Multiple host materials and organic electroluminescent device comprising same

Abstract

A plurality of host materials and an organic electroluminescent device comprising the same. The present disclosure provides a plurality of host materials comprising a first host material comprising a compound represented by the following Formula 1 and a second host material comprising a compound represented by any one of the following Formulae 2-1 and 2-2: # imgabs0 #

Description

[0001] This divisional patent application is a divisional application of the patent application with international application number PCT / KR2019 / 005686, national application number 201980041619.8, filing date May 13, 2019, and title "Multiple host materials and organic electroluminescent devices comprising the same". Technical Field

[0002] The present disclosure relates to multiple host materials and an organic electroluminescent device comprising the same. Background Art

[0003] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) of a TPD / Alq3 bilayer composed of a light emitting layer and a charge transport layer. Since then, research on OLEDs has been rapidly carried out and it has been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. In addition, long-term use and high resolution of displays require OLEDs with high luminous efficiency and / or long lifespan.

[0004] Korean Patent Application Publication No. 2017-0022865 discloses a benzoxazole derivative compound for improving the performance of OLEDs. However, there is still a need to develop materials for improving the performance of OLEDs. Summary of the Invention

[0005] Technical Problem

[0006] An object of the present disclosure is to provide multiple host materials comprising a specific compound combination, suitable for producing organic electroluminescent devices having higher luminous efficiency and / or longer lifespan characteristics.

[0007] Solution to the Problem

[0008] The inventors of the present invention have found that the above object can be achieved by multiple host materials comprising 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:

[0009]

[0010] Wherein,

[0011] Ar represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur;

[0012] L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0013] Each of X1 to X8 independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or adjacent ones of X1 to X8 may be connected to each other to form one or more rings; provided that at least one pair of X1 and X2, X2 and X3, X3 and X4, X4 and X5, X5 and X6, X6 and X7, and X7 and X8 may be connected to each other to form one or more rings, wherein the ring has 1 to 5 single rings;

[0014] Each of R5 to R9 independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl; or adjacent ones of R5 to R9 may be connected to each other to form one or more rings; and

[0015]

[0016] wherein

[0017] X represents -N=, -NR 10 -, -O-, or -S-;

[0018] Y represents -N=, -NR 11 -, -O-, or -S-, provided that when X represents -N=, Y represents -NR 11 -, -O-, or -S-, and when X represents -NR 10 -, Y represents -N=, -O-, or -S-;

[0019] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing one or more nitrogen atoms;

[0020] L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

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

[0022] Each of R2 to R4 independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent ones of R2 to R4 may be connected to each other to form one or more rings;

[0023] R 10 and R 11 Each independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;

[0024] a' represents the integer 1; b' and c' each independently represent the integer 1 or 2; d' represents an integer from 1 to 4; provided that if b', c', and d' are each independently an integer of 2 or greater, then each of R2 to R4 may be the same or different.

[0025] Advantageous effects of the invention

[0026] By including a specific combination of the compounds of the present disclosure as a host material, an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics compared to conventional organic electroluminescent devices can be provided, and a display system or an illumination system using the organic electroluminescent device can be manufactured. Detailed Description

[0027] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0028] In the present disclosure, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a luminescence assisting material, an electron blocking material, a luminescent 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.

[0029] In the present disclosure, the term "multiple organic electroluminescent materials" means an organic electroluminescent material that is a combination of at least two compounds and can be included in any layer constituting the organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the multiple organic electroluminescent materials can be a combination of at least two compounds, and the at least two compounds can be included in at least one of a hole injection layer, a hole transport layer, a hole assisting layer, a luminescence assisting layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds can be included in the same layer or different layers by methods used in the art (e.g., they can be co-evaporated or co-evaporated separately, or can be evaporated separately).

[0030] In the present disclosure, the term "multiple host materials" means an organic electroluminescent material that is a combination of at least two host materials. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present disclosure can be included in any luminescent layer constituting the organic electroluminescent device. At least two compounds included in the multiple host materials can be included in one luminescent layer simultaneously, or can be included in different luminescent layers separately. If at least two host materials are included in one layer, for example, they can be co-evaporated to form a layer, or can be co-evaporated separately simultaneously to form a layer.

