Organic electroluminescent compounds, multiple host materials, and organic electroluminescent devices containing these.

Abstract

To provide an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device including the same.SOLUTION: A plurality of host materials includes a first host material containing a compound represented by Formula 1 below and a second host material containing a compound represented by Formula 2 below. -----(1) HAr-((L2)e-Ar2)d-----(2)SELECTED DRAWING: None

Description

[Technical Field]

[0001] This disclosure relates to organic electroluminescent compounds, a plurality of host materials, and organic electroluminescent devices comprising these. [Background technology]

[0002] Small molecule green organic electroluminescent devices (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 progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials that have excellent luminescence efficiency in panel mounting. However, in many applications such as TVs and lighting, the lifespan of OLEDs is insufficient, and higher efficiency of OLEDs is still needed. Typically, the higher the brightness of an OLED, the shorter its lifespan. Therefore, OLEDs with high luminescence efficiency and / or long lifespan characteristics are required for long-term use and high resolution displays.

[0003] Various materials or concepts have been proposed for the organic layer of OLEDs to improve luminous efficiency, driving voltage, and / or lifespan. However, these have not been sufficient for practical application.

[0004] Patent Document 1 discloses OLEDs that use phenanthroxazole compounds and phenanthrothiazole compounds as hosts. However, the aforementioned reference does not specifically disclose any particular combination of the multiple host materials of this disclosure. In addition, the development of host materials to improve the performance of OLEDs is still needed. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Korean Patent Application Publication No. 2017-0022865 Specification [Overview of the project] [Problems that the invention aims to solve]

[0006] An object of this disclosure is to provide organic electroluminescent compounds having novel structures suitable for application to organic electroluminescent devices. Another object of this disclosure is to provide improved organic electroluminescent materials that can provide organic electroluminescent devices having improved drive voltage, luminous efficiency, and / or lifetime characteristics. A further object of this disclosure is to provide organic electroluminescent devices having lower drive voltage, higher luminous efficiency, and / or improved lifetime characteristics by including the compounds of this disclosure as a single host material, or specific combinations of the compounds of this disclosure as multiple host materials. [Means for solving the problem]

[0007] As a result of intensive research to solve the technical problems, the inventors have found that the above objective is expressed in the following formula 2-1: [ka] (In the formula, X a represents O or S; Ar a and Ar b Each of these independently represents a substituted or unsubstituted (C6-C18) aryl, however, Ar a and Ar b The condition is that at least one of them represents a substituted or unsubstituted naphthyl; R1 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or a combination thereof. We found that this can be achieved by an organic electroluminescent compound represented by [formula].

[0008] In addition, the inventors noticed that core-containing compounds such as phenanthroxazole or phenanthrothiazole have unusually low minimum unoccupied molecular orbital (LUMO) energies compared to typical hole-type hosts, and they studied hole-type hosts that could form an appropriate energy gap using the above compounds. As a result, the inventors found that using a combination of the compound represented by Formula 1 and the compound represented by Formula 2 in the light-emitting layer balances the hole-electron properties with appropriate HOMO and LUMO energy levels, thereby yielding an organic electroluminescent device with lower drive voltage, higher luminescence efficiency, and / or longer lifetime characteristics compared to conventional organic electroluminescent devices.

[0009] Specifically, the present inventors have found that the above objective can be achieved by a plurality of host materials, including a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by the following formula 2. [ka]

[0010] 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 represents -NR5-, -O-, or -S-; L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene; R 31 and R 32 Each of these independently represents a substituted or unsubstituted (3-30 member) heteroaryl; R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R2 to R5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30-membered) heteroaryl, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (C1 - C30) alkoxy, substituted or unsubstituted tri(C1 - C30) alkylsilyl, substituted or unsubstituted di(C1 - C30) alkyl(C6 - C30) arylsilyl, substituted or unsubstituted (C1 - C30) alkyldi(C6 - C30) arylsilyl, substituted or unsubstituted tri(C6 - C30) arylsilyl, a substituted or unsubstituted condensed ring group of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, or -L3-N(Ar1)(Ar2), or may be linked with adjacent substituents to form a ring; L3 each independently represents a single bond, substituted or unsubstituted (C6 - C30) arylene, or substituted or unsubstituted (3 - 30-membered) heteroarylene; Ar1 and Ar2 each independently represent hydrogen, substituted or unsubstituted (C1 - C30) alkyl, substituted or unsubstituted (C2 - C30) alkenyl, a substituted or unsubstituted condensed ring group of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, substituted or unsubstituted (C6 - C30) aryl, or substituted or unsubstituted (3 - 30-membered) heteroaryl; a and b each independently represent an integer of 1 or 2, c represents an integer of 1 - 3, where when a - c are integers of 2 or more, each of R2, each of R3, and each of R4 may be the same or different. HAr - ((L2) e -Ar2) d ----- (2)

[0011] In formula 2, HAr represents a substituted or unsubstituted (3 - 20-membered) heteroaryl containing a nitrogen atom; L2 each independently represents substituted or unsubstituted (C6 - C30) arylene;[[ID=二十一]] Ar2 independently represents a substituted or unsubstituted (C6-C30) aryl, or one of the following formulas 3 or 4; [ka] Y is O, S, N-*, or NR 21 It represents; R 21 This represents a substituted or unsubstituted (C6-C30) aryl; R 11 ~R 18 Each of these independently represents a position linked to L2, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L4-N(Ar3)(Ar4), or may be linked to an adjacent substituent to form a ring; X 31 ~X 42 Each is independently N or CR a It represents; R aEach of these independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L5-N(Ar5)(Ar6), or may be linked with adjacent substituents to form a ring; L4 and L5 independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar3 to Ar6 each independently represent hydrogen, a substituted or unsubstituted (C1 to C30) alkyl group, a substituted or unsubstituted (C2 to C30) alkenyl group, a substituted or unsubstituted fused ring group of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl group, or a substituted or unsubstituted (3 to 30-membered) heteroaryl group; d represents an integer between 1 and 3, and if d is an integer greater than or equal to 2, then ((L2) e Each of the elements in -Ar2) may be the same or different; e represents an integer between 0 and 2, and if e is an integer of 2, then each of L2 may be the same or different; * indicates the connection point to L2.

