Organic electroluminescent compounds and organic electroluminescent devices containing the same

Abstract

The present invention provides organic electroluminescent compounds and organic electroluminescent devices containing the same. [Solution] This disclosure relates to an organic electroluminescent compound represented by Formula 1, as well as organic electroluminescent materials and organic electroluminescent devices containing the same. By including the compounds according to this disclosure, it is possible to provide organic electroluminescent devices having lower drive voltage, higher luminescence efficiency and / or improved lifetime characteristics compared to the prior art.

Description

[Technical Field]

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

[0002] The green-emitting TPD / Alq3 bilayer small molecule organic electroluminescent device (OLED), composed of an emissive layer and a charge transport layer, was first developed in 1987 by Tang et al. at Eastman Kodak. Since then, research on organic electroluminescent devices has progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs primarily use phosphorescent materials that offer excellent luminescence efficiency in panel mounting. High-luminescence OLEDs are required for long-term use and high resolution displays.

[0003] Patent Documents 1, 2, and 3 disclose fluorene derivatives or compounds containing an amino group, but do not specifically disclose the particular compound claimed in this disclosure. In addition, there is a continuous need to develop light-emitting materials that exhibit improved performance compared to previously disclosed compounds, such as improved drive voltage, luminous efficiency, and / or lifetime characteristics. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Chinese Patent Application Publication No. 117142962 Specification [Patent Document 2] Chinese Patent Application Publication No. 114773286 Specification [Patent Document 3] Chinese Patent Application Publication No. 116283865 Specification [Patent Document 4] Korean Patent Application Publication No. 2023-0034139 Specification [Patent Document 5] Korean Patent Application Publication No. 2021-0143521 Specification [Patent Document 6] Korean Patent Application Publication No. 2017-0022865 Specification [Patent Document 7] Korean Patent Application Publication No. 2018-0099487 Specification [Patent Document 8] Korean Patent Application Publication No. 2021-0124018 Specification [Patent Document 9] Korean Patent Application Publication No. 2021-0006283 Specification [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] An object of this disclosure is to provide an organic electroluminescent compound having a novel structure suitable for use in organic electroluminescent devices. Another object of this disclosure is to provide an organic electroluminescent material and an organic electroluminescent device exhibiting high luminescence efficiency and / or long lifetime characteristics. [Means for solving the problem]

[0006] As a result of intensive research to solve the technical challenges, the inventors have found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1 and an organic electroluminescent material or organic electroluminescent device containing the same. [ka]

[0007] In Equation 1, X is -O-, -S-, -Se-, -Ge- or -(CR9R 10 ) n - represents, Ring A represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, and the two adjacent carbon atoms in ring A are each represented by formula 1-A [ka] It is attached to the * position in the aliphatic ring, R1 to R4 each independently represent 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 (C3 to C30) cycloalkyl, substituted or unsubstituted (C1 to C30) alkoxy, 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, a substituted or unsubstituted condensed ring group of a (C3 to C30) aliphatic ring and a (C6 to C30) aromatic ring, or -LN(L1-Ar1)(L2-Ar2). R9 and R 10 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl, or R9 and R 10 They can be connected to each other to form a ring, R 11 and R 12 Each of these independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, and each R 11 or each R 12 They may be the same or different from each other. L, L1, and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. L is linked to at least one carbon atom selected from the group consisting of a carbon atom bonded to any one of R1 to R4 and a carbon atom of the benzene ring or naphthalene ring of ring A. Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl, n represents an integer of 1 or 2, m represents an integer of 1-3, and a represents an integer of 1 or 2, A hydrogen atom in the compound represented by Formula 1 may be substituted with deuterium, However, when Ring A is a substituted or unsubstituted benzene ring, L1, L2, Ar1, and Ar2 do not include an aryl condensed with a heteroaryl or a cycloalkyl.

[0008] In addition, the present inventors have found that the above object can be achieved by an organic electroluminescent device including a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and a hole transport band between the first electrode and the light-emitting layer, wherein the hole transport band includes a compound represented by Formula 1, and the light-emitting layer includes a compound represented by the following Formula 6 and a compound represented by the following Formula 7.

[0009]

Chemical formula

[0010] [ka] In Equation 7, X1 to X3 are each independently N or CR 21 This represents, where at least one of X1 to X3 is N. Each R 21 It independently represents hydrogen or deuterium. L 21 ~L 23 Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene, and Ar 21 ~Ar 23Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3-7 member) heterocycloalkyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. However, Ar 21 ~Ar 23 At least one of them is a substituted or unsubstituted (3-30 member) heteroaryl.

[0011] Advantageous effects of the invention The organic electroluminescent compounds according to this disclosure exhibit suitable performance for use in organic electroluminescent devices. In addition, by including the compounds according to this disclosure as organic electroluminescent materials, it is possible to provide organic electroluminescent devices that exhibit higher luminescence efficiency and / or improved lifetime characteristics compared to conventional organic electroluminescent devices, and to manufacture display devices or lighting devices using such devices. [Modes for carrying out the invention]

[0012] The following details the disclosure. However, the following description is intended to explain the disclosure and is not intended to limit its scope.

[0013] In this disclosure, “organic electroluminescent compound” refers to a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any material layer constituting the organic electroluminescent device.

[0014] In this disclosure, “organic electroluminescent material” refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may, if necessary, be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a charge generation material, an N-type charge generation material, a P-type charge generation material, a light emission auxiliary material, an electron blocking material, a light emission material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like.

[0015] In this specification, the term "(C1-C30) alkyl" refers to a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, preferably 1 to 20, more preferably 1 to 10 carbon atoms. The alkyls mentioned above may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, preferably 3 to 20, more preferably 3 to 7 carbon atoms. The cycloalkyls mentioned above may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, norbornyl, adamantyl, etc. In this disclosure, the term "(3-7 member) heterocycloalkyl" means a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent having 3 to 7, preferably 5 to 7, ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Se. The above heterocycloalkyls may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like.

[0016] In this disclosure, "(C6-C30)aryl" or "(C6-C30)arylene" refers to monocyclic or fused ring radicals derived from aromatic hydrocarbons having 6 to 30 carbon atoms in the cyclic skeleton, and may be partially saturated. The number of carbon atoms in the cyclic skeleton is preferably 6 to 20, more preferably 6 to 15. The aryl may include a spiro structure. The above aryls may 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, coumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azlenyl, tetramethyl-dihydrophenantrenyl, etc. 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, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4''-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl Phenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-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-Phenanthril, 2-Phenanthril, 3-Phenanthril, 4-Phenanthril, 9-Phenanthril, 1-Crysenyl, 2-Crysenyl, 3-Crysenyl, 4-Crysenyl, 5-Crysenyl, 6-Crysenyl, Benzo[c]Phenanthril, Benzo[g]Crysenyl, 1-Triphenylenyl, 2-Triphenylenyl, 3-Triphenylenyl, 4-Triphenylenyl, 3-Fluoranthenyl, 4-Fluoranthenyl, 8-Fluoranthenyl, 9-Fluoranthenyl Tenyl, 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 Fluorenzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl 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 Fluorenzo[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, 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,This may include 10-dihydro-4-phenantrenyl, etc.

