Organic electroluminescent compound, host materials, and organic electroluminescent device comprising same

Abstract

An organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. The present disclosure relates to an organic electroluminescent compound represented by Formula 2'or Formula 2 '', a plurality of host materials comprising at least one first host compound and at least one second host compound, and an organic electroluminescent device comprising the same. An organic electroluminescent device having improved driving voltage, luminous efficiency, power efficiency, and / or lifespan characteristics can be provided by comprising the organic electroluminescent compound or a specific combination of compounds according to the present disclosure as one or more host materials. Ar11 (L11-HAr) e-----(2 ') Ar11 (L11-HAr) e-----(2' '), and (L11-HAr) e----(2' ').

Description

[0001] This invention patent application is a divisional application of the invention patent application with application number 202110833828.5, application date July 22, 2021, and name “Organic electroluminescent compounds, multiple host materials and organic electroluminescent devices containing the same”. Technical Field

[0002] The present disclosure relates to an organic electroluminescent compound, a plurality of host materials, and an organic electroluminescent device comprising the same. Background Art

[0003] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) consisting of a TPD / Alq3 double layer consisting of a light-emitting layer and a charge transport layer. Since then, the development of OLED has been rapidly affected and OLED has been commercialized. At present, organic electroluminescent devices mainly use phosphors with excellent luminous efficiency in realizing panels. Long-term use and high-resolution displays require OLEDs with high luminous efficiency and / or long life.

[0004] In order to improve the luminous efficiency, driving voltage, and / or lifespan, various materials or concepts for the organic layer of the organic electroluminescent device have been proposed, but they are not satisfactory in practical use. Therefore, there is a continuous need to develop an organic electroluminescent device that has improved performance, such as improved driving voltage, luminous efficiency, power efficiency and / or lifespan characteristics, compared to conventional organic electroluminescent devices.

[0005] Meanwhile, Korean Patent Application Publication No. 2012-0104067 discloses a compound in which a nitrogen-containing heteroaryl group is bonded to a benzonaphthothiophene moiety, but does not specifically disclose a specific combination of the host material claimed herein. Summary of the invention

[0006] Technical issues

[0007] The object of the present disclosure is to provide a compound having a novel structure suitable for use as an organic electroluminescent material. Another object of the present disclosure is to provide an organic electroluminescent device having low driving voltage, high luminous efficiency, high power efficiency and / or excellent life characteristics by including a plurality of host materials containing a specific combination of compounds.

[0008] Solution to the problem

[0009] As a result of in-depth research to solve the above technical problems, the inventors of the present invention found that the above purpose can be achieved by an organic electroluminescent compound represented by the following formula 2' or formula 2". In addition, the inventors of the present invention found that the above purpose can be achieved by the following multiple host materials, wherein the multiple host materials contain at least one first host compound and at least one second host compound to achieve the above purpose, wherein the first host compound is represented by the following formula 1, and the second host compound is represented by the following formula 2.

[0010] Ar 11 (L 11 -HAr) e -----(2′)

[0011] In formula 2',

[0012] HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidyl group, or a substituted or unsubstituted benzothienopyrimidinyl group;

[0013] L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0014] Ar 11 Each independently represents any one of the following formulae 3 to 5:

[0015]

[0016] In equations 3 to 5,

[0017] Y2 represents O or S;

[0018] R 20 To R 29 represents hydrogen or deuterium;

[0019] E represents 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other; and

[0020] *Indicates the same as L 11 The site of connection;

[0021] Provided that, when HAr is a substituted triazine group, the substituents of the substituted triazine group are each independently selected from deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dimethylfluorenyl, fluoranthenyl, A substituent group is a carbazolyl group, a carbazolyl group, and a combination thereof, and when there are two substituent groups, the two substituent groups are the same as or different from each other.

[0022] Ar 11 (L 11 -HAr) e -----(2″)

[0023] In formula 2",

[0024] HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group;

[0025] L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0026] Ar 11 Each independently represents any one of the following formulae 3 to 5:

[0027]

[0028] In equations 3 to 5,

[0029] Y2 represents O or S;

[0030] R 21 To R 24 and R 26 To R 29 each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0031] R 20 and R 25 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0032] E represents 1 or 2, and when e is 2, each (L 11 -HAr) may be the same as or different from each other; and

[0033] *Indicates the same as L 11 The site of connection.

[0034]

[0035] In formula 1,

[0036] X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that either one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR5-, -O-, or -S-;

[0037] R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0038] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0039] Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0040] R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) Alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N-(Ar3)(Ar4); or may be connected to an adjacent substituent to form a ring;

[0041] a represents 1, b and c each independently represent 1 or 2, and d represents an integer of 1 to 4, wherein if b to d are integers of 2 or more, each R2 to each R4 may be the same as or different from each other;

[0042] Ar 11 (L 11 -HAr) e -----(2)

[0043] In formula 2,

[0044] HAr each independently represents a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group;

[0045] L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0046] Ar 11 Each independently represents any one of the following formulae 3 to 5:

[0047]

[0048] In equations 3 to 5,

[0049] Y2 represents O or S;

[0050] R 20 To R 29 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N-(Ar3)(Ar4);

[0051] e represents 1 or 2, where if e is 2, then each (L 11 -HAr) may be the same as or different from each other;

[0052] *Indicates the same as L 11 The site of connection;

[0053] In Formulas 1 and 3 to 5,

[0054] L3 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; and

[0055] Ar3 and Ar4 each independently represent hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.

[0056] Beneficial Effects of the Invention

[0057] The organic electroluminescent compound according to the present disclosure exhibits performance suitable for an organic electroluminescent device. In addition, by including a plurality of host materials according to the present disclosure, an organic electroluminescent device is provided, which has a lower driving voltage, a higher luminous efficiency, a higher power efficiency and / or an excellent lifespan characteristic compared to a conventional organic electroluminescent device, and can be used to manufacture a display device or a light-emitting device. DETAILED DESCRIPTION

[0058] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure.

[0059] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device as necessary.

[0060] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained 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 luminescence auxiliary material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0061] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both the material contained in the organic electroluminescent device before (e.g., before vapor deposition) and the material contained in the organic electroluminescent device after (e.g., after vapor deposition). For example, a variety of organic electroluminescent materials may be a combination of two or more compounds that may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Such two or more compounds may be included in the same or different layers, and may be mixed evaporated or co-evaporated, or deposited separately.

