Organic electroluminescent compounds and organic electroluminescent devices containing the same

Abstract

To provide an organic electroluminescent compound that achieves improvement in luminous efficiency, drive voltage and / or life properties, and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure provides an organic electroluminescent compound represented by the following formula (1) (where L1 and L2 independently represent a single bond, substituted / unsubstituted (C6-C30) arylene or the like, Ar1 is substituted / unsubstituted (C6-C30) aryl or substituted / unsubstituted (5-30 membered) heteroaryl, Ar2 is a specific heterocyclic group).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same. [Background technology]

[0002] Small molecule green organic electroluminescent devices (OLEDs) were first developed by Tang et al. at Eastman Kodak in 1987 by using a TPD / ALq3 bilayer consisting of an emissive layer and a charge transport layer. Since then, the development of OLEDs has progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel packaging. For long-term use and high resolution of displays, low driving voltage and high luminous efficiency are required.

[0003] In order to improve the luminous efficiency, driving voltage and / or lifespan characteristics, various materials or concepts have been proposed for the organic layers of organic electroluminescent devices, but these have not been sufficient for practical use. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Application Publication No. 2018-0099510 [Patent Document 2] Korean Patent Application Publication No. 2018-0012709 Summary of the Invention [Problem to be solved by the invention]

[0005] The object of the present disclosure is to provide an organic electroluminescent compound that is effective for fabricating an organic electroluminescent device having improved driving voltage, life characteristics and / or power efficiency. Another object of the present disclosure is to provide an organic electroluminescent device comprising the organic electroluminescent compound. [Means for solving the problem]

[0006] The present inventors have discovered that the above object can be achieved by the synthesis of a compound of the following formula 1: [ka] (In the formula, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (5 to 30 membered) heteroaryl; Ar2 is a group represented by the following formula 1-1 or 1-2: [ka] represents R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl, or may be bonded to L2; X is O, S or NR 11 represents R 11 represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, or may be bonded to L2; and a, b, d, h, and i each independently represent an integer of 1 to 4, c represents an integer of 1 to 5, e and f each independently represent an integer of 1 to 3, and g represents an integer of 1 or 2, and when a to i are integers of 2 or greater, each of R1 to R9 may be the same or different. It has been found that this can be achieved by an organic electroluminescent compound represented by the formula:

[0007] Additionally, the present disclosure provides an organic electroluminescent device including a first electrode, a second electrode, and a plurality of organic layers including an emissive layer between the first electrode and the second electrode, wherein at least two of the organic layers are represented by the following formulas 3-1 and 3-2: [ka] (In the formula, R3' to R9' each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C60) aryl, substituted or unsubstituted (3 to 60-membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, a fused ring group of a substituted or unsubstituted (C3 to C30) aliphatic ring and a substituted or unsubstituted (C6 to C30) aromatic ring, substituted or unsubstituted (C2 to C30) alkenyl, substituted or unsubstituted (C2 to C30) alkynyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted (C6 to C30) aryloxy, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted mono- or di-(C2 to C30) alkoxy. or may be bonded to adjacent substituents to form a ring; X' is O, S or NR 11 ', R 11 '-L 11 represents -Ar3, L 11 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene; Ar3 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C60) arylamino, substituted or unsubstituted mono- or di-(3-60 membered) heteroarylamino, or substituted or unsubstituted (C6-C60) aryl(3-60 membered) heteroarylamino; and c' represents an integer of 1 to 5, d', h', and i' each independently represent an integer of 1 to 4, e' and f' each independently represent an integer of 1 to 3, and g' represents an integer of 1 or 2, and when c' to i' are integers of 2 or greater, each of R3' to R9' may be the same or different. The present invention provides an organic electroluminescent device comprising one or more compounds represented by

[0008] Advantageous Effects of the Invention By using the organic electroluminescent compounds of the present disclosure, it is possible to fabricate organic electroluminescent devices with improved driving voltage, lifetime characteristics and / or power efficiency. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present disclosure will be described in detail below. However, the following description is intended to illustrate the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0010] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device. If necessary, the organic electroluminescent compound can be included in any layer that constitutes the organic electroluminescent device.