[0017] In this disclosure, "(3-30 member) heteroaryl" or "(3-30 member) heteroarylene" refers to an aryl or arylene group having 3 to 30 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Se. In this specification, the number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20. The number of heteroatoms is preferably 1 to 4. The heteroaryl or heteroarylene may be a monocyclic ring or a fused ring fused with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl or heteroarylene may be formed by linking at least one heteroaryl group or aryl group to a heteroaryl group via a single bond, and may include a spiro structure. The above heteroaryls include monocyclic heteroaryls, such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, etc., and condensed cyclic heteroaryls, such as benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, benzofloquinolinil, benzofloquinazolinil, benzoflonaphthyridinil, benzoflopyrimidinil, naphthoflopyrimidinil, benzothienocinolinil, benzothienocinazolinil, benzothienonaphthyridinil Dinyl, benzothienopyrimidinyl, naphthienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzoflopyrazinyl, naphthoflopyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenantridinyl, benzodioxolyl,Indolidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenadinyl, imidazopyridinyl, clomenoquinazolyl, thioclomenoquinazolyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, heteroaryls may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-yl Indolidinyl, 7-Indolidinyl, 8-Indolidinyl, 2-Imidazopyridyl, 3-Imidazopyridyl, 5-Imidazopyridyl, 6-Imidazopyridyl, 7-Imidazopyridyl, 8-Imidazopyridyl, 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 Ryl, 2-furyl, 3-furyl, 2-benzofuranil, 3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4- Isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl,Azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridine, 2-phenanthridine, 3-phenanthridine, 4-phenanthridine, 6-phenanthridine, 7-phenanthridine, 8-phenanthridine, 9-phenanthridine, 10-phenanthridine, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl Enyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-tert-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert- Butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-be Nzofuranil, 6-naphtho-[1,2-b]-benzofuranil, 7-naphtho-[1,2-b]-benzofuranil, 8-naphtho-[1,2-b]-benzofuranil, 9-naphtho-[1,2-b]-benzofuranil, 10-naphtho-[1,2-b]-benzofuranil, 1-naphtho-[2,3-b]-benzofuranil, 2-naphtho-[2,3-b]-benzofuranil, 3-naphtho-[2,3-b]-benzofuranil, 4-naphtho-[2,3-b]-benzofuranil, 5-naphtho-[2,3-b]-benzofuranil, 6-naphtho-[2,3-b]-benzofuranil,7-Naphtho-[2,3-b]-benzofuranil, 8-Naphtho-[2,3-b]-benzofuranil, 9-Naphtho-[2,3-b]-benzofuranil, 10-Naphtho-[2,3-b]-benzofuranil, 1-Naphtho-[2,1-b]-benzofuranil, 2-Naphtho-[2,1-b]-benzofuranil, 3-Naphtho-[2,1-b]-benzofuranil, 4-Naphtho-[2,1-b]-benzofuranil, 5-Naphtho-[2,1-b]-benzofuranil, 6-Naphtho-[2,1-b]-benzofuranil, 7-Naphtho-[2,1-b]-benzofuranil, 8-Naphtho- [2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl, 8-naphtho-[1,2-b]-benzothiophenyl phenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl, 1-naphtho-[2,3-b]-benzothiophenyl, 2-naphtho-[2,3-b]-benzothiophenyl, 3-naphtho-[2,3-b]-benzothiophenyl, 4-naphtho-[2,3-b]-benzothiophenyl, 5-naphtho-[2,3-b]-benzothiophenyl, 1-naphtho-[2,1-b]-benzothiophenyl, 2-naphtho-[2,1-b]-benzothiophenyl, 3-naphtho-[2,1-b]-benzothiophenyl, 4-naph To-[2,1-b]-benzothiophenyl, 5-naphtho-[2,1-b]-benzothiophenyl, 6-naphtho-[2,1-b]-benzothiophenyl, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl,9-Benzoflo[3,2-d]pyrimidinyl, 2-Benzothio[3,2-d]pyrimidinyl, 6-Benzothio[3,2-d]pyrimidinyl, 7-Benzothio[3,2-d]pyrimidinyl, 8-Benzothio[3,2-d]pyrimidinyl, 9-Benzothio[3,2-d]pyrimidinyl, 2-Benzoflo[3,2-d]pyrazinyl, 6-Benzoflo[3,2-d]pyrazinyl, 7-Benzoflo[3,2-d]pyrazinyl, 8-Benzoflo[3,2-d]pyrazinyl, 9-Benzoflo[3,2-d]pyrazinyl, 2-Benzothio[3,2-d] This may include pyrazinyl, 6-benzothio[3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. In addition, "heteroaryl(len)" can be classified into heteroaryl(len) having electronic properties and heteroaryl(len) having hole properties. Heteroaryl(len) compounds with electronic properties are those whose parent nucleus is relatively electron-rich, such as substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, and substituted or unsubstituted quinolyl. Heteroaryl(len) compounds with hole properties are those whose parent nucleus is relatively electron-poor, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0018] In this specification, a "(C3-C30) aliphatic ring-(C6-C30) aromatic ring fused ring group" means a ring functional group formed by condensing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms, preferably 3 to 25, more preferably 3 to 18, with at least one aromatic ring having 6 to 30 ring skeleton carbon atoms, preferably 6 to 25, more preferably 6 to 18. Specific examples of fused ring groups include fused ring groups of one or more benzenes and one or more cyclohexanes, or fused ring groups of one or more naphthalenes and one or more cyclopentanes. In this specification, the carbon atoms of a (C3-C30) aliphatic ring-(C6-C30) aromatic ring fused ring group may be replaced by one or more heteroatoms selected from B, N, O, S, Si, P, and Se. In this specification, "halogen" includes F, Cl, Br, and I.

[0019] In addition, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are prefixes that indicate the relative positions of substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other; for example, if two substituents in a benzene derivative occupy positions 1 and 2, this is called an "ortho-" configuration. The prefix "meta-" indicates that two substituents are at positions 1 and 3; for example, if two substituents in a benzene derivative occupy positions 1 and 3, this is called a "meta-" configuration. The prefix "para-" indicates that two substituents are at positions 1 and 4; for example, if two substituents in a benzene derivative occupy positions 1 and 4, this is called a "para-" configuration.

[0020] In this specification, “a ring formed by linking adjacent substituents” means that at least two adjacent substituents are linked or condensed to form a substituted or unsubstituted monocyclic or polycyclic (3-30 member) alicyclic or aromatic ring, or a combination thereof. Preferably, the ring may be a substituted or unsubstituted monocyclic or polycyclic (5-25 member) alicyclic or aromatic ring, or a combination thereof. In addition, the ring may contain at least one heteroatom selected from B, N, O, S, Si, P, and Se. According to one embodiment of this disclosure, the number of carbon atoms in the ring skeleton is 5-20, and according to another embodiment of this disclosure, the number of carbon atoms in the ring skeleton is 5-15. For example, the fused ring may have a spiro structure, and may take the form of, for example, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofluorene ring, and so on.

[0021] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a given functional group is replaced by another atom or another functional group, i.e., a substituent, and this includes substitution by a group in which two or more substituents are linked. Unless otherwise specified, substituents may replace hydrogen at any position where the substituent can be substituted without limitation, and if two or more hydrogen atoms in a given functional group are each replaced by substituents, each substituent may be the same or different from one another. The maximum number of substituents that can be substituted for a given functional group may be the total number of valencies that can be substituted for each atom forming the functional group. In this specification, substituted alkyl, substituted aryl(ylene), substituted heteroaryl(ylene), substituted cycloalkyl(ylene), substituted heterocycloalkyl(ylene), substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted condensed ring groups of an aliphatic ring and an aromatic ring, substituted benzene ring, substituted naphthalene ring, substituted mono or dialkylamino, substituted mono or dialkenylamino, substituted alkylalkenylamino, substituted mono or diarylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, substituted mono or diheteroarylamino, and substituted arylheteroarylamino are each independently deuterium, halogen, cyano, and carboxymethyl ammonium compounds. Ruboxyl, 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, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio O, (3-30 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 group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, amino, mono or di(C1-C30) alkylamino,Substituted or unsubstituted mono or di(C6-C30) arylaminos, substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylaminos, substituted or unsubstituted mono or di(3-30 member) heteroarylaminos, substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylaminos, substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylaminos, (C1-C30) alkylcarbonyls, (C1-C30) alcoholic The group may be substituted with at least one selected from the group consisting of xycarbonyl, (C6-C30)arylcarbonyl, (C6-C30)arylphosphinyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl and combinations thereof. According to one embodiment of the present disclosure, the group consists of deuterium, halogen, (C1-C20)alkyl, (C3-C20)cycloalkyl, (C6-C25)aryl, (3-25 member)heteroaryl, mono or di(C6-C30)arylamino and combinations thereof. According to another embodiment of the present disclosure, the group consists of deuterium, halogens, (C1-C10) alkyl, (C6-C10) cycloalkyl, (C6-C18) aryl, (3-25 member) heteroaryl, mono or di(C6-C20) arylamino and combinations thereof. For example, the group may consist of deuterium, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, phenantrenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, triphenylenyl, diphenylamino, carbazolyl, cyclohexyl, norbornyl, or adamantyl, which may be further substituted with deuterium.

