Organic electroluminescent compounds, various host materials, and organic electroluminescent devices containing them.

Abstract

This disclosure relates to: an organic electroluminescent compound represented by Formula 2-1; multiple host materials, said multiple host materials comprising a first host material and a second host material, the first host material comprising a compound represented by Formula 1, and the second host material comprising a compound represented by Formula 2; and an organic electroluminescent device comprising said multiple host materials. By comprising an organic electroluminescent compound according to this disclosure as a single host material, or comprising a specific combination of compounds according to this disclosure as multiple host materials, an organic electroluminescent device with lower driving voltage, higher luminous efficiency, and / or improved lifetime characteristics compared to conventional organic electroluminescent devices can be provided.

Description

Technical Field

[0001] This disclosure relates to an organic electroluminescent compound, various host materials, and an organic electroluminescent device comprising the same. Background Technology

[0002] Small-molecule green organic light-emitting diodes (OLEDs) were first developed in 1987 by Tang et al. at Eastman Kodak using a TPD / ALq3 bilayer consisting of a light-emitting layer and a charge-transport layer. Since then, OLED development has been rapidly influenced, and OLEDs have been commercialized. Currently, OLEDs primarily use phosphorescent materials with excellent luminous efficiency in panel implementation. However, in many applications such as TVs and lighting equipment, the lifetime of OLEDs is insufficient, and higher efficiency OLEDs are still needed. Typically, the higher the brightness of an OLED, the shorter its lifetime. Therefore, for long-term use and high resolution of displays, OLEDs with high luminous efficiency and / or long lifetime characteristics are required.

[0003] Various materials or concepts for organic layers in OLEDs have been proposed to enhance luminous efficiency, driving voltage, and / or lifetime. However, they have not been satisfactory in practical applications.

[0004] Korean Patent Application Publication No. 10-2017-0022865 discloses an OLED using phenanthrenexaazole and phenanthrenethiazole compounds as the main components. However, the aforementioned reference does not specifically disclose any particular combination of the various main materials disclosed herein. Furthermore, there is still a need to develop main materials for improving OLED performance. Summary of the Invention

[0005] Technical issues

[0006] The purpose of this disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application in organic electroluminescent devices. Another purpose of this 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. A further purpose of this disclosure is to provide an organic electroluminescent device that, by comprising a compound according to this disclosure as a single host material, or comprising a specific combination of compounds according to this disclosure as multiple host materials, exhibits lower driving voltage, higher luminous efficiency, and / or improved lifetime characteristics.

[0007] Solution to the problem

[0008] As a result of in-depth research into solving the technical problem, the inventors of this invention have discovered that the above-mentioned objective can be achieved by an organic electroluminescent compound represented by the following formula 2-1:

[0009]

[0010] in

[0011] X a Indicates O or S;

[0012] Ar a and Ar b Each can independently represent a substituted or unsubstituted (C6-C18) aryl group, provided that Ar... a and Ar b At least one of them represents a substituted or unsubstituted naphthyl group; and

[0013] R1 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or combinations thereof.

[0014] Furthermore, the inventors of this invention have noted that compounds having nuclei such as phenanthroxazole or phenanthrethiazole exhibit exceptionally low levels of least unoccupied molecular orbital (LUMO) energies compared to typical hole-type hosts, and have investigated hole-type hosts capable of forming suitable band gaps with the aforementioned compounds. Therefore, the inventors of this invention have discovered that when a combination of compounds represented by Formula 1 and Formula 2 is used in the luminescent layer, the hole and electron properties are balanced by appropriate HOMO and LUMO energy levels, thereby providing an organic electroluminescent device with lower driving voltage, higher luminous efficiency, and / or longer lifetime characteristics compared to conventional organic electroluminescent devices.

[0015] Specifically, the inventors of this invention have discovered that the above objectives 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.

[0016]

[0017] In Equation 1,

[0018] X1 and Y1 can each independently represent -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 represents -N= and the other of X1 and Y1 represents -NR5-, -O-, or -S-;

[0019] L1 represents a single bond, or a substituted or unsubstituted (C6-C30) aryl group;

[0020] R 31 and R 32 Each can be used independently to represent a substituted or unsubstituted (3 to 30) heteroaryl group;

[0021] R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0022] R2 to R5 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 fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N(Ar1)(Ar2); or may be attached to adjacent substituents to form one or more rings;

[0023] L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0024] Ar1 and Ar2 each independently represent 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; and

[0025] a and b each independently represent an integer of 1 or 2, and c represents an integer from 1 to 3, wherein if a to c are integers of 2 or greater, then each R2, each R3, and each R4 may be the same or different.

[0026] HAr-((L2) e -Ar2) d -----(2)

[0027] In Equation 2,

[0028] HAr indicates a substituted or unsubstituted (3- to 20-membered) heteroaryl group containing one or more nitrogen atoms;

[0029] L2 independently represents substituted or unsubstituted (C6-C30) aryl groups;

[0030] Ar2 independently represents substituted or unsubstituted (C6-C30) aryl groups, or formulas 3 or 4 below:

[0031]

[0032] Y represents O, S, N-*, or NR. 21 ;

[0033] R 21 Indicates substituted or unsubstituted (C6-C30) aryl groups;

[0034] R 11 To R 18 Each can independently represent a site linked to L2; or 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 fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L4-N(Ar3)(Ar4); or may be attached to adjacent substituents to form one or more rings;

[0035] X 31 To X 42 Each can be represented independently as N or CR. a ;

[0036] R a Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30) 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 fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L5-N(Ar5)(Ar6); or may be attached to adjacent substituents to form one or more rings;

[0037] L4 and L5 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0038] Ar3 to Ar6 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, 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;

[0039] d represents an integer from 1 to 3, where if d is an integer of 2 or greater, then each ((L2)) e -Ar2) can be the same or different;

[0040] e represents an integer from 0 to 2, where if e is an integer of 2, then each L2 can be the same or different; and

[0041] * indicates a site connected to L2.

