KR20230171374A - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to a plurality of host materials including at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2, and an organic electroluminescent device including the same. By including a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device showing significantly improved lifespan characteristics can be manufactured.

Description

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

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

Since Tang et al. of Eastman Kodak first developed a TPD/Alq ₃ 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. Commercialization has been 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.

Republic of Korea Patent Publication Nos. 10-2014-0094520, 10-2014-0096203, and 10-2017-0123955 disclose multiple types of host materials, but the specific combination of host materials claimed herein is specifically disclosed. It does not start with .

Republic of Korea Patent Publication 10-2014-0094520 (2014.07.30) Republic of Korea Patent Publication 10-2014-0096203 (2014.08.05) Republic of Korea Patent Publication 10-2017-0123955 (2017.11.09)

The purpose of the present invention is, firstly, to provide a plurality of host materials capable of manufacturing an organic electroluminescent device with long lifespan characteristics, and secondly, by including a specific combination of compounds according to the present disclosure as a host material, lifespan characteristics are improved. To provide a significantly improved organic electroluminescent device.

As a result of intensive research to solve the above technical problems, the present inventors have discovered a plurality of host compounds comprising at least one first host compound represented by the following formula (1) and at least one second host compound represented by the following formula (2) The present invention was completed by discovering that the host material of the species achieves the above-mentioned purpose. However, at least one of the first host compound and the second host compound contains deuterium.

[Formula 1]

In Formula 1,

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

R _a is hydrogen or deuterium;

Ar ₁ to Ar ₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, deuterium, (C6-C30)aryl, or a combination thereof, (C6-C30)aryl substituted or unsubstituted, or the following It is a carbazole group represented by Chemical Formula 1-1; However, at least one of Ar ₁ to Ar ₃ is a carbazole group represented by the following formula 1-1;

[Formula 1-1]

In Formula 1-1,

L ₁ is a single bond, phenylene substituted or unsubstituted with deuterium, biphenylene substituted or unsubstituted with deuterium, terphenylene substituted or unsubstituted with deuterium, or a combination thereof;

R ₁ to R ₈ are each independently hydrogen, deuterium, or (C6-C30)aryl substituted or unsubstituted with deuterium, (C6-C30)aryl, or a combination thereof;

[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;

X ₁₁ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Can be connected to adjacent substituents to form a ring,

One of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are connected by a single bond.

By using a specific combination of compounds according to the present invention as a host material, an organic electroluminescent device showing significantly improved lifespan characteristics can be manufactured.

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

The present application includes a plurality of host materials including a first host compound including one or more types of compounds represented by Formula 1 and a second host compound including one or more types of compounds represented by Formula 2, and the host materials. It relates to an organic electroluminescent device.

The present application relates to an organic electroluminescent compound represented by Formula I-1, an organic electroluminescent material containing the same, and an organic electroluminescent device.

The present application relates to an organic electroluminescent compound represented by Formula I-2, an organic electroluminescent material containing the same, and an organic electroluminescent device.

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 material 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, “multiple types of organic electroluminescent materials” refers to organic electroluminescent materials that are a combination of two or more compounds that can be included in any layer constituting the organic electroluminescent device, and before being included in the organic electroluminescent device ( It may refer to both the material included (e.g., before deposition) and the material included (e.g., after deposition). For example, multiple types of organic electroluminescent materials may be one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Two or more types of compounds that may be included in the above layers may be combined. These two or more types of compounds may be included in the same layer or different layers, may be mixed or co-deposited, or may be deposited individually.

As used herein, “multiple types of host materials” refers to an organic electroluminescent material in which two or more types of host materials are combined, before (e.g., before deposition) and after (e.g., before being included in an organic electroluminescent device) , after deposition) can refer to all materials. The plurality of types of host materials of the present application may be included in any light-emitting layer constituting the organic electroluminescent device, and two or more types of compounds included in the plurality of host materials may be included together in one light-emitting layer, and may be included in different light-emitting layers. may be included. When two or more types of host materials are included in one layer, for example, they may be mixed and deposited to form a layer, or they may be co-deposited separately and simultaneously to form a layer.

