KR20240029635A - 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 driving voltage, luminous efficiency, and/or lifespan characteristics compared to the organic electroluminescent device.

Description

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

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

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

Various materials or concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, driving voltage, and/or lifespan, but have not been satisfactory for practical use. In addition, there is a continuous need to develop organic electroluminescent materials with improved performance, such as improved driving voltage, luminous efficiency, power efficiency and/or lifetime characteristics compared to combinations of previously disclosed specific compounds.

Meanwhile, Japanese Patent Laid-Open No. 2021-66689 discloses a triazine compound containing a germanium element and an organic electroluminescent device containing the same, but a plurality of types of host materials containing a specific combination of compounds claimed herein, and organic electroluminescent compounds are not specifically disclosed. Accordingly, there is a continuous need to develop light-emitting materials with improved performance, such as improved driving voltage, luminous efficiency and/or lifespan characteristics, compared to combinations of previously disclosed specific compounds.

Japanese Patent Publication No. 2021-66689 (published on April 30, 2021)

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

As a result of intensive research to solve the above technical problems, the present inventors have developed a plurality of host materials including one or more first host compounds and one or more second host compounds, wherein the first host compound has the following formula (1) and the second host compound is represented by the following formula (2): a plurality of host materials; Alternatively, the present invention was completed by discovering that a compound represented by the following formula (1') achieves the above-mentioned purpose.

[Formula 1]

In Formula 1,

X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N;

R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

L ₁ to L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

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

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

R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl;

q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other.

[Formula 2]

In Formula 2,

L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

Ar ₄ to Ar ₆ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl, or two adjacent ones of Ar ₄ to Ar ₆ are linked and substituted. Alternatively, it may form an unsubstituted carbazole ring.

[Formula 1']

In Formula 1',

X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N;

R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

L ₁ to L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;

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

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

R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl;

q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other;

However, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, among Ar ₁ and Ar ₂ At least one is substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted fluorenyl, phenyl substituted with fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted Naphthylphenyl, substituted or unsubstituted phenylnaphthyl, or substituted or unsubstituted terphenyl.

By including a specific combination of the compounds according to the present disclosure as a plurality of host materials, or by including the compounds according to the present disclosure, organic electroluminescent devices have low driving voltage, high luminous efficiency, and/or excellent lifespan characteristics compared to conventional organic electroluminescent devices. An electroluminescent device is provided, and it is possible to manufacture a display device or lighting device using the same.

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 to limit the scope of the present application.

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

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

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

As used herein, “(C1-C30)alkyl(lene)” refers to a straight or branched chain alkyl(lene) having 1 to 30 carbon atoms in the chain, where 1 to 10 carbon atoms are preferred. , it is more preferable to have 1 to 6 pieces. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl, etc. As used herein, “(C3-C30)cycloalkyl(lene)” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, where 3 to 20 carbon atoms are preferred, and 3 to 7 carbon atoms are more preferred. desirable. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, "(3-7 membered) heterocycloalkyl" has 3 to 7 ring skeleton atoms and is one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, Te and Ge, Preferably, it refers to cycloalkyl containing one or more heteroatoms selected from O, S, and N, and examples include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran. 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, quinquiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, and benzofluore. Nyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluorane thenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, spiro[cyclopentene-fluorene]yl, spiro[dihydroinden-fluorene]yl, azulenyl, tetramethyldihydrophenanthre Neil, 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 (len)" has 3 to 30 ring atoms and is one or more heteroaryls selected from the group consisting of B, N, O, S, Si, P, Se, Te and Ge. It refers to an aryl group containing atoms. 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 (lene) herein includes forms in which one or more heteroaryl or aryl groups are connected to a heteroaryl (lene) 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, naphthooxazolyl, benzofuroquinolyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzopuropyrimidi Nyl, naphthofuropyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoin doli, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothia Zolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, Quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazole, phenazinyl, imidazopyridyl. , fused ring heteroaryls such as chromenoquinazolinyl, thiochromenoquinazolinyl, 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-imi Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1 -Isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl Nolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8- Isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7 -yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7 -phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-arc Lidinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole- 1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3 -Methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl , 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho- [1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho -[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naph to-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1- Naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4 -naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl , 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuran 1, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzo furanyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]- Benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b] -benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b ]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2- b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2 -b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2, 3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2 ,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[ 2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho- [2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho -[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3, 2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl midinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9- Benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2- d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzo Thio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d] Pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-ger Mafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. As used herein, “halogen” includes F, Cl, Br and I atoms.

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

As used herein, “ring formed by linking adjacent substituents” refers to a substituted or unsubstituted (3-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring formed by linking or fusion of two or more adjacent substituents. means. The ring may preferably be a substituted or unsubstituted (3-26 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. 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, cyclopentane ring, indane ring, fluorene ring, phenanthrene ring, indole ring, benzofuran ring, benzothiophene ring, carbazole ring, or xanthene ring.