[0012] Advantageous effects of the invention The organic electroluminescent compounds according to this disclosure exhibit suitable performance for use in organic electroluminescent devices. In addition, by including the compounds according to this disclosure as a single host material, or specific combinations of the compounds according to this disclosure as multiple host materials, it is possible to provide organic electroluminescent devices having lower drive voltages, higher luminous efficiency, and / or improved lifetime characteristics compared to conventional organic electroluminescent devices, and to manufacture display or lighting devices using such devices. [Modes for carrying out the invention]

[0013] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present invention and is not intended to limit the scope of the present disclosure.

[0014] In this disclosure, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and may be included in any layer constituting the organic electroluminescent device as needed.

[0015] In this disclosure, the term "organic electroluminescent material" means a material that may contain at least one compound and can be used in an organic electroluminescent device. The organic electroluminescent material may be included in any layer constituting the organic electroluminescent device, as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emission 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, and the like.

[0016] In this disclosure, the term “multiple organic electroluminescent materials” means an organic electroluminescent material comprising a combination of at least two compounds that may be contained in any layer constituting an organic electroluminescent device. It may mean both the material before it is contained in the organic electroluminescent device (e.g., before deposition) and the material after it is contained in the organic electroluminescent device (e.g., after deposition). For example, the multiple organic electroluminescent materials of this disclosure may be a combination of at least two compounds that may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emission auxiliary layer, an electron blocking layer, a light emission layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. These at least two compounds may be contained in the same layer or in different layers by methods used in the art. For example, the at least two compounds may be evaporated together or co-evaporated, or evaporated separately.

[0017] In this disclosure, the term “multiple host materials” means host materials comprising a combination of at least two compounds that may be included in any light-emitting layer constituting an organic electroluminescent device. It may mean both materials before inclusion in the organic electroluminescent device (e.g., before deposition) and materials after inclusion in the organic electroluminescent device (e.g., after deposition). For example, the multiple host materials of this disclosure may be a combination of at least two host materials and may selectively further include conventional materials included in the organic electroluminescent material. The multiple host materials of this disclosure may be included in any light-emitting layer constituting an organic electroluminescent device. At least two compounds included in the multiple host materials of this disclosure may be included together in one light-emitting layer, or each may be included in different light-emitting layers by methods used in the art. For example, at least two compounds may be evaporated together or co-evaporated, or evaporated separately.

[0018] In this specification, the term "(C1-C30) alkyl" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc. The term "(C2-C30) alkenyl" means a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbuta-2-enyl, etc. The term "(C2~C30) alkynyl" refers to a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. The above alkynyls may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpenta-2-inyl, etc. The term "(C3~C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The above cycloalkyls may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3-7 member) heterocycloalkyl" means a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeleton atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of O, S, and N. Examples of the above heterocycloalkyl include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The term "(C6-C30) aryl(ene)" means a monocyclic ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, where the number of ring skeleton carbon atoms isPreferably, there are 6 to 20 aryl(ene) groups. The above aryl(ene) groups may be partially saturated and may also contain spiro structures. Examples of the above aryl groups include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenantrenyl, phenylphenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, and the like. More specifically, the above aryls include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3- Biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl,9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11 ,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl- 5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl Luorenyl, 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-1 0-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 Examples include fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenantrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenantrenyl, and 9,9,10,10-tetramethyl-9,10-dihydro-4-phenantrenyl.

[0019] The term "(3-30 member) heteroaryl(ene)" means an aryl(ene) 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, and P. The heteroaryl(ene) may be a monocyclic ring or a fused ring fused with at least one benzene ring; may be partially saturated; may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond; may include a spiro structure. The above heteroaryls include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanil, pyridyl, pyrazinyl, pyrimidinyl, and pyridadinyl, as well as benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, benzonaphthofuranil, benzonaphthothiophenyl, diazadibenzofuranil, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, benzoisoquinolyl, cinnolinyl, quinazolyl, and benzox Nazolinil, quinoxalinil, benzoquinoxalinil, naphthilidinil, triazanaphthyl, benzothienopyrimidinil, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinil, phenothiazinil, phenanthiazinil, benzodioxolyl, dihydroacridinil, pyridopyradinil, benzoflopyridyl, benzoflopyrimidinil, dibenzoselenophenyl, benzofloxinolinil, benzof Loquinazolinil, benzoflonaphthilidinil, naphthoflopyrimidinil, benzothienocinolinil, benzothienocinazolinil, benzothienonaphthilidinil, benzothienopyrimidinil, naphthienopyrimidinil, pyridinoindol, benzopyrimidoindol, benzoflopyrazinil, naphthoflopyrimazinil, benzothienopyrimidinil, naphthienopyrimidinil, pyrazinoindol, benzopyrazinoindol,The heteroaryl compounds may include condensed ring heteroaryls such as benzotriazolephenadinyl, imidazopyridyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, the above heteroaryls may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, and 7-indolidinyl. Doridinyl, 8-Indridinyl, 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-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-furyl, 3-furyl, 2-benzofuranil, 3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5 -Isoquinoryl, 6-Isoquinoryl, 7-Isoquinoryl, 8-Isoquinoryl, 2-Quinoxalinyl, 5-Quinoxalinyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl,Azacarbazolyl-9-yl, 1-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpy Rol-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert-butyl-1-indolly Drill, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl Nyl, 6-naphtho-[1,2-b]-benzofuranil, 7-naphtho-[1,2-b]-benzofuranil, 8-naphtho-[1,2-b]-benzofuranil, 9-naphtho-[1,2-b]-benzofuranil, 10-naphtho-[1,2-b]-benzofuranil, 1-naphtho-[2,3-b]-benzofuranil, 2-naphtho-[2,3-b]-benzofuranil, 3-naphtho-[2,3-b]-benzofuranil, 4-naphtho-[2,3-b]-benzofuranil, 5-naphtho-[2,3-b]-benzofuranil, 6-naphtho-[2,3-b]-benzofuranil,7-Naphtho-[2,3-b]-benzofuranil, 8-Naphtho-[2,3-b]-benzofuranil, 9-Naphtho-[2,3-b]-benzofuranil, 10-Naphtho-[2,3-b]-benzofuranil, 1-Naphtho-[2,1-b]-benzofuranil, 2-Naphtho-[2,1-b]-benzofuranil, 3-Naphtho-[2,1-b]-benzofuranil, 4-Naphtho-[2,1-b]-benzofuranil, 5-Naphtho-[2,1-b]-benzofuranil, 6-Naphtho-[2,1-b]-benzofuranil, 7-Naphtho-[2,1-b]-benzofuranil, 8-Naphtho- [2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl phenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naph To-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl,9-Benzoflo[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-Benzoflo[3,2-d]pyrazinyl, 6-Benzoflo[3,2-d]pyrazinyl, 7-Benzoflo[3,2-d]pyrazinyl, 8-Benzoflo[3,2-d]pyrazinyl, 9-Benzoflo[3,2-d]pyrazinyl, 2-Benzothio[3,2-d] This may include pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. Furthermore, "halogens" include F, Cl, Br, and I.