As used herein, “(C1-C30)alkyl” refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms, where 1 to 20 carbon atoms are preferred, and 1 to 10 carbon atoms are more preferred. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl, etc. As used herein, “(C3-C30)cycloalkyl” refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, with 3 to 20 carbon atoms being preferred, and 3 to 7 carbon atoms being more preferred. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, "(3-7 membered) heterocycloalkyl" has a ring skeleton of 3 to 7 atoms, preferably 5 to 7 atoms, and is a group consisting of B, N, O, S, Si and P, preferably O. , S and N, and includes cycloalkyl containing one or more heteroatoms selected from the group consisting of, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, “(C6-C30)aryl(lene)” refers to a single-ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms, and may be partially saturated, where the ring carbon number is 6 to 30. It is preferable that it is 6 to 20 pieces, and it is more preferable that it is 6 to 15 pieces. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, quarterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluore. Nyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl , tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl spiro [fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulenyl, tetramethyl-dihydrophenanthrenyl, etc. More specifically, examples of the aryl include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o- Biphenyl, m-biphenyl, p-biphenyl, 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, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3 -Fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl orenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenane Tril, 9-phenanthryl, 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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzoyl Fluoranthenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluore Nyl, 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]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c] Fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluore Nyl, 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]fluore Nyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl orenyl, 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]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo [b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2- Benzo[c]fluorenyl, 11,11-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. can be mentioned. As used herein, “(3-30 membered) heteroaryl (lene)” has 3 to 30 ring skeleton atoms and is one or more heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge. It means an aryl group containing. Here, the number of ring skeleton atoms is preferably 3 to 30, and more preferably 5 to 20. 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, tetrazinyl, Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzo. Thiophenyl, dibenzoselenophenyl, benzopuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzopuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquina Zolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothieno Pyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, iso Indolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzo. Carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, cilafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazoli There are fused ring heteroaryls such as nyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, the heteroaryl is 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl , 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizdinyl, 2-indolizdinyl, 3-indolizdinyl, 5-indolizdinyl, 6-indolizdinyl, 7- Indolizidinyl, 8-indolizdinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 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, 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, aza Carbazolyl-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-acridinyl, 2-oxa Zolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-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- 1, 3-methylpyrrol-5-yl, 2-t-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-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl- 3-indolyl, 4-t-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-naphtho-[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]-benzofuranyl, 3-naphtho -[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naph to-[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]-benzothio Phenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzo Thiophenyl, 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 Nyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzo Thio[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-benzothio[3,2- d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-sila Fluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4 -Germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. As used herein, the “fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30)” has a ring skeleton having 3 to 30 carbon atoms, preferably 3 to 25 carbon atoms, and more preferably 3 to 18 carbon atoms. It refers to a functional group of a ring in which one or more aliphatic rings and one or more aromatic rings each having 6 to 30 ring carbon atoms, preferably 6 to 25 carbon atoms, and more preferably 6 to 18 carbon atoms, are fused together. For example, a fused ring group of one or more benzene and one or more cyclohexane, or a fused ring group of one or more naphthalene and one or more cyclopentane. Herein, the carbon atom of the fused ring group of the aliphatic ring (C3-C30) and the aromatic ring (C6-C30) is one or more heteroatoms selected from B, N, O, S, Si and P, preferably N, It may be replaced with one or more heteroatoms selected from O and S. As used herein, “halogen” includes F, Cl, Br and I atoms.

In addition, “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, and preferably may be a substituted or unsubstituted (5-25 membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. 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. According to an example of the present application, the number of rings skeletal atoms is (5-20 won), and according to another example of the present application, the number of rings skeletal atoms is (5-15 won). In one example, the fused ring is, for example, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted ring, or Unsubstituted fluorene ring, substituted or unsubstituted benzofluorene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted indole ring, substituted or unsubstituted indene ring, It may be in the form of a substituted or unsubstituted benzene ring or a substituted or unsubstituted carbazole ring.

In addition, 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 two or more substituents among the substituents are connected. Also includes substitution with groups. For example, “a substituent group in which two or more substituents are connected” may be pyridine-triazine. That is, pyridine-triazine may be heteroaryl, or it may be interpreted as a substituent where two heteroaryls are connected. In the formulas herein, the substituents of substituted alkyl, substituted aryl (lene), substituted heteroaryl (lene), substituted dibenzofuranyl, substituted dibenzothiophenyl, or 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 membered)heterocycloalkyl, (C6-C30)aryloxy, ( (3-30 membered)heteroaryl, substituted or unsubstituted with one or more of C6-C30)arylthio, deuterium and (C6-C30)aryl, substituted or unsubstituted with one or more of deuterium and (3-30 membered)heteroaryl Ringed (C6-C30)aryl, 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- unsubstituted or substituted with (C1-C30) alkyl. 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 members) heteroarylamino, (C2-C30) alkenyl (C6-C30) arylamino, (C2-C30) alkenyl (3-30 members) hetero. Arylamino, (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( It is preferably at least one selected from the group consisting of C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituents of the above substituents include deuterium; ter t-butyl; phenyl; Biphenyl; dibenzofuranyl; and dibenzothiopheny.

Hereinafter, multiple types of host materials according to one embodiment will be described.

A plurality of types of host materials according to one embodiment are a plurality of types of host materials including at least one type of first host compound and at least one type of second host compound, wherein the first host compound is the compound represented by Formula 1 and the second host compound is a compound represented by Formula 2, where at least one of the first host compound and the second host compound contains deuterium. It may be included in the light-emitting layer of an organic electroluminescent device according to an example.

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

[Formula 1]

In Formula 1,

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

R _a is hydrogen or deuterium;

Ar ₁ to Ar ₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, deuterium, (C6-C30)aryl, or a combination thereof, (C6-C30)aryl substituted or unsubstituted, or the following It is a carbazole group represented by Chemical Formula 1-1; However, at least one of Ar ₁ to Ar ₃ is a carbazole group represented by the following formula 1-1;

[Formula 1-1]

In Formula 1-1,

L ₁ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, or a combination thereof;

R ₁ to R ₈ are each independently hydrogen, deuterium, or (C6-C30)aryl substituted or unsubstituted with deuterium, (C1-C30)alkyl, (C6-C30)aryl, or a combination thereof.