[0042] Beneficial effects of the present invention

[0043] The organic electroluminescent compounds according to this disclosure exhibit performance suitable for use in organic electroluminescent devices. Furthermore, by comprising a compound according to this disclosure as a single host material, or comprising a specific combination of compounds according to this disclosure as multiple host materials, organic electroluminescent devices with lower driving voltages, higher luminous efficiency, and / or improved lifetime characteristics compared to conventional organic electroluminescent devices can be provided, and these organic electroluminescent devices can be used to manufacture display devices or lighting devices. Detailed Implementation

[0044] The present disclosure will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the disclosure in any way.

[0045] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and can be included, as needed, in any layer constituting the organic electroluminescent device.

[0046] 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.

[0047] The term "multiple organic electroluminescent materials" in this disclosure refers to an organic electroluminescent material comprising a combination of at least two compounds, said material being contained in any layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, the multiple organic electroluminescent materials of this disclosure can be a combination of at least two compounds, said material being contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be contained in the same or different layers by methods used in the art. For example, they can be co-evaporated or mixed, or the at least two compounds can be evaporated individually.

[0048] The term "multiple host materials" in this disclosure refers to a host material comprising a combination of at least two compounds, said host material being contained in any light-emitting layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, the multiple host materials of this disclosure can be a combination of at least two host materials, and optionally may further include conventional materials contained in organic electroluminescent materials. The multiple host materials of this disclosure can be contained in any light-emitting layer constituting an organic electroluminescent device. Using methods used in the art, the at least two compounds contained in the multiple host materials of this disclosure can be contained together in one light-emitting layer, or can be contained separately in different light-emitting layers. For example, they can be co-evaporated or mixed, or the at least two compounds can be evaporated individually.

[0049] 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 20, and more preferably 1 to 10. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc. The term "(C2-C30)alkenyl" refers to a straight-chain or branched alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term "(C2-C30) ynyl" refers to a straight-chain or branched ynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned ynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpentan-2-ynyl, 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, preferably 5 to 7, cyclic skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of O, S, and N. The aforementioned heterocyclic alkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)(aryl) group" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 cyclic skeleton carbon atoms, wherein the number of cyclic skeleton carbon atoms is preferably 6 to 20. The aforementioned (aryl) group may be partially saturated and may contain a spirostructure. The aforementioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indene, triphenylene, pyrene, tetracenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, etc. More specifically, the above-mentioned aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzanthyl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, tetraphenyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Benzophenanthryl, 2-Benzophenanthryl, 3-Benzophenanthryl, 4-Benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzo[a]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl Phenyl-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, benzofluoranthyl, 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-4-benzene [a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl 11,11-Dimethyl-3-benzo[c]fluorenyl, 11,11-Dimethyl-4-benzo[c]fluorenyl, 11,11-Dimethyl-5-benzo[c]fluorenyl, 11,11-Dimethyl-6-benzo[c]fluorenyl, 11,11-Dimethyl-7-benzo[c]fluorenyl, 11,11-Dimethyl-8-benzo[c]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 ]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11 ,11-Diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-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.

[0050] The term "(3- to 30-membered) (hypo)aryl" refers to an aryl group having 3 to 30 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. 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, furazanyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as fused-ring heteroaryl groups, such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, and dibenzofuranyl. Thiophene, benzonaphthiofuran, benzofuranylthienyl, diazabenzofuran, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, benzoisoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthidyl, triazanaphthyl thyl), benzothiophenepyrimidinyl, carbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenthiazinyl, phenanthidyl, benzodioxanepentenyl, dihydroacridinyl, pyridinylpyrazinyl, benzofuranopyridinyl, benzofuranopyrimidinyl, dibenzoselenophenyl, benzofuranoquinolinyl, benzofuranoquinazolinyl, benzofuranonaphridinyl, naphthofuranopyrimidinyl, benzothiophenepyrimidinyl, benzothiophenepyrimidinyl, benzothiophenepyrimidinyl, benzothiophenepyrimidinyl, benzothiophenepyrimidinyl, benzothiophenepyrimidinyl Thiophene-naphthidyl, benzothiophene-pyrimidyl, naphthiophene-pyrimidyl, pyrimidindolyl, benzopyrimidindolyl, benzofuran-pyrazinyl, naphthiophene-pyrazinyl, benzothiophene-pyrazinyl, naphthiophene-pyrazinyl, pyrazinindolyl, benzopyrazinindolyl, benzotriazofenzinyl, imidazopyridyl, benzopyran-quinazolinyl, thiobenzopyran-quinazolinyl, dimethylbenzovinidyl, indolocarbazoyl, indenecarbazoyl, etc. More specifically, the aforementioned heteroaryl groups may include 1-pyrrole, 2-pyrrole, 3-pyrrole, 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-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl,6-Imidazolopyridyl, 7-Imidazolopyridyl, 8-Imidazolopyridyl, 3-pyridyl, 4-pyridyl, 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-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 1-carbazoleyl, 2-carbazoleyl, 3 -Carbazole, 4-Carbazole, 9-Carbazole, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-Phenyridyl, 2-Phenyridyl, 3-Phenyridyl 4-Phenyridyl, 6-Phenyridyl, 7-Phenyridyl, 8-Phenyridyl, 9-Phenyridyl, 10-Phenyridyl, 1-Acridineyl, 2-Acridineyl, 3-Acridineyl, 4-Acridineyl, 9-Acridineyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thienyl, 3-Thienyl, 2-Methylpyridinium 1-ylpyrrolo-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, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl6-Naphtho-[1,2-b]-benzofuranyl, 7-Naphtho-[1,2-b]-benzofuranyl, 8-Naphtho-[1,2-b]-benzofuranyl, 9-Naphtho-[1,2-b]-benzofuranyl, 10-Naphtho-[1,2-b]-benzofuranyl, 1-Naphtho-[2,3-b]-benzofuranyl, 2-Naphtho-[2, 3-[b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl 9-Naphtho-[2,3-b]-benzofuranyl, 10-Naphtho-[2,3-b]-benzofuranyl, 1-Naphtho-[2,1-b]-benzofuranyl, 2-Naphtho-[2,1-b]-benzofuranyl, 3-Naphtho-[2,1-b]-benzofuranyl, 4-Naphtho-[2,1-b]-benzofuranyl, 5-Naphtho-[2, 1-b]-benzofuranyl, 6-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, 8-Naphtho-[1,2-b]-benzothiophene 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]-benzothiophene, 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-[2,3-b]-benzothiophene 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]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl,7-Benzofurano[3,2-d]pyrimidinyl, 8-Benzofurano[3,2-d]pyrimidinyl, 9-Benzofurano[3,2-d]pyrimidinyl, 2-Benzofurano[3,2-d]pyrimidinyl, 6-Benzofurano[3,2-d]pyrimidinyl, 7-Benzofurano[3,2-d]pyrimidinyl, 8-Benzofurano[3,2-d]pyrimidinyl, 9-Benzofurano[3,2-d]pyrimidinyl, 2-Benzofurano[3,2-d]pyrazinyl, 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl, 9-Benzofurano[3,2-d]pyrazinyl Furano[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-siliconfluorenyl, 2-siliconfluorenyl, 3-siliconfluorenyl, 4-siliconfluorenyl, 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 addition, "halogens" include F, Cl, Br, and I.

