Organic electroluminescent compound and organic electroluminescent device comprising same

Abstract

The present disclosure relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material, an N-type charge generating material, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound, the organic electroluminescent material, or the N-type charge generating material of the present disclosure, an organic electroluminescent device having improved luminous efficiency and / or lifespan characteristics can be provided.

Description

Technical Field

[0001] This disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Technology

[0002] The first green-emitting TPD / Alq3 bilayer small-molecule organic light-emitting diode (OLED), consisting of an emissive layer and a charge transport layer, was developed in 1987 by Tang et al. of Eastman Kodak. Since then, research on organic light-emitting devices has progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs primarily utilize phosphorescent materials with excellent luminous efficiency in panel manufacturing. High OLED efficiency remains a requirement in many applications such as TVs and lighting equipment. For long-term use and high display resolution, OLEDs with long lifetime characteristics are needed.

[0003] Korean Patent Application Publication No. 2027-0105040 discloses phenanthroline derivatives, but does not specifically disclose the particular compound claimed in this publication. Furthermore, there is a continued need to develop luminescent materials that exhibit improved performance (such as enhanced driving voltage, luminous efficiency, power efficiency, and / or lifetime characteristics) compared to previously disclosed compounds. Summary of the Invention

[0004] Technical issues

[0005] The purpose of this disclosure is to provide an organic electroluminescent compound having a novel structure suitable for use in organic electroluminescent devices. Another purpose of this disclosure is to provide an organic electroluminescent device exhibiting high luminous efficiency and / or long lifetime characteristics. A further purpose of this disclosure is to provide an organic electroluminescent material or N-type charge-generating material capable of producing organic electroluminescent devices with high luminous efficiency and / or improved lifetime characteristics.

[0006] Solution to the problem

[0007] As a result of in-depth research into solving the technical problems, the inventors of this invention have discovered that the above objectives can be achieved by an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material, an N-type charge-generating material, and an organic electroluminescent device comprising the same.

[0008]

[0009] In Equation 1,

[0010] R1 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C1) group. 30)alkyl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; and

[0011] R2to R8each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C3-C 30 )cycloalkenyl, substituted or unsubstituted (3- to 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, a substituted or unsubstituted fused ring group of one or more (C3-C 30 )aliphatic rings and one or more (C6-C 30 )aromatic rings, or HAr defined by the following formula 1-a; or can be linked with one or more adjacent substituents to form one or more rings;

[0012] provided that at least one of R2to R8is represented by HAr defined by formula 1-a,

[0013]

[0014] wherein X1to X4each independently represent N or CR9;

[0015] L represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;

[0016] R9to R 11 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C 30) cycloalkyl, substituted or unsubstituted (C3-C 30 ) cycloalkenyl, substituted or unsubstituted (3- to 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 ) alkyl di(C6-C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) arylsilyl, a substituted or unsubstituted fused ring group of one or more (C3-C 30 ) aliphatic rings and one or more (C6-C 30 ) aromatic rings, or a bond to L; or can be linked to one or more adjacent substituents to form one or more rings; and

[0017] a represents an integer of 1 to 4, b represents an integer of 1 or 2, and if a and b are an integer of 2 or more, each of a and each of b can be the same as or different from each other,

[0018] provided that if R8 in Formula 1 is HAr, and at least one of X1 to X4 of Formula 1-a is N, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

[0019] Advantages of the Invention

[0020] The organic electroluminescent compound according to the present disclosure exhibits a performance suitable for use in an organic electroluminescent device. Furthermore, 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 exhibiting higher luminous efficiency and / or improved lifespan characteristics compared to a conventional organic electroluminescent device, and a display device or a lighting device using the same. DETAILED DESCRIPTION

[0021] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure, and is not meant in any way to restrict the scope of the present disclosure.

[0022] 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 layer constituting an organic electroluminescent device as needed.

[0023] The "organic electroluminescent material" in the present disclosure is a material that can be used in an organic electroluminescent device, and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. 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, a light emission auxiliary 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.

[0024] In the present specification, the term "(C1-C 30 )alkyl" means a linear or branched alkyl group having 1 to 30 carbon atoms constituting a chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group can include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, sec-butyl, etc. The term "(C3-C 30 )cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl group can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3- to 7-membered)heterocycloalkyl" in the present disclosure means a saturated or partially unsaturated monocyclic or polycyclic cyclic hydrocarbon substituent having 3 to 7, preferably 5 to 7 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of O, S, and N. The above heterocycloalkyl group can include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc.