[0031] As used herein, the term “(C1-C30)alkyl” means a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms forming the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. As used herein, the term “(C3-C30)cycloalkyl” means a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7-membered)heterocycloalkyl” means such a cycloalkyl group that has 3 to 7 ring skeleton atoms and includes 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 above heterocycloalkyl groups may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term “(C6-C30)aryl” or “(C6-C30)arylene” means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15. The above aryl or arylene groups may be partially saturated and may contain a spiro structure. The above aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, groups such as a naphthacenyl group, a fluoranthenyl group, a spirobifluorene group, and a spiro[fluorene-benzo[b]fluorene] group. The term “(3- to 50-membered) heteroaryl” or “(3- to 30-membered) heteroarylene” refers to an aryl group having 3 to 50, or 3 to 30, ring backbone atoms, wherein the number of ring backbone carbon atoms is preferably 3 to 30, more preferably 5 to 20, and includes at least one (preferably 1 to 4) heteroatom selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl or heteroarylene may be monocyclic or a fused ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl or heteroarylene formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may contain a spiro structure. The above heteroaryl may include monocyclic heteroaryl groups such as a furyl group, a thienyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a thiadiazolyl group, an isothiazolyl group, an isoxazolyl group, an oxazolyl group, an oxadiazolyl group, a triazinyl group, a tetrazinyl group, a triazolyl group, a tetrazolyl group, a furazanyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, etc.; and fused ring heteroaryl groups such as a benzofuryl group, a benzothienyl group, an isobenzofuryl group, a dibenzofuryl group, a benzonaphthofuryl group, a dibenzothienyl group, a benzonaphthothienyl group, a benzimidazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoisoxazolyl group, a benzoxazolyl group, an isoindolyl group, an indolyl group, an indazolyl group, a benzothiadiazolyl group, a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a carbazolyl group, a benzocarbazolyl group, a phenoxazinyl group, a phenanthridinyl group, a phenanthro[4,5-d]oxazolyl group, a benzodioxolyl group, etc. Further, “halogen” includes F, Cl, Br, and I.

[0032] Herein, in the expression “substituted or unsubstituted”, “substituted” means that a hydrogen atom in certain functional groups is replaced by another atom or another functional group (i.e., a substituent). In Ar, L1, HAr, L2, X1 to X8, X 11 to X 33 and R1 to R 15The substituents of the substituted alkyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, or substituted alkylarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or substituted by at least one of (C1-C30)alkyl, (C6-C30)aryl, and di(C6-C30)arylamino (3- to 50-membered)heteroaryl; unsubstituted or substituted by at least one of cyano, (C1-C30)alkyl, (3- to 50-membered)heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)arylsilyl (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, these substituents are each independently at least one selected from the group consisting of: (C1-C20)alkyl; unsubstituted or substituted by at least one of one or more (C1-C20)alkyl, one or more (3- to 30-membered)heteroaryl, and one or more di(C6-C25)arylamino (C6-C25)aryl; unsubstituted or substituted by at least one of one or more (C1-C20)alkyl and one or more di(C6-C25)aryl (3- to 30-membered)heteroaryl; and di(C6-C20)arylamino.According to another embodiment of the present disclosure, each of these substituents is independently at least one selected from the group consisting of: (C1-C10) alkyl; (C6-C20) aryl unsubstituted or substituted with at least one of one or more (C1-C10) alkyls and one or more bis(C6-C18)arylaminos; (5- to 25-membered) heteroaryl unsubstituted or substituted with one or more (C6-C18) aryls; and bis(C6-C18)arylamino. For example, each of these substituents is independently at least one of methyl; tert-butyl; phenyl unsubstituted or substituted with at least one of pyridyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl, dibenzothiophenyl, and diphenylamino; naphthyl unsubstituted or substituted with at least one diphenyltriazinyl; biphenyl; naphthylphenyl; terphenyl; dimethylfluorenyl; phenylfluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; phenanthryl; benzophenanthryl; pyridyl; triazinyl substituted with at least one of phenyl and naphthyl; indolyl substituted with at least one phenyl; benzimidazolyl substituted with at least one phenyl; quinolinyl; quinazolinyl substituted with at least one of phenyl and biphenyl; quinoxalinyl substituted with at least one phenyl; carbazolyl unsubstituted or substituted with at least one phenyl; dibenzofuranyl; dibenzothiophenyl; benzonaphthothiophenyl; benzocarbazolyl unsubstituted or substituted with at least one phenyl; dibenzocarbazolyl; benzophenanthrothiophenyl; diphenylamino; dimethylfluorenylphenylamino; and substituted or unsubstituted (16- to 33-membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur.

