Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

Provided are an organic electroluminescent compound and an organic electroluminescent device comprising the same.SOLUTION: The present disclosure relates to an organic electroluminescent compound represented by formula 1, an organic electroluminescent material, an N-type charge generation material, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound, the organic electroluminescent material, or the N-type charge generation material of the present disclosure, an organic electroluminescent device having improved luminous efficiency and / or lifespan characteristics may be provided.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] A green-emitting TPD / Alq3 bilayer small molecule organic electroluminescent device (OLED), consisting of an emissive layer and a charge transport layer, was first developed by Tang et al. at Eastman Kodak in 1987. Since then, research on organic electroluminescent devices has progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials, which have excellent luminous efficiency in panel packaging. High OLED efficiency is still required for many applications, such as TVs and lighting. OLEDs with long-life characteristics are required for long-term use and high display resolution.

[0003] Although U.S. Patent No. 5,629,999 discloses phenanthroline derivatives, it does not specifically disclose the specific compounds claimed in the present disclosure. Additionally, there is a continuing need to develop luminescent materials that exhibit improved performance, such as improved drive voltage, luminous efficiency, power efficiency, and / or lifetime characteristics, compared to previously disclosed compounds. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Korean Patent Application Publication No. 2027-0105040 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present disclosure is to provide organic electroluminescent compounds having novel structures suitable for use in organic electroluminescent devices. Another object of the present disclosure is to provide organic electroluminescent devices exhibiting high luminous efficiency and / or long life characteristics. A further object of the present disclosure is to provide organic electroluminescent materials or N-type charge generating materials that can be used to fabricate organic electroluminescent devices having high luminous efficiency and / or improved life characteristics. [Means for solving the problem]

[0006] As a result of intensive research to solve the technical problems, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 1, and an organic electroluminescent material, an N-type charge generating material, and an organic electroluminescent device containing the same: [ka] In Equation 1, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 30 ) alkyl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; R2 to R8 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 (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) a substituted or unsubstituted fused ring group with an aromatic ring, or HAr defined by the following formula 1-a, or may be linked to adjacent substituents to form a ring, Provided that at least one of R2 to R8 is represented by HAr defined in Formula 1-a, [ka] In the formula, X1 to X4 each independently represent N or CR9; L is a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30-membered) heteroarylene; R9~R 11 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 (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted fused ring group with an aromatic ring, or may be bonded to L or may be linked to adjacent substituents to form a ring; a represents an integer of 1 to 4, b represents an integer of 1 or 2, and when a and b are integers of 2 or greater, each a and each b may be the same as or different from each other; However, when R8 in Formula 1 is HAr and at least one of X1 to X4 in Formula 1-a is N, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

[0007] Advantageous Effects of the Invention The organic electroluminescent compound according to the present disclosure exhibits suitable performance for use in organic electroluminescent devices.In addition, by including the compound according to the present disclosure as an organic electroluminescent material or an N-type charge generating material, it is possible to provide an organic electroluminescent device that exhibits higher luminous efficiency and / or improved life characteristics compared with conventional organic electroluminescent devices, and to use it to manufacture a display device or a lighting device. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present disclosure will be described in detail below. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.

[0009] The "organic electroluminescent compound" in the present disclosure is a compound that can be used in an organic electroluminescent device and can be included in any material layer that constitutes the organic electroluminescent device as needed.

[0010] In the present disclosure, the "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device and can contain at least one compound. The organic electroluminescent material can be included in any layer constituting an organic electroluminescent device, as needed. For example, the organic electroluminescent material can 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, an auxiliary light-emitting material, an electron blocking material, a light-emitting 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, etc.

[0011] In this specification, "(C1 to C 30 The term "(C3-C) alkyl" means a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, and the number of carbon atoms here is preferably 1 to 20, more preferably 1 to 10. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. 30 The term "(3- to 7-membered)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. In the present disclosure, the term "(3- to 7-membered)heterocycloalkyl" is intended to refer to a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent having 3 to 7, preferably 5 to 7, skeletal ring atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of O, S, and N. Examples of the heterocycloalkyl include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like.