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. As used herein, the substituents of substituted alkyl(len), substituted aryl(len), substituted heteroaryl(len), substituted cycloalkyl(lene), substituted heterocycloalkyl, and substituted carbazole rings are each independently As, deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl; (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, (C1-C30)alkyl, (C6-C30)aryl, and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently: deuterium; (C1-C10)alkyl; (6-20 membered)heteroaryl substituted or unsubstituted with (C6-C18)aryl; (C6-C28)aryl substituted or unsubstituted with one or more of (C6-C25)aryl and (6-20 membered)heteroaryl; (C3-C12)cycloalkyl; and di(C6-C15)arylamino, and may be further substituted with deuterium. According to another aspect of the present application, the substituents are each independently deuterium; (C1-C6)alkyl; (6-15 membered)heteroaryl substituted or unsubstituted with (C6-C12)aryl; (C6-C20)aryl substituted or unsubstituted with one or more of (C6-C20)aryl and (6-15 membered)heteroaryl; (C3-C8)cycloalkyl; and di(C6-C12)arylamino, and may be further substituted with deuterium. For example, the substituents are each independently deuterium; methyl; tert -butyl; Phenyl unsubstituted or substituted with one or more of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; Biphenyl; naphthyl substituted or unsubstituted with phenyl; triphenylenyl; phenanthrenyl; pyridyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; carbazolyl substituted or unsubstituted with one or more of phenyl, biphenyl and naphthyl; cyclohexyl; and diphenylamino, which may be further substituted with deuterium.

The present application is a plurality of host materials comprising at least one type of first host compound and at least one type of second host compound, wherein the first host compound is represented by the following formula (1), and the second host compound is represented by the following formula (2) Provided are multiple types of host materials that are displayed.

A more detailed description of the compound represented by Formula 1 is as follows.

In Formula 1, X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N. According to one aspect of the present application, at least two of X ₁ to X ₃ may be N, or all of X ₁ to X ₃ may be N.

Wherein R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or It is a substituted or unsubstituted (3-30 membered) heteroaryl. For example, R ₀ may each independently be hydrogen.

In Formula 1, L ₁ to L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted ( 3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to one aspect of the present application, L ₁ to L ₃ are each independently a single bond, (C6-C18)arylene substituted or unsubstituted with (C6-C18)aryl, or unsubstituted with (C6-C18)aryl. It may be (6-20 won) heteroarylene. According to another aspect of the present application, L ₁ to L ₃ are each independently a single bond, (C6-C10)arylene substituted or unsubstituted (C6-C15)arylene, or (C6-C10)aryl. Or it may be unsubstituted (6-15 membered) heteroarylene. For example, L ₁ to L ₃ may each independently be a single bond, phenylene substituted or unsubstituted with phenyl, biphenylene, naphthylene, or carbazolilene substituted or unsubstituted with phenyl.

In Formula 1, L' is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene. According to one aspect of the present application, L' is (C6-C18)arylene substituted or unsubstituted with one or more of (C1-C10)alkyl and (C6-C18)aryl, or (C6-C18)aryl. It may be unsubstituted (6-20 membered) heteroarylene. According to another aspect of the present application, L' is (C6-C15)arylene substituted or unsubstituted with one or more of (C1-C6)alkyl and (C6-C12)aryl, or (C6-C10)aryl. Or it may be unsubstituted (6-15 membered) heteroarylene. For example, L' is phenylene substituted or unsubstituted with phenyl, biphenylene, dimethylfluorenylene, dibenzofuranylene, dibenzothiophenylene, carbazolilene substituted or unsubstituted with phenyl, or It may be benzoselenophenylene.

In Formula 1, Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, Ar ₁ and Ar ₂ are each independently, (C6-C28)aryl substituted or unsubstituted with one or more of (C1-C10)alkyl and (C6-C20)aryl, or (C6- It may be a (6-25 membered) heteroaryl substituted or unsubstituted with C18)aryl. According to another aspect of the present application, Ar ₁ and Ar ₂ are each independently, (C6-C25)aryl substituted or unsubstituted with one or more of (C1-C6)alkyl and (C6-C12)aryl, or (C6) -C12) It may be substituted or unsubstituted (6-20 membered) heteroaryl. For example, Ar ₁ and Ar ₂ are each independently phenyl, naphthylphenyl, phenylnaphthyl, biphethyl, terphenyl, naphthyl, phenanthrenyl, triphenylenyl, fluoranthenyl, chrysenyl, dimethylfluor Orenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl substituted or unsubstituted with phenyl, dibenzoselenophenyl, indolocarbazolyl substituted with phenyl, Or it may be benzofurocarbazolyl, etc.

In Formula 1, R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 members) ) Heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl. According to one aspect of the present application, R ₁ to R ₃ may each independently be substituted or unsubstituted (C6-C18)aryl. According to another aspect of the present application, R ₁ to R ₃ may each independently be unsubstituted (C6-C12)aryl. For example, R ₁ to R ₃ may each independently be phenyl.

In Formula 1, q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other.

According to one aspect of the present application, Formula 1 may be represented by one or more of the following Formulas 1-1 to 1-6.

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

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

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

In Formulas 1-1 and 1-4, X is -O-, -S-, -Se-, -N(R ₃₁ )-, or -C(R ₃₂ )(R ₃₃ )-.

