CN117510423A

CN117510423A - Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same

Info

Publication number: CN117510423A
Application number: CN202310927415.2A
Authority: CN
Inventors: 李孝姃; 宋睿美; 姜炫周; 李美子; 文斗铉; 朴景秦; 朴头龙; 金大圭
Original assignee: Rohm and Haas Electronic Materials Korea Ltd
Current assignee: Rohm and Haas Electronic Materials Korea Ltd
Priority date: 2022-08-04
Filing date: 2023-07-27
Publication date: 2024-02-06

Abstract

The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same. By including a specific combination of compounds according to the present disclosure as a variety of host materials, or by including a compound according to the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifetime characteristics compared to conventional organic electroluminescent devices may be provided.

Description

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same

Technical Field

The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.

Background

In 1987, tang et al, eastman Kodak, inc., by using a TPD/Alq composed of a light-emitting layer and a charge-transporting layer ₃ The bilayer was first developed for small molecule green organic electroluminescent devices (OLEDs). Thereafter, the development of the OLED is rapidly completed and the OLED has been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. However, in many applications such as TV and lighting devices, the lifetime of the OLED is insufficient and still a higher efficiency of the OLED is required. In general, the lifetime of an OLED becomes shorter as the luminance of the OLED becomes higher. Accordingly, for long-term use and high resolution displays, OLEDs having high luminous efficiency and/or long lifetime are required.

In order to improve light emitting efficiency, driving voltage, and/or lifetime, various materials or concepts for an organic layer of an organic electroluminescent device have been proposed. However, they are not satisfactory in practical use. In addition, there has been a continuing need to develop organic electroluminescent materials having more improved performance (e.g., improved driving voltage, luminous efficiency, power efficiency, and/or lifetime characteristics) compared to the specific combinations of compounds previously disclosed.

Meanwhile, korean patent application publication nos. 2015-017173 and 2021-0089596 disclose organic electroluminescent devices comprising a compound having an aryl-substituted pyrimidinyl and/or triazinyl structure as a skeleton and a compound having biscarbazole as a skeleton, but do not specifically disclose various host materials comprising specific combinations of compounds claimed herein. In addition, korean patent application publication nos. 2016-0141672 and 2015-0088712 disclose compounds having aryl-substituted pyrimidinyl and/or triazinyl structures as backbones, but do not specifically disclose the organic electroluminescent compounds claimed herein. Accordingly, there has been a continuing need to develop luminescent materials having more improved performance (e.g., improved driving voltage, luminous efficiency, and/or lifetime characteristics) compared to the specific combinations of previously disclosed compounds.

Disclosure of Invention

Technical problem

It is an object of the present disclosure to provide improved host materials capable of providing organic electroluminescent devices having improved driving voltage, luminous efficiency and/or lifetime characteristics. It is another object of the present disclosure to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. It is still another object of the present disclosure to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and/or lifetime characteristics by including the compound according to the present disclosure, or by including a specific combination of compounds according to the present disclosure.

Solution to the problem

As a result of intensive studies to solve the above technical problems, the present inventors have found that the above object can be achieved by a plurality of host materials comprising a first host compound comprising a compound represented by the following formula 1 and a second host compound comprising a compound represented by the following formula 2, or by a compound represented by the following formula 1-1, wherein at least one of the first host compound and the second host compound contains deuterium; .

In the formula (1) of the present invention,

X ₁ to X ₃ Each independently represents N or CR _a The method comprises the steps of carrying out a first treatment on the surface of the Provided that X ₁ To X ₃ At least two of which are N;

R _a represents hydrogen or deuterium; and is also provided with

Ar ₁ To Ar ₃ Each independently represents a (C6-C30) aryl group which is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group;

in the formula (2) of the present invention,

A ₁ and A ₂ Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group;

X ₁₅ to X ₁₈ Any one of which is combined with X ₁₉ To X ₂₂ Any one of which are connected to each other to form a single bond; and is also provided with

X forming no single bond ₁₁ To X ₁₄ 、X ₂₃ To X ₂₆ And X ₁₅ To X ₂₂ Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings.

In the case of the formula 1-1,

R _a represents hydrogen or deuterium; and is also provided with

Ar ₁ To Ar ₃ Each independently represents unsubstituted or deuterium-substituted or (C6-C30) arylAt least one substituted (C6-C30) aryl; provided that Ar is ₁ To Ar ₃ Are different from each other, and the naphthalene-containing structure and the following structure are excluded.

The beneficial effects of the invention are that

By including a specific combination of compounds according to the present disclosure as a variety of host materials, or by including a compound according to the present disclosure, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or excellent lifetime characteristics as compared to conventional organic electroluminescent devices is provided, and a display device or a lighting device can be manufactured using the organic electroluminescent device.

Detailed Description

Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure.

The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.

The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including host materials and dopant materials), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.

The term "host materials" in the present disclosure means one or more host materials comprising a combination of at least two compounds, which may be contained in any light-emitting layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the various host materials of the present disclosure may be a combination of two or more host materials, which may optionally further comprise conventional materials included in organic electroluminescent materials. Two or more compounds included in the plurality of host materials of the present disclosure may be included together in one light emitting layer, or may be included in different light emitting layers, respectively. For example, two or more host materials may be co-evaporated or co-evaporated, or may be evaporated individually.

In this context, the term "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3-to 7-membered) heterocycloalkyl" means cycloalkyl having 3 to 7 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably O, S and N. The heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, and the like. The term "(C6-C30) aryl" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. The aryl group may be partially saturated; and may include a screw structure. The aryl group may include phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, benzophenanthryl, anthracenyl, indenyl, triphenylenyl A radical, pyrenyl, tetracenyl, perylenyl,Group, naphto-naphthyl group, fluoranthenyl group, spirobifluorenyl group, spiro [ fluorene-benzofluorene ]]Base, spiro [ cyclopentene-fluorene ]]Base, spiro [ indan-fluorene ]]Radicals, azulene radicals, tetramethyl dihydrophenanthryl radicals, and the like. Specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthraceyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthaceneyl, pyrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [ a ]]Fluorenyl and benzo [ b ]]Fluorenyl and benzo [ c ]]Fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-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-tetrabiphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-toluenePhenyl, 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-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl 9, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 11-dimethyl-1-benzo [ a ] ]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ]]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ] ]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl group11, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl, 11-diphenyl-3-benzo [ c ]]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ] ]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like.

