KR20240008238A - A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to a plurality of types of host materials, organic electroluminescent compounds, and organic electroluminescent devices containing the same. The organic electroluminescent compound according to the present disclosure is used as an organic electroluminescent material, or a specific combination of compounds according to the present disclosure is used as an organic electroluminescent material. By including it as a host material, an organic electroluminescent device with improved driving voltage, luminous efficiency, and/or lifespan characteristics can be provided.

Description

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

The present invention relates to multiple types of organic 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. For long-term use and high resolution of displays, OLEDs with high luminous efficiency and/or long lifespan are required.

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. Accordingly, there is a continuous need to develop organic electroluminescent devices with improved performance, such as improved driving voltage, luminous efficiency, power efficiency, and/or lifespan characteristics compared to previously disclosed organic electroluminescent devices.

Meanwhile, Korean Patent Publication No. 2020-0035905 discloses a compound whose basic skeleton is a structure in which benzoxazole or benzothiazole is bonded to pyrimidine or triazine through a linker, but the organic electroluminescent compound claimed herein , and a plurality of host materials containing a specific combination of compounds are not specifically disclosed. Additionally, there is a need to develop materials with improved performance, such as low driving voltage, high luminous efficiency, and/or long life characteristics compared to the compounds disclosed in the patent document.

Korean Patent Publication No. 2020-0035905 (published on April 6, 2020)

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) The present invention was completed by discovering that multiple types of host materials, which are represented by the second host compound and the second host compound is represented by the following formula (2), achieve the above-mentioned purpose. In addition, the present inventors completed the present invention by discovering that a compound represented by the following formula (3) achieves the above-mentioned purpose.

[Formula 1]

In Formula 1,

X is O or S;

R ₁ to R ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or the following formula (a); However, at least one of R ₁ to R ₅ is of formula (a);

[Formula a]

In formula a,

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

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

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

[Formula 2]

In Formula 2,

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

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

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

[Formula 3]

In Formula 3 above,

X' is O or S;

R' ₁ is hydrogen, deuterium, or phenyl unsubstituted or substituted with deuterium;

R' ₂ to R' ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or the following formula (a'); provided that at least one of R' ₂ to R' ₅ is of formula a';

[Formula a']

In the formula a',

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

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

Ar' ₁ and Ar' ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzo. thiophenyl; provided that at least one of Ar' ₁ and Ar' ₂ is substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl;

Ar' ₁ and Ar' ₂ are different from each other.

The plurality of host materials and organic electroluminescent compounds according to the present disclosure exhibit performance suitable for use in organic electroluminescent devices. In addition, by including the compound according to the present disclosure as an organic electroluminescent material or a specific combination of compounds according to the present disclosure as a plurality of host materials, low driving voltage, high luminous efficiency and/or long-term length are achieved compared to conventional organic electroluminescent devices. An organic electroluminescent device having long-life characteristics 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 of 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” refers to straight or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms, and 1 to 6 carbon atoms. It is more desirable. 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” or “(C3-C30)cycloalkylene” means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, where 3 to 20 carbon atoms are preferred. And, it is more preferable to have 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, “(3-7 membered) heterocycloalkyl” has 3 to 7 ring skeleton atoms and contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si and P, preferably O and S. and N, and include cycloalkyl containing one or more heteroatoms selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, “(C6-C30)aryl” or “(C6-C30)arylene” 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 and arylene include those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, di Benzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spicene Robifluorenyl, spiro[fluorene-benzofluorene]yl, spiro[cyclopentene-fluorene]yl, spiro[dihydroinden-fluorene]yl, azulenyl, tetramethyldihydrophenanthrenyl, etc. there is. 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" or "(3-30 membered) heteroarylene" has 3 to 30 ring skeleton atoms and is selected from the group consisting of B, N, O, S, Si and P. It means an aryl group or arylene group containing one or more heteroatoms. 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 or heteroarylene herein includes forms in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and also includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, and tetrazinyl. , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. single ring heteroaryl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphtho Furopyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl , benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, Benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, di Benzocarbazolyl, phenoxazyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazole, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyridyl. There are fused ring heteroaryls such as midinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi Nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imy Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1 -Isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl Nolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8- Isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7 -yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7 -phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-arc Lidinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole- 1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3 -Methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl , 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho- [1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho -[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naph to-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1- Naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4 -naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl , 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuran 1, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzo furanyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]- Benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b] -benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b ]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2- b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2 -b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2, 3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2 ,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[ 2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho- [2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho -[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3, 2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl midinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9- Benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2- d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzo Thio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d] Pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-ger Mafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. As used herein, “halogen” includes F, Cl, Br and I atoms.