[0020] The term "(C3-C30) aliphatic ring-(C6-C30) aromatic ring fused ring group" means a ring functional group formed by the fusion of at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms, preferably 3 to 25, more preferably 3 to 18, and at least one aromatic ring having 6 to 30 ring skeleton carbon atoms, preferably 6 to 25, more preferably 6 to 18, ring skeleton carbon atoms. Examples of the above fused ring groups include a fused ring group of at least one benzene ring and at least one cyclohexane ring, and a fused ring group of at least one naphthalene ring and at least one cyclopentane ring. The carbon atoms of the (C3-C30) aliphatic ring-(C6-C30) aromatic ring fused ring group may be replaced by at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably from the group consisting of N, O, and S.

[0021] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular 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 bonding of two or more substituents. For example, a "group formed by the bonding of two or more substituents" may be a pyridine-triazine. That is, a pyridine-triazine can be interpreted as a single heteroaryl substituent or as a substituent to which two heteroaryl substituents are bonded. In the formulas of this disclosure, the substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted heteroaryl containing a nitrogen atom, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituents of the substituted condensed ring group of an aliphatic ring and an aromatic ring are, each independently, deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1~C30) alkyl; halo(C1~C30) alkyl; (C2~C30) alkenyl; (C2~C30) alkynyl; (C1~C30) alkoxy; (C1~C30) alkylthio; (C3~C30) cycloalkyl; (C3~C30) cycloalkenyl; (3~7 member) heterocycloalkyl; (C6~C30) aryloxy; (C6~C 30) Arylthio; Unsubstituted or (C6-C30) substituted (3-30 member) heteroaryl; Unsubstituted or (C6-C30) substituted with at least one of (C1-C30) alkyl and (3-30 member) heteroaryl; Tri(C1-C30) alkylsilyl; Tri(C6-C30) arylsilyl; Di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30 )alkyldi(C6~C30)arylsilyl; (C3~C30) fused ring group of an aliphatic ring and an aromatic ring; 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;It is at least one selected from the group consisting of mono- or di-(3-30 member) heteroarylamino; (C1-C30) alkyl(3-30 member) heteroarylamino; (C2-C30) alkenyl(C6-C30) arylamino; (C2-C30) alkenyl(3-30 member) heteroarylamino; (C6-C30) aryl(3-30 member) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphine; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl. According to another embodiment of the present disclosure, each substituent is independently at least one selected from the group consisting of (C1-C10)alkyl; (C6-C20)aryl; (3-20 member) heteroaryls that are unsubstituted or substituted with (C6-C20)aryl; and di(C6-C20)arylaminos. According to another embodiment of the present disclosure, each substituent is independently at least one selected from the group consisting of (C1-C6)alkyl; (C6-C12)aryl; (5-15 member) heteroaryls that are unsubstituted or substituted with (C6-C12)aryl; and di(C6-C12)arylaminos. For example, each substituent may independently be at least one selected from the group consisting of methyl, phenyl, naphthyl, pyridyl, carbazolyl, phenylquinoxalinyl, and diphenylaminos.

[0022] In the formulas of this disclosure, the ring formed by the bonding of adjacent substituents may be a substituted or unsubstituted monocyclic or polycyclic (3-30 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 5-20. According to another embodiment of this disclosure, the number of ring skeleton atoms is 5-15. For example, the fused ring may 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.

[0023] In the formulas of this disclosure, heteroaryl, heteroarylene, and heterocycloalkyl may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 member) 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)alkyl(C6-C30)aryl It may be bonded to at least one selected from the group consisting of silyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino.

[0024] The compounds represented by formulas 1 and 2 are described in detail below.

[0025] In Equation 1, X1 and Y1 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 the present disclosure, one of X1 and Y1 represents -N== and the other of X1 and Y1 represents -O- or -S-. For example, X1 may be -N= and Y1 may be -O- or -S-.

[0026] In Formula 1, L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L1 represents a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L1 represents a single bond or an unsubstituted (C6-C18) arylene. For example, L1 may be a single bond or a substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene.

[0027] In Equation 1, R 31 and R 32 Each of these independently represents a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, R 31 and R 32 Each independently represents a substituted or unsubstituted (5-25 member) heteroaryl. According to another embodiment of the present disclosure, R 31 and R 32 Each of these independently represents an unsubstituted (C6-C18) aryl or (5-18 member) heteroaryl compound that is substituted with at least one of the (C6-C18) aryl and (5-18 member) heteroaryl compounds. Specifically, R 31 and R 32 Each of these may independently be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzoflopyridyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl. For example, R31 and R 32 Each of these may independently be a dibenzofuranyl, dibenzothiophenyl, benzoflopyridyl, benzonaphthofuranyl, or benzonaphthothiophenyl, which are substituted with at least one of phenyl and pyridyl, or are unsubstituted.

[0028] In Formula 1, R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, R1 represents a substituted or unsubstituted (C6-C15) aryl, or a substituted or unsubstituted (5-15 member) heteroaryl. According to another embodiment of the present disclosure, R1 represents an unsubstituted (C6-C15) aryl, or an unsubstituted (5-15 member) heteroaryl. For example, R1 may be phenyl, biphenyl, pyridyl, quinolyl, or isoquinolyl.