R ₃₁ to R ₃₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 members) It may be heteroaryl, or adjacent substituents may be connected to each other to form a ring. According to one aspect of the present application, R ₃₁ to R ₃₃ may each independently be hydrogen, unsubstituted (C1-C10)alkyl, or unsubstituted (C6-C18)aryl. According to another aspect of the present application, R ₃₁ to R ₃₃ may each independently be hydrogen, unsubstituted (C1-C6)alkyl, or unsubstituted (C6-C12)aryl. For example, R ₃₁ to R ₃₃ may each independently be methyl or phenyl.

In Formulas 1-1 to 1-6, R ₁₂ to R ₁₅ are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6- C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri( C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted Ringed tri(C6-C30)arylsilyl, fused ring group of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(R')(R") or; may be connected to an adjacent substituent to form a ring. According to one aspect of the present application, R ₁₂ to R ₁₅ are each independently hydrogen, substituted or unsubstituted (C1-C10)alkyl, or substituted or unsubstituted It may be a (C6-C18)aryl. According to one aspect of the present application, R ₁₂ to R ₁₅ may each independently be hydrogen, or a substituted or unsubstituted (C6-C12)aryl. Other aspects of the present application According to an embodiment, R ₁₂ to R ₁₅ may each independently be hydrogen or unsubstituted (C6-C12)aryl. For example, R ₁₂ to R ₁₅ may each independently be hydrogen or phenyl. .

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

In Formulas 1-1 to 1-6, m to o are each independently an integer of 1 to 3, and p are each independently an integer of 1 to 4; When m to p are integers of 2 or more, each of R ₁₂ to R ₁₅ may be the same or different from each other.

In Formulas _1-1 to _1-6 , Ar ₁ , Ar _{2 ,} L ₁ to L ₃ , L', R ₁ to R ₃ , and q are the same as defined in Formula 1.

According to one aspect of the present application, at least one of Ar ₁ and Ar ₂ may be of the following formula 1-1-1 or 1-1-2.

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

In Formula 1-1-1, X' is -O-, -S-, -Se-, -N(R ₃₄ )-, or -(CR ₃₅ )(R ₃₆ )-.

R ₃₄ to R ₃₆ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 members) It may be heteroaryl, or adjacent substituents may be connected to each other to form a ring. According to one aspect of the present application, R ₃₄ to R ₃₆ are each independently hydrogen, unsubstituted (C1-C10)alkyl, or unsubstituted (C6-C18)aryl, or are connected to an adjacent substituent to form (6-30) circle) may form a monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. According to another aspect of the present application, R ₃₄ to R ₃₆ are each independently hydrogen, unsubstituted (C1-C6)alkyl, or unsubstituted (C6-C12)aryl, or are connected to an adjacent substituent to form (6- It can form a 15-membered aromatic ring. For example, R ₃₄ to R ₃₆ may each independently be methyl or phenyl, or R ₃₅ and R ₃₆ may be connected to each other to form a spirofluorene ring.

In the above formulas 1-1-1 and 1-1-2, R ₄ to R ₇ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted Substituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl. , substituted or unsubstituted tri(C6-C30)arylsilyl, fused ring group of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(R') (R"); or may be connected to an adjacent substituent to form a ring. According to one aspect of the present application, R ₄ to R ₇ are each independently hydrogen, or substituted or unsubstituted (C6-C12)aryl. , may be connected to adjacent substituents to form a (6-30 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. According to another aspect of the present application, R ₄ to R ₇ are each independently It may be hydrogen, or unsubstituted (C6-C12)aryl, or may be connected to an adjacent substituent to form a (6-13 membered) aromatic ring. For example, R ₄ to R ₇ are each independently, It may be hydrogen or phenyl, or may be connected to an adjacent substituent to form an indole ring substituted with phenyl, or a benzofuran ring.

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

In the above formulas 1-1-1 and 1-1-2, a is an integer of 1 to 3, b to d are each independently an integer of 1 to 4, and when a to d are an integer of 2 or more, each R ₄ to R ₇ may be the same or different from each other.

In Formulas 1-1-1 and 1-1-2, * represents the bonding position with L ₁ or L ₂ .

According to one aspect of the present application, at least one of Ar ₁ and Ar ₂ may have the formula 1-1-1, and at least one of Ar ₁ and Ar ₂ may have the formula 1-1-2. According to another aspect of the present application, either Ar ₁ or Ar ₂ may have the formula 1-1-1 or 1-1-2.

A more detailed description of the compound represented by Formula 2 is as follows.

In Formula 2, L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted ( 3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30) cycloalkylene. According to one aspect of the present application, L ₄ to L ₆ are each independently a single bond, (C6-C18)arylene substituted or unsubstituted with deuterium, or (6-20 membered) heterosubstituted or unsubstituted with deuterium. It may be arylene. According to another aspect of the present application, L ₄ to L ₆ are each independently a single bond, (C6-C15)arylene substituted or unsubstituted with deuterium, or (6-15 members) substituted or unsubstituted with deuterium. It may be heteroarylene. For example, L ₄ to L ₆ may each independently be a single bond, phenylene, naphthylene, biphenylene, dibenzofuranylene, dibenzothiophenylene, or carbazolilene, which are further substituted with deuterium. It can be.

