KR20230143559A - A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same - Google Patents

Abstract

The present application relates to a host material of multiple types, an organic electroluminescent compound, and an organic electroluminescent element comprising the same, wherein the organic electroluminescent element can be provided comprising a specific combination of compounds as the host material of multiple types according to the present application, or comprising a compound according to the present application, thereby improving a driving voltage, a light emitting efficiency, and/or a lifespan characteristic when compared to a conventional organic electroluminescent element.

Description

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

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

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

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

Meanwhile, Chinese Patent Publication No. 110903258 discloses an aromatic amine compound, but does not specifically disclose the host material of the specific compound and specific combination claimed herein. In addition, there is a continuous need to develop light-emitting materials with improved performance, such as improved driving voltage, luminous efficiency, and/or lifetime characteristics compared to combinations of previously disclosed specific compounds.

Chinese Patent Publication No. 110903258 (published March 24, 2020)

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

As a result of intensive research to solve the above technical problems, the present inventors have discovered a plurality of methods comprising a first host material containing a compound represented by the following formula (1) and a second host material containing a compound represented by the following formula (2) The present invention was completed by discovering that a species host material, or a compound represented by the following formula (11), achieves the above-mentioned purpose.

[Formula 1]

In Formula 1,

One of X ₁ and X ₂ is -N= and the other is -O- or -S-;

R is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

Ring A is (C6-C12)arene;

L ₁ and L ₂ 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;

[Formula 2]

In Formula 2,

At least one of T ₅ and T ₆ , and T ₇ and T ₈ is connected to each other to form a ring of the following formula (3);

[Formula 3]

In Formulas 2 and 3,

T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or Unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30) Arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, fused ring group of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono - or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino , substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3 -30 member) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino, or -L ₃ -Ar ₅ . , provided that at least one of T ₁ to T ₁₄ is -L ₃ -Ar ₅ ;

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

Ar ₅ is each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

은 화학식 2와의 융합 부위를 나타내며;

represents the fusion site with Formula 2;

The heteroaryl and the heteroarylene include one or more heteroatoms selected from B, N, O, S, Si, and P.

[Formula 11]

In Formula 11 above,

One of X ₁ and X ₂ is -N= and the other is -O- or -S-;

R is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

A ring is (C6-C12)arene;

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

However, when the A ring is benzene, -N(Ar ₁ )(Ar ₂ ) and -N(Ar ₃ )(Ar ₄ ) exist in ortho or meta positions to each other.

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

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

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

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

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

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

As used herein, “(C1-C30)alkyl” refers to straight or branched chain alkyl having 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms, and 1 to 6 carbon atoms. It is more desirable. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, sec -butyl, etc. As used herein, “(C3-C30)cycloalkyl” refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring carbon atoms, with 3 to 20 carbon atoms being preferred, and 3 to 7 carbon atoms being more preferred. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. As used herein, “(3-7 membered) heterocycloalkyl” has 3 to 7 ring skeleton atoms and contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si and P, preferably O and S. and N, and include cycloalkyl containing one or more heteroatoms selected from N, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, “(C6-C30)aryl”, “(C6-C30)arylene” or “(C6-C30)arene” refers to a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring carbon atoms. This means that it may be partially saturated. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, quinquiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, and benzofluore. Nyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluorane thenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, spiro[cyclopentene-fluorene]yl, spiro[dihydroinden-fluorene]yl, azulenyl, tetramethyldihydrophenanthre Neil, etc. Specifically, examples of the aryl include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3 -Phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, Benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2- Biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p- Terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quarterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9- Fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p- tert -butylphenyl, p- (2-phenylpropyl) phenyl, 4'-methylbiphenyl, 4"- tert -butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9, 9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11, 11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11- Dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl- 10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3- Benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[ b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b] Fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluore Nyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11, 11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11 -Diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11, 11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11 , 11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl , 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluore Nyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl orenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c] Fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c ]Fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[ c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl -9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9 , 10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, etc.

