Organic electroluminescent compound, plurality of host materials, and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound according to the present disclosure as a single host material or by comprising a specific combination of the compounds according to the present disclosure as a plurality of host materials, an organic electroluminescent device having improved driving voltage, luminous efficiency, and / or lifespan characteristics can be provided.

Description

[0001] Divisional Application Instructions

[0002] This application is a divisional application of the invention patent application filed on February 7, 2022, with national application number 202210133288.4, entitled "Organic electroluminescent compound, various host materials and organic electroluminescent device including the thereof". Technical Field

[0003] This disclosure relates to an organic electroluminescent compound, various host materials, and an organic electroluminescent device comprising the same. Background Technology

[0004] In 1987, Tang et al. of Eastman Kodak first developed a small-molecule green organic light-emitting diode (OLED) device using a TPD / Alq3 bilayer consisting of an emissive layer and a charge transport layer. Since then, OLED development has progressed rapidly, and OLEDs have been commercialized. Currently, organic light-emitting devices primarily utilize phosphorescent materials with excellent luminous efficiency in panel implementation. However, in many applications such as TVs and lighting equipment, the lifespan of OLEDs is insufficient, and higher-efficiency OLEDs are still needed. Generally speaking, the lifespan of an OLED decreases as its brightness increases. Therefore, for displays requiring long-term use and high resolution, OLEDs with high luminous efficiency and / or long lifespan are necessary.

[0005] Various materials or concepts for organic layers in organic electroluminescent devices have been proposed to improve luminous efficiency, driving voltage, and / or lifetime. However, they have not been satisfactory in practical applications.

[0006] Meanwhile, Korean Patent Application Publication No. 2016-0006633 and U.S. Patent Application Publication No. 2017-0054087 disclose a fluorene derivative compound. However, the aforementioned references do not specifically disclose any particular compound or specific combination of host materials claimed herein. Furthermore, there is a need to develop electroluminescent materials with improved performance (e.g., low driving voltage, high luminous efficiency, and / or improved lifetime characteristics) compared to the compounds disclosed in the aforementioned references. Summary of the Invention

[0007] Technical issues

[0008] The present disclosure aims to provide an organic electroluminescent compound having a novel structure suitable for application in organic electroluminescent devices. Another objective of the present disclosure is to provide an improved organic electroluminescent material capable of providing organic electroluminescent devices with improved driving voltage, luminous efficiency, and / or lifetime characteristics. Yet another objective of the present disclosure is to provide an organic electroluminescent device with improved driving voltage, luminous efficiency, and / or lifetime characteristics by comprising a specific combination of compounds as the host material.

[0009] Solution to the problem

[0010] As a result of in-depth research into solving the aforementioned technical problems, the inventors of this invention have discovered that the above-mentioned objective can be achieved by an organic electroluminescent compound represented by Formula 1'. Furthermore, the inventors of this invention have discovered that the above-mentioned objective can be achieved by a variety of host materials, including a first host material and a second host material, wherein the first host material comprises a compound represented by Formula 1, and the second host material comprises a compound represented by Formula 2.

[0011] ----- (1)

[0012] In Equation 1, R1 to R8 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -(L). a -HAr; At least one of R1 to R8 is -(L) a -HAr; HAr indicates a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group; L independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and 'a' represents 1 or 2; ----- (2) In Equation 2, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group. Ar1 to Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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, fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L b -N(Ar c (Ar) d ); L b This indicates a single-bonded, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3 to 30-membered) heteroarylene; and Ar c and Ar d Each of the following can independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl; The premise is to exclude the case where L1 to L3 are all single bonds and Ar1 to Ar3 are all hydrogens.

[0013] ----- (1')

[0014] In equation 1', R1 to R8 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -(L). a -HAr, provided that R1 to R8 are not 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl; At least one of R1 to R8 is -(L) a -HAr; HAr indicates a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group; L independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and 'a' represents 1 or 2; The prerequisite is that any one of R1 to R8 is -(L). a -HAr case; a is 1; L is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene; and HAr is a triazine group that is independently selected from any two of the following groups: phenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, excluding pyridyl groups substituted with phenyl. The prerequisite is that any one of R1 to R8 is -(L). a In the case of -HAr; a is 1; L is a single bond or pyridylene; HAr is a triazine group substituted by any two of the following groups, each independently selected: an unsubstituted or deuterated or 9,9-dimethylfluorenyl substituted phenyl, an unsubstituted or deuterated biphenyl, a phenyl-substituted pyridyl, an unsubstituted or deuterated 9,9-dimethylfluorenyl, 9,9-dimethylazafluorenyl, spiro[cyclohexane-1,9'-fluorenyl]yl, and 9,9'-spirodifluorenyl; and any one or two of the remaining R1 to R8 are unsubstituted phenyl or exclude unsubstituted biphenyl; and The premise is that organic electroluminescent compounds with the following structures are excluded.

[0015]

[0016] Beneficial effects of the present invention

[0017] The organic electroluminescent compounds according to this disclosure exhibit performance suitable for organic electroluminescent devices. Furthermore, by including an organic electroluminescent compound according to this disclosure as a single host material or by including a specific combination of compounds according to this disclosure as multiple host materials, an organic electroluminescent device is provided that, compared to conventional organic electroluminescent devices, has a lower driving voltage, higher luminous efficiency, and / or superior lifetime characteristics, and can be used to manufacture display devices or light-emitting devices. Detailed Implementation

[0018] This disclosure will be described in detail below. However, the following description is intended to explain this disclosure and is not intended to limit its scope.

[0019] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any layer constituting the organic electroluminescent device.

[0020] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0021] The term "multiple host materials" in this disclosure refers to one or more host materials comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. For example, the multiple host materials of this disclosure may be a combination of two or more host materials, which may optionally further include conventional materials included in organic electroluminescent materials. The two or more compounds included in the multiple host materials of this disclosure may be included together in a single light-emitting layer, or may be included separately in different light-emitting layers. For example, the two or more host materials may be co-evaporated or co-evaporated, or may be evaporated individually.

[0022] In this document, the term "(C1-C30)alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3- to 7-membered)heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7 cyclic skeleton atoms and containing at least one heteroatom, wherein the heteroatom is selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N. The aforementioned heterocyclic alkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)aryl" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton. The aforementioned aryl groups may be partially saturated and may contain spirostructures. The aforementioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, biphenylfluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], phenanthrene, phenylphenanthrene, benzo[phenanthrene], anthracene, indene, triphenylene, pyrene, tetraphenyl, peryl, thyl, naphthanoyl, fluoranyl, spirodifluorenyl, spiro[fluorenyl-benzo[fluorenyl]], spiro[cyclopentenyl-fluorenyl], spiro[dihydroindene-fluorenyl], azulenyl, tetramethyldihydrophenanthrene, etc. Specifically, aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzo[a]anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, naphthonaphthyl, pyrene, 1-phenyl, 2-phenyl, 3-phenyl, 4-phenyl, 5-phenyl, 6-phenyl, benzo[c]phenanthyl, benzo[g]phenyl, 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a] Fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzo[b]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-triphenyl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzo[b]fluoranthyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-Xylyl, mesitylene, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4'-tert-butyl-p-triphenyl-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 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-1 0-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-benzyl 1,11-dimethyl-7-benzo[b]fluorenyl, 1,11-dimethyl-8-benzo[b]fluorenyl, 1,11-dimethyl-9-benzo[b]fluorenyl, 1,11-dimethyl-10-benzo[b]fluorenyl, 1,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl [c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]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]fluorenyl, 11,11-diphenyl- 7-Benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl ]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-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthyl, etc.

