Organic electroluminescent compounds and organic electroluminescent elements containing the same

Abstract

The present invention provides organic electroluminescent compounds and organic electroluminescent elements containing the same. [Solution] This disclosure relates to an organic electroluminescent compound represented by Formula 1 and an organic electroluminescent element containing the same. It is possible to provide an organic electroluminescent element having a lower drive voltage and / or higher current efficiency and / or improved lifetime characteristics compared to conventional organic electroluminescent elements.

Description

[Technical Field]

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

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

[0003] (Patent Document 1) discloses compounds containing phenanthroline derivatives. However, this document does not specifically disclose the particular compound that is the subject of this disclosure. There is a continuing need to develop organic electroluminescent compounds that have improved performance, such as improved drive voltage and / or luminous efficiency and / or lifetime characteristics, compared to compounds disclosed to date. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Korean Patent Application Publication No. 2023-0151982 Specification [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] An object of the present disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. Another object of the present disclosure is to provide an organic electroluminescent device having a low driving voltage and / or a high current efficiency and / or improved lifetime characteristics.

Means for Solving the Problems

[0006] As a result of intensive research to solve the above technical problems, the present inventors have discovered that the above objects can be achieved by an organic electroluminescent compound represented by the following formula 1 and an organic electroluminescent device containing the same, thereby completing the present invention.

Chemical formula

[0007] In formula 1, X1 to X 10 each independently represents CR4 or N; R1 to R4 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C2 to C 30 ) alkenyl, substituted or unsubstituted (C3 to C 30 ) cycloalkyl, substituted or unsubstituted (C3 to C 30 ) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, or -(L) a -HAr; At least one of R1 to R4 is -(L) a -HAr; When R2 is -(L) a -HAr, each R4 independently represents hydrogen, deuterium, or a cyano group; Each L independently represents a single bond, substituted or unsubstituted (C6 to C 30 ) arylene, substituted or unsubstituted (C2 to C 30 ) alkenylene, substituted or unsubstituted (C2 to C30 ) Represents alkynylene, or substituted or unsubstituted (3-30 member) heteroarylene; a is an integer of either 1 or 2, and if a is 2, then L may be the same as or different from the other; HAr represents a substituted or unsubstituted (3-30 member) heteroaryl containing at least one nitrogen atom; However, R2 is -(L) a -HAr is a substituted or unsubstituted phenanthrolinyl, and L is substituted or unsubstituted (C2~C 30 ) Alkenylene or substituted or unsubstituted (C2~C 30 If it is not an alkynylene, L is attached to one of the positions 3-8 of phenanthrolinyl.

[0008] Effects of the invention The organic electroluminescent compounds according to this disclosure exhibit performance suitable for use in organic electroluminescent devices. By using the organic electroluminescent compounds according to this disclosure in an N-type charge generation layer, it is possible to provide an organic electroluminescent device having a lower drive voltage and / or higher current efficiency and / or improved lifetime characteristics compared to conventional organic electroluminescent devices. In addition, it is possible to manufacture display devices or lighting devices using this device. [Modes for carrying out the invention]

[0009] The following provides a detailed description of this disclosure. However, the following description is intended to explain the disclosure and is not intended to limit its scope.

[0010] In this disclosure, "organic electroluminescent compound" refers to a compound that can be used in an organic electroluminescent device and, if necessary, can be incorporated into any layer constituting the organic electroluminescent device.

[0011] In this specification, "(C1~C 30"(C3-C)alkyl" means a linear or branched alkyl group having 1 to 30 carbon atoms (where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10) that make up the chain. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and sec-butyl. In this specification, "(C3-C)alkyl" means a linear or branched alkyl group having 1 to 30 carbon atoms (where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10). 30 "(3-7 membered) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in its ring skeleton, preferably 3 to 20, more preferably 3 to 7 carbon atoms. Examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, norbornyl, and adamantyl. In this specification, "(3-7 membered) heterocycloalkyl" is intended to be a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent having 3 to 7 ring skeleton atoms, preferably 5 to 7 carbon atoms, and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, and Se. Examples of heterocycloalkyls include tetrahydrofuran, pyrrolidine, thiolane, and tetrahydropyran.

[0012] In this specification, "(C2~C 30 ) Alkenil (En)" or "(C2~C 30 "Alkynyl(ene)" means a linear or branched alkenyl group or alkenylene group having 2 to 30 carbon atoms (preferably 2 to 20, more preferably 2 to 10) that make up the chain. An alkenyl group refers to a substituent containing at least one double bond, and an alkynyl group refers to a substituent containing at least one triple bond. These substituents may be located at the terminal or in the interior. Examples of alkenyls include ethenyl, propenyl, butenyl, and pentenyl, and examples of alkynyls include ethynyl, propynyl, butynyl, and pentynyl. These may have a linear or branched structure.

[0013] In this specification, "(C6~C 30 )aryl" or "(C6~C 30"Arylene" refers to a monocyclic or fused radical derived from a partially saturated aromatic hydrocarbon having 6 to 30, preferably 6 to 20, and more preferably 6 to 15 cyclic carbon atoms in its cyclic skeleton. The aryl may contain a spiro structure. Examples of aryl compounds include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenantrenyl, benzophenantrenyl, phenylphenantrenyl, anthracenyl, benzoanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracerenyl, perilenyl, crisenyl, benzocrisenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, coumenyl, spiro[fluoren-fluoren]yl, spiro[fluoren-benzofluoren]yl, azurenyl, and tetramethyl-dihydrophenantrenyl. More specifically, examples of aryls include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butylp-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 Lu-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, 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 Zo[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-bebenzo[b]fluorenyl, 11,11-dimethyl-7-bebenzo[b]fluorenyl, 11,11-dimethyl-8-bebenzo[b]fluorenyl Olenyl, 11,11-dimethyl-9-bebenzo[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 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl 6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-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[Pc]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,Examples include 10-dihydro-3-phenantrenyl and 9,9,10,10-tetramethyl-9,10-dihydro-4-phenantrenyl.