[0025] The "(C6-C 30 )aryl" or "(C6-C 30 )arylene" in the present disclosure means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and can be partially saturated. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15. The above aryl group can include a spiro structure. The above aryl group can include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthryl, benzanthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, , benzophenanthryl, phenylphenanthryl, anthryl, benzanthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, Aryl groups include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylexyl, o-cumenel, m-cumenel, p-cumenel, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4-[a]methyl-2-phenyl-2-phenylenel, etc. Specifically, aryl groups may include o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylexyl, o-cumenel, m-cumenel, p-cumenel, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4-[a]methyl-2-phenyl-2-phenylenel, etc. ′ -Methylbiphenyl, 4″-tert-butyl-p-triphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-triphenyl, m-triphenyl-4-yl, m-triphenyl-3-yl, m-triphenyl-2-yl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-tetraphenyl, 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-anthrayl, 2-anthrayl, 9-anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] benzo[a]fluoren-1-yl, benzo[a]fluoren-2-yl, benzo[a]fluoren-3-yl, benzo[a]fluoren-4-yl, benzo[a]fluoren-5-yl, benzo[a]fluoren-6-yl, benzo[a]fluoren-7-yl, benzo[a]fluoren-8-yl, benzo[a]fluoren-9-yl, benzo[a]fluoren-10-yl, benzo[b]fluoren-1-yl, benzo[b]fluoren-2-yl, benzo[b]fluoren-3-yl, benzo[b]fluoren-4-yl, benzo[b]fluoren-5-yl, benzo[b]fluoren-6-yl, benzo[b]fluoren-7-yl, benzo[b]fluoren-8-yl, benzo[b]fluoren-9-yl, benzo[b]fluoren-10-yl, benzo[c]fluoren-1-yl, benzo[c]fluoren-2-yl, benzo[c]fluoren-3-yl, benzo[c]fluoren-4-yl, benzo[c]fluoren-5-yl, benzo[c]fluoren-6-yl, benzo[c]fluoren-7-yl, benzo[c]fluoren-8-yl, benzo[c]fluoren-9-yl, benzo[c]fluoren-10-yl, 11,11-diphenyl-benzo[a]fluoren-1-yl, 11,11-diphenyl-benzo[a]fluoren-2-yl, 11,11-diphenyl-benzo[a]fluoren-3-yl, 11,11-diphenyl-benzo[a]fluoren-4-yl, 11,11-diphenyl-benzo[a]fluoren-5-yl, 11,11-diphenyl-benzo[a]fluoren-6-yl, 11,11-diphenyl-benzo[a]fluoren-7-yl, 11,11-diphenyl-benzo[a]fluoren-8-yl, 11,11-diphenyl-benzo[a]fluoren-9-yl, 11,11-diphenyl-benzo[a]fluoren-10-yl, 11,11-diphenyl-benzo[b]fluoren-1-yl, 11,11-diphenyl-benzo[b]fluoren-2-yl, 11,11-diphenyl-benzo[b]fluoren-3-yl, 11,11-diphenyl-benzo[b]fluoren-4-yl, 11,11-diphenyl-benzo[b]fluoren-5-yl, 11,11-diphenyl-benzo[b]fluoren-6-yl, 11,11-diphenyl-benzo[b]fluoren-7-yl, 11,11-diphenyl-benzo[b]fluoren-8-yl, 11,11-diphenyl-benzo[b]fluoren-9-yl, 11,11-diphenyl-benzo[b]fluoren-10-yl, 11,11-diphenyl-benzo[c]fluoren-1-yl, 11,11-diphenyl-benzo[c]fluoren-2-yl, 11,11-diphenyl-benzo[c]fluoren-3-yl, 11,11-diphenyl-benzo[c]fluoren-4-yl, 11,11-diphenyl-benzo[c]fluoren-5-yl, 11,11-diphenyl-benzo[c]fluoren-6-yl, 11,11-diphenyl-benzo[c]fluoren-7-yl, 11,11-diphenyl-benzo[c]fluoren-8-yl, 11,11-diphenyl-benzo[c]fluoren-9-yl, 11,11-diphenyl-benzo[c]fluoren-10-yl,11, 11-diphenyl-7-benzo [b] fluorenyl, 11, 11-diphenyl-8-benzo [b] fluorenyl, 11, 11-diphenyl-9-benzo [b] fluorenyl, 11, 11-diphenyl-10-benzo [b] fluorenyl, 11, 11-diphenyl- 1-benzo [c] fluorenyl, 11, 11-diphenyl-2-benzo [c] fluorenyl, 11, 11-diphenyl-3-benzo [c] fluorenyl, 11, 11-diphenyl-4-benzo [c] fluorenyl, 11, 11-diphenyl-5-benzo [c] fluorenyl, 11, 11-diphenyl-6-benzo [c] fluorenyl, 11, 11-diphenyl-7-benzo [c] fluorenyl, 11, 11-diphenyl-8-benzo [c] fluorenyl, 11, 11-diphenyl-9-benzo [c] fluorenyl, 11, 11-diphenyl-10-benzo [c] fluorenyl, 9, 9, 10, 10-tetramethyl-9, 10-dihydro-l-phenanthryl, 9, 9, 10, 10-tetramethyl-9, 10-dihydro-2-phenanthryl, 9, 9, 10, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 9, 10, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like.