[0023] The term "(3- to 30-membered) (hypo)aryl" refers to an aryl or aryl group having 3 to 30 ring skeleton atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Se. The aforementioned (hypo)aryl group may be a monocyclic ring or a fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a (hypo)aryl group formed by linking at least one heteroaryl group or an aryl group to a heteroaryl group via one or more single bonds; and it may contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazonyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and fused-ring heteroaryl groups, such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, di... Benzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuran-quinolinyl, benzofuran-quinazolinyl, benzofuran-naphthidyl, benzofuran-pyrimidyl, naphthofuran-pyrimidyl, benzothiophene-quinolinyl, benzothiophene-quinazolinyl, benzothiophene-naphthidyl, benzothiophene-pyrimidyl, naphthophene-pyrimidyl, pyrimidinyl Indole, benzopyrimidine-indole, benzofuran-pyrazinyl, naphthofuran-pyrazinyl, benzothiophene-pyrazinyl, naphthothiophene-pyrazinyl, pyrazin-indole, benzopyrazin-indole, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindole, indole, indole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazole Phinyl, quinoxalinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenanthidyl, benzodioxanepentenyl, dihydroacridinyl, benzotriazolephenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazole, indenecarbazole, etc. More specifically, heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, 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-indolidinyl, 2-indolidinyl, 3- Indolidyl, 5-indolidyl, 6-indolidyl, 7-indolidyl, 8-indolidyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl2-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 2-quinolinyl, 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-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 9-carbazoleyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole 8-yl, azacarbazolyl-9-yl, 1-phenanthrynyl, 2-phenanthrynyl, 3-phenanthrynyl, 4-phenanthrynyl, 6-phenanthrynyl, 7-phenanthrynyl, 8-phenanthrynyl, 9-phenanthrynyl, 10-phenanthrynyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl 5-Oxadiazolyl, 3-Furazolyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrolo-1-yl, 2-Methylpyrrolo-3-yl, 2-Methylpyrrolo-4-yl, 2-Methylpyrrolo-5-yl, 3-Methylpyrrolo-1-yl, 3-Methylpyrrolo-2-yl, 3-Methylpyrrolo-4-yl, 3-Methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-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 Furanyl, 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]-benzofuranyl [-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl,1-Naphtho-[2,3-b]-benzofuranyl, 2-Naphtho-[2,3-b]-benzofuranyl, 3-Naphtho-[2,3-b]-benzofuranyl, 4-Naphtho-[2,3-b]-benzofuranyl, 5-Naphtho-[2,3-b]-benzofuranyl, 6-Naphtho-[2,3-b]-benzofuranyl, 7-Naphtho-[2,3-b]-benzofuranyl ]-Benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4- Naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-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]-benzothiophene, 2-Naphtho-[1,2-b]-benzothiophene, 3-Naphtho-[1,2-b]-benzothiophene, 4-Naphtho-[1,2-b]-benzothiophene, 5-Naphtho-[1,2-b]-benzothiophene, 6-Naphtho-[1,2-b]-benzothiophene, 7-Naphtho-[1,2-b]-benzothiophene -[1,2-b]-benzothiophene, 8-naphtho-[1,2-b]-benzothiophene, 9-naphtho-[1,2-b]-benzothiophene, 10-naphtho-[1,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzyl 4-Naphtho-[2,3-b]-benzothiophene, 5-Naphtho-[2,3-b]-benzothiophene, 1-Naphtho-[2,1-b]-benzothiophene, 2-Naphtho-[2,1-b]-benzothiophene, 3-Naphtho-[2,1-b]-benzothiophene, 4-Naphtho-[2,1-b]-benzothiophene, 5-Naphtho-[ [2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2,1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 2-benzofurano[3,2-d]pyrimidine 6-benzofuran[3,2-d]pyrimidinyl, 7-benzofuran[3,2-d]pyrimidinyl, 8-benzofuran[3,2-d]pyrimidinyl, 9-benzofuran[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 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-Benzofuran[3,2-d]pyrazinyl, 6-Benzofuran[3,2-d]pyrazinyl, 7-Benzofuran[3,2-d]pyrazinyl, 8-Benzofuran[3,2-d]pyrazinyl, 9-Benzofuran[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzofuran[3,2-d]pyrazinyl Thio[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-germaniumfluorenyl, 2-germaniumfluorenyl, 3-germaniumfluorenyl, 4-germaniumfluorenyl, 1-dibenzo[3,2-d]selenophenyl, 2-dibenzo[3,2-d]selenophenyl, 3-dibenzo[3,2-d]selenophenyl, 4-dibenzo[3,2-d]selenophenyl, etc. In this disclosure, "halogen" includes F, Cl, Br, and I.