[0014] In this specification, "(3-30 membered) heteroaryl" or "(3-30 membered) heteroarylene" means 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, where the number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20. In this specification, the number of heteroatoms is preferably 1 to 4. Heteroaryl or heteroarylene may be monocyclic, fused ring, or partially saturated. In addition, heteroaryl or heteroarylene may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and this may include a spiro structure. Examples of 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; and benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, dibenzothiophenyl, benzofloquinolinil, benzofloquinazolinil, benzoflonaphtylidinil, benzoflopyrimidinil, naphthoflopyrimidinil, benzothienocinolinil, benzothienocinazolinil, benzothienonaphtylidinil, Nzothienopyrimidinil, naphthienopyrimidinil, pyrimidoindolyl, benzopyrimidoindolyl, benzoflopyrazinil, naphthoflopyradinil, benzothienopyrazinil, naphththienopyrazinil, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinil, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinel,These can be condensed ring heteroaryls such as benzodioxolyl, indolidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenadinyl, imidazopyridinyl, clomenoquinazolinyl, thioclomenoquinazolinyl, dimethylbenzopyrimidinyl, indocarbazolyl, and indenocarbazolyl. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, and 3-indolidinyl. 5-Indlididinyl, 6-Indlididinyl, 7-Indlididinyl, 8-Indlididinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl Ryl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranil, 3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl Lu, 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, Azacarbazole-1-yl, Azacarbazole-2-yl, Azacarbazole-3-yl, Azacarbazole-4-yl,Azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-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 Ryl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 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-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly L, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho[1,2-b]benzofuranyl, 2-naphtho[1,2-b]benzofuranyl, 3-naphtho[1,2-b]benzofuranyl, 4-naphtho[1,2-b] Benzofuranil, 5-naphtho[1,2-b]benzofuranil, 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]benzofuranil, 9-Naphtho [2,1-b]benzofuranyl, 10-naphtho[2,1-b]benzofuranyl, 1-naphtho[1,2-b]benzothiophenyl, 2-naphtho[1,2-b]benzothiophenyl, 3-naphtho[1,2-b]benzothiophenyl, 4-naphtho[1,2-b]benzothiophenyl, 5-naphtho[1,2-b]benzothiophenyl, 6-naphtho[1,2-b]benzothiophenyl, 7-naphtho[1,2-b]benzothiophenyl, 8-naphtho[1,2-b]benzothiophenyl, 9-naphtho[1,2-b]benzothiophenyl, 10-naphtho[1,2 -b]benzothiophenyl, 1-naphtho[2,3-b]benzothiophenyl, 2-naphtho[2,3-b]benzothiophenyl, 3-naphtho[2,3-b]benzothiophenyl, 4-naphtho[2,3-b]benzothiophenyl, 5-naphtho[2,3-b]benzothiophenyl, 1-naphtho[2,1-b]benzothiophenyl, 2-naphtho[2,1-b]benzothiophenyl, 3-naphtho[2,1-b]benzothiophenyl, 4-naphtho[2,1-b]benzothiophenyl, 5-naphtho[2,1-b]benzothiophenyl, 6-naphtho[2,1-b] Benzothiophenyl, 7-naphtho[2,1-b]benzothiophenyl, 8-naphtho[2,1-b]benzothiophenyl, 9-naphtho[2,1-b]benzothiophenyl, 10-naphtho[2,1-b]benzothiophenyl, 2-benzoflo[3,2-d]pyrimidinyl, 6-benzoflo[3,2-d]pyrimidinyl, 7-benzoflo[3,2-d]pyrimidinyl, 8-benzoflo[3,2-d]pyrimidinyl, 9-benzoflo[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[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]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzothio[ Examples include 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, and 4-dibenzoselenophenyl. In addition, heteroaryl(enes) can be classified into heteroaryl(enes) that have electronic properties and heteroaryl(enes) that have hole properties. Heteroaryl(ene) compounds with electronic properties have a parent molecule that is relatively electron-rich, such as substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted quinolyl. Heteroaryl(ene) compounds with hole properties have a parent molecule that is relatively electron-poor, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0015] In this specification, "(C3~C 30 ) aliphatic ring and (C6~C 30The term "condensed ring group with an aromatic ring" refers to a functional group of a ring formed by condensing at least one aliphatic ring having 3 to 30, preferably 3 to 25, more preferably 3 to 18 carbon atoms in its ring skeleton with at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 carbon atoms in its ring skeleton. For example, a condensed ring group can be a condensed ring group of at least one benzene and at least one cyclohexane, or a condensed ring group of at least one naphthalene and at least one cyclopentane. In this specification, (C3~C 30 ) aliphatic ring and (C6~C 30 The carbon atoms in the fused ring group with the aromatic ring can be replaced with at least one heteroatom selected from B, N, O, S, Si, P, and Se. In this disclosure, "halogen" includes F, Cl, Br, and I.

[0016] 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 the two substituents of 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 the two substituents of 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 the two substituents of a benzene derivative occupy positions 1 and 4, this is called a "para-" configuration.

[0017] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced by another atom or another functional group, i.e., a substituent. Substituents include those with two or more substituents attached. Unless otherwise specified, substituents can replace hydrogen at any location where a substituent can be substituted without limitation, and if two or more hydrogen atoms in a particular functional group are each replaced by substituents, each substituent may be the same or different from one another. For a given functional group, the maximum number of substituents that can be substituted may be the total number of substituted valencies for each atom forming the functional group. In the formulas of this disclosure, substituted alkyl, substituted alkenyl(ene), substituted alkynyl(ene), substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl, substituted cycloalkenyl, and substituted heterocycloalkyl are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 ) Alkyl, Halo (C1~C 30 ) Alkyl, (C2~C 30 ) Alkenil, (C2~C 30 ) Alkinyl, (C1~C 30 )alkoxy, (C1~C 30 ) alkylthio, (C3~C 30 )Cycloalkyl, (C3~C 30 )Cycloalkenyl, (3-7 member) heterocycloalkyl, (C6-C 30 ) Aryl oxy, (C6~C 30 ) Arylthio, (3-30 member) Heteroaryl, (C6-C 30 )Aaryl, Tri (C1~C 30 ) Alkylsilyl, tri(C6~C 30 ) Arylsilyl, di(C1~C 30 ) Alkyl (C6~C 30 ) Arylsilyl, (C1~C 30 ) Alkyl di(C6~C 30 ) Arylsilyl, (C3~C 30 ) aliphatic ring and (C6~C 30 ) A condensed ring group with an aromatic ring, amino, mono or di(C1~C 30) Alkylamino, mono or di(C6~C 30 ) Arylamino, (C1~C 30 ) Alkyl (C6~C 30 ) Arylamino, mono or di(3-30 member) heteroarylamino, (C1-C 30 )Alkyl (3-30 member) heteroarylamino, (C6-C 30 )aryl (3-30 member) heteroarylamino, (C1-C 30 ) Alkylcarbonyl, (C1~C 30 ) Alkoxycarbonyl, (C6~C 30 ) Arylcarbonyl, (C6~C 30 ) Arylphosfinyl, di(C6~C 30 ) Arylboronyl, di(C1~C 30 ) Alkylboronyl, (C1~C 30 ) Alkyl (C6~C 30 ) Arylboronyl, (C6~C 30 )ar(C1~C 30 ) alkyl, (C1~C 30 ) Alkyl (C6~C 30 ) may be substituted with at least one selected from the group consisting of aryls and combinations thereof. According to one embodiment of the present disclosure, this group is deuterium, (C1~C 20 ) alkyl, (C6~C 25 )aryl, (3-membered to 25-membered) heteroaryl, and combinations thereof. According to another embodiment of the present disclosure, this group may consist of deuterium, (C1-C 10 ) alkyl, (C6~C 18 The group can consist of aryl groups, (6- to 14-membered) heteroaryl groups, and combinations thereof. For example, the group can consist of deuterium, methyl, phenyl, naphthyl, biphenyl, pyridyl, pyridyl-substituted pyridyl, and these may be further substituted with deuterium.