[0026] “(3- to 30-membered)heteroaryl” or “(3- to 30-membered)heteroarylene” in the present disclosure means an aryl or an 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, and P. Herein, the number of ring skeleton atoms is preferably 3 to 30, and more preferably 5 to 20. The number of heteroatoms is preferably 1 to 4. The aforementioned heteroaryl or heteroarylene group can be a monocyclic ring, or a fused ring condensed with at least one benzene ring, and can be partially saturated. Furthermore, the aforementioned heteroaryl or heteroarylene group can be a heteroaryl or heteroarylene group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and can include a spiro structure. The aforementioned heteroaryl group can include monocyclic-type heteroaryl groups such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring-type heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, benzo-furoquinolyl, benzo-furoquinazolyl, benzo-furo-naphthridinyl, benzo-furo-pyrimidinyl, naphtho-furo-pyrimidinyl, benzo-thienoquinolyl, benzo-thienoquinazolyl, benzo-thieno-naphthridinyl, benzo-thieno-pyrimidinyl, naphtho-thieno-pyrimidinyl, pyrimido-indolyl, benzo-pyrimido-indolyl, benzo-furo-pyrazinyl, naphtho-furo-pyrazinyl, benzo-thieno-pyrazinyl, naphtho-thieno-pyrazinyl, pyrazino-indolyl, benzo-pyrazino-indolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, diphenzo-oxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl, germafluorenyl, benzotriazolyl, phenoxazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazolyl, indolocarbazolyl, and the like. More specifically, the heteroaryl group can include 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-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 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-thiophenyl, 3-thiophenyl, 2-methylpyrrolyl-1-yl, 2-methylpyrrolyl-3-yl, 2-methylpyrrolyl-4-yl, 2-methylpyrrolyl-5-yl, 3-methylpyrrolyl-1-yl, 3-methylpyrrolyl-2-yl, 3-methylpyrrolyl-4-yl, 3-methylpyrrolyl-5-yl, 2-t-butylpyrrolyl-4-yl, 3-(2-phenylpropyl)pyrrolyl-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuryl, 2-dibenzofuryl, 3-dibenzofuryl, 4-dibenzofuryl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[l,2-b]-benzofuranyl, 3-naphtho-[l,2-b]- benzofuranyl, 4-naphtho-[l,2-b]-benzofuranyl, 5-naphtho-[l,2-b]-benzofuranyl, 6- naphtho-[l,2-b]-benzofuranyl, 7-naphtho-[l,2-b]-benzofuranyl, 8-naphtho-[l,2-b]- benzofuranyl, 9-naphtho-[l,2-b]-benzofuranyl, 10-naphtho-[l,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, l-b]-benzofuranyl, 2-naphtho-[2, l-b]-benzofuranyl, 3-naphtho-[2, l-b]- benzofuranyl, 4-naphtho-[2, l-b]-benzofuranyl, 5-naphtho-[2, l-b]-benzofuranyl, 6- naphtho-[2, l-b]-benzofuranyl, 7-naphtho-[2, l-b]-benzofuranyl, 8-naphtho-[2, l-b]- benzofuranyl, 9-naphtho-[2, l-b]-benzofuranyl, 10-naphtho-[2, l-b]-benzofuranyl, 1- naphtho-[l,2-b]-benzothiophenyl, 2-naphtho-[l,2-b]-benzothiophenyl, 3-naphtho-[l,2- b]-benzothiophenyl, 4-naphtho-[l,2-b]-benzothiophenyl, 5-naphtho-[l,2-b]- benzothiophenyl, 6-naphtho-[l,2-b]-benzothiophenyl, 7-naphtho-[l,2-b]- benzothiophenyl, 8-naphtho-[l,2-b]-benzothiophenyl, 9-naphtho-[l,2-b]- benzothiophenyl, 10-naphtho-[l,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, l-b]-benzothiophenyl, 2-naphtho-[2, l-b]- benzothiophenyl, 3-naphtho-[2, l-b]-benzothiophenyl, 4-naphtho-[2, l-b]-1-b]-benzothiophenyl, 9-naphtho-[2, 1-b]-benzothiophenyl, 10-naphtho-[2, 1-b]- benzothiophenyl, 2-benzofuran[3,2-d]pyrimidinyl, 6-benzofuran[3,2-d]pyrimidinyl, 7- benzofuran[3,2-d]pyrimidinyl, 8-benzofuran[3,2-d]pyrimidinyl, 9-benzofuran[3,2-d]pyrimidinyl, 2-benzothia[3,2-d]pyrimidinyl, 6-benzothia[3,2-d]pyrimidinyl, 7-benzothia[3,2-d]pyrimidinyl, 8-benzothia[3,2-d]pyrimidinyl, 9-benzothia[3,2-d]pyrimidinyl, 2-benzofuran[3,2-d]pyrazinyl, 6-benzofuran[3,2-d]pyrazinyl, 7-benzofuran[3,2-d]pyrazinyl, 8-benzofuran[3,2-d]pyrazinyl, 9-benzofuran[3,2-d]pyrazinyl, 2-benzothia[3,2-d]pyrazinyl, 6-benzothia[3,2-d]pyrazinyl, 7-benzothia[3,2-d]pyrazinyl, 8-benzothia[3,2-d]pyrazinyl, 9-benzothia[3,2-d]pyrazinyl, 1-silolyl, 2-silolyl, 3-silolyl, 4-silolyl, 1-germolyl, 2-germolyl, 3-germolyl, 4-germolyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Further, the "(hetero)aryl group" can be classified into a (hetero)aryl group having an electron-transport property and a (hetero)aryl group having a hole-transport property. The (hetero)aryl group having an electron-transport property is a substituent relatively rich in electrons in a mother nucleus, such as a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinolyl group, and the like. The (hetero)aryl group having a hole-transport property is a substituent relatively deficient in electrons in a mother nucleus, such as a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and the like.

[0027] In the present specification, the "fused ring group of one or more (C3-C 30 )aliphatic rings and one or more (C6-C 30 )aromatic rings" means a functional group of rings in which at least one aliphatic ring having 3 to 30 ring backbone carbon atoms, preferably 3 to 25 ring backbone carbon atoms, and more preferably 3 to 18 ring backbone carbon atoms, is fused with at least one aromatic ring having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, and more preferably 6 to 18 ring backbone carbon atoms. Specific examples of the fused ring group include a fused ring group of one or more benzene and one or more cyclohexane, or a fused ring group of one or more naphthalene and one or more cyclopentane, and the like. In the present specification, the "one or more (C3-C 30) aliphatic ring and one or more (C6-C3o)aromatic ring. The carbon atoms of the fused ring group of the (C6-C3o)aromatic ring can be replaced by one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, preferably one or more heteroatoms selected from the group consisting of N, O, and S. In this context, "halogen" includes F, Cl, Br, and I. 30 ) aliphatic ring and one or more (C6-C3o)aromatic ring. The carbon atoms of the fused ring group of the (C6-C3o)aromatic ring can be replaced by one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, preferably one or more heteroatoms selected from the group consisting of N, O, and S. In this context, "halogen" includes F, Cl, Br, and I.

[0028] Further, "ortho-" ("o-"), "meta-" ("m-"), and "para-" ("p-") are prefixes that each indicate the relative position of substituents. The prefix "ortho-" indicates that two substituents are adjacent to each other, and, for example, when two substituents in a benzene derivative occupy positions 1 and 2, this is referred to as the "ortho-" configuration. The prefix "meta-" indicates that two substituents are at positions 1 and 3, and, for example, when two substituents in a benzene derivative occupy positions 1 and 3, this is referred to as the "meta-" configuration. The prefix "para-" indicates that two substituents are at positions 1 and 4, and, for example, when two substituents in a benzene derivative occupy positions 1 and 4, this is referred to as the "para-" configuration.