[0033] In the formulae of the present disclosure, "adjacents may be connected to each other to form one or more rings" means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted mono- or polycyclic (3- to 30-membered), preferably (3- to 26-membered) alicyclic or aromatic ring, or a combination thereof. Additionally, 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.

[0034] Herein, a heteroaryl, heteroarylene, or heterocycloalkyl may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Additionally, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(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 tris(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.

[0035] In Formula 1, Ar represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur. According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl containing at least one of nitrogen, oxygen, and sulfur. According to another embodiment of the present disclosure, Ar represents an unsubstituted or (C1-C30)alkyl-substituted (C6-C18) aryl, or an unsubstituted or (C6-C18)aryl-substituted (5- to 20-membered) heteroaryl containing nitrogen, oxygen, and sulfur. Specifically, Ar represents a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophenyl. For example, Ar may represent phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, benzophenanthryl, dibenzofuranyl, dibenzothiophenyl, an unsubstituted or phenyl-substituted carbazolyl, or benzonaphthofuranyl.

[0036] In Formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L1 represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene. According to another embodiment of the present disclosure, L1 represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 20-membered) heteroarylene. Specifically, L1 may represent a single bond, a phenylene, a naphthylene, a biphenylene, or a phenanthroxazolylene.

[0037] In Formula 1, X1 to X8 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or adjacent ones of X1 to X8 may be connected to each other to form one or more rings; provided that at least one pair of X1 and X2, X2 and X3, X3 and X4, X4 and X5, X5 and X6, X6 and X7, and X7 and X8 may be connected to each other to form one or more rings, wherein the ring has 1 to 5 monocycles. According to one embodiment of the present disclosure, X1 to X8 each independently represent hydrogen; or at least one pair of X1 and X2, X2 and X3, X3 and X4, X4 and X5, X5 and X6, X6 and X7, and X7 and X8 may be connected to each other to form one or more rings, wherein the ring has 1 to 5 monocycles, preferably 2 to 5 monocycles. For example, X1 and X2 are connected to each other to form an indole ring, wherein the ring has 2 monocycles. The ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) aliphatic or aromatic ring, or a combination thereof; preferably a substituted or unsubstituted mono- or polycyclic (3- to 20-membered) aliphatic or aromatic ring, or a combination thereof; and more preferably a substituted or unsubstituted monocyclic (3- to 8-membered) aromatic ring. Specifically, the ring may be a ring in which 1 to 5 monocycles, preferably 2 to 5 monocycles are fused. Additionally, the 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; and more preferably at least one heteroatom selected from N and S. When X1 to X8 may be connected to adjacent substituents to form a ring, the compound represented by Formula 1 may be a fused carbazole-based compound, a fused azulene-based compound, etc. For example, X1 to X8 each independently represent hydrogen; or may be connected to one or more adjacent substituents to form a benzene ring, an indole ring substituted with one or more phenyl groups and / or one or more biphenyl groups, a benzothiophene ring, a benzoindole ring substituted with at least one of one or more phenyl groups and one or more naphthyl groups, a 15-membered polycycle, a nitrogen-containing 18-membered polycycle, or a nitrogen-containing 22-membered polycycle.

[0038] R5 to R9 each independently represent hydrogen, deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; or adjacent ones of R5 to R9 may be connected to each other to form one or more rings.

[0039] According to one embodiment of the present disclosure, Formula 1 may be represented by any one of Formulas 1-1 to 1-10 below.

[0040]

[0041]

[0042] In Formulas 1-1 to 1-10, the definitions of the substituents are as follows.

[0043] Ar and L1 are as defined in Formula 1.

[0044] V and W each independently represent CR 12 R 13 、NR 14 、O, or S. According to one embodiment of the present disclosure, V and W each independently represent NR 14 、O, or S. For example, V may represent NR 14 or S, and W may represent S.

[0045] R 12 to R 14 、X 11 to X 23 、and X 31 to X 33 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group.