[0012] In this disclosure, "(C6-C 30 ) aryl" or "(C6-C 30"Arylene" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, which may be partially saturated. The number of ring skeletal carbon atoms is preferably 6 to 20, more preferably 6 to 15. The aryl may include a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzoanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluoren]yl, spiro[fluorene-benzofluoren]yl, azulenyl, and tetramethyl-dihydrophenanthrenyl. Specific examples of aryl 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-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoran thenyl, 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 benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 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-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 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[Pc]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,Examples include 10-dihydro-4-phenanthrenyl.

[0013] In the present disclosure, a "(3- to 30-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" refers to an aryl or arylene group having 3 to 30 ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P. The number of ring skeletal atoms here 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 or aryl group to a heteroaryl group via a single bond, which may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinoline, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzo thienopyrimidinyl, naphthienopyrimidinyl, pyrimidoindolyl, benzopyrimidindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl,Examples of fused ring heteroaryls include indolizinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolyl, thiochromenoquinazolyl, dimethylbenzopyrimidinyl, indolocarbazolyl, and indenocarbazolyl. More specifically, heteroaryl includes 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizinyl, 2-indolizinyl, 3-indolizinyl, 5-indolizinyl, Indolyl, 6-indolizinyl, 7-indolizinyl, 8-indolizinyl, 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, 2-furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-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-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3- Furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl butyl-1-indolyl, 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]-benzo furanyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2,3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl,6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho- [2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophenyl, 4-naphtho-[1,2-b]-benzothiophenyl, 5-naphtho-[1,2-b]-benzothiophenyl, 6-naphtho-[1,2-b]-benzothiophenyl, 7-naphtho-[1,2-b]-benzothiophenyl , 8-naphtho-[1,2-b]-benzothiophenyl, 9-naphtho-[1,2-b]-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-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl,8-Benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-dβ]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-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio Examples include thio[3,2-d]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. Furthermore, "heteroaryl(ene)" can be classified into heteroaryl(ene)s having electronic properties and heteroaryl(ene)s having hole properties. Heteroaryl(ene)s with electronic properties are those in which the parent nucleus is a relatively electron-rich substituent, 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(ene)s with electron hole properties are those in which the parent nucleus is a relatively electron-poor substituent, such as substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0014] In this specification, "(C3 to C 30 ) aliphatic ring and (C6~C 30The term "fused ring group with an aromatic ring" refers to a functional group in which at least one aliphatic ring having 3 to 30 ring skeletal carbon atoms, preferably 3 to 25 ring skeletal carbon atoms, and more preferably 3 to 18 ring skeletal carbon atoms, is fused with at least one aromatic ring having 6 to 30 ring skeletal carbon atoms, preferably 6 to 25 ring skeletal carbon atoms, and more preferably 6 to 18 ring skeletal carbon atoms. Specific examples of the fused ring group include a fused ring group of one or more benzenes and one or more cyclohexanes, or a fused ring group of one or more naphthalenes and one or more cyclopentanes. In the present specification, the term "(C3 to C 30 ) aliphatic ring and (C6~C 30 ) The carbon atoms of the fused ring group with the aromatic ring may be substituted with one or more heteroatoms selected from B, N, O, S, Si, and P, preferably one or more heteroatoms selected from N, O, and S. As used herein, "halogen" includes F, Cl, Br, and I.

[0015] Additionally, "ortho- (o-)," "meta- (m-)," and "para- (p-)" are prefixes that indicate the relative positions of the substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other; for example, when two substituents of a benzene derivative occupy the 1st and 2nd positions, this is called the "ortho-" configuration. The prefix "meta-" indicates that two substituents are at the 1st and 3rd positions; for example, when two substituents of a benzene derivative occupy the 1st and 3rd positions, this is called the "meta-" configuration. The prefix "para-" indicates that two substituents are at the 1st and 4th positions; for example, when two substituents of a benzene derivative occupy the 1st and 4th positions, this is called the "para-" configuration.

