Multiple host materials and organic electroluminescent devices containing them

Abstract

To provide a plurality of host materials and an organic electroluminescent device including the same.SOLUTION: The present disclosure relates to a plurality of host materials including a first host compound and a second host compound, and an organic electroluminescent device including the same. Including the host materials makes it possible to provide an organic electroluminescent device with a low driving voltage and / or a high luminous efficiency and / or a long lifetime.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This disclosure relates to multiple host materials and organic electroluminescent devices containing them. [Background technology]

[0002] Organic electroluminescent devices (OLEDs) were first developed in 1987 by Eastman Kodak using small aromatic diamine molecules and aluminum complexes as materials to form the light-emitting layer [(Non-Patent Document 1)].

[0003] The most important factor determining the luminous efficiency in OLEDs is the luminescent material, which must have high quantum efficiency and high electron and hole mobility, and the formed luminescent material layer must be uniform and stable. Liminescent materials are functionally classified into host materials and dopant materials. By using luminescent materials in combination with a host, color purity, luminous efficiency, and stability can be improved. When using such a dopant / host material system as a luminescent material, the selection of the host material is important because it greatly affects the efficiency and lifespan of the light-emitting device.

[0004] Recently, the development of OLEDs with high efficiency and long lifespan has become an urgent issue. In particular, considering the electroluminescent (EL) properties required for medium and large-sized OLED panels, there is an urgent need to develop light-emitting materials that are far superior to conventional light-emitting materials.

[0005] Patent Documents 1, 2, 3, and 4 disclose compounds based on indoloquinoxaline derivatives. However, these references do not specifically disclose any particular combination of host materials as described in this disclosure. In addition, there is a continuing need to develop luminescent materials with improved performance, such as improved driving voltage, luminous efficiency, and / or lifetime characteristics, compared to conventional combinations of compounds disclosed in the aforementioned references. [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Korean Patent Application Publication No. 2010-0108924, Specification A [Patent Document 2] U.S. Patent Application Publication 2011 / 0303901, Specification A1 [Patent Document 3] Korean Patent Application Publication No. 2014-0101699, Specification A [Patent Document 4] Chinese Patent Application Publication No. 107602568, Specification A [Patent Document 5] Korean Patent Application Publication No. 2017-0022865 Specification [Non-patent literature]

[0007] [Non-Patent Document 1] Appl.Phys.Lett.51,913,1987 [Overview of the Initiative] [Problems that the invention aims to solve]

[0008] The object of this disclosure is, firstly, to provide a plurality of host materials that can be used to manufacture organic electroluminescent devices having a low drive voltage and / or high luminescence efficiency and / or long lifespan, and secondly, to provide an organic electroluminescent device comprising a host material. [Means for solving the problem]

[0009] As a result of diligent research to solve the above technical problems, the inventors have found that the aforementioned objectives 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. As a result, the present invention has been completed.

[0010] [ka] In Equation 1, L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; and R1 to R8 are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 member) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, substituted or unsubstituted fused ring of (C3 to C30) aliphatic ring and (C6 to C30) aromatic ring, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted mono- or di-(C2 to C30) alkeni Represents a arylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or may be bonded to adjacent substituents to form a ring.

[0011] [ka] In Equation 2, X 21 and Y 21 These are -N= and -NR, respectively, independently. 25 - represents -O- or -S-, except X 21 and Y 21 One of them is -N= and X 21 and Y 21 Others include -NR 25 -, -O-, or -S-; R21 represents a substituted or unsubstituted (C6 - C30) aryl or a substituted or unsubstituted (3 - 30 member) heteroaryl; R 22 ~R 25 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 - 30 member) heteroaryl, a substituted or unsubstituted (C3 - C30) cycloalkyl, a substituted or unsubstituted (C1 - C30) alkoxy, a substituted or unsubstituted tri(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 tri(C6 - C30) arylsilyl, a substituted or unsubstituted condensed ring of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, a substituted or unsubstituted mono- or di-(C1 - C30) alkylamino, a substituted or unsubstituted mono- or di-(C2 - C30) alkenylamino, a substituted or unsubstituted (C1 - C30) alkyl(C2 - C30) alkenylamino, a substituted or unsubstituted mono- or di-(C6 - C30) arylamino, a substituted or unsubstituted (C1 - C30) alkyl(C6 - C30) arylamino, a substituted or unsubstituted mono- or di-(3 - 30 member) heteroarylamino, a substituted or unsubstituted (C1 - C30) alkyl(3 - 30 member) heteroarylamino, a substituted or unsubstituted (C2 - C30) alkenyl(C6 - C30) arylamino, a substituted or unsubstituted (C2 - C30) alkenyl(3 - 30 member) heteroarylamino or a substituted or unsubstituted (C6 - C30) aryl(3 - 30 member) heteroarylamino; or they may be bonded to adjacent substituents to form a ring; provided that at least one of R 22 ~R 24 is -L 21 -Ar 21 on the condition that; L 21 represents a single bond or a substituted or unsubstituted (C6 - C30) arylene; Ar 21This refers to a substituted or unsubstituted condensed ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or -NR. 31 R 32 It represents; R 31 and R 32 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; e and f each independently represent an integer of 1 or 2, and g represents an integer from 1 to 4; and If e~g is an integer greater than or equal to 2, then R 22 Each of the following, R 23 Each of and R 24 Each of them may be the same or different.

[0012] Advantageous effects of the invention By using multiple host materials according to this disclosure, organic electroluminescent devices having low drive voltage and / or high luminescence efficiency and / or long lifetime can be prepared. [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 invention in any way.

[0014] This disclosure relates to a plurality of host materials and an organic electroluminescent device comprising host materials, each comprising at least one first host material represented by formula 1 and at least one second host material represented by formula 2.

[0015] In addition, this disclosure relates to an organic electroluminescent compound represented by Formula 3, an organic electroluminescent material containing the same, and an organic electroluminescent device containing the organic electroluminescent material.

[0016] In this disclosure, the term "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and may contain at least one compound. 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 (containing a host and dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0017] 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, multiple organic electroluminescent materials 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. Such at least two compounds may be contained in the same layer or different layers, may be evaporated together or simultaneously, or may be evaporated individually.

