Various host materials and organic electroluminescent devices comprising the same

Abstract

The present disclosure relates to various host materials and organic electroluminescent devices comprising the same. By comprising a specific combination of compounds according to the present disclosure as various host materials according to the present disclosure, it is possible to provide organic electroluminescent devices having improved driving voltage, luminous efficiency, and / or lifespan characteristics compared to conventional organic electroluminescent devices.

Description

Technical Field

[0001] This disclosure relates to various host materials and organic electroluminescent devices incorporating them. Background Technology

[0002] Small-molecule green organic light-emitting diodes (OLEDs) were first developed in 1987 by Tang et al. at Eastman Kodak using a TPD / Alq3 bilayer consisting of an emissive layer and a charge transport layer. Subsequently, the development of OLEDs progressed rapidly, and they have been commercialized. Currently, OLEDs primarily utilize phosphorescent materials with excellent luminous efficiency in panel manufacturing. However, in many applications such as TVs and lighting equipment, OLEDs face the problem of insufficient lifetime, and high-efficiency OLEDs remain a necessity. Generally, higher brightness in an OLED corresponds to a shorter lifetime. Therefore, for long-term use and high resolution of displays, OLEDs with high luminous efficiency and / or long lifetimes are required.

[0003] Various materials or concepts for organic layers in OLEDs have been proposed to improve luminous efficiency, driving voltage, and / or lifetime. However, they have not been satisfactory in practical applications.

[0004] Korean Patent Application Publication No. 2020-0000329 discloses various host materials, including compounds in which a heteroaryl group is partially linked to a phenanthrene-based component and compounds in which a heteroaryl group is partially linked to a carbazole-based component. Korean Patent Application Publication No. 2017-0043439 discloses carbazole derivative compounds. However, neither of these discloses a specific combination of host materials claimed herein. Furthermore, there is a continued need to develop luminescent materials with improved performance (such as improved driving voltage, luminous efficiency, power efficiency, and / or lifetime characteristics) compared to combinations of specific compounds disclosed in the aforementioned references. Summary of the Invention

[0005] Technical issues

[0006] The purpose of this disclosure is to provide improved host materials capable of providing organic electroluminescent devices with improved driving voltage, luminous efficiency, and / or lifetime characteristics. Another purpose of this disclosure is to provide an organic electroluminescent device that, through specific combinations comprising the compounds of this disclosure, exhibits improved driving voltage, luminous efficiency, and / or lifetime characteristics.

[0007] Solution to the problem

[0008] As a result of in-depth research into solving the above-mentioned technical problems, the inventors of this invention have discovered that the above-mentioned objective can be achieved by a variety of main materials, which include a first main material and a second main material. The first main material includes a compound represented by Formula 1, and the second main material includes a compound represented by Formula 2.

[0009]

[0010] In Equation 1,

[0011] It is a structure in which five to eight rings selected from the group consisting of substituted or unsubstituted (C6-C30) aromatic rings and substituted or unsubstituted (3-membered to 30-membered) heteroaromatic rings are fused around a heptagonal or octagonal ring, and the structure contains at least one nitrogen-containing pentagonal ring.

[0012] L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group;

[0013] Ar represents deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 11 R 12 or -SiR 13 R 14 R 15 ;and

[0014] R 11 To R 15 Each can be independently represented as a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl.

[0015]

[0016] In Equation 2,

[0017] X' represents O, S, or CR5R6;

[0018] R1 to R4 independently represent hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -L3-NR 16 R 17 or -SiR 18 R 19 R 20 Alternatively, it can connect with one or more adjacent substituents to form one or more rings;

[0019] Wherein, at least one of R1 to R4 represents a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or -L3-NR. 16 R 17 or -SiR 18 R 19 R 20 ;

[0020] L3 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0021] R5 and R6 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or R5 and R6 may be connected to each other to form one or more rings;

[0022] R 16 To R 20 Each of these terms independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group; and

[0023] a' and d' each independently represent an integer from 1 to 4, b' and c' each independently represent an integer of 1 or 2, and each R1 to each R4 can be the same or different from each other if each of a' to d' is an integer of 2 or greater.

[0024] Beneficial effects of the present invention

[0025] Compared with conventional organic electroluminescent devices, organic electroluminescent devices with low driving voltage, high luminous efficiency and / or excellent lifetime characteristics are provided by including specific combinations of compounds according to the present disclosure as a variety of host materials, and can be used to produce display systems or lighting systems. Detailed Implementation

[0026] This disclosure will be described in detail below. However, the following description is intended to explain this disclosure and is not intended to limit the scope of this disclosure in any way.

[0027] The term "organic electroluminescent compound" in this disclosure refers to a compound that can be used in an organic electroluminescent device and can be included, as needed, in any layer constituting the organic electroluminescent device.

[0028] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. As needed, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (comprising a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0029] The term "multiple host materials" in this disclosure refers to a host material comprising a combination of at least two compounds, which may be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both materials included before (e.g., before vapor deposition) and materials included after (e.g., after vapor deposition) the organic electroluminescent device. As an embodiment, the multiple host materials of this disclosure may be a combination of at least two host materials, and may optionally further include one or more conventional materials included in the organic electroluminescent device. The at least two compounds included in the multiple host materials of this disclosure may be included together in a single light-emitting layer, or may be included separately in different light-emitting layers. For example, the at least two host materials may be mixed and evaporated or co-evaporated, or may be evaporated individually.