[0029] In this context, "a ring formed by connection with one or more adjacent substituents" means that at least two adjacent substituents are connected or fused to each other 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 can be a substituted or unsubstituted monocyclic or polycyclic (5- to 25-membered) alicyclic ring or aromatic ring, or a combination thereof. Further, the ring can contain 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 N, O, and S. According to one embodiment of the present disclosure, the number of ring skeleton carbon atoms is 5 to 20, and according to another embodiment of the present disclosure, the number of ring skeleton carbon atoms is 5 to 15. For example, the fused ring can 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, and the like.

[0030] In this document, "substituted or unsubstituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., a substituent), and this also includes being substituted with a group in which two or more substituents are linked. Unless otherwise specified, a substituent can replace a hydrogen without limitation at a position where a hydrogen can be substituted, and when two or more hydrogen atoms in a certain functional group are each replaced with a substituent, each substituent can be the same as 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 of each atom forming the functional group that can be substituted. In this document, a substituted phenyl group, a substituted biphenyl group, a substituted terphenyl group, a substituted alkyl group, a substituted alkenyl group, a substituted aryl group, a substituted arylene group, a substituted heteroaryl group, a substituted heteroarylene group, a substituted cycloalkyl group, a substituted cycloalkenyl group, a substituted heterocycloalkyl group, a substituted alkoxy group, a substituted trialkylsilyl group, a substituted dialkylarylsilyl group, a substituted alkyldiarylsilyl group, a substituted triarylsilyl group, and a substituted fused ring group of one or more aliphatic rings and one or more aromatic rings, each independently can be substituted with at least one selected from the group consisting of deuterium, a halogen, a cyano group, a carboxyl group, a nitro group, a hydroxyl group, a (C1-C 30 )alkyl group, a halo(C1-C 30 )alkyl group, a (C2-C 30 )alkenyl group, a (C2-C 30 )alkynyl group, a (C1-C 30 )alkoxy group, a (C1-C 30 )alkylthio group, a (C3-C 30 )cycloalkyl group, a (C3-C 30 )cycloalkenyl group, a (3- to 7-membered)heterocycloalkyl group, a (C6-C 30 )aryloxy group, a (C6-C 30 )arylthio group, a (5- to 30-membered)heteroaryl group which is unsubstituted or substituted with a (C6-C 30 )aryl group, a (C6-C 30 )aryl group which is unsubstituted or substituted with a (5- to 30-membered)heteroaryl group, a tri(C1-C 30 )alkylsilyl group, a tri(C6-C 30 )arylsilyl group, a di(C1-C 30 )alkyl(C6-C 30 )arylsilyl group, a (C1-C 30 )alkyldi(C6-C 30 )arylsilyl group, a fused ring group of one or more (C3-C 30 )aliphatic rings and one or more (C6-C 30 )aromatic rings, an amino group, a mono- or di(C1-C 30) alkylamino, substituted or unsubstituted mono- or di(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) alkyl(C6-C 30 ) arylamino, substituted or unsubstituted mono- or di(3- to 30-membered)heteroaryl amino, substituted or unsubstituted (C1-C 30 ) alkyl(3- to 30-membered)heteroaryl amino, substituted or unsubstituted (C6-C 30 ) aryl(3- to 30-membered)heteroaryl amino, (C1-C 30 ) alkylcarbonyl, (C1-C 30 ) alkoxycarbonyl, (C6-C 30 ) arylcarbonyl, (C6-C 30 ) aryloxyphosphinyl, 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 can be deuterium.

[0031] In the present disclosure, if a substituent is not indicated in a chemical formula or a structure of a compound, it can 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 can be the isotope deuterium, and in this case, the content of deuterium can be 0% to 100%. In the present disclosure, in the case where a substituent is not indicated in a chemical formula or a structure of a compound, if the substituent is not explicitly excluded, such as 0% deuterium, 100% hydrogen, and all substituents are hydrogen, hydrogen and deuterium can be used in mixture in the compound. Deuterium is one of the isotopes of hydrogen and is an element having a deuterium nucleus as its nucleus, which consists of one proton and one neutron. It can be denoted as hydrogen-2, and the element symbol can also be written as D or 2 H. Isotopes are atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0032] In the present disclosure, “combinations thereof’ refers to combinations of one or more elements from the respective list to form a known or chemically stable arrangement that one of skill in the art can envision from the respective 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 haloalkyl substituent, and halogen, alkyl, and aryl can combine to form a haloarylalkyl group. For example, preferred combinations of substituents contain 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 can contain up to 20 atoms that are not hydrogen or deuterium.

[0033] In the formulas of the present disclosure, when there are multiple substituents represented by the same symbol, each of the substituents represented by the same symbol can be the same as or different from each other.

[0034] The compounds represented by Formula 1 are described in more detail as follows.

[0035] In Formula 1, R1represents 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. According to one embodiment of the present application, R1represents 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- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, R1represents 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- to 25-membered)heteroaryl. For example, R1may be hydrogen, deuterium, fluorine, methyl, phenyl, o-biphenyl, m-biphenyl, p-biphenyl, pyridyl, etc., which can be substituted with one or more deuterium.

[0036] In Formula 1, R2to R8each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted (C2-C 30 )alkenyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C3-C 30 )cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C1-C30 )alkoxy, substituted or unsubstituted tri(Ci-C 30 )alkylsilyl, substituted or unsubstituted di(Ci-C 30 )alkyl(C6-C 30 )arylsilyl, substituted or unsubstituted (Ci-C 30 )alkyldi(C6-C 30 )arylsilyl, substituted or unsubstituted tri(C6-C 30 )arylsilyl, one or more (C3-C 30 )aliphatic rings and one or more (C6-C 30 )aromatic rings, or HAr defined by Formula 1-a below; or can be linked to one or more adjacent substituents to form one or more rings; provided that at least one of R2to R8is represented by HAr defined by Formula 1-a. According to one embodiment of the present disclosure, R2to R8each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (Ci-C 30 )alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, or HAr defined by Formula 1-a below. According to another embodiment of the present disclosure, R2to R8each independently represent hydrogen, deuterium, phenyl, pyridyl, or the like, or HAr defined by Formula 1-a below, which can be substituted with one or more deuterium.