[0024] Furthermore, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that the two substituents are adjacent to each other, and for example, when the two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that the two substituents are at positions 1 and 3, and for example, when the two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that the two substituents are at positions 1 and 4, and for example, when the two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0025] The term "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent), and also includes the substitution of the hydrogen atom by a group formed by the linkage of two or more substituents. For example, "a group formed by the linkage of two or more substituents" could be pyridine-triazine. That is, pyridine-triazine can be interpreted as a heteroaryl substituent or a substituent in which two heteroaryl substituents are linked.In this disclosure, the substituted ()alkylene, the substituted alkenyl, the substituted ()aryl, the substituted ()heteroaryl, the substituted ()cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and one or more substituents of the fused ring group of one or more aliphatic rings and one or more aromatic rings are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halogenated ... 0) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocyclic alkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl; unsubstituted or substituted with at least one of deuterium and (C6-C30) heteroaryl; tri(C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C 30) Alkyl (C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; mono- or di-(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl (C2-C30)alkenylamino; (C1-C30)alkyl (C6-C30)arylamino; (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)arylphosphine; di(C6-C30)arylboroncarbonyl; di(C1-C30)alkylboroncarbonyl; (C1-C30)alkyl(C6-C30)arylboroncarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, each of the one or more substituents is independently at least one selected from the group consisting of: deuterium; (C1-C20)alkyl; unsubstituted (5- to 25-membered) heteroaryl group substituted with at least one of deuterium and (C6-C25) aryl group; unsubstituted (C6-C30) aryl group substituted with at least one of deuterium and (C6- to 25-membered) heteroaryl group; and di-(C6-C30) arylamino. According to another embodiment of the present disclosure, each of the one or more substituents is independently at least one selected from the group consisting of: deuterium; (C1-C10)alkyl; unsubstituted (5- to 25-membered) heteroaryl group substituted with at least one of deuterium and (C6-C18) aryl group; unsubstituted (C6-C30) aryl group substituted with at least one of deuterium and (C6- to 25-membered) heteroaryl group; and di-(C6-C12) arylamino. For example, one or more substituents may each independently be at least one selected from the group consisting of: deuterium; methyl; tert-butyl; unsubstituted or substituted with deuterium, one or more alkyl groups, one or more phenyl groups, or one or more 23-membered nitrogen-containing heteroaryl groups; unsubstituted or substituted with one or more alkyl groups; unsubstituted or substituted with deuterium; terphenyl; phenanthrene; phenylphenanthrene; unsubstituted or substituted with one or more phenyl groups, alkyl group; triphenylene; pyridyl; unsubstituted or substituted with one or more phenyl groups, carbazolyl; dibenzofuranyl; unsubstituted or substituted with deuterium, dibenzoselenyl; phenanthreneoxazolyl substituted with at least one of deuterium, unsubstituted or deuterium-substituted phenyl, and biphenyl; phenanthrenethiazolyl substituted with one or more phenyl groups; phenanthreneimidazolyl substituted with one or more phenyl groups; indolocarbazolyl substituted with one or more phenyl groups; 23-membered nitrogen-containing heteroaryl; and amino groups substituted with one or more phenyl groups.

[0026] In this document, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected or fused together to form a substituted or unsubstituted monocyclic or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof. The ring may preferably be a substituted or unsubstituted monocyclic or polycyclic (3- to 26-membered) alicyclic or aromatic ring, or a combination thereof, more preferably an unsubstituted or monocyclic (3- to 6-membered) alicyclic ring substituted with one or more (C1-C10) alkyl groups, or an unsubstituted or monocyclic or polycyclic (5- to 25-membered) aromatic ring substituted with at least one (C6-C18) aryl and (3- to 20-membered) heteroaryl groups. Furthermore, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, P, and Se, preferably at least one heteroatom selected from N, O, S, and Se. For example, the ring may be a benzene ring, an unsubstituted or cyclopentane ring substituted with one or more methyl groups, a fluorene ring, etc.

[0027] In this disclosure, each of the heteroaryl, heteroaryl, and heterocycloalkyl groups may independently contain at least one heteroatom selected from B, N, O, S, Si, P, and Se. 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 (3- 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)alkyl. 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- to 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- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30)-arylamino, substituted or unsubstituted (C2-C30) alkenyl (3- to 30-membered) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino.

[0028] The various host materials disclosed herein include a first host material and a second host material, wherein the first host material comprises at least one compound represented by Formula 1, and the second host material comprises at least one compound represented by Formula 2. The various host materials may be included in the light-emitting layer of an organic electroluminescent device according to an embodiment of the present disclosure.

[0029] The compounds represented by Formula 1 will be described in more detail below.

[0030] In Formula 1, R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -(L). a -HAr. According to one embodiment of this disclosure, R1 to R8 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-membered to 25-membered) heteroaryl, or -(L). a -HAr. According to another embodiment of this disclosure, R1 to R8 each independently represent hydrogen; deuterium; an unsubstituted (C6-C18) aryl group or a (C6-C18) aryl group substituted with at least one of deuterium, (C6-C18) aryl, and (5- to 25-membered) heteroaryl; an unsubstituted (5- to 25-membered) heteroaryl group or a (C6-C12) aryl group substituted with one or more (C6-C12) aryl groups; or -(L). a -HAr. For example, R1 to R8 can each independently be hydrogen, deuterium, unsubstituted phenyl, deuterated phenyl, phenyl substituted with hydroxyl, phenyl substituted with phenanthoxazolyl substituted with one or more phenyl groups, naphthyl, naphthyl substituted with one or more phenyl groups, naphthyl substituted with one or more dibenzofuranyl groups, hydroxyl, hydroxyl substituted with deuterium, triphenylene, phenanthrene, phenanthoxazolyl substituted with one or more phenyl groups, phenanthoxazolyl substituted with one or more naphthyl groups, phenanthiazoleyl substituted with one or more phenyl groups, carbazoleyl substituted with one or more phenyl groups, 23-membered nitrogen-containing heteroaryl, -(L) a -HAr etc.

[0031] In Equation 1, at least one of R1 to R8 is -(L). a -HAr, where a is 1 or 2.

[0032] In this document, L independently represents a single-bonded, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of this disclosure, L represents a single-bonded, substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5- to 20-membered) heteroarylene. According to another embodiment of this disclosure, L represents a single-bonded, substituted or unsubstituted (C6-C14) arylene, or a substituted or unsubstituted (5- to 17-membered) heteroarylene. For example, L can be a single-bonded, unsubstituted or substituted with one or more phenyl groups, a non-substituted or substituted with one or more phenyl groups, a biphenylene, a phenanthrene, an unsubstituted or substituted with one or more phenyl groups, a phenanthrene-oxazolyl, a carbazolyl, etc.

[0033] HAr represents a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group. According to one embodiment of this disclosure, HAr represents a substituted or unsubstituted nitrogen-containing (6- to 14-membered) heteroaryl group. According to another embodiment of this disclosure, HAr represents a substituted nitrogen-containing (6- to 14-membered) heteroaryl group. For example, HAr can be a substituted triazine, a substituted quinoxalinyl, a substituted quinazolinyl, a substituted 1,6-naphthidyl, a substituted benzoquinoxalinyl, a substituted benzoquinoxalinyl, etc.; wherein one or more substituents of the substituted triazine, substituted quinoxalinyl, substituted quinazolinyl, substituted 1,6-naphthidyl, substituted benzoquinoxalinyl, and substituted benzoquinoxalinyl can each independently be at least one, preferably any two, selected from the group consisting of: deuterium; unsubstituted or deuterium-, one or more phenanthrozo-, one or more phenyl-substituted phenanthrozo-, or one or more 23-membered nitrogen-containing heteroaryl groups substituted with phenyl groups. ; unsubstituted or deuterated biphenyl; unsubstituted or substituted naphthyl group; phenanthrene group; phenylphenanthrene group; terphenyl; triphenylene group; dibenzofuranyl group; unsubstituted or deuterated dibenzoselenyl group; unsubstituted or substituted phenyl group; phenanthroxazolyl group substituted with at least one of deuterium, unsubstituted or deuterated phenyl, and biphenyl; phenanthreneimidazolyl group substituted with one or more phenyl groups; phenanthrenethiazolyl group substituted with one or more phenyl groups; unsubstituted or substituted carbazole group; indolocarbazole group substituted with one or more phenyl groups; and 23-membered nitrogen-containing heteroaryl group.