[0029] In Formula 1, R2 to R5 may each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3-N(Ar1)(Ar2), or may be linked with adjacent substituents to form a ring. For example, two R2s, two R3s, two R4s, R2 and R3, R3 and R4, R5 and R2, and / or R5 and R4 may be linked together to form a ring. According to one embodiment, R2 to R4 each independently represent hydrogen.

[0030] In Equation 1, L3 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene.

[0031] Ar1 and Ar2 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 a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-30 member) heteroaryl group.

[0032] In Equation 1, a and b each independently represent integers of 1 or 2, and c represents an integer between 1 and 3. Here, if a through c are integers greater than or equal to the above, then each of R2, each of R3, and each of R4 may be the same or different.

[0033] According to one embodiment of the present disclosure, formula 1 may be represented by at least one of the following formulas 1-1 and 1-2. [ka]

[0034] In equations 1-1 and 1-2, X1, Y1, L1, R 31 , R 32 R1 to R4, and a to c are defined as shown in Equation 1.

[0035] In Formula 2, HAr represents a substituted or unsubstituted (3-20 member) heteroaryl compound containing a nitrogen atom. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (3-15 member) heteroaryl compound containing a nitrogen atom. According to one embodiment of the present disclosure, HAr represents an unsubstituted (5-15 member) heteroaryl compound containing a nitrogen atom. Specifically, HAr may be pyridyl, pyrimidinyl, triazinyl, quinolyl, quinazolinyl, quinoxalinyl, naphthylidinyl, pyridopyradinyl, benzoquinazolinyl, benzoquinoxalinyl, benzoflopyrimidinyl, etc.

[0036] In Formula 2, L2 independently represents a single bond or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L2 independently represents a substituted or unsubstituted (C6-C20) arylene. According to another embodiment, L2 independently represents an unsubstituted or (C6-C20) arylene-substituted (C6-C20) arylene. Specifically, L2 independently may be an unsubstituted or naphthyl-substituted phenylene, naphthylene, biphenylene, phenylnaphthylene, or naphthylphenylene.

[0037] In Formula 2, Ar2 independently represents a substituted or unsubstituted (C6-C30) aryl, or Formula 3 or 4. According to another embodiment of the present disclosure, Ar2 independently represents a (C1-C6)alkyl-substituted (C6-C30) aryl; a (C6-C12)aryl-substituted (5-15 member) heteroaryl-substituted (C6-C30) aryl; a di(C6-C12)arylamino-substituted (C6-C30) aryl; an unsubstituted (C6-C30) aryl; or Formula 3 or 4. Specifically, Ar2 may independently be phenyl, naphthyl, phenylnaphthyl, naphthylphenyl, biphenyl, terphenyl, phenantrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, phenyl substituted with phenylquinoxalinyl, phenyl substituted with diphenylamino, phenyl substituted with naphthyl, formula 3 or 4, etc.

[0038] In Equation 3, Y is O, S, N-*, or NR 21 * represents a part connected to L2.

[0039] In Equation 3, R 21 R represents a substituted or unsubstituted (C6-C30) aryl. According to one embodiment of the present disclosure, R 21R represents a substituted or unsubstituted (C6-C18) aryl. According to another embodiment of this disclosure, R 21 This represents unsubstituted (C6-C12) aryl compounds. Specifically, R 21 Phenyle or other similar substances may also be used.

[0040] In Equation 3, R 11 ~R 18 Each of these independently represents a position linked to L2, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L4-N(Ar3)(Ar4), or may be linked with adjacent substituents to form a ring. According to one embodiment of this disclosure, R 11 ~R 18 Each independently represents a position linked to L2, or a hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 member) heteroaryl. According to another embodiment of the present disclosure, R 11 ~R 18 Each of these independently represents a position linked to L2, or a hydrogen atom or an unsubstituted (C6-C18) aryl atom. For example, R 11 ~R 18 Each of these independently represents a position linked to L2, or it may be hydrogen, phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, etc.

[0041] In equation 4, X 31 ~X 42 These are, independently, N or CR.a It represents X. 31 ~X 42 Each of them is independently CR a That's fine.

[0042] R a Each of these independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L5-N(Ar5)(Ar6), or may be linked with adjacent substituents to form a ring. According to one embodiment of the present disclosure, R a Each of these independently represents hydrogen, or a substituted or unsubstituted (C6-C12) aryl, or adjacent substituents can bond to each other to form a ring. According to another embodiment of the present disclosure, R a Each of these elements independently represents hydrogen or an unsubstituted (C6-C12) aryl group; or it can be linked with an adjacent substituent to form an unsubstituted benzene ring. Specifically, R a Each of these substituents may independently be hydrogen or phenyl, or adjacent substituents may be linked to form a benzene ring or the like.

[0043] L4 and L5 independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene.

[0044] Ar3 to Ar6 each independently represent hydrogen, a substituted or unsubstituted (C1 to C30) alkyl group, a substituted or unsubstituted (C2 to C30) alkenyl group, a substituted or unsubstituted fused ring group of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl group, or a substituted or unsubstituted (3 to 30-membered) heteroaryl group.

[0045] In Equation 2, d represents an integer from 1 to 3, and if d is an integer greater than or equal to 2, then each ((L2) e -Ar2) may be the same or different. For example, d may be an integer of 2 or 3, ((L2) e Each of the elements in -Ar2) may be the same or different.

[0046] In Equation 2, e represents an integer between 0 and 2, and when e is an integer of 2, the respective L2s may be the same or different.

[0047] In equation 4, * represents the position connected to L2.

[0048] According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas 2-1 to 2-3. [ka]

[0049] In equations 2-1 to 2-3, A1 to A 24 Each of them operates independently, CR 10 Or it represents N, and at least one of A1 to A6 represents N, and A7 to A 14 At least one of them represents N, and A 15 ~A 24 At least one of them represents N. According to one embodiment of the present disclosure, one to three of A1 to A6 represent N, and the rest of A1 to A6 represent CR. 10 This represents. According to another embodiment of this disclosure, A7~A 14 1 to 3 of these represent N, and A7 to A 14The rest are CR 10 This represents. According to further embodiments of this disclosure, A 15 ~A 24 Two of them represent N, and A 15 ~A 24 The rest are CR 10 It represents.