[0011] The term "organic electroluminescent material" in the present disclosure refers to a material that can be used in an organic electroluminescent device and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, an emitting auxiliary material, an electron blocking material, an emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron transport auxiliary material, an electron injection material, etc.

[0012] The organic electroluminescent material of the present disclosure may include at least one compound represented by Formula 1. The compound represented by Formula 1 may be included in, but is not limited to, a hole injection layer, a hole transport layer, a hole auxiliary layer, an emission auxiliary layer, an electron blocking layer, an emission layer (including a host and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, preferably an emission layer, an electron transport layer, and / or an electron transport auxiliary layer. When included in the emission layer, the compound represented by Formula 1 may be included as a host material or a dopant material, and the host material may be a host material for a blue, green, or red light-emitting organic electroluminescent device. Furthermore, when included in the electron transport layer, the compound represented by Formula 1 may be included as an electron transport material. In addition, when included in the electron transport auxiliary layer, the compound represented by Formula 1 may be included as an electron transport auxiliary material.

[0013] As used herein, the term "(C1-C30) alkyl" refers to a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 20, and more preferably 1 to 10 carbon atoms. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and the like. The term "(C2-C30) alkenyl" refers to a straight-chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably 2 to 20, and more preferably 2 to 10 carbon atoms. The alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30)alkynyl" refers to a straight-chain or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which case the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, in which case the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered)heterocycloalkyl" refers to a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. The term "(C6-C30)aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, in which case the number of ring skeletal carbon atoms is preferably 6 to 25, more preferably 6 to 18. The aryl(ene) may be partially saturated and may include a spiro structure. The aryl may include phenyl,These may include biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azulenyl, and the like. More specifically, the above aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]phenanthryl, ]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl Phenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-quaterphenyl menyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-t-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl,9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl 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 Methyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo [b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, and the like.

[0014] The term "(3- to 30-membered) heteroaryl or (3- to 60-membered) heteroaryl" means an aryl having 3 to 30 or 3 to 60 skeletal ring atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The heteroaryl may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may include a spiro structure. The heteroaryls mentioned above include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzimidazolyl, and the like. and fused-ring heteroaryls such as aryl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, the heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 2-imidazopyridinyl,3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 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-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazo 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-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl yl, 9-phenanthridinyl, 10-phenanthridinyl, 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-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl,3-methylpyrrol-5-yl, 2-t-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 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]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2 -naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-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]-benzothio Phenyl, 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] 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, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, and the like. Additionally, "halogen" includes F, Cl, Br, and I.

[0015] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that respectively indicate the relative positions of substituents. Ortho indicates that two substituents are adjacent to each other; for example, when two substituents in a benzene derivative occupy the 1st and 2nd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions; for example, when two substituents in a benzene derivative occupy the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions; for example, when two substituents in a benzene derivative occupy the 1st and 4th positions, it is called the para position.

[0016] As used herein, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group, i.e., a substituent. In the formulae of the present disclosure, substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted aliphatic ring, substituted aromatic ring, substituted alkenyl, substituted alkynyl, substituted alkoxy, substituted aryloxy, substituted mono- or di-alkylamino, substituted mono- or di-alkenylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroaryl Substituents of amino, substituted alkenylarylamino, substituted alkenylheteroarylamino and substituted arylheteroarylamino are each independently selected from deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (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) hexachlorophenyl, ... Heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (3-30 membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and (3-30 membered)heteroaryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C3 0) arylsilyl, amino, mono- or di-(C1-C30)alkylamino, mono- or di-(C2-C30)alkenylamino, mono- or di-(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino, (C1-C30)alkyl(C2-C30)alkenylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkyl(3- to 30-membered)heteroarylamino, (C2-C30)alkenyl(C6-C30)arylamino,and (C-C) alkyl(C-C)aryl(C-C)alkyl(C-C)aryl, wherein the substituents may be substituted with deuterium instead of hydrogen at optional positions. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of (C-C) alkyl and (C-C) aryl. Specifically, the substituents may each independently be at least one selected from the group consisting of methyl and naphthyl.