[0018] In this specification, if a substituent is not shown in a formula or compound structure, it may mean that all possible positions of the substituent 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 can be 0% to 100%. In this disclosure, if a substituent is not shown in a formula or compound structure and deuterium is not explicitly excluded, such as 0% deuterium, 100% hydrogen, or all substituents being hydrogen, then hydrogen and deuterium may be used together in a compound. Deuterium is one of the isotopes of hydrogen and is an element that has a deuteron consisting of one proton and one neutron as its nucleus. It can 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.

[0019] In this specification, “these combinations” means a combination of one or more elements from the corresponding list to form a known or chemically stable configuration that can be conceived by those skilled in the art from the corresponding list. For example, alkyl and deuterium can be combined to form a partially or completely deuterated alkyl group, halogen and aryl can be combined to form an alkyl halide substituent, and halogen, alkyl, and aryl can be combined to form an arylalkyl halide. For example, preferred combinations of substituents may include up to 50 atoms excluding hydrogen or deuterium, or up to 40 atoms excluding hydrogen or deuterium, or up to 30 atoms excluding hydrogen or deuterium, or in many cases, preferred combinations of substituents may include up to 20 atoms excluding hydrogen or deuterium.

[0020] 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 or different from one another.

[0021] The compound represented by Formula 1 is described in more detail below.

[0022] In Equation 1, X1~X 10 Each of these independently represents CR4 or N. According to one embodiment of the present disclosure, X1 to X 10 At least one of them is N. For example, X1 may be N, or X5 may be N. According to another embodiment of the present disclosure, X1~X 10 Two or more of these are N. According to yet another embodiment of the present disclosure, one of X1 to X5 is N, and X6 to X 10 One of them is N. For example, X1 or X5 is N, and X6 or X 10 It is N.

[0023] In Equation 1, R1 to R4 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C2~C 30 ) Alkenyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C3~C 30 ) Cycloalkenyl, substituted or unsubstituted (3-membered to 7-membered) heterocycloalkyl, or -(L) a - Represents HAr; at least one of R1~R4 is -(L) a -HAr is; R2 is -(L) a -HAr, in which case each R4 independently represents hydrogen, deuterium, or a cyano group. According to one embodiment of the present disclosure, any one of R1 to R4 is -(L) a -HAr, and the remainder are independently hydrogen, deuterium, or cyano. According to another embodiment of the present disclosure, one of R1 to R4 is -(L) a -HAr, with the remaining atoms being either hydrogen or deuterium, respectively. For example, one of R2 and R4 is -(L). a -HAr

[0024] Each L independently consists of a single bond, substitution, or unsubstituted (C6~C30 )arylene, substituted or unsubstituted (C2-C 30 )alkenylene, substituted or unsubstituted (C2-C 30 )alkynylene, or substituted or unsubstituted (3-30 member) heteroarylene. According to one embodiment of the present disclosure, L is a single bond, substituted or unsubstituted (C6-C 18 )arylene, substituted or unsubstituted (C2-C 20 )alkenylene, substituted or unsubstituted (C2-C 20 )alkynylene, or substituted or unsubstituted (6-14 member) heteroarylene. According to another embodiment of the present disclosure, L is a single bond, unsubstituted or substituted with deuterium or (C1-C 30 )alkyl-substituted (C6-C 13 )arylene, substituted or unsubstituted (C2-C 10 )alkynylene, or unsubstituted or substituted with deuterium or (C6-C 30 )aryl-substituted (6-13 member) heteroarylene. For example, L may be a single bond, ethynylene, phenylene, naphthylene, biphenylene, phenanthrenylene, dimethylfluorenylene, dibenzofuranylene, dibenzothiophenylene, quinolenylene, pyridylene, etc., which may be substituted with at least one selected from the group consisting of deuterium, phenyl, pyridyl, and combinations thereof.

[0025] a is an integer of 1 or 2, and when a is 2, L may be the same as or different from the other.

[0026] HAr represents a substituted or unsubstituted (3-30 member) heteroaryl containing at least one nitrogen atom. According to one embodiment of the present disclosure, HAr is a substituted or unsubstituted (5-20 member) heteroaryl containing at least one nitrogen atom. According to another embodiment of the present disclosure, HAr is a substituted or unsubstituted (6-15 member) heteroaryl containing one or two nitrogen atoms. As used herein, heteroaryl is deuterium, (C1-C 30 )alkyl, (C6-C 30) It may be substituted with at least one selected from the group consisting of aryl, (3- to 30-membered) heteroaryl, and combinations thereof. For example, HAr may be pyridyl, terpyridyl, quarterpyridyl, triazinyl, quinoxalinyl, quinazolinyl, pyrimidinyl, pyrazinyl, phenanthrolinyl, phenanthroxazolyl, phenanthrothiazolyl, naphthoxazolyl, naphthothiazolyl, etc., and these may be substituted with at least one selected from the group consisting of deuterium, methyl, pyridyl, pyridyl-substituted pyridyl, phenyl, naphthyl, biphenyl, and combinations thereof.

[0027] In Formula 1, when R2 is -(L) a -HAr and HAr is substituted or unsubstituted phenanthrolinyl, and L is not substituted or substituted (C2-C 30 ) alkenylene or not substituted or substituted (C2-C 30 ) alkynylene, then L is bonded to any of the 3rd to 8th positions of phenanthrolinyl.

[0028] Formula HAr can be represented by any one of the following Formulas 1-1 to 1-5. [Chemical Formula]

[0029] In Formulas 1-1 to 1-5, X 11 ~X 20 each independently represents CR8 or N; R 12 and R 19 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cyanoalkyl, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; R5 to R8, R 13 ~R 18 , and R20 ~R 34 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C) 30 )alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30 ) Represents aryl, substituted or unsubstituted (3-30 member) heteroaryl, or L; One of R5 to R8 is L, and R 13 ~R 18 One of them is L, and R 20 ~R 25 One of them is L, and R 26 ~R 31 One of them is L, and R 32 ~R 34 One of them is L; L is defined as shown in Equation 1.