[0037]

[0038] In Formula 1-a, X1to X4each independently represent N or CR9. According to one embodiment of the present disclosure, at least one of X1to X4is N. According to another embodiment of the present disclosure, at least one or two of X1to X4is N.

[0039] In Formula 1-a, L represents a single bond, a substituted or unsubstituted (C6-C 30 )arylene, or a 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-C 25 )arylene, or a substituted or unsubstituted (5- to 20-membered)heteroarylene. According to another embodiment of the present disclosure, L represents a single bond, or a (C6-C 18 )arylene which is unsubstituted or substituted with deuterium. For example, L can be a single bond, phenylene, naphthylene, or the like, which can be substituted with one or more deuterium.

[0040] In Formula 1-a, R9to R 11 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (Ci-C30 )alkyl, substituted or unsubstituted (C2-C 30 Alkenyl, substituted or unsubstituted (C6-C) 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C3-C 30 Cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocyclic alkyl, substituted or unsubstituted (C1-C2) 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C2) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, one or more (C3-C 30 Aliphatic rings and one or more (C6-C) 30 The aromatic ring may be substituted or unsubstituted fused ring groups, or bonded to L; or may be linked to one or more adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R9 to R... 11 One of them is bonded to L, and the remaining R9 to R 11 Each is independently hydrogen, deuterium, substituted or unsubstituted (C1-C) 20 )alkyl, substituted or unsubstituted (C6-C 25 ) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl. According to another embodiment of this disclosure, R9 to R 11 One of them is bonded to L, and the remaining R9 to R 11 Each is independently hydrogen, deuterium, unsubstituted or deuterated (C1-C). 10 )alkyl, or unsubstituted or deuterated (C6-C) 18 )Aryl. For example, R9 can be hydrogen, deuterium, methyl, phenyl, etc., and it can be substituted with one or more deuterium groups; R 10 and R 11 They can each be hydrogen or deuterium independently; and R9 to R 11 One of them can be bonded to L.

[0041] In Equation 1-a, a represents an integer from 1 to 4, b represents an integer of 1 or 2, and if a and b are integers of 2 or greater, then each a and each b can be the same or different from each other.

[0042] provided that if R8 in formula 1 is HAr, and at least one of X1 to X4 of formula 1-a is N, R1 is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

[0043] Formula 1 can be represented by at least one of the following formulas 1-1 to 1-7.

[0044]

[0045] In formulas 1-1 to 1-7, R1 and HAr are as defined in formula 1.

[0046] In formulas 1-1 to 1-7, R2 to R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )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, or the like, which can be substituted with deuterium(s).

[0047] Formula 1-a can be represented by at least one of the following formulas 1-a-1 to 1-a-10.

[0048]

[0049]

[0050] 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.

[0051] The organic electroluminescent compound represented by formula 1 can be at least one selected from the group consisting of the following compounds, but is not limited thereto.

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] In the above compounds, Dn means that n number of hydrogens are replaced with deuterium, and n represents an integer of 1 to the maximum number of hydrogens in the compound. Specifically, n is an integer of at least 1 and at most the number of hydrogens in the compound.

[0059] According to one embodiment of the present disclosure, in the compound represented by Formula 1, when deuterium is included, the deuterium substitution rate is preferably about 100% or less, more preferably 95% or less, still more preferably 90% or less, and even more preferably 85% or less, of the total number of hydrogens. The compound of Formula 1 substituted with the above deuterium substitution rate can increase the stability of the compound by increasing the bond dissociation energy according to deuteration, and an organic electroluminescent device including the compound can exhibit improved light-emitting characteristics.

[0060] The compound represented by Formula 1 can be produced by a synthetic method known to one skilled in the art. For example, the compound of the present disclosure can be synthesized by referring to the following Reaction Scheme 1, but is not limited thereto.

[0061] [Reaction Scheme 1]

[0062]

[0063] In Reaction Scheme 1, R2 to R8, R 10 , R 11 , X1 to X4, L, a, and b are each as defined in Formula 1.

[0064] The present disclosure provides an organic electroluminescent material, an N-type charge generation material, or an organic electroluminescent device including the above compound.

[0065] According to one embodiment of the present disclosure, an organic electroluminescent device includes a first electrode; a second electrode; a plurality of light-emitting units between the first electrode and the second electrode; and at least one charge generation layer between adjacent light-emitting units of the plurality of light-emitting units, wherein the charge generation layer can include a compound represented by Formula 1.

[0066] An organic electroluminescent device according to one embodiment of the present disclosure can be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to one embodiment, a single light emitting cell (light emitting part) can be formed in a structure in which two or more cells are connected by a charge generation layer. The organic electroluminescent device can include a plurality of two or more light emitting cells, for example, a plurality of three or more light emitting cells, the light emitting cell having a first electrode and a second electrode opposite each other on a substrate and a light emitting layer stacked between the first electrode and the second electrode and emitting light in a specific wavelength range. The organic electroluminescent device can include a plurality of light emitting cells, and each of the light emitting cells can include a hole transport zone, a light emitting layer, and an electron transport zone, the hole transport zone can include a hole injection layer and a hole transport layer, and the electron transport zone can include an electron transport layer and an electron injection layer. According to one embodiment of the present disclosure, three or more light emitting layers can be included in a light emitting cell. The plurality of light emitting cells can emit the same color or different colors. In addition, one light emitting cell can include one or more light emitting layers, and the plurality of light emitting layers can be light emitting layers of the same color or different colors. It can include one or more charge generation layers located between each light emitting cell.