[0017] In the formula of the present disclosure, when a substituent combines with an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted monocyclic or polycyclic (3 to 30 membered) alicyclic ring or aromatic ring, or a combination thereof, formed by combining two or more adjacent substituents. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 20. According to another embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 15.

[0018] In the formulas of the present disclosure, heteroaryl(ene)s may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl. and substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0019] Compounds represented by formula 1 are described in further detail below.

[0020] According to one embodiment of the present disclosure, the compound represented by Formula 1 is represented by the following Formulas 2-1 to 2-9: [ka] [ka] [ka] (In the formula, Ar1, R1 to R9, L1, L2, X, and a to i are as defined in Formula 1. It can be represented by any one of:

[0021] In Formula 1, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 and L2 each independently represent a single bond or a substituted or unsubstituted (C6-C15) arylene. According to another embodiment of the present disclosure, L1 and L2 each independently represent a single bond or an unsubstituted (C6-C15) arylene. Specifically, L1 and L2 each independently may represent a single bond, phenylene, etc.

[0022] In Formula 1, Ar1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar1 represents a substituted or unsubstituted (C6-C12) aryl. According to another embodiment of the present disclosure, Ar1 represents an unsubstituted (C6-C12) aryl. Specifically, Ar1 may represent phenyl, naphthyl, etc.

[0023] In Formula 1, R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl. According to one embodiment of the present disclosure, R1 and R2 each independently represent hydrogen.

[0024] In Formulas 1-1 and 1-2, R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl, or may be bonded to L2. According to one embodiment of the present disclosure, R3 to R9 each independently represent hydrogen or may be bonded to L2.

[0025] In formulas 1-1 and 1-2, X is O, S, or NR 11 Represents.

[0026] As used herein, R 11represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, or may be bonded to L2.

[0027] In formulas 1, 1-1, and 1-2, a, b, d, h, and i each independently represent an integer of 1 to 4, c represents an integer of 1 to 5, e and f each independently represent an integer of 1 to 3, and g represents an integer of 1 to 2, where when a to i are integers of 2 or greater, each of R1 to R9 may be the same or different.

[0028] The compound represented by Formula 1 can be, but is not limited to, one selected from the following compounds: [ka]

[0029] The compounds represented by formula 1 according to the present disclosure can be produced by synthetic methods known to those skilled in the art, for example, but not limited to, the following reaction schemes 1 to 4. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka] [Reaction Scheme 4] [ka]

[0030] In Reaction Schemes 1 to 4, L1, L2, Ar1, R1 to R9, X, and ai are as defined in Formula 1, Formula 1-1, and Formula 1-2.

[0031] Illustrative synthetic examples of compounds represented by Formula 1 are described above, but one skilled in the art will readily appreciate that all of these are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, and the like, and that the above reactions will proceed even when substituents defined in Formula 1 above but not specified in the particular synthetic example are attached.

[0032] The present disclosure provides an organic electroluminescent material and an organic electroluminescent device comprising the organic electroluminescent material, which comprises a compound represented by Formula 1. The organic electroluminescent material may consist solely of the compound according to the present disclosure, or may further comprise conventional materials contained in organic electroluminescent materials.

[0033] If necessary, the organic electroluminescent compound of Formula 1 of the present disclosure can be used as a co-host material. That is, the light-emitting layer can further include an organic electroluminescent compound other than the organic electroluminescent compound (first host material) represented by Formula 1 of the present disclosure as a second host material. In this case, the weight ratio between the first host material and the second host material is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70:30. The first host material and the second host material can be combined in a desired ratio by placing them in a shaker and then mixing them, placing them in a glass tube and melting them by heating, and then collecting the resulting mixture, or dissolving them in a solvent. When two or more materials are included in one layer, mixed deposition can be performed to form the layer, or co-deposition can be performed simultaneously and separately to form the layers.

[0034] The dopant contained in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, and preferably a fluorescent dopant.The fluorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited.