[0050] R 10 Each of these independently represents hydrogen or -L2-Ar2; or multiple R 10 If two adjacent R 10 They may be connected to each other to form a ring, and each R 10 R may be the same or different. According to one embodiment of the present disclosure, 10 Each of these independently represents hydrogen or -L2-Ar2, and multiple R 10 If such a thing exists, each R 10 They may be the same or different. For example, R 10 Each of these independently represents hydrogen or -L2-Ar2; or two adjacent R 10 These may be linked together to form a benzofuran ring.

[0051] In equations 2-1 to 2-3, L2, Ar2, d, and e are as defined in equation 2.

[0052] The compound represented by Formula 1 may be at least one selected from the following compounds, but is not limited to these. [ka] [ka]

[0053] The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0054] A combination of at least one compound H1 to H28 and at least one compound C1 to C325 can be used in organic electroluminescent devices.

[0055] According to one embodiment of the present disclosure, the present disclosure may provide a compound represented by formula 1 or a compound represented by formula 2. Specifically, the present disclosure may provide at least one compound from compounds H-1 to H-28 and compounds C-1 to C-325.

[0056] The organic electroluminescent compounds of this disclosure can be represented by the following formula 2-1. [ka]

[0057] In Equation 2-1, X a represents O or S; Ar a and Ar b Each of these independently represents a substituted or unsubstituted (C6-C18) aryl, however, Ar a and b The condition is that at least one of them represents a substituted or unsubstituted naphthyl; R1 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or a combination thereof.

[0058] For example, Ar a and Ar b Each of these may independently be unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, or naphthyl substituted with phenyl, provided that Ar a and Ar b The condition is that at least one of them may be an unsubstituted naphthyl or a phenyl-substituted naphthyl.

[0059] For example, R1 to R6 may each be independently hydrogen, naphthyl, naphthylphenyl, or phenylnaphthyl, provided that at least one of R1 to R6 is naphthyl, naphthylphenyl, or phenylnaphthyl.

[0060] Specifically, the compounds represented by formula 2-1 may include, but are not limited to, the following compounds. [ka]

[0061] The compounds represented by Formula 1 according to this disclosure can be produced by synthesis methods known to those skilled in the art, for example by referring to (Patent Document 1) (published March 2, 2017), but are not limited thereto.

[0062] The compounds represented by Formula 2 of this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, any one of the compounds represented by Formulas 2-1 to 2-3 can be prepared by referring to, but are not limited to, the following reaction schemes 1 to 3: [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka]

[0063] In the reaction scheme, L2, Ar2, d, and e are defined as in Equation 2, and A1~A 24 This is defined in equations 2-1 to 2-3.

[0064] While exemplary synthetic examples of compounds represented by Formula 2 of this disclosure are described above, those skilled in the art will readily understand that all of them are based on reactions such as the Bukwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc., and that the above reactions proceed even when substituents defined in Formula 2 above but not explicitly stated in the specific synthetic examples are attached.

[0065] The organic electroluminescent device according to this disclosure includes a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode.

[0066] One of the first and second electrodes may be an anode and the other may be a cathode. The organic layer may include an emissive layer and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an emissive 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 may be a semi-transparent or reflective electrode and, depending on the material, may be top-emitting, bottom-emitting, or double-emitting. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.

[0067] An organic electroluminescent device according to the present disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a plurality 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 the present disclosure, an organic electroluminescent device according to the present disclosure 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 include a compound represented by formula 1 and a compound represented by formula 2, preferably a plurality of host materials of the present disclosure.

[0068] The light-emitting layer comprises a host and a dopant, where the host comprises a plurality of host materials, the compound represented by formula 1 may be included as a first host compound of the plurality of host materials, and the compound represented by formula 2 may be included as a second host compound of the plurality 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.

[0069] In this specification, the light-emitting layer is a layer that emits light and may be a single layer or a plurality of layers stacked together. The first host material and the second host material may all be contained in a single layer, or the first host material and the second host material may be contained in separate light-emitting layers. According to one embodiment of this disclosure, the doping concentration of the dopant compound to the host compound in the light-emitting layer may be less than 20% by weight.

[0070] The organic electroluminescent devices of this disclosure may further include at least one layer selected from hole injection layers, hole transport layers, hole auxiliary layers, light emission auxiliary layers, electron transport layers, electron injection layers, intermediate layers, electron buffer layers, hole blocking layers, and electron blocking layers. According to one embodiment of this disclosure, the organic electroluminescent devices of this disclosure may further include an amine compound as at least one of the hole injection material, hole transport material, hole auxiliary material, light emission material, light emission auxiliary material, and electron blocking material, in addition to the plurality of host materials of this disclosure. Furthermore, according to one embodiment of this disclosure, the organic electroluminescent devices of this disclosure may further include an azine compound as at least one of the electron transport material, electron injection material, electron buffer material, and hole blocking material, in addition to the plurality of host materials of this disclosure.

[0071] The dopants included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent devices of this disclosure is not particularly limited, but may be selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) metallized complex compounds, more preferably from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) orthometallated complex compounds, and even more preferably from orthometallated iridium complex compounds.

[0072] 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. [Chemical formula]

[0073] In formula 101, L is one of the following structures 1 - 3: [Chemical formula] selected from, where R 100 ~R 103 each independently represents hydrogen, deuterium, halogen, (C1 - C30) alkyl which is unsubstituted or substituted with deuterium and / or halogen, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (C6 - C30) aryl, cyano, substituted or unsubstituted (3 - 30 member) heteroaryl, or substituted or unsubstituted (C1 - C30) alkoxy, or binds to adjacent substituents to form a ring together with pyridine, for example, a substituted or unsubstituted quinoline, isoquinoline, benzofuropyridine, benzothienopyridine, benzothienoquinoline, or indenopyridine ring, R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, (C1 - C30) alkyl which is unsubstituted or substituted with deuterium and / or halogen, substituted or unsubstituted (C3 - C30) cycloalkyl, substituted or unsubstituted (C6 - C30) aryl, substituted or unsubstituted (3 - 30 member) heteroaryl, cyano, or substituted or unsubstituted (C1 - C30) alkoxy, or binds to adjacent substituents to form a ring together with benzene, for example, a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine ring, R 201 ~R 220 each independently represents hydrogen, deuterium, halogen, (C1 - C30) alkyl which is unsubstituted or substituted with deuterium and / or halogen, substituted or unsubstituted (C3 - C30) cycloalkyl, or substituted or unsubstituted (C6 - C30) aryl, or binds to adjacent substituents to form a ring, n represents an integer between 1 and 3.