[0018] In this disclosure, the term “multiple host materials” means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both the material before (e.g., before deposition) inclusion in the organic electroluminescent device and the material after (e.g., after deposition) inclusion in the organic electroluminescent device. The multiple host materials of this disclosure may be included in any light-emitting layer constituting the organic electroluminescent device. At least two compounds included in the multiple host materials may be included together in one light-emitting layer or each may be included in a separate light-emitting layer. If at least two host materials are included in one layer, the at least two host materials may mix and evaporate to form a layer, or they may co-evaporate individually and simultaneously to form a layer.

[0019] In this disclosure, 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, tert-butyl, sec-butyl, etc. In this specification, the term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In this disclosure, the term "(C6-C30)aryl(len)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6-30 carbon atoms in the ring skeleton (wherein the number of carbon atoms in the ring skeleton is preferably 6-20, more preferably 6-15), and may be partially saturated. The aryl may include a spiro structure. Examples of aryl compounds include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenantrenyl, benzophenantrenyl, phenylphenantrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azlenyl, tetramethyl-dihydrophenantrenyl, and others. More specifically, aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl,4'-Methylbiphenyl, 4''-t-butyl-p-terphenyl4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl4-yl, m-terphenyl3-yl, m-terphenyl2-yl, p-terphenyl4-yl, p-terphenyl3-yl, p-terphenyl2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, ben Zo[c]phenanthryl, benzo[g]crisenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 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- 4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl Luorenyl, 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 Nyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl,11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl- These may include 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, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenantrenyl, etc. In this specification, "(3-30 member) heteroaryl(len)" is an aryl having 3 to 30 ring skeleton atoms, including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, where the number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20. The heteroaryls described above may be monocyclic rings or fused rings formed by condensation with at least one benzene ring; they may be partially saturated. Furthermore, the heteroaryls or heteroarylenes described herein may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may include spiro structures. Examples of heteroaryls include, specifically, monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, etc.; and benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, dibenzoselenophenyl, benzofloquinolinil, benzofloquinazolinil, benzoflonaftylidinyl, benzoflopyrimidinyl,Naphthoflopyrimidinyl, benzothienocinolinyl, benzothienocinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphthiothienopyrimidinyl, pyrididoindolyl, benzopyrimidoindolyl, benzoflopyradinyl, naphthoflopyradinyl, benzothienopyradinyl, naphthiothienopyradinyl, pyrazinoindolyl, benzopyradinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyrimidinyl, isoindolyl, indolyl, benzoindolyl, indazo Examples of condensed ring heteroaryls include lyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenantridinyl, benzodioxolyl, indolidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenadinyl, imidazopyridinyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzopyrimidinyl, indocarbazolyl, indenocarbazolyl, etc. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 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, 7-indolidinyl, 8-Indolidinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 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-isox, Noryl, 4-isoquinoryl, 5-isoquinoryl, 6-isoquinoryl, 7-isoquinoryl, 8-isoquinoryl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl 1-Phenantridinyl, 2-Phenantridinyl, 3-Phenantridinyl, 4-Phenantridinyl, 6-Phenantridinyl, 7-Phenantridinyl, 8-Phenantridinyl, 9-Phenantridinyl, 10-Phenantridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrole-1-yl, 2-Methylpyrrole Rol-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-t-butyl-1-indolly, 4-t-butyl-1-indolly, 2-t-butyl-3-indolly, 4-t- 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, 6-naphtho-[1,2-b]-benzofuranyl, 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]-Benzofuranil, 9-Naphtho-[2,1-b]-Benzofuranil Furanyl, 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, 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-naphtho-[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 O[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]pyradinyl, 6-benzoflo[3,2-d]pyradinyl, 7-benzoflo[3,2-d]pyradinyl, 8-benzoflo[3,2-d]pyradinyl, 9-benzoflo[3,2-d]pyradinyl, 2-benzothio[3,2-d]pyradinyl, 6-benzothio[3,2-d]pyradinyl, 7-benzothio[3,2-d]pyradinyl, 8-benzothio[3,This could be 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. In this specification, the term "(C3~C30) aliphatic ring and (C6~C30) aromatic ring condensation ring" means a ring formed by condensing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 3 to 25, more preferably 3 to 18) with at least one aromatic ring having 6 to 30 ring skeleton carbon atoms (wherein the number of carbon atoms is preferably 6 to 25, more preferably 6 to 18). For example, the fused ring may be a fused ring of at least one benzene ring and at least one cyclohexane ring, or a fused ring of at least one naphthalene ring and at least one cyclopentane ring, etc. In this specification, carbon atoms in the fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The term "halogen" in this disclosure includes F, Cl, Br, and I.

[0020] In addition, "ortho (o)", "meta (m)", and "para (p)" in this disclosure refer to the substitution positions of all substituents. The ortho position is a compound having substituents adjacent to each other, i.e., at positions 1 and 2 on the benzene ring. The meta position is the substitution position immediately following the directly adjacent substitution position, i.e., a compound having substituents at positions 1 and 3 on the benzene ring. The para position is the substitution position immediately following the meta position, i.e., a compound having substituents at positions 1 and 4 on the benzene ring.

[0021] In this specification, “a ring formed by bonding to adjacent substituents” means a substituted or unsubstituted (3 to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof, formed by bonding or condensing two or more adjacent substituents, preferably a substituted or unsubstituted (5 to 25-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of this disclosure, the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of this disclosure, the number of atoms in the ring skeleton is 5 to 15. In one embodiment, the condensed ring may be, for example, 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 benzofluorene 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, a substituted or unsubstituted carbazole ring, and the like.