The term "(3-to 30-membered) heteroaryl" means an aryl group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si, and P. The heteroaryl group may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be heteroaryl formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may include a screw structure. The above heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthafuranyl, naphthabenzofuranyl, naphthacene thienyl, naphthazolyl, benzofuranquinolinyl, benzobenzoquinazolinyl, benzofurannaphthyridinyl, benzofuranpyrimidinyl, benzothiophenoquinolinyl, benzothiophenoquinazolinyl, naphthyridinyl, benzothiophenopyridinyl, benzothiophenopyrimidinyl, naphthaceneopyrimidinyl, pyrimidoindolyl, benzopyrimidinyl, benzofuranpyrazinyl, naphthafuranpyrazinyl, benzothiophenopyrazinyl, naphthacene naphthazinyl, naphthaceneopyrazinyl, naphthazinyl, benzofuranpyrimidinyl, benzofuranyl, and naphthazinyl pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylphenopyrimidinyl, indolocarbazolyl, quinazolinyl, benzoquinoxalinyl, benzocarbazolyl, benzotriazolyl, imidazolyl, and benzotriazolyl, indenocarbazolyl and the like. More specifically, the process is carried out, heteroaryl groups may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 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-indolinyl (indodidinyl), 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 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-furanyl, 3-furanyl, 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-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 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-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 3-phenanthridinyl, 2-thienyl, 3-thienyl, 2-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpyrrolidin-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, 2-dibenzo- [ 2-3-benzofuranyl, 4-dibenzo-2-benzofuranyl ] -2-b-1-naphtalenyl, 2-b-1-naphtalenyl 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- [2,3-b ] -benzofuranyl, 2-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2, 2-b ] -benzofuranyl, 5-naphtho-b ] -benzofuranyl, 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 ] -benzothienyl, 2-naphtho- [1,2-b ] -benzothienyl, 3-naphtho- [1,2-b ] -benzothienyl, 4-naphtho- [1,2-b ] -benzothienyl, 5-naphtho- [1,2-b ] -benzothienyl, 6-naphtho- [1,2-b ] -benzothienyl 7-naphtho- [1,2-b ] -benzothienyl, 8-naphtho- [1,2-b ] -benzothienyl, 9-naphtho- [1,2-b ] -benzothienyl, 10-naphtho- [1,2-b ] -benzothienyl, 1-naphtho- [2,3-b ] -benzothienyl, 2-naphtho- [2,3-b ] -benzothienyl, 3-naphtho- [2,3-b ] -benzothienyl, 4-naphtho- [2,3-b ] -benzothienyl, 5-naphtho- [2,3-b ] -benzothienyl, 1-naphtho- [2,1-b ] -benzothienyl, 2-naphtho- [2,1-b ] -benzothienyl, 3-naphtho- [2,1-b ] -benzothienyl, 4-naphtho- [2,1-b ] -benzothienyl, 5-naphtho- [2,1-b ] -benzothienyl, 6-naphtho- [2,1-b ] -benzothienyl, 7-naphtho- [2,1-b ] -benzothienyl, 8-naphtho- [2,1-b ] -benzothienyl, 9-naphtho- [2,1-b ] -benzothienyl, 10-naphtho- [2,1-b ] -benzothienyl, 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, 6-benzo [3, 1-b ] -benzothienyl, 6-benzo [2, 1-d ] pyrimidinyl, 6-benzo [3, 1-b ] -benzothienyl, 2-benzofuro [3,2-d ] pyrimidinyl, 6-benzofuro [3,2-d ] pyrazinyl, 7-benzofuro [3,2-d ] pyrazinyl, 8-benzofuro [3,2-d ] pyrazinyl, 9-benzofuro [ 2-d ] 2-d-naphtyl, 6-benzofurano [2, 2-d ] pyrazinyl, 6-b-benzofurano [ 2-d-b ] 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-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. In the present disclosure, "halogen" includes F, cl, br and I.

In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2 or positions 2 and 3. Meta-position means that two substituents are at positions 1 and 3 and is referred to as meta-position, for example, when two substituents in the benzene derivative occupy positions 1 and 3. Para represents two substituents at positions 1 and 4, and is referred to as para, for example, when two substituents in the benzene derivative occupy positions 1 and 4.

The expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced with a group formed by the connection of two or more substituents among the above-mentioned substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as a heteroaryl substituent or a substituent in which two heteroaryl substituents are linked. In the present disclosure, one or more substituents of the substituted aryl, substituted heteroaryl, substituted dibenzofuranyl, substituted dibenzothiophenyl, and substituted carbazolyl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; 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-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl; a (C6-C30) aryl group unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; 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-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; unsubstituted or deuterium-substituted (5-to 20-membered) heteroaryl; and (C6-C28) aryl unsubstituted or substituted with at least one of deuterium and (C6-C18) aryl. According to another embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; unsubstituted or deuterium-substituted (5-to 15-membered) heteroaryl; and (C6-C20) aryl unsubstituted or substituted with at least one of deuterium and (C6-C12) aryl. For example, the one or more substituents may each independently be deuterium; or may be at least one selected from the group consisting of: phenyl, naphthyl, triphenylenyl, phenanthryl, dibenzofuranyl, and dibenzothiophenyl, which may be further substituted with deuterium, unsubstituted or substituted with one or more phenyl groups.

