 2,
A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl ego;
Any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are linked to each other to form a single bond;
X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. The method of claim 1, wherein (C6-C30)aryl in Ar ₁ to Ar ₃ of Formula 1 is each independently phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, triphenyl. Phenylenyl, phenanthrenyl, or a combination thereof, and the substituent of the substituted (C6-C30)aryl in Ar ₁ to Ar ₃ is at least one selected from the group consisting of deuterium and (3-30 membered) heteroaryl, Host material for multiple species. The method of claim 1, wherein R ₁ to R ₈ of Formula 1-1 are Each independently, hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, phenanthrenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, Substituted or unsubstituted quaternophenyl, naphthyl substituted or unsubstituted with deuterium, phenylnaphthyl substituted or unsubstituted with deuterium, naphthylphenyl substituted or unsubstituted with deuterium, dibenzofura substituted or unsubstituted with deuterium Multiple types of host materials, which are nyl, carbazolyl substituted or unsubstituted with deuterium, dibenzothiophenyl substituted or unsubstituted with deuterium, or a combination thereof. The method of claim 1, wherein Ar ₄ in Formula 1-1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and the substituents of substituted phenyl, substituted biphenyl, substituted terphenyl, substituted dibenzofuranyl, and substituted dibenzothiophenyl are each independently substituted with deuterium or deuterium. or at least one host material selected from the group consisting of unsubstituted dibenzofuranyl, deuterium-substituted or unsubstituted dibenzothiophenyl, and deuterium-substituted or unsubstituted carbazolyl. The host material according to claim 1, wherein Formula 1-1 is represented by the following Formula A-1:
[Formula A-1]

In Formula A-1,
L' ₁ is a single bond or substituted or unsubstituted (C6-C12)arylene;
L' ₂ is substituted or unsubstituted (C6-C12)arylene;
Y is -O-, -S-, or -N(R' ₁ )-;
R' ₁ is substituted or unsubstituted (C6-C12)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl;
R' ₁₁ to R' ₁₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C12)aryl, or substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or It is unsubstituted dibenzothiophenyl;
n is an integer from 1 to 3, m is an integer from 1 to 4;
When m and n are integers of 2 or more, each of R' ₁₁ to R' ₁₄ may be the same or different from each other. The plurality of host materials according to claim 1, wherein the first host compound does not contain deuterium and the second host compound contains deuterium. The host material according to claim 1, wherein in Formula 1, the deuterium substitution rate is 30% to 100%. The host material according to claim 1, wherein in Formula 2, at least one of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ is deuterium. The host material according to claim 1, wherein in Formula 2, the deuterium substitution rate is 40% to 100%. The host material according to claim 1, wherein in Formula 2, the deuterium substitution rate among X ₁₁ to X ₂₆ is 25% to 100%. The host material according to claim 1, wherein Formula 2 is represented by any one of the following Formulas 2-1 to 2-8:
[Formula 2-1] [Formula 2-2]

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

[Formula 2-5] [Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Formulas 2-1 to 2-8,
A ₁ , A ₂ and X ₁₁ to X ₂₆ are as defined in claim 1. The method of claim 1, wherein A ₁ and A ₂ of Formula 2 are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, Fluorenyl, substituted or unsubstituted with one or more of naphthyl, deuterium, (C1-C30)alkyl and (C6-C30)aryl, deuterium, (C1-C30)alkyl and (C6-C30) substituted or unsubstituted with ) benzofluorenyl substituted or unsubstituted with one or more of aryl, triphenylenyl substituted or unsubstituted with deuterium, fluoranthenyl substituted or unsubstituted with deuterium, phenanthrenyl substituted or unsubstituted with deuterium, Multiple types of host materials, which are dibenzofuranyl substituted or unsubstituted, carbazolyl substituted or unsubstituted with deuterium, dibenzothiophenyl substituted or unsubstituted with deuterium, or a combination thereof. The host material according to claim 1, wherein the compound represented by Formula 1 is one or more selected from 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.