[0035] The organic electroluminescent device according to the present disclosure may include a first electrode, a second electrode, and a plurality of organic layers, including an emitting layer, between the first electrode and the second electrode. The organic layers may include an emitting layer, an emitting auxiliary layer between the emitting layer and the first electrode, a hole transport layer between the emitting auxiliary layer and the first electrode, an electron transport auxiliary layer between the emitting layer and the second electrode, and an electron transport layer between the electron transport auxiliary layer and the second electrode. At least two of the organic layers may be represented by the following formulas 3-1 and 3-2: [ka] (In the formula, R3' to R9' each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C60) aryl, substituted or unsubstituted (3 to 60-membered) heteroaryl, substituted or unsubstituted (C3 to C30) cycloalkyl, a fused ring group of a substituted or unsubstituted (C3 to C30) aliphatic ring and a substituted or unsubstituted (C6 to C30) aromatic ring, substituted or unsubstituted (C2 to C30) alkenyl, substituted or unsubstituted (C2 to C30) alkynyl, substituted or unsubstituted (C1 to C30) alkoxy, substituted or unsubstituted (C6 to C30) aryloxy, substituted or unsubstituted mono- or di-(C1 to C30) alkylamino, substituted or unsubstituted mono- or di-(C2 to C30) alkoxy. or may be bonded to adjacent substituents to form a ring; X' is O, S or NR 11 ', R 11 '-L 11 represents -Ar3, L 11 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene; Ar3 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C60) arylamino, substituted or unsubstituted mono- or di-(3-60 membered) heteroarylamino, or substituted or unsubstituted (C6-C60) aryl(3-60 membered) heteroarylamino; and c' represents an integer of 1 to 5, d', h', and i' each independently represent an integer of 1 to 4, e' and f' each independently represent an integer of 1 to 3, and g' represents an integer of 1 or 2, and when c' to i' are integers of 2 or greater, each of R3' to R9' may be the same or different. The composition may include one or more compounds represented by

[0036] According to one embodiment of the present disclosure, the compound represented by formula 3-1 or 3-2 may be included in at least the light-emitting layer.

[0037] Additionally, according to one embodiment of the present disclosure, the compound represented by Formula 3-1 or 3-2 may be included in at least one of the organic layers between the first electrode and the light-emitting layer. For example, the compound may be included in one or more of the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer (including a host and a dopant), electron buffer layer, hole blocking layer, electron transport layer, electron transport auxiliary layer, and electron injection layer, preferably one or more of the hole transport layer, electron transport layer, and electron transport auxiliary layer, but is not limited thereto.

[0038] According to one embodiment of the present disclosure, the compounds represented by Formula 3-1 or 3-2 may be contained, individually or together, in at least two of the following layers of an organic electroluminescent device: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, and a light-emitting layer (including a host and a dopant); or may be contained, individually or together, in at least two of the following layers: a light-emitting layer (including a host and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, and a electron injection layer.

[0039] The compounds represented by formula 3-1 or 3-2 of the present disclosure can be prepared by synthetic methods known to those skilled in the art, for example, but not limited to, the methods disclosed in (Patent Document 1) (published September 5, 2018) and (Patent Document 2) (published February 6, 2018).

[0040] In certain embodiments, the compound of formula 3-1 or 3-2 contained in at least one organic layer is represented by formula 1: [ka] (In the formula, L1 and L2 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene; Ar1 represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (5 to 30 membered) heteroaryl; Ar2 represents the following formula 1-1 or 1-2: and the compound of formula 3-1 or 3-2 contained in at least another organic layer is represented by formula 4: [ka] (In the formula, Ar 21 ~Ar 23 At least one of each independently represents the following formula 1-1 or 1-2, and Ar 21 ~Ar 23 and the others each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl; L 21 ~L 23 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene. is represented by [ka] R1 and R2 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; R3 to R9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl, or may be bonded to L2, or may be bonded to L 21 ~L 23 may also be coupled to one or more of X is O, S or NR 11 represents R 11 represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, or may be bonded to L2, or L 21 ~L 23 and a, b, d, h, and i each independently represent an integer of 1 to 4, c represents an integer of 1 to 5, e and f each independently represent an integer of 1 to 3, and g represents an integer of 1 or 2, where when a to i are integers of 2 or greater, each of R1 to R9 may be the same or different.