For example, at least two of X ₁ to X ₃ may be N, and preferably, all of X ₁ to X ₃ may be N.

For example, L ₁ may be phenylene, biphenylene, or terphenylene, substituted or unsubstituted with a single bond or deuterium, (C6-C30)aryl, or (5-30 membered)heteroaryl. For example, L ₁ is a single bond or deuterium; phenyl; dimethylfluorenyl; dibenzofuranyl; dibenzothiophenyl; and phenylene, deuterium substituted or unsubstituted with at least one of carbazolyl; phenyl; It may be biphenylene substituted or unsubstituted with at least one of and dibenzofuranyl, or terphenylene substituted or unsubstituted with deuterium.

As an example, Ar ₁ and Ar ₂ are Each independently, is (C6-C30)aryl substituted or unsubstituted with deuterium, (C6-C30)aryl, or a combination thereof, and Ar ₃ may be a carbazole group represented by Formula 1-1. As an example, Ar ₁ and Ar ₂ are each independently substituted or unsubstituted with deuterium, phenyl, biphenyl, terphenyl, or a combination thereof, phenyl, m-biphenyl, o-biphenyl, p-biphenyl, m-terphenyl, o-ter It may be phenyl, p-terphenyl, p-quaterphenyl or m-quaterphenyl. For example, Ar ₁ and Ar ₂ are Each independently, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, quarterphenyl substituted or unsubstituted with deuterium, substituted or unsubstituted with deuterium It may be naphthyl, phenylnaphthyl substituted or unsubstituted with deuterium, naphthylphenyl substituted or unsubstituted with deuterium, or a combination thereof.

For example, Ar ₁ is (C6-C30)aryl substituted or unsubstituted with deuterium, (C6-C30)aryl, or a combination thereof, and Ar ₂ and Ar ₃ are carbazole groups represented by Formula 1-1 above. You can.

As an example, R ₁ to R ₈ may each independently be hydrogen, or (C6-C30)aryl substituted or unsubstituted by deuterium, (C1-C30)alkyl, (C6-C30)aryl, or a combination thereof. and preferably hydrogen or (C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted (C6-C25)aryl, more preferably hydrogen or (C1-C4)alkyl or ( It may be substituted with C6-C30)aryl or may be unsubstituted (C6-C18)aryl. For example, R ₁ to R ₈ are each independently hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, or substituted with deuterium. Alternatively, it may be unsubstituted quaterphenyl, naphthyl substituted or unsubstituted with deuterium, phenylnaphthyl substituted or unsubstituted with deuterium, naphthylphenyl substituted or unsubstituted with deuterium, or a combination thereof. For example, R ₁ to R ₈ are each independently hydrogen, deuterium, tert -butyl, phenyl, biphenyl, terphenyl, or a combination thereof, substituted or unsubstituted, phenyl, p-biphenyl, m -biphenyl, o-biphenyl, p-terphenyl, o-terphenyl, or m-terphenyl.

For example, Ar ₁ to Ar ₃ may all be carbazole groups represented by Formula 1-1.

According to one example, the deuterium substitution rate in one compound represented by Formula 1 may be 30% to 100%, preferably 40% to 100%, more preferably 50% to 100%, even more preferably may be 60% to 100%. When deuterated to a number greater than 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.

According to one example, the deuterium substitution rate in Formula 1-1 may be 40% to 100%, preferably 50% to 100%, more preferably 60% to 100%, and even more preferably 75%. It may be from 100% to 100%.

According to one example, the first host compound represented by Formula 1 may be more specifically exemplified by the following compounds, but is not limited to these.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more, which can be up to the number of hydrogens in the compounds.

The compound represented by Formula 1 herein can be prepared by synthetic methods known to those skilled in the art, for example, by referring to Schemes 1-1 to 1-3 below, but is not limited thereto.

[Reaction Scheme 1-1]

[Scheme 1-2]

[Scheme 1-3]

In Schemes 1-1 to 1-3, each substituent has the same definition as in Chemical Formula 1.

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

The second host compound, which is another host material according to one embodiment, is represented by the following formula (2).

[Formula 2]

In Formula 2,

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

X ₁₁ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Can be connected to adjacent substituents to form a ring,

One of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are connected by a single bond.

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

For example, X _{11 to}

According to one example, the deuterium substitution rate of X ₁₁ to X ₂₆ in Formula 2 may be 25% to 100%. As an example, at least four of X ₁₁ to X ₂₆ may be deuterium, and at least one of X ₁₁ , X ₁₈ , _{X 19} and In other words, four of them may be deuterium.

According to one example, in one compound represented by Formula 2, the deuterium substitution rate may be 40% to 100%, preferably 50% to 100%, more preferably 60% to 100%, and even more preferably Typically, it may be 75% to 100%. When deuterated to a number greater than 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 significantly improved lifespan characteristics.

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

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

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

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

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

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

In Formulas 2-1 to 2-8,

A ₁ , A ₂ , and X ₁₁ to X ₂₆ are as defined in Formula 2.

According to one example, the second host compound represented by Formula 2 may be more specifically exemplified by the following compounds, but is not limited to these.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more, which can be up to the number of hydrogens in the compounds.