In the above compounds, Dn means that n hydrogens are replaced with deuterium. An organic electroluminescent compound represented by Formula 11:
[Formula 11]

In Formula 11 above,
X' ₁ to X' ₃ are each independently N or CR'_a; However, at least two of X' ₁ to X' ₃ are N;
R' _a is hydrogen or deuterium;
Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl, or are represented by the following formula (A); However, at least one of Ar' ₁ to Ar' ₃ is represented by the following formula (A);
[Formula A]

In Formula A,
L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene;
Cz is substituted or unsubstituted carbazolilene;
L' ₂ is substituted or unsubstituted (C6-C12)arylene;
HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl. The organic electroluminescent compound according to claim 15, wherein the formula A is represented by the following formula A-1.
[Formula A-1]

In Formula A-1,
L' ₁ and L' ₂ are as defined in clause 15;
Y is -O-, -S-, or -N(R' ₁ )-;
R' ₁ is substituted or unsubstituted (C6-C12)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl;
R' ₁₁ to R' ₁₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C12)aryl, or substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or It is unsubstituted dibenzothiophenyl;
n is an integer from 1 to 3, m is an integer from 1 to 4;
When m and n are integers of 2 or more, each of R' ₁₁ to R' ₁₄ may be the same or different from each other. The organic electroluminescent compound according to claim 15, wherein the compound represented by Formula 11 is selected from the following compounds.

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 (12), and the second host compound is represented by the following formula (13): , wherein the first host compound and the second host compound do not contain deuterium:
[Formula 12]

In Formula 12 above,
X' ₁ to X' ₃ are each independently N or CH; However, at least two of X' ₁ to X' ₃ are N;
Ar' ₁ to Ar' ₃ are each independently (C6-C30)aryl substituted or unsubstituted with (C6-C30)aryl, or are represented by the following formula (A); However, at least one of Ar' ₁ to Ar' ₃ is represented by the following formula (A);
[Formula A]

In Formula A,
L' ₁ is a single bond, or substituted or unsubstituted (C6-C12)arylene;
Cz is substituted or unsubstituted carbazolilene;
L' ₂ is substituted or unsubstituted (C6-C12)arylene;
HAr is substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl;
[Formula 13]

In Formula 13 above,
A' ₁ and A' ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;
Any one of X' ₁₅ to X' ₁₈ and any one of X' ₁₉ to X' ₂₂ are linked to each other to form a single bond;
X' ₁₁ to X' ₁₄ , X' ₂₃ to X' ₂₆ , and _{X' 15 to} It is substituted or unsubstituted (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. The host material according to claim 18, wherein the compound represented by Formula 13 is one or more selected from the following compounds.

first electrode; second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein at least one layer of the light-emitting layer includes the plurality of host materials according to claim 1. first electrode; second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein at least one layer of the light-emitting layer includes the organic electroluminescent compound according to claim 15. first electrode; second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein at least one layer of the light-emitting layer includes the plurality of host materials according to claim 18. Three or more host materials including one or more first host compounds and one or more second host compounds, wherein the structural skeleton of the first host compound and the second host compound is the same, but the number of hydrogens and deuteriums of each compound is the same. Host material of multiple species, different from each other. The plurality of host materials according to claim 23, wherein the first host compound does not contain deuterium and the second host compound contains deuterium. The plurality of host materials according to claim 24, wherein the skeletons of the first host compound and the second host compound are represented by the following formula (2):
[Formula 2]

In Formula 2,
A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl ego;
Any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are linked to each other to form a single bond;
X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. The plurality of host materials according to claim 23, wherein the plurality of host materials further include a third host compound, and the third host compound is represented by the following formula 1-11:
[Formula 1-11]

In Formula 1-11,
X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N;
R _a is hydrogen or deuterium,
Ar ₁ to Ar ₃ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl.

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