[0051] The term "fused-ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings" refers to a fused ring functional group having at least one aliphatic ring having 3 to 30, preferably 3 to 25, and more preferably 3 to 18 ring skeletal carbon atoms, and at least one aromatic ring having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring skeletal carbon atoms. The aforementioned fused-ring group may include a fused-ring group of at least one benzene and at least one cyclohexane, a fused-ring group of at least one naphthalene and at least one cyclopentane, etc. The carbon atoms of the fused-ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings may be replaced by at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of N, O, and S.

[0052] In this document, "substituted" in the phrase "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 a 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" can be pyridine-triazine. That is, pyridine-triazine can be interpreted as a heteroaryl substituent, or a substituent in which two heteroaryl substituents are linked.The substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted heteroaryl containing one or more nitrogen atoms, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and one or more substituents of the substituted fused ring groups of one or more aliphatic rings and one or more aromatic rings in this disclosure are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1) -C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)ynyl; (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 (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl groups; unsubstituted or (C6-C30)aryl substituted with at least one of one or more (C1-C30)alkyl and one or more (3- to 30-membered)heteroaryl groups; tri(C1-C30)alkylsilyl; tri (C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a fused ring group of 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; (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) (C1-C30)alkyl(C6-C30)arylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C6-C30)aryl(C6-C30)arylamino; (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, one or more substituents are each independently at least one selected from the group consisting of: (C1-C10)alkyl; (C6-C20)aryl; unsubstituted or (3- to 20-membered) heteroaryl substituted with one or more (C6-C20)aryl groups; and di(C6-C20)arylamino. According to another embodiment of the present disclosure, one or more substituents are each independently at least one selected from the group consisting of: (C1-C6)alkyl; (C6-C12)aryl; unsubstituted or (5- to 15-membered) heteroaryl substituted with one or more (C6-C12)aryl groups; and di(C6-C12)arylamino. For example, one or more substituents may each independently be at least one selected from the group consisting of: methyl, phenyl, naphthyl, pyridyl, carbazole, phenylquinoxalinyl, and diphenylamino.

[0053] In the formulas of this disclosure, the ring formed by the connection of adjacent substituents can be a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic ring, or a combination thereof. Furthermore, the formed ring 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 this disclosure, the number of ring skeleton atoms is 5 to 20. According to another embodiment of this disclosure, the number of ring skeleton atoms is 5 to 15. For example, the fused ring can be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0054] In the formulas disclosed herein, the heteroaryl, heteroaryl, and heterocycloalkyl groups may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be bonded to at least one of the following groups: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-membered 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)alkylbis(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.

[0055] The compounds represented by formulas 1 and 2 will be described in more detail below.

[0056] In Equation 1, X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that one of X1 and Y1 represents -N= and the other of X1 and Y1 represents -NR5-, -O-, or -S-. According to one embodiment of this disclosure, one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -O- or -S-. For example, X1 can be -N=, and Y1 can be -O- or -S-.

[0057] In Formula 1, L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of this disclosure, L1 represents a single bond, or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of this disclosure, L1 represents a single bond, or an unsubstituted (C6-C18) arylene. For example, L1 may be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.

[0058] In Equation 1, R 31 and R 32 Each independently represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, R 31 and R 32 Each independently represents a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of this disclosure, R 31 and R 32Each independently represents an unsubstituted (5- to 18-membered) heteroaryl group, or a heteroaryl group substituted with at least one of one (C6-C18) aryl groups and one (5- to 18-membered) heteroaryl groups. Specifically, R 31 and R 32 Each can independently be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzofuranopyridyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl. For example, R 31 and R 32 Each can be independently an unsubstituted dibenzofuranyl, dibenzothiophenyl, benzofuran-pyridyl, benzonaphthofuranyl, or benzonaphthothiophenyl.