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 ,} X ₁₁ to

Deuterated compounds of formula 2 can also 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 digested 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.

According to another embodiment of the present invention, the present invention provides an organic electroluminescent compound represented by the following formula (I-1).

[Formula I-1]

In Formula I-1,

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

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

R ₁ to R ₈ are each independently hydrogen, deuterium, or (C6-C30)aryl substituted or unsubstituted with deuterium, (C1-C30)alkyl, (C6-C30)aryl, or a combination thereof; However, at least one of R ₁ to R ₈ contains deuterium.

For example, Ar ₁ and Ar ₂ may each independently be substituted or unsubstituted (C6-C30)aryl, preferably substituted or unsubstituted (C6-C25)aryl, more preferably It may be substituted or unsubstituted (C6-C18)aryl. For example, Ar ₁ and Ar ₂ are each independently phenyl substituted or unsubstituted with deuterium, p-biphenyl substituted or unsubstituted with deuterium, m-biphenyl substituted or unsubstituted with deuterium, or substituted with deuterium. Alternatively, it may be unsubstituted o-biphenyl, p-terphenyl substituted or unsubstituted with deuterium, m-terphenyl substituted or unsubstituted with deuterium, or o-terphenyl substituted or unsubstituted with deuterium.

As an example, L ₁ may be a substituted or unsubstituted (C6-C30)arylene, preferably a substituted or unsubstituted (C6-C25)arylene, and more preferably a substituted or unsubstituted (C6)arylene. -C18) It may be arylene. For example, L ₁ may be phenylene unsubstituted or substituted with deuterium or phenyl, or biphenylene unsubstituted or substituted with deuterium.

For example, R ₁ to R ₈ may each independently be hydrogen, deuterium, or (C6-C25)aryl substituted or unsubstituted with deuterium or (C6-C30)aryl, and preferably hydrogen, deuterium, or It may be (C6-C18)aryl substituted or unsubstituted with deuterium or (C6-C30)aryl. For example, R ₁ to R ₈ are each independently hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium or tert -butyl, p-biphenyl substituted or unsubstituted with deuterium, or unsubstituted or substituted with deuterium. m-biphenyl, o-biphenyl substituted or unsubstituted with deuterium, m-terphenyl substituted or unsubstituted with deuterium, p-terphenyl substituted or unsubstituted with deuterium, or o-substituted or unsubstituted with deuterium -It may be terphenyl.

According to one example, the organic electroluminescent compound represented by Formula I-1 may be more specifically exemplified by the following compounds, but is not limited to these.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more and can be up to the number of hydrogens in the compounds.

According to another embodiment of the present invention, the present invention provides an organic electroluminescent compound represented by the following formula (I-2).

[Formula I-2]

In Formula I-2,

Ar ₁ and Ar ₂ are each independently (C6-C30)aryl substituted or unsubstituted with deuterium;

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

R ₁ to R ₄ , R ₆ and R ₈ are each independently hydrogen or deuterium;

R ₅ and R ₇ are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, or It is a combination of these; However, at least one of R ₅ and R ₇ is biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, or terphenyl substituted or unsubstituted with deuterium.

According to one example, the organic electroluminescent compound represented by Formula I-2 may be more specifically exemplified by the following compounds, but is not limited to these.

Additionally, the present invention provides an organic electroluminescent compound selected from the following compounds.

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

An organic electroluminescent device according to one embodiment includes a first electrode; second electrode; and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one first host compound represented by Formula 1 and Formula 2. It may include multiple types of host materials including one or more types of second host compounds.

According to one example, the organic electroluminescent material of the present application comprises at least one compound from C-1 to C-291, which is a first host compound, and at least one compound from H2-1 to H2-290, which is a second host compound. Includes, and these plural types of host materials may be included in the same organic layer, for example, a light-emitting layer, or may be included in different light-emitting layers.

According to another example, the present disclosure may include an organic electroluminescent compound represented by Formula I-1 or an organic electroluminescent compound represented by Formula I-2 as a host material, electron transport layer material, or electron buffer layer material in the light emitting layer. there is.

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

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

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

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be comprised of multiple layers for the purpose of lowering the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer. Two compounds may be used simultaneously for each layer. Additionally, the hole injection layer may be doped with p-dopant. The electron blocking layer is located between the hole transport layer (or hole injection layer) and the light-emitting layer, and blocks the overflow of electrons from the light-emitting layer, thereby trapping excitons within the light-emitting layer and preventing light emission leakage. The hole transport layer or the electron blocking layer may be comprised of multiple layers, and multiple compounds may be used in each layer.

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

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

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

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

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

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

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

[Formula 101]

In the above formula 101,

L is selected from structures 1 to 3 below;

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6) -C30)aryl, cyano, substituted or unsubstituted (C3-C30)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₀ to R ₁₀₃ may have adjacent substituents connected to each other to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzopuropyridine, or substituted or unsubstituted benzoline. It is possible to form a thienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6) -C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; R ₁₀₄ to R ₁₀₇ may have adjacent substituents connected to each other to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzo. It is possible to form a thiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothienopyridine;

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

s is an integer from 1 to 3.