In the formulas of the present disclosure, when a ring is formed by the attachment of adjacent substituents, the ring may be a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof, the ring being formed by the attachment of at least two adjacent substituents. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is 5 to 20. According to another embodiment of the present disclosure, the number of ring backbone atoms is 5 to 15.

In the formulas of the present disclosure, each heteroaryl group independently may contain at least one heteroatom selected from B, N, O, S, si, and P. Furthermore, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 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, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.

The present disclosure provides an organic electroluminescent compound represented by the above formula 1-1.

Hereinafter, the compound represented by formula 1-1 will be described in more detail.

In formula 1-1, X ₁ To X ₃ Each independently represents N or CR _a The method comprises the steps of carrying out a first treatment on the surface of the Provided that X ₁ To X ₃ Is N. According to one embodiment of the present disclosure, X ₁ To X ₃ N can be represented.

In formula 1-1, R _a Represents hydrogen or deuterium.

In formula 1-1, ar ₁ To Ar ₃ Each independently represents a (C6-C30) aryl group which is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group; provided that Ar is ₁ To Ar ₃ Are different from each other, and the naphthalene-containing structure and the following structure are excluded.

According to one embodiment of the present disclosure, ar ₁ To Ar ₃ May each independently represent a (C6-C28) aryl group that is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group. According to another embodiment of the present disclosure, ar ₁ To Ar ₃ May each independently represent a (C6-C25) aryl group unsubstituted or substituted with at least one of deuterium and a (C6-C20) aryl group. For example, ar ₁ To Ar ₃ Phenyl groups which may each independently be unsubstituted or substituted with one or more triphenylene groups; a biphenyl group; a terphenyl group; tetrabiphenyl, etc., which may be further substituted with deuterium.

According to yet another embodiment of the present disclosure, ar ₁ To Ar ₃ Each independently may represent an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted tetraphenyl group, an unsubstituted or deuterium-substituted phenylnaphthyl group, an unsubstituted or deuterium-substituted naphthylphenyl group, an unsubstituted or deuterium-substituted triphenylene group, an unsubstituted or deuterium-substituted phenanthryl group, or a combination thereof.

According to another embodiment of the present disclosure, ar ₁ To Ar ₃ May be different from each other.

According to one embodiment of the present disclosure, when the compound having formula 1-1 contains deuterium, its deuterium substitution rate may be about 30% to about 100%, preferably about 50% to about 100%, and more preferably about 70% to about 100%. The compound having the formula 1-1 having the deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.

The compound represented by formula 1-1 may be selected from the following compounds, but is not limited thereto.

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In the above compounds, dn means that n number of hydrogen atoms are replaced with deuterium.

The present disclosure provides an organic electroluminescent material comprising an organic electroluminescent compound represented by formula 1-1, and an organic electroluminescent device comprising the same.

The organic electroluminescent material may consist of only the organic electroluminescent compound according to the present disclosure, or may further comprise conventional materials included in the organic electroluminescent material.

The organic electroluminescent compound having formula 1-1 according to the present disclosure may be included in at least one layer of 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 intermediate layer, a hole blocking layer, and an electron blocking layer, preferably, as a host material of the light emitting layer.

The plurality of host materials according to the present disclosure include a first host material and a second host material, wherein the first host material includes at least one compound represented by formula 1, and the second host material includes at least one compound represented by formula 2, wherein at least one of the first host compound represented by formula 1 and the second host compound represented by formula 2 contains deuterium.

In formula 1, X ₁ To X ₃ Each independently represents N or CR _a The method comprises the steps of carrying out a first treatment on the surface of the Provided that X ₁ To X ₃ Is N. According to one embodiment of the present disclosure, X ₁ To X ₃ N can be represented.

In formula 1, R _a Represents hydrogen or deuterium.

In formula 1, ar ₁ To Ar ₃ Each independently represents a (C6-C30) aryl group which is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group. According to one of the present disclosureIn one embodiment, ar ₁ To Ar ₃ Each independently represents a (C6-C28) aryl group, wherein the (C6-C28) aryl group may be unsubstituted or substituted with at least one of deuterium and (C6-C25) aryl groups which are unsubstituted or substituted with one or more (C6-C12) aryl groups. According to another embodiment of the present disclosure, ar ₁ To Ar ₃ Each independently represents a (C6-C25) aryl group, wherein the (C6-C25) aryl group may be unsubstituted or substituted with at least one of deuterium and (C6-C20) aryl groups which are unsubstituted or substituted with one or more (C6-C10) aryl groups. For example, ar ₁ To Ar ₃ Phenyl groups which may each independently be unsubstituted or substituted with one or more triphenylene groups, one or more phenanthryl groups, or one or more phenylphenanthryl groups; a biphenyl group; a terphenyl group; tetrabiphenyl, etc., which may be further substituted with deuterium.

According to another embodiment of the present disclosure, ar ₁ To Ar ₃ Each independently may represent an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted tetrabiphenyl group, an unsubstituted or deuterium-substituted naphthyl group, an unsubstituted or deuterium-substituted phenylnaphthyl group, an unsubstituted or deuterium-substituted naphthylphenyl group, an unsubstituted or deuterium-substituted triphenylenyl group, an unsubstituted or deuterium-substituted phenanthryl group, or a combination thereof.

According to one embodiment of the present disclosure, when the compound having formula 1 contains deuterium, its deuterium substitution rate may be about 30% to about 100%, preferably about 50% to about 100%, and more preferably about 70% to about 100%. The compound having formula 1 having the deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.

Hereinafter, the compound represented by formula 2 will be described in more detail.