[0022] In addition, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group, i.e., a substituent, and that the group is substituted by a group in which two or more substituents are bonded between substituents. For example, a "substituent in which two or more substituents are bonded" could be a pyridine-triazine. That is, a pyridine-triazine could be a heteroaryl or can be interpreted as a single substituent in which two heteroaryls are bonded. Preferably, the formulas of this disclosure include substituted (C1-C30) alkyl, substituted (C6-C30) aryl(len), substituted (3-30 member) heteroaryl(len), substituted (C3-C30) cycloalkyl, substituted (C1-C30) alkoxy, substituted condensed ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30 )alkyldi(C6~C30)arylsilyl, substituted tri(C6~C30)arylsilyl, substituted mono- or di-(C1~C30)alkylamino, substituted mono- or di-(C2~C30)alkenylamino, substituted (C1~C30)alkyl(C2~C30)alkenylamino, substituted mono- or di-(C6~C30)arylamino, substituted (C1~C30)alkyl(C6~C30)arylamino, substituted mono- or di-(3~30 member) hetero The substituents of arylamino, substituted (C1-C30) alkyl (3-30 member) heteroarylamino, substituted (C2-C30) alkenyl (C6-C30) arylamino, substituted (C2-C30) alkenyl (3-30 member) heteroarylamino, and substituted (C6-C30) aryl (3-30 member) heteroarylamino are, independently, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, phosphine oxide, (C1-C3 0) 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)aryl-substituted (5~30 member) heteroaryl,(C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, condensed ring 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, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3-30) heteroarylamino, ( At least one selected from the group consisting of 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) arylphosphinyl, di(C6-C30) arylboronyl, di(C1-C30) alkylboronyl, (C1-C30) alkyl(C6-C30) arylboronyl, (C6-C30)ar(C1-C30) alkyl, and (C1-C30) alkyl(C6-C30) aryl. For example, the substituents may be deuterium, methyl, phenyl, biphenyl, naphthyl, or carbazolyl.

[0023] The following describes a host material according to one embodiment.

[0024] A plurality of host materials according to one embodiment includes a first host material containing a compound represented by formula 1 above and a second host material containing a compound represented by formula 2 above; the plurality of host materials may be contained in the light-emitting layer of an organic electroluminescent device according to one embodiment.

[0025] In one embodiment, the first host material may include a compound represented by the following formula 1. [ka]

[0026] In Equation 1, L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; and R1 to R8 are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, substituted or unsubstituted (3 to 30 member) heteroaryl, substituted or unsubstituted tri(C1 to C30) alkylsilyl, substituted or unsubstituted di(C1 to C30) alkyl(C6 to C30) arylsilyl, substituted or unsubstituted (C1 to C30) alkyldi(C6 to C30) arylsilyl, substituted or unsubstituted tri(C6 to C30) arylsilyl, substituted or unsubstituted fused ring of (C3 to C30) aliphatic ring and (C6 to C30) aromatic ring, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted mono- or di-(C2 to C30) alkeni Represents a arylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or may be bonded to adjacent substituents to form a ring.

[0027] In one embodiment, L1 may be a single-bonded, substituted or unsubstituted (C6-C25) arylene or a substituted or unsubstituted (5-30 member) heteroarylene, preferably a single-bonded, substituted or unsubstituted (C6-C18) arylene or a substituted or unsubstituted (5-25 member) heteroarylene, more preferably a single-bonded, substituted or unsubstituted (C6-C12) arylene or a substituted or unsubstituted (5-18 member) heteroarylene. For example, L1 may be a single-bonded, unsubstituted or phenyl-substituted phenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.

[0028] In one embodiment, Ar1 may be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 member) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 member) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-18 member) heteroaryl. For example, Ar1 may be a phenyl;phenyl substituted with at least two unsubstituted or deuterium-substituted phenyls, and a phenyl, unsubstituted m-biphenyl, unsubstituted m-terphenyl, unsubstituted naphthyl, or naphthyl substituted with an unsubstituted or deuterium-substituted phenyl, unsubstituted pyridyl, or pyridyl substituted with an unsubstituted or deuterium-substituted phenyl, unsubstituted dibenzofuranyl, or unsubstituted dibenzothiophenyl.

[0029] In one embodiment, R1 to R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C6 to C30) aryl or substituted or unsubstituted (3 to 30 member) heteroaryl, preferably hydrogen, unsubstituted or (C6 to C25) aryl substituted with at least one deuterium; unsubstituted or (C6 to C25) aryl; (5 to 30 member) heteroaryl; di(C6 to C30) arylamino; and (C6 to C30) aryl(5 to It may be a 30-membered heteroarylamino or a substituted or unsubstituted (5-30 member) heteroaryl, more preferably a (C6-C18) aryl substituted with at least one hydrogen, unsubstituted or deuterium; an unsubstituted or deuterium-substituted (C6-C18) aryl; a (5-25 member) heteroaryl; a di(C6-C25) arylamino; and a (C6-C25) aryl(5-25 member) heteroarylamino or a substituted or unsubstituted (5-25 member) heteroaryl.

[0030] For example, at least one of R1 to R4 or at least one of R5 to R8 may be any one of the substituents listed in Group 1 below, and the substituents listed in Group 1 below may be substituted with one or more deuterium atoms, but are not limited to them. [Group 1] [ka]

[0031] A compound represented by formula 1 above in one embodiment may be represented by the following formulas 1-1 or 1-2. [ka]

[0032] In equations 1-1 and 1-2, L1 and Ar1 are as defined in Equation 1; L2 and L3 each independently represent a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar2 and Ar3 independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, a substituted or unsubstituted di(C6-C30) arylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; a and b each independently represent an integer of 1 or 2; and If a and b are integers of 2, then each of Ar2 and each of Ar3 can be the same or different.

[0033] In one embodiment, L2 and L3 may each independently be a single bond, an unsubstituted phenylene, or a phenylene substituted with an unsubstituted or one or more deuterium atoms, an unsubstituted m-biphenylene, or an unsubstituted p-biphenylene.

[0034] In one embodiment, when a and b are integers of 2, L2 and L3 can each be independently substituted or unsubstituted (C6-C30) arylenes, such as unsubstituted phenylene.