[0062] The term "multiple host materials" in the present disclosure means an organic electroluminescent material in which at least two host materials are combined, which may mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of the present disclosure may be included in any light-emitting layer constituting the organic electroluminescent device, wherein two or more compounds included in the multiple host materials may be included together in one light-emitting layer or may be included in different light-emitting layers, respectively. If two or more host materials are included in one layer, for example, they may be mixed-evaporated to form a layer, or they may be co-evaporated individually and simultaneously to form a layer.

[0063] Herein, the term "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above-mentioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like. The term "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30) alkynyl" means a straight or branched alkynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. The term "(C3-C30) cycloalkyl" means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl having 3 to 7, preferably 5 to 7 ring skeleton atoms and comprising at least one heteroatom, the heteroatom being selected from the group consisting of B, N, O, S, Si and P, preferably the group consisting of O, S and N. The above-mentioned heterocycloalkyl may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term "(C6-C30) (sub)aryl" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, the monocyclic or condensed ring group may be partially saturated. The number of ring skeleton carbon atoms is preferably 6 to 25 and more preferably 6 to 18. The above-mentioned aryl includes those having a spiro structure. The above-mentioned aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthyl, perylene, The aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacetyl, pyrenyl, 1- Base, 2- Base, 3- Base, 4- Base, 5- Base, 6- Benzo[c]phenanthrenyl, benzo[g] 1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl phenyl, 4'-methylbiphenyl, 4"-tert-butyl-4-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4 ... 9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 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, 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-11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl ] fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11 ,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-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, etc. ,

[0064] The term "(3- to 30-membered) (sub) heteroaryl" means an aryl or arylene group having 3 to 30 ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si and P. The number of heteroatoms is preferably 1 to 4. The above-mentioned (sub) heteroaryl can be a monocyclic ring or a condensed ring condensed with at least one benzene ring, and can be partially saturated. In addition, the above-mentioned (sub) heteroaryl includes a form in which at least one heteroaryl or aryl is connected to a heteroaryl via one or more single bonds, and also includes those with a spiro structure. The above heteroaryl groups may include monocyclic heteroaryl groups, such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and condensed ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzothiophenyl, dibenzofuranyl, dibenzothiophenyl ... benzothiophene, benzofuranyl, naphthiobenzothiophene, benzofuranoquinolyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthiopyrimidinyl, benzothiophenoquinolyl, benzothiophenoquinazolinyl, benzothiophenonaphthyridinyl, benzothiophenopyrimidinyl, naphthiophenopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuranopyrazinyl, naphthiophenopyrimidinyl oxazine, benzothienopyrazinyl, naphthienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl , dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolephenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzoperimidinyl, indolecarbazolyl, indenocarbazolyl, etc. More specifically, the heteroaryl group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolyl, 3-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 8-indolyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl,3-pyridyl, 4-pyridyl, 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-furanyl, 3-furanyl, 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, 11-phenanthridinyl, 12-phenanthridinyl, 13-phenanthridinyl, 14-phenanthridinyl, 15-phenanthridinyl, 16-phenanthridinyl, 17-phenanthridin -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-butylpyrrol-4-yl 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]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl,8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl, 1-naphtho-[2,3-b]-benzofuranyl, 2-naphtho-[2,3-b]-benzofuranyl, 3-naphtho-[2,3-b]-benzofuranyl, 4-naphtho-[2, 3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4-naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, ,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 phenyl, 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 [1,2-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 Thienyl, 2-naphtho-[2,1-b]-benzothienyl, 3-naphtho-[2,1-b]-benzothienyl, 4-naphtho-[2,1-b]-benzothienyl, 5-naphtho-[2,1-b]-benzothienyl, 6-naphtho-[2,1-b]-benzothienyl, 7-naphtho-[2,1-b]-benzothienyl, 8-naphtho-[ 2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl,9-Benzofuro[3,2-d]pyrimidinyl, 2-Benzothiol[3,2-d]pyrimidinyl, 6-Benzothiol[3,2-d]pyrimidinyl, 7-Benzothiol[3,2-d]pyrimidinyl, 8-Benzothiol[3,2-d]pyrimidinyl, 9-Benzothiol[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-Benzothiol[3,2-d]pyrazinyl 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-dibenzoselenophene, 2-dibenzoselenophene, 3-dibenzoselenophene, 4-dibenzoselenophene, etc. In the present disclosure, "halogen" includes F, Cl, Br and I. 、

[0065] In addition, "ortho (o-)", "meta (m-)" and "para (p-)" are prefixes that indicate the relative positions of substituents, respectively. Ortho means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta means that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para means that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0066] In addition, the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent), and also includes substitution by a group in which two or more substituents are connected. For example, "a substituent in which two or more substituents are connected" may be pyridine-triazine. That is, pyridine-triazine can be interpreted as a heteroaryl substituent or a substituent in which two heteroaryl substituents are connected.In the formula of the present disclosure, the substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted nitrogen-containing heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted condensed ring of one or more aliphatic rings and one or more aromatic rings are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy alkyl; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, which is unsubstituted or substituted with at least one of one or more (C1-C30)alkyl and one or more (C6-C30)aryl; (C6-C30)aryl, which is unsubstituted or substituted with at least one of deuterium, cyano, one or more (C1-C30)alkyl, one or more (C3-C30)cycloalkyl, one or more tri(C1-C30)alkylsilyl, one or more (C6-C30)aryl and one or more (3- to 30-membered)heteroaryl. ; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; a condensed ring of one or more (C3-C30)aliphatic rings and one or more (C6-C30)aromatic rings; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; (C1-C30)alkyl(C2-C30)alkenylamino; one or more mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; mono- or di-(3- to 30-membered)heteroaryl amino; (C1-C30)alkyl(3- to 30-membered)heteroarylamino; (C2-C30)alkenyl(C6-C30)arylamino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: deuterium; cyano; (C1-C20) alkyl; (C6-C25) cycloalkyl; unsubstituted or substituted with at least one (C6-C25) aryl (5- to 25-membered) heteroaryl; one or more (C6-C25) aryl groups that are unsubstituted or substituted with at least one of deuterium, cyano, one or more (C1-C20) alkyl, one or more (C6-C25) cycloalkyl, one or more tri(C1-C20) alkylsilyl, one or more (C6-C25) aryl and one or more (5- to 25-membered) heteroaryl; mono- or di-(C6-C25) arylamino; mono- or di-(5- to 25-membered) heteroarylamino; and (C6-C25) aryl (5- to 25-membered) heteroarylamino. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: deuterium; cyano; (C1-C10) alkyl; (C6-C18) cycloalkyl; (5- to 20-membered) heteroaryl, unsubstituted or substituted with at least one (C6-C18) aryl; one or more (C6-C25) aryl groups, unsubstituted or substituted with at least one of the following: deuterium, cyano, one or more (C1-C10) alkyl, one or more (C6-C18) cycloalkyl, one or more tri(C1-C10) alkylsilyl, one or more (C6-C15) aryl and one or more (5- to 20-membered) heteroaryl; di-(C6-C18) arylamino; and (C6-C18) aryl (5- to 20-membered) heteroarylamino. Specifically, the substituents can each independently be at least one of the following: deuterium; cyano; methyl; cyclohexyl; substituted or unsubstituted phenyl; naphthyl; phenylnaphthyl; biphenyl; methylfluorenyl; dimethylfluorenyl; diphenylfluorenyl; phenanthrenyl; anthracenyl; fluoranthenyl; terphenyl;. The invention can be any of the following: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 67, 68, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 112, 113, 114, 129, 130, 131, 132, 143, 159, 144, 15