In formula 2, A ₁ And A ₂ Each of which is a single pieceIndependently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group. According to one embodiment of the present disclosure, A ₁ And A ₂ Each independently represents a (C6-C25) aryl group unsubstituted or substituted with at least one of deuterium, (C6-C30) aryl, and (6-to 25-membered) heteroaryl; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and (C6-C20) aryl; dibenzothienyl, unsubstituted or substituted with at least one of deuterium and (C6-C20) aryl; or a carbazolyl group which is unsubstituted or substituted with at least one of deuterium and (C6-C25) aryl. According to another embodiment of the present disclosure, A ₁ And A ₂ (C6-C20) aryl groups which may each independently represent an (C6-C20) aryl group which is unsubstituted or substituted with at least one of deuterium, (C6-C20) aryl groups, and (6-to 15-membered) heteroaryl groups; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and (C6-C10) aryl; dibenzothienyl, unsubstituted or substituted with at least one of deuterium and (C6-C10) aryl; or a carbazolyl group which is unsubstituted or substituted with at least one of deuterium and (C6-C15) aryl. For example, A ₁ And A ₂ Phenyl groups which may each independently be unsubstituted or substituted with at least one of naphthyl, triphenylenyl, dibenzofuranyl, and dibenzothiophenyl; a biphenyl group; a terphenyl group; naphthyl, unsubstituted or substituted with one or more phenyl groups; triphenylene; dibenzofuranyl, unsubstituted or substituted with one or more phenyl groups; dibenzothienyl, unsubstituted or substituted with one or more phenyl groups; carbazolyl groups or the like, unsubstituted or substituted with one or more phenyl groups, or one or more naphthyl groups, which may be further substituted with deuterium.

According to another embodiment of the present disclosure, A ₁ And A ₂ Can each independently represent phenyl unsubstituted or substituted by deuterium, biphenyl unsubstituted or substituted by deuterium, terphenyl unsubstituted or substituted by deuterium, naphthyl unsubstituted or substituted by deuterium, fluorenyl unsubstituted or substituted by at least one of deuterium, (C1-C30) alkyl and (C6-C30) aryl, fluorenyl unsubstituted or substituted by deuterium, (C1-C30) alkyl andat least one substituted benzofluorenyl group of the (C6-C30) aryl groups, an unsubstituted or deuterium-substituted triphenylenyl group, an unsubstituted or deuterium-substituted fluoranthenyl group, an unsubstituted or deuterium-substituted phenanthrenyl group, an unsubstituted or deuterium-substituted dibenzofuranyl group, an unsubstituted or deuterium-substituted carbazolyl group, an unsubstituted or deuterium-substituted dibenzothiophenyl group, or a combination thereof.

In formula 2, X ₁₅ To X ₁₈ Any one of which is combined with X ₁₉ To X ₂₂ Any one of which are connected to each other to form a single bond; and X does not form a single bond ₁₁ To X ₁₄ 、X ₂₃ To X ₂₆ And X ₁₅ To X ₂₂ Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings. For example, X ₁₅ To X ₁₈ Any one of which is combined with X ₁₉ To X ₂₂ Any of which may be connected to each other to form a single bond; and X does not form a single bond ₁₁ To X ₁₄ 、X ₂₃ To X ₂₆ And X ₁₅ To X ₂₂ May each independently be hydrogen, deuterium, or the like.

According to another embodiment of the present disclosure, X ₁₁ 、X ₁₈ 、X ₁₉ And X ₂₆ At least one, preferably at least two, more preferably at least three, and even more preferably all, of the (c) may be deuterium.

According to one embodiment of the present disclosure, X ₁₁ To X ₂₆ May have deuterium substitution rates of about 25% to about 100%, preferably about 35% to about 100%, more preferably about 45% to about 100%, and even more preferably about 55% to about 100%.

According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas 2-1 to 2-8.

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In the formulae 2-1 to 2-8, A ₁ 、A ₂ And X ₁₁ To X ₂₆ Is as defined in formula 2.

According to one embodiment of the present disclosure, when the compound having formula 2 contains deuterium, its deuterium substitution rate may be about 40% to about 100%, preferably about 50% to about 100%, more preferably about 60% to about 100%, and even more preferably about 70% to about 100%. The compound having formula 2 having the deuterium substitution rate may increase bond dissociation energy due to deuteration, thereby increasing stability of the compound, and the organic electroluminescent device including the compound may exhibit improved lifetime characteristics.

According to one embodiment of the present disclosure, formula 1 may not contain deuterium, and formula 2 may contain deuterium.

The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.

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The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.

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The combination of at least one of the compounds C-1 to C-377 and at least one of the compounds H2-1 to H2-290 may be used in an organic electroluminescent device.

The compounds represented by formulas 1-1 and 1 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, by referring to the following reaction scheme 1, but are not limited thereto.

Reaction scheme 1

In reaction scheme 1, X ₁ To X ₃ And Ar is a group ₁ To Ar ₃ Each as defined in formula 1.

The compound represented by formula 2 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, by referring to the following reaction scheme 2, but is not limited thereto.

Reaction scheme 2

In reaction scheme 2, A ₁ 、A ₂ 、X ₁₁ To X ₂₆ And n is as defined in formula 2, and Dn means that n number of hydrogen atoms are replaced by deuterium.

Although illustrative synthetic examples of the compounds represented by formulas 1-1, 1 and 2 are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartmash (Buchwald-Hartwig) cross-coupling reactions, N-arylation reactions, acidified montmorillonite (H-mont) -mediated etherification reactions, miyaura) boronation reactions, suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, pd (II) -catalyzed oxidative cyclization reactions, grignard reactions (Grignard Reaction), heck reactions (Heck reactions), dehydrative cyclization reactions, SN ₁ Substitution reaction, SN ₂ Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and the above reaction proceeds even when substituents defined by formulas 1-1, and 2 but not specified in specific synthetic examples are bonded.

Furthermore, deuterated compounds having formulas 1-1, and 2 may be prepared in a similar manner using deuterated precursor materials or more generally by treating non-deuterated compounds with deuterated solvent D6-benzene in the presence of a lewis acid H/D exchange catalyst such as aluminum trichloride or ethylaluminum chloride. In addition, the degree of deuteration can be controlled by varying the reaction conditions, such as the reaction temperature. For example, the number of deuterium atoms in formulas 1-1, 1 and 2 can be controlled by adjusting the reaction temperature and time, the equivalent weight of the acid, and the like.