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

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 ring, aromatic ring, or a combination thereof, and even more preferably (C6-C18)aryl and ( It may be a (5-25 membered) monocyclic or polycyclic aromatic ring substituted or unsubstituted with one or more of 3-20 membered heteroaryl. Additionally, the ring formed may contain one or more heteroatoms selected from B, N, O, S, Si and P, preferably one or more heteroatoms selected from N, O and S. For example, the ring may be a benzene ring, cyclopentane ring, indane ring, fluorene ring, phenanthrene ring, indole 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, substituted aryl(lene), substituted heteroaryl(lene), substituted dibenzofuranyl, substituted dibenzothiophenyl, and substituted carbazolyl are each independently selected from 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 deuterium; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (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; (6-25 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl; and (C6-C28)aryl substituted or unsubstituted with deuterium. According to another aspect of the present application, the substituents are each independently deuterium; (6-20 membered)heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C12)aryl; and (C6-C20)aryl substituted or unsubstituted with deuterium. For example, the substituents each independently consist of carbazolyl substituted or unsubstituted with deuterium, phenyl, biphenyl, terphenyl, naphthyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, and phenyl. There may be one or more selected from the group, and they may be further substituted with one or more deuterium.

The plurality of host materials of the present application include a first host material and a second host material, wherein the first host material includes at least one type of compound represented by Formula 1, and the second host material includes at least one type It includes a compound represented by Formula 2.

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

In Formula 1, X is O or S.

In Formula 1, R ₁ to R ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or Formula (a); However, at least one of R ₁ to R ₅ is of formula (a). According to one aspect of the present application, R ₁ to R ₅ are each independently hydrogen; heavy hydrogen; and (C6-C30)aryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl; Or it may be Formula a. According to another aspect of the present application, R ₁ to R ₅ are each independently hydrogen; heavy hydrogen; (C6-C18)aryl substituted or unsubstituted with deuterium; Or it may be Formula a. According to another aspect of the present application, any one of R ₁ to R ₅ may be of formula (a), and the others may each independently be hydrogen; heavy hydrogen; It may be (C6-C12)aryl substituted or unsubstituted with deuterium. For example, R ₁ to R ₅ are each independently hydrogen, deuterium, deuterium-substituted or unsubstituted phenyl, or formula (a); However, any one of R ₁ to R ₅ has formula (a).

The L ₁ is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one aspect of the present application, L ₁ may be a single bond, or a (C6-C30)arylene substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. According to another aspect of the present application, L ₁ may be a single bond, or a (C6-C20)arylene substituted or unsubstituted with deuterium and (C6-C20)aryl. For example, L ₁ may be a single bond, phenylene substituted or unsubstituted with phenyl, biphenylene substituted or unsubstituted with phenyl, or terphenylene, and these may be further substituted with deuterium.

Y ₁ to Y ₃ are each independently N or CH; However, at least two of Y ₁ to Y ₃ are N. For example, two of Y ₁ to Y ₃ are N and the other is CH; Y ₁ to Y ₃ are all N.

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. . According to one aspect of the present application, Ar ₁ and Ar ₂ are each independently a (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, (C6-C30)aryl, and (3-30 membered)heteroaryl. ; Alternatively, it may be a (3-30 membered) heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. According to another aspect of the present application, Ar ₁ and Ar ₂ are each independently a (C6-C25)aryl substituted or unsubstituted with one or more of deuterium, (C6-C20)aryl, and (6-20 membered)heteroaryl. ; Alternatively, it may be a (6-15 membered) heteroaryl substituted or unsubstituted with one or more of deuterium and (C6-C15)aryl. Specifically, Ar ₁ and Ar ₂ are Each independently, phenyl unsubstituted or substituted with dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl; Biphenyl; terphenyl; quarterphenyl; naphthyl; phenylnaphthyl; naphthylphenyl; pyridyl; pyrimidinyl; triazine; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; or carbazolyl substituted or unsubstituted with one or more of phenyl and biphenyl, which may be further substituted with one or more deuterium. For example, Ar ₁ and Ar ₂ are each independently phenyl unsubstituted or substituted with dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl; Biphenyl; terphenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; Alternatively, it may be carbazolyl substituted or unsubstituted with one or more of phenyl and biphenyl, and these may be further substituted with one or more deuterium.