[0034] According to one embodiment of this disclosure, Formula 1 can be represented by any one of Formulas 1-1 to 1-4 below.

[0035] ----- (1-1) ----- (1-2) ----- (1-3) ----- (1-4) In equations 1-1 to 1-4, R1 to R8, L, HAr and a are as defined in equation 1.

[0036] According to one embodiment of this disclosure, HAr of formula 1 can be represented by any one of the following formulas 1-5 to 1-7.

[0037] ----- (1-5) ----- (1-6) ----- (1-7) In equations 1-5 to 1-7, X1 to X8 each represent CR independently. 25 Or N; R 25 Ar7 and Ar8 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl, where R 25 It can be attached to adjacent substituents to form one or more rings; and This indicates the site that is linked to dibenzoselenene.

[0038] According to one embodiment of the present disclosure, in formulas 1-5, X1 to X3 all represent N. According to one embodiment of the present disclosure, in formulas 1-5, Ar7 and Ar8 each independently represent substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (5-membered to 25-membered) heteroaryl. For example, Ar7 and Ar8 can each independently be an unsubstituted or deuterated phenanthroxazolyl substituted with one or more hydroxyl groups, one or more phenyl groups, and one or more 23-membered nitrogen-containing heteroaryl groups; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated naphthyl substituted with one or more hydroxyl groups; phenanthryl; phenylphenanthryl; terphenyl; hydroxyl; triphenylene; dibenzofuranyl; an unsubstituted or deuterated carbazoyl substituted with one or more phenyl groups; an unsubstituted or deuterated dibenzoselenyl; a phenanthroxazolyl substituted with at least one of deuterium, an unsubstituted or deuterated phenyl, and a biphenyl; an indolocarbazoyl substituted with one or more phenyl groups; a 23-membered nitrogen-containing heteroaryl group; etc.

[0039] According to one embodiment of this disclosure, in formulas 1-6 and 1-7, any two of X1, X2, and X4 to X8 represent N, and the remaining represent CR. 25 According to one embodiment of this disclosure, in formulas 1-6 and 1-7, R 25This indicates a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group; or it may be attached to an adjacent substituent to form one or more rings. For example, R 25 It can be phenyl, biphenyl, unsubstituted or substituted with one or more phenyl groups, phenanthoxazolyl substituted with one or more phenyl groups, phenanthiazolyl substituted with one or more phenyl groups, or a 23-membered nitrogen-containing heteroaryl group; or it can be attached to an adjacent substituent to form a fused benzene, etc.

[0040] The compound represented by Formula 2 will be described in more detail below.

[0041] In Formula 2, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of this disclosure, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6-C12) arylene, or a substituted or unsubstituted (5- to 15-membered) heteroarylene. According to another embodiment of this disclosure, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6-C12) arylene, or an unsubstituted (5- to 15-membered) heteroarylene. For example, L1 to L3 may each independently be a single bond, a phenylene, a deuterated substituted phenylene, a biphenylene, a naphthylene, a dibenzofuranyl, a dibenzothiophene, etc.

[0042] In Formula 2, Ar1 to Ar3 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L b -N(Ar c (Ar) d According to one embodiment of this disclosure, Ar1 to Ar3 each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C10) cycloalkyl, or -L b -N(Arc (Ar) d According to another embodiment of this disclosure, Ar1 to Ar3 each independently represent an unsubstituted (C6-C30) aryl group or a (C6-C20) aryl group substituted with at least one of deuterium, (C1-C6) alkyl, and (C6-C20) aryl; an unsubstituted (C3-C10) cycloalkyl group or a (C3-C10) aryl group substituted with at least one of deuterium, (C3-C25) heteroaryl, and unsubstituted (C6-C15) aryl; or -L b -N(Ar c (Ar) d For example, Ar1 to Ar3 can each independently be an unsubstituted or deuterated phenyl, tert-butylphenyl, naphthyl, unsubstituted or deuterated biphenyl, terphenyl, hydroxyl, anthracene, phenanthryl, fluoranthyl, dimethylfluorenyl, diphenylfluorenyl, methylphenylfluorenyl, dimethylbenzofluorenyl, spirodifluorenyl, spirocyclopentanylfluorenyl, (C22) aryl; a phenanthreneoxazolyl substituted with at least one of deuterated, unsubstituted or deuterated phenyl, biphenyl, naphthyl and pyridyl; a phenanthrenethiazolyl substituted with one or more phenyl or one or more biphenyl; an unsubstituted or deuterated or deuterated dibenzofuranyl; benzene Naphthofuranyl, dibenzothiopheneyl, unsubstituted or substituted carbazoleyl, carbazoleyl fused to dimethyl-substituted cyclopentyl via linkage with one or more adjacent substituents, naphthooxazolyl substituted with one or more phenyl groups, phenoxazinyl, pyridyl substituted with one or more phenyl groups, benzothiopheneyl, benzimidazolyl substituted with one or more phenyl groups, dibenzocarbazoleyl, unsubstituted or substituted with one or more phenyl groups, 23-membered nitrogen-containing heteroaryl, unsubstituted or substituted with one or more phenyl groups, 26-membered nitrogen-containing heteroaryl, 27-membered nitrogen-containing heteroaryl, 30-membered nitrogen-containing heteroaryl, cyclohexyl, diphenylamino, etc.

[0043] In this article, L b This indicates a single-bonded, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. For example, L b It can be a single key.

[0044] Ar c and Ar d Each of these groups independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group. According to one embodiment of this disclosure, Ar c and Ard Each independently represents a substituted or unsubstituted (C6-C12) aryl group. According to another embodiment of this disclosure, Ar... c and Ar d Each independently represents an unsubstituted (C6-C12) aryl group. For example, Ar c and Ar d Each can be an phenyl group, etc., independently.

[0045] In Equation 2, the case where L1 to L3 are all single bonds and Ar1 to Ar3 are all hydrogens is excluded.

[0046] According to one embodiment of this disclosure, formula 2 can be represented by any one of formulas 2-1 to 2-14 below.

[0047] ----- (2-1) ----- (2-2) ----- (2-3) ----- (2-4) ----- (2-5) ----- (2-6) ----- (2-7) ----- (2-8) ----- (2-9) ----- (2-10) ----- (2-11) ----- (2-12) ----- (2-13) ----- (2-14) In equations 2-1 to 2-14, Y1, Y2, Z1, and Z2 each independently represent -N= and -NR. 21 -, -O-, or -S-, provided that either Y1 or Z1 is -N=, and the other Y1 or Z1 is -NR. 21 -, -O-, or -S-, provided that either Y2 or Z2 is represented by -N=, and the other Y2 or Z2 is represented by -NR. 21-、-O- or -S-; T represents CR 22 R 23 NR 24 , O or S; T1 to T 13 and W1 to W 12 Each can be represented independently as N or CV1; R 11 Ar6 and Ar6 independently represent substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; R 12 To R 19 R 21 To R 28 V1 and V1 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L c -N(Ar e (Ar) f Alternatively, it can be attached to adjacent substituents to form one or more substituted or unsubstituted rings; L c Indicates a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar e and Ar f Each of the following can independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl; b and i represent 1; c, d, j, m, and n each independently represent 1 or 2; e, f, g, f', k, l, and o each independently represent integers from 1 to 4; g' represents integers from 1 to 3; where if c to g, f', g', l, m, n, and o are integers of 2 or greater, then each R12 To each R 19 and each R 25 To each R 28 They can be the same as or different from each other; and Ar2, Ar3, and L1 to L3 are defined as in Equation 2.