As used herein, "(3-30 membered) heteroaryl" or "(3-30 membered) heteroarylene" has 3 to 30 ring skeleton atoms and is selected from the group consisting of B, N, O, S, Si and P. It means an aryl group or arylene group containing one or more heteroatoms. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl or heteroarylene herein includes forms in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and also includes those having a spiro structure. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, and tetrazinyl. , triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. single ring heteroaryl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, naphthooxazolyl, benzofuroquinolyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzopuropyrimidi Nyl, naphthofuropyrimidinyl, benzothienoquinolyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthothienopyrimidinyl, pyrimidoin doli, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothia Zolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, Quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazole phenazinyl, imidazopyridyl, There are fused ring heteroaryls such as chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, examples of the heteroaryl include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidi Nyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imy Dazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imida Zopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1 -Isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2 -Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl Nolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8- Isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl -1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7 -yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7 -phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-arc Lidinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole- 1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3 -Methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2- tert -butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl , 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2- tert -butyl-1-indolyl, 4- tert -butyl-1-indolyl, 2- tert -butyl-3-indolyl, 4- tert -butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho- [1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho -[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naph to-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1- Naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4 -naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl , 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuran 1, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzo furanyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]- Benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b] -benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b ]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2- b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2 -b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2, 3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2 ,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naphtho-[ 2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho- [2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho -[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3, 2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl midinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9- Benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2- d]pyrizinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzo Thio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d] Pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-ger Mafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. As used herein, “halogen” includes F, Cl, Br and I atoms.

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

In the description of "substituted or unsubstituted" described herein, 'substitution' means replacing a hydrogen atom in a certain functional group with another atom or another functional group (i.e., a substituent), and substitution with a group where two or more substituents among the substituents are connected. It also includes becoming. For example, “a substituent group in which two or more substituents are connected” may be pyridine-triazine. That is, pyridine-triazine may be interpreted as one heteroaryl substituent or as two heteroaryl substituents connected. As used herein, substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted Alkyldiarylsilyl, substituted triarylsilyl, substituted aliphatic ring and aromatic ring fused ring group, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted alkylalkenyl Amino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted mono- or di-heteroarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino , and the substituents of the substituted arylheteroarylamino are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (C6-C30)aryl; Deuterium, cyano, halogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, (C6-C30)aryl and (3- 30 members) (C6-C30)aryl substituted or unsubstituted with one or more of heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one aspect of the present application, the substituents are each independently halogen; cyano; (C1-C20)alkyl; (C3-C25)cycloalkyl; (5-25 membered)heteroaryl substituted or unsubstituted with (C6-C25)aryl; Halogen, cyano, (C1-C20)alkyl, (C3-C25)cycloalkyl, tri(C1-C20)alkylsilyl, tri(C6-C25)arylsilyl, (C6-C25)aryl and (5-25 membered) ) (C6-C25)aryl substituted or unsubstituted with one or more of heteroaryl; tri(C1-C20)alkylsilyl; and at least one selected from the group consisting of tri(C6-C25)arylsilyl. According to another aspect of the present application, the substituents are each independently cyano; (C1-C10)alkyl; (C3-C18)cycloalkyl; (5-20 membered) heteroaryl substituted or unsubstituted with (C6-C18)aryl; Cyano, halogen, (C1-C10)alkyl, (C3-C18)cycloalkyl, tri(C1-C10)alkylsilyl, tri(C6-C18)arylsilyl, (C6-C18)aryl and (5-20 members) ) (C6-C25)aryl substituted or unsubstituted with one or more of heteroaryl; tri(C1-C10)alkylsilyl; and at least one selected from the group consisting of tri(C6-C18)arylsilyl. For example, the substituents are each independently fluoro; methyl; Substituted or unsubstituted phenyl; naphthyl; Biphenyl; phenanthrenyl; dimethylfluorenyl; diphenylfluorenyl; anthracenyl; naphthylphenyl; phenylnaphthyl; terphenyl; chrysenyl; triphenylenyl; spirobifluorenyl; C22aryl; Pyridyl substituted with phenyl; benzofuranyl; benzothiophenyl; Dibenzofuranyl substituted or unsubstituted with phenyl or biphenyl; dibenzothiophenyl; Carbazolyl substituted or unsubstituted with phenyl; Naphthooxazolyl substituted or unsubstituted with phenyl; It may be phenoxazinyl, etc., and the substituent of the substituted phenyl may be one or more of cyano, fluoro, tert -butyl, cyclohexyl, carbazolyl, trimethylsilyl, and triphenylsilyl.