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

In Formula 2, A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or It is unsubstituted carbazolyl. According to one aspect of the present application, A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or It is substituted or unsubstituted carbazolyl, and each of these substituents may independently be one or more of deuterium, (C6-C30)aryl, and (3-30 membered)heteroaryl. According to another aspect of the present application, A ₁ and A ₂ are each independently a (C6) substituted or unsubstituted with one or more of deuterium, (C6-C18)aryl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl. -C25)aryl; Dibenzofuranyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl; Dibenzothiophenyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl; or carbazolyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl. Specifically, A ₁ and A ₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted flu Orenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, It may be substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl. For example, A ₁ and A ₂ are each independently phenyl unsubstituted or substituted with naphthyl, triphenylenyl, dibenzofuranyl, or dibenzothiophenyl; Biphenyl; naphthyl; naphthylphenyl; phenylnaphthyl; terphenyl; triphenylenyl; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; Or it may be carbazolyl substituted with phenyl or naphthyl, and these may be further substituted with deuterium.

In Formula 2, any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are connected to each other to form a single bond. X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. For example, X ₁₁ to X ₂₆ may each independently be hydrogen or deuterium.

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

According to one aspect of the present application, the deuterium substitution rate _of X ₁₁ to Typically, it may be about 55% to about 100%.

According to one aspect of the present application, Formula 2 may be represented by one or more of the following Formulas 2-1 to 2-8.

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

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

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

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

In Formulas 2-1 to 2-8, the definitions and preferred embodiments of A ₁ , A ₂ , and X ₁₁ to X ₂₆ are the same as 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 H2-144, 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-255 and one or more of the compounds H2-1 to H2-280 may be combined and used in an organic electroluminescent device.

The present application provides an organic electroluminescent compound represented by Formula 3 above.

A more detailed description of the compound represented by Formula 3 is as follows.

In Formula 3, X' is O or S.

In Formula 3, R' ₁ is hydrogen, deuterium, or phenyl unsubstituted or substituted with deuterium. According to one aspect of the present application, R ₁ may be phenyl unsubstituted or substituted with deuterium.

In Formula 3, R' ₂ to R' ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or Formula a'; However, at least one of R' ₂ to R' ₅ has the formula a'. According to one aspect of the present application, R' ₂ to R' ₅ may each independently be hydrogen, deuterium, or the formula (a') above. According to one aspect of the present application, any one of R' ₂ to R' ₅ may be of formula a', and the others may each independently be hydrogen or deuterium.

L' ₁ is a single bond, or substituted or unsubstituted (C6-C30)arylene. According to one aspect of the present application, L' ₁ may be a single bond, or a (C6-C30)arylene substituted or unsubstituted with one or more of deuterium and (C6-C30)aryl. According to another aspect of the present application, L' ₁ may be a single bond, or a (C6-C20)arylene substituted or unsubstituted with deuterium and (C6-C20)aryl. For example, L' ₁ may be a single bond, phenylene substituted or unsubstituted with phenyl, biphenylene substituted or unsubstituted with phenyl, terphenylene, etc., and these may be further substituted with deuterium.

Y' ₁ to Y' ₃ are each independently N or CH; However, at least two of Y' ₁ to Y' ₃ are N. For example, two of Y' ₁ to Y' ₃ are N and the other is CH; Y' ₁ to Y' ₃ are all N.

Ar' ₁ and Ar' ₂ are each independently selected from substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzofuranyl. benzothiophenyl; However, at least one of Ar' ₁ and Ar' ₂ is substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, and Ar' ₁ and Ar' ₂ are different from each other. According to one aspect of the present application, when Ar' ₁ and Ar' ₂ are each independently substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, These may each be differently selected from the group consisting of substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl. According to another aspect of the present application, Ar' ₁ and Ar' ₂ are each independently (C6-C18) aryl substituted or unsubstituted with deuterium; carbazolyl substituted or unsubstituted with one or more of deuterium and (C6-C20)aryl; It may be dibenzofuranyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl, or dibenzothiophenyl substituted or unsubstituted with one or more of deuterium and (C6-C18)aryl. For example, Ar' ₁ and Ar' ₂ are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl substituted or unsubstituted with phenyl, dibenzothiophenyl substituted or unsubstituted with phenyl, or phenyl. and carbazolyl substituted or unsubstituted with one or more of biphenyl, and these may be further substituted with deuterium.