[0048] According to one embodiment of this disclosure, Y1, Y2, Z1 and Z2 each independently represent -N=, -O- or -S-, provided that either Y1 or Z1 represents -N= and the other of Y1 or Z1 represents -O- or -S-, provided that either Y2 or Z2 represents -N= and the other of Y2 or Z2 represents -O-.

[0049] According to one embodiment of this disclosure, T represents CR 22 R 23 NR 24 、O or S.

[0050] According to an embodiment of this disclosure, T1 to T 13 and W1 to W 12 Each represents CV1 independently.

[0051] According to one embodiment of this disclosure, R 11 This indicates a substituted or unsubstituted (C6-C30) aryl group, or an unsubstituted (5- to 25-membered) heteroaryl group. For example, R 11 It can be unsubstituted or deuterated phenyl, naphthyl, biphenyl, pyridyl, etc.

[0052] According to one embodiment of this disclosure, Ar6 represents an unsubstituted (C6-C30) aryl group, such as a phenyl group.

[0053] According to one embodiment of this disclosure, R 12 To R 14 Each can independently represent hydrogen, deuterium, or an unsubstituted (C6-C30) aryl group; or they can be attached to adjacent substituents to form one or more rings. For example, R 12 To R 14 Each can be hydrogen, deuterium, or phenyl independently; or it can be attached to an adjacent substituent to form benzene, etc.

[0054] According to one embodiment of this disclosure, R 15 and R 16 Each can independently represent hydrogen or deuterium; or they can be attached to adjacent substituents to form one or more substituted or unsubstituted rings. For example, R 15 To R 16 They can be hydrogen or deuterium independently; or they can be attached to adjacent substituents to form fused, dimethyl-substituted cyclopentanes, benzenes, etc.

[0055] According to one embodiment of this disclosure, R 17 To R 19 Each can independently represent either hydrogen or an unsubstituted (C6-C30) aryl group. For example, R 17 To R 19 They can be hydrogen, phenyl, etc., independently.

[0056] According to one embodiment of this disclosure, R 22 and R 23 Each can independently represent an unsubstituted (C1-C30) alkyl or an unsubstituted (C6-C30) aryl; or they can be attached to adjacent substituents to form one or more substituted or unsubstituted rings. For example, R 22 and R 23 Each can be methyl or phenyl independently; or it can be attached to an adjacent substituent to form cyclopentane, fluorene, etc.

[0057] According to one embodiment of this disclosure, R 24 This indicates an unsubstituted (C6-C30) aryl group. For example, R 24 It can be phenyl.

[0058] According to one embodiment of this disclosure, R 25 To R 28 It represents hydrogen.

[0059] According to one embodiment of this disclosure, V1 represents hydrogen or an unsubstituted (C6-C30) aryl group; or it may be attached to an adjacent substituent to form one or more substituted or unsubstituted rings. For example, V1 may be hydrogen or a phenyl group; or it may be attached to an adjacent substituent to form one or more substituted or unsubstituted rings, which may be cyclopentane, fluorene, etc.

[0060] The compound represented by Formula 1 may be selected from at least one of the following compounds, but is not limited thereto.

[0061]

[0062] The compound represented by Formula 2 may be selected from at least one of the following compounds, but is not limited thereto.

[0063]

[0064] A combination of at least one of compounds H1-1 to H1-194 and at least one of compounds H2-1 to H2-159 can be used in organic electroluminescent devices.

[0065] In addition, this disclosure provides an organic electroluminescent compound represented by the following formula 1'.

[0066] ----- (1')

[0067] In Formula 1', R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- 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, fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -(L). a -HAr, provided that R1 to R8 are not 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl; At least one of R1 to R8 is -(L) a -HAr; HAr indicates a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group; L independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and 'a' represents 1 or 2; The prerequisite is that any one of R1 to R8 is -(L). a -HAr case; a is 1; L is a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene; and HAr is a triazine group, each independently selected from the group consisting of any two of the following: phenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, excluding pyridyl groups substituted with phenyl. The prerequisite is that any one of R1 to R8 is -(L). a In the case of -HAr; a is 1; L is a single bond or pyridylene; HAr is a triazine group substituted by any two of the following groups, each independently selected: an unsubstituted or deuterated or 9,9-dimethylfluorenyl substituted phenyl, an unsubstituted or deuterated biphenyl, a phenyl-substituted pyridyl, an unsubstituted or deuterated 9,9-dimethylfluorenyl, 9,9-dimethylazafluorenyl, spiro[cyclohexane-1,9'-fluorenyl]yl, and 9,9'-spirodifluorenyl; and any one or two of the remaining R1 to R8 are unsubstituted phenyl or exclude unsubstituted biphenyl; and The premise is that organic electroluminescent compounds with the following structures are excluded.

[0068] .

[0069] According to one embodiment of this disclosure, formula 1' can be represented by any one of formulas 1'-1 to 1'-4 below.

[0070] ----- (1'-1) ----- (1'-2) ----- (1'-3) ----- (1'-4) In equations 1'-1 to 1'-4, R1 to R8, L, HAr, and a are as defined in equation 1'.

[0071] According to one embodiment of this disclosure, HAr of formula 1' can be selected from formulas 1'-5 to 1'-7 below.

[0072] ----- (1'-5) ----- (1'-6) ----- (1'-7) In equations 1'-5 to 1'-7, X1 to X8 each represent CR independently. 25 Or N; R 25 Ar7 and Ar8 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl, where R 25 It can be attached to adjacent substituents to form one or more rings; and This indicates the site that is linked to dibenzoselenene.

[0073] The compound represented by Formula 1' may be selected from at least one of the following compounds, but is not limited thereto.

[0074]

[0075] Furthermore, this disclosure provides an organic electroluminescent device comprising an organic electroluminescent compound having Formula 1'. In this document, the organic electroluminescent compound having Formula 1' may be contained in a light-emitting layer, an electron transport layer, or an electron buffer layer, but is not limited thereto.

[0076] The compounds represented by formulas 1, 1', and 2 according to this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, compounds represented by formula 1 or 1' can be prepared with reference to the following reaction schemes, but are not limited thereto. Compounds represented by formula 2 can be prepared with reference to Korean Patent Application Publication No. 2020-0007644 (published January 22, 2020), Korean Patent Application Publication No. 2018-0099487 (published September 5, 2018), etc., but are not limited thereto.