As used herein, heteroaryl, heteroarylene, and heterocycloalkyl may each independently include one or more heteroatoms selected from B, N, O, S, Si, and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1 -C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30)alkyl (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30) ) Alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino , substituted or unsubstituted (C2-C30) alkenyl (3-30 member) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3-30 member) heteroarylamino. More than one may be combined.

The plurality of host materials of the present application include a first host material and a second host material, wherein the first host material includes one or more compounds represented by Formula 1, and the second host material is represented by Formula 2 Contains one or more compounds. According to one aspect of the present application, the compound represented by Formula 1 and the compound represented by Formula 2 are different from each other.

The present application provides compounds represented by Formula 1, 2, or 11. The present application may provide an organic electroluminescent material or an organic electroluminescent device containing the organic electroluminescent compound, and the organic electroluminescent compound may be included as a host material in the light emitting layer.

In Formulas 1 and 11, X ₁ and X ₂ are each independently -N=, -O-, or -S-. According to one aspect of the present application, one of X ₁ and X ₂ is -N=, and the other is -O- or -S-. According to another aspect of the present application, one of X ₁ and X ₂ is -N=, and the other is -O-.

In Formulas 1 and 11, R is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, R is substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-25 membered)heteroaryl. According to another aspect of the present application, R is unsubstituted (C6-C18)aryl, or unsubstituted (5-20 membered)heteroaryl. For example, R may be phenyl, naphthyl, or dibenzofuranyl.

In Formulas 1 and 11, ring A is (C6-C12)arene. For example, the A ring can be benzene or naphthalene.

In Formulas 1 and 11, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one aspect of the present application, L ₁ and L ₂ are each independently a single bond or a substituted or unsubstituted (C6-C25)arylene. According to another aspect of the present application, L ₁ and L ₂ are each independently a single bond or an unsubstituted (C6-C18)arylene. For example, L ₁ and L ₂ may each independently be a single bond or phenylene.

In Formulas 1 and 11, Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered) heteroaryl. According to one aspect of the present application, Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C18)aryl, or substituted or unsubstituted (5-25 membered) heteroaryl. According to another aspect of the present application, Ar ₁ to Ar ₄ are each independently (C6-C18)aryl substituted or unsubstituted with (C1-C30)alkyl, or (C6-C18)aryl substituted or unsubstituted (C6-C18)aryl. 5-20 won) It is heteroaryl. For example, Ar ₁ to Ar ₄ are each independently phenyl, naphthyl, biphenyl, dimethylfluorenyl, phenanthrenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl substituted with phenyl. It may be, etc.

According to one aspect of the present application, in Formula 1, R and Ar ₁ to Ar ₄ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl Nyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted Benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted It is benzonaphthothiophenyl.

According to one aspect of the present application, in Formula 11, R is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted Phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

According to one aspect of the present application, in Formula 1, when ring A is benzene, -L ₁ -N(Ar ₁ )(Ar ₂ ) and -L ₂ -N(Ar ₃ )(Ar ₄ ) are ortho to each other. Or it exists in a meta location. In Formula 11, when the A ring is benzene, -N(Ar ₁ )(Ar ₂ ) and -N(Ar ₃ )(Ar ₄ ) exist in ortho or meta positions to each other.

According to one aspect of the present application, Formula 1 may be represented by one or more of Formulas 4 to 6 below.

[Formula 4]

[Formula 5]

[Formula 6]

_In Formulas _{4 to 6 ,} R _,

In Formula 2, at least one of T ₅ and T ₆ , and T ₇ and T ₈ is connected to each other to form the ring of Formula 3. According to one aspect of the present application, T ₅ and T ₆ are connected to each other to form the ring of Formula 3 above, or T ₇ and T ₈ are connected to each other to form the ring of Formula 3 above.

In Formulas 2 and 3, T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 -C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted ( C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) Alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, fused ring of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring , substituted or unsubstituted mono- or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl ( C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted Mono- or di- (3-30 membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6 -C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 members) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-30 members) heteroarylamino, or -L ₃ -Ar ₅ . According to one aspect of the present application, T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, substituted or unsubstituted (C6-C25)aryl, or - It is L ₃ -Ar ₅ . According to another aspect of the present application, T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, unsubstituted (C6-C18)aryl, or -L. ₃ -Ar ₅ . For example, T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, phenyl, naphthyl, biphenyl, or -L ₃ -Ar ₅ . At least one of T ₁ to T ₁₄ is -L ₃ -Ar ₅ . According to one aspect of the present application, any one of T ₁ to T ₁₄ is -L ₃ -Ar ₅ .