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

Each layer of the organic electroluminescent device of the present application is formed by any one of dry film deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, or wet film formation methods such as spin coating, dip coating, and flow coating. can be applied. 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.

When forming a film of the first host compound and the second host compound according to an example, the film can be formed by the method listed above, and often can be formed by a co-deposition or mixed deposition process. The co-deposition is a method of mixing and depositing two or more materials into each individual crucible source and evaporating the materials by simultaneously applying current to the two cells. The mixed deposition is a method of mixing and depositing two or more materials into one crucible source before deposition. After mixing, a current is applied to one cell to evaporate the materials, resulting in mixed deposition.

According to one example, when the first host compound and the second host compound exist in the same layer or different layers in the organic electroluminescent device, the two host compounds may be formed separately. For example, the second host compound may be deposited after depositing the first host compound.

According to one embodiment, the present invention can provide a display device including a plurality of types of host materials including a first host compound represented by Formula 1 and a second host compound represented by Formula 2. 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, a method for producing an organic electroluminescent compound according to the present application will be described, taking as an example a method of synthesizing a representative compound or an intermediate compound of the present application.

[Example 1] Preparation of Compound C-3

Compound A (4 g, 23.92 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (9.9 g) in a reaction vessel. , 28.71 mmol), cesium carbonate (Cs ₂ CO ₃ ) (15.6 g, 47.84 mmol), 4-dimethylaminopyridine (DMAP) (1.5 g, 11.96 mmol), and 120 mL of dimethyl sulfoxide (DMSO) were added and incubated at 100°C. It was stirred for 3 hours. After the reaction was completed, it was washed with distilled water, the organic layer was extracted with ethyl acetate, dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-3 (5.0g, yield: 44%).

[Example 2] Preparation of compound C-113

1) Synthesis of compound 2-1

2-phenylcarbazole (50.0 g, 205.49 mmol), 1-bromo-3-iodobenzene (145 g, 513.74 mmol), CuI (19.56 g, 102.74 mmol), Cs ₂ CO ₃ (167.3 g, 513.74 mmol), 1,500 mL of toluene, and ethylenediamine (12.35 g, 205.49 mmol) were added and stirred at 155°C for 3 hours. When the reaction was completed, it was cooled to room temperature, distilled water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. Afterwards, residual moisture was removed using magnesium sulfate, followed by distillation under reduced pressure and separation by column chromatography to obtain compound 2-1 (80 g, yield: 97.74%).

2) Synthesis of compound 2-2

Compound 2-1 (80 g, 200.85 mmol), PdCl ₂ (PPh ₃ ) ₂ (7.04 g, 10.04 mmol), 4,4,4',4',5,5,5',5'-octa in a flask. Add methyl-2,2'-bi(1,3,2-dioxabororane) (66.29 g, 261.10 mmol), KOAc (49.4 g, 502.13 mmol), and 800 mL of 1,4-dioxane and mix. It was heated to 150°C for 4 hours. After the reaction was completed, it was cooled to room temperature, distilled water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate and distilled under reduced pressure. Afterwards, the produced solid was separated by column chromatography to obtain compound 2-2 (51 g, yield: 89.45%).

3) Synthesis of compound C-113

Compound 2-2 (51 g, 114.51 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (39.37) was added to the flask. g, 114.51 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (3.96 g, 3.43 mmol), K ₂ CO ₃ (47.47 g, 343.5 mmol), toluene 1,500 mL, ethanol 70 mL , and 150 mL of distilled water were added and stirred at 140°C for 4 hours. When the reaction was completed, it was cooled to room temperature, distilled water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. Afterwards, residual moisture was removed using magnesium sulfate, followed by distillation under reduced pressure and separation by column chromatography to obtain compound C-113 (48 g, yield: 66.88%).

[Example 3] Preparation of compound C-183-D9

1) Synthesis of compound 3-1

2-phenylcarbazole (0.5 g, 2.05 mmol), 40 mL of benzene-D6, and triflic acid (1 mL, 11.32 mmol) were added to the flask, and stirred at 100°C for 4 hours. When the reaction was completed, it was cooled to room temperature, and 1 mL of D ₂ O was mixed with the reaction mixture and stirred for 10 minutes. Afterwards, the reactant was neutralized with an aqueous K3PO4 solution and the organic layer was extracted with ethyl acetate. Residual moisture was removed using magnesium sulfate, distilled under reduced pressure, and separated by column chromatography to obtain compound 3-1 (0.4 g, yield: 77.22%).

2) Synthesis of compound C-183-D9

Compound 3-1 (4 g, 15.87 mmol), 2-([1,1'-biphenyl]-3-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5 was added to the flask. -triazine (7.99 g, 19.04 mmol), Pd(OAc) ₂ (0.14 g, 0.63 mmol), S-phos (0.65 g, 1.58 mmol), NaOt-bu (3.0 g, 31.94 mmol), and o-xylene 100 mL was added and heated at 160°C for 4 hours. When the reaction was completed, it was cooled to room temperature, distilled water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. Residual moisture was removed using magnesium sulfate, distilled under reduced pressure, and separated by column chromatography to obtain compound C-183-D9 (8.0 g, yield: 79.36%).