[0067] In the formula of the present disclosure, if a substituent is connected to an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted, monocyclic or polycyclic (3 to 30 yuan) alicyclic ring or aromatic ring, or a combination thereof formed by connecting at least two adjacent substituents. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 20, and according to another embodiment of the present disclosure, the number of ring skeleton atoms is 5 to 15.

[0068] In the formula of the present disclosure, the heteroaryl group, the heteroarylene group and the heterocycloalkyl group may each independently contain at least one heteroatom selected from B, N, O, S, Si and P. In addition, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkylsilyl, substituted or unsubstituted di(C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri ... C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0069] The present disclosure provides an organic electroluminescent device including a compound represented by the following Formula 2′ or Formula 2″. Herein, the organic electroluminescent compound having Formula 2′ or Formula 2″ may be included in a light emitting layer or an electron transporting layer.

[0070] Hereinafter, the compound represented by Formula 2' will be described in more detail.

[0071] Ar 11 (L 11 -HAr) e -----(2′)

[0072] In formula 2',

[0073] HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidyl group, or a substituted or unsubstituted benzothienopyrimidinyl group;

[0074] L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0075] Ar 11 Each independently represents any one of the following formulae 3 to 5:

[0076]

[0077]

[0078] In equations 3 to 5,

[0079] Y2 represents O or S;

[0080] R 20 To R 29 represents hydrogen or deuterium;

[0081] e represents 1 or 2, where if e is 2, then each (L 11 -HAr) may be the same as or different from each other; and

[0082] *Indicates the same as L 11 The site of connection;

[0083] Provided that, when HAr is a substituted triazine group, the substituents of the substituted triazine group are each independently selected from deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dimethylfluorenyl, fluoranthenyl, A substituent group is a carbazolyl group, a carbazolyl group, and a combination thereof, and when there are two substituent groups, the two substituent groups are the same as or different from each other.

[0084] The compound represented by Formula 2' may be at least one selected from the following compounds, but is not limited thereto.

[0085]

[0086]

[0087]

[0088] Hereinafter, the compound represented by Formula 2" will be described in more detail. 11 (L11 -HAr) e -----(2″)

[0089] In formula 2",

[0090] HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group;

[0091] L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;

[0092] Ar 11 Each independently represents any one of the following formulae 3 to 5:

[0093]

[0094] In equations 3 to 5,

[0095] Y2 represents O or S;

[0096] R 21 To R 24 and R 26 To R 29 each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0097] R 20 and R 25 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0098] e represents 1 or 2, where if e is 2, then each (L 11 -HAr) may be the same as or different from each other; and

[0099] *Indicates the same as L 11 The site of connection.

[0100] The compound represented by Formula 2" may be at least one selected from the following compounds, but is not limited thereto.

[0101]

[0102]

[0103]

[0104] The plurality of host materials according to one embodiment of the present disclosure include a first host material including a compound represented by Formula 1 and a second host material including a compound represented by Formula 2, and the plurality of host materials may be included in a light emitting layer of an organic electroluminescent device according to one embodiment of the present disclosure.

[0105] Hereinafter, the compound represented by Formula 1 will be described in more detail.

[0106] In Formula 1, X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that any one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -NR5-, -O-, or -S-. According to one embodiment of the present disclosure, any one of X1 and Y1 represents -N=, and the other of X1 and Y1 represents -O- or -S-. That is, X1 may be -N=, and Y1 may be -O-; X1 may be -N=, and Y1 may be -S-; X1 may be -O-, and Y1 may be -N=; or X1 may be -S-, and Y1 may be -N=.

[0107] In Formula 1, R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted (5- to 20-membered) heteroaryl group. For example, R1 can be an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, a fluorenyl group substituted with one or more methyl groups, a benzofluorenyl group substituted with one or more methyl groups, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, a spiro[fluorene-fluorene] group, a spiro[fluorene-benzofluorene] group, an unsubstituted pyridyl group, and the like.

[0108] In Formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L1 represents a single bond, or a substituted or unsubstituted (C6-C18)arylene group. According to another embodiment of the present disclosure, L1 represents a single bond, or an unsubstituted (C6-C12)arylene group. For example, L1 may be a single bond, an unsubstituted phenylene group, an unsubstituted naphthylene group, or the like.