The L ₃ is each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene. According to one aspect of the present application, L ₃ is each independently a single bond, or a substituted or unsubstituted (C6-C25)arylene. According to another aspect of the present application, L ₃ is each independently a single bond, or (C6-C18)arylene substituted or unsubstituted with (C6-C18)aryl. For example, L ₃ may each independently be a single bond, phenyl-substituted or unsubstituted phenylene, naphthylene, or biphenylene.

The Ar ₅ is each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl. According to one aspect of the present application, Ar ₅ is each independently substituted or unsubstituted (5-25 membered) heteroaryl, and the substituents of the substituted heteroaryl are cyano, halogen, (C1-C30)alkyl, (C3) It may be one or more of -C30)cycloalkyl, (C6-C30)aryl, (3-30 membered)heteroaryl, tri(C1-C30)alkylsilyl, and tri(C6-C30)arylsilyl. Specifically, Ar ₅ is substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzothienoquinolyl, Substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or Unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or It is unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzoimidazolyl, or substituted or unsubstituted phenanthroimidazolyl. For example, Ar ₅ is substituted triazinyl, substituted pyrimidinyl, quinolyl substituted with phenyl, isoquinolyl substituted with phenyl, unsubstituted benzothienoquinolyl, naphthyridinyl substituted with phenyl, phenyl and quinazolinyl substituted with one or more of biphenyl, quinoxalinyl substituted with one or more of phenyl and biphenyl, benzoquinoxalinyl substituted with biphenyl, dibenzoquinoxalinyl substituted with biphenyl, biphenyl. Benzofuropyrimidinyl substituted with, acenaphthopyrimidinyl substituted with phenyl, benzoimidazolyl substituted with phenyl, or phenanthroimidazolyl substituted with phenyl, nitrogen-containing 17-membered heteroaryl substituted with methyl, N and O-containing 25-membered heteroaryl. The substituents of the substituted triazinyl include phenyl unsubstituted or substituted with cyano, fluoro, tert -butyl, cyclohexyl, carbazolyl, trimethylsilyl, or triphenylsilyl; naphthyl; Biphenyl; phenanthrenyl; dimethylfluorenyl; diphenylfluorenyl; anthracenyl; naphthylphenyl; phenylnaphthyl; terphenyl; chrysenyl; triphenylenyl; spirobifluorenyl; (C-22) aryl; benzothiophenyl; Dibenzofuranyl substituted or unsubstituted with phenyl or biphenyl; dibenzothiophenyl; Carbazolyl substituted or unsubstituted with phenyl; Naphthooxazolyl substituted with phenyl; And it may be any two selected from the group consisting of phenoxazine. The substituent of the substituted pyrimidinyl may be one or more selected from the group consisting of fluoro, phenyl, biphenyl, phenyl-substituted pyridyl, and dibenzofuranyl.

은 화학식 2와의 융합 부위를 나타낸다.In Formula 3 above,

represents the fusion site with Formula 2.

The heteroaryl and the heteroarylene include one or more heteroatoms selected from B, N, O, S, Si, and P.

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

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

In Formulas 2-1 and 2-2, the definitions of T ₁ to T ₄ and T ₉ to T ₁₄ are the same as those defined in Formula 2, and T ₅ to T 8 are T ₅ to T ₈ that do not form a ring in Formula 2. Same as the definition of T ₈ .

According to one aspect of the present application, Formula 2 may be represented by one or more of the following formulas.

In the above formulas,

T ₁ to T ₁₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono - or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) Alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) hetero Arylamino, or substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino,

L ₃ and Ar ₅ are as defined in Formula 2 above.

The compound represented by Formula 1 may be one or more selected from the following compounds, but is not limited to these.

The compound represented by Formula 11 may be one or more selected from compounds C-1 to C-120 and C-126 to C-435, but is not limited thereto.