In Formula 2, Ar ₄ to Ar ₆ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl, or two adjacent ones of Ar ₄ to Ar ₆ may be connected to each other to form a substituted or unsubstituted carbazole ring. According to one aspect of the present application, Ar ₄ to Ar ₆ are each independently selected from deuterium, (C1-C10)alkyl, (C6-C25)aryl, (6-20 membered)heteroaryl, (C6-C15)cycloalkyl, and (C6-C30)aryl substituted or unsubstituted with one or more of di(C6-C15)arylamino; or (6-30 membered) heteroaryl substituted or unsubstituted with one or more of deuterium, (C6-C18)aryl, and (6-15 membered) heteroaryl, or two adjacent ones of Ar ₄ to Ar ₆ are linked and substituted. Alternatively, it may form an unsubstituted carbazole ring, and the substituent of the substituted carbazole ring is deuterium; (C6-C25)aryl substituted or unsubstituted with one or more of deuterium, (C6-C25)aryl, and (6-20 membered)heteroaryl; and (6-20 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C15)aryl. According to another aspect of the present application, Ar ₄ to Ar ₆ are each independently selected from deuterium, (C1-C6)alkyl, (C6-C20)aryl, (6-15 membered)heteroaryl, (C6-C10)cycloalkyl. and (C6-C27)aryl substituted or unsubstituted with one or more of di(C6-C12)arylamino; or (6-20 membered) heteroaryl substituted or unsubstituted with one or more of deuterium, (C6-C15)aryl, and (6-13 membered) heteroaryl, or two adjacent ones of Ar ₄ to Ar ₆ are linked and substituted. Alternatively, it may form an unsubstituted carbazolyl ring, and the substituent of substituted carbazolyl is deuterium; (C6-C20)aryl substituted or unsubstituted with one or more of deuterium, (C6-C20)aryl, and (6-15 membered)heteroaryl; and (6-15 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C12)aryl. For example, Ar ₄ to Ar ₆ are each independently substituted or provided with one or more of methyl, tert -butyl, naphthyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, cyclohexyl, and diphenylamino. Ringed phenyl; Biphenyl; terphenyl; Naphthyl substituted or unsubstituted with phenyl; triphenylenyl; phenanthrenyl; anthracenyl; fluoranthenyl; dimethylfluorenyl; dimethylbenzofluorenyl; phenylfluorenyl; diphenylfluorenyl; spirobifluorenyl; (C22)aryl; Pyridyl substituted with phenyl; benzothiophenyl; benzimidazole substituted with phenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; carbazolyl substituted or unsubstituted with one or more of phenyl, naphthyl, and biphenyl; benzocarbazolyl; fenoxazinil; Phenantrooxazolyl substituted or unsubstituted with one or more of phenyl, biphenyl, and pyridyl; Phenanthrothiazolyl substituted or unsubstituted with one or more of phenyl and biphenyl; benzonaphthofuranyl; or benzonaphthothiophenyl, which may be further substituted with deuterium; Two adjacent ones of Ar ₄ to Ar ₆ may be connected to each other to form a substituted or unsubstituted carbazolyl ring, and the substituent of the substituted carbazolyl is deuterium; Phenyl unsubstituted or substituted with one or more of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; Biphenyl; terphenyl; naphthyl substituted or unsubstituted with phenyl; triphenylenyl; phenanthrenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; and carbazolyl substituted or unsubstituted with one or more of phenyl, biphenyl, and naphthyl, which may be further substituted with deuterium.

According to one aspect of the present application, Chemical Formula 2 may be represented by one or more of the following Chemical Formulas 2-1 to 2-11.

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

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

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

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

[Formula 2-9] [Formula 2-10]

[Formula 2-11]

In Formulas 2-1 to 2-8, A ₁ is each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl. According to one aspect of the present application, A ₁ is each independently (C6-C25)aryl substituted or unsubstituted with one or more of deuterium, (C6-C25)aryl, and (6-20 membered)heteroaryl; Dibenzofuranyl substituted or unsubstituted with one or more of deuterium and (C6-C15)aryl; Dibenzothiophenyl substituted or unsubstituted with one or more of deuterium and (C6-C15)aryl; Alternatively, it may be carbazolyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl. According to one aspect of the present application, A ₁ is each independently (C6-C20)aryl substituted or unsubstituted with one or more of deuterium, (C6-C20)aryl, and (6-15 membered)heteroaryl; Dibenzofuranyl substituted or unsubstituted with one or more of deuterium and (C6-C10)aryl; Dibenzothiophenyl substituted or unsubstituted with one or more of deuterium and (C6-C10)aryl; Alternatively, it may be carbazolyl substituted or unsubstituted with one or more of deuterium and (C6-C12)aryl. For example, A ₁ is each independently phenyl substituted or unsubstituted with one or more of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; Biphenyl; terphenyl; Naphthyl substituted or unsubstituted with phenyl; triphenylenyl; phenanthrenyl; 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, naphthyl, and biphenyl, which may be further substituted with deuterium.

In the above formulas _2-1 to 2-8, X ₁₁ to It's Aril. For example, X ₁₁ to X ₂₆ may each independently be hydrogen or deuterium.