[0016] As used herein, the phrase "a ring formed by the joining of adjacent substituents" means that at least two adjacent substituents are joined or fused together to form a substituted or unsubstituted, monocyclic or polycyclic (3- to 30-membered) alicyclic ring or aromatic ring, or a combination thereof. Preferably, the ring may be a substituted or unsubstituted, monocyclic or polycyclic (5- to 25-membered) alicyclic ring or aromatic ring, or a combination thereof. In addition, the ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. In one embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 20, while in another embodiment of the present disclosure, the number of ring skeletal atoms is 5 to 15. For example, the fused ring may be in the form of a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0017] As used herein, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group (i.e., a substituent), including substitution with a group to which two or more substituents are linked. Unless otherwise specified, a substituent may replace a hydrogen atom at any location where the substituent can be substituted without limitation, and when two or more hydrogen atoms in a specific functional group are each replaced with a substituent, the substituents may be the same or different from each other. The maximum number of substituents that can be substituted for a certain functional group can be the total number of valences that can be substituted for each atom forming the functional group. In this specification, substituted phenyl, substituted biphenyl, substituted terphenyl, substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted fused ring groups of an aliphatic ring and an aromatic ring each independently represent deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C 30 ) Alkyl, halo (C1-C 30 ) Alkyl, (C2-C 30 ) alkenyl, (C2-C 30 ) alkynyl, (C1-C 30 ) alkoxy, (C1-C 30 ) Alkylthio, (C3-C 30 ) cycloalkyl, (C3-C 30 ) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C 30 ) Aryloxy, (C6-C 30 ) arylthio, unsubstituted or (C6-C 30 ) aryl-substituted (5-30 membered) heteroaryl, unsubstituted or (5-30 membered) heteroaryl-substituted (C6-C 30 ) aryl, tri(C1-C 30 ) Alkylsilyl, Tri(C6-C 30 ) arylsilyl, di(C1-C 30) Alkyl (C6-C 30 ) arylsilyl, (C1-C 30 ) Alkyldi(C6~C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) condensed ring group with an aromatic ring, amino, mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di-(C6-C 30 ) alkylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, substituted or unsubstituted (C1-C 30 ) alkyl (3 to 30 membered) heteroaryl amino, substituted or unsubstituted (C6 to C 30 ) aryl(3 to 30 membered)heteroarylamino, (C1 to C 30 ) alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, (C6-C 30 ) arylphosphinyl, di(C6-C 30 ) arylboronyl, di(C1-C 30 ) alkylboronyl, (C1-C 30 ) Alkyl (C6-C 30 ) arylboronyl, (C6-C 30 ) Aryl (C1-C 30 ) alkyl, (C1-C 30 ) Alkyl (C6-C 30 ) aryl, and combinations thereof. According to one embodiment of the present disclosure, the substituent may be deuterium.

[0018] In this disclosure, if a substituent is not shown in a chemical formula or compound structure, it can mean that all positions where a substituent can exist are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, in which case the deuterium content can be 0% to 100%. In this disclosure, if a substituent is not shown in a chemical formula or compound structure, it can mean that hydrogen and deuterium are mixed in the compound unless a substituent is explicitly excluded, such as 0% deuterium, 100% hydrogen, or all substituents are hydrogen. Deuterium is an isotope of hydrogen and is an element with 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 can be thought of as atoms with the same atomic number (Z) but different mass numbers (A), or elements with the same number of protons but different numbers of neutrons.

[0019] In this disclosure, "combinations thereof" refers to the combination of one or more elements from the corresponding list to form a known or chemically stable configuration that one skilled in the art can envision from the corresponding list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl can combine to form a halogenated alkyl substituent; halogen, alkyl, and aryl can combine to form a halogenated arylalkyl. For example, preferred combinations of substituents may include up to 50 atoms that are not hydrogen or deuterium, or up to 40 atoms that are not hydrogen or deuterium, or up to 30 atoms that are not hydrogen or deuterium, or in many cases, preferred combinations of substituents may include up to 20 atoms that are not hydrogen or deuterium.

[0020] In the formulae of the present disclosure, when 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] Compounds of formula 1 are described in more detail as follows.

[0022] In Formula 1, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 30 ) alkyl, or substituted or unsubstituted (3-30 membered) heteroaryl. - According to one embodiment of the present disclosure, R1 is hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C 20 ) alkyl, or substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment of the present disclosure, R1 represents hydrogen, deuterium, halogen, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, unsubstituted or deuterium-substituted terphenyl, unsubstituted or deuterium-substituted (C1-C6) alkyl, or unsubstituted or deuterium-substituted (5-25 membered) heteroaryl. For example, R1 represents hydrogen, deuterium, fluoro, methyl, phenyl, o-biphenyl, m-biphenyl, p-biphenyl, pyridyl, etc., which may be substituted with one or more deuterium atoms.