The present disclosure provides an organic electroluminescent device including an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of host materials according to the present disclosure. The first host material and the second host material according to the present disclosure may be contained in one light emitting layer or in different light emitting layers among a plurality of light emitting layers, respectively. A variety of host materials according to the present disclosure may comprise a compound represented by formula 1 and a compound represented by formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70:30. Further, the compound represented by formula 1 and the compound represented by formula 2 may be combined at a desired ratio by mixing them after placing them in a shaker, by placing them in a glass tube and dissolving them by applying heat, and then collecting them, or by dissolving them in a solvent or the like.

According to one embodiment of the present disclosure, the dopant compound may have a doping concentration of less than 20wt% relative to the host compound in the light emitting layer. The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but may be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably ortho-metallized complex compounds selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.

The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following formula 101, but is not limited thereto.

In the case of the method 101,

l is any one selected from the following structures 1 to 3:

R ₁₀₀ to R ₁₀₃ Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, substituted or unsubstituted (C3)-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to adjacent substituents to form together with pyridine one or more rings, such as substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline;

R ₁₀₄ to R ₁₀₇ Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to adjacent substituents to form together with benzene one or more substituted or unsubstituted rings, for example, substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothiophenopyridine;

R ₂₀₁ To R ₂₂₀ Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted with deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to adjacent substituents to form one or more substituted or unsubstituted rings; and is also provided with

s represents an integer of 1 to 3.

Specific examples of the dopant compounds are as follows, but are not limited thereto.

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The organic electroluminescent device according to the present disclosure includes an anode; a cathode; and at least one organic layer interposed between the anode and the cathode. The organic layer comprises a light emitting layer and may further comprise at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of these layers may be further configured as several layers.

The anode and cathode may each be formed of a transparent conductive material, or a transflective or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type according to the type of materials forming the anode and the cathode. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

The organic layer may further include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: a group 1 metal, a group 2 metal, a transition metal of period 4, a transition metal of period 5, an organometallic of a lanthanide and a d-transition element, or at least one complex compound comprising such a metal.

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

In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer may be preferably placed on one or more inner surfaces of one or both electrodes. In particular, a silicon or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. The surface layer may provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide comprises SiO _X (1≤X≤2)、AlO _X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like; the metal halide comprises LiF, mgF ₂ 、CaF ₂ Rare earth metal fluorides, etc.; and the metal oxide includes Cs ₂ O、Li ₂ O, mgO, srO, baO, caO, etc.

A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer so as to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayer. The hole transport layer or the electron blocking layer may be a multilayer.

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 a multilayer in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein two compounds may be simultaneously used in each of the multilayer. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein a plurality of compounds may be used in each of the multilayer.

The light emitting auxiliary layer is a layer placed between the anode and the light emitting layer or between the cathode and the light emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to promote hole injection and/or transport or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to facilitate electron injection and/or transport or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer to exhibit an effect of promoting or blocking a hole transport rate (or injection rate), thereby enabling control of charge balance. An electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and may block electrons from the light emitting layer from overflowing and confine excitons in the light emitting layer to prevent light leakage. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer has an effect of improving efficiency and/or lifetime of the organic electroluminescent device.

In the organic electroluminescent device of the present disclosure, it is preferable that a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant is disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus injection and transport of electrons from the mixing region to the electroluminescent medium becomes easier. Furthermore, the hole transporting compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the electroluminescent medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds; and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers emitting white light.

According to one embodiment of the present disclosure, an organic electroluminescent material may be used as a light emitting material for a white organic light emitting device. Various structures of a white organic light emitting device have been proposed, such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light emitting members, or a Color Conversion Material (CCM) method, or the like. Furthermore, the organic electroluminescent material according to the present disclosure may also be used in an organic electroluminescent device comprising Quantum Dots (QDs).

Each layer of the organic electroluminescent device of the present disclosure may be formed by any one of the following methods: dry film forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. The first host compound and the second host compound according to the present disclosure may be formed into a film by a co-evaporation method or a mixture evaporation method.

When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer is soluble or dispersible and which has no problem in terms of film forming ability.

Further, a display system, for example, a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using the organic electroluminescence device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.

Hereinafter, a method of preparing the compound of the present disclosure and physical characteristics thereof, and a driving voltage and light emitting efficiency of an organic electroluminescent device (OLED) including a plurality of host materials according to the present disclosure will be explained in detail with reference to representative compounds of the present disclosure. However, the following examples merely explain the characteristics of the compounds according to the present disclosure and the OLED including the same, and the present disclosure is not limited to the following examples.

Example 1: preparation of Compound C-109

Synthesis of Compounds 1-2

In a reaction vessel, (3-chlorophenyl) boric acid (2.6 g,16.67 mmol), compound 1-1 (7 g,16.67 mmol), tetrakis (triphenylphosphine) palladium (5.8 mg,0.5 mmol), and potassium carbonate (5.8 g,41.7 mmol) were dissolved in 83mL of toluene, 21mL of ethanol, and 21mL of water, and stirred under reflux for 4 hours. After cooling to room temperature, water was added to the reaction in which the solid formed, and stirred for 30 minutes, followed by filtration. The filtrate was separated by column chromatography to obtain compound 1-2 (5.3 g, yield: 64%).

Synthesis of Compound C-109

In a reaction vessel, compound 1-2 (5.3 g,10.7 mmol), [1,1' -biphenyl ] -3-ylboronic acid (2.54 g,12.82 mmol), palladium acetate (0.25 g,1.07 mmol), S-Phos (0.88 g,2.14 mmol), and sodium tert-butoxide (3.1 g,32.0 mmol) were dissolved in 53mL of o-xylene, 13mL of 1, 4-dioxane, and 13mL of water, and stirred under reflux for 4 hours. After cooling to room temperature, water was added to the reaction in which the solid formed, and stirred for 30 minutes, followed by filtration. The filtrate was separated by column chromatography to obtain compound C-109 (2.9 g, yield: 44%).