[0035] In one embodiment, Ar2 and Ar3 are each independently unsubstituted or substituted with at least one deuterium (C6-C30)aryl; unsubstituted or deuterium-substituted (C6-C30)aryl; (3-30 member) heteroaryl; di(C6-C30)arylamino; and (C6-C30)aryl(3-30 member) heteroarylamino, substituted or unsubstituted (5-30 member) heteroaryl, substituted or unsubstituted di(C6-C30)arylamino or substituted or unsubstituted (C6-C30)aryl(5-30 member) heteroarylamino, preferably unsubstituted or substituted with at least one deuterium (C6-C25)aryl; unsubstituted or deuterium-substituted (C6-C25)aryl; (5-30 member) heteroaryl; di(C6-C25)arylamino; and The following are possible: (C6-C25)aryl (5-30 member) heteroarylamino, substituted or unsubstituted (5-25 member) heteroaryl, substituted or unsubstituted di(C6-C25)arylamino or substituted or unsubstituted (C6-C25)aryl (5-25 member) heteroarylamino, more preferably unsubstituted or deuterium-substituted (C6-C18)aryl; unsubstituted or deuterium-substituted (C6-C18)aryl; (5-25 member) heteroaryl; di(C6-C18)arylamino; and (C6-C18)aryl (5-25 member) heteroarylamino, substituted or unsubstituted (5-18 member) heteroaryl, substituted or unsubstituted di(C6-C18)arylamino or substituted or unsubstituted (C6-C18)aryl (5-18 member) heteroarylamino.For example, Ar2 and Ar3 can each independently be unsubstituted or phenyl substituted with at least one deuterium; unsubstituted or deuterium-substituted phenyl; naphthyl; dibenzofuranyl; dibenzothiophenyl; diphenylamino; phenylbiphenylamino; phenyldibenzofuranylamino; and phenyldibenzothiophenylamino, unsubstituted naphthyl, unsubstituted o-biphenyl, unsubstituted m-biphenyl, unsubstituted or phenyl-substituted p-biphenyl, unsubstituted p-terphenyl, or unsubstituted or phenyl-substituted p-terphenyl, unsubstituted m-terphenyl, or unsubstituted or phenyl-substituted m-terphenyl, unsubstituted o-terphenyl, unsubstituted phenantrenyl, unsubstituted crisenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted diphenylamino, unsubstituted phenylbiphenylamino, unsubstituted phenyldibenzofuranylamino, or unsubstituted phenyldibenzothiophenylamino.

[0036] A compound represented by formulas 1-1 and 1-2 above according to one embodiment may be a first host material in which L1 represents a single bond; Ar1 ​​represents a pyridyl substituted with deuterium or (C6-C30)aryl; L2 and L3 are single bonds or substituted or unsubstituted phenylene; Ar2 and Ar3 each independently represent an unsubstituted or (C6-C30)aryl (C6-C30)aryl; and a and b each independently represent an integer of 1 or 2.

[0037] In one embodiment, the first host material represented by Formula 1 above may be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka]

[0038] The compounds represented by Formula 1 of this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, they can be prepared by referring to, but are not limited to, the following reaction schemes 1 or 2. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka]

[0039] In reaction schemes 1 and 2 described above, the substituents are defined as defined in formula 1, where a and b are integers from 1 to 4, and Hal represents a halogen atom.

[0040] As described above, exemplary synthetic examples of compounds represented by Formula 1 in this disclosure are provided, and these are based on reactions such as the Buchwald-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, and phosphine-mediated reductive cyclization reaction. It will be understood by those skilled in the art that these reactions proceed even when other substituents defined in Formula 1, other than those described in the specific synthetic examples, are attached.

[0041] A second host material, as an alternative host material according to one embodiment, may include a compound represented by the following formula 2. [ka]

[0042] In Equation 2, X 21 and Y 21 These are -N= and -NR, respectively, independently. 25 - represents -O- or -S-, except X 21 and Y 21 One of them is -N= and X 21 and Y 21 Others include -NR 25 -, -O-, or -S-; R 21 This represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; R 22 ~R 25Each of these independently consists of 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 condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted Represents a substituted mono- or di-(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or may be bonded to an adjacent substituent to form a ring; However, R 22 ~R 24 At least one of them is -L 21 -Ar 21 On the condition that; L 21 This represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar 21 This refers to a substituted or unsubstituted condensed ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or -NR. 31R 32 It represents; R 31 and R 32 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; e and f each independently represent an integer of 1 or 2, and g represents an integer from 1 to 4; and If e~g is an integer greater than or equal to 2, then R 22 Each of the following, R 23 Each of and R 24 Each of them may be the same or different.

[0043] A second host material represented by the above formula 2 according to one embodiment may be represented by any one of the following formulas 2-1 to 2-3. [ka]

[0044] In equations 2-1 to 2-3, X 21 , Y 21 , L 21 Ar 21 , R 21 ~R 24 e, f, and g are as defined in Equation 2; g' represents an integer from 1 to 3; and If g' is an integer greater than or equal to 2, then R 24 Each of them may be the same or different.

[0045] In one embodiment, in formulas 2-1 to 2-3, X 21 and Y 21 One of them is -N= and X 21 and Y 21 Others can be -O- or -S-;R 21 This can be a substituted or unsubstituted (C6-C30) aryl; R 22 ~R 24 All of it can be hydrogen; L21 It can be a single bond or a substituted or unsubstituted (C6~C30) arylene; Ar 21 This refers to a substituted or unsubstituted condensed ring of an (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or -NR. 31 R 32 And here, R 31 and R 32 Each of these can independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl.

[0046] In one embodiment, R 21 This can be a substituted or unsubstituted (C6-C30) aryl, preferably a substituted or unsubstituted (C6-C25) aryl, more preferably a substituted or unsubstituted (C6-C18) aryl. For example, R 21 This can be an unsubstituted phenyl or an unsubstituted p-biphenyl.

[0047] In one embodiment, L 21 The arylenes may be single-bonded, substituted, or unsubstituted (C6-C30) arylenes, preferably single-bonded, substituted, or unsubstituted (C6-C25) arylenes, and more preferably single-bonded, substituted, or unsubstituted (C6-C18) arylenes. For example, L 21 This can be a single bond, unsubstituted phenylene, or unsubstituted naphthalenylene.

