KR20230174704A - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to 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, 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 having low driving voltage, high luminous efficiency, and long 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.

In 1987, Eastman Kodak first developed an organic electroluminescent device (OLED) using low-molecular aromatic diamine and aluminum complexes as materials for forming a light-emitting layer [Reference: Appl. Phys. Lett. 51, 913, 1987].

The light-emitting material of an organic electroluminescent device is the most important factor in determining the light-emitting efficiency of the device. In terms of functionality, it can be divided into host material and dopant material, and the host and dopant material are used to improve color purity, light-emitting efficiency, and stability. You can use it by mixing it. In general, devices with excellent EL characteristics have a structure that includes a light-emitting layer made by doping a host with a dopant. When using such a dopant/host material system, the host material has a significant impact on the efficiency and lifespan of the light-emitting device. , the choice is important.

Recently, the development of organic electroluminescent devices with high efficiency and long lifespan has emerged as an urgent task. In particular, considering the level of electroluminescence characteristics required for medium to large-sized OLED panels, the development of materials that are significantly superior to existing light emitting materials is necessary. The situation is urgent .

Korean Patent Publication No. 10-2014-0057439 discloses an organic electroluminescent device using a heterocyclic compound as a host or hole transport material, but the present application specifically describes an organic electroluminescent device using a plurality of host materials in a specific combination. However, development of host materials to improve OLED performance is still required.

Korean Patent Publication No. 10-2014-0057439 (2014.05.13)

The object of the present invention is, firstly, to provide a plurality of types of host materials capable of manufacturing organic electroluminescent devices with low driving voltage and/or high luminous efficiency and/or long life characteristics, and secondly, to To provide an organic electroluminescent device comprising:

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 a plurality of host materials represented by the following formula (2) as the second host compound achieve the above-mentioned purpose.

[Formula 1]

In Formula 1,

X is O, S, CR ₁₁ R ₁₂ , NR ₁₃ , or Se;

R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30) circle) heteroaryl; Adjacent substituents may be connected to each other to form a ring;

A is a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;

[Formula 1-1]

In Formulas 1 and 1-1,

, 또는

이고; R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl,

, or

ego;

또는

이며;However, at least one of R ₁ to R ₄

or

and;

L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;

Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, each of R ₁ to R ₄ may be the same or different;

* is the connection position with Formula 1;

[Formula 2]

In Formula 2,

X ₁ to X ₃ are each independently N, CH, or CD;

L ₂₁ to L ₂₃ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

Ar ₂₁ to Ar ₂₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) hetero. Aryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1- C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30), or -N-(R')(R''); Can be connected to adjacent substituents to form a ring; However, at least one of Ar ₂₁ to Ar ₂₃ is substituted or unsubstituted (3-30 membered) heteroaryl;

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

By using multiple types of host materials according to the present invention, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long 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 provides a plurality of host materials including one or more first host compounds and one or more second host compounds, and a plurality of host materials including a first host compound represented by Formula 1 and a second host compound represented by Formula 2. It relates to a host material of a species, and an organic electroluminescent device comprising the host material.

The plurality of host materials of the present application may further include one or more third host compounds that are different from the first host compound and the second host compound.

The present application relates to an organic electroluminescent compound represented by Formula 3, an organic electroluminescent material containing the same, and an organic electroluminescent device.

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, “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 through methods used in the art. For example, the two or more types of compounds may be mixed or co-deposited, or may be deposited individually.

As used herein, “(C1-C30)alkyl” refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms, where 1 to 20 carbon atoms are preferred, and 1 to 10 carbon atoms are more preferred. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl, etc. As used herein, “(C3-C30)cycloalkyl” refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, with 3 to 20 carbon atoms being preferred, and 3 to 7 carbon atoms being more preferred. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, “(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 (len)" 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 benzofuropyridine ring, a benzothienopyridine ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, Substituted or unsubstituted phenanthrene ring, substituted or unsubstituted fluorene ring, substituted or unsubstituted benzofluorene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted It may be in the form of an indole ring, a substituted or unsubstituted indene ring, 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, substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, Substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted trialylsilyl, substituted fused ring group of aliphatic ring and aromatic ring, substituted mono- or di-alkylamino, substituted mono - or di-alkenylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted The substituents of alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (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 (C6-C30)aryl; (C6-C30)aryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (3-30 membered)heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; mono- or di- (C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl (C6-C30)aryl, for example, deuterium, cyano, methyl, phenyl, naphthyl, biphenyl, phenanthrenyl, triphenyl. It may be at least one selected from silyl, fluorenyl, dibenzothiophenyl, dibenzofuranyl, and diphenylamino.