[0077] [Reaction Scheme 1]

[0078] [Reaction Scheme 2]

[0079] In reaction schemes 1 and 2, R1 to R7, L, HAr, and a are as defined in equation 1 or 1', and This indicates the site that is linked to dibenzoselenene.

[0080] Although illustrative synthetic examples of compounds represented by Formula 1 or 1' have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even when substituents defined by Formula 1 or 1' but not specified in the specific synthetic examples are bonded.

[0081] The organic electroluminescent device disclosed herein includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer may comprise a plurality of organic electroluminescent materials, wherein the plurality of organic electroluminescent materials includes a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of the present disclosure, the organic electroluminescent device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer may comprise a compound represented by Formula 1 and a compound represented by Formula 2.

[0082] The light-emitting layer includes one or more hosts and dopants, wherein the one or more hosts comprise multiple host materials, a compound represented by Formula 1 may be included as a first host compound of the multiple host materials, and a compound represented by Formula 2 may be included as a second host compound of the multiple host materials. In this document, the weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0083] In this disclosure, the light-emitting layer is a light-emitting layer, which may be a single layer or multiple layers in which two or more layers are stacked. Among the various host materials of this disclosure, the first and second host materials may be contained in a single layer or in their respective distinct light-emitting layers. According to one embodiment of this disclosure, the doping concentration of the dopant compound relative to the host compound of the light-emitting layer may be less than 20 wt%.

[0084] The organic electroluminescent device according to this disclosure may include 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 injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of this disclosure, in addition to the various host materials according to this disclosure, the organic electroluminescent device according to this disclosure may further include an amine-based compound as at least one of a hole injection material, a hole transport material, a hole assist material, a light-emitting material, a light-emitting assist material, and an electron blocking material. Furthermore, according to one embodiment of this disclosure, in addition to the various host materials according to this disclosure, the organic electroluminescent device according to this disclosure may further include an azazine-based compound as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0085] The various host materials disclosed herein can be used as luminescent materials for white organic light-emitting devices. Various structures for white organic light-emitting devices have been proposed, such as side-by-side or stacked structures, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) luminescent components, or color conversion material (CCM) methods, etc. Furthermore, the various host materials disclosed herein can also be used in organic electroluminescent devices incorporating quantum dots (QDs).

[0086] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the emissive layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein two compounds can be used simultaneously in each of the multilayers. Furthermore, the hole injection layer can be doped with a p-type dopant. An electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the emissive layer, and can block electron leakage from the emissive layer and confine excitons within the emissive layer to prevent light leakage. The hole transport layer or electron blocking layer can be multilayered, wherein multiple compounds can be used in each of the multilayers.

[0087] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein two compounds can be used simultaneously in each of the multilayers. The hole blocking layer or electron transport layer can also be multilayered, wherein multiple compounds can be used in each of the multilayers. Furthermore, the electron injection layer can be doped with an n-type dopant.

[0088] The dopant included in the organic electroluminescent device of this disclosure may be at least one phosphorescent dopant or fluorescent dopant, and preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device according to this disclosure is not particularly limited, but may be selected from metallized complexes of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably from ortho-metallized complexes of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably from ortho-metallized iridium complexes.

[0089] The dopant included in the organic electroluminescent device of this disclosure may be a compound represented by formula 101, but is not limited thereto.

[0090] ------ (101)

[0091] In Equation 101, L is selected from any one of the following structures 1 to 3: [Structure 1] [Structure 2] [Structure 3]

[0092] R 100 To R 103Each of these can independently represent hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, 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 can be attached to an adjacent substituent to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, isoquinoline, benzofuranopyridine, benzothienopyridine, indoxpyridine, benzofuranoquinoline, benzothienoquinoline, or indoxpyridine; R 104 To R 107 Each of these can independently represent hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, 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 can be attached to an adjacent substituent to form one or more rings with benzene, such as substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenepyridine, benzofuran-pyridine, or benzothiophene-pyridine; R 201 To R 220 Each of these elements independently represents hydrogen, deuterium, halogen, unsubstituted or deuterated and / or one or more halogenated (C1-C30) alkyl, 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 rings; and s represents an integer from 1 to 3.

[0093] Specific examples of dopant compounds are shown below, but are not limited to.

[0094]

[0095] Each layer of the organic electroluminescent device disclosed herein can be formed by any of the following methods: dry film formation methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc.

[0096] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer is soluble or dispersible and in which there are no problems with film-forming ability.

[0097] Furthermore, the first and second host compounds according to this disclosure can be deposited into films by the methods listed above, typically via co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and an electric current is simultaneously applied to two chambers to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and an electric current is applied to a cell to evaporate the materials. Moreover, when the first and second host compounds are present in the same or different layers of an organic electroluminescent device, the two host compounds can be formed into films individually. For example, the second host compound can be evaporated after the first host compound is evaporated.

[0098] This disclosure allows for the provision of display systems using a variety of host materials, including compounds represented by Formula 1 and compounds represented by Formula 2. In other words, display systems or lighting systems can be manufactured using the various host materials of this disclosure. Specifically, display systems, such as those for organic light-emitting devices, smartphones, tablets, laptops, PCs, TVs, or automobiles, or lighting systems, such as outdoor or indoor lighting systems, can be manufactured using the various host materials of this disclosure.

[0099] In the following sections, the preparation methods and properties of the compounds of this disclosure will be explained in detail with reference to representative compounds of this disclosure, as well as the properties of organic electroluminescent devices comprising various host materials according to this disclosure. However, the following examples only illustrate the properties of organic electroluminescent devices comprising compounds or various host materials according to this disclosure, and this disclosure is not limited to the following examples.

[0100] Example 1: Preparation of compound H1-176

[0101] Synthesis of Compound 1-1

[0102] 2-Chloro-2'-iodo-1,1'-biphenyl (20 g, 63.5 mmol), 3-chloroperoxybenzoic acid (21.3 g, 95.3 mmol), 16 mL of trifluoromethanesulfonic acid, and 320 mL of dichloromethane were added to a reaction vessel and reacted for 1 hour. After the reaction was complete, the organic solvent was removed by evaporation. The residue was washed with ethyl acetate to obtain compound 1-1 (25 g).

[0103] Synthesis of Compounds 1-2

[0104] Compound 1-1 (19.7 g), potassium tert-butoxide (20.6 g, 184 mmol), selenium (10.9 g, 138 mmol), and 460 mL of dimethyl sulfoxide were added to a reaction vessel, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound 1-2 (8.6 g, yield: 71%).

[0105] Synthesis of compounds 1-3

[0106] Compounds 1-2 (4.1 g, 15.4 mmol), bis(pinacol)diboron (4.7 g, 18.5 mmol), tris(dibenzylacetone)dipalladium(0) (0.71 g, 0.77 mmol), tricyclohexylphosphine tetrafluoroborate (0.56 g, 1.54 mmol), potassium acetate (4.5 g, 46.2 mmol), and 80 mL of o-xylene were added to a reaction vessel, and the mixture was stirred under reflux for 2 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compounds 1-3 (5 g, yield: 92%).