[0048] In one embodiment, Ar 21 This refers to a substituted or unsubstituted fused ring of an (C5-C25) aliphatic ring and a (C6-C25) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or -NR. 31 R 32 It is possible. In one embodiment, R 31 and R 32Each of these can independently be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 member) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 member) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5-18 member) heteroaryl. For example, Ar 21This includes substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenantrenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted fluoranteyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentan-fluoren]yl, substituted or unsubstituted spiro[dihydroindene-fluoren]yl, substituted or unsubstituted spiro[benzofluoren-fluoren]yl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibe It may be benzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted dibenzofuranil, substituted or unsubstituted benzofuranil, or substituted or unsubstituted benzonaphthofuranil; or amino; fluorenyl substituted with at least one substituent selected from the group consisting of phenyl; m-biphenyl; p-biphenyl; o-terphenyl; m-terphenyl; p-terphenyl; amino; fluorenyl substituted with at least one methyl or phenyl, e.g., 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl; benzofluorenyl substituted with at least one methyl, e.g., 7,7-dimethyl-7H-benzofluorenyl; phenantrenyl; unsubstituted or phenyl-substituted dibenzothiophenyl; benzonaphthofuranil; and unsubstituted or phenyl-substituted dibenzofuranil.

[0049] In one embodiment, the second host material represented by Formula 2 above may be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0050] A compound represented by formula 2 in one embodiment can be produced by synthetic methods known to those skilled in the art. In particular, preparations using synthetic methods disclosed in numerous patent documents can be used. For example, it can be synthesized in accordance with the method disclosed in (Patent Document 5) (published March 2, 2017), but is not limited thereto.

[0051] An organic electroluminescent compound according to another embodiment of the present disclosure may be represented by the following formula 3. [ka]

[0052] In Equation 3, L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl; R1~R8 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C30) alkyl, substituted or unsubstituted (C6~C30) aryl (excluding anthracene), substituted or unsubstituted (3~30 member) heteroaryl, 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 of (C3~C30) aliphatic ring and (C6~C30) aromatic ring, substituted or unsubstituted mono- or di-(C1~C30) alkylamino, substituted or unsubstituted mono- or di-(C2~C30) ) represents an alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or may be bonded to an adjacent substituent to form a ring; However, at least one of R1 to R4 or at least one of R5 to R8 is -L 11 -(Ar 11 ) a On the condition that it represents; L 11 This represents a single bond or a substituted or unsubstituted (C6-C30) arylene excluding anthracenylene; Ar 11This represents substituted or unsubstituted (C6-C30) aryls other than anthracene, substituted or unsubstituted pyridyls, substituted or unsubstituted dibenzofuranyls, or substituted or unsubstituted dibenzothiophenyls; a is an integer of 1 or 2; and If a is an integer of 2, then Ar 11 Each of them may be the same or different; However, Ar1, R1~R8, L 11 and Ar 11 If the compound is a substituted (C6-C30)aryl(len), then cases where the (C6-C30)aryl(len) is substituted with an amino group are excluded.

[0053] In one embodiment, L1 may be a single-bonded, substituted, or unsubstituted (C6-C25) arylene, preferably a single-bonded, substituted, or unsubstituted (C6-C18) arylene, and more preferably a single-bonded, substituted, or unsubstituted (C6-C12) arylene. For example, L1 may be a single-bonded, unsubstituted, or phenyl-substituted phenylene or unsubstituted naphthylene.

[0054] In one embodiment, Ar1 may be a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted dibenzofuranil, or a substituted or unsubstituted dibenzothiophenyl, preferably a substituted or unsubstituted (C6-C25) aryl, an unsubstituted or (C6-C30) substituted pyridyl, a substituted or unsubstituted dibenzofuranil, or a substituted or unsubstituted dibenzothiophenyl, more preferably a substituted or unsubstituted (C6-C18) aryl, an unsubstituted or (C6-C18) substituted pyridyl, an unsubstituted dibenzofuranil, or an unsubstituted dibenzothiophenyl. For example, Ar1 may be an unsubstituted or deuterium-substituted phenyl, an unsubstituted or phenyl-substituted phenyl; naphthyl; dibenzofuranyl; and dibenzothiophenyl, an unsubstituted m-biphenyl, an unsubstituted m-terphenyl, an unsubstituted naphthyl, or an unsubstituted naphthyl or naphthyl substituted with one or more deuterium-substituted phenyl, an unsubstituted pyridyl, or an unsubstituted pyridyl or pyridyl substituted with one or more deuterium-substituted phenyl, an unsubstituted dibenzofuranyl, or an unsubstituted dibenzothiophenyl.

[0055] In one embodiment, R1 to R8 may each independently be a substituted or unsubstituted (C6 to C30) aryl or substituted or unsubstituted (5 to 30 member) heteroaryl, excluding hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, or anthracene, preferably at least one (C6 to C30) aryl-substituted or unsubstituted (C6 to C25) aryl or substituted or unsubstituted (5 to 25 member) heteroaryl, excluding hydrogen, deuterium, or anthracene, more preferably at least one (C6 to C30) aryl-substituted or unsubstituted (C6 to C18) aryl or substituted or unsubstituted (5 to 25 member) heteroaryl, provided that at least one of R1 to R4 or at least one of R5 to R8 is -L 11 -(Ar 11 ) a This is conditional on the following:

[0056] In one embodiment, L11 may be a single bond, unsubstituted phenylene, or phenylene substituted with phenyl which is unsubstituted or substituted with one or more deuteriums, unsubstituted m-biphenylene or unsubstituted p-biphenylene.

[0057] In one embodiment, when a is an integer of 2, L 11 may be substituted or unsubstituted (C6-C30) arylene excluding anthracene, for example, unsubstituted phenylene.

[0058] In one embodiment, Ar 11 is phenyl which is unsubstituted or substituted with at least one of one or more deuteriums; phenyl which is unsubstituted or substituted with deuterium; naphthyl; dibenzofuranyl; and dibenzothiophenyl, unsubstituted naphthyl, unsubstituted o-biphenyl, unsubstituted m-biphenyl, unsubstituted or phenyl-substituted p-biphenyl, unsubstituted p-terphenyl or p-terphenyl substituted with phenyl which is unsubstituted or substituted with one or more deuteriums, unsubstituted m-terphenyl or m-terphenyl substituted with phenyl which is unsubstituted or substituted with one or more deuteriums, unsubstituted o-terphenyl, unsubstituted phenanthrenyl, unsubstituted chrysenyl, unsubstituted dibenzofuranyl or unsubstituted dibenzothiophenyl.