[0059] In Formula 1, R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, R1 represents a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group. According to another embodiment of this disclosure, R1 represents an unsubstituted (C6-C15) aryl group, or an unsubstituted (5- to 15-membered) heteroaryl group. For example, R1 can be phenyl, biphenyl, pyridyl, quinolinyl, or isoquinolinyl.

[0060] In Formula 1, R2 to R5 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, or substituted or unsubstituted di(C1-C30) alkylsilyl. Alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused-ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N(Ar1)(Ar2); or may be attached to adjacent substituents to form one or more rings. For example, two R2s, two R3s, two R4s, R2 and R3, R3 and R4, R5 and R2, and / or R5 and R4 may be connected to each other to form one or more rings. According to one embodiment, R2 to R4 each independently represent hydrogen.

[0061] In Formula 1, L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene.

[0062] Ar1 and Ar2 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, 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- to 30-membered) heteroaryl.

[0063] In Equation 1, a and b each independently represent an integer of 1 or 2, and c represents an integer from 1 to 3, wherein if a to c are integers of or greater, then each R2, each R3, and each R4 may be the same or different.

[0064] According to one embodiment of this disclosure, Formula 1 can be represented by at least one of Formulas 1-1 and 1-2 below.

[0065]

[0066] In equations 1-1 and 1-2, X1, Y1, L1, R 31 R 32 R1 to R4 and a to c are defined as in Equation 1.

[0067] In Formula 2, HAr represents a substituted or unsubstituted (3- to 20-membered) heteroaryl group containing one or more nitrogen atoms. According to one embodiment of this disclosure, HAr represents a substituted or unsubstituted (3- to 15-membered) heteroaryl group containing one or more nitrogen atoms. According to another embodiment of this disclosure, HAr represents an unsubstituted (5- to 15-membered) heteroaryl group containing one or more nitrogen atoms. Specifically, HAr can be pyridinyl, pyrimidinyl, triazinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pyridopyrazinyl, benzoquinazolinyl, benzoquinoxalinyl, benzofuranopyrimidinyl, etc.

[0068] In Formula 2, L2 independently represents a single bond, or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of this disclosure, L2 independently represents a substituted or unsubstituted (C6-C20) arylene. According to another embodiment, L2 independently represents an unsubstituted (C6-C20) arylene or a (C6-C20) arylene substituted with one or more (C6-C20) arylene groups. Specifically, L2 can independently be an unsubstituted or naphthyl-substituted phenylene, naphthylene, biphenylene, phenylnaphthylene, naphthylphenylene, etc.

[0069] In Formula 2, Ar2 independently represents a substituted or unsubstituted (C6-C30) aryl group, or Formula 3 or 4. According to one embodiment of this disclosure, Ar2 independently represents a (C6-C30) aryl group substituted with one or more (C1-C6) alkyl groups; a (C6-C30) aryl group substituted with a (5- to 15-membered) heteroaryl group, said heteroaryl group being substituted with one or more (C6-C12) aryl groups; a (C6-C30) aryl group substituted with one or more di(C6-C12) arylamino groups; an unsubstituted (C6-C30) aryl group; or Formula 3 or 4. Specifically, Ar2 can be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenanthrene, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, phenyl substituted with one or more phenylquinoxalinyl groups, phenyl substituted with one or more diphenylamino groups, phenyl substituted with one or more naphthyl groups, formula 3 or 4, etc.

[0070] In Equation 3, Y represents O, S, N-*, or NR. 21 ; and * indicates the site connected to L2.

[0071] In Equation 3, R 21 This indicates a substituted or unsubstituted (C6-C30) aryl group. According to one embodiment of this disclosure, R... 21 This indicates a substituted or unsubstituted (C6-C18) aryl group. According to another embodiment of this disclosure, R... 21 This indicates an unsubstituted (C6-C12) aryl group. Specifically, R 21 It can be phenyl, etc.

[0072] In Equation 3, R 11 To R 18 Each can independently represent a site linked to L2; or 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) The group may contain alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L4-N(Ar3)(Ar4); or may be attached to adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R 11 To R 18Each independently represents a site linked to L2; or represents hydrogen, a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, R 11 To R 18 Each can independently represent a site linked to L2; or represent hydrogen or an unsubstituted (C6-C18) aryl group. For example, R 11 To R 18 Each can be an independent site connected to L2; or it can be hydrogen, phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, etc.

[0073] In Equation 4, X 31 To X 42 Each can be represented independently as N or CR. a For example, X 31 To X 42 Each can be CR independently a .

[0074] R a Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30) 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 fused-ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L5-N(Ar5)(Ar6); or may be attached to adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R a Each can independently represent hydrogen, or a substituted or unsubstituted (C6-C12) aryl group; or can be attached to an adjacent substituent to form one or more rings. According to another embodiment of this disclosure, R a Each can independently represent hydrogen or an unsubstituted (C6-C12) aryl group; or it can be attached to an adjacent substituent to form one or more rings. Specifically, R a Each can be hydrogen, phenyl, etc., independently; or it can be attached to an adjacent substituent to form a benzene ring, etc.

[0075] L4 and L5 independently represent single-bonded, substituted or unsubstituted (C6-C30) aryl groups, or substituted or unsubstituted (3- to 30-membered) heteroaryl groups.

[0076] Ar3 to Ar6 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, 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.

[0077] In Equation 2, d represents an integer from 1 to 3, where if d is an integer of 2 or greater, then each ((L2)) e -Ar2) can be the same or different. For example, d can be an integer of 2 or 3, and each ((L2)) e -Ar2) can be the same or different.