[0067] The charge generation layer refers to a layer that generates holes and electrons when a voltage is applied. When there are three or more light emitting cells, the charge generation layer can be located between each light emitting cell. The plurality of charge generation layers can be the same as or different from each other. By providing a charge generation layer between light emitting cells, the current efficiency in each light emitting cell increases, and charges can be uniformly distributed. Specifically, the charge generation layer is disposed between two adjacent stacks, and can be used to drive a tandem organic electroluminescent device using only a pair of anode and cathode, without the need for a separate internal electrode located 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 contain a compound represented by Formula 1 of the present disclosure. The P-type charge generation layer can be made of a metal or an organic material doped with a P-type dopant. For example, the metal can be made of one or two or more alloys selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. In addition, commonly used materials can be used as the P-type dopant and the host material used in the P-type doped organic material.

[0068] An organic electroluminescent device according to another embodiment of the disclosure includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode, wherein the organic layer includes a hole transport layer, an emission layer, a hole auxiliary layer, an electron blocking layer, a charge generation layer, and an emission auxiliary layer. According to one embodiment of the disclosure, at least one layer among the hole transport layer, the emission layer, the hole auxiliary layer, the electron blocking layer, the charge generation layer, and the emission auxiliary layer can include a compound represented by Formula 1. For example, the charge generation layer can include a compound represented by Formula 1. According to one embodiment of the disclosure, the organic electroluminescent material of the disclosure includes at least one compound among Compounds C-1 to C-120, and the organic electroluminescent material can be included in the same organic layer (e.g., the charge generation layer).

[0069] In addition to the hole transport layer, the emission layer, the hole auxiliary layer, the electron blocking layer, the charge generation layer, and the emission auxiliary layer, the organic layer can further include at least one layer selected from a hole injection layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron buffer layer. In addition to the compound of the disclosure, the organic layer can additionally include an amine-based compound and / or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the emission layer, the emission auxiliary layer, or the electron blocking layer can include an amine-based compound (e.g., an arylamine-based compound, a styryl arylamine-based compound, etc.) as a hole injection material, a hole transport material, a hole auxiliary material, an emission material, an emission auxiliary material, and an electron blocking material. Further, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer can include an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material. Further, the organic material layer can further include at least one metal selected from the group consisting of a metal of Group 1 of the periodic table, a metal of Group 2, a transition metal of Period 4, a transition metal of Period 5, a lanthanide series element, and an organic metal of d-transition element, or at least one complex compound including the metal.

[0070] The compound according to one embodiment of the disclosure can be used as an emission material for a white organic light emitting device. According to the arrangement of R (red), G (green), or YG (yellow green) and B (blue) emission units, a white organic light emitting device has 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, etc. Further, according to one embodiment of the disclosure, the organic electroluminescent compound can also be used in an organic electroluminescent device including a quantum dot (QD).

[0071] One of the first and second electrodes can be an anode, and the other can be a cathode. The first and second electrodes can each be formed from a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of materials forming the first and second electrodes, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type.

[0072] The light-emitting layer may comprise one or more substrates and one or more dopants. The dopants included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent dopant or a fluorescent dopant, and are preferably phosphorescent dopants.

[0073] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the emissive layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein two compounds can be used simultaneously in each of the multilayers. Furthermore, the hole injection layer can be further doped with a p-type dopant. An electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the emissive layer, and can confine excitons within the emissive layer by blocking electrons from escaping from the emissive layer to prevent light leakage. The hole transport layer or electron transport layer can also be multilayered, wherein each of the multilayers can use multiple compounds.

[0074] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, where each of the multilayers can use two compounds simultaneously. A hole blocking layer can be placed between the electron transport layer (or electron injection layer) and the light-emitting layer to block holes from reaching the cathode, thereby increasing the probability of electron-hole recombination in the light-emitting layer. The hole blocking layer or electron transport layer can also be multilayered, where each layer can use multiple compounds. Furthermore, the electron injection layer can be doped with an n-type dopant.

[0075] The light-emitting auxiliary layer can be a layer placed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, the light-emitting auxiliary layer can function to facilitate hole injection and / or hole transport or to block the overflow of electrons. When placed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can function to facilitate electron injection and / or electron transport or to block the overflow of holes. In addition, a hole auxiliary layer can be placed between the hole transport layer (or the hole injection layer) and the light-emitting layer, and can exhibit a function of facilitating or blocking the rate of hole transport (or the rate of hole injection), and thus can adjust the charge balance. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer can function as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have a function of improving the efficiency and / or the lifespan of the organic electroluminescent device.

[0076] 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 placed on at least one inner surface of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably placed on the anode surface on the side of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on the cathode surface on the side of the electroluminescent medium layer. The driving stability of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of the chalcogenide include SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc., preferred examples of the metal halide include LiF, MgF2, CaF2, rare earth metal fluoride, etc., and preferred examples of the metal oxide include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0077] Further, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier for electrons to be injected and transported from the mixed region to the light-emitting medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier for holes to be injected and transported from the mixed region to the light-emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, an organic electroluminescent device having two or more light-emitting layers and emitting white light can be manufactured by using a reducing dopant layer as a charge generation layer.

[0078] According to one embodiment, this disclosure can provide a display device comprising a compound represented by Formula 1. Furthermore, the organic electroluminescent device of this disclosure can be used to manufacture display devices such as smartphones, tablets, laptops, PCs, TVs, or vehicle display devices, or lighting devices such as outdoor or indoor lighting.

[0079] The preparation method of the organic electroluminescent compound according to this disclosure, its physical properties, and the driving voltage, current efficiency, and lifetime characteristics of the OLED according to this disclosure will be explained in detail below. However, the following examples only describe the properties of the compound and OLED according to this disclosure, and this disclosure is not limited to the following examples.