[0059] In Formula 3, when Ar1, R^1~R^8, L [[ID=1S]] 11 and Ar 11 are substituted (C6-C30) aryl(ene), cases where the (C6-C30) aryl(ene) is substituted with an amino group are excluded.

[0060] The compounds represented by Formula 3 above may be more specifically exemplified by, but not limited to, the following compounds.

Chemical formula

Chemical formula

Chemical formula

[0061] The following describes organic electroluminescent devices to which the aforementioned host materials and / or organic electroluminescent compounds are applied.

[0062] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer placed between the first and second electrodes. The organic layer may include a light-emitting layer, which may include a plurality of host materials, including a first host material containing at least one compound represented by formula 1 above, and a second host material containing at least one compound represented by formula 2 above. According to another embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one light-emitting layer placed between the first and second electrodes, wherein the at least one light-emitting layer may contain a compound represented by formula 3 above.

[0063] According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one compound C-1 to C-131 as a first host material represented by formula 1 and at least one compound H-1 to H-220 as a second host material represented by formula 2. Multiple host materials may be contained in the same organic layer, e.g., an emissive layer, or each may be contained in different emissive layers. According to another embodiment, the organic electroluminescent material of the present disclosure comprises compound C-1 to C-127 represented by formula 3, either individually or in combination of two or more, and the organic electroluminescent material may be contained in an organic layer, e.g., an emissive layer, of an organic electroluminescent device.

[0064] The organic layer may further include, in addition to the light-emitting layer, at least one layer selected from hole injection layers, hole transport layers, hole auxiliary layers, light-emitting auxiliary layers, electron transport layers, electron injection layers, intermediate layers, hole blocking layers, electron blocking layers, and electron buffer layers. The organic layer may further include amine compounds and / or azine compounds in addition to the light-emitting material of this disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may include amine compounds, such as arylamine compounds and styrylarylamine compounds, as hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, or electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include azine compounds as electron transport material, electron injection material, electron buffer material, and hole blocking material. In addition, the organic layer further comprises at least one metal selected from the group consisting of metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic d-transition elements, or at least one complex compound containing such a metal.

[0065] Multiple host materials according to one embodiment can be used as light-emitting materials for white organic light-emitting devices. Depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units, various structures such as parallel side-by-side arrangement, stacked arrangement, or color conversion material (CCM) method have been proposed for white organic light-emitting devices. In addition, the organic electroluminescent material according to one embodiment can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0066] One of the first and second electrodes may be an anode, and the other may be a cathode. Here, the first and second electrodes may be formed from a permeable conductive material, a semi-permeable conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be top-emitting, bottom-emitting, or double-emitting depending on the type of material forming the first and second electrodes.

[0067] 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 be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each layer may use two compounds simultaneously. In addition, the hole injection layer may be doped as a p-type dopant. An electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer to prevent light leakage by confining excitons within the light-emitting layer by preventing electron overflow from the light-emitting layer. The hole transport layer or electron blocking layer may be multilayered, where each layer may use multiple compounds.

[0068] 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 be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each layer may use two compounds simultaneously. The hole blocking layer may be placed between the electron transport layer (or electron injection layer) and the light-emitting layer to block the arrival of holes to the cathode, thereby improving the probability of electron-hole recombination in the light-emitting layer. The hole blocking layer or electron transport layer may also be multilayered, where each layer may use multiple compounds. The electron injection layer may also be doped as an n-type dopant.

[0069] A luminescence auxiliary layer may be placed between the anode and the luminescence layer, or between the cathode and the luminescence layer. When the luminescence auxiliary layer is placed between the anode and the luminescence layer, it can be used to facilitate hole injection and / or hole transport or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the luminescence layer, it can be used to facilitate electron injection and / or electron transport or to prevent hole overflow. In addition, a hole auxiliary layer may be placed between a hole transport layer (or hole injection layer) and the luminescence layer, and may be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. If the organic electroluminescent device includes two or more hole transport layers, any additionally included hole transport layers may be used as hole auxiliary layers or electron blocking layers. Luminescence auxiliary layers, hole auxiliary layers, or electron blocking layers may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0070] In the organic electroluminescent device of this disclosure, preferably, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as the "surface layer") may be disposed on the inner surface of one or both electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X Examples of metal halides (1≦X≦1.5) include SiON and SiAlON; examples of metal halides include LiF, MgF2, CaF2, and rare earth metal fluorides; and examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, and CaO.

[0071] Furthermore, in the organic electroluminescent devices of this disclosure, preferably, a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant may be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, thus facilitating the injection and transport of electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cations, thus facilitating the injection and transport of holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds, and the reducing dopant comprises alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0072] An organic electroluminescent device according to one embodiment may further include at least one dopant in the light-emitting layer.

[0073] The dopants included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent devices of this disclosure is not particularly limited, but is preferably a metallized complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt); more preferably an orthometallated complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt); and even more preferably an orthometallated iridium complex compound as necessary.

[0074] The dopants included in the organic electroluminescent devices of this disclosure may be, but are not limited to, compounds represented by the following formula 101. [ka]

[0075] In formula 101, L is one of the following structures 1 to 3: [Chemical formula] selected from any one of; R 100 ~R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl or substituted or unsubstituted (C-1-C30) alkoxy, or is bonded to adjacent substituents to form, together with pyridine, a ring, such as a substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline or substituted or unsubstituted indenofluoroquinoline; R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, 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 is bonded to adjacent substituents to form, together with benzene, a ring, such as a substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine or substituted or unsubstituted benzothienopyridine; R 201 ~R 220Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be bonded to an adjacent substituent to form a substituted or unsubstituted ring; and 's' represents an integer between 1 and 3.