[0046] According to one embodiment of the present disclosure, R 12 to R 14 each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 12 to R 14 each independently represents an unsubstituted (C6-C18) aryl group. For example, R 12 to R 14 may each independently represent a phenyl group or a biphenyl group.

[0047] According to one embodiment of the present disclosure, X 11 to X 23 , and X 31 to X 33 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, X 11 to X 23 , and X 31 to X 33 each independently represents hydrogen, deuterium, or an unsubstituted (C6-C18) aryl group. For example, X 11 to X 23 , and X 31 to X 33 may each independently represent hydrogen or a phenyl group.

[0048] X 24 to X 30 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or adjacent ones of X 24 to X 30 may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, X24 to X 30 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group; or X 24 to X 30 adjacent ones among them may be connected to each other to form one or more rings. According to another embodiment of the present disclosure, X 24 to X 30 each independently represents hydrogen, deuterium, or an unsubstituted (C6-C18) aryl group; or X 24 to X 30 adjacent ones among them may be connected to each other to form one or more rings. For example, X 24 to X 30 each independently represents hydrogen; or X 24 to X 30 adjacent ones among them may be connected to each other to form a benzene ring.

[0049] a, e to i, k, l, o, p, s, u, y, and z each independently represent an integer from 1 to 4; b to d, j, and m each independently represent an integer from 1 to 6; n and r each independently represent an integer from 1 to 3; q represents the integer 1 or 2; t represents an integer from 1 to 5; in the case where a to u, y, and z are each independently an integer of 2 or greater, X 11 to X 33 each of them may be the same or different.

[0050] In Formula 2, X represents -N=, -NR 10 -, -O-, or -S-; Y represents -N=, -NR 11 -, -O-, or -S-; provided that when X represents -N=, then Y represents -NR 11 -, -O-, or -S-, and when X represents -NR 10 -, then Y represents -N=, -O-, or -S-. According to one embodiment of the present disclosure, X represents -N=, -NR 10 -, -O-, or -S-; Y represents -N=, -NR 11 -, -O-, or -S-; provided that either X or Y represents -N=.

[0051] R 10 and R 11each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group. According to one embodiment of the present disclosure, R 10 and R 11 each independently represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 10 and R 11 each independently represents an unsubstituted (C6-C18) aryl group. For example, R 10 and R 11 may be phenyl.

[0052] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing one or more nitrogen atoms. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5- to 25-membered) heteroaryl containing one or more nitrogen atoms. According to another embodiment of the present disclosure, HAr represents a (5- to 20-membered) heteroaryl containing one or more nitrogen atoms, which is unsubstituted or substituted by one or more (5- to 25-membered) heteroaryls and / or one or more (C6-C25) aryls. Specifically, HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl. For example, HAr may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted quinoxalinyl, a substituted quinazolinyl, or a substituted naphthyridinyl. The substituents of these substituted triazinyls, substituted pyrimidyls, substituted quinoxalinyls, substituted quinazolyls, and substituted naphthyridinyls may be unsubstituted or phenyl, naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothienyl, dibenzofuranyl, benzonaphthothienyl, phenylcarbazolyl, and phenylbenzocarbazolyl which are substituted by one or more diphenylamino groups.

[0053] In Formula 2, L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L2 represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene. According to another embodiment of the present disclosure, L2 represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 20-membered) heteroarylene. For example, L2 may represent a single bond, a phenylene, or a pyridylene.

[0054] In Formula 2, 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 the present disclosure, R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R1 represents an unsubstituted (C6-C29) aryl group substituted with one or more (C1-C10) alkyl groups and / or one or more (C6-C18) aryl groups; or a (5- to 25-membered) heteroaryl group unsubstituted or substituted with one or more (C6-C18) aryl groups. For example, R1 can be phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, phenylcarbazolyl, phenylbenzocarbazolyl, dibenzofuranyl, or dibenzothiophenyl.

[0055] In Formula 2, each of R2 to R4 independently represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or adjacent ones of R2 to R4 can be connected to each other to form one or more rings. For example, R2 to R4 can be hydrogen.

[0056] In Formula 2, a' represents the integer 1; b' and c' each independently represent the integer 1 or 2; d' represents an integer from 1 to 4; provided that if each of b', c', and d' is an integer of 2 or greater, then each of R2 to R4 can be the same or different.