[0080] Example 1: Preparation of compound C-5

[0081]

[0082] 2-Phenyl-9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1,10-phenanthroline (20.0 g, 43.6 mmol), 2-chloro-3-phenylbenzo[f]quinoxaline (12.7 g, 43.6 mmol), Pd(Amphos)Cl2 (2.2 g, 3.1 mmol), aliquot 336 (1.8 g, 4.4 mmol), and Na2CO3 (9.2 g, 87 mmol) were dissolved in 220 mL of toluene and 75 mL of H2O, and the mixture was then stirred under reflux at 130 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was separated. Subsequently, the residue was separated by column chromatography to obtain compound C-5 (12.5 g, yield: 49%).

[0083] MW Melting point C-5 586.2 259℃

[0084] Example 2: Preparation of compound C-2

[0085]

[0086] Compound C-2: 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10- phenanthrolin-2-yl(2-chloro-3-phenylbenzo[f]quinoxaline) 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl(2-chloro-3-phenylbenzo[f]quinoxaline) was prepared according to the following procedure. 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin (10.0 g, 26.2 mmol), 2-chloro-3-phenylbenzo[f]quinoxaline (9.1 g, 31.4 mmol), Pd(Amphos)Cl2(1.3 g, 1.8 mmol), aliquot 336 (1.1 g, 2.6 mmol), and Na2CO3(5.5 g, 52.3 mmol) were dissolved in 130 mL of toluene and 45 mL of H2O, and then the mixture was stirred at 130 °C under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was separated. Thereafter, the residue was separated using column chromatography to obtain compound C-2 (7.3 g, yield: 54%).

[0087] MW Melting point C-2 510.6 280℃

[0088] Example 3: Preparation of compound C-9

[0089]

[0090] Compound C-9: 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10- phenanthrolin-2-yl(2-chloro-4-phenylbenzo[h]quinazoline) 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin-2-yl(2-chloro-4-phenylbenzo[h]quinazoline) was prepared according to the following procedure. 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,10-phenanthrolin (10.0 g, 21.8 mmol), 2-chloro-4-phenylbenzo[h]quinazoline (7.6 g, 26 mmol), Pd(Amphos)Cl2(1.1 g, 1.5 mmol), aliquot 336 (0.9 g, 2.2 mmol), and Na2CO3(4.6 g, 44 mmol) were dissolved in 110 mL of toluene and 36 mL of H2O, and then the mixture was stirred at 130 °C under reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was separated. Thereafter, the residue was separated using column chromatography to obtain compound C-9 (7.1 g, yield: 55%).

[0091] MW Melting point C-9 586.7 285℃

[0092] Example 4: Preparation of compound C-10

[0093]

[0094] Dissolve 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) in 200 mL of toluene, 50 mL of EtOH, and 50 mL of H2O, and then stir the mixture at 130°C under reflux for 18 hours. After completion of the reaction, cool the mixture to room temperature, and separate the organic layer. Thereafter, separate the residue using column chromatography to obtain compound C-10 (22.0 g, yield: 86%)

[0095] MW Melting point C-10 510.60 256℃

[0096] Device Examples 1 to 4: Production of OLEDs comprising a compound according to the present disclosure in the N-type charge generation layer

[0097] An OLED according to the present disclosure was produced. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to ultrasonic washing with acetone and isopropanol in this order, and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-3 was introduced into another chamber. The two materials were evaporated at different rates, and compound HI-1 was deposited at a doping amount of 3 wt% based on the total amount of compound HI-1 and compound HT-3 to form a hole injection layer having a thickness of 5 nm. Subsequently, compound HT-3 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 30 nm. Compound HT-4 was then introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying electric current to the chamber, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After the formation of the hole injection layer and the hole transport layers, a first light-emitting layer was deposited thereon as follows: compound H-1 was introduced into one chamber of the vacuum vapor deposition apparatus as a host, and compound D-1 was introduced into another chamber as a dopant. 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 the dopant to form the first light-emitting layer having a thickness of 20 nm on the second hole transport layer. Subsequently, compound ET-1 was deposited on the first light-emitting layer to a thickness of 5 nm as a first hole blocking layer material. Compound ET-2 was then deposited as an electron transport layer material having a thickness of 10 nm to form a first electron transport layer. Thereafter, an N-type charge generation layer having a thickness of 4 nm was formed by depositing 0.5 wt% of Li (lithium) on the compounds of the N-type charge generation layer described in Table 1. Subsequently, compound HI-1 was deposited at a doping amount of 6 wt% based on the total amount of compound HI-1 and compound HT-3 to form a P-type charge generation layer having a thickness of 10 nm. After compound HT-3 was deposited to a thickness of 30 nm to form a third hole transport layer, compound HT-4 was deposited to a thickness of 5 nm to form a fourth hole transport layer. Subsequently, a second light-emitting layer was deposited thereon as follows: compound H-1 was introduced into one chamber of the vacuum vapor deposition apparatus as a host, and compound D-1 was introduced into another chamber as a dopant. 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 the dopant to form the second light-emitting layer having 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 material, compounds ET-2 and EI-1 were introduced into two cells of a vacuum deposition apparatus as a second electron-transporting layer material, respectively, and the two materials were deposited to a thickness of 25 nm in a weight ratio of 2:1. After Yb was deposited on the second electron-transporting layer as an electron-injecting layer having a thickness of 1 nm, another vacuum vapor deposition apparatus was used to deposit an Al cathode having a thickness of 80 nm on the electron-injecting layer to manufacture an OLED. For each material, each compound was used at 10. -6 Toluene was purified by vacuum sublimation and used.

[0098] Comparative Examples 1 and 2: Production of OLEDs comprising comparative compounds in the N-type charge generation layer

[0099] OLEDs were produced in the same manner as in Device Example 1, except that each compound of the N-type charge generation layer described in Table 1 below was used.

[0100] The driving voltage, current efficiency, time taken for the luminance to decrease from 100% to 95% at a luminance of 1,000 nits when checked for lifetime with 2x accelerated aging (Lifetime: T 95 ), and progressive driving voltage change (ΔV) after 10 hours were measured for the OLEDs produced in Device Examples 1 to 4 and Comparative Examples 1 and 2, and the results thereof are shown in Table 1 below.