The compound represented by Formula 3 may be one or more selected from the following compounds, but is not limited to these.

The compound represented by Formula 1 herein can be prepared by synthetic methods known to those skilled in the art. The compound represented by Chemical Formula 1 herein can be prepared, for example, with reference to Scheme 1-1 and Scheme 1-2 below, and the compound represented by Chemical Formula 3 herein can be prepared, for example, by referring to Scheme 1-2 below. It may be manufactured with reference to 1, but is not limited thereto.

[Reaction Scheme 1-1]

[Reaction Scheme 1-2]

_{In Schemes 1-1 and 1-2 ,}

The compound represented by Formula 2 according to the present application can be prepared by a synthetic method known to those skilled in the art, for example, by referring to Scheme 2 below, but is not limited thereto.

[Scheme 2]

In Scheme 2, A ₁ , A _{2 ,} and X ₁₁ to It is an integer equal to the number of hydrogens in the compounds.

Exemplary synthesis examples of compounds represented by Formulas 1 to 3 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 reaction. , specific synthesis 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 to 3 are combined in addition to the substituents specified in the examples.

Additionally, deuterated compounds of formulas 1 to 3 may be 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 deuterated compound with a deuterated solvent, D6-benzene. Additionally, the degree of deuteration can be controlled by varying reaction conditions such as reaction temperature. For example, the number of deuteriums in Formulas 1 to 3 can be adjusted by adjusting the reaction temperature and time, the equivalent weight of acid, etc.

The present disclosure provides an organic electroluminescent compound represented by Formula 3, an organic electroluminescent material including the organic electroluminescent compound represented by Formula 3, and an organic electroluminescent device including the organic electroluminescent material. 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 device according to the present disclosure includes an anode, a cathode, and at least one organic material layer between the anode and the cathode, and the organic material layer is an organic electroluminescent material containing a compound represented by Formula 3. may include.

The organic electroluminescent compound of Formula 3 of the present application 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 an electron It may be included in one or more of the blocking layers, and in some cases, preferably one or more of a light-emitting layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. may be included in The organic electroluminescent compound of Formula 3 herein may be included as a host material. If necessary, the organic electroluminescent compound herein can be used as a co-host material.

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 the above formula 101,

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

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (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 is (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 unsubstituted It is a ringed (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, or 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, or 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] Preparation of compound C-116

1) Synthesis of Compound B

Compound A (6 g, 26.1 mmol), bis(pinacolato)diboron (13.2 g, 52.2 mmol), Pd ₂ (dba) ₃ (2.4 g, 2.6 mmol), and Sphos (2.1 g, 5.2 mmol) in a reaction vessel. ), and potassium acetate (7.7 g, 78.3 mmol) were added, 130 mL of 1.4-dioxane was added and dissolved, and then refluxed and stirred for 3 hours. After the reaction was completed, the reaction product was washed with distilled water, the organic layer was extracted with ethyl acetate, and dried over magnesium sulfate. The solvent was removed using a rotary evaporator and purified by column chromatography to obtain Compound B (8 g, yield: 96%).

2) Synthesis of compound C-116

Add compound B (5 g, 15.6 mmol), compound C (4.6 g, 12.9 mmol), Pd(PPh ₃ ) ₄ (750 mg, 0.65 mmol), and potassium carbonate (5.3 g, 38.9 mmol) to a reaction vessel, 65 mL of toluene, 20 mL of ethanol, and 20 mL of water were added to dissolve and refluxed at 120°C for 3 hours. At the end of the reaction, the resulting solid was filtered, washed with methanol, and recrystallized with xylene and ethyl acetate to obtain compound C-116 (2.6 g, yield: 32%).

[Example 2] Preparation of compound C-117

Add compound B (6 g, 18.6 mmol), compound D (6 g, 16.7 mmol), Pd(PPh ₃ ) ₄ (1.07 g, 0.92 mmol), and potassium carbonate (7.74 g, 56 mmol) to the reaction vessel, 84 mL of toluene, 28 mL of ethanol, and 28 mL of water were added and dissolved, and then refluxed at 120°C for 3 hours. At the end of the reaction, the resulting solid was filtered, washed with methanol, and recrystallized with xylene and ethyl acetate to obtain compound C-117 (3.7 g, yield: 38.5%).