[0022] In this disclosure, if substituents are not shown in the chemical formula or compound structure, it may mean that all possible positions of substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, in which case the deuterium content may range from 0% to 100%. In this disclosure, if substituents are not shown in the chemical formula or compound structure, hydrogen and deuterium may be present in the compound unless substituents are explicitly excluded, such as 0% deuterium, 100% hydrogen, or all substituents being hydrogen. Deuterium is an isotope of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. It may be represented as hydrogen-2, and its element symbol is D or 2 It can also be written as H. Isotopes are atoms that have the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0023] In this disclosure, “these combinations” means a combination of one or more elements from the corresponding list to form known or chemically stable configurations that can be envisioned by those skilled in the art. For example, alkyl and deuterium may be combined to form partially or completely deuterated alkyl groups, halogen and alkyl may be combined to form alkyl halide substituents, and halogen, alkyl and aryl may be combined to form arylalkyl halides. For example, preferred combinations of substituents may include up to 50 atoms that are neither hydrogen nor deuterium, or up to 40 atoms that are neither hydrogen nor deuterium, or up to 30 atoms that are neither hydrogen nor deuterium, or often preferred combinations of substituents may include up to 20 atoms that are neither hydrogen nor deuterium.

[0024] In the formulas of this disclosure, if there are multiple substituents represented by the same symbol, each substituent represented by the same symbol may be the same as or different from one another.

[0025] The compound represented by formula 1 is described in more detail below.

[0026] In Equation 1, X is -O-, -S-, -Se-, -Ge-, or -(CR9R 10 ) n - represents. According to one embodiment of this disclosure, X is -(CR9R 10 ) n - represents

[0027] In Equation 1, R9 and R 10 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl, or R9 and R 10 These can be connected to each other to form a ring. According to one embodiment of the present disclosure, R9 and R 10 Each of these independently represents a substituted or unsubstituted (C1-C20) alkyl or a substituted or unsubstituted (C6-C20) aryl, or R9 and R 10 These can be linked together to form a spiro ring. According to another embodiment of the present disclosure, R9 and R 10 Each of these independently represents a substituted or unsubstituted (C1-C10) alkyl or a substituted or unsubstituted (C6-C18) aryl. For example, R9 and R 10 These can each be independently methyl, ethyl, or phenyl, and these can be substituted with deuterium. R9 and R 10 These may be the same as or different from each other. According to one embodiment of the present disclosure, R9 and R 10 They can be the same.

[0028] In Equation 1, n represents an integer of 1 or 2. According to one embodiment of the present disclosure, n is 1.

[0029] In Formula 1, ring A represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, and two adjacent carbon atoms in ring A are each bonded to the * position in Formula 1-A to form an aliphatic ring. According to one embodiment of the present disclosure, the benzene ring or naphthalene ring may be substituted with one or more of deuterium, phenyl, and -LN(L1-Ar1)(L2-Ar2), and two adjacent carbon atoms in the benzene ring or naphthalene ring may each be bonded to the * position in Formula 1-A to form a cyclohexane, cyclopentane, or cycloheptane ring.

[0030] In Formula 1, R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, or -LN(L1-Ar1)(L2-Ar2). According to one embodiment of the present disclosure, R1 to R4 each independently represent hydrogen, deuterium, 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 (C3 to C30) cycloalkyl, or -LN(L1-Ar1)(L2-Ar2). According to another embodiment of the present disclosure, R1 to R4 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6 to C30) aryl, or -LN(L1-Ar1)(L2-Ar2). For example, R1 to R4 each independently represent hydrogen, deuterium, or -LN(L1-Ar1)(L2-Ar2).

[0031] In equation 1-A, R 11 and R12 Each of these independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, and each R 11 or each R 12 These may be the same as or different from each other. According to one embodiment of the present disclosure, R 11 and R 12 Each of these independently represents either hydrogen or deuterium.

[0032] In equation 1-A, m represents an integer between 1 and 3.

[0033] In Formula 1, L, L1, and L2 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of the present disclosure, L, L1, and L2 each independently represent a single bond or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L, L1, and L2 each independently represent a single bond or a substituted or unsubstituted (C6-C18) arylene. Hereinafter, arylenes, heteroarylenes, or cycloalkylenes may be substituted with one or more deuterium, (C1-C30) alkyls, and (C6-C30) aryls, which may be further substituted with deuterium. For example, L can be a single bond, and L1 and L2 can independently be a single bond, unsubstituted or phenyl-substituted phenylene, biphenyl, dimethylfluorenylene, etc., which can be further substituted with deuterium.

[0034] In Formula 1, L is linked to at least one carbon atom selected from the group consisting of a carbon atom bonded to any one of R1 to R4 and a carbon atom of the benzene ring or naphthalene ring of ring A. According to one embodiment of the present disclosure, L is linked to at least one carbon atom bonded to any one of R1 to R4 and / or a carbon atom selected from the group consisting of the benzene ring or naphthalene ring of ring A. For example, L may be linked to a carbon atom bonded to R2, R3, or R4 and / or a benzene ring of ring A.

[0035] In Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (C6-C25) cycloalkyl. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (C6-C10) cycloalkyl. In this specification, aryl, heteroaryl, or cycloalkyl can be substituted with at least one selected from the group consisting of deuterium, (C1-C30) alkyl, (C6-C30) aryl, and (C3-C30) cycloalkyl. For example, Ar1 and Ar2 may each independently be substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, quaterphenyl, dimethylfluorenyl, diphenylfluorenyl, cyclohexyl, norbornyl, adamantyl, etc., which may be further substituted with deuterium. Phenyl may be substituted with one or more of deuterium, methyl, tert-butyl, norbornyl, adamantyl, and cyclohexyl. According to one embodiment of the present disclosure, at least one of Ar1 and Ar2 comprises a (C6-C30) aryl substituted with a (C1-C30) alkyl or (C3-C30) cycloalkyl, preferably at least one of Ar1 and Ar2 may comprise a (C6-C30) aryl substituted with methyl, tert-butyl, norbornyl, adamantyl, or cyclohexyl.

[0036] In Equation 1, a represents an integer of 1 or 2. Hydrogen atoms in the compounds represented by Equation 1 may be substituted with deuterium.

[0037] In Formula 1, when ring A is a substituted or unsubstituted benzene ring, L1, L2, Ar1, and Ar2 do not contain heteroaryl or aryl condensed with a cycloalkyl group. According to one embodiment of the present disclosure, when ring A is a substituted or unsubstituted benzene ring, L1, L2, Ar1, and Ar2 do not contain (3-30 member) heteroaryl or (C6-C30) aryl condensed with a (C3-C30) cycloalkyl group. For example, aryl condensed with a cycloalkyl group is [ka] These are possible.

[0038] Equation 1 can be expressed by any one of the following equations 2-1 to 2-4. [ka]

[0039] In equations 2-1 to 2-4, one pair selected from R5 and R6, R6 and R7, and R7 and R8 is linked to the * position in equation 1-A, or one pair selected from R'1 and R'2, R'2 and R'3, and R'3 and R'4 is linked to the * position in equation 1-A, and X, R1 to R4, L, L1, L2, Ar1 and Ar2 are as defined in equation 1, and R5 to R8 and R'1 to R'4, which are not linked to equation 1-A, are each independently the same as those defined for R1.

[0040] According to one embodiment of the present disclosure, in formulas 2-1 to 2-4, L may be bonded to one or more carbon atoms of R1 to R8 and R'1 to R'4. For example, L may be bonded to one or more carbon atoms of R2, R3, R4 and R5.

[0041] Equation 1 can be expressed by any one of the following equations 3-1 to 3-4. [ka]

[0042] In equations 3-1 to 3-4, X, R1 to R4, L, L1, L2, Ar1 and Ar2 are as defined in equation 1, and R5 to R8, R'1 and R'4 are the same as those independently defined for R1.

[0043] According to one embodiment of the present disclosure, in formulas 3-1 to 3-4, L may be bonded to one or more carbon atoms of R1 to R8, R'1 and R'4. For example, L may be bonded to one or more carbon atoms of R2, R3, R4 and R5.