[0041] According to one embodiment of the present disclosure, in Formula 4, Ar 21 ~Ar 23 At least one of each independently represents formula 1-1 or 1-2, and Ar 21 ~Ar 23 and the others each independently represent a substituted or unsubstituted (C6-C20) aryl or a substituted or unsubstituted (5-15 membered) heteroaryl. 21 ~Ar 23 At least one of each independently represents formula 1-1 or 1-2, and Ar 21 ~Ar 23The others each independently represent unsubstituted or (C1-C6) alkyl and / or (C6-C12) aryl-substituted (C6-C20) aryl or unsubstituted (5-15 membered) heteroaryl. Specifically, Ar 21 ~Ar 23 may each independently represent formula 1-1 or 1-2, and Ar 21 ~Ar 23 and the others may each independently represent phenyl, naphthyl, biphenyl, naphthylphenyl, dimethylfluorenyl, dibenzofuranyl, and the like.

[0042] According to one embodiment of the present disclosure, in Formula 4, L 21 ~L 23 each independently represents a single bond or a substituted or unsubstituted (C6-C15) arylene. 21 ~L 23 Each of L independently represents a single bond or an unsubstituted (C6 to C15) arylene. 21 ~L 23 may each independently represent a single bond, phenylene, biphenylene, or the like.

[0043] The compound represented by formula 4 can be, but is not limited to, one selected from the following compounds: [ka] [ka]

[0044] The compound represented by formula 4 of the present disclosure can be produced by synthetic methods known to those skilled in the art, for example, but not limited to, the following reaction schemes 5 to 8. [Reaction Scheme 5] [ka] [Reaction Scheme 6] [ka] [Reaction Scheme 7] [ka] [Reaction Scheme 8] [ka]

[0045] In reaction schemes 5-8, Ar 22 , Ar 23 , L 21 ~L 23 , R3 to R9, X, and c to i are as defined in formula 4, formula 1-1, and formula 1-2.

[0046] Illustrative synthetic examples of compounds represented by formula 4 are described above, but one skilled in the art will readily appreciate that all of these are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclodehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, and the like, and that the above reactions will proceed even when substituents defined in formula 4 above but not specified in the particular synthetic example are attached.

[0047] The compound represented by formula 1 can be, but is not limited to, one selected from compounds 1-1 to 1-16.

[0048] In the organic electroluminescent device according to the present disclosure, the first electrode and the second electrode can be formed using a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. The organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a dual-side emitting type depending on the type of materials used to form the first electrode and the second electrode. In addition, the hole injection layer can be further doped with a p-type dopant, and the electron injection layer can be further doped with an n-type dopant.

[0049] In the organic electroluminescent device of the present disclosure, the organic layer can further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.In addition, in the organic electroluminescent device of the present disclosure, the organic layer can further comprise at least one metal selected from the group consisting of group 1 metals, group 2 metals, group 4 transition metals, group 5 transition metals, lanthanides of d-transition elements in the periodic table, and organometallic or at least one complex compound containing said metals.

[0050] The organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer that contains the blue, red or green light-emitting compound known in the art in addition to the organic electroluminescent compound of the present disclosure.In addition, it can further comprise a yellow or orange light-emitting layer as needed.

[0051] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") may be preferably disposed on the inner surface of one or both electrodes. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. The surface layer may provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc., metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0052] A hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, may be used between the anode and the light-emitting layer. The hole injection layer may be a multilayer to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, and in this case, each of the multilayers may simultaneously use two compounds. The hole transport layer or electron blocking layer may also be a multilayer.

[0053] Between the light-emitting layer and the cathode, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, or a combination thereof can be used. The electron buffer layer can be multi-layered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, and in this case, each of the multi-layered layers can use two compounds simultaneously. Also, the hole blocking layer or the electron transport layer can be multi-layered, and in this case, each of the multi-layered layers can use multiple compounds.