In Formula 2-9, T ₁ and Y ₁ are each independently -N=, -(NR ₂₂ )-, -O-, or -S-, provided that any one of T ₁ and Y ₁ is -N= and the other of T ₁ and Y ₁ is -N(R ₂₂ )-, -O-, or -S-. For example, one of T ₁ and Y ₁ may be -N=, and the other of T ₁ and Y ₁ may be -O- or -S-.

In Formula 2-10, V is -N(R ₂₃ )-, -C(R ₂₄ )(R ₂₅ )-, -O-, -S-, or -Se-. For example, V can be -N(R ₂₃ )-, -C(R ₂₄ )(R ₂₅ )-, -O-, or -S-.

In Formula 2-9, R ₁₆ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, R ₁₆ may be unsubstituted (C6-C18)aryl, or unsubstituted (6-13 membered)heteroaryl. According to another aspect of the present application, R ₁₆ may be unsubstituted (C6-C15)aryl, or unsubstituted (6-10 membered) heteroaryl. For example, R ₁₆ can be phenyl, naphthyl, biphenyl or pyridyl.

In Formulas 2-9 and 2-10, R ₁₇ to R ₂₁ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30) )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1 -C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, fused ring group of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1- C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono - or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino , substituted or unsubstituted (C1-C30)alkyl (3-30 membered)heteroarylamino, substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, substituted or unsubstituted (C2- It may be C30) alkenyl (3-30 membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino, or may be connected to an adjacent substituent to form a ring. According to one aspect of the present application, R ₁₇ to R ₂₁ may each independently be hydrogen, or may be connected to an adjacent substituent to form a (6-15 membered) monocyclic or polycyclic alicyclic, aromatic, or combination thereof ring. there is. According to another aspect of the present application, R ₁₇ to R ₂₁ may each independently be hydrogen, or may be connected to an adjacent substituent to form a (6-10 membered) aromatic ring. For example, R ₁₇ to R ₂₁ may each independently be hydrogen, or may be connected to an adjacent substituent to form a benzene ring.

Wherein R ₂₂ to R ₂₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 members) heteroaryl; R ₂₄ and R ₂₅ may be connected to each other to form a spiro ring. According to one aspect of the present application, R ₂₂ to R ₂₅ may each independently be hydrogen, unsubstituted (C1-C10)alkyl, or unsubstituted (C6-C18)aryl, and R ₂₄ and R ₂₅ are each other. They can be connected to form a spiro ring. According to another aspect of the present application, R ₂₂ to R ₂₅ may each independently be hydrogen, unsubstituted (C1-C6)alkyl, or unsubstituted (C6-C15)aryl, and R ₂₄ and R ₂₅ are They can be connected to each other to form a spiro ring. For example, R ₂₂ to R ₂₅ may each independently be hydrogen, methyl, phenyl, or biphenyl, and R ₂₄ and R ₂₅ may be linked to each other to form a spirofluorene ring.

In Formulas 2-9 to 2-11, r and s are each independently 1 or 2, t, v and w are each independently an integer from 1 to 4, and u is an integer from 1 to 3; When r to w are integers of 2 or more, each of R ₁₇ to R ₂₁ may be the same or different from each other.

In Formulas 2-1 to 2-11, Ar ₄ to Ar ₆ and L ₄ to L ₆ are the same as defined in Formula 2.

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

In the compounds H2-1 to H2-145, Dn means that n hydrogens are replaced with deuterium. In 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 about 70% to about 100%. . When deuterated beyond the above lower limit, the bond dissociation energy due to deuteration increases, thereby increasing the stability of the compound, and when the compound is used in an organic electroluminescent device, it can exhibit improved lifespan characteristics.

One or more of the compounds C-1 to C-106 and one or more of the compounds H2-1 to H2-284 may be combined and used in an organic electroluminescent device.

The present application provides an organic electroluminescent compound represented by the above formula (1').

A more detailed description of the compound represented by Formula 1' is as follows.

In Formula 1', X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N;

R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

L ₁ to L ₃ Independently, a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 membered) heteroaryl lene, or substituted or unsubstituted (C3-C30)cycloalkylene;

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

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

R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl;

q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other.

_In Formula _{1 ' , specific embodiments of X 1} to

However, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, among Ar ₁ and Ar ₂ At least one is substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted fluorenyl, phenyl substituted with fluorenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaph Tyl, or substituted or unsubstituted terphenyl. According to one aspect of the present application, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, Ar At least one of ₁ and Ar ₂ is (6-25 membered) heteroaryl substituted or unsubstituted with (C6-C18)aryl, fluores substituted or unsubstituted with (C1-C10)alkyl or (C6-C12)aryl. It may be nyl, unsubstituted spirobifluorenyl, unsubstituted naphthylphenyl, or unsubstituted terphenyl. According to another aspect of the present application, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, At least one of Ar ₁ and Ar ₂ is (6-22 membered) heteroaryl substituted or unsubstituted with (C6-C10)aryl, fluorine substituted or unsubstituted with (C1-C6)alkyl or (C6-C10)aryl. It may be orenyl, unsubstituted spirobifluorenyl, unsubstituted naphthylphenyl, or unsubstituted terphenyl. For example, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, Ar ₁ and Ar At least one of _{the 2} is dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, phenyl substituted or unsubstituted carbazolyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenyl It may be substituted indolocarbazolyl, benzofurocarbazolyl, naphthylphenyl, or terphenyl.