[0030] According to one embodiment of this disclosure, X 11 ~X 20 At least one of them is N. According to another embodiment of the present disclosure, X 11 ~X 20 Two or more of these are N. According to yet another embodiment of the present disclosure, X 11 ~X 15 One of the following is N, and X 16 ~X 20 One of the following is N. For example, X 11 or X 15 If N and X 16 or X 20 This is N.

[0031] According to one embodiment of this disclosure, R 12 and R 19 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 10 ) alkyl, or substituted or unsubstituted (C6~C 25 ) is aryl. According to another embodiment of the present disclosure, R 12 and R 19These are, independently, hydrogen, deuterium, an unsubstituted or deuterium-substituted (C1-C6) alkyl group, or an unsubstituted or deuterium-substituted (C6-C6) alkyl group. 18 ) is an aryl. For example, R 12 and R 19 These are, independently, hydrogen, deuterium, methyl, phenyl, pyridyl, etc., and these may be further substituted with deuterium.

[0032] According to one embodiment of this disclosure, R5~R8, R 13 ~R 18 , and R 20 ~R 34 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C6~C 18 )aryl, or L. According to one embodiment of the present disclosure, R5~R8, R 13 ~R 18 , and R 20 ~R 34 These are, independently, hydrogen, deuterium, and unsubstituted or deuterium-substituted (C6~C 12 ) Aryl, or L. For example, R5~R8, R 13 ~R 18 , and R 20 ~R 34 Each of these elements may independently be L, or hydrogen, deuterium, phenyl, naphthyl, biphenyl, etc., and these may be substituted with deuterium.

[0033] According to one embodiment of the present disclosure, one of R7 and R8 is L, and R 20 and R 23 ~R 25 One of them is L.

[0034] L is defined as shown in Equation 1.

[0035] -(L) a -HAr can be expressed by any one of the following equations 1-6 to 1-25. [ka] [ka] [ka]

[0036] In equations 1-6 to 1-25, X 11 ~X 20 Each of these independently represents CR8 or N; R5~R8 and R 12 ~R 34 These are, independently, hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C) 30 )alkyl, substituted or unsubstituted (C3~C 30 )Cycloalkyl, substituted or unsubstituted (C6~C 30 ) represents an aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; L and a are defined as in Equation 1.

[0037] According to one embodiment of this disclosure, R5~R8 and R 12 ~R 34 These are, independently, hydrogen, deuterium, substituted or unsubstituted (C1~C 10 ) alkyl, or substituted or unsubstituted (C6~C 25 ) is an arrow. According to another embodiment of the present disclosure, R5 to R8 and R 12 ~R 34 These are, independently, hydrogen, deuterium, an unsubstituted or deuterium-substituted (C1-C6) alkyl group, or an unsubstituted or deuterium-substituted (C6-C6) alkyl group. 18 ) are aryl. For example, R5~R8 and R 12 ~R 34 Each of these elements is independently selected from hydrogen, deuterium, methyl, phenyl, naphthyl, biphenyl, pyridyl, etc., and these may be substituted with deuterium.

[0038] The compound represented by Formula 1 may be at least one selected from the following compounds, but is not limited to them.

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[0039] In the above compound, D n This means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1, and the maximum value of n is the total number of hydrogen atoms that can be replaced in each compound.

[0040] The compounds represented by Formula 1 according to this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compounds of this disclosure can be prepared by referring to, but are not limited to, the following reaction schemes 1 to 6. [ka] [ka] [ka]

[0041] In the above reaction scheme, X1~X 10 , R1~R3, L, a, and R 12 ~R 19 As defined in Equations 1 and 1-1, X is N or CR, and each R is independently R 12As defined, n is an integer between 1 and 6. If n is an integer greater than or equal to 2, each of R may be the same or different from one another.

[0042] The organic electroluminescent compounds of this disclosure can be used in the N-type charge generation layer of an organic electroluminescent device.

[0043] The following describes an organic electroluminescent device using the aforementioned organic electroluminescent compound.

[0044] An organic electroluminescent element according to one embodiment comprises the organic electroluminescent compound of the present disclosure. According to one embodiment of the present disclosure, the organic electroluminescent compound can be used in an N-type charge generation layer and may be doped with an additional metal. According to one embodiment of the present disclosure, the metal includes Yb, Li, Cu, Ag, Au, Al, Mg, or any combination thereof.

[0045] An organic electroluminescent element according to one embodiment includes a plurality of light-emitting units disposed between a first electrode and a second electrode, and at least one charge-generating layer disposed between adjacent light-emitting units among the plurality of light-emitting units, wherein the charge-generating layer comprises the organic electroluminescent compound of the present disclosure. According to one embodiment of the present disclosure, at least one of the plurality of light-emitting units includes a first light-emitting layer and a second light-emitting layer adjacent to each other.

[0046] An organic electroluminescent compound according to one embodiment can 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 structures or stacked structures, depending on the arrangement of R (red), G (green) or YG (yellow-green), and B (blue) light-emitting units, or the CCM (color conversion material) method. Furthermore, an organic electroluminescent compound according to one embodiment can also be used in organic electroluminescent elements containing QDs (quantum dots).

[0047] One of the first and second electrodes may be an anode, and the other may be a cathode. In this case, the first and second electrodes may each be formed from a transparent conductive material, or from a translucent or reflective conductive material. Depending on the type of material forming the first and second electrodes, the organic electroluminescent element may be top-emission, bottom-emission, or double-sided emission.

[0048] An organic electroluminescent element according to one embodiment of the present disclosure may be an organic electroluminescent element having a tandem structure. In the case of a tandem organic electroluminescent element according to one embodiment, a single light-emitting unit (light-emitting unit) can be formed in a structure in which two or more units are connected by a charge-generating layer. The organic electroluminescent element 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. This may include a plurality of light-emitting units, each light-emitting unit 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, three or more light-emitting layers can be included in a light-emitting unit. The plurality of light-emitting units may emit the same color or different colors. Furthermore, a single light-emitting unit may include one or more light-emitting layers, and these layers may be the same or different colors. This may include one or more charge-generating layers placed between each light-emitting unit. A charge-generating layer is a layer that produces holes and electrons when a voltage is applied. If there are three or more light-emitting units, the charge-generating layers may be located between each light-emitting unit. In this case, the charge-generating layers may be the same or different from each other. By placing charge-generating layers between light-emitting units, the current efficiency in each light-emitting unit can be increased and the charge can be distributed smoothly. Specifically, the charge-generating layers can be placed between two adjacent stacks and help drive a tandem organic electroluminescent element using only anode-cathode pairs, without another internal electrode located between the stacks.

[0049] The charge generation layer may consist of an N-type charge generation layer and a P-type charge generation layer, and the N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof, and the alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may be made of a metal or organic material doped with a P-type dopant. For example, the metal may be made of one or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Furthermore, commonly used materials may be used as host materials for the P-type dopant and P-type doped organic material.