Compounds of formula (I)	MW	Melting point
			C-109	612.8	199

Example 2: preparation of Compound C-198

Synthesis of Compound 2-1

In a reaction vessel, 3-chloro-1, 1' -biphenyl (18 g,63.9 mmol), (3-chlorophenyl) boronic acid (10 g,63.9 mmol), tetrakis (triphenylphosphine) palladium (3.7 mg,3.2 mmol), and potassium carbonate (22 g,191 mmol) were dissolved in 320mL of toluene, 160mL of ethanol, and 160mL of water, and stirred under reflux for 4 hours. After cooling to room temperature, water was added to the reaction in which the solid formed, and stirred for 30 minutes, followed by filtration. The filtrate was separated by column chromatography to obtain compound 2-1 (15 g, yield: 89%).

Synthesis of Compound 2-2

In a reaction vessel, compound 2-1 (6 g,32.7 mmol), bis (pinacolato) diboron (11.5 g,45.4 mmol), tris (dibenzylideneacetone) dipalladium (0) (2.1 g,2.27 mmol), S-Phos (2.7 g,6.54 mmol), and potassium acetate (6.7 g,68.1 mmol) were dissolved in 110mL of 1, 4-dioxane and stirred under reflux for 3 hours. After the reaction was completed, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator, followed by purification by column chromatography to obtain compound 2-2 (10 g, yield: 87%).

Synthesis of Compound C-198

In a reaction vessel, compound 2-2 (8 g,22.4 mmol), compound 2-3 (7.8 g,18.7 mmol), palladium acetate (420 mg,1.8 mmol), S-Phos (1.5 g,3.7 mmol), and cesium carbonate (18 g,56.1 mmol) were dissolved in 93mL of toluene, 23mL of ethanol, and 23mL of water, and stirred under reflux for 4 hours. After cooling to room temperature, water was added to the reaction in which the solid formed, and stirred for 30 minutes, followed by filtration. The filtrate was separated by column chromatography to obtain compound C-198 (3.3 g, yield: 30%).

Compounds of formula (I)	MW	Melting point
			C-198	613.2	185.4

Example 3: preparation of Compound C-28

In a flask, compound 3-1 (6.0 g,21.89 mmol), 2- ([ 1,1 '-biphenyl ] -3-yl) -4- ([ 1,1' -biphenyl ] -4-yl) -6-chloro-1, 3, 5-triazine (7.6 g,18.24 mmol), tetrakis (triphenylphosphine) palladium (0.7 g,0.55 mmol), and potassium carbonate (6.3 g,45.60 mmol) were dissolved in 91mL toluene, 23mL ethanol, and 23mL distilled water, and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and separated by column chromatography to obtain compound C-28 (3.3 g, yield: 30%).

Compounds of formula (I)	MW	Melting point
			C-28	613.75	220℃

Example 4: preparation of Compound C-266

In a flask, 2, 4-bis ([ 1,1 '-biphenyl ] -4-yl) -6-chloro-1, 3, 5-triazine (5 g,11.91 mmol), [1,1' -biphenyl ] -4-ylboronic acid (2.6 g,13.09 mmol), tetrakis (triphenylphosphine) palladium (0.688 g,0.595 mmol), and sodium carbonate (4.1 g,29.77 mmol) were dissolved in 100mL of toluene, 50mL of ethanol, and 50mL of distilled water, and stirred under reflux for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate, and separated by column chromatography to obtain compound C-266 (5.5 g, yield: 86%).

Compounds of formula (I)	MW	Melting point
			C-266	537.67	265.9℃

Example 5: preparation of Compound C-199

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Compound 5-1 (3.4 g,5.95 mmol), compound 5-2 (1.2 g,5.95 mmol), tetrakis (triphenylphosphine) palladium (343 mg,0.29 mmol), potassium carbonate (2.5 g,17.85 mmol), 30mL of toluene, 15mL of ethanol, and 15mL of distilled water were added to the reaction vessel, and stirred at 120℃for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-199 (1.9 g, yield: 46%).

Compounds of formula (I)	MW	Melting point
			C-199	689.86	232℃

Example 6: preparation of Compound C-370

Compound 6-1 (5 g,11.56 mmol), compound 6-2 (5.3 g,12.72 mmol), tetrakis (triphenylphosphine) palladium (400 mg,0.35 mmol), potassium carbonate (4 g,28.91 mmol), 57mL of toluene, 14mL of ethanol, and 14mL of distilled water were added to the reaction vessel, and stirred at 120℃for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-370 (4.9 g, yield: 61%).

Compounds of formula (I)	MW	Melting point
			C-370	689.86	302.7℃

Example 7: preparation of Compound C-17

Compound 7-1 (5 g,10.08 mmol), compound 7-2 (3.3 g,12.10 mmol), tetrakis (triphenylphosphine) palladium (350 mg,0.30 mmol), potassium carbonate (3.5 g,25.20 mmol), 50mL of toluene, 13mL of ethanol, and 13mL of distilled water were added to the reaction vessel, and stirred at 120℃for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-17 (3.4 g, yield: 49%).

Compounds of formula (I)	MW	Melting point
			C-17	689.86	243℃

Example 8: preparation of Compound C-371

Compound 8-1 (5 g,11.91 mmol), compound 8-2 (5.2 g,11.91 mmol), tetrakis (triphenylphosphine) palladium (410 mg,0.30 mmol), potassium carbonate (4.1 g,29.77 mmol), 60mL of toluene, 15mL of ethanol, and 15mL of distilled water were added to the reaction vessel, and stirred at 120℃for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-371 (5.5 g, yield: 67%).