[0057] According to one embodiment of the present disclosure, Formula 2 can be represented by any one of the following Formulas 2-1 and 2-2.

[0058]

[0059] In Formulas 2-1 and 2-2, X, Y, R1 to R4, L2, and a' to d' are as defined in Formula 2.

[0060] In Formulas 2-1 and 2-2, Y1 to Y5, and Y11 to Y 17 each independently represents N or CR 15 According to one embodiment of the present disclosure, at least one of Y1 to Y5 represents CR 15 , and Y 11 to Y 17 at least one of which represents CR 15 .

[0061] R 15 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or adjacent ones of R 15 may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, R 15 each independently represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 15 each independently represents hydrogen; deuterium; an unsubstituted or (C1-C10)alkyl- and / or one or more bis(C6-C18)arylamino-substituted (C6-C18) aryl group; or an unsubstituted or (C6-C18)aryl-substituted (5- to 20-membered) heteroaryl group. For example, R 15 may each independently represent hydrogen, an unsubstituted or diphenylamino-substituted phenyl group, a naphthyl group, a biphenyl group, a dimethylfluorenyl group, a dimethylbenzofluorenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a benzonaphthothiophenyl group, a phenylcarbazolyl group, or a phenylbenzocarbazolyl group.

[0062] The compounds represented by Formula 1 include the following compounds, but are not limited thereto.

[0063]

[0064]

[0065]

[0066]

[0067]

[0068] The compounds represented by Formula 2 include, but are not limited to, the following compounds.

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] A combination of at least one of Compounds C1-1 to C1-94 and at least one of Compounds C2-1 to C2-125 can be used in an organic electroluminescent device.

[0076] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to the following Reaction Scheme 1 and the following: Korean Patent Application Publication No. 2015-0135109A (published on December 2, 2015), 2015-0032447A (published on March 26, 2015), 2016-0099471A (published on August 22, 2016), 2018-0012709A (published on February 6, 2018), 2012-0132815A (published on December 10, 2012), 2015-0077513A (published on July 8, 2015), and 2017-0129599A (published on November 27, 2017), and Korean Patent No. 1478990B (published on December 29, 2014), but not limited thereto.

[0077] [Reaction Scheme 1]

[0078]

[0079] In Reaction Scheme 1, Ar, L1, X 28 to X 30 , r, s, and t are defined as in Formula 1-9 above.

[0080] The compound represented by Formula 2 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 2 can be prepared by referring to Korean Patent Application Publication No. 2017-0022865A (published on March 2, 2017), but is not limited thereto.

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

[0082] The light-emitting layer includes a host and a dopant. The host includes a plurality of host materials. The compound represented by Formula 1 may be included as a first host compound among the plurality of host materials, and the compound represented by Formula 2 may be included as a second host compound among the plurality of host materials. The weight ratio of the first host compound to the second host compound is in the range of 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 60:40, and still more preferably about 50:50.

[0083] The light-emitting layer is a layer from which light is emitted and may be a single layer or a multi-layer in which two or more layers are stacked. Among the plurality of host materials according to the present disclosure, the first and second host materials may be included in one layer simultaneously or may be included in different light-emitting layers separately. According to an embodiment of the present disclosure, the doping concentration of the dopant compound is less than 20 wt% relative to the host compound in the light-emitting layer.

[0084] The organic electroluminescent device of the present disclosure may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary 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 the present disclosure, the organic electroluminescent device may further include an amine-based compound other than the various host materials of the present disclosure as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the luminescent material, the luminescent auxiliary material, and the electron blocking material. In addition, according to one embodiment of the present disclosure, the organic electroluminescent device may further include an azine-based compound other than the various host materials of the present disclosure as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material.

[0085] The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material is not particularly limited, but may be preferably selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallized iridium complex compounds.

[0086] The dopant compound included in the organic electroluminescent device of the present disclosure may include the following:

[0087] The compound represented by Formula 101 is not limited thereto.