[0050] According to one embodiment, the present disclosure can provide a display device comprising an organic electroluminescent compound represented by Formula 1. In addition, by using the organic electroluminescent compound of the present disclosure, display devices such as smartphones, tablets, notebooks, PCs, and TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting can be manufactured.

[0051] The following describes the method for preparing organic electroluminescent compounds and their physical properties, as well as the driving voltage, current efficiency, and lifetime characteristics of OLEDs according to this disclosure. However, the following examples are provided solely to illustrate the properties of the compounds and OLEDs according to this disclosure for a more detailed understanding of this disclosure, and this disclosure is not limited to these examples. [Examples]

[0052] [Example 1] Synthesis of compound C-42 [ka] 4'-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2”-terpyridine (10.0 g, 23.0 mmol), 2-chloro-3-phenylquinoxaline (6.08 g, 25.3 mmol), Pd(PPh3)4 (1.33 g, 1.15 mmol), and K2CO3 (6.35 g, 45.9 mmol) were placed in toluene (115 mL), EtOH (23 mL), and distilled water (23 mL), and stirred under reflux at 100°C. After 17 hours, the mixture was cooled to room temperature, extracted with methylene chloride (MC), and then filtered through silica. The residue was then recrystallized to obtain compound C-42 (8.90 g, yield: 75.4%).

[0053] [Table 1]

[0054] [Example 2] Synthesis of Compound C-1 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (14.8 g, 41.1 mmol), 1,4-dibromonaphthalene (5.6 g, 19.6 mmol), Pd(PPh3)2Cl2 (1.38 g, 1.96 mmol), and K2CO3 (13.5 g, 97.9 mmol) were added to dimethylformamide (DMF, 112 mL) and distilled water (28 mL), and the mixture was stirred under reflux at 110°C. After 16 hours, the mixture was cooled to room temperature, followed by the addition of MeOH and stirring. The resulting precipitated solid was filtered. The residue was then filtered through silica and recrystallized to obtain compound C-1 (7.7 g, yield: 66.6%).

[0055] [Table 2]

[0056] [Example 3] Synthesis of compound C-873 [ka] 4'-Chloro-2,2':6',2”-terpyridine (3.0 g, 11.2 mmol), 2-ethynyl-9-phenyl-1,10-phenanthroline (3.46 g, 12.3 mmol), Pd(OAc)2 (0.50 g, 2.24 mmol), XPhos (2.1 g, 4.48 mmol), and CuI (0.21 g, 1.12 mmol) were added to DMF (150 mL) and triethylamine (TEA, 30 mL) and stirred at 80°C. After 20 hours, the mixture was cooled to room temperature, filtered through silica, and then recrystallized to obtain compound C-873 (1.5 g, yield: 26%).

[0057] [Table 3]

[0058] [Example 4] Synthesis of compound C-437 [ka] 6-Chloro-2,2':6',2”-terpyridine (9.0 g, 33.6 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (11 g, 28.0 mmol), Pd(amphos)Cl2 (1.38 g, 1.96 mmol), Aliquat336 (1.1 g, 2.80 mmol), and Na2CO3 (5.9 g, 56.0 mmol) were added to toluene (140 mL) and distilled water (45 mL), and the mixture was stirred under reflux at 120°C. After 16 hours, the mixture was cooled to room temperature, extracted by MC, and then filtered through silica. The residue was then recrystallized to obtain compound C-437 (3.3 g, yield: 24%).

[0059] [Table 4]

[0060] [Example 5] Synthesis of compound C-91 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (7.5 g, 20.9 mmol), 2-(3-chlorophenyl)-4-phenylquinazoline (6.6 g, 20.9 mmol), Pd(OAc)2 (0.24 g, 1.04 mmol), XPhos (1.0 g, 2.09 mmol), and K3PO4 (13 g, 62.6 mmol) were added to o-xylene (150 mL) and stirred at 120 °C. After 6 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The residue was then filtered through silica and recrystallized to obtain compound C-91 (3.5 g, yield: 33%).

[0061] [Table 5]

[0062] [Example 6] Synthesis of compound C-120 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (5.5 g, 15.3 mmol), 8-bromo-2,4-diphenylquinazoline (6.1 g, 16.8 mmol), Pd(PPh3)4 (2.6 g, 2.30 mmol), and K2CO3 (6.3 g, 45.9 mmol) were added to toluene (150 mL), EtOH (30 mL), and distilled water (30 mL), and the mixture was stirred under reflux at 100°C. After 17 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The residue was then filtered through silica and recrystallized to obtain compound C-120 (6.4 g, yield: 81%).

[0063] [Table 6]

[0064] [Example 7] Synthesis of Compound C-3 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (14 g, 38.9 mmol), 3-bromoiodobenzene (5.0 g, 17.7 mmol), Pd(PPh3)4 (1.6 g, 1.41 mmol), and K2CO3 (12 g, 88.4 mmol) were added to toluene (200 mL), EtOH (40 mL), and distilled water (40 mL), and the mixture was stirred under reflux at 100°C. After 16 hours, the mixture was cooled to room temperature, filtered through silica, and recrystallized to obtain compound C-3 (6.7 g, yield: 70%).

[0065] [Table 7]

[0066] [Example 8] Synthesis of compound C-294 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (5.5 g, 15.3 mmol), 5-bromo-2,9-diphenyl-1,10-phenanthroline (6.4 g, 15.6 mmol), Pd(PPh3)4 (0.89 g, 0.766 mmol), and K2CO3 (6.4 g, 45.9 mmol) were added to toluene (150 mL), EtOH (30 mL), and distilled water (30 mL), and the mixture was stirred under reflux at 100°C. After 24 hours, the mixture was cooled to room temperature, filtered through silica, and recrystallized to obtain compound C-294 (6.2 g, yield: 72%).

[0067] [Table 8]

[0068] [Example 9] Synthesis of compound C-762 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (21.8 g, 60.6 mmol), 1,3-dichloroisoquinoline (4.80 g, 24.2 mmol), Pd(PPh3)2Cl2 (1.19 g, 1.70 mmol), and K2CO3 (13.4 g, 96.9 mmol) were added to DMF (250 mL) and distilled water (50 mL), and the mixture was stirred under reflux at 120 °C. After 6 hours, the mixture was cooled to room temperature, EtOH (350 mL) was added, and the resulting solid was filtered. The residue was then filtered through silica and recrystallized to obtain compound C-762 (12.3 g, yield: 85.8%).