[0054] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or prevent electron overflow. When disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or prevent hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer and can be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. Furthermore, the electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer and can block electrons overflowing from the light-emitting layer and confine excitons in the light-emitting layer to prevent light leakage. When an organic electroluminescent device includes two or more hole transport layers, the additional hole transport layers can be used as hole auxiliary layers or electron blocking layers. The hole assisting layer and the electron blocking layer may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0055] In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant is preferably disposed on the surface of at least one of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, which facilitates the injection and transport of electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, which facilitates the injection and transport of holes from the mixed region into the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Using the reductive dopant layer as a charge generation layer, an organic electroluminescent device having two or more light-emitting layers that emit white light can be fabricated.

[0056] The organic electroluminescent material according to an embodiment of the present disclosure can be used as a light-emitting material for a white organic light-emitting device. It has been suggested that the white organic light-emitting device can have various structures, such as a parallel arrangement (parallel) method, a stacking method, or a color conversion material (CCM) method, depending on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light-emitting units. In addition, the organic electroluminescent material according to an embodiment of the present disclosure can also be applied to an organic electroluminescent device containing quantum dots (QDs).

[0057] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc. or wet film-forming methods such as spin coating, dip coating, flow coating, etc. can be used. The first and second host compounds of the present disclosure can be co-evaporated or mixed-evaporated to form a film.

[0058] When using a wet film-forming method, a thin film can be formed by dissolving or dispersing the materials forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited as long as the materials forming each layer are soluble or dispersible in a solvent that does not cause any problems in forming a film.

[0059] The organic electroluminescent devices of the present disclosure can be used to prepare display systems, such as display systems for smartphones, tablets, notebooks, PCs, TVs or automobiles, or lighting systems, such as outdoor or indoor lighting systems.

[0060] The invention of the present disclosure includes the following aspects 1 to 10. [Aspect 1] Formula 1 below: [ka] (In the formula, L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30-membered) heteroarylene; Ar 1 represents a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (5 to 30 membered) heteroaryl; Ar 2 is expressed by the following formula 1-1 or 1-2 [ka] represents R 1 and R 2 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; R 3 ~R 9 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl, or L 2 can be combined with X is O, S or NR 11 represents R 11 represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, or L 2 and a, b, d, h, and i each independently represent an integer of 1 to 4, c represents an integer of 1 to 5, e and f each independently represent an integer of 1 to 3, and g represents an integer of 1 or 2, where, when a to i are integers of 2 or greater, R 1 Each of ~R 9 may be the same or different) 1. An organic electroluminescent compound represented by the formula: [Aspect 2] Equation 1 is the following equations 2-1 to 2-9:

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[0061] Example 1: Preparation of Compounds 1-3 [ka] Synthesis of Compound 1-3-2 Compound 1-3-3 (10 g, 34.3 mmol), 1-bromo-4-iodobenzene (24.3 g, 85.8 mmol), copper(I) iodide (3.27 g, 17.2 mmol), ethylenediamine (2.06 g, 34.3 mmol), and potassium phosphate (21.9 g, 103 mmol) were dissolved in toluene (170 mL) in a flask, and the mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and distilled water was added to it. After extraction with ethyl acetate, the residue was dried over magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 1-3-2 (13.2 g, yield: 86.2%).

[0062] Synthesis of Compound 1-3-1 Compound 1-3-2 (13.2 g, 29.6 mmol), bis(pinacolato)diboron (9.76 g, 38.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (830 mg, 1.18 mmol), and potassium acetate (12.8 g, 130 mmol) were dissolved in 1,4-dioxane (295 mL) in a flask, and the mixture was refluxed at 120 °C for 24 hours. After the reaction was completed, the organic layer was separated with ethyl acetate, and the remaining water was removed with magnesium sulfate. The residue was separated by column chromatography to obtain compound 1-3-1 (9.4 g, yield: 64.4%).