The compound represented by Formula 2 may be one or more selected from the following compounds, but is not limited to these.

One or more of the compounds C-1 to C-120 and C-126 to C-435 may be used in an organic electroluminescent device. Additionally, one or more of the compounds C-1 to C-437 and one or more of the compounds H2-1 to H2-281 may be combined and used in an organic electroluminescent device.

The organic electroluminescent compound of Formula 11 herein includes a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron It may be included in one or more of the blocking layers, and in some cases, preferably one or more of a light-emitting layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. may be included in When used in a light-emitting layer, the organic electroluminescent compound of Formula 11 of the present application may be included as a host material, an electron transport layer material, and/or an electron buffer layer material. If necessary, the organic electroluminescent compound herein can be used as a co-host material.

The compounds represented by Formulas 1 and 11 according to the present application can each be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 1 or 11 is shown in Schemes 1-1 and 1-2 below, and Yeon-Ho Cho, et al. It can be manufactured by referring to Tetrahedron, Volume 69, Issue 32, 2013, Pages 6565-6573, etc., but is not limited thereto. The compound of Formula 2 according to the present application can be prepared by synthetic methods known to those skilled in the art, for example, as shown in Scheme 2-1 and Scheme 2-2 below, but is not limited thereto.

[Reaction Scheme 1-1]

[Reaction Scheme 1-2]

_In Schemes _1-1 and _{1-2 ,}

[Reaction Scheme 2-1]

[Reaction Scheme 2-2]

In Schemes 2-1 and 2-2, the definitions of T and T' are each independently the same as the definitions of T ₁ to T ₄ in Formula 2, x is an integer from 1 to 8, and z is an integer from 1 to 4. is an integer, and when x and z are each integers of 2 or more, each T and T' may be the same or different from each other.

Exemplary synthesis examples of compounds represented by Formulas 1, 2, and 11 have been described above, but these are all Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, and Suzuki cross-coupling reaction. Based on coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, Phosphine-mediated reductive cyclization reaction, Wittig reaction, etc. Those skilled in the art will easily understand that the above reaction proceeds even if other substituents defined in Formulas 1, 2, and 11 are combined in addition to the substituents specified in the specific synthesis examples.

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

According to one aspect of the present application, the doping concentration of the dopant compound relative to the host compound of the light emitting layer may be less than 20% by weight. As the dopant included in the organic electroluminescent device of the present application, one or more phosphorescent or fluorescent dopants can be used, and phosphorescent dopants are preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present application is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). , preferably in some cases, may be an ortho-metalized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably in some cases, It may be an ortho-metalated iridium complex compound.

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

[Formula 101]

In the above formula 101,

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

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

R ₁₀₀ to R ₁₀₃ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; Adjacent substituents may be linked to each other to form a ring, for example, together with pyridine, substituted or unsubstituted quinoline, substituted or unsubstituted benzopuropyridine, substituted or unsubstituted benzothienopyridine, substituted or may form unsubstituted indenopyridine, substituted or unsubstituted benzopuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;

R ₁₀₄ to R ₁₀₇ are each independently hydrogen, deuterium, halogen, deuterium and/or halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted is (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; It can be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, with benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or may form unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopuropyridine, or substituted or unsubstituted benzothienopyridine;

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

s is an integer from 1 to 3.

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

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

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

The organic layer may further include one or more compounds selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. In addition, the organic material layer is one or more metals selected from the group consisting of Group 1, Group 2, 4th period transition metals, 5th period transition metals, lanthanide metals, and d-transition organic metals, or one or more metals containing these metals. It may additionally contain a complex compound.

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

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

A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be comprised of 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. A plurality of layers may also be used as a hole transport layer or an electron blocking layer.

An electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be composed of multiple layers for the purpose of controlling electron injection and improving the interface characteristics between the light-emitting layer and the electron injection layer, and each layer may be composed of two compounds simultaneously. The hole blocking layer or the electron transport layer may also be comprised of multiple layers, and multiple compounds may be used for each layer.

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

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

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

Each layer of the organic electroluminescent device of the present invention is formed using dry film deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, or inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating. Any one of the wet film forming methods can be applied. When forming the first host compound and the second host compound of the present application into a film, the process is carried out by co-deposition or mixed deposition.