Hereinafter, a host material according to one embodiment will be described.

The plurality of host materials according to one embodiment include a first host compound including one or more compounds represented by Formula 1 and a second host compound including one or more compounds represented by Formula 2. .

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

[Formula 1]

In Formula 1,

X is O, S, CR ₁₁ R ₁₂ , NR ₁₃ , or Se;

R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30) circle) heteroaryl; Adjacent substituents may be connected to each other to form a ring;

A is a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;

[Formula 1-1]

In Formulas 1 and 1-1,

, 또는

이고; R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl,

, or

ego;

또는

이며;However, at least one of R ₁ to R ₄

or

and;

L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;

Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, each of R ₁ to R ₄ may be the same or different;

* is the connection position with Chemical Formula 1.

As an example, X may be O or S.

또는

일 수 있다. For example, R ₁ to R ₄ are each independently hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl,

or

It can be.

또는

이고, 예를 들어, R₁ 내지 R₄ 중 적어도 둘은

또는

일 수 있으며, 예를 들어, R₁ 내지 R₄ 중 적어도 둘은

일 수 있다.As an example, at least one of R ₁ to R ₄ is

or

And, for example, at least two of R ₁ to R ₄ are

or

It may be, for example, at least two of R ₁ to R ₄

It can be.

또는

일 수 있다. As an example, at least one of R ₁ , R ₂ , and R ₄

or

It can be.

또는

가 아닌 R₁ 내지 R₄는 각각 독립적으로, 수소, 중수소, 또는 치환 또는 비치환된 (C6-C30)아릴일 수 있고, 예를 들어, 수소, 중수소, 치환 또는 비치환된 페닐, 치환 또는 비치환된 나프틸, 또는 치환 또는 비치환된 비페닐일 수 있다. As an example,

or

R ₁ to R ₄ other than may each independently be hydrogen, deuterium, or substituted or unsubstituted (C6-C30)aryl, for example, hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted It may be substituted naphthyl, or substituted or unsubstituted biphenyl.

For example, L ₁ and L ₂ may each independently be a single bond or a substituted or unsubstituted (C6-C30)arylene, and are preferably a single bond or deuterium; (C6-C30)aryl; and di(C6-C30)arylamino may be substituted or unsubstituted (C6-C25)arylene, more preferably a single bond or deuterium; (C6-C30)aryl; and di(C6-C30)arylamino may be substituted or unsubstituted (C6-C18)arylene. For example, L ₁ and L ₂ are each independently a single bond or deuterium; phenyl; and diphenylamino may be substituted or unsubstituted phenylene.

For example, L ₁ and L ₂ may be a single bond.