[0078] In Equation 2, e represents an integer from 0 to 2, where if e is an integer of 2, then each L2 can be the same or different.

[0079] In Equation 4, * represents the site connected to L2.

[0080] According to one embodiment of this disclosure, formula 2 can be represented by at least one of formulas 2-1 to 2-3 below.

[0081]

[0082] In equations 2-1 to 2-3, A1 to A 24 Each represents CR independently. 10 Or N, where at least one of A1 to A6 represents N, and A7 to A 14 At least one of them represents N, and A 15 To A 24 At least one of A1 to A6 represents N. According to one embodiment of this disclosure, one to three of A1 to A6 represent N, and the remaining portions of A1 to A6 represent CR. 10 According to another embodiment of this disclosure, A7 to A 14 One to three in the string represent N, and A7 to A 14 The remaining part represents CR 10 According to another embodiment of this disclosure, A 15 To A 24 The two in the text represent N, and A 15 To A 24 The remaining part represents CR 10 .

[0083] R 10 Each can independently represent hydrogen or -L2-Ar2; or two adjacent Rs. 10 They can be connected to each other to form one or more loops, where if there are multiple R... 10 Then each R 10 They can be the same or different. According to one embodiment of this disclosure, R 10 Each can independently represent hydrogen or -L2-Ar2, where if multiple R are present... 10 Then each R 10 They can be the same or different. For example, R 10 Each can independently represent hydrogen or -L2-Ar2; or two adjacent Rs. 10 They can connect with each other to form a benzofuran ring.

[0084] In equations 2-1 to 2-3, L2, Ar2, d, and e are defined as in equation 2.

[0085] The compound represented by Formula 1 may be selected from at least one of the following compounds, but is not limited thereto.

[0086]

[0087]

[0088] The compound represented by Formula 2 may be selected from at least one of the following compounds, but is not limited thereto.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] A combination of at least one of compounds H-1 to H-28 with at least one of compounds C-1 to C-325 can be used in organic electroluminescent devices.

[0103] According to one embodiment of this disclosure, the disclosure may provide a compound represented by Formula 1 or a compound represented by Formula 2. Specifically, the disclosure may provide at least one compound selected from compounds H-1 to H-28 and compounds C-1 to C-325.

[0104] The organic electroluminescent compound disclosed herein can be represented by the following formula 2-1.

[0105]

[0106] In Equation 2-1,

[0107] X a Indicates O or S;

[0108] Ar a and Ar b Each can independently represent a substituted or unsubstituted (C6-C18) aryl group, provided that Ar... a and Ar b At least one of them represents a substituted or unsubstituted naphthyl group; and

[0109] R1 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or combinations thereof.

[0110] For example, Ar a and Ar b Each can independently be an unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted naphthyl, or a naphthyl substituted with one or more phenyl groups, provided that Ar a and Ar b At least one of them can be an unsubstituted naphthyl or a naphthyl substituted with one or more phenyl groups.

[0111] For example, R1 to R6 can each independently be hydrogen, naphthyl, naphthylphenyl, or phenylnaphthyl, provided that at least one of R1 to R6 can be naphthyl, naphthylphenyl, or phenylnaphthyl.

[0112] Specifically, the compounds represented by Formula 2-1 can be exemplified as the following compounds, but are not limited thereto.

[0113]

[0114] The compounds represented by Formula 1 according to this disclosure can be produced by synthetic methods known to those skilled in the art, and for example, by referring to Korean Patent Application Publication No. 2017-0022865 (published on March 2, 2017), but are not limited thereto.

[0115] The compounds represented by Formula 2 of this disclosure can be produced by synthetic methods known to those skilled in the art. For example, compounds represented by any of Formulas 2-1 to 2-3 can be produced by referring to the following reaction schemes 1 to 3, but are not limited thereto:

[0116] [Reaction Scheme 1]

[0117]

[0118] [Reaction Scheme 2]

[0119]

[0120] [Reaction Scheme 3]

[0121]

[0122] In the reaction scheme, L2, Ar2, d, and e are as defined in Equation 2, and A1 to A 24 It is defined as in equations 2-1 to 2-3.

[0123] Although illustrative synthetic examples of the compounds represented by Formula 2 of this disclosure 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 continue even if substituents defined in Formula 2 above but not specified in the specific synthetic examples are bonded.

[0124] The organic electroluminescent device according to the present disclosure has a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode.

[0125] One of the first and second electrodes can be an anode, and the other can be a cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the following: 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. The second electrode can be a semi-transparent reflective electrode or a reflective electrode, and depending on the material, it can be a top-emitting, bottom-emitting, or side-emitting type. Furthermore, 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.

[0126] The organic electroluminescent device according to this disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may contain a variety of organic electroluminescent materials, including 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 this disclosure, the organic electroluminescent device may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer may contain a compound represented by Formula 1 and a compound represented by Formula 2, preferably a variety of host materials disclosed herein.

[0127] The light-emitting layer includes a host and a dopant, wherein the host comprises a variety of host materials, and a compound represented by Formula 1 may be included as a first host compound of the variety of host materials, and a compound represented by Formula 2 may be included as a second host compound of the variety of host materials. 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.

[0128] In this document, the light-emitting layer is the layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. All the first host material and the second host material may be contained in one layer, or the first host material and the second host material may be contained in their respective separate light-emitting layers. According to one embodiment of this disclosure, the doping concentration of the dopant compound in the light-emitting layer relative to the host compound may be less than 20 wt%.