In the case of the wet film forming method, a thin film is formed by dissolving or dispersing the materials forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane, and the solvent is used to dissolve or disperse the materials forming each layer. It can be anything, as long as there is no problem with the tabernacle.

In addition, the organic electroluminescent device of the present invention can be used to manufacture a display device, such as a display device for a smartphone, tablet, laptop, PC, TV, or vehicle, or a lighting device, such as an outdoor or indoor lighting device. It is possible.

Hereinafter, for a detailed understanding of the present application, we will look at the manufacturing method of the compound according to the present application, its physical properties, and the driving voltage and luminous efficiency of the OLED containing multiple types of host materials according to the present application, referring to the representative compounds of the present application. However, the following examples only illustrate the properties of the compound according to the present application and the OLED containing the same for a detailed understanding of the present application, and the present application is not limited to the following examples.

[Example 1] Preparation of compound C-235

1) Synthesis of Compound A-1

In a flask, compound A (9 g, 50.6 mmol), benzaldehyde (6.44 g, 60.7 mmol), and NaCN (2.48 g, 50.6 mmol) was dissolved in 180 mL of DMF and stirred under reflux at 140°C for 3 hours. After the reaction was completed, it was cooled to room temperature and separated through a silica filter to obtain Compound A-1 (6.0 g, yield: 45%).

2) Synthesis of compound C-235

Compound A-1 (4.0 g, 15.1 mmol), N,4-diphenylaniline (8.2 g, 33.3 mmol), Pd ₂ (dba) ₃ (0.693 g, 0.757 mmol), sphos (0.622 g, 1.51 mmol), and NaOt-Bu (1.46 g, 15.1 mmol) were added to 80 mL of o-xylin and stirred under reflux at 180°C for 0.5 hours. After cooling to room temperature, the mixture was separated using a silica filter to obtain compound C-235 (4.50 g, yield: 43.6%).

[Example 2] Preparation of compound C-21

One) Synthesis of Compound C-21

Compound B (4.0 g, 15.1 mmol), N-phenyldibenzofuran-3-amine (8.05 g, 31.0 mmol), Pd ₂ (dba) ₃ (0.693 g, 0.757 mmol), sphos (0.622 g, 1.51 mmol) and NaOt-Bu (3.64 g, 37.9 mmol) were added to 80 mL of o-xylin and stirred under reflux at 180°C for 2 hours. After cooling to room temperature, the mixture was separated using a silica filter to obtain compound C-21 (2.20 g, yield: 20.5%).

[Example 3] Preparation of compound C-436

One) Synthesis of Compound D-1

Compound D (10.0 g, 15.1 mmol), N-phenyldibenzofuran-2-amine (9.24 g, 35.6 mmol), Pd(OAc) ₂ (0.728 g, 3.24 mmol), P(t-Bu) ₃ (2.62 g, 6.48 mmol) and NaOt-Bu (7.79 g, 81.0 mmol) were added to 160 mL of toluene and stirred under reflux at 180°C for 2 hours. After cooling to room temperature, the mixture was separated using a silica filter to obtain compound D-1 (5.00 g, yield: 31.7%).

2) Synthesis of Compound C-436

Compound D-1 (4.4 g, 15.1 mmol), N,2-diphenylaniline (2.44 g, 9.94 mmol), Pd ₂ (dba) ₃ (0.693 g, 0.757 mmol), sphos (0.622 g, 1.51 mmol) and NaOt-Bu (3.64 g, 37.9 mmol) was added to 50 mL of o-xylin and stirred under reflux at 180°C for 2 hours. After cooling to room temperature, the mixture was separated using a silica filter to obtain compound C-436 (2.00 g, yield: 31.8%).

[Example 4] Preparation of compound C-437

1) Synthesis of compound C-437

Compound E (6.2 g, 15.6 mmol), N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-3-amine (4.73 g, 14.1 mmol), and Pd were added to the flask. ₂ (dba) ₃ (0.64 g, 0.7 mmol), 50% P(t-bu) ₃ (0.7 mL, 1.4 mmol) and NaOt-bu (2.70 g, 22.0 mmol) were added to 70 mL of toluene at 150°C. It was refluxed and stirred. After cooling to room temperature, it was filtered through a Celite filter, dissolved in methylene chloride, separated by column chromatography, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound C-437 (5.7 g, yield: 58%). ) was obtained.