[0023] In Formula 1, R2 to R8 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 (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) aromatic ring, or HAr defined by the following formula 1-a, or may be linked to adjacent substituents to form a ring, provided that at least one of R2 to R8 is represented by HAr defined by formula 1-a. According to one embodiment of the present disclosure, R2 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, or HAr as defined by the following formula 1-a. According to another embodiment of the present disclosure, R2 to R8 each independently represent hydrogen, deuterium, phenyl, pyridyl, etc., or HAr as defined by the following formula 1-a, which may be substituted with one or more deuterium atoms. [ka]

[0024] In formula 1-a, X1 to X4 each independently represent N or CR9. According to one embodiment of the present disclosure, at least one of X1 to X4 is N. According to another embodiment of the present disclosure, at least one or two of X1 to X4 are N.

[0025] In formula 1-a, L is a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene. According to one embodiment of the present disclosure, L represents a single bond, a substituted or unsubstituted (C6 to C 25) arylene, or substituted or unsubstituted (5-20 membered) heteroarylene. According to another embodiment of the present disclosure, L represents a single bond, or an unsubstituted or deuterium-substituted (C6-C 18 ) arylene. For example, L may be a single bond, phenylene, naphthylene, etc., which may be substituted with one or more deuterium atoms.

[0026] In formula 1-a, R9 to R 11 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 (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) represents a substituted or unsubstituted fused ring group with an aromatic ring, or may be bonded to L or may be linked to adjacent substituents to form a ring. According to one embodiment of the present disclosure, X9 to X 11 One of them is bound to L, and the remaining X9 to X 11 are each independently hydrogen, deuterium, substituted or unsubstituted (C1 to C 20 ) alkyl, substituted or unsubstituted (C6-C 25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl. According to another embodiment of the present disclosure, R to R 11 One of them is bonded to L, and the remaining R9 to R 11 are each independently hydrogen, deuterium, unsubstituted or deuterium-substituted (C1-C 10 ) alkyl, or unsubstituted or deuterium-substituted (C6-C 18 For example, R can be hydrogen, deuterium, methyl, phenyl, etc., which may be substituted with one or more deuterium atoms; R 10 and R 11 may each independently be hydrogen or deuterium, and R to R 11 One of may be attached to L.

[0027] In formula 1-a, a represents an integer of 1 to 4, and b represents an integer of 1 or 2. When a and b are integers of 2 or greater, each a and each b may be the same or different.

[0028] However, when R8 in Formula 1 is HAr and at least one of X1 to X4 in Formula 1-a is N, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C 30 ) alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

[0029] Formula 1 can be expressed by at least one of the following formulas 1-1 to 1-7: [ka]

[0030] In formulas 1-1 to 1-7, R1 and HAr are as defined in formula 1.

[0031] In formulas 1-1 to 1-7, R2 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 to C30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl. For example, R2 to R8 each independently represent hydrogen, deuterium, phenyl, pyridyl, etc., which may be substituted with one or more deuterium atoms.

[0032] Formula 1-a is represented by the following formulas 1-a-1 to 1-a-10: [ka] can be represented by at least one of:

[0033] In formulas 1-a-1 to 1-a-10, R 10 , R 11 , L, X1 to X4, a, and b are as defined in formula 1-a.

[0034] The organic electroluminescent compound represented by Formula 1 may be, but is not limited to, at least one selected from the group consisting of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0035] In the above compound, D nmeans that n hydrogen atoms are replaced with deuterium atoms, where n is an integer between 1 and the maximum number of hydrogen atoms in the compound. Specifically, n is an integer that is at least 1 and at most the maximum number of hydrogen atoms in the compound.

[0036] According to one embodiment of the present disclosure, when the compound represented by Formula 1 contains deuterium, the deuterium substitution rate is preferably about 100% or less, more preferably about 95% or less, even more preferably about 90% or less, and even more preferably about 85% or less of the total number of hydrogen atoms. The compound of Formula 1 substituted with the above deuterium substitution rate can increase the stability of the compound due to the increase in bond dissociation energy caused by deuteration, and the organic electroluminescent device containing this compound can exhibit improved light-emitting properties.