The compound represented by Formula 1' may be selected from compounds C-1 to C-98, C-100, C-101, C-104, and C-105, but is not limited thereto.

The present application provides an organic electroluminescent material containing an organic electroluminescent compound represented by Formula 1' and an organic electroluminescent device containing the same.

The organic electroluminescent material may be composed solely of the organic electroluminescent compound of the present application, or may further include common materials included in organic electroluminescent materials.

The organic electroluminescent compound of formula 1' herein includes a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and It may be included in one or more of the electron blocking layers, and preferably may be included in one or more of the light-emitting layer (host material), the electron transport layer, and the electron buffer layer.

Compounds represented by Formulas 1' and 1 herein may be prepared with reference to Schemes 1 and 2 below, but are not limited thereto.

[Scheme 1]

[Scheme 2]

_{In Schemes 1 and 2 , X 1 to _} It is the same as the definition in -3.

The compound represented by Formula 2 can be manufactured by referring to synthetic methods known to those skilled in the art, and in particular, synthetic methods disclosed in numerous patent documents can be used. For example, referring to the methods disclosed in Japanese Patent Publication No. 1996-003547, Korean Patent Publication No. 10-2283849, Korean Patent Publication No. 2021-0098316, and Korean Patent Publication No. 2021-0076837. It may be synthesized, but is not limited thereto.

Exemplary synthesis examples of compounds represented by Formulas 1' and 1 have been described above, but these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, and Suzuki cross-coupling. Specific reaction based on intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN ₁ substitution reaction, SN ₂ substitution reaction, and Phosphine-mediated reductive cyclization reaction. Those skilled in the art will easily understand that the above reaction proceeds even if other substituents defined in Formulas 1' and 1 are combined in addition to the substituents specified in the synthesis example.

Deuterated compounds of formula 2 can also be non-deuterated 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 the 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 Formula 2 can be adjusted by adjusting the reaction temperature and time, the equivalent weight of acid, etc.

The main source is the anode; cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer includes a plurality of host materials according to the present disclosure. The first host material and the second host material of the present application may be included in one light-emitting layer, or may be included in different light-emitting layers among a plurality of light-emitting layers. Multiple types of host materials of the present application include the compound represented by Formula 1 and the compound represented by Formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10. , more preferably in a ratio of about 30:70 to about 70:30. In addition, the compound represented by Formula 1 and the compound represented by Formula 2 can be mixed in a desired ratio by placing them in a shaker and mixing them, placing them in a glass tube, dissolving them by heat and then collecting them, or dissolving them in a solvent. Can be combined.

According to one aspect of the present application, the doping concentration of the dopant compound relative to the host compound of the light emitting layer may be less than 20% by weight. 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 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; Adjacent substituents may be linked to each other to form a ring, for example, together with pyridine, substituted or unsubstituted quinoline, substituted or unsubstituted benzopuropyridine, substituted or unsubstituted benzothienopyridine, substituted or may form unsubstituted indenopyridine, substituted or unsubstituted benzopuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 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.

The organic electroluminescent device according to the present disclosure includes an anode; cathode; and one or more organic material layers interposed between the anode and the cathode. The organic material layer includes a light-emitting layer, and is selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. It may further include more than one floor. Each of the above layers may be further composed of multiple layers.

The anode and cathode may each be formed of a transparent conductive material, or may be formed of a transflective or reflective conductive material. Depending on the type of material forming the anode and cathode, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-side emitting type. Additionally, the hole injection layer may be additionally doped with P-dopant, and the electron injection layer may be additionally doped with n-dopant.

The organic layer may further include one or more compounds selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. In addition, the organic material 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 these metals. It may additionally contain a complex compound.

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

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.

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 a plurality of 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. A plurality of layers may also be used as a hole transport layer or an electron blocking 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 or the electron transport layer may also be comprised of multiple layers, and multiple compounds may be used for each layer.

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 located between the anode and the light-emitting layer, it facilitates the injection and/or transfer of holes or blocks the overflow of electrons. When used for this purpose or 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. ) is a layer that can be adjusted. In addition, the electron blocking layer is located between the hole transport layer (or hole injection layer) and the light-emitting layer, and is a layer that blocks the overflow of electrons from the light-emitting layer and traps excitons within the light-emitting layer to prevent light leakage. When the hole transport layer includes two or more layers, the additional layer may be used as the hole auxiliary layer or the electron blocking layer. The light emitting auxiliary layer, hole auxiliary layer, or electron blocking layer has the effect of improving the efficiency and/or lifespan of the organic electroluminescent device.

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 material according to an example of the present application can be used as a light emitting material 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 organic electroluminescent material according to an example of the present application may also be used in an organic electroluminescent device including quantum dots (QDs).

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 the first host compound and the second host compound of the present application into a film, 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.