[0109] In Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (3- to 20-membered) heteroaryl group. According to another embodiment of the present disclosure, Ar1 and Ar2 each independently represent an unsubstituted (C6-C25)aryl group which is substituted by at least one of the following: deuterium, one or more (C1-C6)alkyl groups, one or more (C6-C25)aryl groups, one or more (3- to 20-membered)heteroaryl groups, one or more (C3-C7)cycloalkyl groups, and one or more (C1-C6)alkyl (C6-C12)aryl groups; or an unsubstituted (3- to 20-membered)heteroaryl group which is substituted by any one of one or more (C6-C12)aryl groups and one or more (5- to 15-membered)heteroaryl groups. For example, Ar1 and Ar2 can each independently be substituted phenyl, naphthyl, biphenyl, phenanthryl, dimethylfluorenyl, diphenylfluorenyl, naphthylphenyl, phenylnaphthyl, dimethylbenzofluorenyl, terphenyl, spirobifluorenyl, benzofuranyl, benzothiophenyl, dibenzothiophenyl unsubstituted or substituted with one or more phenyl groups, dibenzofuranyl unsubstituted or substituted with one or more phenyl groups or one or more pyridyl groups, carbazolyl substituted with one or more phenyl groups, benzonaphthofuranyl, benzonaphthothiophenyl, benzofuranopyridyl, etc.; wherein the substituent of the substituted phenyl group can be at least one of the phenyl groups substituted with the following: deuterium, one or more methyl groups and one or more tert-butyl groups; anthracenyl; fluoranthene; phenylfluorenyl; cyclohexyl; pyridyl substituted with one or more phenyl groups; phenoxazinyl; and benzimidazolyl substituted with one or more phenyl groups.

[0110] In Formula 1, R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C 30) alkyl (C6-C30) aryl silyl, substituted or unsubstituted (C1-C30) alkyl di (C6-C30) aryl silyl, substituted or unsubstituted tri (C6-C30) aryl silyl, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N-(Ar3)(Ar4); or may be connected to adjacent substituents to form a ring. According to one embodiment of the present disclosure, R2 to R5 each independently represent hydrogen, or a substituted or unsubstituted (C6-C12) aryl group. According to another embodiment of the present disclosure, R2 to R5 each independently represent hydrogen, or an unsubstituted (C6-C12) aryl group. For example, R2 and R3 may be hydrogen, and R4 may be hydrogen, phenyl, etc.

[0111] In Formula 1, a represents 1; b and c each independently represent 1 or 2, preferably 1; d represents an integer of 1 to 4, preferably 1 or 2; and when b to d are integers of 2 or more, each R2 to each R4 may be the same as or different from each other.

[0112] According to one embodiment of the present disclosure, Formula 1 may be represented by at least one of the following Formulas 1-1 to 1-4:

[0113]

[0114]

[0115] In Formulae 1-1 to 1-4, R1 to R4, Ar1, Ar2, L1, and a to d are as defined in Formula 1.

[0116] Hereinafter, the compound represented by Formula 2 will be described in more detail.

[0117] In Formula 2, HAr each independently represents a substituted or unsubstituted nitrogen-containing (3- to 20-membered) heteroaryl group. According to one embodiment of the present disclosure, HAr each independently represents a substituted or unsubstituted nitrogen-containing (5- to 15-membered) heteroaryl group. According to another embodiment of the present disclosure, HAr each independently represents a nitrogen-containing (5- to 15-membered) heteroaryl group that is unsubstituted or substituted by at least one of the following: deuterium; (C1-C6) alkyl; (C6-C20) aryl group that is unsubstituted or substituted by at least one of deuterium, one or more (C1-C6) alkyl groups, and one or more (C6-C12) aryl groups; (5- to 15-membered) heteroaryl group that is unsubstituted or substituted by one or more (C6-C12) aryl groups; and (C1-C6) alkyl (C6-C20) aryl group. For example, HAr can be each independently a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazoline, a substituted or unsubstituted benzoquinazoline, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted triazanaphthyl, substituted or unsubstituted benzofuranopyrimidinyl, or substituted or unsubstituted benzothiophenopyrimidinyl, etc., wherein the substituent can be any one of the following: deuterium, methyl, phenyl, phenyl substituted with at least one deuterium, naphthylphenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, phenanthrenyl, fluoranthenyl, terphenyl, phenyl, triphenylene, phenylpyridyl, dibenzofuranyl, dibenzothiophenyl and phenylcarbazolyl.

[0118] In formula 2, L 11 Each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group. According to one embodiment of the present disclosure, L 11 Each independently represents a single bond, a substituted or unsubstituted (C6-C15)arylene group, or a substituted or unsubstituted (5- to 15-membered)heteroarylene group. According to another embodiment of the present disclosure, L 11 Each independently represents a single bond, an unsubstituted (C6-C15)arylene group which is substituted with one or more (C6-C12)aryl groups, or an unsubstituted (5- to 15-membered)heteroarylene group. 11 Each of them independently may be a single bond, a phenylene group, a naphthylene group, a biphenylene group, a phenylene group substituted with one or more phenyl groups, a dibenzofuranyl group, or the like.

[0119] In formula 2, Ar 11 Each independently represents any one of the following formulae 3 to 5.

[0120]

[0121]

[0122] In Formulae 3 to 5, Y2 represents O or S.

[0123] In Formulas 3 to 5, R 20 To R 29 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or -L3-N-(Ar3)(Ar4). According to one embodiment of the present disclosure, R 20 To R 29 Each independently represents hydrogen, substituted or unsubstituted (C6-C20) aryl, or substituted or unsubstituted (5- to 15-membered) heteroaryl. According to another embodiment of the present disclosure, R 20 To R 29 Each independently represents hydrogen; (C6-C20)aryl which is unsubstituted or substituted by at least one of deuterium, one or more cyano groups, one or more (C6-C12)aryl groups and one or more (5- to 15-membered)heteroaryl groups; or (5- to 15-membered)heteroaryl which is unsubstituted or substituted by one or more (C6-C12)aryl groups. For example, R 20 To R 29 Each of them can independently be hydrogen, phenyl, phenyl substituted by at least one deuterium, phenyl substituted by one or more cyano groups, naphthylphenyl, phenyl substituted by one or more dibenzothiophenyl groups, naphthyl, phenylnaphthyl, biphenyl, biphenyl substituted by at least one cyano group, phenanthryl, pyridyl, pyridyl substituted by one or more phenyls, isoquinolyl, carbazolyl substituted by one or more phenyls, dibenzofuranyl, dibenzothiophenyl, etc.

[0124] In Formula 2, e represents 1 or 2, and when e is 2, each (L 11-HAr) may be the same as or different from each other.

[0125] In formulas 3 to 5, * indicates 11 The site of connection.

[0126] In Formulae 1 and 3 to 5, L3 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3-membered to 30-membered)heteroarylene group.

[0127] In Formulas 1 and 3 to 5, Ar3 and Ar4 each independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group.

[0128] The compound represented by Formula 1 may be at least one selected from the following compounds, but is not limited thereto.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] The compound represented by Formula 2 may be at least one selected from the following compounds, but is not limited thereto.