[0107] Synthesis of compound H1-176

[0108] Compounds 1-3 (4.5 g, 12.6 mmol), 2-[1,1'-biphenyl]-3-yl-4-[1,1'-biphenyl]-4-yl-6-chloro-1,3,5-triazine (5.3 g, 12.7 mmol), tetrakis(triphenylphosphine)palladium(0) (0.73 g, 0.63 mmol), potassium carbonate (4.3 g, 31.5 mmol), 65 mL of toluene, 17 mL of ethanol, and 17 mL of distilled water were added to a reaction vessel, and the mixture was stirred under reflux for 3 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound H1-176 (7.3 g, yield: 94%).

[0109]

[0110] Example 2: Preparation of compound H1-177

[0111] Synthesis of Compound 2-1

[0112] 2-Iodo-1,1'-biphenyl (41.6 g, 148 mmol), 3-chloroperoxybenzoic acid (50 g, 223 mmol), 40 mL of trifluoromethanesulfonic acid, and 750 mL of dichloromethane were added to a reaction vessel and reacted for 1 hour. After the reaction was complete, the organic solvent was removed by evaporation. The residue was washed with ethyl acetate to obtain compound 2-1 (64 g).

[0113] Synthesis of compound 2-2

[0114] Compound 2-1 (64 g), potassium tert-butoxide (67.3 g, 600 mmol), selenium (35.5 g, 450 mmol), and 1500 mL of dimethyl sulfoxide were added to a reaction vessel, and the mixture was stirred at 80°C for 2 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound 2-2 (22.8 g, yield: 65%).

[0115] Synthesis of Compounds 2-3

[0116] Compound 2-2 (22.8 g, 98.6 mmol) and 500 mL of tetrahydrofuran were added to a reaction vessel under a nitrogen atmosphere and cooled to -78°C. Then, n-butyllithium (41 mL, 103 mmol) was slowly added dropwise. Next, trimethyl borate (12.6 mL, 113 mmol) was added dropwise, and the reaction was continued at room temperature for 12 hours. After the reaction was complete, the reaction was stopped with water, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound 2-3 (10 g, yield: 40%).

[0117] Synthesis of compound H1-177

[0118] Compound 2-3 (4 g, 14.5 mmol), 2-[1,1'-biphenyl]-3-yl-4-[1,1'-biphenyl]-4-yl-6-chloro-1,3,5-triazine (6.1 g, 14.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.84 g, 0.72 mmol), potassium carbonate (5 g, 36.2 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of distilled water were added to a reaction vessel, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound H1-177 (3.5 g, yield: 41%).

[0119]

[0120] Example 3: Preparation of compound H1-161

[0121] Synthesis of compound 3-3

[0122] Compound 3-2 (4.0 g, 9.5 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (2.1 g, 9.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.5 mmol), Cs₂CO₃ (6.2 g, 19 mmol), and 30 mL of toluene were added to a reaction vessel, and the mixture was stirred under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred at room temperature, and then methanol was added. The resulting solid was filtered under reduced pressure and separated by column chromatography using dichloromethane to obtain compound 3-3 (3.7 g, yield: 80%).

[0123] Synthesis of compound H1-161

[0124] Compound 3-3 (7 g, 14.5 mmol), compound 2-3 (4 g, 14.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.84 g, 0.72 mmol), potassium carbonate (5 g, 36.2 mmol), 80 mL of toluene, 20 mL of ethanol, and 20 mL of distilled water were added to a reaction vessel, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the precipitated solid was washed with distilled water and methanol. Compound H1-161 (8.4 g, yield: 85%) was purified by column chromatography.

[0125]

[0126] Example 4: Preparation of compound H1-78

[0127] Compound 2-3 (5 g, 18.1 mmol), 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine (6.2 g, 18.1 mmol), tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.909 mmol), potassium carbonate (6.2 g, 45.4 mmol), 90 mL of toluene, 23 mL of ethanol, and 23 mL of distilled water were added to a reaction vessel, and the mixture was stirred under reflux for 5 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound H1-78 (8 g, yield: 83%).

[0128]

[0129] Example 5: Preparation of compound H1-190

[0130] Synthesis of compound D1-1

[0131] Compound 2-2 (8.5 g, 36.77 mmol), 85 mL of benzene-D6, and trifluoromethanesulfonic acid (8.5 mL, 96.28 mmol) were added to a reaction vessel and stirred at 45°C for 3 hours. After cooling to room temperature, 8.5 mL of D2O was added and stirred for 10 minutes. After neutralization with aqueous K3PO4, the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound D1-1 (8.2 g, yield: 93%).

[0132] Synthesis of compound D1-2

[0133] Compound D-1 (7.2 g, 30.1 mmol) and 150 mL of tetrahydrofuran were added to a reaction vessel under a nitrogen atmosphere and cooled to -78°C. Then, n-butyllithium (14 mL, 36.1 mmol) was slowly added dropwise. Next, trimethyl borate (8.1 mL, 72.2 mmol) was added dropwise, and the reaction was continued at room temperature for 12 hours. After the reaction was complete, the reaction was stopped with water, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound D1-2 (1.7 g, yield: 20%).

[0134] Synthesis of compound H1-190

[0135] Compound D1-2 (1.7 g, 6.03 mmol), 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-triazine (2.1 g, 6.33 mmol), tetrakis(triphenylphosphine)palladium(0) (0.35 g, 0.30 mmol), potassium carbonate (2.1 g, 15.1 mmol), 30 mL of toluene, 8 mL of ethanol, and 8 mL of distilled water were added to a reaction vessel, and the mixture was stirred under reflux for 4 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. After removing the remaining water from the organic layer with magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound H1-190 (2.1 g, yield: 65%).

[0136]

[0137] Example 6: Preparation of compound H2-45

[0138] Synthesis of Compound 6-1

[0139] In a reaction vessel, [1,1'-biphenyl]-4-amine (60 g, 354 mmol), 2-bromodibenzo[b,d]furan (58.5 g, 236 mmol), Pd(OAc)2 (0.54 g, 3.23 mmol), P(Cy)3 (1.35 g, 3 mmol), and NaOtBu (40.9 g, 425.5 mmol) were dissolved in 600 mL of toluene and stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature. The solid was produced by using a diatomaceous earth filter and separated by column chromatography to obtain compound 6-1 (65.7 g, yield: 83%).

[0140] Synthesis of compound H2-45

[0141] In a reaction vessel, compound 6-1 (20 g, 59.6 mmol), compound CPPO (19.7 g, 59.7 mmol), Pd2(dba)3 (0.55 g, 0.6 mmol), X-Phos (0.57 g, 1.2 mmol), and NaOt-Bu (11.5 g, 119.6 mmol) were dissolved in 200 mL of o-xylene and stirred under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature. The solid was produced by using a diatomaceous earth filter and separated by column chromatography to obtain compound H2-45 (12.7 g, yield: 34%).