[0063] Synthesis of compounds 1-3 Compound 1-3-1 (9.4 g, 19.1 mmol), compound A (6.35 g, 19.1 mmol), tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.953 mmol), and potassium carbonate (7.9 g, 57.2 mmol) were dissolved in toluene (78 mL), ethanol (23.5 mL), and water (23.5 mL) in a flask, and the mixture was refluxed at 120 °C for 24 hours. After the reaction was completed, the organic layer was separated with ethyl acetate, and the remaining water was removed with magnesium sulfate. The residue was separated by column chromatography to obtain compounds 1-3 (2.7 g, 4.36 mmol).

[0064] [Table 1]

[0065] Example 2: Preparation of Compound 2-2 [ka] Synthesis of Compound 2-2-1 Compound 1-3-3 (15.0 g, 51.5 mmol), 1-bromo-3-iodobenzene (29.3 g, 103 mmol), copper(I) iodide (4.9 g, 25.8 mmol), ethylenediamine (7.0 mL, 103 mmol), and potassium phosphate (27.5 g, 129 mmol) were dissolved in toluene (250 mL) in a flask, and the mixture was stirred under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and filtered through silica gel. The organic layer was concentrated and recrystallized from ethyl acetate to obtain compound 2-2-1 (14.2 g, yield: 62%).

[0066] Synthesis of compound 2-2 Compound 2-2-1 (5.0 g, 11.2 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (3.0 g, 12.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.5 g, 0.56 mmol), Esphos (0.46 g, 1.12 mmol), and sodium tert-butoxide (2.7 g, 28 mmol) were dissolved in toluene (60 mL) in a flask, and the mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, stirred at room temperature, and methanol was added. The resulting solid was filtered under reduced pressure and separated by column chromatography to obtain compound 2-2 (2.3 g, yield: 34%).

[0067] [Table 2]

[0068] Example 3: Preparation of Compound 2-3 [ka] Compound 2-2-1 (14.0 g, 31.4 mmol), N-phenyl-[1,1'-biphenyl]-3-amine (7.78 g, 31.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.44 g, 1.57 mmol), tri-tert-butylphosphine (635 mg, 3.14 mmol), and sodium tert-butoxide (6.04 g, 62.8 mmol) were dissolved in toluene (160 mL) in a flask, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure and separated by column chromatography to obtain compound 2-3 (14.6 g, yield: 76%).

[0069] [Table 3]

[0070] Device Example 1: Fabrication of an OLED Deposited with Organic Electroluminescent Compounds According to the Present Disclosure An OLED according to the present disclosure was fabricated. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone, ethanol, and distilled water, successively, and then stored in isopropanol. The ITO substrate was then attached to a substrate holder in a vacuum evaporation system. Compound HT was introduced into one cell of the vacuum evaporation system, and Compound HI was introduced into another cell of the vacuum evaporation system. The two materials were evaporated at different rates, and Compound HI was deposited with a doping amount of 3 wt. % based on the total amount of Compound HT and Compound HI to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Compound HT was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm. Compound HT was then deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm. After the hole injection layer and hole transport layer were formed, an emitting layer was formed thereon as follows. Compounds 1-3 were introduced into one cell of a vacuum evaporation system as hosts for the emissive layer, and compound BD was introduced into another cell. The two materials were evaporated at different rates and deposited at a doping amount of 2 wt% based on the total amount of host and dopant to form a 20 nm-thick emissive layer on the second hole-transporting layer. Compound ET-1 was then evaporated as a 5 nm-thick hole-blocking layer. In the other two cells, compounds ET-2 and EI-1 were evaporated in a 1:1 ratio (by weight) to form a 30 nm-thick electron-transporting layer on the hole-blocking layer. Compound EI-1 was then evaporated as a 2 nm-thick electron-injecting layer, followed by the deposition of an 80 nm-thick Al cathode using a separate vacuum evaporation system to fabricate OLEDs.

[0071] As a result, the driving voltage achieved at 1,000 nits brightness was 3.2 V, the power efficiency was 5.9 lm / W, and the shortest time it took for the brightness to decrease from 100% to 95% was 31.1 hours.

[0072] Comparative Example: Fabrication of OLEDs containing conventional compounds The OLED was fabricated in the same manner as Device Example 1, except that compound BH-2 was used as the host in the emissive layer.