[0088]

[0089] In Formula 101, L is selected from the following structures 1 and 2:

[0090]

[0091] R 100 To R 103 Each independently represents 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 may be connected to an adjacent R 100 To R 103Together with pyridine, form one or more rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indolopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indoloquinoline ring;

[0092] R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, (C1-C30) alkyl which is unsubstituted or substituted with deuterium and / or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to adjacent R 104 to R 107 and together with benzene form one or more rings, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indolopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine ring;

[0093] R 201 to R 211 Each independently represents hydrogen, deuterium, halogen, (C1-C30) alkyl which is unsubstituted or substituted with deuterium and / or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be linked to adjacent R 201 to R 211 to form a ring; and

[0094] n’ represents an integer from 1 to 3.

[0095] Specific examples of the dopant compounds are as follows, but are not limited thereto.

[0096]

[0097]

[0098]

[0099]

[0100] To form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used.

[0101] When a solvent is used in the wet film formation method, a thin film can be formed by dissolving or diffusing the materials for forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the materials for forming each layer can be dissolved or diffused and which has no problem in terms of film forming ability.

[0102] In addition, the compound represented by Formula 1 and the compound represented by Formula 2 can be used for film formation in the methods listed above, typically by co-evaporation method or mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to two chambers simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chamber to evaporate the materials.

[0103] The present disclosure can provide a display system by including a plurality of host materials. In addition, it is possible to produce a display system or a lighting system by using the organic electroluminescent device of the present disclosure. Specifically, it is possible to produce a display system, such as a display system for a smartphone, a tablet computer, a notebook, a PC, a TV, or an automobile, or a lighting system, such as an outdoor or indoor lighting system, by using various host materials of the present disclosure.

[0104] Hereinafter, the luminous efficiency and lifetime characteristics of the OLED according to the present disclosure will be explained. However, the following examples only illustrate in detail the characteristics of the OLED according to the present disclosure, but the present disclosure is not limited to the following examples.

[0105] Device Examples 1, 2, and 5 to 12: Manufacturing an OLED by co-evaporating a first and a second host compound according to the present disclosure

[0106] The OLED according to the present disclosure is produced as follows: The indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on the glass substrate used for the OLED is subjected to ultrasonic washing successively with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. The ITO substrate is mounted on the substrate holder of the vacuum vapor deposition equipment. The compound HI-1 is introduced into the chamber of the vacuum vapor deposition equipment, and then the pressure in the equipment chamber is then controlled to 10 -6Next, an electric current is applied to the chamber to evaporate the materials introduced above, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Then, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus and evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus and 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 these hole injection layers and hole transport layers, a light-emitting layer is formed thereon as follows: The first host compound and the second host compound shown in Table 1 are introduced into two chambers of the vacuum vapor deposition apparatus as hosts respectively, and compound D-39 is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, and the dopant material is simultaneously evaporated at a different rate to deposit at a doping amount of 3 wt% based on the total amount of the host and the dopant, so as to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Then, compound ET-1 and compound EI-1 are evaporated at a rate of 1:1 in two other chambers to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 on the electron transport layer as an electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer through another vacuum vapor deposition apparatus. Thus, an OLED is produced.

[0107] Device Example 3: Manufacturing an OLED by co-evaporating a first and a second host compound according to the present disclosure

[0108] An OLED is produced in the same manner as in Device Example 2, except that the first host compound and the second host compound described in Table 1 are deposited in one chamber of the vacuum deposition apparatus instead of in two chambers.

[0109] Device Example 4: Manufacturing an OLED by co-evaporating a first and a second host compound according to the present disclosure

[0110] An OLED is produced in the same manner as in Device Example 2, except that compound D-78 is used as the dopant instead of compound D-39.

[0111] Comparative Examples 1 and 2: Manufacturing an OLED not according to the present disclosure

[0112] An OLED is produced in the same manner as in Device Example 1, except that only the second host compound described in Table 1 below is used instead of the two hosts.

[0113] The results of the luminous efficiency of the OLEDs produced in the device examples and the comparative examples at a brightness of 5,000 nits and the time (T97) taken to reduce 100% of the initial brightness to 97% of the brightness at a constant current and at a brightness of 5,000 nits are shown in Table 1 below.

[0114] [Table 1]

[0115]

[0116] It can be confirmed from Table 1 that the organic electroluminescent device containing a specific compound combination according to the present disclosure as a host material has a higher luminous efficiency and / or longer lifetime characteristics than a conventional organic electroluminescent device.

[0117] The compounds used in the device examples and the comparative examples are provided in Table 2 below.