[Example 3] Preparation of compound C-118

Add compound B (6 g, 18.6 mmol), compound E (6 g, 16.7 mmol), Pd(PPh ₃ ) ₄ (1.07 g, 0.92 mmol), and potassium carbonate (7.74 g, 56 mmol) to the reaction vessel, 84 mL of toluene, 28 mL of ethanol, and 28 mL of water were added and dissolved, and then refluxed at 120°C for 3 hours. At the end of the reaction, the resulting solid was filtered, washed with methanol, and recrystallized with xylene and ethyl acetate to obtain compound C-118 (5.2 g, yield: 54%).

[Example 4] Preparation of compound C-180

Add compound B (3.7 g, 11.6 mmol), compound E (5 g, 11.6 mmol), Pd(PPh ₃ ) ₄ (670 mg, 0.57 mmol), and potassium carbonate (4.8 g, 34.7 mmol) to the reaction vessel, 60 mL of toluene, 30 mL of ethanol, and 30 mL of water were added to dissolve and refluxed at 120°C for 3 hours. At the end of the reaction, the resulting solid was filtered, washed with methanol, and recrystallized with xylene and ethyl acetate to obtain compound C-180 (3.2 g, yield: 47%).

[Device Examples 1 to 10] Manufacturing of OLED by depositing multiple types of host materials according to the present application

An OLED according to the present invention 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 from Table 3 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 in an amount of 3% by weight based on the total amount of Compound HI -1 and Compound HT-1 to a thickness of 10 nm, and a hole injection layer was deposited. Subsequently, compound HT-1 as a first hole transport layer was deposited to a thickness of 80 nm on the hole injection layer. Next, compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. Each of the first and second host compounds listed in Table 1 below were placed as hosts in two cells in the vacuum deposition equipment, and compound D-130 was placed as a dopant in another cell, and then the two host materials were mixed in 1: The second hole transport layer is evaporated at a rate of 2 (first host: second host) and simultaneously evaporates the dopant material at a different rate to dope the dopant in an amount of 10% by weight based on the total amount of the host and dopant. A 40 nm thick light emitting layer was deposited on top. Next, a 35 nm thick electron transport layer was deposited on the emitting layer by evaporating the compound ETL-1 : EIL-1 as an electron transport material at a weight ratio of 40:60. Next, compound EIL-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

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

OLEDs were manufactured in the same manner as device examples 1 to 10, except that only compound C-1 was used as the host of the light emitting layer.

The driving voltage, luminous efficiency, luminous color, and light intensity based on 1,000 nit luminance of the organic electroluminescent devices of Examples 1 to 10 and Comparative Example 1 manufactured as above decreased from 100% to 50% based on 60,000 nit luminance. The time until it falls (life: T50) is shown in Table 1 below.

[Table 1]

As shown in Table 1, the organic electroluminescent device (Device Examples 1 to 10) using multiple types of host materials according to the present application has a lower energy consumption than the organic electroluminescent device (Comparative Example 1) including a conventional host material. It was confirmed that not only does it exhibit high driving voltage and luminous efficiency, but it also exhibits very excellent lifespan characteristics. The organic electroluminescent device according to Comparative Example 1 was unable to achieve 60,000 nit luminance and thus its lifespan could not be measured.

[Device Examples 11 to 14] Manufacturing of OLED by depositing multiple types of host materials according to the present application

An OLED according to the present invention 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 from Table 3 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 in an amount of 3% by weight based on the total amount of Compound HI -1 and Compound HT-1 to a thickness of 10 nm, and a hole injection layer was deposited. Subsequently, compound HT-1 as a first hole transport layer was deposited to a thickness of 80 nm on the hole injection layer. Next, compound HT-2 was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows. The host compound listed in Table 2 below was placed as a host in two cells in the vacuum evaporation equipment, and compound D-130 was placed as a dopant in another cell. Then, the host and dopant materials were simultaneously evaporated at different rates to form the host and dopant. A 40 nm thick light emitting layer was deposited on the second hole transport layer by doping the dopant in an amount of 10% by weight based on the total amount of dopant. Next, a 35 nm thick electron transport layer was deposited on the emitting layer by evaporating the compound ETL-1 : EIL-1 as an electron transport material at a weight ratio of 40:60. Next, compound EIL-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

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

OLEDs were manufactured in the same manner as in Device Examples 11 to 14, except that Compound A was used as the host of the light-emitting layer.