[Example 4] Preparation of compound C-163

Compound 1 (6 g, 18.78 mmol), Compound 2 (8.7 g, 22.54 mmol), Pd(OAc) ₂ (420 mg, 1.88 mmol), S-Phos (1.54 g, 3.76 mmol), and NaOtBu (3.61 mmol) were added to the flask. g, 37.57 mmol) was added and dissolved in 94 mL of o-xylene, and then refluxed and stirred at 160°C for 4 hours. When the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the reactant to form a solid, stirred for 30 minutes, filtered, and separated by column chromatography to obtain compound C-163 (2.1 g, yield: 18%).

[Example 5] Preparation of compound C-289

Compound 3 (5 g, 11.23 mmol), compound 4 (4.25 g, 12.35 mmol), Pd(PPh ₃ ) ₄ (390 mg, 0.34 mmol), potassium carbonate (3.88 g, 28.07 mmol), and toluene 56 mL in a reaction vessel. , 14 mL of ethanol, and 14 mL of distilled water were added and stirred at 120°C for 3 hours. After the reaction was completed, it was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed using a rotary evaporator. Afterwards, it was purified by column chromatography to obtain compound C-289 (4.6 g, yield: 66%).

[Example 6] Preparation of compound C-181-D10

Compound 5 (5 g, 19.74 mmol), Compound 2 (9.6 g, 23.69 mmol), Pd(OAc) ₂ (440 mg, 1.97 mmol), S-Phos (1.62 mg, 3.95 mmol), and NaOtBu (3.79 mmol) were added to the flask. g, 39.48 mmol) was added, dissolved in 98 mL of o-xylene, and stirred under reflux at 160°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the reactant in which a solid was formed, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-181-D10 (4.1 g, yield: 37%). .

[Example 7] Preparation of compound C-168-D10

Compound 5 (5 g, 19.74 mmol), Compound 6 (10 g, 23.69 mmol), Pd(OAc) ₂ (440 mg, 1.97 mmol), S-Phos (1.62 g, 3.95 mmol), and NaOtBu (3.79 mmol) were added to the flask. g, 39.48 mmol) was added and dissolved in 98 mL of o-xylene, and then refluxed and stirred at 160°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the reactant in which a solid was formed, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-168-D10 (3.9 g, yield: 31%). .

[Example 8] Preparation of compound C-125

Compound 7 (3 g, 9.39 mmol), Compound 8 (5.2 g, 11.27 mmol), Pd(OAc) ₂ (210 mg, 0.93 mmol), S-Phos (770 mg, 1.87 mmol), and NaOtBu (1.8 mmol) were added to the flask. g, 18.7 mmol) was added and dissolved in 50 mL of o-xylene, and then refluxed and stirred at 160°C for 4 hours. When the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-125 (1.8 g, yield: 65%).

[Example 9] Preparation of compound C-96

Compound 9 (10 g, 41.10 mmol), compound 10 (20.7 g, 53.43 mmol), Pd(OAc) ₂ (0.92 g, 4.11 mmol), S-Phos (3.37 g, 8.22 mmol), and NaOt-bu were added to the flask. (7.9 g, 82.20 mmol) was added, dissolved in 205 mL of o-xylene, and stirred under reflux at 160°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-96 (7.5 g, yield: 33%).

[Example 10] Preparation of compound C-290

Add compound 9 (10 g, 41.10 mmol), compound 11 (15.9 g, 41.10 mmol), CuSO ₄ (3.28 g, 20.55 mmol), and K ₂ CO ₃ (11.36 g, 82.20 mmol) to the flask, 1,2 -Dichlorobenzene (1,2-DCB) was dissolved in 205 mL and stirred under reflux at 200°C for 24 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-290 (11.2 g, yield: 49%).

[Example 11] Preparation of compound C-166-D10

Compound 5 (5 g, 19.75 mmol), compound 10 (9.97 g, 25.67 mmol), Pd(OAc) ₂ (0.44 g, 1.97 mmol), S-Phos (1.62 g, 3.95 mmol), and NaOt-bu were added to the flask. (3.80 g, 39.50 mmol) was added and dissolved in 100 mL of o-xylene, and then refluxed and stirred at 160°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the reactant in which a solid was formed, stirred for 30 minutes, stirred, and purified by column chromatography to obtain compound C-166-D10 (11.2 g, yield: 49%).

[Example 12] Preparation of compound C-124

Compound 7 (7 g, 21.92 mmol), compound 12 (11.04 g, 26.30 mmol), Pd(OAc) ₂ (0.49 g, 2.19 mmol), S-Phos (1.80 g, 4.38 mmol), and NaOt-bu ( 4.21g, 43.83mmol) was added and dissolved in 110 mL of o-xylene, and then refluxed and stirred at 160°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-124 (6.5 g, yield: 42%).

[Example 13] Preparation of compound C-291

Compound 13 (6.7 g, 13.19 mmol), Compound 14 (3.13 g, 15.83 mmol), Pd(PPh ₃ ) ₄ (0.46 g, 0.40 mmol), Na ₂ CO ₃ (3.49 g, 32.97 mmol), Toluene 66 in a flask. mL, 16 mL of EtOH, and 16 mL of H ₂ O were added and dissolved, and then refluxed and stirred at 120°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-291 (2.5 g, yield: 30%).