[0044] Equation 1 can be expressed by any one of the following equations 4-1 to 4-4. [ka]

[0045] In equations 4-1 to 4-4, X, R1 to R4, L, L1, L2, Ar1 and Ar2 are as defined in equation 1, and R5 to R8, R'1 and R'4 are the same as those independently defined for R1.

[0046] According to one embodiment of the present disclosure, in formulas 4-1 to 4-4, L may be bonded to one or more carbon atoms of R1 to R8, R'1, and R'4. For example, L may be bonded to one or more carbon atoms of R2 and R5.

[0047] Equation 1 can be expressed by one of the following equations 5-1 to 5-4. [ka]

[0048] In equations 5-1 to 5-4, X, R1 to R4, L, L1, L2, Ar1 and Ar2 are as defined in equation 1, and R5 to R8, R'1 and R'4 are the same as those independently defined for R1.

[0049] According to one embodiment of the present disclosure, in formulas 5-1 to 5-4, L may be bonded to one or more carbon atoms of R1 to R8, R'1, and R'4. For example, L may be bonded to one or more carbon atoms of R2 and R5.

[0050] The compound represented by formula 1 is selected from, but is not limited to, the following compounds.

[0051] The organic electroluminescent compound represented by Formula 1 may be at least one selected from the following compounds, but is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0052] The compounds represented by Formula 1 according to this disclosure can be produced by synthetic methods known to those skilled in the art. For example, the compounds of this disclosure can be synthesized by referring to (Patent Document 4) (March 9, 2023) and (Patent Document 5) (November 29, 2021), but are not limited thereto.

[0053] The following describes organic electroluminescent devices using the organic electroluminescent compounds mentioned above.

[0054] An organic electroluminescent device according to one embodiment of the present disclosure comprises a first electrode, a second electrode, and one or more organic layers located between the first electrode and the second electrode, the organic layers comprising a hole transport layer, an emissive layer, a hole auxiliary layer, an electron blocking layer, and an emissive layer. According to one example, at least one of the hole transport layer, emissive layer, hole auxiliary layer, electron blocking layer, and emissive layer may comprise an organic electroluminescent compound represented by formula 1. For example, the hole transport layer may comprise an organic electroluminescent compound represented by formula 1. According to one example, the organic electroluminescent material of the present disclosure may comprise at least one compound from compounds C-1 to C-940, and the organic electroluminescent material may comprise the same organic layer, for example, the hole transport layer.

[0055] An example light-emitting layer may comprise a first host compound and a second host compound, where the weight ratio of the first host compound to the second host compound in the light-emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0056] An organic electroluminescent device according to one embodiment of the present disclosure includes a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and a hole transport zone between the first electrode and the light-emitting layer, wherein the hole transport zone comprises a compound represented by formula 1, and the light-emitting layer comprises a compound represented by the following formula 6 and a compound represented by the following formula 7.

[0057] [ka] In equation 6, L 11 ~L 13 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene. According to one embodiment of the present disclosure, L 11 ~L 13Each of these independently represents a single bond, a substituted or unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (3-20 member) heteroarylene. For example, L 11 ~L 13 Each of these can independently be a single bond, unsubstituted or deuterium-substituted phenylene, unsubstituted or deuterium-substituted biphenylene, unsubstituted or deuterium-substituted terphenylene, unsubstituted or deuterium-substituted naphthylene, phenantrenylene, dibenzofuranylene, dibenzothiophenylene, carbazoylene, or pyridylene, which may be further substituted with deuterium.

[0058] In equation 6, Ar 11 represents a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, Ar 11 represents a substituted or unsubstituted (3-25 member) heteroaryl. According to another embodiment of the present disclosure, Ar 11 This may be a substituted or unsubstituted (3-30 membered) heteroaryl having four or more rings. According to yet another embodiment of the present disclosure, Ar 11 It may be a substituted or unsubstituted (3-30 membered) heteroaryl having four or more rings fused together and necessarily containing an oxygen atom. According to yet another embodiment of the present disclosure, Ar 11 This can be expressed by the following equations 6-1 or 6-2. [ka]

[0059] In equations 6-1 and 6-2, T1 and T2 are independently -N= and -NR 20 -, -O-, or -S-, where one of T1 and T2 is -N=, and the other of T1 and T2 is -NR 20 It is -, -O-, or -S-. For example, T1 and T2 can independently be -N=, -O-, or -S-.

[0060] In equation 6-2, T3 represents either O or S. For example, T3 could be O.

[0061] In equation 6-1, R 40 R represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, R 40 R represents a substituted or unsubstituted (C6-C15) aryl or a substituted or unsubstituted (3-10 member) heteroaryl. For example, R 40 These may be unsubstituted or deuterium-substituted phenyl, naphthyl, biphenyl, or pyridyl, which may be further substituted with deuterium.

[0062] In equations 6-1 and 6-2, R 41 ~R 48 and R 22 ~R 33 Each is independent of L 11Linked to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted condensed ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono or di(C1-C30) alkylamino, substituted or unsubstituted mono Alternatively, it may represent a di(C2-C30) 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 (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, a substituted or unsubstituted mono or di(C6-C30) arylamino, a substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino, or be linked to an adjacent substituent to form a ring, provided that in formula 6-1, R 41 ~R 48 One of the following is L 11 It is connected to, and in equation 6-2, R 22 ~R 33 One of the following is L 11 It is connected to R. According to one embodiment of the present disclosure, 41 ~R 48 and R 22 ~R 33Each of these can independently represent hydrogen, deuterium, 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 condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino, a substituted or unsubstituted (C1-C30) alkyl(3-30 member) heteroarylamino, a substituted or unsubstituted mono or di(C6-C30) arylamino, a substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino, or be linked to an adjacent substituent to form a ring. According to another embodiment of the present disclosure, R 41 ~R 48 and R 22 ~R 33 Each of these independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 member) heteroaryl. For example, R 41 ~R 48 and R 22 ~R 33 These can each be independently hydrogen or deuterium.

[0063] In equation 6, Ar 12 and Ar 13Each of these is independently 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 mono or di(C1-C30) alkylamino, or a mono or di(C2-C30) alkenylamino. No represents 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. According to one embodiment of the present disclosure, Ar 12 and Ar 13 Each independently represents 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 mono or di(C6-C30) arylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino. According to another embodiment of the present disclosure, Ar 12 and Ar 13Each of these independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, a substituted or unsubstituted mono or di(C6-C30) arylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino. For example, Ar 12 and Ar 13 These are, independently, unsubstituted or deuterium-substituted, cyano, unsubstituted or deuterium-substituted phenyl, biphenyl, unsubstituted or deuterium-substituted naphthyl, phenantrenyl, dibenzofuranyl or carbazolyl-substituted phenyl, unsubstituted or deuterium-substituted or phenyl-substituted biphenyl, unsubstituted or deuterium-substituted, unsubstituted or deuterium-substituted phenyl, unsubstituted or pyridyl-substituted naphthyl, unsubstituted or deuterium-substituted phenantrenyl, dimethylfluorenyl, dimethylbenzofluorenyl, unsubstituted or deuterium-substituted diphenylfluorenyl, unsubstituted or deuterium-substituted o-terphenyl, m-terphenyl, unsubstituted or deuterium-substituted p-terphenyl, 2,6-dimethylphenyl, tert-butylphenyl, fluoranthenyl, anthracenyl, spirobifluorenyl These may be unsubstituted or deuterium-substituted quaterphenyl, unsubstituted or deuterium-substituted triphenylenyl, unsubstituted or deuterium-substituted dibenzofuranyl, unsubstituted or deuterium-substituted phenyl or pyridyl, unsubstituted or deuterium-substituted dibenzothiophenyl, unsubstituted or phenyl-substituted pyridyl, benzonaphthofuranyl, benzonaphthothiophenyl, unsubstituted or phenyl or biphenyl-substituted carbazolyl, phenoxadinyl, unsubstituted or phenyl-substituted benzimidazolyl, triphenylsilyl, dibenzoselenophenyl, methyl-substituted 14-membered heteroaryl, 22-membered heteroaryl, benzophenantrenyl, benzonaphthoselenophenyl, diphenylamino, phenylbiphenylamino, phenyldibenzofuranylamino, phenyldibenzothiophenylamino, or phenylpyridylamino, which may be further substituted with deuterium.