[0037] The compound represented by Formula 1 can be produced by a synthetic method known to those skilled in the art. For example, the compound of the present disclosure can be synthesized with reference to, but not limited to, the following Reaction Scheme 1. Reaction Scheme 1 [ka]

[0038] In Reaction Scheme 1, R2 to R8, R 10 , R 11 , X1 to X4, L, a, and b are as defined in formula 1.

[0039] The present invention provides an organic electroluminescent material, an N-type charge generating material, or an organic electroluminescent device comprising the above compound.

[0040] An organic electroluminescent device according to one embodiment of the present disclosure includes a first electrode, a second electrode, a plurality of light-emitting units disposed between the first electrode and the second electrode, and at least one charge-generating layer disposed between adjacent light-emitting units of the plurality of light-emitting units, and the charge-generating layer may include a compound represented by Formula 1.

[0041] An organic electroluminescent device according to an 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 an embodiment, a single light-emitting unit (light-emitting portion) may be formed by connecting two or more units via 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 an emitting layer emitting light in a specific wavelength range stacked between the first and second electrodes. It may include multiple light-emitting units, each of which may include a hole-transporting zone, an emitting layer, and an electron-transporting zone. The hole-transporting zone may include a hole-injection layer and a hole-transporting layer, and the electron-transporting zone may include an electron-transporting layer and an electron-injection layer. According to an embodiment of the present disclosure, three or more light-emitting layers may be included in the light-emitting unit. The multiple light-emitting units may emit the same color or different colors. In addition, one light-emitting unit can include one or more light-emitting layers, which can be of the same color or different colors, and which can include one or more charge-generating layers disposed between each light-emitting unit.

[0042] The charge generation layer refers to a layer in which holes and electrons are generated when a voltage is applied. When three or more light-emitting units are present, a charge generation layer can be disposed between each light-emitting unit. The charge generation layers can be the same or different from one another. By disposing a charge generation layer between the light-emitting units, the current efficiency in each light-emitting unit can be increased and charge can be smoothly distributed. Specifically, a charge generation layer can be disposed between two adjacent stacks, which can be useful for driving a tandem organic electroluminescent device using only an anode and a cathode pair without a separate internal electrode disposed between the stacks. The charge generation layer can be composed of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer can include a compound represented by Formula 1 of the present disclosure. The P-type charge generation layer can be made of a metal or organic material doped with a p-type dopant. For example, the metal can be made of one or an alloy of two or more selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, materials commonly used as P-type dopants and host materials for P-type doped organic materials can be used.

[0043] An organic electroluminescent device according to another embodiment of the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, the organic layer including a hole transport layer, an emitting layer, a hole auxiliary layer, an electron blocking layer, a charge generating layer, and an emitting auxiliary layer. According to one embodiment of the present disclosure, at least one of the hole transport layer, the emitting layer, the hole auxiliary layer, the electron blocking layer, the charge generating layer, and the emitting auxiliary layer may include a compound represented by Formula 1. For example, the charge generating layer may include a compound represented by Formula 1. According to one embodiment of the present disclosure, the organic electroluminescent material of the present disclosure includes at least one compound selected from Compounds C-1 to C-120, and the organic electroluminescent material may be included in the same organic layer, for example, the charge generating layer.

[0044] In addition to the hole transport layer, light-emitting layer, hole auxiliary layer, electron blocking layer, charge generating layer, and light-emitting auxiliary layer, the organic layer may further include at least one layer selected from the group consisting of a hole injection layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron buffer layer. The organic layer may further include an amine-based compound and / or an azine-based compound in addition to the compound of the present disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may contain an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound, as the hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, and electron blocking material. Furthermore, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may contain an azine-based compound as the electron transport material, electron injection material, electron buffer material, and hole blocking material. Furthermore, the organic material layer may further include at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of Periodic Table, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic d-transition elements of the periodic table, or at least one complex compound containing such a metal.

[0045] The compound according to an embodiment of the present disclosure can be used as an emitting material for a white organic light-emitting device. White organic light-emitting devices have been proposed to have various structures, such as a side-by-side arrangement method, a stacked arrangement method, or a color conversion material (CCM) method, depending on the arrangement of R (red), G (green) or YG (yellow-green), and B (blue) light-emitting units. In addition, the organic electroluminescent compound according to an embodiment of the present disclosure can also be used in an organic electroluminescent device containing quantum dots (QDs).