[0069] [Table 9]

[0070] [Example 10] Synthesis of compound C-366 [ka] 4'-(3-bromophenyl)-2,2':6',2”-terpyridine (7.00 g, 18.0 mmol), (9-(pyridin-2-yl)-1,10-phenanthroline-5-yl)boronic acid (6.51 g, 21.6 mmol), Pd(PPh3)4 (1.04 g, 0.901 mmol), and K2CO3 (7.48 g, 54.1 mmol) were added to toluene (150 mL), EtOH (30 mL), and distilled water (30 mL), and the mixture was stirred under reflux at 100°C. After 18 hours, the mixture was cooled to room temperature, extracted with dichloromethane (DCM), and then filtered through silica. The residue was then crystallized to obtain compound C-366 (4.5 g, yield: 44%).

[0071] [Table 10]

[0072] [Example 11] Synthesis of compound C-368 [ka] 4'-Chloro-2,2':6',2"-terpyridine (4.00 g, 15.0 mmol), (9-(pyridin-2-yl)-1,10-phenanthroline-5-yl)boronic acid (4.95 g, 16.4 mmol), Pd(OAc)2 (0.168 g, 0.747 mmol), SPhos (0.613 g, 1.49 mmol), and K2CO3 (6.20 g, 44.8 mmol) were added to tetrahydrofuran (THF, 150 mL) and distilled water (15 mL), and the mixture was stirred under reflux at 70°C. After 18 hours, the mixture was cooled to room temperature, and the resulting solid was filtered through silica. The residue was then crystallized to obtain compound C-368 (3.0 g, yield: 41%).

[0073] [Table 11]

[0074] [Example 12] Synthesis of compound C-665 [ka] 6-Chloro-2,2':6',2”-terpyridine (9.00 g, 33.6 mmol), 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (10.8 g, 28.0 mmol), Pd(amphos)Cl2 (1.40 g, 1.96 mmol), Aliquat336 (1.10 g, 2.80 mmol), and Na2CO3 (5.90 g, 56.0 mmol) were added to toluene (140 mL) and distilled water (45 mL) and stirred under reflux at 130°C. After 4 hours, the mixture was cooled to room temperature, extracted with DCM, and filtered through silica. The residue was then crystallized to obtain compound C-665 (3.0 g, yield: 22%).

[0075] [Table 12]

[0076] [Example 13] Synthesis of Compound C-8 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (15.5 g, 43.0 mmol), 2,6-dibromonaphthalene (6.0 g, 21.0 mmol), Pd(PPh3)2Cl2 (0.736 g, 1.05 mmol), and K2CO3 (8.70 g, 62.9 mmol) were added to DMF (150 mL) and distilled water (30 mL), and the mixture was stirred under reflux at 120 °C. After 18 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The residue was then filtered through silica and crystallized to obtain compound C-8 (6.6 g, yield: 53%).

[0077] [Table 13]

[0078] [Example 14] Synthesis of compound C-817 [ka] 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2':6',2”-terpyridine (15.0 g, 41.9 mmol), 2,4-dibromopyridine (4.4 g, 18.4 mmol), Pd(PPh3)2Cl2 (0.773 g, 1.11 mmol), and K2CO3 (12.7 g, 91.8 mmol) were added to DMF (200 mL) and distilled water (40 mL), and the mixture was stirred under reflux at 120°C. After 18 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The residue was then filtered through silica and crystallized to obtain compound C-817 (6.4 g, yield: 64%).

[0079] [Table 14]

[0080] [Examples 1-5 of the device] Fabrication of an organic electroluminescent device by depositing the compound according to the present disclosure as an N-type charge generation layer. An OLED was manufactured according to this disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (10Ω / □) (Geomatec Co., Ltd.) on a glass substrate for OLEDs was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Next, compound HI-1 was placed in one cell of the vacuum deposition apparatus, and compound HT-3 was placed in 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 HT-3 to form a hole injection layer with a thickness of 5 nm. Next, compound HT-3 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 30 nm. Next, compound HT-4 was introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate it, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After the formation of the hole injection layer and hole transport layer, a first light-emitting layer was deposited thereon as follows: Compound H-1 was introduced as a host into a vacuum deposition apparatus cell, and compound D-1 was introduced as a dopant into another cell. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 2 wt% based on the total amount of host and dopant, forming a first light-emitting layer with a thickness of 20 nm on the second hole transport layer. Next, compound ET-1 was deposited on the first light-emitting layer as a first hole blocking layer material with a thickness of 5 nm. Subsequently, compound ET-2 was deposited as an electron transport layer material with a thickness of 10 nm to form a first electron transport layer on the first hole blocking layer. Subsequently, lithium (Li) was deposited at an amount of 0.5 wt% on the compounds shown in Tables 1 and 2 below to form an N-type charge generation layer with a thickness of 4 nm on the first electron transport layer. Next, compound HI-1 was deposited at a doping amount of 6% by weight based on the total amount of compounds HI-1 and HT-3 to form a P-type charge generation layer with a thickness of 10 nm on the N-type charge generation layer. Compound HT-3 was deposited to a thickness of 30 nm to form a third hole transport layer, and then compound HT-4 was deposited to a thickness of 5 nm to form a fourth hole transport layer.Next, a second light-emitting layer was deposited on top of it as follows: Compound H-1 was introduced as a host into a cell of a vacuum deposition apparatus, and compound D-1 was introduced as a dopant into another cell. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 2% by weight relative to the total amount of host and dopant, forming a second light-emitting layer with a thickness of 20 nm on the fourth hole transport layer. Compound ET-1 was deposited on the second light-emitting layer to a thickness of 5 nm as a second hole blocking layer. Subsequently, compounds ET-2 and EI-1 were introduced into the two cells of the vacuum deposition apparatus, respectively, as second electron transport layer materials, and these two materials were deposited in a weight ratio of 2:1 to form a second electron transport layer with a thickness of 25 nm. Ytterbium (Yb) was deposited on the second electron transport layer to a thickness of 1 nm as an electron injection layer, and then an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum deposition apparatus. In this way, the OLED was manufactured. The amount of each compound used in all materials was 10. -6 It was purified by vacuum sublimation using a Thor device.

[0081] [Comparative Examples 1 and 2] Fabrication of organic electroluminescent elements by depositing conventional compounds as N-type charge generation layers. An OLED was manufactured using the same method as in Device Example 1, except that the compounds shown in Tables 1 and 2 below were used in the N-type charge generation layer.

[0082] The driving voltage, current efficiency, time required for the brightness to decrease from 100% to 95% at 2x acceleration (lifetime; T95), and the gradually increasing driving voltage change (ΔV) over 10 hours under 2x acceleration conditions at a brightness of 1,000 nits were measured for the organic electroluminescent elements manufactured in Element Examples 1-5 and Comparative Examples 1 and 2. The results are shown in Tables 1 and 2 below.