For example, Ar ₁ to Ar ₅ may each independently be substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (5-30 membered)heteroaryl, and are preferably deuterium; cyano; (C6-C30)aryl; (5-30 won) heteroaryl; and (C6-C25)aryl substituted or unsubstituted with at least one of di(C6-C30)arylamino, or (5-25 membered)heteroarylyl substituted or unsubstituted with at least one of deuterium and (C6-C30)aryl. Can be, more preferably deuterium; cyano; (C6-C25)aryl; (5-25 members) heteroaryl; and (C6-C25)aryl substituted or unsubstituted with at least one of di(C6-C25)arylamino, or (5-18 membered)heteroaryl substituted or unsubstituted with at least one of deuterium and (C6-C25)aryl. there is. For example, Ar ₁ and Ar ₂ are each independently deuterium; naphthyl; phenylpropyl; dimethylfluorenyl; carbazolyl; pyridyl; dibenzofuranyl; dibenzothiophenyl; phenanthrenyl; Triphenylsilyl; and phenyl substituted or unsubstituted with at least one of diphenylamino, phenyl substituted or unsubstituted with cyano, naphthyl substituted or unsubstituted with pyridyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m -Biphenyl, phenyl; Biphenyl; and pyridyl substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m. -Terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted 9,10-dihydrophenanthrenyl, substituted or unsubstituted o-quarterphenyl, substituted or unsubstituted chrysenyl, phenyl. or unsubstituted pyridyl, carbazolyl substituted or unsubstituted with phenyl, phenanthridinyl substituted or unsubstituted with phenyl, dibenzofuranyl substituted or unsubstituted with deuterium or phenyl, dibenzofuranyl substituted or unsubstituted with phenyl, It may be benzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, or substituted or unsubstituted naphthobenzoselenoryl. For example, Ar ₃ to Ar ₅ are each independently deuterium; cyano; pyridyl; and phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted with at least one of diphenylamino. Phenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted pyridyl, phenyl It may be substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

The first host compound represented by Formula 1 according to one example may be represented by the following Formula I-1 or I-2.

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

In the above formulas I-1 and I-2,

X, R ₁ to R ₄ , and a to d are as defined in Formula 1.

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.

The host compound of Formula 1 according to one example may be prepared as shown in Scheme 1 below, but is not limited thereto, and may also be prepared by synthetic methods known to those skilled in the art.

[Scheme 1]

In Scheme 1, the definition of each substituent is as defined in Chemical Formula 1.

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

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

[Formula 2]

In Formula 2,

X ₁ to X ₃ are each independently N, CH, or CD;

L ₂₁ to L ₂₃ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

Ar ₂₁ to Ar ₂₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) hetero. Aryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1- C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30), or -N-(R')(R''); Can be connected to adjacent substituents to form a ring;

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

For example, X ₁ to X ₃ may each independently be N or CH.

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

As an example, L ₂₁ to L ₂₃ may each independently be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene, preferably It may be a single bond, substituted or unsubstituted (C6-C25)arylene or a substituted or unsubstituted (5-25 membered) heteroarylene, more preferably a single bond, substituted or unsubstituted (C6-C18). It may be arylene or substituted or unsubstituted (5-18 membered) heteroarylene. For example, L ₂₁ to L ₂₃ are each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylphenyl. lene, substituted or unsubstituted phenylnaphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted carbazolilene, substituted or unsubstituted It may be dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted benzonaphthothiophenylene, or substituted or unsubstituted benzonaphthofuranylene.

For example, Ar ₂₁ to Ar ₂₃ are each independently selected from substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30 membered)heteroaryl, or substituted or unsubstituted tri(C6-C30). ) It may be arylsilyl, preferably substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-25 membered)heteroaryl, or substituted or unsubstituted tri(C6-C25)arylsilyl. It may be, more preferably, substituted or unsubstituted (C6-C25)aryl, substituted or unsubstituted (5-18 membered)heteroaryl, or substituted or unsubstituted tri(C6-C18)arylsilyl. there is.

As an example, at least one of Ar ₂₁ to Ar ₂₃ may be a substituted or unsubstituted (5-30 membered) heteroaryl, and preferably, at least two of Ar ₂₁ to Ar ₂₃ are a substituted or unsubstituted (5-30 membered) heteroaryl. circle) may be heteroaryl.

For example, Ar ₂₁ to Ar _{23 -} may all be substituted or unsubstituted (C6-C30)aryl.