[Example 14] Preparation of compound C-243

Compound 15 (5.0 g, 12.64 mmol), compound 16 (4.06 g, 15.17 mmol), Cs ₂ CO ₃ (4.12 g, 12.64 mmol), 4-(dimethylamino)pyridine (DMAP) (0.77 g, 6.32 mmol) in a flask. ) was added and dissolved in 63 mL of DMSO, and then refluxed and stirred at 100°C for 4 hours. When the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-243 (5.2 g, yield: 65%).

[Example 15] Preparation of compound C-236

Compound 17 (5.0 g, 12.64 mmol), compound 16 (4.06 g, 15.17 mmol), Cs ₂ CO ₃ (4.12 g, 12.64 mmol), and DMAP (0.77 g, 6.32 mmol) were added to the flask, and dissolved in 63 mL of DMSO. Then, it was refluxed and stirred at 100°C for 4 hours. After the reaction was completed, it was cooled to room temperature, and H ₂ O was added to the solid reaction product, stirred for 30 minutes, filtered, and purified by column chromatography to obtain compound C-236 (6.7 g, yield: 84%).

Hereinafter, for a detailed understanding of the present application, a method for manufacturing an organic electroluminescent device including a plurality of host materials according to the present application and its characteristics will be described.

[Device Example 1] Preparation of a green light-emitting organic electroluminescent device containing multiple types of host materials according to the present invention

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 isopropanol before use. Next, after mounting the ITO substrate on the substrate holder of the vacuum evaporation equipment, compound HI-1 was put into a cell in the vacuum evaporation equipment and compound HT-1 was put into another cell, and then the two materials were evaporated at different rates to form the compound. Compound HI-1 was doped in an amount of 3% by weight based on the total amount of HI- 1 and HT-1 , and a 10 nm thick 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 to deposit 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. Then, the two host materials were mixed in 2: evaporating at different rates of 1, and simultaneously evaporating the dopant material at different rates to dope the dopant in an amount of 10% by weight based on the total amount of the host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. deposited. Next, a 35 nm thick electron transport layer was deposited on the emitting layer by doping the compound ETL-1 : EIL-1 at a weight ratio of 40:60 as an electron transport material. 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 device. . For each material, each compound was purified by vacuum sublimation under 10 ^-6 torr.

[Comparative Example 1] Preparation of an organic electroluminescent device containing a conventional host compound

An OLED device was manufactured in the same manner as Device Example 1, except that compound H2-147 was used as the second host of the light-emitting layer.

The driving voltage, luminous efficiency, luminous color, and light intensity based on 20,000 nits luminance of the organic electroluminescent device according to Device Example 1 and Comparative Example 1 manufactured as described above decreased from 100% to 90%. The time to fall (life: T90) was measured for each, and the results are shown in Table 1 below.

[Device Examples 2 to 13] Preparation of green light-emitting organic electroluminescent devices containing multiple types of host materials according to the present invention

An OLED was manufactured in the same manner as Device Example 1, except that the compounds shown in Tables 2 to 5 below were used as host materials for the light emitting layer.

[Comparative Examples 2 to 4] Preparation of organic electroluminescent devices containing conventional host compounds

An OLED was manufactured in the same manner as Device Example 1, except that the compounds listed in Tables 2 to 4 below were used as the host of the light emitting layer.

The driving voltage, luminous efficiency, luminous color, and light intensity based on 60,000 nits luminance of the organic electroluminescent devices of Examples 2 to 13 and Comparative Examples 2 to 4 manufactured as above decreased from 100% to 50%. The time to fall (life: T50) was measured, and the results are shown in Tables 2 to 5 below.

From Tables 1 to 5, it can be seen that the organic electroluminescent device comprising a specific combination of compounds containing at least one deuterium as a host material according to the present invention exhibits significantly improved lifespan characteristics compared to conventional organic electroluminescent devices. You can check it.

[Device Examples 14 to 20] Preparation of green light-emitting organic electroluminescent device containing host material according to the present invention

An OLED was manufactured in the same manner as Device Example 1, except that only the compounds listed in Tables 6 and 7 below were used as host materials for the light emitting layer.

The driving voltage, luminous efficiency, luminous color based on 1,000 nits luminance of the organic electroluminescent device according to device examples 14 to 20 manufactured as described above, and the time until the light intensity based on 20,000 nits luminance falls from 100% to 95%. (Life: T95) was measured and the results are shown in Tables 6 and 7 below, respectively.

The compounds used in the device examples and comparative examples are specifically shown in Table 8 below.