[0076] In particular, specific examples of dopant compounds include, but are not limited to, the following. [ka] [ka] [ka] [ka] [ka] [ka]

[0077] To form each layer of the organic electroluminescent device of this disclosure, dry deposition methods such as vacuum evaporation, sputtering, plasma deposition, and ion plating, or wet deposition methods such as spin coating, dip coating, and flow coating can be used. When using a wet deposition method, the thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent can be any solvent that can dissolve or diffuse the material forming each layer and does not have any problems with film formation ability.

[0078] In one embodiment, when a layer is formed by a first host material and a second host material, the layer can be formed by the method described above, and in many cases, by co-evaporation or mixed evaporation. Co-evaporation is a mixed evaporation method in which two or more materials are placed in separate 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 evaporation, and then an electric current is passed through one cell to evaporate the materials.

[0079] According to one embodiment, when a first host material and a second host material are present in the same or different layers of an organic electroluminescent device, the layers of the two host compounds can be formed separately. For example, the second host material can be deposited after the first host material has been deposited.

[0080] According to one embodiment, the present disclosure can provide a display device comprising a plurality of host materials, including a first host material comprising a compound represented by formula 1 and a second host material comprising a compound represented by formula 2, or a single host comprising an organic electroluminescent compound represented by formula 3. In addition, by using the organic electroluminescent device of the present disclosure, display devices for smartphones, tablets, notebooks, PCs, TVs, etc., or display devices for vehicles, or lighting devices such as outdoor or indoor lighting can be prepared.

[0081] This disclosure includes the following embodiments 1 to 12. [Aspect 1] A plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following formula 1, and the second host material comprises the following formula 2: [ka] ( During the ceremony, L 1 This represents a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; Ar 1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; and R 1~R 8 Each of these independently comprises 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 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 of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenylamino This represents a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or it may be bonded to an adjacent substituent to form a ring;

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Examples

[0082] [Example 1] Synthesis of Compound H-201

Chem.

[0083] 2) Synthesis of compound H-201 Compound 1 (4.9 g, 12.76 mmol), Compound 2 (4.2 g, 14.0 mmol), Pd(dba3)2 (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol), and 65 mL of o-xylene were added to a flask and stirred at 160 °C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate, and the mixture was then dried. Next, it was separated by column chromatography to obtain Compound H-201 (5.6 g, yield: 68.3%).

[0084] [Table 1]

[0085] [Example 2] Synthesis of compound H-183 [ka] Compound 3 (25 g, 74.48 mmol), Compound 2 (42.58 g, 81.93 mmol), Pd(OAc)2 (0.16 g, 7.5 mmol), P(t-Bu)3 (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol), and 284.09 mL of o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate, followed by drying. Next, it was separated by column chromatography to obtain Compound H-183 (23.4 g, yield: 50%).

[0086] [Table 2]

[0087] [Example 3] Synthesis of compound H-217 [ka] Compound 4 (20 g, 56.96 mmol), Compound 2 (18.8 g, 57.13 mmol), Pd(OAc)2 (0.13 g, 5.7 mmol), P(t-Bu)3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol), and 227.27 mL of o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate, and the mixture was then dried. The mixture was then separated by column chromatography to obtain Compound H-217 (12.5 g, yield: 34%).

[0088] [Table 3]

[0089] [Example 4] Synthesis of compound H-199 [ka] Compound S1 (25 g, 74.48 mmol), Compound 2 (42.58 g, 81.93 mmol), Pd(OAc)2 (0.16 g, 7.5 mmol), P(t-Bu)3 (0.28 g, 7.5 mmol), NaOt-Bu (14.31 g, 150 mmol), and 284.09 mL of o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The remaining water was removed with magnesium sulfate, and the mixture was then dried. The mixture was then separated by column chromatography to obtain Compound H-199 (23.4 g, yield: 50%).

[0090] [Table 4]

[0091] [Example 5] Synthesis of Compound C-8 [ka] 1) Synthesis of compound 1-1 Compound A (25 g, 137.68 mmol), compound B (12.4 g, 114.73 mmol), and 300 mL of ethanol were added to a flask and dissolved. The mixture was then refluxed at 120°C for 6 hours. After the reaction was complete, the resulting solid was filtered with methanol to obtain compound 1-1 (21.5 g, yield: 74%).

[0092] 2) Synthesis of Compounds 1-2 Compound 1-1 (10 g, 39.41 mmol), 2-iodonaphthalene (15 g, 59.12 mmol), CuI (3.7 g, 19.70 mmol), EDA (3 mL, 39.41 mmol), and Cs2CO3 (25 g, 78.82 mmol) in a flask were dissolved in 200 mL of o-DCB and then refluxed at 180 °C for 6 hours. Next, the reaction mixture was stirred at room temperature for 1 hour, and then methanol and distilled water were added thereto. After the reaction was complete, the resulting solid was filtered with methanol, and the filtrate was distilled under reduced pressure. Next, it was separated by column chromatography to obtain compound 1-2 (4.7 g, yield: 48%).

[0093] 3) Synthesis of compound C-8 Compounds 1-2 (3g, 7.89 mmol), compound C (2.6g, 9.47 mmol), Pd2(dba)3 (360mg, 0.394 mmol), S-phos (323mg, 0.789 mmol), NaOtBu (1.8g, 19.72 mmol), and 50 mL of o-xylene were added to a flask and dissolved, then stirred under reflux for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and then distilled water was added. Next, the organic layer was extracted with methylene chloride (MC), then the remaining water was removed with magnesium sulfate, followed by drying. Next, it was distilled under reduced pressure and then separated by column chromatography to obtain compound C-8 (2.0g, yield: 44%).

[0094] [Table 5]

[0095] In order to understand this disclosure in detail, the following describes the method for preparing an organic electroluminescent device containing multiple host materials and its properties according to this disclosure.