For example, Ar ₂₁ to Ar ₂₃ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl. or unsubstituted o-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylsilyl, substituted or Unsubstituted triphenylgermanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or Unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted tri Phenylenyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzoyl Thiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted naphthooxazolyl, substituted or unsubstituted benzonaphthooxazolyl, substituted or unsubstituted naphthothia It may be zolyl, substituted or unsubstituted benzonaphthothiazolyl, or substituted or unsubstituted naphthoimidazolyl. Preferably, Ar ₂₁ to Ar ₂₃ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted Unsubstituted o-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted Substituted triphenylgermanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Substituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted benzo It may be naphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthooxazolyl, substituted or unsubstituted benzonaphthothiazolyl, or substituted or unsubstituted naphthoselenazolyl. . At this time, the substituents of the substituents may be at least one selected from deuterium, cyano, methyl, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylsilyl, fluorenyl, dibenzothiophenyl, and dibenzofuranyl. .

According to one example, at least one of Ar ₂₁ to Ar ₂₃ may be any one selected from Formulas 2-1 to 2-17 below.

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

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

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

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

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

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

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

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

In Formulas 2-1 to 2-17,

T is O, S, CR ₁₇ R ₁₈ , NR ₁₉ , or Se;

Y ₁ and Y ₂ are each independently -N=, -NR ₂₀ -, -O-, -S-, or -Se-; provided that one of Y ₁ and Y ₂ is -N= and the other of Y ₁ and Y ₂ is -NR ₂₀ -, -O-, -S-, or -Se-;

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

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

R ₁₇ to R ₂₀ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Can be connected to adjacent substituents to form a ring;

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

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

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

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

* is the connection position with L ₂₁ to L ₂₃ in Chemical Formula 2.

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

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

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

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

According to 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 host compound of Formula 2 according to the present application can be prepared by referring to a synthesis method known to those skilled in the art, for example, the synthesis method disclosed in Korean Patent Publication No. 10-2020-0092879, etc.

The plurality of host materials according to one embodiment may further include one or more third host compounds that are different from the first and second host compounds.

The third host compound, which is a host material according to one embodiment, may be represented by Formula 4 or Formula 5 below.

[Formula 4]

[Formula 5]

In Formulas 4 and 5 above,

L' ₁ to L' ₄ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;

Ar' ₁ to Ar' ₄ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

HAr' ₁ is substituted or unsubstituted (3-30 membered) heteroaryl.

As an example, in Formula 4, L' ₁ to L' ₃ may each independently be a single bond or a substituted or unsubstituted (C6-C30)arylene, and preferably a single bond or a substituted or unsubstituted (C6) arylene. It may be -C25)arylene, and more preferably it may be a single bond or substituted or unsubstituted (C6-C18)arylene. For example, L' ₁ to L' ₃ may each independently be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted naphthylene.

As an example, in Formula 4, Ar' ₁ to Ar' ₃ may each independently be substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (5-30 membered)heteroaryl, preferably may be substituted or unsubstituted (C6-C25)aryl or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18)aryl or substituted or unsubstituted It may be a (5-25 membered) heteroaryl. For example, Ar' ₁ to Ar' ₃ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, or substituted or unsubstituted m-biphenyl. , substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted chrysenylenyl, substituted or unsubstituted dibenzothiophenyl, substituted Alternatively, it may be unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or 23-membered heteroaryl containing substituted or unsubstituted nitrogen.

For example, in Formula 4, at least one of Ar' ₁ to Ar' ₃ may be represented by Formula 2-10, Formula 2-13, or Formula 2-18 below.

[Formula 2-10] [Formula 2-13]

[Formula 2-18]

In Formulas 2-10, 2-13, and 2-18,

Y ₁ and Y ₂ are each independently -N=, -NR ₂₀ -, -O-, -S-, or -Se-; provided that one of Y ₁ and Y ₂ is -N= and the other of Y ₁ and Y ₂ is -NR ₂₀ -, -O-, -S-, or -Se-;

R ₉ to R ₁₅ and R ₂₀ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkyl. Silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6) -C30) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(R')(R''); Can be connected to adjacent substituents to form a ring;

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

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

l, w, and y are integers from 1 to 4; i, o', and z are integers from 1 to 3; j, k, m, n', and x are integers of 1 or 2;

When l, w, y, i, o', z, j, k, m, n', and x are integers of 2 or more, each of R ₉ to R ₁₅ and R ₂₁ to R ₂₄ may be the same or different from each other. There is;

* is the connection position with L' ₁ to L' ₃ in Chemical Formula 4.