[0101] [Table 1]

[0102]

[0103] It can be confirmed from Table 1 above that the OLEDs including the compound according to the present disclosure in the N-type charge generation layer have an effect equal to or greater than that of the OLEDs including the conventional compound in terms of driving voltage and / or current efficiency, while exhibiting a high lifetime characteristic and / or a low progressive driving voltage change. As the change in driving voltage becomes greater, the increase in driving voltage over time also becomes greater, which can result in an increase in power consumption, overheating of components, and a reduction in the lifetime of components.

[0104] The compounds used in the device examples and comparative examples are shown in Table 2 below.

[0105] [Table 2]

[0106]

[0107]

Claims

1. An organic electroluminescent compound represented by the following Formula 1: wherein in Formula 1, R1represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted (C1-C30)alkyl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; and 30 )alkyl, or substituted or unsubstituted (3- to 30-membered)heteroaryl; and R2 through R8 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C2-C 30 Alkenyl, substituted or unsubstituted (C6-C) 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C3-C 30 Cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocyclic alkyl, substituted or unsubstituted (C1-C2) 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C1) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, one or more (C3-C 30 Aliphatic rings and one or more (C6-C) 30 A substituted or unsubstituted fused ring group of an aromatic ring, or HAr as defined by formula 1-a below; or may be connected with one or more adjacent substituents to form one or more rings; provided that at least one of R 2 to R 8 is represented by HAr defined in Formula 1-a, wherein X 1 to X 4 each independently represent N or CR 9; L indicates a single bond, substitution, or no substitution (C6-C). 30 ) aryl, or substituted or unsubstituted (3 to 30 yuan) heteroaryl; R9 to R 11 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C) 30 )alkyl, substituted or unsubstituted (C2-C 30 Alkenyl, substituted or unsubstituted (C6-C) 30 )Aryl, substituted or unsubstituted (3 to 30 yuan) Heteroaryl, substituted or unsubstituted (C3-C 30 )cycloalkyl, substituted or unsubstituted (C3-C 30 Cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocyclic alkyl, substituted or unsubstituted (C1-C2) 30 )alkoxy, substituted or unsubstituted tri(C1-C) 30 )alkylsilyl, substituted or unsubstituted di(C1-C1) 30 )alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 )alkyl di(C6-C 30 arylsilyl, substituted or unsubstituted tri(C6-C) 30 ) arylsilyl, one or more (C3-C 30 Aliphatic rings and one or more (C6-C) 30 The aromatic ring may contain substituted or unsubstituted fused ring groups, or be bonded to L; or may be linked to one or more adjacent substituents to form one or more rings; and a represents an integer of 1 to 4, b represents an integer of 1 or 2, and if a and b are an integer of 2 or more, each a and each b can be the same as or different from each other, Provided that if R8in Formula 1 is HAr, and at least one of X1to X4of Formula 1-a is N, then R1is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 )alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted terphenyl.

2. The organic electroluminescence compound according to claim 1, wherein 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 fused ring groups of the substituted one or more aliphatic rings and one or more aromatic rings, are each independently substituted with at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C2) 30 alkyl, halogenated (C1-C) 30 )alkyl, (C2-C 30 )alkenyl, (C2-C 30 ) ynyl group, (C1-C 30 )alkoxy, (C1-C 30 )alkylthio, (C3-C 30 )cycloalkyl, (C3-C 30 Cycloalkenyl, (3- to 7-membered) heterocycloalkyl, (C6-C 30 ) aryloxy group, (C6-C 30 ) arylthio, unsubstituted or (C6-C) 30 )Aryl-substituted (5 to 30 yuan) heteroaryl, unsubstituted or (5 to 30 yuan) heteroaryl-substituted (C6-C 30 )Aromatic, 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, one or more (C3-C 30 Aliphatic rings and one or more (C6-C) 30 Aromatic ring fused ring groups, amino groups, mono- or di(C1-C) groups 30 )alkylamino, mono- or di(C6-C 30 ) arylamino, (C1-C 30 )alkyl (C6-C 30 ) arylamino, mono- or di(3- to 30-membered) heteroarylamino, (C1-C 30 )alkyl (3- to 30-membered) heteroarylamino, (C6-C 30 ) aryl (3- to 30-membered) heteroarylamino, (C1-C 30 )alkylcarbonyl, (Ci-C 30 )alkoxycarbonyl, (C6-C 30 )arylcarbonyl, (C6-C 30 )aryloxyphosphinyl, di(C6-C 30 )arylboronyl, di(Ci-C 30 )alkylboronyl, (Ci-C 30 )alkyl(C6-C 30 )arylboronyl, (C6-C 30 )aryl(Ci-C 30 )alkyl, (Ci-C 30 )alkyl(C6-C 30 )aryl, and combinations thereof.

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: wherein in Formulas 1-1 to 1-7, R 1 and HAr are as defined in claim 1; and R2to R8each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C6)alkyl, substituted or unsubstituted (C6-C10)aryl, or substituted or unsubstituted (3- to 30-membered)heteroaryl. 30 )alkyl, substituted or unsubstituted (C6-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: wherein in Formulas 1-a-1 to 1-a-10, R 10 , R 11 , L, X1to X4, a and b 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: In the above compounds, D n means that the number n of hydrogens is replaced by deuterium and n denotes an integer from 1 to the maximum number of hydrogens in the compound. 6.An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1. 7.An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1. 8.An N-type charge generation material comprising the organic electroluminescent compound according to claim 1.

9. The organic electroluminescence device according to claim 7, wherein the organic electroluminescent device comprises a first electrode; a second electrode; a plurality of light-emitting units between the first electrode and the second electrode; and at least one charge generation layer between adjacent light-emitting units of the plurality of light-emitting units, wherein the charge generation layer comprises the compound according to claim 1.

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