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] A combination of at least one of Compounds H1-1 to H1-136 and at least one of Compounds C-1 to C-127 can be used in an organic electroluminescent device.

[0144] The compound having Formula 1 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art, for example, by referring to Korean Patent Application Publication No. 2017-0022865 (published on March 2, 2017), Korean Patent Application Publication No. 2017-0051198 (published on May 11, 2017), Korean Patent Application Publication No. 2018-0094572 (published on August 24, 2018), etc., but is not limited thereto.

[0145] The compound having Formula 2 according to the present disclosure can be prepared by a synthetic method known to those skilled in the art, for example, by referring to the following Reaction Schemes 1 to 3, but is not limited thereto.

[0146] [Reaction Scheme 1]

[0147]

[0148] [Reaction Scheme 2]

[0149]

[0150] [Reaction Scheme 3]

[0151]

[0152] In reaction schemes 1 to 3, Y2, R 20 To R 29 , L 11 , HAr and e are as defined in Formula 2, and Hal is a halogen atom.

[0153] Although illustrative synthesis examples of the compounds represented by Formula 2 are described above, those skilled in the art will be able to easily understand that they are all based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, acidified montmorillonite (H-mont)-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd (II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration cyclization reaction, SN1 substitution reaction, SN2 substitution reaction, phosphine-mediated reductive cyclization reaction, etc., and the above reactions proceed even if substituents defined in Formula 2 but not specified in the specific synthesis example are bonded.

[0154] The organic electroluminescent device of the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include a plurality of organic electroluminescent materials, and the plurality of organic electroluminescent materials include a compound represented by Formula 1 as a first organic electroluminescent material, and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer may include a compound represented by Formula 1 and a compound represented by Formula 2.

[0155] The light-emitting layer includes one or more hosts and a dopant, wherein the host includes a plurality of host materials, wherein the compound represented by Formula 1 may be included as a first host compound of the plurality of host materials, and the compound represented by Formula 2 may be included as a second host compound of the plurality of host materials. Herein, the weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0156] In the present disclosure, the light-emitting layer is a layer that emits light, which may be a single layer or a plurality of layers in which two or more layers are stacked. Among the various host materials of the present disclosure, the first and second host materials may be respectively contained in one layer or in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound of the light-emitting layer may be less than 20wt%.

[0157] The organic electroluminescent device according to the present disclosure may include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, in addition to the various host materials according to the present disclosure, the organic electroluminescent device according to the present disclosure may further include an amine-based compound as at least one of a hole injection material, a hole transport material, a hole auxiliary material, a luminescent material, a luminescent auxiliary material, and an electron blocking material. In addition, according to one embodiment of the present disclosure, in addition to the various host materials according to the present disclosure, the organic electroluminescent device according to the present disclosure may further include an azine-based compound as at least one of an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.

[0158] The various host materials according to the present disclosure can be used as light-emitting materials for white organic light-emitting devices. Various structures of white organic light-emitting devices have been proposed, such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting components, or a color conversion material (CCM) method, etc. In addition, the various host materials according to the present disclosure can also be used in organic electroluminescent devices containing QDs (quantum dots).

[0159] 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 a multilayer in order to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayers. In addition, the hole injection layer may be doped with a p-type dopant. The electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may block the overflow of electrons from the light-emitting layer and confine the excitons in the light-emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer may be a multilayer, wherein a variety of compounds may be used in each of the multilayers.

[0160] 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 a layer to facilitate the control of electron injection and improve the interface characteristics between the light emitting layer and the electron injection layer, wherein two compounds may be used simultaneously in each of the multiple layers. The hole blocking layer or the electron transport layer may also be a multilayer, wherein a plurality of compounds may be used in each of the multiple layers. In addition, the electron injection layer may be doped with an n-type dopant.

[0161] The dopant that can be included in the organic electroluminescent device of the present disclosure can be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but can be selected from metallized iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) complex compounds, and can be preferably selected from ortho-metallized iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) complex compounds, and can more preferably be ortho-metallized iridium complex compounds.

[0162] The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following Formula 101, but is not limited thereto.

[0163]

[0164] In formula 101,

[0165] L' is selected from the following structures 1 to 3:

[0166]

[0167] R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to adjacent substituents to form one or more rings together with pyridine, such as substituted or unsubstituted quinoline, isoquinoline, benzofuranopyridine, benzothienopyridine, indenopyridine, benzofuranoquinoline, benzothienoquinoline, or indenoquinoline rings;

[0168] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be linked to an adjacent substituent to form a ring with benzene, such as a substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuranopyridine, or benzothienopyridine ring;

[0169] R 201 To R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be connected with adjacent substituents to form a ring; and

[0170] s represents an integer of 1 to 3.

[0171] Specific examples of the dopant compound are as follows, but are not limited thereto.

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] Each layer of the organic electroluminescent device disclosed herein can be formed by any of the following methods: dry film forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film forming methods such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating, etc.

[0179] When a wet film-forming method is used, a thin film can be formed by dissolving or diffusing a material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. There is no particular limitation on the solvent as long as the material forming each layer is soluble or dispersible in the solvent, which does not cause any problem in forming a film.

[0180] In addition, the first and second host compounds according to the present disclosure can be formed into films by the above-listed methods, usually by co-evaporation or mixed evaporation methods. Co-evaporation is a mixed deposition method in which two or more materials are placed in a corresponding single crucible source and current is applied to two chambers at the same time to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation, and current is applied to the chamber to evaporate the materials. In addition, when the first and second host compounds are present in the same layer or different layers in the organic electroluminescent device, the two host compounds can form films separately. For example, the second host compound can be evaporated after the first host compound is evaporated.

[0181] The present disclosure can provide a display system by using an organic electroluminescent compound represented by Formula 2' or Formula 2" or by using a variety of host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display system or a lighting system can be produced by using an organic electroluminescent compound represented by Formula 2' or Formula 2" or by using a variety of host materials of the present disclosure. Specifically, a display system, such as a display system for a white organic light-emitting device, a smartphone, a tablet computer, a notebook computer, a PC, a TV, or a car; or a lighting system, such as an outdoor or indoor lighting system, can be produced.