For example, in Formula 4, at least one of Ar' ₁ to Ar' ₃ may be represented by Formula 2-10.

As an example, in Formula 4, at least one of Ar' ₁ to Ar' ₃ may be represented by Formula 2-13.

As an example, in Formula 5, L' ₄ may be a single bond or a substituted or unsubstituted (C6-C30)arylene, and preferably a single bond or a substituted or unsubstituted (C6-C25)arylene, More preferably, it may be a single bond or substituted or unsubstituted (C6-C18)arylene. For example, L' ₄ can be a single bond, substituted or unsubstituted phenylene, or substituted or unsubstituted naphthylene.

As an example, in Formula 5, Ar' ₄ may be substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (5-30 membered)heteroaryl, preferably substituted or unsubstituted (C6) -C25) It may be aryl or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18 membered) heteroaryl. It could be Aryl. For example, Ar' ₄ is substituted or unsubstituted phenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, or substituted or unsubstituted It may be dibenzofuranyl.

HAr' ₁ may be substituted or unsubstituted (5-30 membered) heteroaryl, preferably represented by Formula 2-13 or 2-18, and more preferably represented by Formula 2-18. It can be, and in this case, * is the connection position with L' ₄ in Chemical Formula 5.

According to one example, the third host compound represented by Formula 4 or 5 may be more specifically exemplified by the following compounds, but is not limited to these.

According to another embodiment of the present invention, the present invention provides an organic electroluminescent compound represented by the following formula (3).

[Formula 3]

In Formula 3 above,

X is O, S, CR ₁₁ R ₁₂ , NR ₁₃ , or Se;

R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 members) )heteroaryl; Adjacent substituents may be connected to each other to form a ring;

, 또는

이고;R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl,

, or

ego;

또는

이며;However, at least one of R ₁ to R ₄

or

and;

L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;

Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;

* is the connection position with Formula 3;

a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, each of R ₁ to R ₄ may be the same or different;

However, the following compounds are excluded from Chemical Formula 3.

According to one example, the organic electroluminescent compound represented by Formula 3 may be more specifically exemplified by the following compounds, but is not limited to these.

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. At this time, the weight ratio of the first host compound and the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30. , more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

According to one example, the plurality of host materials according to the present application include at least one compound among compounds H1-1 to H1-743, which is the first host compound represented by Formula 1, and the second host compound represented by Formula 2. It includes at least one compound from H2-1 to H2-741, and these plural types of host materials may be included in the same organic layer, for example, the same light-emitting layer, or may be included in different light-emitting layers.

According to another example, the plurality of host materials according to the present disclosure may further include one or more types of third host compounds that are different from the first host compound and the second host compound. For example, the plurality of host materials according to the present application include at least one compound among compounds H1-1 to H1-743, which are the first host compound represented by Formula 1, and H2, which is the second host compound represented by Formula 2. It may include at least one compound from -1 to H2-741 and at least one compound from H3-1 to H3-60, which is a third host compound represented by Formula 4 or 5.

According to another example, the organic electroluminescent compound represented by Formula 3 of the present application is used as a host material, a hole injection layer material, a hole transport layer material, a hole auxiliary layer material, a light emitting auxiliary layer material, or an electron blocking layer material of the light emitting layer. It can be included.

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 organic electroluminescent material 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. For example, the doping concentration of the dopant compound relative to the host material 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, but phosphorescent dopants are more 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, 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; It can be connected to an adjacent substituent to form a ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted pyridine. may form nopyridine, 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 an adjacent substituent 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 unsubstituted may form unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, 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; It may be connected to an adjacent substituent to form a substituted or unsubstituted ring;

s is an integer from 1 to 3.

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, the method for producing the compound according to the present application will be described by taking the synthesis method of the representative compound or intermediate compound of the present application as an example.