[0046] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The first electrode and the second electrode can be formed of a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. The organic electroluminescent device can be a top-emitting, bottom-emitting, or double-sided emitting type depending on the type of material forming the first electrode and the second electrode.

[0047] The light-emitting layer may include one or more hosts and one or more dopants. The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, and is preferably a phosphorescent dopant.

[0048] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multi-layered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two types of compounds may be used simultaneously in each of the multi-layered layers. In addition, the hole injection layer may be further doped with a p-dopant. The electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and by preventing electrons from overflowing from the light-emitting layer, it can confine excitons within the light-emitting layer and prevent light leakage. The hole transport layer or electron transport layer may also be multi-layered, and in this case, multiple compounds may be used in each of the multi-layered layers.

[0049] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination 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 interface properties between the light-emitting layer and the electron injection layer, and two types of compounds may be used simultaneously in each of the multiple layers. A hole blocking layer may be disposed 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 and hole recombination in the light-emitting layer. The hole blocking layer or electron transport layer may also be multilayered, and in this case, multiple compounds may be used in each layer. The electron injection layer may also be doped as an n-dopant.

[0050] The light-emitting auxiliary layer may be a layer disposed between the anode and the light-emitting layer, between the cathode and the light-emitting layer, or between the cathode and the light-emitting layer. When disposed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote hole injection and / or hole transport or to block electron overflow. When disposed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote electron injection and / or electron transport or to block hole overflow. In addition, a hole auxiliary layer disposed between the hole transport layer (or hole injection layer) and the light-emitting layer can promote or block the hole transport rate (or hole injection rate), thereby adjusting the charge balance. When an organic electroluminescent device includes two or more hole transport layers, the additional hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer can improve the efficiency and / or life of the organic electroluminescent device.

[0051] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as a "surface layer") is preferably disposed on the inner surface of at least one of the pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface on the electroluminescent medium layer side, and a metal halide layer or metal oxide layer is preferably disposed 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), SiON, SiAlON, etc., preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0052] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant can be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, thereby making it easier to inject and transport electrons from the mixed region to the emissive medium. Furthermore, the hole transport compound is oxidized to a cation, thereby making it easier to inject and transport holes from the mixed region to the emissive medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds, and preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using a reductive dopant layer as a charge generating layer, an organic electroluminescent device having at least two emissive layers and emitting white light can be produced.

[0053] According to one embodiment, the present disclosure can provide a display device comprising a compound represented by Formula 1. In addition, the organic electroluminescent device of the present disclosure can be used to manufacture display devices such as smartphones, tablets, notebooks, PCs, TVs, or car display devices, or lighting devices such as outdoor or indoor lighting.

[0054] The preparation method of the organic electroluminescent compound of the present disclosure and its physical properties and the driving voltage, current efficiency and lifespan properties of the OLED of the present disclosure will be described in detail below.However, the following examples only describe the properties of the compound of the present disclosure and the OLED, and the present disclosure is not limited to the following examples. [Example]

[0055] Example 1: Preparation of Compound C-5 [ka] 2-Phenyl-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (20.0 g, 43.6 mmol), 2-chloro-3-phenylbenzo[f]quinazoline (12.7 g, 43.6 mmol), Pd(Amphos)Cl (2.2 g, 3.1 mmol), aliquat 336 (1.8 g, 4.4 mmol), and NaCO (9.2 g, 87 mmol) were dissolved in 220 mL of toluene and 75 mL of HO. The mixture was then stirred at 130 °C under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated. The residue was then purified by column chromatography to give compound C-5 (12.5 g, yield: 49%).

[0056] [Table 1]

[0057] Example 2: Preparation of Compound C-2 [ka] 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (10.0 g, 26.2 mmol), 2-chloro-3-phenylbenzo[f]quinoxaline (9.1 g, 31.4 mmol), Pd(Amphos)Cl (1.3 g, 1.8 mmol), aliquot 336 (1.1 g, 2.6 mmol), and NaCO (5.5 g, 52.3 mmol) were dissolved in 130 mL of toluene and 45 mL of HO. The mixture was then stirred at 130 °C under reflux for 3 h. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was separated. The residue was then purified by column chromatography to give compound C-2 (7.3 g, 54% yield).