[0096] [Device Example 1] Preparation of an OLED containing multiple host materials according to the present disclosure An OLED was manufactured according to this disclosure. First, a transparent electrode indium tin (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was sequentially ultrasonically cleaned with acetone and isopropyl alcohol, then stored in isopropanol, and then used. Subsequently, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Next, compound HI-1 was introduced into a cell of the vacuum deposition apparatus, and compound HT-1 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 first hole injection layer having a thickness of 10 nm. Next, compound HT-1 was introduced into a cell of the vacuum deposition apparatus and evaporated by passing an electric current through the cell, thereby forming a first hole transport layer having a thickness of 80 nm on the first hole injection layer. 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 materials described in Table 1 below were introduced into two cells of the vacuum deposition apparatus as hosts for the emissive layer, and compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, and the dopant material was evaporated simultaneously in a different ratio, and the mixture was deposited with 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. Next, compounds ET-1 and EI-1 were introduced into two other cells of the vacuum deposition apparatus and evaporated in a 1:1 ratio to form an electron transport layer with a thickness of 35 nm on the emissive layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer using a separate vacuum deposition apparatus. In this way, an OLED was manufactured.

[0097] [Comparative Example 1] Preparation of an OLED containing a conventional compound as a host. An OLED was fabricated in the same manner as in Device Example 1, except that compound C-8 was used alone as the host for the light-emitting layer.

[0098] As described above, the driving voltage, luminous efficiency, and luminous color of the organic electroluminescent devices manufactured in Device Example 1 and Comparative Example 1 were measured at a brightness of 1,000 nits, and the time required for the luminescence to decrease from 100% to 95% (lifetime; T95) at a brightness of 5,000 nits. The results are shown in Table 1 below.

[0099] [Table 6]

[0100] Referring to Table 1 above, by including specific combinations of the compounds according to this disclosure as the host material, it is possible to provide an organic electroluminescent device having higher luminescence efficiency and significantly improved lifetime characteristics compared to an organic electroluminescent device containing a single host material.

[0101] The compounds used in the above-mentioned Device Example 1 and Comparative Example 1 are shown in Table 2 below.

[0102] [Table 7]

Claims

1. A plurality of host materials, including a first host material and a second host material, The first host material is given by the following formula 1: 【Chemistry 1】 (In the formula, L １ This represents a single bond, substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene; Ar １ This represents substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl; R １ ~R ８ Each is 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 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 of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C2-C30) alkenyl Represents a mino, a substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, a substituted or unsubstituted mono- or di- (C6-C30) arylamino, a substituted or unsubstituted mono- or di- (3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl (3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl (3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl (3-30 member) heteroarylamino; or may be bonded to an adjacent substituent to form a ring. However, if Ar 1 is a deuterium-substituted phenyl, then R 6 is hydrogen, deuterium, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted quaterphenyl. It includes compounds represented by, The second host material is given by the following equation 2: 【Chemistry 2】 (In the formula, X ２１ and Y ２１ These are independently -N= and -NR ２５ -, -O-, or -S- However, X ２１ and Y ２１ one of which is -N=, and the other of X ２１ and Y 21 is -NR ２５ -, -O- or -S- provided that; R ２１ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl; R ２２ ~R ２５ Each of these independently comprises 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 condensed ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted Represents a substituted mono- or di-(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30) alkyl(C2-C30) alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted mono- or di-(3-30 member) heteroarylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted (C2-C30) alkenyl(C6-C30) arylamino, a substituted or unsubstituted (C2-C30) alkenyl(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; or may be bonded to an adjacent substituent to form a ring; However, R ２２ ~R ２４ At least one of them is -L ２１ -Ar ２１ Provided that; L ２１ represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar ２１ This includes substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryls, substituted or unsubstituted (3-30 member) heteroaryls, or -NR ３１ R ３２ It represents; R ３１ and R ３２ Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; e and f each independently represent an integer of 1 or 2, and g represents an integer from 1 to 4; and If e to g are integers greater than or equal to 2, then R ２２ Each of the following, R ２３ Each of and R ２４ (Each of these may be the same or different.) Multiple host materials containing compounds represented by [the specified formula / method].

2. The above formula 1 is the following formula 1-1 or 1-2: 【Transformation 3】 (In the formula, L １ and Ar １ This is as defined in claim 1; L ２ and L ３ Each of these independently represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar ２ and Ar ３ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, a substituted or unsubstituted di(C6-C30) arylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino; a and b each independently represent an integer of 1 or 2; and If a and b are integers of 2, Ar ２ Each of and Ar ３ (Each of these may be the same or different.) The host material according to claim 1, as represented by...

3. L １ This represents a single bond; Ar １ This represents pyridyl substituted with deuterium or (C6-C30) aryl; L ２ and L ３ Each of these independently represents a single bond, a substituted or unsubstituted phenylene; Ar ２ and Ar ３ Each of these independently represents an unsubstituted or deuterium-substituted (C6-C30)aryl (C6-C30) aryl; and The host material according to claim 2, wherein a and b each independently represent an integer of 1 or 2.

4. The above equation 2 is the following equations 2-1 to 2-3: 【Chemistry 4】 (In the formula, X ２１ , Y ２１ , L ２１ Ar ２１ , R ２１ ~R ２４ e, f, and g are as defined in claim 1; g' represents an integer from 1 to 3; and If g' represents an integer greater than or equal to 2, then R ２４ (Each of these may be the same or different.) The host material according to claim 1, represented by any one of the following.

5. Ar ２１ This includes substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenantrenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted fluoranteyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentan-fluoren]yl, substituted or unsubstituted spiro[dihydroindene-fluoren]yl, substituted or unsubstituted spiro[benzofluoren-fluoren]yl, substituted or The host material according to claim 1, wherein ' or represents an amino acid substituted with at least one selected from the group consisting of unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzocarbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzonaphthofuranil, substituted or unsubstituted dibenzofuranil, substituted or unsubstituted benzonaphthofuranil; or an amino acid substituted with at least one selected from the group consisting of phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terfphenyl, m-terphenyl, p-terphenyl, fluorenyl, benzofluorenyl, phenantrenyl, dibenzothiophenyl, benzonaphthofuranil, and dibenzofuranil.

6. The compound represented by formula 1 is the following compound: 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 A plurality of host materials according to claim 1, selected from the following.

7. The compound represented by formula 2 is the following compound: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 A host material according to claim 1, 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 the at least one light-emitting layer comprises a plurality of host materials as described in claim 1.

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