[Example 1] Synthesis of compound H1-52

In a reaction vessel, compound A-1 (5.4 g, 17.88 mmol), compound 1 (5 g, 14.90 mmol), tris(dibenzylideneacetone)dipalladium(0)(Pd ₂ (dba) ₃ ) (0.68 g, 0.745 mmol), sodium tert -butoxide (NaOtBu) (2.1 g, 22.36 mmol), S-phos (0.49 g, 1.19 mmol), and 75 mL of o-xylene were added and stirred under reflux for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through a Celite filter, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-52 (2.6g, yield: 24%).

[Example 2] Synthesis of compound H1-144

1) Synthesis of Compound A-2

Compound A-1 (7 g, 23.1 mmol), aniline (2.5 mL, 27.7 mmol), Pd ₂ (dba) ₃ (1.05 g, 1.1 mmol), Sphos (0.949 g, 2.3 mmol), NaOtBu (3.4 mmol) in a reaction vessel. g, 35.3 mmol) was added, dissolved in 115 mL of o-Xylene, and stirred under reflux for 1 hour. 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. Afterwards, it was purified by column chromatography to obtain Compound A-2 (4.4 g, yield: 53%).

2) Synthesis of compound H1-144

Compound A-2 (4.4 g, 12.2 mmol), Compound 2 (4.76 g, 14.6 mmol), Pd ₂ (dba) ₃ (0.56 g, 0.6 mmol), and Sphos (0.502 g, 1.2 mmol) were added to a reaction vessel with NaOtBu ( 1.76 g, 18.3 mmol) was added, dissolved in 82 mL of o-Xylene, and stirred under reflux for 1 hour. After the reaction was completed, the organic layer was washed with distilled water, extracted with ethyl acetate, dried with magnesium sulfate, and the solvent was removed. Afterwards, it was purified by column chromatography to obtain compound H1-144 (1.3 g, yield: 18%).

[Example 3] Synthesis of compound H1-145

Compound A-2 (6.7 g, 18.64 mmol), Compound 3 (8.9 g, 22.36 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), Sphos (0.76 g, 1.86 mmol) and NaOtBu ( 2.7 g, 27.96 mmol) was added, dissolved in 82 mL of o-Xylene, and stirred under reflux for 1 hour. After the reaction was completed, the organic layer was washed with distilled water, extracted with ethyl acetate, dried with magnesium sulfate, and the solvent was removed. Afterwards, it was purified by column chromatography to obtain compound H1-145 (1.1 g, yield: 9%).

[Example 4] Synthesis of compound H1-65

In a reaction vessel, compound A-1 (5.7 g, 18.95 mmol), compound 4 (6 g, 14.58 mmol), Pd ₂ (dba) ₃ (0.66 g, 0.729 mmol), NaOt-Bu (2.1 g, 21.87 mmol), Tri- tert -butylphosphine (P(t-bu) ₃ ) (50%) (0.7 mL, 1.458 mmol) and 75 mL of toluene were added, followed by refluxing and stirring for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through Celite filter, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-65 (2.6g, yield: 26%).

[Example 5] Synthesis of compound H1-88

In a reaction vessel, compound A-1 (5.7 g, 18.95 mmol), compound 5 (6g, 14.58mmol), Pd ₂ (dba) ₃ ) (0.66g, 0.729mmol), NaOt-Bu (2.1 g, 21.87 mmol), P(t-bu) ₃ (50%) (0.7 mL, 1.458 mmol) and 75 mL of toluene were added, and then refluxed and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, filtered through Celite filter, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-88 (4 g, yield: 40%).

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 Examples 1 to 28] Manufacturing of OLED by co-depositing the first host compound and the second host compound according to the present application

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

[Device Example 29] Manufacturing of OLED by co-depositing the first host compound and the second host compound according to the present application

An OLED was manufactured in the same manner as Device Example 1, except that the first host compound and the second host compound among the host materials of the light emitting layer were deposited in a ratio of 4:6.