The driving voltage, luminous efficiency, and luminous color based on 1,000 nit luminance of the organic electroluminescent devices of Examples 11 to 14 and Comparative Example 2 manufactured as above, and the light intensity based on 20,000 nit luminance decreased from 100% to 50%. The time to completion (life: T50) is shown in Table 2 below.

[Table 2]

As shown in Table 2, the organic electroluminescent device containing the host compound according to the present disclosure (Device Examples 11 to 14) has a lower driving voltage than the organic electroluminescent device containing the conventional host compound (Comparative Example 2). , it was confirmed that not only does it exhibit high luminous efficiency, but it also exhibits very excellent lifespan characteristics.

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

[Table 3]

Claims (14)

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

In Formula 1,
X is O or S;
R ₁ to R ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or the following formula (a); However, at least one of R ₁ to R ₅ is of formula (a);
[Formula a]

In formula a,
L ₁ is a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered)heteroarylene;
Y ₁ to Y ₃ are each independently N or CH; However, at least two of Y ₁ to Y ₃ are N;
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
[Formula 2]

In Formula 2,
A ₁ and A ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl ego;
Any one of X ₁₅ to X ₁₈ and any one of X ₁₉ to X ₂₂ are linked to each other to form a single bond;
X ₁₁ to X ₁₄ , _{X 23} to X ₂₆ , and X ₁₅ to (3-30 membered) heteroaryl; It can be connected to adjacent substituents to form a ring. The method of claim 1, wherein Ar ₁ and Ar ₂ of formula a are Each independently, phenyl unsubstituted or substituted with dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenylcarbazolyl; Biphenyl; terphenyl; quarterphenyl; naphthyl; phenylnaphthyl; naphthylphenyl; pyridyl; pyrimidinyl; triazine; Dibenzofuranyl substituted or unsubstituted with phenyl; Dibenzothiophenyl substituted or unsubstituted with phenyl; or carbazolyl substituted or unsubstituted with one or more of phenyl and biphenyl, which may be further substituted with one or more deuterium. The host material according to claim 1, wherein in Formula 2, at least one of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ is deuterium. The host material according to claim 1, wherein the compound represented by Formula 2 has a deuterium substitution rate of 40% to 100%. The host material according to claim 1, wherein in Formula 2, the deuterium substitution rate among X ₁₁ to X ₂₆ is 25% to 100%. The host material according to claim 1, wherein Formula 2 is represented by one or more of the following Formulas 2-1 to 2-8:
[Formula 2-1] [Formula 2-2]

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

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

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

In Formulas 2-1 to 2-8,
A ₁ , A ₂ , and X ₁₁ to X ₂₆ are as defined in claim 1. The method of claim 1, wherein A ₁ and A ₂ of Formula 2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted naphthyl. , substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted Multiple types of host materials, which are substituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted dibenzothiophenyl. The method of claim 1, wherein the substituents of substituted alkyl, substituted aryl (lene), substituted heteroaryl (lene), substituted dibenzofuranyl, substituted dibenzothiophenyl, and substituted carbazolyl 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 deuterium; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (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 compounds, Dn means that n hydrogens are replaced with deuterium. Organic electroluminescent compound represented by the following formula (3):
[Formula 3]

In Formula 3 above,
X' is O or S;
R' ₁ is phenyl unsubstituted or substituted with deuterium;
R' ₂ to R' ₅ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or the following formula (a'); provided that at least one of R' ₂ to R' ₅ is of formula a';
[Formula a']

In the formula a',
L' ₁ is a single bond, or substituted or unsubstituted (C6-C30)arylene;
Y' ₁ to Y' ₃ are each independently N or CH; However, at least two of Y' ₁ to Y' ₃ are N;
Ar' ₁ and Ar' ₂ are each independently substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzo. thiophenyl; provided that at least one of Ar' ₁ and Ar' ₂ is substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl;
Ar' ₁ and Ar' ₂ are different from each other. The organic electroluminescent compound according to claim 11, wherein the compound represented by Formula 3 is selected from the following compounds.



























An organic electroluminescent device comprising a plurality of types of host materials according to claim 1. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 11.

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