[Device Examples 1 to 3] 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 to a thickness of 10 nm in an amount of 3% by weight based on the total amount of HI- 1 and compound HT-1, and a hole injection layer was deposited. Subsequently, compound HT-1 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. . Subsequently, compound ET-1 and compound EI-1 as electron transport materials were deposited on the light-emitting layer at a weight ratio of 50:50 to 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 Comparative Example 1] Preparation of OLED containing only a comparative compound as a host

An OLED was manufactured in the same manner as Device Example 1, except that H2-146 was used alone as the second host compound 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 Device Examples 1 to 3 and Device Comparative Example 1 manufactured as described above decreased from 100% to 95%. The time taken to fall (life: T95) was measured and shown in Table 1 below.

From Table 1, the organic electroluminescent device (Device Examples 1 to 3) containing a specific combination of compounds according to the present application as a host material is the organic electroluminescent device (device Examples 1 to 3) that does not contain multiple types of host materials according to the present application. Compared to Comparative Example 1), it can be confirmed that it exhibits excellent luminous efficiency and lifespan characteristics while exhibiting a driving voltage of an equivalent level or higher.

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

[Device Example 4] Manufacturing of OLED by depositing a second hole transport layer according to the present application

An OLED according to the present disclosure was manufactured. First, the transparent electrode ITO thin film (10Ω/□) on the OLED glass (manufactured by Geomatec) substrate was ultrasonic cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, after mounting the ITO substrate on the substrate holder of the vacuum deposition equipment, compound HI-1 was added to a cell in the vacuum deposition equipment and compound HT-3 was placed in another cell, and then the two materials were evaporated at different rates to form the compound. Compound HI-1 was doped to a thickness of 10 nm in an amount of 3% by weight based on the total amount of HI-1 and compound HT-3, and the first hole injection layer was deposited. Subsequently, compound HT-3 was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, compound C-235 was added as a second hole transport layer to 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 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. The host compound listed in Table 4 below was placed as a host in two cells in the vacuum evaporation equipment, and Compound D-1 was placed as a dopant in another cell, and then the dopant material was evaporated at different rates to obtain the total amount of host and dopant. A 40 nm thick light emitting layer was deposited on the second hole transport layer by doping the dopant in an amount of 2% by weight. Subsequently, compound HBL was deposited to a thickness of 5 nm as an electron buffer layer on the emitting layer, and compound ET-2 and compound EI-1 as electron transport materials were deposited thereon at a weight ratio of 50:50 to form an electron transport layer with a thickness of 30 nm. deposited. Subsequently, compound EI-1 was deposited to a thickness of 2 nm on the electron transport layer as an electron injection layer, and then an Al cathode was deposited to a thickness of 80 nm on the electron injection layer using another vacuum deposition equipment to manufacture an OLED. For each material, each compound was used by vacuum deposition under 10 ^-6 torr.

[Device Comparative Example 2]

An OLED was manufactured in the same manner as Device Example 4, except that Compound F was used as the second hole transport layer material.

The driving voltage, luminous efficiency, and luminous color of the organic electroluminescent devices of Device Example 4 and Device Comparative Example 2 manufactured as described above based on 1,000 nit luminance were measured and are shown in Table 3 below.

From Table 3, the organic electroluminescent device (Device Example 4) including the specific compound according to the present application as the second hole transport layer material is the organic electroluminescent device that does not include the specific compound according to the present application as the second hole transport layer material. Compared to the light emitting device (Comparative Device Example 2), it can be confirmed that the luminous efficiency is at the same level or higher with a much lower driving voltage.