[0118] [Table 2]

[0119]

Claims

1. A plurality of host materials, the plurality of host materials including a first host material and a second host material, wherein the first host material includes a compound represented by Formula 1: Wherein, Ar represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur; L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; X1 to X8 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, -NR5R6, or -SiR7R8R9; or adjacent ones of X1 to X8 may be connected to each other to form one or more rings; provided that at least one pair of X1 and X2, X2 and X3, X3 and X4, X4 and X5, X5 and X6, X6 and X7, and X7 and X8 may be connected to each other to form one or more rings, wherein the ring has 1 to 5 single rings; R5 to R9 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; or adjacent ones of R5 to R9 may be connected to each other to form one or more rings; and The second host material includes a compound represented by any one of Formulas 2-1 and 2-2: Wherein, X represents -N=, -NR 10 -, -O-, or -S-; Y represents -N=, -NR 11 -, -O-, or -S-; provided that when X represents -N=, Y represents -NR 11 -, -O-, or -S-, and when X represents -NR 10 -, Y represents -N=, -O-, or -S-; Y1 to Y5, and Y 11 to Y 17 each independently represents N or CR 15 ; and R in Y1 to Y5 15 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or 15 adjacent ones in R may be connected to each other to form one or more rings; Y 11 to Y 17 each R 15 independently represents 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 tris(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 tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or R 15 adjacent ones of which may be joined to each other to form one or more rings; L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; Each of R2 to R4 independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or adjacent ones of R2 to R4 may be connected to each other to form one or more rings; R 10 and R 11 each independently represents 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 tris(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 tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; a' represents the integer 1; b' and c' each independently represent the integer 1 or 2; d' represents an integer from 1 to 4; provided that if b', c', and d' are each independently an integer of 2 or greater, then each of R2 to R4 may be the same or different.

2. The multiple main body materials according to claim 1, wherein, Among Ar, L1, X1 to X8, R1 to R 11 , R 15 , and L2, the substituents of the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted alkyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, or the substituted alkylarylamino are each independently at least one selected from the group consisting of: Deuterium; a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a (3- to 7-membered) heterocycloalkyl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; an unsubstituted or (3- to 50-membered) heteroaryl group substituted with at least one of a (C1-C30)alkyl group, a (C6-C30)aryl group, and a di(C6-C30)arylamino group; a (C6-C30)aryl group unsubstituted or substituted with at least one of a cyano group, a (C1-C30)alkyl group, a (3- to 50-membered) heteroaryl group, a di(C6-C30)arylamino group, and a tris(C6-C30)arylsilyl group; a tris(C1-C30)alkylsilyl group; a tris(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; an amino group; a mono- or di-(C1-C30)alkylamino group; a mono- or di-(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylborylcarbonyl group; a di(C1-C30)alkylborylcarbonyl group; a (C1-C30)alkyl(C6-C30)arylborylcarbonyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group.

3. The multiple main materials according to claim 1, wherein, Formula 1 is represented by any one of Formulas 1-1 to 1-10 below: wherein, Ar and L1 are as defined in claim 1; V and W each independently represent CR 12 R 13 、NR 14 、O, or S; R 12 to R 14 、X 11 to X 23 、and X 31 to X 33 each independently represents 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 tris(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 tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; X 24 to X 30 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or X 24 to X 30 adjacent ones among them may be connected to each other to form one or more rings; and a, e through i, k, l, o, p, s, u, y, and z each independently represent an integer from 1 to 4; b through d, j, and m each independently represent an integer from 1 to 6; n and r each independently represent an integer from 1 to 3; q represents the integer 1 or 2; t represents an integer from 1 to 5; in the case where a through u, y, and z are each independently an integer 2 or greater, X 11 through X 33 each of which may be the same or different.

4. The multiple main materials according to claim 1, wherein, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzo[9,10]fluorenyl group, a substituted or unsubstituted benzo[9,10]phenanthrenyl group, a substituted or unsubstituted benzo[1,2-b:4,5-b']dinaphtho[2,3-d:2',3'-f]furan-2-yl group, or a substituted or unsubstituted benzo[1,2-b:4,5-b']dinaphtho[2,3-d:2',3'-f]thiophen-2-yl group.

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

6. The plurality of matrix materials according to claim 1, wherein, The compound represented by Formula 2 is at least one selected from the group consisting of the following compounds:

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

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