[Comparative Examples 1 to 8] Preparation of OLED containing a comparative compound as a host

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

The driving voltage, luminous efficiency, luminous color, and light intensity based on 10,000 nit luminance of the organic electroluminescent devices of Examples 1 to 29 and Comparative Examples 1 to 8 manufactured as described above were 95% at 100%. The time taken to drop to % (life: T95) was measured for each, and the results are shown in Table 1 below.

[Device Examples 30 to 35] Manufacturing of OLED by co-depositing the first host compound, second host compound, and third host compound according to the present application

An OLED was manufactured in the same manner as Device Example 1, except that the first host compound, second host compound, and third host compound shown in Table 2 below were deposited in a ratio of 1:2:1 as the host of the light emitting layer. did.

The driving voltage, luminous efficiency, luminous color, and light intensity based on 10,000 nit luminance of the organic electroluminescent devices according to device examples 30 to 35 manufactured as described above drop from 100% to 95%. The time taken (lifetime: T95) was measured for each, and the results are shown in Table 2 below.

From Tables 1 and 2, the organic electroluminescent device containing a specific combination of compounds according to the present application as a host material exhibits a low driving voltage and/or high luminous efficiency compared to an organic electroluminescent device using a single host material, In particular, it can be seen that the lifespan characteristics are significantly improved.

[Device Examples 36 to 38] Manufacturing of OLED containing the compound according to the present application as a second hole transport layer material

The same method as in Device Example 1, except that the compounds shown in Table 3 below were deposited as the second hole transport layer material, and the first host compound H1-88 and the second host compound H2-739 were deposited as the host of the light emitting layer. OLED was manufactured using this method.

[Comparative Example 9] Manufacturing of OLED containing a comparative compound as a second hole transport layer material

An OLED was manufactured in the same manner as Device Example 36, except that the compound shown in Table 3 below was deposited as a second hole transport layer material.

The driving voltage and power efficiency of the organic electroluminescent devices manufactured as described above in Examples 36 to 38 and Comparative Example 9 were measured based on 1,000 nit luminance, and the results are shown in Table 3 below.

From Table 3, the organic electroluminescent device including the organic electroluminescent compound according to the present invention as the hole transport layer material has a lower driving voltage and lower compared to the organic electroluminescent device including the conventional compound as the hole transport layer material. /Or it can be confirmed that it shows high power efficiency.

Compounds used in the device examples and comparative examples are specifically shown in Table 4 below.

Claims (14)

Multiple types of host materials 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):
[Formula 1]

In Formula 1,
X is O, S, CR ₁₁ R ₁₂ , NR ₁₃ , or Se;
R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30) circle) heteroaryl; Adjacent substituents may be connected to each other to form a ring;
A is a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;
[Formula 1-1]

In Formulas 1 and 1-1,
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl,

, or

ego; However, at least one of R ₁ to R ₄

or

and;
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;
Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, each of R ₁ to R ₄ may be the same or different;
* is the connection position with Formula 1;
[Formula 2]

In Formula 2,
X ₁ to X ₃ are each independently N, CH, or CD;
L ₂₁ to L ₂₃ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
Ar ₂₁ to Ar ₂₃ are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered) hetero. Aryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1- C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted It is a fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30), or -N-(R')(R''); Can be connected to adjacent substituents to form a ring;
R' and R'' are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. The host material according to claim 1, wherein Formula 1 is represented by the following Formula I-1 or I-2:
[Formula I-1] [Formula I-2]

In the above formulas I-1 and I-2,
X, R ₁ to R ₄ , and a to d are as defined in clause 1. The host material according to claim 1, wherein at least one of Ar ₂₁ to Ar ₂₃ of Formula 2 is represented by any one of the following Formulas 2-1 to 2-17:
[Formula 2-1] [Formula 2-2] [Formula 2-3]