Compounds of formula (I)	MW	Melting point
			C-371	689.86	242℃

Example 9: preparation of Compound C-372

In a reaction vessel, compound 9-1 (7.1 g,14.30 mmol), compound 9-2 (6.5 g,21.30 mmol), tris (dibenzylideneacetone) dipalladium (651 mg,0.7 mmol), S-Phos (587 mg,1.4 mmol), and potassium phosphate (9.1 g,42.8 mmol) were dissolved in 100mL of xylene and stirred at 160℃for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-372 (2.1 g, yield: 23%).

Compounds of formula (I)	MW	Melting point
			C-372	637.79	215℃

Example 10: preparation of Compound C-373

Compound 10-1 (7.66 g,18.2 mmol), compound 10-2 (5.00 g,18.2 mmol), tetrakis (triphenylphosphine) palladium (292 mg,0.547 mmol), potassium carbonate (7.56 g,54.7 mmol), 500mL of toluene, 100mL of ethanol, and 100mL of distilled water were added to the reaction vessel, and stirred at 120℃for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-373 (6.7 g, yield: 60%).

Compounds of formula (I)	MW	Melting point
			C-373	613.75	358℃

Example 11: preparation of Compound C-374

Compound 11-1 (7.66 g,18.2 mmol), compound 11-2 (5.00 g,18.2 mmol), tetrakis (triphenylphosphine) palladium (292 mg,0.547 mmol), potassium carbonate (7.56 g,54.7 mmol), 500mL of toluene, 100mL of ethanol, and 100mL of distilled water were added to the reaction vessel, and stirred at 120℃for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-374 (6.7 g, yield: 14%).

Compounds of formula (I)	MW	Melting point
			C-374	613.75	232℃

Example 12: preparation of Compound C-375

Compound 12-1 (7.66 g,18.2 mmol), compound 12-2 (5.00 g,18.2 mmol), tetrakis (triphenylphosphine) palladium (292 mg,0.547 mmol), potassium carbonate (7.56 g,54.7 mmol), 500mL of toluene, 100mL of ethanol, and 100mL of distilled water were added to the reaction vessel, and stirred at 120℃for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-375 (3.7 g, yield: 33%).

Compounds of formula (I)	MW	Melting point
			C-375	613.75	192.8℃

Example 13: preparation of Compound C-376

Compound 13-1 (7.66 g,18.2 mmol), compound 13-2 (5.00 g,18.2 mmol), tetrakis (triphenylphosphine) palladium (292 mg,0.547 mmol), potassium carbonate (7.56 g,54.7 mmol), 500mL of toluene, 100mL of ethanol, and 100mL of distilled water were added to the reaction vessel, and stirred at 120℃for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-376 (3.2 g, yield: 29%).

Compounds of formula (I)	MW	Melting point
			C-376	613.75	245.9℃

Example 14: preparation of Compound C-377

Compound 14-1 (3.4 g,6.854 mmol), compound 14-2 (1.88 g,6.854 mmol), tetrakis (triphenylphosphine) palladium (400 mg, 0.348 mmol), potassium carbonate (2.8 g,20.56 mmol), 40mL of toluene, 10mL of ethanol, and 10mL of distilled water were added to the reaction vessel, and stirred at 120℃for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator, followed by purification by column chromatography to obtain compound C-377 (3.3 g, yield: 69%).

Compounds of formula (I)	MW	Melting point
			C-377	689.8	235℃

Device examples 1 to 4: producing an OLED comprising a plurality of host materials according to the present disclosure

An OLED according to the present disclosure was produced. Transparent electrode Indium Tin Oxide (ITO) film (10Ω/s) on glass substrate for OLEDq) (gematec co., ltd., japan (Japan Ji Aoma limited)) is sequentially subjected to ultrasonic washing with acetone and isopropanol, and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 of Table 3 was introduced into one cell of a vacuum vapor deposition apparatus and the compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates, and compound HI-1 was deposited in a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby depositing a second hole transport layer having a thickness of 30nm 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 first host compound and the second host compound shown in table 1 below were introduced as hosts into two cells of a vacuum vapor deposition apparatus, and compound D-130 was introduced as a dopant into the other cell. The two host materials were evaporated at a rate of 1:2 (first host: second host) and the dopant materials were simultaneously evaporated at different rates, and the dopant was deposited at a doping amount of 10wt% based on the total of the host and the dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. The compound ETL-1 and the compound EIL-1 were evaporated as electron transport materials in a weight ratio of 40:60 to deposit an electron transport layer having a thickness of 35nm on the light emitting layer. After depositing the compound EIL-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thereby, an OLED is produced. Each compound for each material was prepared by mixing at 10 a ^-6 Purification was performed by vacuum sublimation under the tray.

Device examples 5 to 13: producing an OLED comprising a plurality of host materials according to the present disclosure

An OLED was produced in the same manner as in device example 1, except that the first host compound shown in table 1 below was used as a host of the light-emitting layer, and compound D-150 was used as a dopant.

Comparative example 1: production of OLED containing conventional Compounds

An OLED was produced in the same manner as in device example 1, except that the first host compound and the second host compound shown in table 1 below were used as the hosts of the light-emitting layer.

The driving voltage, the luminous efficiency and the luminous color of the OLEDs produced in device examples 1 to 13 and comparative example 1 at a luminance of 1,000 nit and the time taken for the luminance to decrease from 100% to 80% at a luminance of 60,000 nit (lifetime: T80) are provided in table 1 below.

TABLE 1

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As can be confirmed from table 1 above, the OLEDs (device examples 1 to 13) comprising the plurality of host materials according to the present disclosure exhibited excellent lifetime characteristics as well as lower driving voltages and higher luminous efficiencies, as compared to the OLED (comparative example 1) comprising the conventional host combination. Due to the low efficiency, it was not possible to measure the lifetime of the OLED according to comparative example 1.

The lifetime of an OLED emitting green light is typically shorter than the lifetime of an OLED emitting red light. In order to improve the lifetime characteristics of green light emitting OLEDs, the present disclosure uses compounds into which deuterated moieties are introduced. While not being limited by theory, when the organic electroluminescent compound is substituted with deuterium, the zero point vibration energy of the compound is reduced, thereby increasing the Bond Dissociation Energy (BDE) of the compound and thus increasing the stability of the compound.