Claims (18)

A plurality of types of host materials including one or more first host compounds and one or more second host compounds, wherein the first host compound is represented by the following formula (1), and the second host compound is represented by the following formula (2): , a plurality of types of host materials, wherein at least one of the first host compound and the second host compound contains deuterium:
[Formula 1]

In Formula 1,
X ₁ to X ₃ are each independently N or CR _a ; However, at least two of X ₁ to X ₃ are N;
R _a is hydrogen or deuterium;
Ar ₁ to Ar ₃ are each independently, substituted or unsubstituted (C1-C30)alkyl, deuterium, (C6-C30)aryl, or a combination thereof, (C6-C30)aryl substituted or unsubstituted, or the following It is a carbazole group represented by Chemical Formula 1-1; However, at least one of Ar ₁ to Ar ₃ is a carbazole group represented by the following formula 1-1;
[Formula 1-1]

In Formula 1-1,
L ₁ is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, or a combination thereof;
R ₁ to R ₈ are each independently hydrogen, deuterium, or (C6-C30)aryl substituted or unsubstituted with deuterium, (C1-C30)alkyl, (C6-C30)aryl, or a combination thereof;
[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;
X ₁₁ to X ₂₆ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Can be connected to adjacent substituents to form a ring,
One of X ₁₅ to X ₁₈ and one of X ₁₉ to X ₂₂ are connected by a single bond. The method of claim 1, wherein Ar ₁ and Ar ₂ of Formula 1 are Each independently, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, quarterphenyl substituted or unsubstituted with deuterium, substituted or unsubstituted with deuterium Multiple types of host materials, which are naphthyl, phenylnaphthyl substituted or unsubstituted with deuterium, naphthylphenyl substituted or unsubstituted with deuterium, or a combination thereof. The method of claim 1, wherein R ₁ to R ₈ of Formula 1-1 are Each independently, hydrogen, deuterium, phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, quarterphenyl substituted or unsubstituted with deuterium, or unsubstituted naphthyl, phenylnaphthyl substituted or unsubstituted with deuterium, naphthylphenyl substituted or unsubstituted with deuterium, or a combination thereof. The host material according to claim 1, wherein the deuterium substitution rate in Formula 1 is 30% to 100%. The host material according to claim 1, wherein the deuterium substitution rate in Formula 1-1 is 40% to 100%. The host material according to claim 1, wherein in Formula 2, at least one of X ₁₁ , X ₁₈ , X ₁₉ and X ₂₆ is deuterium. The host material according to claim 6, wherein in Formula 2, the deuterium substitution rate is 40% to 100%. The host material according to claim 6, wherein in Formula 2, the deuterium substitution rate of X ₁₁ to X ₂₆ is 25% to 100%. The host material according to claim 1, wherein Formula 2 is represented by any one of the following Formulas 2-1 to 2-8:
[Formula 2-1] [Formula 2-2]

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

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

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

In Formulas 2-1 to 2-8,
A ₁ , A ₂ and X ₁₁ to X ₂₆ are as defined in claim 1. The method of claim 1, wherein A ₁ and A ₂ of Formula 2 are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, Naphthyl substituted or unsubstituted with deuterium, fluorenyl substituted or unsubstituted with deuterium, benzofluorenyl substituted or unsubstituted with deuterium, triphenylenyl substituted or unsubstituted with deuterium, triphenylenyl substituted or unsubstituted with deuterium Fluoranthenyl, phenanthrenyl substituted or unsubstituted with deuterium, dibenzofuranyl substituted or unsubstituted with deuterium, carbazolyl substituted or unsubstituted with deuterium, dibenzothiophenyl substituted or unsubstituted with deuterium, or Multiple types of host materials that are combinations of these. The host material according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more, which can be up to the number of hydrogens in the compounds. The host material according to claim 1, wherein the compound represented by Formula 2 is selected from the following compounds.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more, which can be up to the number of hydrogens in the compounds. first electrode; second electrode; and at least one light-emitting layer between the first electrode and the second electrode, wherein the at least one light-emitting layer includes the plurality of host materials according to claim 1. Organic electroluminescent compound represented by formula I-1:
[Formula I-1]

In Formula I-1,
Ar ₁ and Ar ₂ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
L ₁ is a single bond or substituted or unsubstituted (C6-C30)arylene;
R ₁ to R ₈ are each independently hydrogen, deuterium, or (C6-C30)aryl substituted or unsubstituted with deuterium, (C1-C30)alkyl, (C6-C30)aryl, or a combination thereof; However, at least one of R ₁ to R ₈ contains deuterium. The organic electroluminescent compound according to claim 14, wherein the compound represented by Formula I-1 is selected from the following compounds.

In the above compounds, Dn means that n hydrogens are replaced with deuterium, and n is an integer of 1 or more and can be up to the number of hydrogens in the compounds. An organic electroluminescent compound selected from the following compounds.

Organic electroluminescent compound represented by formula I-2:
[Formula I-2]

In Formula I-2,
Ar ₁ and Ar ₂ are each independently (C6-C30)aryl substituted or unsubstituted with deuterium;
L ₁ is a single bond or (C6-C30)arylene substituted or unsubstituted with deuterium;
R ₁ to R ₄ , R ₆ , and R ₈ are each independently hydrogen or deuterium;
R ₅ and R ₇ are each independently phenyl substituted or unsubstituted with deuterium, biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, terphenyl substituted or unsubstituted with deuterium, or It is a combination of these; However, at least one of R ₅ and R ₇ is biphenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with deuterium, or terphenyl substituted or unsubstituted with deuterium. The organic electroluminescent compound according to claim 17, wherein the compound represented by Formula I-2 is selected from the following compounds.