[0074] Specific examples of dopant compounds are as follows, but are not limited to these. [ka] [ka] [ka] [ka] [ka]

[0075] In the organic electroluminescent device of this disclosure, a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may consist of multiple layers to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, and each of the multiple layers may use two compounds simultaneously. The hole transport layer or electron blocking layer may also consist of multiple layers.

[0076] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may consist of multiple layers to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, in which case each of the multiple layers can use two compounds simultaneously. Similarly, the hole blocking layer or electron transport layer may consist of multiple layers, and each of the multiple layers can use multiple compounds.

[0077] In addition, the organic electroluminescent compounds or host materials described herein may also be used in organic electroluminescent devices that include quantum dots (QDs).

[0078] To form each layer of the organic electroluminescent device of this disclosure, dry deposition methods such as vacuum evaporation, sputtering, plasma, and ion plating can be used, or wet deposition methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used.

[0079] When using a wet film formation method, thin films can be formed by dissolving or diffusing the materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent can be used as long as the materials forming each layer can be dissolved or diffused and there are no problems with film formation.

[0080] The first and second host compounds of this disclosure can generally be filmed by a co-evaporation process or a mixed evaporation process, as described above. Co-evaporation is a mixed evaporation method in which two or more materials are placed in their respective individual crucible sources and an electric current is passed through both cells simultaneously to evaporate the materials. Mixed evaporation is a mixed evaporation method in which two or more materials are mixed in one crucible source before they are evaporated and an electric current is passed through the cell to evaporate the materials. Furthermore, if the first and second host compounds are present in the same or different layers of an organic electroluminescent device, the two host compounds can form films separately. For example, the second host compound may be deposited after the first host compound has been deposited.

[0081] This disclosure can provide a display system by including a compound represented by Formula 2-1, or by using a plurality of host materials comprising a compound represented by Formula 1 and a compound represented by Formula 2. That is, it is possible to manufacture a display system or a lighting system by using the organic electroluminescent compounds or plurality of host materials of this disclosure. Specifically, by using the organic electroluminescent compounds or plurality of host materials of this disclosure, it is possible to manufacture a display system, for example, a display system for a smartphone, tablet, notebook, PC, TV, or automobile; or a lighting system, for example, an outdoor or indoor lighting system.

[0082] The present invention may include the following embodiments: [Aspect 1] A first host material containing a compound represented by the following formula 1, and a second host material containing a compound represented by the following formula 2: [ka] (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 represents -NR5-, -O-, or -S-; L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene; R 31 and R 32 Each of these independently represents a substituted or unsubstituted (3-30 member) heteroaryl; R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R2 to R5 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L3-N(Ar1)(Ar2), or may be linked with adjacent substituents to form a ring; L3 each independently represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3-30 member) heteroarylene; Ar1 and Ar2 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 member) heteroaryl; a and b each independently represent an integer of 1 or 2, c represents an integer of 1 to 3, and here, when a to c are integers of 2 or more, each of R2, each of R3, and each of R4 may be the same or different); HAr-((L2) e -Ar2) d ----- (2) (In formula 2, HAr represents a substituted or unsubstituted (3-20 member) heteroaryl containing a nitrogen atom; L2 each independently represents substituted or unsubstituted (C6-C30) arylene; Ar2 each independently represents substituted or unsubstituted (C6-C30) aryl, or represents the following formula 3 or 4; [ka] Y is O, S, N-*, or NR 21 It represents; R 21 This represents a substituted or unsubstituted (C6-C30) aryl; R 11 ~R 18 Each of these independently represents a position linked to L2, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L4-N(Ar3)(Ar4), or may be linked to an adjacent substituent to form a ring; X 31 ~X 42 Each is independently N or CR a It represents; R aEach of these independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L5-N(Ar5)(Ar6), or may be linked with adjacent substituents to form a ring; L4 and L5 independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar3 to Ar6 each independently represent hydrogen, a substituted or unsubstituted (C1 to C30) alkyl group, a substituted or unsubstituted (C2 to C30) alkenyl group, a substituted or unsubstituted fused ring group of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, a substituted or unsubstituted (C6 to C30) aryl group, or a substituted or unsubstituted (3 to 30-membered) heteroaryl group; d represents an integer between 1 and 3, and if d is an integer greater than or equal to 2, then ((L2) e Each of the elements in -Ar2) may be the same or different; e represents an integer between 0 and 2, and if e is an integer of 2, then each of L2 may be the same or different; (* indicates the connection point to L2) Multiple host materials, including [Aspect 2] The substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted heteroaryl containing a nitrogen atom, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituents of the substituted condensed ring group of an aliphatic ring and an aromatic ring are, each independently, deuterium; halogen; cyano; carboxyl; nitro; hydro Xyl; phosphine oxide; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 member) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or (C6-C30) substituted (3-30 member) heteroaryl; unsubstituted or (C1-C30)(C6-C30) aryls substituted with at least one alkyl or (3-30 member) heteroaryl; tri(C1-C30) alkylsilyl; tri(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; condensed ring group of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C2-C30) alkenylamino; (C1-C30) alkyl(C2-C30) alkenylamino; mono- or di-(C6-C30) arylamino; (C1-C30) alkyl(C6-C30) arylamino; mono- or di-(3-30 member) heteroarylamino; (C1-C A plurality of host materials according to Embodiment 1, wherein at least one is selected from the group consisting of 30) alkyl (3-30 member) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-30 member) heteroarylamino; (C6-C30) aryl (3-30 member) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphine; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl. [Aspect 3] The above equation 1 is given by the following equations 1-1 and 1-2: [ka] (In the formula, X1, Y1, L1, R 31 , R 32 (R1-R4 and a-c are as defined in Embodiment 1) A plurality of host materials according to embodiment 1, represented by at least one of the following. [Aspect 4] The above equation 2 is given by the following equations 2-1 to 2-3: [ka] (In the formula, A1~A 24 Each of them operates independently, CR 10 Or it represents N, and at least one of A1 to A6 represents N, and A7 to A 14 At least one of them represents N, and A 15 ~A 24 At least one of them represents N; R 10 Each of these independently represents hydrogen or -L2-Ar2, and multiple R 10 If such a thing exists, each R 10 They may be the same or different; L2, Ar2, d, and e are as defined in Embodiment 1. A plurality of host materials according to embodiment 1, represented by at least one of the following. [Aspect 5] R 31 and R 32 The plurality of host materials according to Embodiment 1, wherein each is independently a substituted or unsubstituted dibenzofuranil, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzoflopyridyl, a substituted or unsubstituted benzonaphthofuranil, or a substituted or unsubstituted benzonaphthothiophenyl. [Aspect 6] The compound represented by formula 1 is the following compound: [ka] [ka] A plurality of host materials according to embodiment 1, which are at least one selected from the above. [Aspect 7] The compound represented by formula 2 is the following compound: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] A plurality of host materials according to embodiment 1, which are at least one selected from the above. [Aspect 8] 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 as described in Embodiment 1. [Aspect 9] Equation 2-1 below: [ka] (In the formula, X a represents O or S; Ar a and Ar b Each of these independently represents a substituted or unsubstituted (C6-C18) aryl, however, Ar a and Ar b The condition is that at least one of them represents a substituted or unsubstituted naphthyl; R1 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or a combination thereof. An organic electroluminescent compound represented by [the specified formula]. [Aspect 10] The compound represented by formula 2-1 is the following compound: [ka] An organic electroluminescent compound according to embodiment 9, selected from the above. [Aspect 11] An organic electroluminescent device comprising the organic electroluminescent compound described in Embodiment 9. [Aspect 12] The organic electroluminescent device according to embodiment 11, wherein the organic electroluminescent compound is contained in the light-emitting layer. This specification will describe in detail, with reference to representative compounds of this disclosure, the methods for preparing compounds according to this disclosure and their properties. However, this disclosure is not limited to the following examples. [Examples]