[0064] The organic electroluminescent compound represented by formula 6 may be selected from, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [Chemistry] [Chemistry] [Chemistry]

[0065] In the above compound, D n means that n hydrogens are replaced by deuterium, and n represents an integer from 1 to the maximum number of hydrogens in the compound.

[0066] The compounds represented by Formula 6 according to the present disclosure can be produced by synthetic methods known to those skilled in the art. In particular, synthetic methods disclosed in various patent documents can be used. For example, the compound represented by Formula 6-1 according to the present disclosure can be synthesized by referring to (Patent Document 6) (March 2, 2017) and (Patent Document 7) (September 5, 2018), but is not limited thereto. For example, the compound represented by Formula 6-2 can be produced by referring to the following Reaction Scheme 1, but is not limited thereto, and can be produced by synthetic methods known to those skilled in the art.

[0067] [Reaction Scheme 1] [Chemistry] In Reaction Scheme 1, Ar 12 and Ar 13 are as defined in Formula 6, T3 is as defined in Formula 6-2, and R is as defined for R 22 ~R 33 in Formula 6-2.

[0068] The light-emitting layer of the organic electroluminescent device includes not only the compound represented by Formula 6 but also the compound represented by Formula 7. [[ID=S2]] [Chemistry]

[0069] In Formula 7, X1 to X3 each independently represent N or CR 21 provided that at least one of X1 to X3 is N. For example, X1 to X3 can each independently be N.

[0070] In Formula 7, each R 21 independently represents hydrogen or deuterium.

[0071] In Formula 7, L 21 ~L 23 each independently represents a single bond, a substituted or unsubstituted (C6 - C30) arylene, or a substituted or unsubstituted (3 - 30 member) heteroarylene. According to one embodiment of the present disclosure, L 21 ~L 23 each independently represents a single bond, a substituted or unsubstituted (C6 - C25) arylene, or a substituted or unsubstituted (3 - 25 member) heteroarylene. According to another embodiment of the present disclosure, L 21 ~L 23 each independently represents a single bond, a substituted or unsubstituted (C6 - C20) arylene, or a substituted or unsubstituted (3 - 20 member) heteroarylene. For example, L 21 ~L 23 can each independently be a single bond, phenylene unsubstituted or substituted with deuterium, biphenylene unsubstituted or substituted with deuterium, terphenylene, naphthylene unsubstituted or substituted with deuterium, phenanthrenylene, dibenzofuranylene, or dibenzothiophenylene, and these can be further substituted with deuterium.

[0072] In Formula 7, Ar 21 ~Ar 23Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3-7 member) heterocycloalkyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl, provided that Ar 21 ~Ar 23 At least one of them is a substituted or unsubstituted (3-30 member) heteroaryl. According to one embodiment of the present disclosure, Ar 21 ~Ar 23 Each of these independently represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl. For example, Ar 21 ~Ar 23 Each of these independently comprises naphthyl substituted with unsubstituted or deuterium, naphthyl substituted with unsubstituted or unsubstituted or deuterium or phenyl, phenyl substituted with phenantrenyl or dibenzofuranil, biphenyl substituted with unsubstituted or deuterium, naphthyl or dibenzofuranil, triphenylenyl, triphenylsilyl, o-terphenyl, m-terphenyl, p-terphenyl substituted with unsubstituted or deuterium, phenantrenyl substituted with unsubstituted or phenyl or naphthyl, and unsubstituted or deuterium-substituted be These may be phenanthrenyl, unsubstituted or deuterium, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted biphenyl, naphthyl substituted with dibenzofuranyl or dibenzothiophenyl, quarterphenyl, fluoranthenyl, unsubstituted or deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl substituted with phenanthrenyl or triphenylenyl, or dibenzothiophenyl substituted with unsubstituted or phenyl, which may be further substituted with deuterium.

[0073] According to one embodiment of the present disclosure, formula 7 may be represented by any one of the following formulas 7-1 to 7-4. [ka]

[0074] In equations 7-1 to 7-4, Y is O, S, or NR. 36 It represents [something]. For example, Y is either O or S.

[0075] In equations 7-1 to 7-4, R 34 ~R 36 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, and substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl. R represents a arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono or di(C1-C30)alkylamino, a substituted or unsubstituted mono or di(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino, or can be linked to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R 34 ~R 36 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl. According to another embodiment of the present disclosure, R 34 ~R 36 Each of these independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C20) aryl. For example, R 34 ~R 36 Each of these can independently be hydrogen, deuterium, unsubstituted or naphthyl-substituted phenyl, unsubstituted or phenyl-substituted naphthyl, biphenyl, or phenantrenyl, which may be further substituted with deuterium.

[0076] In equations 7-1 to 7-4, L 21 ~L23 Ar 22 and Ar 23 This is defined in Equation 7.

[0077] In equations 7-1 to 7-4, n represents an integer from 1 to 3, m represents an integer from 1 to 4, and when n and m are integers greater than or equal to 2, each R 34 and each R 35 They may be the same as or different from one another.

[0078] The organic electroluminescent compound represented by formula 7 may be selected from, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0079] In the above compound, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer from 1 up to the maximum number of hydrogen atoms in the compound.

[0080] The compounds represented by Formula 7 in this disclosure can be synthesized by referring to (Patent Document 8) (October 14, 2021) and (Patent Document 9) (January 18, 2021), but are not limited thereto.

[0081] The light-emitting layer of the organic electroluminescent device may further contain additional compounds different from those represented by formulas 6 and 7.

[0082] The light-emitting layer according to another embodiment of the present disclosure may further include a third host compound in addition to the first and second host compounds.

[0083] The organic layer may further include, in addition to the hole transport layer, light-emitting layer, hole auxiliary layer, electron blocking layer, and light-emitting auxiliary layer, at least one layer selected from the hole injection layer, electron transport layer, electron injection layer, intermediate layer, hole blocking layer, and electron buffer layer. The organic layer may further include amine-based compounds and / or azine-based compounds in addition to the compounds 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-based compounds, such as arylamine-based compounds and styrylarylamine-based compounds, as hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, and electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include azine-based compounds as electron transport material, electron injection material, electron buffer material, and hole blocking material. In addition, the organic material layer may further include 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 that metal.

[0084] A compound according to one embodiment of the present disclosure may be used as a light-emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed to have various structures, such as side-by-side arrangements, stacked arrangements, or color conversion material (CCM) arrangements, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light-emitting units. In addition, an organic electroluminescent compound according to one embodiment of the present disclosure may also be used in organic electroluminescent devices containing quantum dots (QDs).

[0085] One of the first and second electrodes may be an anode, and the other may be a cathode. The first and second electrodes may be formed from a transparent conductive material, a semi-transparent 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.

[0086] A hole injection layer, hole transport layer, electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, in which case two compounds may be used simultaneously in each of the multilayers. In addition, the hole injection layer may be further doped with a p-dopant. An electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, preventing light leakage by confining excitons within the light-emitting layer and blocking electron overflow from the light-emitting layer. The hole transport layer or electron transport layer may also be multilayered, in which case multiple compounds may be used in each of the multilayers.

[0087] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof may 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, in which case 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 prevent holes from reaching 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, in which case each layer may use multiple compounds. In addition, the electron injection layer may be doped as an n-dopant.

[0088] A light-emitting auxiliary layer may be a layer positioned between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When positioned between the anode and the light-emitting layer, the light-emitting auxiliary layer may be used to facilitate hole injection and / or hole transport or to prevent electron overflow. When positioned between the cathode and the light-emitting layer, the light-emitting auxiliary layer may be used to facilitate electron injection and / or electron transport or to prevent hole overflow. In addition, a hole auxiliary layer may be positioned between a hole transport layer (or hole injection layer) and the light-emitting layer, and may have the effect of facilitating or inhibiting the hole transport rate (or hole injection rate), and thus can adjust the charge balance. If an organic electroluminescent device includes two or more hole transport layers, any further included hole transport layers may be used as hole auxiliary layers or electron blocking layers. Light-emitting 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.