[0182] Hereinafter, the preparation method of the disclosed compound and its characteristics, and the characteristics of the organic electroluminescent device containing various host materials according to the present disclosure will be explained in detail with reference to the representative compounds of the present disclosure. The following examples only describe the characteristics of the organic electroluminescent device containing the compound according to the present disclosure or various host materials, but the present disclosure is not limited to the following examples.

[0183] Example 1: Preparation of Compound H1-27

[0184]

[0185] Synthesis of compound 1

[0186] Dibenzofuran-2-amine (20g, 144.7mmol), 2-bromodibenzofuran (23.8g, 96.47mmol), Pd(OAc)2 (1.1g, 4.82mmol), 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (S-Phos) (3.9g, 9.65mmol), NaOt-Bu (13.9g, 144.7mmol) and 485mL o-xylene were added to a flask and stirred for 3 hours at 160°C. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound 1 (4.9g, yield: 10%).

[0187] Synthesis of compound H1-27

[0188] Compound 1 (4.9 g, 12.76 mmol), compound 2 (4.2 g, 14.0 mmol), Pd (dba 3 ) 2 (0.584 g, 0.638 mmol), S-Phos (0.523 g, 1.276 mmol), NaOt-Bu (1.8 g, 19.14 mmol) and 65 mL of o-xylene were added to a flask and stirred at 160 ° C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-27 (5.6 g, yield: 68.3%).

[0189] Compound MW Melting point H1-27 642.19 237℃

[0190] Example 2: Preparation of Compound H1-46

[0191]

[0192] Compound 3 (25g, 74.48mmol), compound 2 (42.58g, 81.93mmol), Pd (OAc) 2 (0.16g, 7.5mmol), P (t-Bu) 3 (0.28g, 7.5mmol), NaOt-Bu (14.31g, 150mmol) and 284.09mL o-xylene were added to a flask and stirred at 160°C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-46 (23.4g, yield: 50%).

[0193] Compound MW Melting point H1-46 628.22 256.5℃

[0194] Example 3: Preparation of Compound H1-43

[0195]

[0196] Compound 4 (20 g, 56.96 mmol), compound 2 (18.8 g, 57.13 mmol), Pd (OAc) 2 (0.13 g, 5.7 mmol), P (t-Bu) 3 (0.22 g, 5.7 mmol), NaOt-Bu (11 g, 113.92 mmol) and 227.27 mL of o-xylene were added to a flask and stirred at 160 ° C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-43 (12.5 g, yield: 34%)

[0197] Compound MW Melting point H1-43 644.19 249℃

[0198] Example 4: Preparation of Compound H1-123

[0199]

[0200] Synthesis of compound 5

[0201] 3-aminobiphenyl (54g, 319mmol), 3-bromobiphenyl (70g, 301mmol), Pd(OAc)2(0.33g, 1.47mmol), tricyclohexylphosphine (0.84g, 2.8mmol), NaOt-Bu (57g, 593mmol) and 280mL toluene are added in a flask, and stirred at 95°C for 8 hours. After the reaction is complete, the mixture is cooled to room temperature. The organic layer is extracted with ethyl acetate, and magnesium sulfate is used to remove residual moisture. The residue is dried and separated by column chromatography to obtain compound 5 (60.23g, yield: 85%).

[0202] Synthesis of compound H1-123

[0203] Compound 5 (60.23 g, 187.5 mmol), compound 2 (60 g, 182.33 mmol), Pd (OAc) 2 (0.41 g, 1.83 mmol), S-Phos (1.74 g, 4.23 mmol), NaOt-Bu (26.23 g, 272 mmol) and 300 mL of xylene were added to a flask and stirred at 110 ° C for 10 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-123 (36.9 g, yield: 33%).

[0204] Compound MW Melting point H1-123 614.24 210℃

[0205] Example 5: Preparation of Compound H1-136

[0206]

[0207] Synthesis of compound 6

[0208] Dibenzofuran-2-amine (29.24g, 159.7mmol), 2-bromodibenzothiophene (40g, 152.7mmol), Pd(OAc)2 (0.17g, 0.75mmol), tricyclohexylphosphine (0.43g, 1.45mmol), NaOt-Bu (29.22g, 304mmol) and 250mL toluene are added to a flask and stirred at 95°C for 8 hours. After the reaction is complete, the mixture is cooled to room temperature. The organic layer is extracted with ethyl acetate, and magnesium sulfate is used to remove residual moisture. The residue is dried and separated by column chromatography to obtain compound 6 (17.12g, yield: 86%).

[0209] Synthesis of Compound H1-136

[0210] Compound 6 (17.12 g, 46.89 mmol), compound 2 (15 g, 45.58 mmol), Pd (OAc) 2 (0.05 g, 0.22 mmol), S-Phos (0.22 g, 0.535 mmol), NaOt-Bu (6.56 g, 68.2 mmol) and 75 mL of xylene were added to a flask and stirred at 110 ° C for 10 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-136 (10.2 g, yield: 34%).

[0211] Compound MW Melting point H1-136 658.17 254℃

[0212] Example 6: Preparation of Compound H1-85

[0213]

[0214] Compound 2 (5.0 g, 15.2 mmol), di([1,1'-biphenyl]-4-yl)amine (4.9 g, 15.2 mmol), Pd(OAc)2 (0.2 g, 0.8 mmol), P(t-Bu)3 (0.8 mL, 1.5 mmol), NaOt-Bu (2.9 g, 30.4 mmol) and 76 mL of xylene were added to a flask and stirred at 160 ° C for 5 hours. After the reaction was completed, the mixture was cooled to room temperature. The precipitated solid was washed with distilled water and methanol and separated by column chromatography to obtain compound H1-85 (5.5 g, yield: 59%).

[0215] Example 7: Preparation of Compound H1-51

[0216]

[0217] Compound 2 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]amine (6.8 g, 13 mmol), Pd(OAc)2(0.3 g, 1 mmol), S-Phos(0.9 g, 2 mmol), Cs2CO3(11.5 g, 35 mmol), 60 mL of o-xylene, 15 mL of EtOH and 15 mL of distilled water were added to a flask and stirred at 150°C under reflux for 3 hours. After the reaction was completed, the mixture was cooled to room temperature and washed with distilled water. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-51 (2.2 g, yield: 27%).