[0058] [Table 2]

[0059] Example 3: Preparation of Compound C-9 [ka] 2-Phenyl-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (10.0 g, 21.8 mmol), 2-chloro-4-phenylbenzo[h]quinazoline (7.6 g, 26 mmol), Pd(Amphos)Cl (1.1 g, 1.5 mmol), aliquot 336 (0.9 g, 2.2 mmol), and NaCO (4.6 g, 44 mmol) were dissolved in 110 mL of toluene and 36 mL of HO. The mixture was then stirred at 130 °C under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was separated. The residue was then purified by column chromatography to give compound C-9 (7.1 g, 55% yield).

[0060] [Table 3]

[0061] Example 4: Preparation of Compound C-10 [ka] 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthroline (19.1 g, 50 mmol), 2-chloro-4-phenylbenzo[h]quinazoline (14.5 g, 50 mmol), Pd(PPh3)4 (2.9 g, 2.5 mmol), and K2CO3 (17.3 g, 125 mmol) were dissolved in 200 mL of toluene, 50 mL of EtOH, and 50 mL of HO. The mixture was then stirred at 130 °C under reflux for 18 h. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was separated. The residue was then purified by column chromatography to give compound C-10 (22.0 g, 86% yield).

[0062] [Table 4]

[0063] Device Examples 1-4: Fabrication of OLEDs Comprising Compounds According to the Present Disclosure in an N-Type Charge Generating Layer An OLED according to the present disclosure was fabricated. First, a transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was attached to a substrate holder in a vacuum evaporation system. Compound HI-1 was introduced into one cell of the vacuum evaporation system, and compound HT-3 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 compounds HI-1 and HT-3 to form a hole injection layer with a thickness of 5 nm. Compound HT-3 was then deposited on the hole injection layer to form a first hole transport layer with a thickness of 30 nm. Compound HT-4 was then introduced into another cell of the vacuum evaporation system and evaporated by passing a current through the cell, thereby depositing a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, a first emissive layer was deposited thereon as follows: Compound H-1 was introduced as a host into one 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 wt % based on the total amount of the host and dopant to form a first emissive layer with a thickness of 20 nm on the second hole transport layer. Next, Compound ET-1 was deposited to a thickness of 5 nm on the first emissive layer as a first hole blocking layer material. Compound ET-2 was then deposited to a thickness of 10 nm on the first electron transport layer material to form a first electron transport layer. Subsequently, 0.5 wt % of Li (lithium) was deposited on the N-type charge generation layer compounds listed in Table 1 to form an N-type charge generation layer with a thickness of 4 nm. Next, compound HI-1 was doped at a doping amount of 6 wt% based on the total amount of compounds HI-1 and HT-3 to form a 10 nm thick P-type charge generation layer. Compound HT-3 was then vapor-deposited to a thickness of 30 nm to form a third hole transport layer, and compound HT-4 was vapor-deposited to a thickness of 5 nm to form a fourth hole transport layer. A second emissive layer was then vapor-deposited thereon as follows: compound H-1 was introduced as a host into one cell of a vacuum vapor deposition system, 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 to form a 20 nm-thick second emissive layer on the fourth hole-transporting layer. Compound ET-1 was deposited to a thickness of 5 nm on the second emissive layer as a second hole-blocking layer material, and compounds ET-2 and EI-1 were deposited as second electron-transporting layer materials in two cells of a vacuum evaporation system, respectively, and the two materials were deposited in a 2:1 weight ratio to a thickness of 25 nm. Yb was then deposited as a 1 nm-thick electron-injecting layer on the second electron-transporting layer, and an Al cathode was then deposited on top of the electron-injecting layer to a thickness of 80 nm using a separate vacuum evaporation system to fabricate an OLED. For each material, 10 -6 Each compound was purified by vacuum sublimation at torr.

[0064] Comparative Examples 1 and 2: Fabrication of OLEDs containing comparative compounds in the N-type charge generating layer An OLED was fabricated in the same manner as in Device Example 1, except that each compound in the N-type charge generating layer listed in Table 1 below was used.