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

Claims (15)

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

In Formula 1,
One of X ₁ and X ₂ is -N= and the other is -O- or -S-;
R is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
Ring A is (C6-C12)arene;
L ₁ and L ₂ 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;
[Formula 2]

In Formula 2,
At least one of T ₅ and T ₆ , and T ₇ and T ₈ is connected to each other to form a ring of the following formula (3);
[Formula 3]

In Formulas 2 and 3,
T ₁ to T ₄ , T ₉ to T ₁₄ , and T ₅ to T ₈ that do not form a ring are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or Unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30 membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30) Arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, fused ring group of substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono - or di- (C1-C30)alkylamino, substituted or unsubstituted mono- or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino , substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3 -30 member) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-30 member) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-30 membered) heteroarylamino, or -L ₃ -Ar ₅ . , provided that at least one of T ₁ to T ₁₄ is -L ₃ -Ar ₅ ;
L ₃ is each independently a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (3-30 membered) heteroarylene;
Ar ₅ is each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;

represents the fusion site with Formula 2;
The heteroaryl and the heteroarylene include one or more heteroatoms selected from B, N, O, S, Si, and P. The method of claim 1, wherein substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylaryl Silyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring group of aliphatic ring and aromatic ring, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted Alkylalkenylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted mono- or di-heteroarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenyl The substituents of heteroarylamino and substituted arylheteroarylamino are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; phosphine oxide; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 members) heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-30 membered)heteroaryl substituted or unsubstituted with one or more of (C1-C30)alkyl and (C6-C30)aryl; Deuterium, cyano, halogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, (C6-C30)aryl and (3- 30 members) (C6-C30)aryl substituted or unsubstituted with one or more of heteroaryl; tri(C1-C30)alkylsilyl; Tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; A fused ring group of an aliphatic ring (C3-C30) and an aromatic ring (C6-C30); Amino; mono- or di- (C1-C30)alkylamino; mono- or di- (C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di- (3-30 membered) heteroarylamino; (C1-C30)alkyl (3-30 membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl (3-30 membered)heteroarylamino; (C6-C30)aryl (3-30 membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. The host material according to claim 1, wherein Formula 1 is represented by one or more of the following Formulas 4 to 6:
[Formula 4]

[Formula 5]

[Formula 6]

_In Formulas _{4 to 6 ,} R _, The method of claim 1, wherein in Formula 1, R and Ar ₁ to Ar ₄ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl , substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzo Quinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuropyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzoyl. thiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzoyl. Multiple types of host materials, including naphthothiophenyl. The host material according to claim 1, wherein Formula 2 is represented by one or more of the following Formulas 2-1 and 2-2:
[Formula 2-1] [Formula 2-2]

In Formulas 2-1 and 2-2,
T ₁ to T ₄ and T ₉ to T ₁₄ are as defined in clause 1, and T ₅ to T ₈ are as defined in clause 1 for T ₅ to T ₈ that do not form a ring. The host material according to claim 1, wherein Formula 2 is represented by one or more of the following formulas:

In the above formulas,
T ₁ to T ₁₄ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 30 members) Heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or a fused ring group of an unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono - or di- (C2-C30)alkenylamino, substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di- (C6-C30)arylamino , substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, substituted or unsubstituted mono- or di- (3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C30) Alkyl (3-30 membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-30 membered) hetero Arylamino, or substituted or unsubstituted (C6-C30)aryl (3-30 membered)heteroarylamino,
L ₃ and Ar ₅ are as defined in clause 1. The method of claim 1, wherein Ar ₅ in Formula 2 is substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or Unsubstituted benzothienoquinolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted Dibenzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted benzopuropyrimidinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted. Substituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzoimidazolyl, or substituted or unsubstituted phenanthroimidazolyl. Phosphorus, host material for multiple species. The host material according to claim 1, wherein the compound represented by Formula 1 is one or more selected from the following compounds.























































































The host material according to claim 1, wherein the compound represented by Formula 2 is one or more selected from the following compounds.
























































Organic electroluminescent compound represented by the following formula (11):
[Formula 11]

In Formula 11 above,
One of X ₁ and X ₂ is -N= and the other is -O- or -S-;
R is substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
Ring A is a (C6-C12)arene;
Ar ₁ to Ar ₄ are each independently substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30 membered)heteroaryl;
However, when the A ring is benzene, -N(Ar ₁ )(Ar ₂ ) and -N(Ar ₃ )(Ar ₄ ) exist in ortho or meta positions to each other. The method of claim 10, wherein R is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or An organic electroluminescent compound that is unsubstituted naphthylphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. The organic electroluminescent compound according to claim 10, wherein the compound represented by Formula 11 is any one selected from the following compounds.





















































































anode; cathode; and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer includes the plurality of host materials according to claim 1. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10.

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