[0083] [Table 15]

[0084] [Table 16]

[0085] From Tables 1 and 2 above, it can be confirmed that the organic electroluminescent element using the organic electroluminescent compound according to this disclosure in the N-type charge generation layer exhibits a lower progressive drive voltage and / or higher current efficiency and / or longer lifetime characteristics compared to the case using conventional compounds.

[0086] [Element Example 6] Fabrication of an element for measuring lateral resistivity by depositing the compound according to the present disclosure as an N-type charge generation layer. An OLED was manufactured according to this disclosure. First, a transparent electrode indium tin oxide (ITO) thin film (Geomatec Co., Ltd.) on a glass substrate for OLEDs was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, 0.5% by weight, 1% by weight, or 2% by weight of Li was deposited onto the compounds shown in Table 3 below to form an N-type charge generation layer with a thickness of 100 nm. In this way, an element for measuring lateral resistivity was manufactured.

[0087] [Comparative Example 3] Fabrication of an element for lateral resistance measurement by depositing a conventional compound as an N-type charge generation layer. Except for using the compounds shown in Table 3 below in the N-type charge generation layer, an element for measuring lateral resistance was fabricated in the same manner as in Element Example 6.

[0088] The lateral resistivity of the elements manufactured in Element Example 6 and Comparative Example 3 was measured. The results are shown in Table 3 below.

[0089] The lateral resistivity was measured using a separately manufactured four-terminal resistometer for a device in which two previously unconnected electrodes were connected by co-depositing an N-type charge generating material and Li. High-precision resistivity was obtained by supplying current to one electrode and measuring the resistance generated by the current flowing from the opposite electrode.

[0090] [Table 17]

[0091] Transverse resistivity is a value that represents the resistance to leakage current in the N-type charge generation layer. The higher the transverse resistivity, the lower the transverse leakage current. From Table 3 above, it can be confirmed that the organic electroluminescent element using the organic electroluminescent compound according to this disclosure in the N-type charge generation layer exhibits a higher transverse resistivity compared to the case where conventional compounds are used. As a result, it can be seen that the current flowing unnecessarily in the transverse direction within the element is relatively suppressed, thereby improving the element's efficiency, such as current efficiency and lifespan.

[0092] [Examples 7 and 8 of the device] Fabrication of an organic electroluminescent device by depositing the compound according to the present disclosure as an N-type charge generation layer. An OLED was manufactured in the same manner as in Element Example 1, except that a first electron transport layer was deposited to a thickness of 12 nm, ytterbium (Yb) was deposited at a concentration of 2% by weight on the compounds shown in Table 4 below to form a 9 nm thick N-type charge generation layer on the first electron transport layer, and a 6 nm thick P-type charge generation layer was deposited on the N-type charge generation layer.

[0093] [Comparative Example 4] Fabrication of an organic electroluminescent device by depositing a conventional compound as an N-type charge generation layer. An OLED was manufactured in the same manner as in Element Example 7, except that the compounds shown in Table 4 below were used in the N-type charge generation layer.

[0094] The gradually increasing drive voltage change (ΔV) over 10 hours under 2x acceleration conditions was measured for the organic electroluminescent elements manufactured in Element Examples 7 and 8 and Comparative Example 4. The results are shown in Table 4 below.

[0095] [Table 18]

[0096] Table 4 above confirms that the organic electroluminescent element using the organic electroluminescent compound according to this disclosure in the N-type charge generation layer exhibits lower progressive drive voltage characteristics compared to the case using conventional compounds. As a result, the organic electroluminescent element according to this disclosure can be expected to exhibit excellent voltage stability, reduced power consumption, and long life characteristics.

[0097] [Example 9 of the device] Fabrication of an organic electroluminescent device by depositing the compound according to the present disclosure as an N-type charge generation layer. An OLED was manufactured using the same method as in Device Example 7, except that compound ET-3 was used as the first electron transport layer material, compound H-2-D17 was used as the host for the light-emitting layer, and ytterbium (Yb) was deposited on the compounds shown in Table 5 below to form an N-type charge generation layer.

[0098] [Comparative Example 5] Fabrication of an organic electroluminescent device by depositing a conventional compound as an N-type charge generation layer. An OLED was manufactured using the same method as in Device Example 9, except that the compounds shown in Table 5 below were used in the N-type charge generation layer.

[0099] The gradually increasing drive voltage change (ΔV) over 10 hours under 2x acceleration conditions was measured for the organic electroluminescent elements manufactured in Element Example 9 and Comparative Example 5. The results are shown in Table 5 below.

[0100] [Table 19]

[0101] Table 5 above confirms that the organic electroluminescent element using the organic electroluminescent compound according to this disclosure in the N-type charge generation layer exhibits lower gradually increasing drive voltage characteristics compared to the case using conventional compounds.

[0102] [Element Example 10] Fabrication of an Electron Driving Element by Depositing a Compound According to the Present Disclosure as an N-Type Charge Generation Layer An electron driving element according to the present disclosure was fabricated. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (manufactured by Diomatic Co., Ltd.) on a glass substrate for OLED was sequentially subjected to ultrasonic cleaning with acetone and isopropyl alcohol, and then stored in isopropyl alcohol and subsequently used. Next, the ITO substrate was attached to the substrate holder of a vacuum vapor deposition apparatus. Next, Compound EI-1 was introduced into the cell of a vacuum evaporation apparatus and evaporated to deposit a hole blocking layer. Thereafter, by depositing the compounds shown in Table 6 below alone, an N-type charge generation layer with a thickness of 30 nm was formed on the hole blocking layer. After ytterbium (Yb) was deposited with a thickness of 2 nm as an electron injection layer on the N-type charge generation layer, an Al cathode with a thickness of 80 nm was deposited on the electron injection layer by another vacuum evaporation apparatus. In this way, an electron driving element was fabricated. Each compound used for all the materials was purified by vacuum sublimation in 10 -6 torr. <00,00889> Separately, another electron driving element was fabricated in the same manner as described above, except that ytterbium (Yb) was deposited in an amount of 2 wt% on the compounds shown in Table 6 below to form an N-type charge generation layer.

[0104] [Comparative Example 6] Fabrication of an Electron Driving Element by Depositing a Conventional Compound as an N-Type Charge Generation Layer <00,00894>Electron driving elements were fabricated in the same manner as in Element Example 10, except that the compounds shown in Table 6 below were used for the N-type charge generation layer.

[0105] The driving voltages and the driving voltage difference (ΔV) at 100 mA / cm 2 for each of the electron driving elements including a metal undoped N-type charge generation layer and the electron driving element including an ytterbium-doped N-type charge generation layer fabricated in Element Example 10 and Comparative Example 6 were measured. The results are shown in Table 6 below.