[0089] In the organic electroluminescent device of this disclosure, it is preferable to arrange 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") on the inner surface of at least one of a pair of electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably arranged on the anode surface on the electroluminescent medium layer side, and the metal halide layer or metal oxide layer is preferably arranged on the cathode surface on the electroluminescent medium layer side. The driving stability of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of chalcogenides include SiO X (1≦X≦2), AlO X (1≦X≦1.5), includes SiON, SiAlON, etc. Preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc. Preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0090] In addition, in the organic electroluminescent devices of this disclosure, 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 located on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, thereby facilitating the injection and transport of electrons from the mixed region to the light-emitting medium. Furthermore, the hole transport compound is oxidized to cations, thereby facilitating the injection and transport of holes from the mixed region to the light-emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, while preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using a reducing dopant layer as a charge generation layer, an organic electroluminescent device having at least two light-emitting layers and emitting white light can be manufactured.

[0091] An organic electroluminescent device according to one embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light-emitting unit (light-emitting portion) may be formed in a structure in which two or more units are connected by a charge-generating layer. The organic electroluminescent device may include a plurality of two or more light-emitting units, for example a plurality of three or more light-emitting units, each having a first electrode and a second electrode facing each other on a substrate, and a light-emitting layer laminated between the first electrode and the second electrode and emitting light in a specific wavelength range. It may include a plurality of light-emitting units, each of which may include a hole transport band, a light-emitting layer and an electron transport band, the hole transport band may include a hole injection layer and a hole transport layer, and the electron transport band may include an electron transport layer and an electron injection layer. According to one embodiment of the present disclosure, three or more light-emitting layers may be included in a light-emitting unit. The plurality of light-emitting units may emit the same color or different colors. In addition, a single light-emitting unit may include one or more light-emitting layers, and these layers may be the same color or different colors. It may also include one or more charge-generating layers positioned between each of the light-emitting units. A charge-generating layer refers to a layer that generates holes and electrons when a voltage is applied. If there are three or more light-emitting units, charge-generating layers may be positioned between each light-emitting unit. These charge-generating layers may be the same or different from one another. By positioning charge-generating layers between light-emitting units, the current efficiency in each light-emitting unit is increased, and the charge can be distributed more smoothly. Specifically, a charge-generating layer may be positioned between two adjacent stacks, which can help drive a tandem organic electroluminescent device using only anode-cathode pairs, without another internal electrode located between the stacks.

[0092] The charge generation layer may consist of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer may be doped with alkali metals, alkaline earth metals, or compounds of alkali metals and alkaline earth metals. Alkali metals may include those selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and alkaline earth metals may include those selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may be made from a metal or organic material doped with a P-type dopant. For example, the metal may be made from one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials may be used as host materials in P-type dopants and P-type doped organic materials.

[0093] An organic electroluminescent device according to one embodiment of the present disclosure may further include one or more dopants in the light-emitting layer. The dopants included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may be selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) metallized complex compounds, more preferably from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) orthometallated complex compounds, and even more preferably an orthometallated iridium complex compound.

[0094] The dopants included in the organic electroluminescent devices of this disclosure may be, but are not limited to, compounds represented by the following formulas 101 or 102. [ka]

[0095] In equations 101 and 102, L' has the following structure 1-3: [ka] It is one of the following that can be selected. 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 (C1-C30) alkoxy, or can be linked to adjacent substituents to form a ring, for example, a ring having pyridine, for example, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted thienopyridine, a substituted or unsubstituted benzophropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted idenopyridine, a substituted or unsubstituted benzophroquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted idenoquinoline. R 104 ~R 107 Each of these independently represents hydrogen, deuterium, halogen, deuterium and / or halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, substituted or unsubstituted (C1-C30) alkoxy, or substituted or unsubstituted di(C1-C30) alkylamino, or is linked to an adjacent substituent to form a ring, for example, a ring having benzene, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted idenopyridine, substituted or unsubstituted benzoflopyridine, or substituted or unsubstituted benzothienopyridine. R 201 ~R 220Each independently represents hydrogen, deuterium, halogen, deuterium and / or halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C1-C30) alkoxy or substituted or unsubstituted di(C1-C30) alkylamino, or is linked to adjacent substituents to form a ring, for example, substituted or unsubstituted benzene, substituted or unsubstituted fluorene, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted furopyridine or substituted or unsubstituted thiophene can be formed. Z1 to Z4 each independently represents N or CK1. Each K1 independently represents hydrogen, deuterium, halogen, deuterium and / or halogen-substituted or unsubstituted (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 (C1-C30) alkoxy, or is linked to adjacent substituents to form a ring, for example, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuran or substituted or unsubstituted dibenzothiophene can be formed. s represents an integer of 1 to 3.

[0096] In particular, specific examples of the dopant compound include, but are not limited to, the following.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0097] To form each layer of the organic electroluminescent device of this disclosure, dry deposition methods such as vacuum deposition, sputtering, plasma deposition, ion plating, etc., or wet deposition methods such as spin coating, dip coating, flow coating, etc., can be used. When using a wet deposition method, the thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and which does not have any problems with film formation ability.

[0098] When forming an electroluminescent compound film according to the present disclosure, the film can be formed by the methods listed above, and can generally be formed by a co-evaporation or mixed evaporation process. 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 two cells simultaneously to evaporate the materials, while mixed evaporation is a 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.

[0099] According to one embodiment, the present disclosure can provide a display device comprising an electroluminescent compound represented by Formula 1. In addition, the organic electroluminescent device of the present disclosure can be used to manufacture display devices for smartphones, tablets, notebooks, PCs, TVs, etc., or display devices for cars, or lighting devices such as outdoor or indoor lighting.

[0100] The following describes in detail the method for preparing organic electroluminescent compounds according to this disclosure, their physical properties, and the driving voltage, current efficiency, and lifetime characteristics of OLEDs according to this disclosure. However, the following examples merely illustrate the properties of the compounds and OLEDs according to this disclosure, and this disclosure is not limited to the following examples. [Examples]

[0101] Example 1: Preparation of compound C-9 [ka] Compound A (11.1 g, 0.034 mol), Compound 1-1 (10 g, 0.031 mol), Pd2(dba)3 (1.5 g, 0.0017 mol), 50% P(tBu)3 (1.68 mL), NaOtBu (6.5 g, 0.068 mol), and toluene (170 mL) were dissolved in a flask, and the mixture was refluxed at 120°C for 2 hours. After the reaction was complete, the organic layer was extracted with methyl chloride (MC), and residual water was removed with magnesium sulfate. The organic layer was then separated by column chromatography to obtain Compound C-9 (13.3 g, yield: 69%).

[0102] [Table 1]

[0103] Example 2: Preparation of Compound C-29 [ka] Compound A (8.8 g, 0.027 mol), Compound 2-1 (10 g, 0.025 mol), Pd2(dba)3 (1.24 g, 0.00135 mol), 50% P(tBu)3 (1.3 mL), NaOtBu (5.2 g, 0.054 mol), and toluene (135 mL) were dissolved in a flask, and the mixture was refluxed at 120°C for 2 hours. After the reaction was complete, the organic layer was extracted by MC, and residual water was removed with magnesium sulfate. Subsequently, the organic layer was separated by column chromatography to obtain Compound C-29 (7.9 g, yield: 45%).

[0104] [Table 2]

[0105] Device Examples 1-1 and 1-2: Manufacturing of Red Emitting OLEDs According to the Disclosure An OLED according to the present disclosure was manufactured. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on the substrate holder of a vacuum evaporation apparatus. Compound HI-1 was introduced into the cell of the vacuum evaporation apparatus, and compound HT1-1 was introduced into another cell. The two materials were evaporated at different speeds, and compound HI-1 was deposited at a doping amount of 5 wt% based on the total amount of compound HI-1 and compound HT1-1 to form a hole injection layer having a thickness of 10 nm. Then, compound HT1-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compounds shown in Table 1 below were introduced into another cell of the vacuum evaporation apparatus, and a current was passed through the cell to evaporate them, thereby depositing a second hole transport layer having a thickness of 60 nm on the first hole transport layer. Next, compound HT3-1 was introduced into another cell of the vacuum evaporation apparatus and evaporated by passing a current through the cell, thereby depositing a third hole transport layer having a thickness of 7.5 nm on the second hole transport layer. After the formation of the hole injection layer and the hole transport layers, an emission layer was deposited thereon as follows. Compound H1-1 and compound H2-1 were introduced into two cells of the vacuum evaporation apparatus as hosts, and then the two compounds were evaporated at a ratio of 1:1. After compound D-39 was introduced into another cell as a dopant, the dopant was deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form an emission layer having a thickness of 36 nm on the third hole transport layer. Then, an electron buffer layer having a thickness of 5 nm was deposited on the emission layer using compound B-1 as an electron buffer material. Next, an electron transport layer was deposited on the electron buffer layer up to a thickness of 25 nm using a mixture of compound ET-1 and compound EI-1 in a weight ratio of 2:1 as an electron transport material. After compound EI-1 was deposited as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode was deposited at a thickness of 80 nm on the electron injection layer using another vacuum evaporation apparatus to manufacture an OLED.