[0065] The OLEDs produced in the above Device Examples 1 to 4 and Comparative Examples 1 and 2 were examined for their driving voltage, current efficiency, and lifespan in a 2x accelerated degradation test. The time required for the brightness to decrease from 100% to 95% at a brightness of 1,000 nits (lifespan: T 95 The change in driving voltage (ΔV) over time after 10 hours was measured. The results are shown in Table 1 below.

[0066] [Table 5]

[0067] From Table 1 above, it can be seen that OLEDs containing compounds according to the present disclosure in their N-type charge generating layers exhibit high lifetime characteristics and / or low fluctuation in drive voltage over time, while still being as effective as or better than OLEDs containing conventional compounds in terms of drive voltage and / or current efficiency. As the change in drive voltage becomes larger, the increase in drive voltage over time also becomes larger, which can result in increased power consumption, overheating of components, and shortened component lifetimes.

[0068] The compounds used in the device examples and comparative examples are shown in Table 2 below.

[0069] [Table 6]

Claims

1. An organic electroluminescent compound represented by the following formula 1: 【Chemistry 1】 (In formula 1, R １ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C １ ~C ３０ ) alkyl, or substituted or unsubstituted (3 to 30 membered) heteroaryl; R ２ ~R ８ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) a substituted or unsubstituted fused ring group with an aromatic ring, or HAr defined by the following formula 1-a, or may be linked to adjacent substituents to form a ring, R ２ ~R ８ is represented by HAr as defined in formula 1-a, 【Chemistry 2】 In the formula, X １ ~X ４ are each independently N or CR ９ represents; L is a single bond, a substituted or unsubstituted (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; R ９ ~R １１ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ２ ~C ３０ ) alkenyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) represents a substituted or unsubstituted fused ring group with an aromatic ring, or may be bonded to L or may be linked to adjacent substituents to form a ring; a represents an integer of 1 to 4, b represents an integer of 1 or 2, and when a and b are integers of 2 or greater, each a and each b may be the same as or different from each other; However, R ８ is HAr in Formula 1, and X in Formula 1-a １ ~X ４ If at least one of １ is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl).

2. The substituted phenyl, the substituted biphenyl, the substituted terphenyl, the substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the substituted fused ring group of the aliphatic ring and the aromatic ring each independently represent deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C １ ~C ３０ ) alkyl, halo (C １ ~C ３０ ) alkyl, (C ２ ~C ３０ ) alkenyl, (C ２ ~C ３０ ) alkynyl, (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, unsubstituted or (C ６ ~C ３０ ) aryl-substituted (5- to 30-membered) heteroaryl, unsubstituted or (5- to 30-membered) heteroaryl-substituted (C ６ ~C ３０ ) aryl, tri(C １ ~C ３０ ) alkylsilyl, tri(C ６ ~C ３０ ) arylsilyl, di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) a condensed 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(3-30 membered)heteroarylamino, (C ６ ~C ３０ ) aryl(3-30 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 ) aryl (C １ ~C ３０ ) alkyl, (C １ ~C ３０ ) alkyl(C ６ ~C ３０ 2. The organic electroluminescent compound of claim 1, wherein the organic electroluminescent compound is substituted with at least one selected from the group consisting of aryl, ...

3. The organic electroluminescent compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-7: 【Transformation 3】 (In formulas 1-1 to 1-7, R １ and HAr is as defined in claim 1; R ２ and R ８ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl).

4. The organic electroluminescent compound according to claim 1, wherein formula 1-a is represented by any one of the following formulas 1-a-1 to 1-a-10: 【Chemistry 4】 (In formulas 1-a-1 to 1-a-10, R １０ , R １１ , L, X １ ~X ４ , a, and b are as defined in claim 1).

5. 2. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the following compounds: 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 (In the above compound, D ｎ indicates that n hydrogens have been replaced with deuterium, where n is an integer from 1 to the maximum number of hydrogens in the compound).

6. An organic electroluminescent material comprising the organic electroluminescent compound of claim 1.

7. An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.

8. An N-type charge generating material comprising the organic electroluminescent compound of claim 1.

9. 8. The organic electroluminescent device of claim 7, comprising a first electrode, a second electrode, a plurality of light-emitting units disposed between the first electrode and the second electrode, and at least one charge-generating layer disposed between adjacent light-emitting units of the plurality of light-emitting units, wherein the charge-generating layer comprises the compound of claim 1.

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