[0142]

[0143] Example 7: Preparation of compound H2-145

[0144] In a reaction vessel, 60 mL of toluene was added to compound 7-1 (5.0 g, 11.2 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (3.0 g, 12.3 mmol), Pd2(dba)3 (0.5 g, 0.56 mmol), s-phos (0.46 g, 1.12 mmol), and NaOtBu (2.7 g, 28 mmol), and stirred under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred at room temperature, and then MeOH was added. The resulting solid was filtered under reduced pressure and separated by column chromatography using dichloromethane / hexane to obtain compound H2-145 (2.3 g, 34%).

[0145]

[0146] Example 8: Preparation of compound H2-157

[0147] In a reaction vessel, compound 9-3 (5.0 g, 19.0 mmol), di([1,1'-biphenyl]-4-yl)amine (6.1 g, 19.0 mmol), Pd2(dba)3 (0.9 g, 0.95 mmol), P(t-bu)3 (1.0 mL, 1.90 mmol), and NaOtBu (2.7 g, 28.5 mmol) were dissolved in 95 mL of toluene and stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with ethyl acetate / H2O and separated by column chromatography to obtain compound H2-157 (8.4 g, yield: 81%).

[0148]

[0149] The luminous efficiency and lifetime characteristics of the OLED according to this disclosure will be explained below. However, the following examples are merely illustrative of the characteristics of the OLED according to this disclosure for a detailed understanding, and this disclosure is not limited to the following examples.

[0150] Device Examples 1 to 5: Production of red-emitting materials with various host materials according to this disclosure as the host. OLED

[0151] The OLED is produced according to this disclosure. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for the OLED is sequentially ultrasonically washed with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 from Table 5 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 from Table 5 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-1 to form a first hole injection layer with a thickness of 10 nm. Subsequently, compound HT-1 is deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying current to the chamber, 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, an emitting layer was deposited thereon as follows: the first host compound and the second host compound shown in Tables 1 to 3 below were introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into another chamber. The two host materials were evaporated at a rate of 1:1, and the dopant materials were evaporated simultaneously at different ratios, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form an emitting layer with a thickness of 40 nm on the second hole transport layer. Compounds ETL-1 and EIL-1 were evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer with a thickness of 35 nm on the emitting layer. After depositing compound EIL-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum phase deposition apparatus. This produced an OLED. Each compound used for each material was subjected to a 10-step process before use. -6 Purification is achieved through vacuum sublimation.

[0152] Device Examples 6 and 7: Production of red-emitting deposits with a single host material according to this disclosure as the host. OLED

[0153] The OLEDs are produced in the same manner as in Device Examples 1 to 5, except that only the first host compound shown in Table 4 below is used as the host of the light-emitting layer.

[0154] Comparative Example 1: Production of OLEDs emitting red light with a contrasting compound as the sole host material

[0155] The OLEDs were produced in the same manner as in Device Examples 1 to 5, except that only the comparative compound T-1 shown in Table 4 below was used as the host of the emitting layer.

[0156] Comparative Examples 2 to 4: Production of OLEDs emitting red light with the comparative compound as the first host compound deposited.

[0157] The OLEDs are produced in the same manner as in Device Examples 1 to 5, except that the first host compound (comparative compound) and the second host compound shown in Tables 1 to 3 below are used as the host of the light-emitting layer.

[0158] Tables 1 to 4 below provide the driving voltage, luminous efficiency, and emission color of the OLEDs produced in Device Examples 1 to 7 and Comparative Examples 1 to 4 at a brightness of 1,000 nits, as well as the time taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits (lifetime: T95).

[0159] [Table 1]

[0160] [Table 2]

[0161] [Table 3]

[0162] [Table 4]

[0163] As can be confirmed from Tables 1 to 3 above, compared with organic electroluminescent devices deposited with multiple host materials including a first host material and a second host material, the organic electroluminescent device deposited according to the present disclosure exhibits significantly improved lifetime characteristics while exhibiting the same level of driving voltage and luminous efficiency, compared with organic electroluminescent devices deposited with a comparative compound as a single host material. Furthermore, as can be confirmed from Table 4 above, compared with organic electroluminescent devices deposited with a comparative compound as a single host material, the organic electroluminescent device deposited with the first host material according to the present disclosure as a single host material exhibits significantly improved lifetime characteristics while exhibiting the same level of driving voltage and luminous efficiency.

[0164] The compounds used in the apparatus examples and comparative examples are shown in Table 5 below.

[0165] [Table 5]

Claims

1. An organic electroluminescent compound, represented by the following formula 1': ----- (1') In equation 1', R1 to R8 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- 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) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -(L). a -HAr, provided that R1 to R8 are not 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl; At least one of R1 to R8 is -(L) a -HAr; HAr indicates a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group; L independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; and 'a' represents 1 or 2; The prerequisite is that any one of R1 to R8 is -(L). a -HAr case; a is 1; L is a substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene; and HAr is a triazine group that is independently selected from any two of the following groups: phenyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, excluding pyridyl groups substituted with phenyl. The prerequisite is that any one of R1 to R8 is -(L). a In the case of -HAr; a is 1; L is a single bond or pyridylene; HAr is a triazine group substituted by any two of the following groups, each independently selected: an unsubstituted or deuterated or 9,9-dimethylfluorenyl substituted phenyl, an unsubstituted or deuterated biphenyl, a phenyl-substituted pyridyl, an unsubstituted or deuterated 9,9-dimethylfluorenyl, 9,9-dimethylazafluorenyl, spiro[cyclohexane-1,9'-fluorenyl]yl, and 9,9'-spirodifluorenyl; and any one or two of the remaining R1 to R8 are unsubstituted phenyl or exclude unsubstituted biphenyl; and The premise is that organic electroluminescent compounds with the following structures are excluded: 。 2. The organic electroluminescent compound according to claim 1, wherein, Equation 1' is represented by any one of the following equations: 1'-1 to 1'-4 ----- (1'-1) ----- (1'-2) ----- (1'-3) ----- (1'-4) In equations 1'-1 to 1'-4, R1 to R8, L, HAr and a are as defined in claim 1.

3. The organic electroluminescent compound according to claim 1, wherein, In Equation 1', HAr is selected from the following structures: ----- (1'-5) ----- (1'-6) ----- (1'-7) In equations 1'-5 to 1'-7, X1 to X8 each represent CR independently. 25 Or N; R 25 Ar7 and Ar8 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl, where R 25 It can be attached to adjacent substituents to form one or more rings; and This indicates the site where it is linked to dibenzoselenene.

4. The organic electroluminescent compound according to claim 1, wherein, The compound represented by formula 1' is selected from the following compounds: and .

5. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

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