[0073] As a result, the driving voltage achieved at 1,000 nits brightness was 4.1 V, the power efficiency was 5.9 lm / W, and the shortest time it took for the brightness to decrease from 100% to 95% was 14.6 hours.

[0074] As can be seen from the above results, it is confirmed that the OLED containing the organic electroluminescent compound according to the present disclosure as a host material can significantly reduce the driving voltage and significantly improve the life characteristics compared to the OLED using the conventional compound.

[0075] Device Example 2: Fabrication of an OLED Deposited with Organic Electroluminescent Compounds According to the Present Disclosure The OLED was fabricated in the same manner as Device Example 1, except that Compound 2-2 was used instead of Compound HT as the second hole-transporting material.

[0076] As a result, the driving voltage obtained at a brightness of 1,000 nits was 3.2 V, and the power efficiency was 6.9 lm / W.

[0077] Device Example 3: Fabrication of an OLED Deposited with Organic Electroluminescent Compounds According to the Present Disclosure The OLED was fabricated in the same manner as Device Example 1, except that Compound 2-3 was used instead of Compound HT as the second hole-transporting material.

[0078] As a result, the driving voltage obtained at a brightness of 1,000 nits was 3.2 V, and the power efficiency was 6.9 lm / W.

[0079] As can be seen from the above results, it is confirmed that the OLED comprising the organic electroluminescent compound according to the present disclosure as the second hole transport material and the host material can significantly reduce the driving voltage and significantly improve the power efficiency characteristics compared to the OLED using conventional compounds.High power efficiency in display implementation can represent a higher performance display by implementing the organic electroluminescent device with lower power consumption.

[0080] [Table 4]

Claims

1. Formula 2-4 below: 【Chemical 1】 (In the formula, L １ and L ２ each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (5 to 30 membered) heteroarylene; Ar １ represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl; R １ and R ２ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; R ３ R to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30) alkyl, substituted or unsubstituted (C6 to C30) aryl, or substituted or unsubstituted (5 to 30 membered) heteroaryl; a, b, and d each independently represent an integer of 1 to 4, c represents an integer of 1 to 5, and e represents an integer of 1 to 3, where, when a to e are integers of 2 or more, R １ Each of R to R5 may be the same or different.

1. An organic electroluminescent compound represented by the formula:

2. L １ , L ２ , R １ ~R5 and Ar １ The substituents of the substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl and the substituted heteroarylene in the formula (I) are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1 to C30) alkyl, halo(C1 to C30) alkyl, (C2 to C30) alkenyl, (C2 to C30) alkynyl, (C1 to C30) alkoxy, (C1 to C30) alkylthio, (C3 to C30) cycloalkyl, (C3 to C30) cycloalkenyl, (3 to 7 membered) heterocycloalkyl, ( (C6-C30)aryloxy, (C6-C30)arylthio, (3-30 membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl, (C6-C30)aryl unsubstituted or substituted with at least one of (C1-C30)alkyl and (3-30 membered)heteroaryl, 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-C 30) alkylamino, mono- or di-(C2-C30) alkenylamino, mono- or di-(C6-C30) arylamino, mono- or di-(3- to 30-membered) heteroarylamino, (C1-C30) alkyl(C2-C30) alkenylamino, (C1-C30) alkyl(C6-C30) arylamino, (C1-C30) alkyl(3- to 30-membered) heteroarylamino, (C2-C30) alkenyl(C6-C30) arylamino, (C2-C30) alkenyl(3- to 30-membered) heteroarylamino, (C6-C30) alkenyl 2. The organic electroluminescent compound according to claim 1, wherein the aryl(3-30 membered)heteroarylamino is at least one selected from the group consisting of (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di(C6-C30) arylboronyl, di(C1-C30) alkylboronyl, (C1-C30) alkyl(C6-C30) arylboronyl, (C6-C30) aryl(C1-C30) alkyl, and (C1-C30) alkyl(C6-C30) aryl.

3. The organic electroluminescent compound represented by formula 2-4 is the following compound: 【Chemistry 2】 2. The organic electroluminescent compound according to claim 1, selected from:

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