[0083] Example 1: Preparation of compound C-295 [ka] Synthesis of compound 1-1 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'-bi(1,3,2-dioxaborolane) (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%).

[0084] Synthesis of Compounds 1-2 In a flask, compound 1-1 (9 g, 27.4 mmol), 2-chloro-4(naphthalene-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%).

[0085] Synthesis of compound C-295 In a flask, compounds 1-2 (5 g, 10.3 mmol), (naphthalene-2-yl)-boronic 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%).

[0086] [Table 1]

[0087] Example 2: Preparation of compound C-304 [ka] In a flask, compounds 1-2 (5 g, 10.3 mmol), (naphthalene-2-yl)-boronic 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%).

[0088] [Table 2]

[0089] Example 3: Preparation of compound C-296 [ka] Synthesis of Compound 3-1 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'-bi(1,3,2-dioxaborolane) (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%).

[0090] Synthesis of compound 3-2 In a flask, compound 3-1 (9.2 g, 28 mmol), 2-chloro-4(naphthalene-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%).

[0091] Synthesis of compound C-296 In a flask, compound 3-2 (5 g, 10.3 mmol), (naphthalene-2-yl)-boronic 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%).

[0092] [Table 3]

[0093] Example 4: Preparation of compound C-325 [ka] Synthesis of Compound 4-1 In a flask, (1-chlorodibenzo[b,d]furan-2-yl)boronic acid (10 g, 20.6 mmol), 2-chloro-4(naphthalene-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 of toluene, 100 mL of ethanol, and 100 mL of 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%).

[0094] Synthesis of compound C-325 In a flask, compound 4-1 (7 g, 14.48 mmol), (naphthalene-2-yl)-boronic 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%).

[0095] [Table 4]

[0096] Example 5: Preparation of compound C-312 [ka] In a flask, compound 4-1 (4.2 g, 8.69 mmol), compound 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%).

[0097] [Table 5]

[0098] The following describes in detail the method for producing an organic electroluminescent device (OLED) containing an organic electroluminescent compound or multiple host materials, and its properties, with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0099] Device Examples 1-6: Manufacturing of a deposited red OLED using multiple host materials according to the present disclosure as the host material. An OLED was manufactured 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 OLEDs was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 3 was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 shown in Table 3 was introduced into another cell of the vacuum deposition apparatus. The two materials were evaporated at different rates, and compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing an electric current through the cell, 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, an emissive layer was formed thereon as follows. The first and second host compounds shown in Table 1 below were introduced as hosts into two cells of the vacuum deposition apparatus, and compound D-39 was introduced as a dopant into another cell. The two host materials were evaporated in a 1:1 ratio, and the dopant materials were evaporated simultaneously in different ratios. The dopant was deposited at a doping amount of 3 wt% based on the total amount of host and dopant, thereby forming an emissive layer with a thickness of 40 nm on the second hole transport layer. Compounds ET-1 and EI-1 were evaporated in a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the emissive layer. After depositing compound EI-1 as a 2nm thick electron injection layer on the electron transport layer, an 80nm thick Al cathode was deposited on the electron injection layer using another vacuum deposition apparatus. In this way, an OLED was fabricated. All materials used to manufacture the OLED were 10 -6 It was purified by vacuum sublimation using a Thor's IV line.

[0100] Comparative Examples 1-5: Production of OLEDs containing comparative compounds as hosts The OLED was manufactured in the same manner as in Device Example 1, except that the host compound shown in Table 1 below was used as the single host for the light-emitting layer.

[0101] Table 1 below shows the driving voltage, luminous efficiency, and luminous color at a brightness of 1,000 nits, as well as the time required for the brightness to decrease from 100% to 95% (lifetime; T95) at a brightness of 5,000 nits, for the OLEDs manufactured in Device Examples 1-6 and Comparative Examples 1-5.