Hereinafter, 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 driving voltage and luminous efficiency of the 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 only illustrate the properties of the compound according to the present application and the OLED containing the same for a detailed understanding of the present application, and the present application is not limited to the following examples.

[Example 1] Synthesis of Compound C-55

Compound 1 (2.3 g, 5.18 mmol) and triphenyl (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) germanium (2.5 g) in a flask. , 4.93 mmol), tetrakis(triphenylphosphine)palladium (0.17 g, 0.15 mmol), potassium carbonate (1.7 g, 12.33 mmol), 25 mL of toluene, 6 mL of ethanol, and 6 mL of distilled water were added and dissolved, then 120 It was refluxed and stirred at ℃ 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-55 (1.0 g, yield: 25%).

[Example 2] Synthesis of Compound C-11

Compound 2 (3.8 g, 9.32 mmol) and triphenyl (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) germanium (4.7 g) in a flask. , 9.32 mmol), tetrakis(triphenylphosphine)palladium (0.3 g, 0.28 mmol), potassium carbonate (3.2 g, 23.29 mmol), 47 mL of toluene, 12 mL of ethanol, and 12 mL of distilled water were added and dissolved, then 120 It was refluxed and stirred at ℃ 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-11 (1.2 g, yield: 17%).

[Device Examples 1 to 3] Manufacturing of OLEDs containing 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 deposition equipment, compound HI-1 of Table 2 below was added to a cell in the vacuum deposition equipment, and compound HT-1 was placed in another cell, and then the two materials were mixed at different speeds. After evaporation, Compound HI-1 was doped to a thickness of 10 nm in an amount of 3% by weight based on the total amount of Compound HI -1 and Compound HT-1, and a hole injection layer was deposited. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. Each of the first and second host compounds listed in Table 1 below were placed as hosts in two cells in the vacuum deposition equipment, and compound D-39 was placed as a dopant in another cell, and then the two host materials were added as 1: A 40 nm thick light-emitting layer was deposited on the second hole transport layer by evaporating at a rate of 1 and simultaneously evaporating the dopant material at different rates and doping the dopant in an amount of 3% by weight based on the total amount of host and dopant. . Next, an electron transport layer was deposited on the light emitting layer to a thickness of 35 nm using compound ET-1 and compound EI-1 as electron transport materials at a weight ratio of 50:50. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

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

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

The driving voltage, luminous efficiency, luminous color, and light intensity based on 10,000 nit luminance of the OLEDs of device Examples 1 to 3 and Comparative Example 1 manufactured as above are reduced from 100% to 95%. The time taken (life: T95) was measured and shown in Table 1 below.

[Table 1]

As shown in Table 1, OLEDs (Device Examples 1 to 3) containing multiple types of host materials according to the present application have a lower driving voltage and higher voltage compared to OLEDs (Comparative Example 1) containing a conventional organic host compound. It was confirmed that not only did it exhibit luminous efficiency, but it also exhibited excellent lifespan characteristics. The OLED according to Comparative Example 1 had low efficiency, so lifespan could not be measured.

The compounds used in Device Examples 1 to 3 and Comparative Example 1 are shown in Table 2 below.

[Table 2]

[Device Example 4] Preparation of OLED containing the compound according to the present disclosure in the electron transport layer

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 deposition equipment, compound HI-1 of Table 4 below was added to a cell in the vacuum deposition equipment, and compound HT-1 was placed in another cell, and then the two materials were mixed at different speeds. After evaporation, Compound HI-1 was doped to a thickness of 10 nm in an amount of 3% by weight based on the total amount of Compound HI -1 and Compound HT-1, and a hole injection layer was deposited. Subsequently, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-3 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 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. The following H-1 was placed as a host in a cell in the vacuum evaporation equipment, and Compound D-150 as a dopant was placed in another cell. Then, the two materials were evaporated at different rates to give a dopant of 2 relative to the total amount of the host and dopant. A 20 nm thick light-emitting layer was deposited on the second hole transport layer by doping in an amount of % by weight. Next, the compounds listed in Table 3 below were added as an electron transport layer to a cell in the vacuum deposition equipment on the light-emitting layer, and compound EI-1 was added to another cell, and then the two materials were deposited at a weight ratio of 50:50 to a thickness of 35 nm. deposited. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Comparative Example 2] Manufacturing of OLED containing a comparative compound in the electron transport layer

An OLED was manufactured in the same manner as Device Example 4, except that the compounds listed in Table 3 were used as the electron transport layer.

The driving voltage based on 1,000 nit luminance and the time it takes for the light intensity based on 1,770 nit luminance to drop from 100% to 95% of the OLED of device Example 4 and Comparative Example 2 manufactured as above (lifetime: T95) The measurements are shown in Table 3 below.

[Table 3]

As shown in Table 3, the OLED (Device Example 4) containing the compound according to the present disclosure in the electron transport layer shows a lower driving voltage and excellent It was confirmed that it exhibited longevity characteristics.

The compounds used in Device Example 4 and Comparative Example 2 are shown in Table 4 below.