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

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

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

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

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

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

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

In Formulas 2-1 to 2-17,
T is O, S, CR ₁₇ R ₁₈ , NR ₁₉ , or Se;
Y ₁ and Y ₂ are each independently -N=, -NR ₂₀ -, -O-, -S-, or -Se-; provided that one of Y ₁ and Y ₂ is -N= and the other of Y ₁ and Y ₂ is -NR ₂₀ -, -O-, -S-, or -Se-;
R ₁ to R ₁₅ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3) -30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, It is a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -N-(R')(R''); Can be connected to adjacent substituents to form a ring;
R' and R'' are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
R ₁₇ to R ₂₀ are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; Can be connected to adjacent substituents to form a ring;
L ₈ is a single bond, substituted or unsubstituted (C6-C30)arylene or substituted or unsubstituted (3-30 membered)heteroarylene;
Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
a and d are integers from 1 to 5, b, e', f, i, and o' are integers from 1 to 3, and c, e, h, f', l, i', and o are integers from 1 to 3. is an integer of 4, d' is an integer of 1 to 6, g, j, k, m, and n' are integers of 1 or 2, and g', j', m', and n are 1;
When a to m, o, d' to f', i', n', and o' are integers of 2 or more, each of R ₁ to R ₁₅ may be the same or different from each other;
* is the connection position with L ₂₁ to L ₂₃ in Chemical Formula 2. The host material according to claim 1, wherein the compound represented by Formula 1 is selected from the following 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 a plurality of host materials according to claim 1. Organic electroluminescent compound represented by the following formula (3):
[Formula 3]

In Formula 3 above,
X is O, S, CR ₁₁ R ₁₂ , NR ₁₃ , or Se;
R ₁₁ to R ₁₃ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 members) )heteroaryl; Adjacent substituents may be connected to each other to form a ring;
R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl,

, or

ego;
However, at least one of R ₁ to R ₄

or

and;
L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C3-C30)cycloalkylene, or substituted or unsubstituted (3-30) circle) heteroarylene;
Ar ₁ to Ar ₅ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, each of R ₁ to R ₄ may be the same or different;
* is the connection position with Formula 3;
However, the following compounds are excluded from Chemical Formula 3.

The organic electroluminescent compound according to claim 7, wherein the compound represented by Formula 3 is selected from the following compounds.

An organic electroluminescent device comprising the organic electroluminescent compound according to claim 7. The plurality of host materials according to claim 1, further comprising at least one third host compound different from the first host compound and the second host compound. The host material according to claim 10, wherein the third host compound is represented by the following formula (4) or (5).
[Formula 4]

[Formula 5]

In Formulas 4 and 5 above,
L' ₁ to L' ₄ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
Ar' ₁ to Ar' ₄ are each independently substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
HAr' ₁ is substituted or unsubstituted (3-30 membered) heteroaryl. The method of claim 11, wherein at least one of Ar' ₁ to Ar' ₃ of Formula 4 is represented by Formula 2-10, 2-13, or 2-18, or HAr' ₁ of Formula 5 is represented by Formula 2-13: or multiple species of host material, as indicated by 2-18.
[Formula 2-10] [Formula 2-13]

[Formula 2-18]

In Formulas 2-10, 2-13, and 2-18,
Y ₁ and Y ₂ are each independently -N=, -NR ₂₀ -, -O-, -S-, or -Se-; provided that one of Y ₁ and Y ₂ is -N= and the other of Y ₁ and Y ₂ is -NR ₂₀ -, -O-, -S-, or -Se-;
R ₉ to R ₁₅ and R ₂₀ to R ₂₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkyl. Silyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6) -C30) arylsilyl, a fused ring group of a substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -N-(R')(R''); Can be connected to adjacent substituents to form a ring;
R' and R'' are each independently substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
Ar ₈ is substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (3-30 membered)heteroaryl;
l, w, and y are integers from 1 to 4; i, o', and z are integers from 1 to 3; j, k, m, n', and x are integers of 1 or 2;
When l, w, y, i, o', z, j, k, m, n', and x are integers of 2 or more, each of R ₉ to R ₁₅ and R ₂₁ to R ₂₄ may be the same or different from each other. There is;
* is the connection position with L' ₁ to L' ₄ of Formula 4 or 5. The host material according to claim 10, wherein the third host compound is selected from the following compounds.

An organic electroluminescent device comprising a plurality of types of host materials according to claim 10.