[0102] [Table 6]

[0103] Table 1 above shows that OLEDs comprising multiple host materials, including specific combinations of compounds according to this disclosure, exhibit superior drive voltage, luminous efficiency, and / or lifetime characteristics. These results represent a significant improvement compared to OLEDs using the first and second hosts individually.

[0104] Comparative Example 6: Production of an OLED containing a comparative compound as a host An OLED was manufactured in the same manner as in Device Example 1, except that the host compound shown in Table 2 below was used alone as the host for the light-emitting layer.

[0105] Device Examples 7-9: Manufacturing of deposited red OLEDs using multiple host materials according to the present disclosure as hosts. The OLED was manufactured using the same method as in Comparative Example 6, except that the host compounds shown in Table 2 below were used alone as the host for the light-emitting layer.

[0106] Table 2 below shows the driving voltage, power efficiency, and luminescence color of the OLEDs manufactured in Comparative Example 6 and Device Examples 7-9 at a brightness of 1,000 nits.

[0107] [Table 7]

[0108] Table 2 above shows that the OLED containing the compound according to this disclosure has superior driving voltage and power efficiency characteristics compared to the OLED containing the comparative compound.

[0109] The compounds used in the device examples and comparative examples are shown in Table 3 below.

[0110] [Table 8]

[0111] [Table 9]

Claims

1. Multiple host materials used in the light-emitting layer constituting an organic electroluminescent device, The following equation 1: 【Chemistry 1】 (In Equation 1, X １ and Y １ These are independently -N= and -NR ５ It represents -, -O-, or -S-, however, X １ and Y １ One of them represents -N= and X １ and Y １ The other is -NR ５ The condition is that it represents -, -O-, or -S-; L １ represents a single bond, or a substituted or unsubstituted (C6-C30) arylene; R ３１ and R ３２ Each of these independently represents a substituted or unsubstituted (3-30 member) heteroaryl; R １ represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R ２ ~R ５ Each is independently a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L ３ -N(Ar １ ) (Ar ２ ) may represent, or may be linked with adjacent substituents to form a ring; L ３ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar １ and Ar ２ Each 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 a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-30 membered) heteroaryl group; a and b each independently represent integers of 1 or 2, and c represents an integer between 1 and 3. If a to c are integers of 2 or greater, then R ２ Each of the following, R ３ Each of the above, and R ４ Each of these may be the same or different. A first host material containing a compound represented by, Equation 2 below: HAr-((L ２ ) ｅ -Ar ２ ) ｄ ----- (2) (In Equation 2, HAr represents a substituted or unsubstituted (3-20 member) heteroaryl compound containing a nitrogen atom; L ２ Each of these independently represents a substituted or unsubstituted (C6-C30) arylene; Ar ２ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl, or the following formula 3 or 4: 【Chemistry 2】 It represents; Y is O, S, N-*, or NR ２１ It represents; R ２１ This represents a substituted or unsubstituted (C6-C30) aryl; R １１ ~R １８ Each is independent of L ２ This indicates a position where it is linked, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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 group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or -L ４ -N(Ar ３ ) (Ar ４ ) represents; X ３１ ~X ４２ Each is independently N or CR ａ It represents; R ａ Each is independently a hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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, a substituted or unsubstituted fused ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -L ５ -N(Ar ５ ) (Ar ６ ) may represent, or may be linked with adjacent substituents to form a ring; L ４ and L ５ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar ３ ~Ar ６ Each 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 a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-30 membered) heteroaryl group; d represents an integer from 1 to 3, and if d is an integer of 2 or more, ((L ２ ) ｅ -Ar ２ Each of these may be the same or different; e represents an integer from 0 to 2, and when e is an integer of 2, L ２ Each of them may be the same or different; * is L ２ (Represents the connection point to) Multiple host materials, including a second host material containing a compound represented by .

2. The substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted heteroaryl containing a nitrogen atom, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and the substituents of the substituted condensed ring group of an aliphatic ring and an aromatic ring are, each independently, deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C 30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 member) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or (C6-C30) substituted (3-30 member) heteroaryl; unsubstituted or at least one of (C1-C30) alkyl and (3-30 member) heteroaryl Substituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; fused ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C2-C30) alkenylamino; (C1-C30) alkyl(C2-C30) alkenylamino; mono- or di-(C6-C30) aryl Mino; (C1-C30) alkyl(C6-C30) arylamino; mono- or di-(3-30 member) heteroarylamino; (C1-C30) alkyl(3-30 member) heteroarylamino; (C2-C30) alkenyl(C6-C30) arylamino; (C2-C30) alkenyl(3-30 member) heteroarylamino; (C6-C30) aryl(3-30 member) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphine;A plurality of host materials according to claim 1, which are at least one selected from the group consisting of di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The above formula 1 is the following formulas 1-1 and 1-2: 【Transformation 3】 (In the formula, X １ , Y １ , L １ , R ３１ , R ３２ , R １ ~R ４ , and a to c are as defined in claim 1.) A plurality of host materials according to claim 1, represented by at least one of the following.

4. The above equation 2 is expressed as follows: Equations 2-1 to 2-3: 【Chemistry 4】 (In the formula, A １ ~A ２４ Each of them operates independently, CR １０ Or it represents N, A １ ~A ６ At least one of them represents N, and A ７ ~A １４ At least one of them represents N, and A １５ ~A ２４ At least one of them represents N; R １０ Each is independently of hydrogen or -L ２ -Ar ２ Represents multiple R １０ If there exists, each R １０ They may be the same or different; L ２ Ar ２ ( d, and e are as defined in claim 1) A plurality of host materials according to claim 1, represented by at least one of the following.

5. R ３１ and R ３２ The plurality of host materials according to claim 1, wherein each is independently a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzophropyridyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

6. The compound represented by formula 1 is the following compound: 【Transformation 5】 【Transformation 6】 A plurality of host materials according to claim 1, wherein at least one is selected from the following.

7. The compound represented by formula 2 is the following compound: 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 A plurality of host materials according to claim 1, wherein at least one is selected from the following.

8. 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 as described in claim 1.

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