[Table 4]

Claims (11)

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

In Formula 1,
X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N;
R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
L ₁ to L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
L' is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl;
q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other;
[Formula 2]

In Formula 2,
L ₄ to L ₆ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
Ar ₄ to Ar ₆ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered) heteroaryl, or two adjacent ones of Ar ₄ to Ar ₆ are linked and substituted. Alternatively, it may form an unsubstituted carbazole ring.
The host material according to claim 1, wherein Formula 1 is represented by one or more of the following Formulas 1-1 to 1-6:
[Formula 1-1] [Formula 1-2]

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

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

In Formulas 1-1 to 1-6,
X is -O-, -S-, -Se-, -N(R ₃₁ )-, or -C(R ₃₂ )(R ₃₃ )-;
R ₃₁ to R ₃₃ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted ( 3-30 members) may be heteroaryl, or adjacent substituents may be connected to each other to form a ring;
R ₁₂ to R ₁₅ are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -N-(R')(R"); or is connected to an adjacent substituent to form a ring. can;
R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or It is unsubstituted (3-30 membered) heteroaryl;
m to o are each independently an integer of 1 to 3, and p are each independently an integer of 1 to 4; When m to p are integers of 2 or more, each of R ₁₂ to R ₁₅ may be the same or different from each other;
X ₁ to X ₃ , Ar ₁ , Ar _{2 ,} L ₁ to L ₃ , L', R ₁ to R ₃ , and q are the same as the definitions in clause 1.
The host material according to claim 1, wherein at least one of Ar ₁ and Ar ₂ of Formula 1 is of the following Formula 1-1-1 or 1-1-2:
[Formula 1-1-1] [Formula 1-1-2]

In the above formulas 1-1-1 and 1-1-2,
X' is -O-, -S-, -Se-, -N(R ₃₄ )-, or -(CR ₃₅ )(R ₃₆ )-;
R ₃₄ to R ₃₆ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted ( 3-30 members) may be heteroaryl, or adjacent substituents may be connected to each other to form a ring;
R ₄ to R ₇ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -N-(R')(R"); or is connected to an adjacent substituent to form a ring. can;
R' and R" are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or It is unsubstituted (3-30 membered) heteroaryl;
a is an integer of 1 to 3, b to d are each independently an integer of 1 to 4, and when a to d are integers of 2 or more, each of R ₄ to R ₇ may be the same or different from each other;
* indicates the binding position with L ₁ or L ₂ .
The host material according to claim 1, wherein Formula 2 is represented by one or more of the following Formulas 2-1 to 2-11:
[Formula 2-1] [Formula 2-2]

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

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

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

[Formula 2-9] [Formula 2-10]

[Formula 2-11]

In Formulas 2-1 to 2-11,
A ₁ is each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl;
X _{11 to}
T ₁ and Y ₁ are each independently -N=, -N(R ₂₂ )-, -O-, or -S-, provided that any one of T ₁ and Y ₁ is -N=, and T ₁ and Y the other of ₁ is -(NR ₂₂ )-, -O- or -S-;
V is -N(R ₂₃ )-, -C(R ₂₄ )(R ₂₅ )-, -O-, -S- or -Se-;
R ₁₆ is substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₁₇ to R ₂₁ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono - or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) Alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) hetero It may be arylamino, or substituted or unsubstituted (C6-C30)aryl(3-30 membered)heteroarylamino, or may be connected to an adjacent substituent to form a ring;
R ₂₂ to R ₂₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) hetero. is aryl; R ₂₄ and R ₂₅ may be connected to each other to form a spiro ring;
r and s are each independently 1 or 2, t, v and w are each independently an integer from 1 to 4, and u is an integer from 1 to 3; When r to w are integers of 2 or more, each of R ₁₇ to R ₂₁ may be the same or different from each other;
Ar ₄ to Ar ₆ and L ₄ to L ₆ are the same as the definitions in clause 1.
The method of claim 1, wherein the substituents of substituted alkyl(ren), substituted aryl(len), substituted heteroaryl(ren), substituted cycloalkyl(ren), substituted heterocycloalkyl, and substituted carbazole rings. are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl; (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, (C1-C30)alkyl, (C6-C30)aryl, and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.
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 compound, Dn means that n hydrogens are replaced with deuterium.
anode; cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer includes the plurality of host materials according to claim 1.
Organic electroluminescent compound represented by the formula 1':
[Formula 1']

In Formula 1',
X ₁ to X ₃ are each independently CR ₀ or N, provided that at least one of X ₁ to X ₃ is N;
R ₀ is each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
L ₁ to L ₃ are each independently a single bond, substituted or unsubstituted (C1-C30)alkylene, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (3-30 members) heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
L' is substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
R ₁ to R ₃ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C6-C30)aryl;
q is 1 or 2, and when q is 2, each L ₃ may be the same or different from each other;
However, when L ₁ to L ₃ are all single bonds and L' is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted terphenylene, among Ar ₁ and Ar ₂ At least one is substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted fluorenyl, phenyl substituted with fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted Naphthylphenyl, substituted or unsubstituted phenylnaphthyl, or substituted or unsubstituted terphenyl.
The organic electroluminescent compound according to claim 9, wherein the organic electroluminescent compound represented by Formula 1' is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 9.