[0218] Example 8: Preparation of Compound H1-68

[0219]

[0220] Compound 7 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (5 g, 12.47 mmol), Pd(PPh3)4 (0.4 g, 0.34 mmol), Na2CO3 (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol and 14 mL of distilled water were added to a flask and stirred at 120°C for 4 hours. After the reaction was complete, the mixture was added dropwise to methanol and the resulting solid was filtered. The resulting solid was purified by column chromatography to obtain compound H1-68 (1.4 g, yield: 20.0%).

[0221] Example 9: Preparation of Compound H1-15

[0222]

[0223] Synthesis of compound 8

[0224] Compound 2 (10.0 g, 30.3 mmol), [1,1'-biphenyl]-3-amine (6.7 g, 39.4 mmol), Pd(OAc)2 (0.34 g, 1.5 mmol), P(t-Bu)3 (1.5 mL, 3.03 mmol), NaOt-Bu (5.8 g, 60.6 mmol) and 150 mL of xylene were added to a flask and stirred at 160 ° C for 6 hours. After the reaction was completed, the mixture was washed with distilled water. The organic layer was extracted with ethyl acetate and dried over magnesium sulfate. A rotary evaporator was used to remove the solvent. The residue was separated by column chromatography to obtain compound 8 (10.8 g, yield: 36%).

[0225] Synthesis of Compound H1-15

[0226] Compound 8 (5.0 g, 10.8 mmol), 3-bromodibenzofuran (3.2 g, 12.9 mmol), Pd2(dba)3 (0.5 g, 0.54 mmol), S-Phos (0.45 g, 1.08 mmol), NaOt-Bu (2.0 g, 21.6 mmol) and 60 mL of o-xylene were added to a flask and stirred at 160 ° C for 6 hours. After the reaction was completed, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate, and magnesium sulfate was used to remove residual moisture. The residue was dried and separated by column chromatography to obtain compound H1-15 (1.45 g, yield: 21%).

[0227] Compound MW Melting point H1-15 628.73 205℃

[0228] Example 10: Preparation of Compound C-2

[0229]

[0230] 11-Chlorobenzo[b]naphtho[2,3-d]thiophene (3.6 g, 13.4 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (6.4 g, 14.77 mmol), Pd2(dba)3 (613 mg, 0.67 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (550 mg, 1.34 mmol), K3PO4 (7.1 g, 33.5 mmol) and 70 mL of o-xylene were added to a flask and stirred at reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized with o-xylene to obtain compound C-2 (3.0 g, yield: 41.3%).

[0231] Compound MW Melting point C-2 541.2 301℃

[0232] Example 11: Preparation of Compound C-57

[0233]

[0234] 11-Chlorobenzo[b]naphtho[2,3-d]furan (1.4 g, 5.5 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (2.7 g, 6.1 mmol), Pd2(dba)3 (252 mg, 0.275 mmol), S-Phos (225 mg, 0.55 mmol), K3PO4 (2.9 g, 13.75 mmol) and 30 mL of o-xylene were added to a flask and stirred at reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and filtered through silica gel. The organic layer was distilled under reduced pressure and recrystallized with o-xylene to obtain compound C-57 (0.9 g, yield: 30%).

[0235] Compound MW Melting point C-57 525.61 265.5℃

[0236] Device Examples 1 and 2: Production of Red-Emitting OLEDs Deposited with Compounds According to the Disclosure as Hosts

[0237] OLED according to the present disclosure is produced. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate for OLED (GEOMATECCO., LTD., Japan) is ultrasonically washed with acetone and isopropanol in sequence, and then stored in isopropanol before use. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 of Table 3 is introduced into a chamber of a vacuum vapor deposition device, and compound HT-1 of Table 3 is introduced into another chamber. By doping compound HI-1 in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1, the two materials are evaporated at different rates to deposit a hole injection layer with a thickness of 10nm. Subsequently, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80nm. Subsequently, compound HT-2 is introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby depositing a second hole transport layer with a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: the compound of Table 1 below was introduced as a host into a chamber of a vacuum vapor deposition device, and the compound D-39 was introduced as a dopant into another chamber, followed by doping with a dopant in an amount of 3 wt% based on the total amount of the host and the dopant to deposit a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Subsequently, the compound ETL-1: compound EIL-1 was evaporated at a rate of 1:1 to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing the compound EIL-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition device to produce an OLED.

[0238] Comparative Example 1: Production of a red-emitting OLED deposited with a conventional compound as a host

[0239] An OLED was produced in the same manner as in Device Examples 1 and 2, except that Compound A of the following Table 3 was used as a host of the light-emitting layer.

[0240] The driving voltage, luminous efficiency, power efficiency, and luminescent color based on a luminance of 1,000 nit of the organic electroluminescent devices of Device Examples 1 and 2 and Comparative Example 1 prepared as described above are shown in Table 1 below.

[0241] [Table 1]

[0242]

[0243] Table 1 shows that the organic electroluminescent device including the organic electroluminescent compound according to the present disclosure as a host exhibits luminous efficiency comparable to that of Comparative Example 1, while providing excellent driving voltage and power efficiency characteristics compared to Comparative Example 1. The organic electroluminescent device including the host material according to the present disclosure may also have advantages in terms of lifespan characteristics.

[0244] The LUMO level, HOMO level and triplet energy of the parent structure of the organic electroluminescent compound represented by Formula 2' and the organic electroluminescent compound represented by Formula 2" according to the present disclosure were measured, respectively, and are shown in the following Table 1-1.

[0245] [Table 1-1]

[0246]

[0247]

[0248] *The structure was optimized by applying the background sets of B3LYP and 6-31G(d), which are hybrid DFT (hybrid density functional theory) with Gaussian 16, a quantum chemical calculation program of Gaussian, and the triplet state was calculated using TD-DFT (time-dependent DFT).

[0249] Table 1-1 above shows the parent structure of the organic electroluminescent compound represented by Formula 2" according to the present disclosure (substituents are introduced into R 20 or R 25 ) has an energy level similar to that of the parent structure of compounds C-2 and C-57, which correspond to the organic electroluminescent compounds represented by formula 2' used in device examples 1 and 2. Therefore, it is expected that an organic electroluminescent device using the organic electroluminescent compound represented by formula 2" as a host material will also have device characteristics similar to those of device examples 1 and 2.