[0129] The organic electroluminescent device of this disclosure may further comprise at least one layer selected from the following: 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, the organic electroluminescent device may further comprise at least one amine-based compound, other than the various host materials of this disclosure, as a hole injection material, hole transport material, hole assist material, light-emitting material, light-emitting assist material, and electron blocking material. Furthermore, according to one embodiment of this disclosure, the organic electroluminescent device may further comprise at least one azazine-based compound, other than the various host materials of this disclosure, as an electron transport material, electron injection material, electron buffer material, and hole blocking material.

[0130] The dopant included in the organic electroluminescent device of this disclosure may be at least one phosphorescent dopant or a fluorescent dopant, and preferably at least one phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but may preferably be selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, more preferably from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, and even more preferably from ortho-metallized iridium complexes.

[0131] The dopants included in the organic electroluminescent devices of this disclosure may include, but are not limited to, compounds represented by the following formula 101.

[0132]

[0133] In Equation 101, L is selected from the following structures 1 to 3:

[0134]

[0135] R 100 To R 103 Each 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, benzothienoquinoline, or indenequinoline;

[0136] R 104 To R 107Each 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;

[0137] 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

[0138] n represents an integer from 1 to 3.

[0139] Specific examples of dopant compounds are shown below, but are not limited to.

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] In the organic electroluminescent device of this disclosure, 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 multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be multilayered.

[0146] 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 each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each of the multilayers can use multiple compounds.

[0147] Furthermore, the organic electroluminescent compounds or various host materials according to this disclosure can also be used in organic electroluminescent devices containing quantum dots (QDs).

[0148] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0149] 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 can dissolve or diffuse and in which there are no problems with film-forming ability.

[0150] The first and second host compounds of this disclosure can be deposited as 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 chamber to evaporate the materials. Furthermore, if the first and second host compounds are present in the same or different layers of the organic electroluminescent device, the two host compounds can be deposited individually as films. For example, the second host compound can be deposited after the first host compound is deposited.

[0151] This disclosure provides a display system by comprising a compound represented by Formula 2-1 or by using a variety of host materials comprising a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display system or a lighting system can be manufactured by using the organic electroluminescent compounds or the variety of host materials disclosed herein. Specifically, by using the organic electroluminescent compounds or the variety of host materials disclosed herein, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be produced; or lighting systems, such as outdoor or indoor lighting systems.

[0152] In the following sections, the preparation methods of the compounds according to this disclosure and the properties of the compounds will be explained in detail with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0153] Example 1: Preparation of compound C-295

[0154]

[0155] Synthesis of Compound 1-1

[0156] In a flask, 2-bromo-7-chlorodibenzo[b,d]furan (10 g, 35.17 mmol), (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxacyclopentaborane) (14 g, 53.5 mmol), PdCl2(PPh3)2 (2.5 g, 3.57 mmol), and KOAc (8.78 g, 89.25 mmol) were dissolved in 180 mL of 1,4-dioxane, and the mixture was refluxed at 150 °C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 9 g of compound 1-1 (yield: 76.8%).

[0157] Synthesis of Compounds 1-2

[0158] In a flask, compound 1-1 (9 g, 27.4 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (9.6 g, 30 mmol), K₂CO₃ (9.46 g, 68.5 mmol), and Pd(PPh₃)₄ (1.58 g, 1.37 mmol) were dissolved in 137 mL of toluene, 68.5 mL of ethanol, and 68.5 mL of water, and the mixture was refluxed at 140 °C for 12 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10 g of compound 1-2 (yield: 75.5%).

[0159] Synthesis of compound C-295

[0160] In a flask, compounds 1-2 (5 g, 10.3 mmol), (naphthyl-2-yl)boric acid (2.13 g, 12.4 mmol), Pd2(dba)3 (417 mg, 0.515 mmol), S-Phos (423 mg, 1.03 mmol), and NaOtBu (2.5 g, 25.75 mmol) were dissolved in 50 mL of xylene, and the mixture was refluxed at 160 °C for 1 hour. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 3.8 g of compound C-295 (yield: 64.1%).

[0161] C-295 575.2 295℃

[0162] Example 2: Preparation of compound C-304

[0163]

[0164] In a flask, compounds 1-2 (5 g, 10.3 mmol), (naphthyl-2-yl)boric acid (2.13 g, 12.4 mmol), Pd2(dba)3 (417 mg, 0.515 mmol), S-Phos (423 mg, 1.03 mmol), and NaOtBu (2.5 g, 25.75 mmol) were dissolved in 50 mL of xylene, and the mixture was refluxed at 160 °C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.1 g of compound C-304 (yield: 18.6%).

[0165] C-304 575.2 239.5℃

[0166] Example 3: Preparation of compound C-296

[0167]

[0168] Synthesis of compound 3-1

[0169] In a flask, 8-bromo-1-chlorodibenzo[b,d]furan (10 g, 35.17 mmol), (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxacyclopentaborane) (14 g, 53.5 mmol), PdCl2(PPh3)2 (2.5 g, 3.57 mmol), and KOAc (8.78 g, 89.25 mmol) were dissolved in 180 mL of 1,4-dioxane, and the mixture was refluxed at 150 °C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 9.2 g of compound 3-1 (yield: 78.5%).

[0170] Synthesis of compound 3-2

[0171] In a flask, compound 3-1 (9.2 g, 28 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (10.2 g, 32.2 mmol), K₂CO₃ (9.67 g, 70 mmol), and Pd(PPh₃)₄ (1.61 g, 1.4 mmol) were dissolved in 140 mL of toluene, 70 mL of ethanol, and 70 mL of water, and the mixture was refluxed at 140 °C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10 g of compound 3-2 (yield: 73%).