[0106]

Table 20

[0107] From Table 6 above, it can be confirmed that in an electron driving element using the organic electroluminescence compound according to the present disclosure in the N-type charge generation layer, a significant difference in driving voltage is shown by metal doping as compared with the case of using a conventional compound. In addition, it can be confirmed that the stronger the driving voltage difference, the stronger the binding of the organic molecule to the metal.

[0108] The compounds used in the above-described Device Examples 1 to 10 and Device Comparative Examples 1 to 6 are shown in Table 7 below.

[0109]

Table 21

[0110] [[ID=,22]]

Table 22

Claims

1. Organic electroluminescent compounds represented by the following formula 1: 【Chemistry 1】 (In the formula, X １ ~X １０ Each of them is independently CR ４ Or it represents N; R １ to R ４ each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ to C ３０ )alkyl, substituted or unsubstituted (C ２ to C ３０ )alkenyl, substituted or unsubstituted (C ３ to C ３０ )cycloalkyl, substituted or unsubstituted (C ３ to C ３０ )cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or -(L) ａ -HAr; R １ ~R ４ At least one of them is -(L) ａ -HAr; R ２ ga- (L) ａ -If HAr, each R ４ This independently represents hydrogen, deuterium, or a cyano group; Each L is independently single-bonded, substituted, or unsubstituted (C ６ ~C ３０ ) Arylene, substituted or unsubstituted (C ２ ~C ３０ ) Alkenylene, substituted or unsubstituted (C ２ ~C ３０ ) represents alkynylene, or substituted or unsubstituted (3-30 member) heteroarylene; a is an integer of 1 or 2, and if a is 2, L may be the same as or different from the other; HAr represents a substituted or unsubstituted (3-30 member) heteroaryl compound containing at least one nitrogen atom; However, R ２ ga- (L) ａ -HAr is a case where HAr is a substituted or unsubstituted phenanthrolinyl, and L is a substituted or unsubstituted (C ２ ~C ３０ ) Alkenylene or substituted or unsubstituted (C ２ ~C ３０ (If it is not an alkynylene, L is attached to any of the 3-8 positions of phenanthrolinyl.)

2. The substituted alkyl, the substituted alkenyl(ene), the substituted alkynyl(ene), the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted cycloalkenyl, and the substituted heterocycloalkyl are each independently of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C １ ~C ３０ ) alkyl, halo(C １ ~C ３０ ) alkyl, (C ２ ~C ３０ ) Alkenil, (C ２ ~C ３０ ) Alkinyl, (C １ ~C ３０ ) Alkoxy, (C １ ~C ３０ ) alkylthio, (C ３ ~C ３０ ) Cycloalkyl, (C ３ ~C ３０ ) Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C ６ ~C ３０ ) Aryloxy, (C ６ ~C ３０ ) Arylthio, (3-membered to 30-membered) heteroaryl, (C ６ ~C ３０ ) Ariel, Tori (C １ ~C ３０ ) Alkylsilyl, tri(C ６ ~C ３０ ) Aryl silyl, di(C １ ~C ３０ ) Alkyl (C ６ ~C ３０ ) Aryl silyl, (C １ ~C ３０ ) Alkyl di(C ６ ~C ３０ ) Aryl silyl, (C ３ ~C ３０ ) Aliphatic rings and (C ６ ~C ３０ ) A fused ring group with an aromatic ring, amino, mono or di(C) １ ~C ３０ ) Alkylamino, mono or di(C ６ ~C ３０ ), arylamino, (C １ ~C ３０ ), alkyl (C ６ ~C ３０ ), arylamino, mono- or di(3- to 30-membered) heteroarylamino, (C １ ~C ３０ ), alkyl(3- to 30-membered) heteroarylamino, (C ６ ~C ３０ ), aryl(3- to 30-membered) heteroarylamino, (C １ ~C ３０ ), alkylcarbonyl, (C １ ~C ３０ ), alkoxycarbonyl, (C ６ ~C ３０ ), arylcarbonyl, (C ６ ~C ３０ ), arylphosphinyl, di(C ６ ~C ３０ ), arylboronyl, di(C １ ~C ３０ ), alkylboronyl, (C １ ~C ３０ ), alkyl(C ６ ~C ３０ ), arylboronyl, (C ６ ~C ３０ ), ar(C １ ~C ３０ ), alkyl, (C １ ~C ３０ ), alkyl(C ６ ~C ３０ ), aryl, and at least one selected from the group consisting of combinations thereof, the organic electroluminescent compound according to claim 1.

3. The organic electroluminescent compound according to claim 1, wherein the HAr is represented by any one of the following formulas 1-1 to 1-5. 【Chemistry 2】 (In the formula, X １１ ~X ２０ Each of them is independently CR ８ Or it represents N; R １２ and R １９ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C ６ ~C ３０ ) represents an aryl, or a substituted or unsubstituted (3-30 member) heteroaryl; R ５ ~R ８ , R １３ ~R １８ , and R ２０ ~R ３４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C ６ ~C ３０ ) Represents aryl, substituted or unsubstituted (3-30 member) heteroaryl, or L; R ５ ~R ８ One of them is L, and R １３ ~R １８ One of them is L, and R ２０ ~R ２５ One of them is L, and R ２６ ~R ３１ One of them is L, and R ３２ ~R ３４ One of them is L; L is as defined in claim 1).

4. Said - (L) ａ The organic electroluminescent compound according to claim 1, wherein -HAr is represented by any one of the following formulas 1-6 to 1-25. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 (In these formulas, X １１ ~X ２０ Each of them is independently CR ８ Or it represents N; R ５ ~R ８ and R １２ ~R ３４ Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ３ ~C ３０ ) Cycloalkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3-30 member) heteroaryl; L and a are as defined in claim 1).

5. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds: 【Transformation 6】 【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】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 (In the above compound, D ｎ This means that n hydrogen atoms are replaced by deuterium, where n is an integer greater than or equal to 1, and the maximum value of n is the total number of hydrogen atoms that can be replaced in each compound.

6. The organic electroluminescent compound according to claim 1, used in an N-type charge generation layer.

7. An organic electroluminescent element comprising the organic electroluminescent compound described in claim 1.

8. The organic electroluminescent element according to claim 7, wherein the organic electroluminescent compound is used in an N-type charge generation layer and is doped with an additional metal.

9. The organic electroluminescent element according to claim 8, wherein the metal comprises Yb, Li, Cu, Ag, Au, Al, Mg, or any combination thereof.

10. An organic electroluminescent element comprising a plurality of light-emitting units disposed between a first electrode and a second electrode, and at least one charge-generating layer disposed between adjacent light-emitting units among the plurality of light-emitting units, wherein the charge-generating layer comprises the organic electroluminescent compound described in claim 1.

11. The organic electroluminescent element according to claim 10, wherein at least one of the plurality of light-emitting units includes a first light-emitting layer and a second light-emitting layer adjacent to each other.

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