[0250] Device Examples 3 to 5: Production of Red-Emitting Nanostructured ... OLED

[0251] An OLED was produced in the same manner as in Device Examples 1 and 2, except that the first host compound and the second host compound shown in Table 2 below were added as hosts to two chambers of a vacuum vapor deposition apparatus, respectively, and compound D-39 was introduced as a dopant into another chamber, and then the two host materials were evaporated at a rate of 1:1 and the dopant was evaporated at different rates simultaneously, thereby doping the dopant in an amount of 3 wt % based on the total amount of the host and the dopant to deposit the light-emitting layer.

[0252] The driving voltage, luminous efficiency, and luminescent color of the organic electroluminescent devices of Device Examples 3 to 5 prepared as described above based on a luminance of 1,000 nits are shown in Table 2 below.

[0253] [Table 2]

[0254]

[0255] It was previously determined in Device Examples 1 and 2 that when the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present disclosure is used as a single host, an OLED having excellent luminous efficiency, driving voltage and power efficiency characteristics is provided. In addition, Table 2 shows that the organic electroluminescent device comprising a plurality of host materials according to the present disclosure as a host provides improved driving voltage, luminous efficiency and / or power efficiency characteristics compared to the organic electroluminescent device comprising the organic electroluminescent compound represented by Formula 2' or Formula 2" of the present disclosure as a single host. The organic electroluminescent device comprising a plurality of host materials according to the present disclosure may also have advantages in terms of lifespan characteristics.

[0256] Without being limited by theory, the light-emitting layer is made into an electron-dominated system by using the compound of Formula 2 according to the present disclosure as the second host, and the compound of Formula 1 according to the present disclosure (which is an amine-based compound) is used as the first host to provide sufficient excitons by providing a large number of holes. In addition, without being limited by theory, the HOMO barrier between the hole transport layer and the light-emitting layer can be reduced due to the high HOMO energy level of the first host. Therefore, low driving voltage, high power efficiency and long life characteristics can be obtained.

[0257] The compounds used in Device Examples 1 to 5 and Comparative Example 1 are shown in Table 3 below.

[0258] [Table 3]

[0259]

[0260] Device Example 6: Production of a blue-emitting OLED deposited with a compound according to the present disclosure as an electron transport layer

[0261] Produce an OLED according to the present disclosure. First, a transparent electrode indium tin oxide (ITO) film (10Ω / sq) (Japan Gioma Co., Ltd.) on a glass substrate for OLED is ultrasonically washed with acetone and isopropanol in sequence, and then stored in isopropanol before use. The ITO substrate is mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 of Table 5 is introduced into a chamber of a vacuum vapor deposition device as a first hole injection compound, and compound HT-1 of Table 5 is introduced into another chamber. By doping compound HI-1 in an amount of 3wt% based on the total amount of compound HI-1 and compound HT-1, the two materials are evaporated at different rates to deposit a hole injection layer with a thickness of 10nm. Subsequently, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80nm. Subsequently, compound HT-3 is introduced into another chamber of a vacuum vapor deposition device, and the compound is evaporated by applying an electric current to the chamber, thereby depositing a second hole transport layer with a thickness of 5nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows: Compound BH of Table 5 was introduced as the host into a chamber of a vacuum vapor deposition device, and compound BD was introduced as a dopant into another chamber. The two host materials were evaporated at a rate of 1:1, and the dopant was evaporated at different rates at the same time, thereby doping a dopant in an amount of 3wt% based on the total amount of the host and the dopant to deposit a light-emitting layer with a thickness of 20nm on the hole transport layer. Subsequently, compound BF was deposited on the light-emitting layer as an electron buffer layer with a thickness of 5nm. Subsequently, compound C-2: compound EIL-1 was evaporated at a weight ratio of 50:50 to deposit an electron transport layer with a thickness of 30nm on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition device to produce an OLED. Each compound of the material was prepared by 10 -6 Purify by vacuum sublimation.

[0262] Comparative Example 2: Production of a blue-light-emitting OLED deposited with a conventional compound as an electron transport layer

[0263] An OLED was produced in the same manner as in Device Example 6, except that Compound A of Table 5 was used as an electron transport layer instead of Compound C-2.

[0264] The driving voltage, luminous efficiency, luminous color, and external quantum efficiency of the OLEDs produced in Device Example 6 and Comparative Example 2 prepared as described above based on a brightness of 1,000 nits are shown in Table 4 below.

[0265] [Table 4]

[0266]

[0267] Table 4 shows that, compared with the organic electroluminescent device of Comparative Example 2 including a conventional compound as an electron transport layer, the organic electroluminescent device including the compound according to the present disclosure as an electron transport layer provides excellent driving voltage, luminous efficiency and / or external quantum efficiency characteristics.

[0268] The compounds used in Device Example 6 and Comparative Example 2 are shown in Table 5 below.

[0269] [Table 5]

[0270]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 2': Year 11 (L 11 -Hair) e -----(2') in HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidyl group, or a substituted or unsubstituted benzothienopyrimidinyl group; L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar 11 Each independently represents any one of the following formulae 3 to 5: in Y2 represents O or S; R 20 To R 29 represents hydrogen or deuterium; e represents 1 or 2, where if e is 2, then each (L 11 -HAr) may be the same as or different from each other; and *Indicates the same as L 11 The site of connection; Provided that, when HAr is a substituted triazine group, the substituents of the substituted triazine group are each independently selected from deuterium, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, triphenylene, dimethylfluorenyl, fluoranthenyl, A substituent group is a carbazolyl group, a carbazolyl group, and a combination thereof, and when there are two substituent groups, the two substituent groups are the same as or different from each other.

2. An organic electroluminescent compound, which is represented by the following formula 2": Year 11 (L 11 -Hair) e -----(2") in HAr each independently represents a substituted or unsubstituted triazine group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group; L 11 each independently represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; Ar 11 Each independently represents any one of the following formulae 3 to 5: in Y2 represents O or S; R 21 To R 24 and R 26 To R 29 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; R 20 and R 25 Each independently represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; e represents 1 or 2, where if e is 2, then each (L 11 -HAr) may be the same as or different from each other; and *Indicates the same as L 11 The site of connection. 3 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 . 4 . An organic electroluminescent device comprising the organic electroluminescent compound according to claim 2 .

5. The organic electroluminescent compound according to claim 1, wherein The compound represented by formula 2' is selected from the following compounds:

6. The organic electroluminescent compound according to claim 2, wherein The compound represented by formula 2" is selected from the following compounds:

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