[0172] Synthesis of compound C-296

[0173] In a flask, compound 3-2 (5 g, 10.3 mmol), (naphthyl-2-yl)boric acid (2.13 g, 12.4 mmol), Pd2(dba)3 (417 mg, 0.515 mmol), S-Phos (423 mg, 1.03 mmol), and K3PO4 (5.47 g, 25.75 mmol) were dissolved in 50 mL of xylene, and the mixture was refluxed at 160 °C for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.5 g of compound C-296 (yield: 75.9%).

[0174] C-296 575.2 227.4℃

[0175] Example 4: Preparation of compound C-325

[0176]

[0177] Synthesis of compound 4-1

[0178] In a flask, (1-chlorodibenzo[b,d]furan-2-yl)boronic acid (10 g, 20.6 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (14 g, 44.4 mmol), K₂CO₃ (14 g, 101.5 mmol), and Pd(PPh₃)₄ (2.4 g, 2.03 mmol) were dissolved in 200 mL toluene, 100 mL ethanol, and 100 mL water, and the mixture was refluxed at 140 °C for 1 hour. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 10 g of compound 4-1 (yield: 87.9%).

[0179] Synthesis of compound C-325

[0180] In a flask, compound 4-1 (7 g, 14.48 mmol), (naphth-2-yl)boric acid (3.74 g, 21.7 mmol), Pd2(dba)3 (663 mg, 0.724 mmol), S-Phos (595 mg, 1.448 mmol), and K3PO4 (7.7 g, 36.2 mmol) were dissolved in 72 mL of xylene, and the mixture was refluxed at 160 °C for 1 hour. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 4.6 g of compound C-325 (yield: 55.2%).

[0181] C-325 575.2 265.1℃

[0182] Example 5: Preparation of compound C-312

[0183]

[0184] In a flask, compounds 4-1 (4.2 g, 8.69 mmol), 5-1 (3.1 g, 9.56 mmol), Pd(PPh3)4 (502 mg, 0.434 mmol), and K2CO3 (3 g, 21.75 mmol) were dissolved in 50 mL of toluene, 25 mL of ethanol, and 25 mL of water, and the mixture was refluxed at 130 °C for 8 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, and residual water was removed using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.8 g of compound C-312 (yield: 31.8%).

[0185] C-312 651.23 201.6℃

[0186] In the following sections, methods for producing organic electroluminescent devices (OLEDs) comprising organic electroluminescent compounds or various host materials according to the present disclosure, as well as the characteristics of said organic electroluminescent devices, will be explained in detail with reference to representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.

[0187] Device Examples 1 to 6: Production of Red OLEDs with various host materials according to the present disclosure as the substrate

[0188] OLEDs according to this disclosure are produced. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1, shown in Table 3, is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1, shown in Table 3, is introduced into another chamber of the vacuum vapor deposition apparatus. The two materials are evaporated at different rates, and compound HI-1 is deposited at a doping amount of 3 wt% based on the total amount of compounds HI-1 and HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Compound HT-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: the first and second host compounds shown in Table 1 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 1:1 rate, and the dopant material was evaporated simultaneously at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of host and dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Compounds ET-1 and EI-1 were evaporated at a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI-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. All materials used in the production of the OLED were [not specified in the original text]. -6 Purification is achieved through vacuum sublimation.

[0189] Comparative Examples 1 to 5: Production of OLEDs Containing Comparative Compounds as the Main Body

[0190] The OLED is produced in the same manner as in Device Example 1, except that only the host compound shown in Table 1 below is used as the single host for the emitting layer.

[0191] Table 1 below provides the driving voltage, luminous efficiency, and emission color of the OLEDs produced in Device Examples 1 to 6 and Comparative Examples 1 to 5 at a brightness of 1,000 nits, as well as the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits.

[0192] [Table 1]

[0193]

[0194] As can be seen from Table 1 above, OLEDs comprising multiple host materials exhibit excellent driving voltage, luminous efficiency, and / or lifetime characteristics, wherein the multiple host materials comprise specific combinations of compounds according to this disclosure. This result represents a significantly improved effect compared to OLEDs using only each of the first and second host materials.

[0195] Comparative Example 6: Production of OLEDs Containing Comparative Compounds as the Main Body

[0196] The OLED was produced in the same manner as in Device Example 1, except that only the host compounds shown in Table 2 below were used as the host for the light-emitting layer.

[0197] Apparatus Examples 7 to 9: Production of Red OLEDs with Compounds Based on the Present Disclosure as the Main Body

[0198] The OLED was produced in the same manner as in Comparative Example 6, except that only the host compounds shown in Table 2 below were used as the host for the emitting layer.

[0199] Table 2 below provides the driving voltage, power efficiency, and emission color of the OLEDs produced in Comparative Example 6 and Device Examples 7 to 9 at a brightness of 1,000 nits.

[0200] [Table 2]

[0201]

[0202] As can be seen from Table 2 above, compared with OLEDs containing the comparative compounds, OLEDs containing the compounds according to this disclosure have superior driving voltage and power efficiency characteristics.

[0203] The compounds used in the apparatus examples and comparative examples are shown in Table 3.