Device examples 14 to 16: producing an OLED comprising a compound according to the present disclosure as a unitary host material

An OLED was produced in the same manner as in device example 1, except that only the compounds shown in table 2 below were used as a single body of the light-emitting layer.

Device examples 17 to 25: producing an OLED comprising a compound according to the present disclosure as a unitary host material

An OLED was produced in the same manner as in device example 1, except that only the compound shown in table 2 below was used as a single host of the light-emitting layer, and compound D-150 was used as a dopant.

Comparative examples 2 to 4: production of OLED comprising conventional compounds as unitary host material

An OLED was produced in the same manner as in device example 1, except that only the compounds shown in table 2 below were used as the host of the light-emitting layer.

The driving voltages and emission colors of the OLEDs produced in device examples 14 to 25 and comparative examples 2 to 4 at a luminance of 1,000 nit and the time taken for the luminance to decrease from 100% to 80% at a luminance of 60,000 nit (lifetime: T80) are provided in table 2 below.

TABLE 2

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As can be confirmed from table 2 above, the OLEDs (device examples 14 to 25) comprising the compounds according to the present disclosure as host materials exhibited excellent lifetime characteristics compared to the OLEDs (comparative examples 2 to 4) comprising the conventional compounds as host materials.

The compounds used in the device examples and comparative examples are shown in table 3 below.

TABLE 3

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Claims

1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2, and wherein at least one of the first host compound and the second host compound contains deuterium:

in the formula (1) of the present invention,

R _a represents hydrogen or deuterium; and is also provided with

In the formula (2) of the present invention,

2. The plurality of host materials of claim 1, wherein the substituents of the substituted aryl, the substituted heteroaryl, the substituted dibenzofuranyl, the substituted dibenzothiophenyl, and the substituted carbazolyl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; 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-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-to 30-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl; a (C6-C30) aryl group unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; 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-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.

3. The plurality of host materials of claim 1, wherein Ar of formula 1 ₁ To Ar ₃ Each independently is an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted tetraphenyl group, an unsubstituted or deuterium-substituted naphthyl group, an unsubstituted or deuterium-substituted phenyl naphthyl group, an unsubstituted or deuterium-substituted naphthyl phenyl group, an unsubstituted or deuterium-substituted triphenylenyl group, an unsubstituted or deuterium-substituted phenanthryl group, or a combination thereof.

4. The plurality of host materials of claim 1, wherein Ar of formula 1 ₁ To Ar ₃ Are all different from each other.

5. The plurality of host materials of claim 1, wherein formula 1 contains no deuterium and formula 2 contains deuterium.

6. The plurality of host materials of claim 1, wherein the compound represented by formula 1 has a deuterium substitution rate of 30% to 100%.

7. The plurality of host materials of claim 1, wherein X in formula 2 ₁₁ 、X ₁₈ 、X ₁₉ And X ₂₆ At least one of which is deuterium.

8. The plurality of host materials of claim 1, wherein the compound represented by formula 2 has a deuterium substitution rate of 40% to 100%.

9. The plurality of host materials of claim 1, wherein X in formula 2 ₁₁ To X ₂₆ The deuterium substitution rate of (2) is 25% to 100%.

10. The plurality of host materials of claim 1, wherein formula 2 is represented by any one of the following formulas 2-1 to 2-8:

in formulas 2-1 to 2-8,

A ₁ 、A ₂ and X ₁₁ To X ₂₆ Is as defined in claim 1.

11. The plurality of host materials of claim 1, wherein a of formula 2 ₁ And A ₂ Each independently is phenyl unsubstituted or substituted with deuterium; biphenyl group unsubstituted or substituted with deuterium; a terphenyl group unsubstituted or substituted with deuterium; naphthyl, unsubstituted or substituted with deuterium; fluorenyl unsubstituted or substituted with at least one of deuterium, (C1-C30) alkyl, and (C6-C30) aryl; benzofluorenyl unsubstituted or substituted with at least one of deuterium, (C1-C30) alkyl, and (C6-C30) aryl; triphenylene unsubstituted or substituted with deuterium; a fluoranthenyl group that is unsubstituted or substituted with deuterium; phenanthryl unsubstituted or substituted with deuterium; dibenzofuranyl, unsubstituted or substituted with deuterium; carbazolyl group unsubstituted or substituted with deuterium; dibenzothienyl, unsubstituted or substituted with deuterium; or a combination thereof.

12. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:

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where Dn means that n number of hydrogen atoms are replaced by deuterium.

13. The plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:

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where Dn means that n number of hydrogen atoms are replaced by deuterium.

14. An organic electroluminescent device, comprising: an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises the plurality of host materials according to claim 1.

15. An organic electroluminescent compound represented by the following formula 1-1:

in the case of the formula 1-1,

R _a represents hydrogen or deuterium; and is also provided with

Ar ₁ To Ar ₃ Each independently represents a (C6-C30) aryl group which is unsubstituted or substituted with at least one of deuterium and a (C6-C30) aryl group; provided that Ar is ₁ To Ar ₃ Different from each other, and excludes naphthalene-containing structures and the following structures:

16. according to claim 15An organic electroluminescent compound, wherein Ar of formula 1-1 ₁ To Ar ₃ Each independently is an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted tetraphenyl group, an unsubstituted or deuterium-substituted phenylnaphthyl group, an unsubstituted or deuterium-substituted naphthylphenyl group, an unsubstituted or deuterium-substituted triphenylenyl group, an unsubstituted or deuterium-substituted phenanthryl group, or a combination thereof.

17. The organic electroluminescent compound according to claim 15, wherein the compound represented by formula 1-1 is selected from the group consisting of:

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where Dn means that n number of hydrogen atoms are replaced by deuterium.

18. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 15.