[0106] Comparative Examples 1-1 and 1-2: Manufacture of Red Emission OLEDs Not According to the Present Disclosure The OLED was manufactured using the same method as in Device Example 1-1, except that the compounds for the second hole transport layer listed in Table 1 below were used.

[0107] The driving voltage and current efficiency of the OLEDs manufactured using the above-described device examples 1-1 and 1-2, and comparative examples 1-1 and 1-2, were measured, and the results are shown in Table 1 below.

[0108] [Table 3]

[0109] Device Examples 2-1 and 2-2: Manufacturing of Red Emitting OLEDs According to the 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, and then stored in isopropyl alcohol. The ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Compound HI-1 was introduced into the cell of the vacuum deposition apparatus, and compound HT1-2 was introduced into another cell. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 3 wt% based on the total amount of compound HI-1 and compound HT1-2 to form a hole injection layer with a thickness of 10 nm. Subsequently, compound HT1-2 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, the compounds shown in Table 2 below were introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate them, thereby depositing a second hole transport layer with a thickness of 55 nm on the first hole transport layer. Next, compound HT3-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing an electric current through the cell, thereby depositing a third hole transport layer with a thickness of 5 nm on the second hole transport layer. After the formation of the hole injection layer and the hole transport layer, an emissive layer was deposited on top of them as follows: Compounds H1-2 and H2-1 were introduced into two cells of the vacuum deposition apparatus as hosts, and the two compounds were evaporated in a 1:1 ratio. Compound D-39 was introduced into another cell as a dopant, and the dopant was deposited at a doping amount of 2 wt% relative to the total amount of hosts and dopants, forming an emissive layer with a thickness of 40 nm on the third hole transport layer. Next, an electron buffer layer with a thickness of 5 nm was deposited on the emissive layer using compound B-2 as the electron buffer material. Then, an electron transport layer was deposited on the electron buffer layer to a thickness of 30 nm using a mixture of compounds ET-2 and EI-1 in a 1:1 weight ratio as the electron transport material. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm onto the electron transport layer, an Al cathode was deposited on the electron injection layer with a thickness of 80 nm using a separate vacuum deposition apparatus to produce an OLED.

[0110] Comparative Example 2-1: Manufacturing of a red light-emitting OLED not according to this disclosure The OLED was manufactured using the same method as in Device Example 2-1, except that the compound for the second hole transport layer, as described in Table 2 below, was used.

[0111] The current efficiency at a brightness of 1,000 nits and the time required for the brightness to decrease from 100% to 95% (lifetime: T95) at a brightness of 10,000 nits were measured for the OLEDs manufactured using the above-described Device Examples 2-1 and 2-2 and Comparative Example 2-1. The results are shown in Table 2 below.

[0112] [Table 4]

[0113] Device Examples 3-1 to 3-3: Manufacturing of Red Emitting OLEDs According to This Disclosure The OLED was manufactured using the same method as in Device Example 1-1, except that the compounds for the second hole transport layer listed in Table 3 below were used.

[0114] Comparative Example 3-1: Manufacturing of a red light-emitting OLED not according to this disclosure The OLED was manufactured using the same method as in Device Example 3-1, except that the compound for the second hole transport layer, as described in Table 3 below, was used.

[0115] The driving voltage, current efficiency, and CIE chromaticity coordinates were measured at a brightness of 1,000 nits for the OLEDs manufactured using the above-described device examples 3-1 to 3-3 and comparative example 3-1. The results are shown in Table 3 below.

[0116] [Table 5]

[0117] Device Examples 4-1 to 4-3: Manufacturing of Red Emitting OLEDs According to This Disclosure An OLED was manufactured using the same method as in Device Example 1-1, except that each of the compounds listed in Table 4 below was used for the second hole transport layer, and each of the compounds listed in Table 4 below was used as the host material for the light-emitting layer by co-deposition using a 4:6 ratio.

[0118] Comparative Example 4-1: Manufacturing of a red light-emitting OLED not according to this disclosure The OLED was manufactured using the same method as in Device Example 4-1, except that the compound for the second hole transport layer, as described in Table 4 below, was used.

[0119] The driving voltage, current efficiency, and CIE chromaticity coordinates were measured at a brightness of 1,000 nits for the OLEDs manufactured using the above-described device examples 4-1 to 4-3 and comparative example 4-1. The results are shown in Table 4 below.

[0120] [Table 6]

[0121] Device Examples 5-1 to 5-3: Manufacturing of Red Emitting OLEDs According to This Disclosure An OLED was manufactured using the same method as in Device Example 1-1, except that each of the compounds listed in Table 5 below was used for the second transport layer, and each of the compounds listed in Table 5 below was used as the host material for the light-emitting layer by co-deposition using a ratio of 4:2:4.

[0122] Comparative Example 5-1: Manufacturing of a red light-emitting OLED not according to this disclosure The OLED was manufactured using the same method as in Device Example 5-1, except that the compound for the second transport layer, as described in Table 5 below, was used.

[0123] The driving voltage, current efficiency, and CIE chromaticity coordinates were measured at a brightness of 1,000 nits for the OLEDs manufactured using the above-described device examples 5-1 to 5-3 and comparative example 5-1. The results are shown in Table 5 below.

[0124] [Table 7]

[0125] Device Examples 6-1 and 6-2: Manufacturing of Red Emitting OLEDs According to the Disclosure An OLED was manufactured using the same method as in Device Example 1-1, except that each of the compounds listed in Table 6 below was used for the second hole transport layer, and each of the compounds listed in Table 6 below was used as the host material for the light-emitting layer by co-deposition using a 4:6 ratio.

[0126] Comparative Example 6-1: Manufacturing of a red light-emitting OLED not according to this disclosure The OLED was manufactured using the same method as in Device Example 6-1, except that the compound for the second hole transport layer, as described in Table 6 below, was used.

[0127] The driving voltage, current efficiency, and CIE chromaticity coordinates at a brightness of 1,000 nits were measured for the OLEDs manufactured using the above-described device examples 6-1 and 6-2 and comparative example 6-1. The results are shown in Table 6 below.

[0128] [Table 8]

[0129] From Tables 1 to 6 above, it can be seen that the OLEDs containing the organic electroluminescent compound according to this disclosure exhibit lower drive voltage, higher current efficiency, and longer lifetime characteristics compared to organic electroluminescent devices using conventional compounds in the second hole transport layer.

[0130] The compounds used in the device examples and comparative examples are shown in Table 7 below.

[0131] [Table 9]

[0132] [Table 10]

[0133] Table 11

Claims

1. The following equation 1: 【Chemistry 1】 (In Equation 1, X is -O-, -S-, -Se-, -Ge- or -(CR ９ R １０ ) ｎ - represents, Ring A represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring, and the two adjacent carbon atoms in ring A are each represented by formula 1-A 【Chemistry 2】 It is attached at the * position in the aliphatic ring, R １ to R ４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring or -L-N(L １ -Ar １ )(L ２ -Ar ２ ), and R ９ and R １０ Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl or a substituted or unsubstituted (C6-C30) aryl, or R ９ and R １０ They can be connected to each other to form a ring, R １１ and R １２ Each of these independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, and each R １１ or each R １２ They may be the same or different from each other. L, L １ and L ２ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. L is R １ ~R ４ It is linked to at least one carbon atom selected from the group consisting of a carbon atom bonded to any one of the and carbon atoms of the benzene ring or the naphthalene ring of ring A, Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 member) heteroaryl, or a substituted or unsubstituted (C3-C30) cycloalkyl. n represents an integer of 1 or 2, m represents an integer from 1 to 3, and a represents an integer of 1 or 2. An organic electroluminescent compound represented by, In the compound represented by formula 1, the hydrogen atom may be substituted with deuterium. However, if ring A is a substituted or unsubstituted benzene ring, L １ , L ２ Ar １ and Ar ２ This refers to an organic electroluminescent compound that does not contain an aryl compound condensed with a heteroaryl or cycloalkyl group.