[0204] [Table 3]

[0205]

Claims

1. A plurality of host materials, said plurality of host materials comprising a first host material and a second host material, the first host material comprising a compound represented by formula 1 below, and the second host material comprising a compound represented by formula 2 below: ----- (1) In Equation 1, X1 and Y1 can each independently represent -N=, -O-, or -S-, provided that one of X1 and Y1 represents -N= and the other of X1 and Y1 represents -O- or -S-. L1 represents a single bond, or a substituted or unsubstituted (C6-C30) aryl group; R 31 and R 32 Each can be used independently to represent a substituted or unsubstituted (3 to 30) heteroaryl group; R1 represents a substituted or unsubstituted (C6-C30) aryl group; R2 to R4 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, or -L3-N(Ar1)(Ar2); or may be attached to adjacent substituents to form one or more rings; L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar1 and Ar2 each independently represent 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; and a and b each independently represent an integer of 1 or 2, and c represents an integer from 1 to 3, where if a to c are integers of 2 or greater, then each R2, each R3, and each R4 can be the same or different; ----- (2) In Equation 2, HAr indicates a substituted or unsubstituted (3- to 20-membered) heteroaryl group containing one or more nitrogen atoms; L2 independently represents substituted or unsubstituted (C6-C30) aryl groups; Ar2 represents the following equation 3: ----- (3) Y represents O or S; R 11 To R 18 Each can independently represent a site connected to L2; or 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; or can be attached to an adjacent substituent to form one or more rings; L4 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; d represents an integer from 1 to 3, where if d is an integer of 2 or greater, then each ((L2)) e -Ar2) can be the same or different; e represents an integer from 0 to 2, where if e is an integer of 2, then each L2 can be the same or different; and Indicates the site connected to L2. in, The substituted alkyl group, the substituted alkenyl group, the substituted aryl group, the substituted arylene group, the substituted heteroaryl group, the substituted heteroarylene group, the substituted heteroaryl group containing one or more nitrogen atoms, the substituted cycloalkyl group, and the substituted fused ring group of the 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; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2- (C30) alkynyl; (C1-C30) alkoxy; unsubstituted or (3- to 30-membered) heteroaryl substituted with one or more (C6-C30) aryl groups; unsubstituted or (C6-C30) aryl substituted with at least one of one or more (C1-C30) alkyl groups and one or more (3- to 30-membered) heteroaryl groups; tri(C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyl di(C6-C30) arylsilyl.

2. The various main body materials according to claim 1, wherein, Equation 1 is represented by at least one of the following equations 1-1 and 1-2: ----- (1-1) ----- (1-2) Where X1, Y1, L1, R 31 R 32 R1 to R4 and a to c are as defined in claim 1.

3. The various main body materials according to claim 1, wherein, Equation 2 is represented by at least one of the following equations 2-1 to 2-3: ----- (2-1) ----- (2-2) ----- (2-3) in A1 to A 24 Each represents CR independently. 10 Or N, where at least one of A1 to A6 represents N, and A7 to A 14 At least one of them represents N, and A 15 To A 24 At least one of them represents N; R 10 Each can independently represent hydrogen or -L2-Ar2, where if multiple R are present... 10 Then each R 10 They can be the same or different; and L2, Ar2, d, and e are as defined in claim 1.

4. The various main body materials according to claim 1, wherein, R 31 and R 32 Each is independently a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzofuranopyridyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

5. The various main body materials according to claim 1, wherein, The compound represented by Formula 1 is selected from at least one of the following compounds: 。 6. The various main body materials according to claim 1, wherein, The compound represented by Formula 2 is selected from at least one of the following compounds: and .

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

8. An organic electroluminescent compound, represented by the following formula 2-1: ----- (2-1) in X a Indicates O or S; Ar a and Ar b Each can independently represent a substituted or unsubstituted (C6-C18) aryl group, provided that Ar... a and Ar b At least one of them represents a substituted or unsubstituted naphthyl group; and R1 and R3 through R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or combinations thereof; R2 represents a substituted or unsubstituted naphthyl group. The substituted (C6-C18) aryl, the substituted naphthyl, and the substituted phenyl groups are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; unsubstituted or substituted with one or more (C6-C30) aryl groups. Substituted (3- to 30-membered) heteroaryl; unsubstituted or (C6- to 30-membered) aryl substituted with at least one of one or more (C1- to C30) alkyl and one or more (3- to 30-membered) heteroaryl; tri(C1- to C30) alkylsilyl; tri(C6- to C30) arylsilyl; di(C1- to C30) alkyl(C6- to C30) arylsilyl; (C1- to C30) alkyldi(C6- to C30) arylsilyl.

9. The organic electroluminescent compound according to claim 8, wherein, The compound represented by Formula 2-1 is selected from the following compounds: 。 10. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 8.

11. The organic electroluminescent device according to claim 10, wherein, The organic electroluminescent compound is contained in the light-emitting layer.

12. An organic electroluminescent compound, represented by the following formula 2-1: ----- (2-1) in X a Indicates O or S; Ar a and Ar b Each can independently represent a substituted or unsubstituted (C6-C18) aryl group, provided that Ar... a and Ar b At least one of them represents a substituted or unsubstituted naphthyl group; and R1 to R3, R5 and R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or combinations thereof; R4 indicates a substituted or unsubstituted naphthyl group. The substituted (C6-C18) aryl, the substituted naphthyl, and the substituted phenyl groups are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; unsubstituted or substituted with one or more (C6-C30) aryl groups. Substituted (3- to 30-membered) heteroaryl; unsubstituted or (C6- to 30-membered) aryl substituted with at least one of one or more (C1- to C30) alkyl and one or more (3- to 30-membered) heteroaryl; tri(C1- to C30) alkylsilyl; tri(C6- to C30) arylsilyl; di(C1- to C30) alkyl(C6- to C30) arylsilyl; (C1- to C30) alkyldi(C6- to C30) arylsilyl.

13. The organic electroluminescent compound according to claim 12, wherein, The compound represented by Formula 2-1 is selected from the following compounds: 。 14. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 12.

15. The organic electroluminescent device according to claim 14, wherein, The organic electroluminescent compound is contained in the light-emitting layer.

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