2. The substituted alkyl, the substituted aryl(len), the substituted heteroaryl(len), the substituted cycloalkyl(len), the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the fused ring group of the substituted aliphatic ring and the substituted aromatic ring, the substituted benzene ring and the substituted naphthalene ring are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo(C1-C30) Alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (3-30 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, (C3-C30) fused ring group of an aliphatic ring and (C6-C30) aromatic ring, amino, mono or di(C1-C30) alkylamino, mono or di(C6-C30) arylamino, (C1-C30) alkyl(C6-C30) arylamino, mono or di(3-30 member) heteroarylamino, (C1-C30) alkyl(3-30 member) heteroarylamino, (C6-C30) aryl(3-30 member) heteroarylamino, (C1-C30) alkylcarbonyl The organic electroluminescent compound according to claim 1, which is substituted with at least one selected from the group consisting of (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) aryl(C1-C30) alkyl, (C1-C30) alkyl(C6-C30) aryl, and combinations thereof.

3. Equation 1 is the following equations 2-1 to 2-4: 【Transformation 3】 (In equations 2-1 to 2-4, R in Equation 2-1 ５ and R ６ , R ６ and R ７ And R ７ and R ８ One pair selected from is linked to the * position in Equation 1-A, R' in equations 2-2 to 2-4 １ and R' ２ , R' ２ and R' ３ R' ３ and R' ４ One pair selected from is linked to the * position in Equation 1-A, X, R １ ~R ４ L, L １ , L ２ Ar １ and Ar ２ This is as defined in claim 1, and R not linked to Equation 1-A ５ ~R ８ and R' １ ~R' ４ Each of them is independent of R １ (This is the same as the definition for...) The organic electroluminescent compound according to claim 1, represented by any one of the following.

4. Equation 1 is the following equations 3-1 to 3-4: 【Chemistry 4】 (In equations 3-1 to 3-4, X, R １ ~R ４ L, L １ , L ２ Ar １ and Ar ２ This is as defined in claim 1, and R ５ ~R ８ , R' １ and R' ４ Each of them is independent of R １ (This is the same as the definition given for...) The organic electroluminescent compound according to claim 1, represented by any one of the following.

5. Equation 1 is the following equations 4-1 to 4-4: 【Transformation 5】 (In formulas 4-1 to 4-4, X, R １ ~R ４ L, L １ , L ２ Ar １ and Ar ２ This is as defined in claim 1, and R ５ ~R ８ , R' １ and R' ４ Each of them is independent of R １ (This is the same as the definition given for...) The organic electroluminescent compound according to claim 1, represented by any one of the following.

6. Equation 1 is the following equations 5-1 to 5-4: 【Transformation 6】 (In formulas 5-1 to 5-4, X, R １ ~R ４ L, L １ , L ２ Ar １ and Ar ２ This is as defined in claim 1, and R ５ ~R ８ , R' １ and R' ４ Each of them is independent of R １ (This is the same as the definition given for...) The organic electroluminescent compound according to claim 1, represented by any one of the following.

7. Ar １ and Ar ２ The organic electroluminescent compound according to claim 1, wherein at least one of comprises a (C6-C30) aryl substituted with a (C1-C30) alkyl or a (C3-C30) cycloalkyl.

8. The following compounds: 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 An organic electroluminescent compound according to claim 1, selected from the above.

9. An organic electroluminescent material comprising the organic electroluminescent compound described in claim 1.

10. An organic electroluminescent device comprising the organic electroluminescent compound described in claim 1.

11. The organic electroluminescent device according to claim 10, wherein at least one layer selected from a hole transport layer, an emissive layer, a hole auxiliary layer, an electron blocking layer, and an emissive layer contains an organic electroluminescent compound.

12. An organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and a hole transport band between the first electrode and the light-emitting layer, The hole transport zone comprises a compound represented by formula 1 as described in claim 1, The light-emitting layer comprises a compound represented by the following formula 6 and a compound represented by the following formula 7: 【Chemistry 46】 (In Equation 6, L １１ ~L １３ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene. Ar １１ This represents a substituted or unsubstituted (3-30 member) heteroaryl, Ar １２ and Ar １３ each independently represents 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 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), 【Chemistry 47】 (In Equation 7, X １ ~X ３ Each of these is independently N or CR ２１ This represents, however, X １ ~X ３ At least one of them is N, Each R ２１ It independently represents hydrogen or deuterium. L ２１ to L ２３ each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene or a substituted or unsubstituted (3-30 member) heteroarylene, and Ar ２１ ~Ar ２３ Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (3-7 member) heterocycloalkyl, a substituted or unsubstituted condensed ring group of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 member) heteroaryl. However, Ar ２１ ~Ar ２３ At least one of them is a substituted or unsubstituted (3-30 member) heteroaryl compound. Organic electroluminescent devices, including those mentioned above.

13. Ar in Equation 6 １１ The organic electroluminescent device according to claim 12, wherein is a substituted or unsubstituted (3 to 30 membered) heteroaryl having four or more fused rings and always containing an oxygen atom.

14. Ar in Equation 6 １１ This is expressed by the following equation 6-1 or 6-2: 【Chemistry 48】 (In formulas 6-1 and 6-2, T １ and T ２ These are independently -N= and -NR ２０ -, -O-, or -S- represent, however, T １ and T ２ One of them is -N = and T １ and T ２ The other is -NR ２０ -, -O- or -S-, T ３ This represents O or S, R ４０ This represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 member) heteroaryl, and R ４１ ~R ４８ and R ２２ ~R ３３ Each is independent of L １１ Linked to, or hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted condensed ring group of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, substituted or unsubstituted mono or di(C1-C30) alkylamino, substituted or This represents an unsubstituted mono or di(C2-C30) 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 (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, a substituted or unsubstituted mono or di(C6-C30) arylamino, a substituted or unsubstituted mono or di(3-30 member) heteroarylamino, or a substituted or unsubstituted (C6-C30) aryl(3-30 member) heteroarylamino, or may be linked to adjacent substituents to form a ring. However, in equation 6-1, R ４１ ~R ４８ One of the following is L １１ It is connected to, and In equation 6-2, R ２２ ~R ３３ One of the following is L １１ (It is connected to) The organic electroluminescent device according to claim 12, as represented by [the specified figure].

15. Equation 7 is the following equations 7-1 to 7-4: 【Chemistry 49】 (In formulas 7-1 to 7-4, Y is O, S, or NR ３６ This represents, R ３４ ~R ３６ Each of these 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 (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) Represents a arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono or di(C1-C30)alkylamino, a substituted or unsubstituted mono or di(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30)arylamino, or may be linked to adjacent substituents to form a ring. L ２１ ~L ２３ Ar ２２ and Ar ２３ This is as defined in claim 12, n represents an integer from 1 to 3, m represents an integer from 1 to 4, and If n and m are integers greater than or equal to 2, then each R ３４ and each R ３５ (These may be the same or different from each other.) The organic electroluminescent device according to claim 12, represented by any one of the following.

16. The compound represented by formula 6 is the following compound: [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Transformation 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 (In the above compound, D ｎ This means that n hydrogen atoms are replaced by deuterium, and n is an integer from 1 to the maximum number of hydrogen atoms in the compound. An organic electroluminescent device according to claim 12, selected from the above.

17. The compound represented by formula 7 is the following compound: 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Transformation 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Chemistry 87】 【Chemical 88】 【Chemical 89】 【Chemistry 90】 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 (In the above compound, D ｎ This means that n hydrogen atoms are replaced by deuterium, and n is an integer from 1 to the maximum number of hydrogen atoms in the compound. An organic electroluminescent device according to claim 12, selected from the above.

18. The organic electroluminescent device according to claim 12, wherein the light-emitting layer further comprises additional compounds different from the compounds represented by formulas 6 and 7.

Images