[0030] In this document, the terms "(C1-C30)alkyl" or "(C1-C30)alkylene" refer to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30)cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. The term "(3- to 7-membered) heterocyclic alkyl" refers to a cycloalkyl group having 3 to 7 cyclic skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably from the group consisting of O, S, and N. The aforementioned heterocyclic alkyl group can include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The terms "(C6-C30) aryl," "(C6-C30) arylene," or "(C6-C30) aromatic hydrocarbon" refer to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 cyclic skeleton carbon atoms. The aforementioned aryl group can be partially saturated and can contain a spirostructure. The aforementioned aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, phenylphenanthrene, benzo[a]phenanthrene, anthracene, indene, triphenylene, pyrene, tetraphenyl, floryl, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, spiro[fluorene-benzo[fluorene]yl], spiro[cyclopenten-fluoren]yl, spiro[dihydroindene-fluoren]yl, azulenyl, tetramethyldihydrophenanthrene, etc. Specifically, the above-mentioned aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzo[anthrayl], 1-phenanthrene, 2-phenanthrene, 3-phenanthrene, 4-phenanthrene, 9-phenanthrene, tetraphenyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Benzophenanthryl, 2-Benzophenanthryl, 3-Benzophenanthryl, 4-Benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzo[a]fluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl Phenyl-3-yl, m-triphenyl-2-yl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, m-tetraphenyl, 3-fluoranthyl, 4-fluoranthyl, 8-fluoranthyl, 9-fluoranthyl, benzofluoranthyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4”-tert-butyl-p-triphenyl-4-yl, 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, 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-benzene [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 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-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 -8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl ]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-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthyl, etc.

[0031] The terms "(3- to 30-membered) heteroaryl", "(3- to 30-membered) heteroaryl", or "(3- to 30-membered) heteroaromatic hydrocarbon" refer to an aryl or aryl group having 3 to 30 ring skeleton atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The aforementioned heteroaryl or aryl group may be a monocyclic ring or a fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a heteroaryl or aryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and it may contain a spirostructure. The aforementioned heteroaryl groups can include monocyclic heteroaryl groups, such as furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazonyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and fused-ring heteroaryl groups, such as benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, and dibenzothiopheneyl. Dibenzoselenoyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuran-quinolinyl, benzofuran-quinazolinyl, benzofuran-naphthidyl, benzofuran-pyrimidyl, naphthofuran-pyrimidyl, benzothiophene-quinolinyl, benzothiophene-quinazolinyl, naphthidyl, benzothiophene-naphthidyl, benzothiophene-pyrimidyl, naphthophene-pyrimidyl, pyrimidyl-indolyl, benzopyrimidyl-indolyl, benzofuran-pyrazine Naphthofuranopyrazinyl, benzothiophenopyrazinyl, benzothiophenopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazole, benzocarbazole Dibenzocarbazolyl, phenoxazinyl, phenanthidyl, benzodioxanepentyl, dihydroacridyl, benzotriazolphenazinyl, imidazopyridyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, indocarbazolyl, indocarbazolyl, etc. More specifically, the aforementioned heteroaryl groups may include 1-pyrrole, 2-pyrrole, 3-pyrrole, pyrazinyl, 2-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-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl,7-Imidazolopyridyl, 8-Imidazolopyridyl, 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-furyl 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-Quinolinyl, 3-Quinolinyl, 4- Quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 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-phenanthridyl, 2-phenanthridyl, 3-phenanthridyl, 4-phenanthridyl, 6-phenanthridyl, 7 -Phenyridyl, 8-Phenyridyl, 9-Phenyridyl, 10-Phenyridyl, 1-Acridinel, 2-Acridinel, 3-Acridinel, 4-Acridinel, 9-Acridinel, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrole-1-yl, 2-Methylpyrrole-3- 2-Methylpyrrolo-4-yl, 2-Methylpyrrolo-5-yl, 3-Methylpyrrolo-1-yl, 3-Methylpyrrolo-2-yl, 3-Methylpyrrolo-4-yl, 3-Methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-1-yl, 2-Methyl-1-indolyl, 4-Methyl-1-indolyl, 2-Methyl-3-indolyl, 4-Methyl-3-indolyl, 2-tert-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-dibenzothiophene 4-Dibenzothiophene, 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]-benzofuranyl7-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 [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 1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophene, 2-naphtho-[1,2-b]-benzothiophene 3-Naphtho-[1,2-b]-benzothiophene, 4-Naphtho-[1,2-b]-benzothiophene, 5-Naphtho-[1,2-b]-benzothiophene, 6-Naphtho-[1,2-b]-benzothiophene, 7-Naphtho-[1,2-b]-benzothiophene, 8-Naphtho-[1,2-b]-benzothiophene, 9-Naphtho-[1 [2,b]-benzothiophene, 10-naphtho-[1,2-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene Fenyl, 1-naphtho-[2,1-b]-benzothiophene, 2-naphtho-[2,1-b]-benzothiophene, 3-naphtho-[2,1-b]-benzothiophene, 4-naphtho-[2,1-b]-benzothiophene, 5-naphtho-[2,1-b]-benzothiophene, 6-naphtho-[2,1-b]-benzothiophene, 7-naphtho-[2 [1-b]-benzothiophene, 8-naphtho-[2,1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 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-Benzofurano[3,2-d]pyrimidinyl, 2-Benzofo[3,2-d]pyrimidinyl, 6-Benzofo[3,2-d]pyrimidinyl, 7-Benzofo[3,2-d]pyrimidinyl, 8-Benzofo[3,2-d]pyrimidinyl, 9-Benzofo[3,2-d]pyrimidinyl, 2-Benzofurano[3,2-d]pyrazinyl, 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl Phosphine, 9-benzofurano[3,2-d]pyrazine, 2-benzothio[3,2-d]pyrazine, 6-benzothio[3,2-d]pyrazine, 7-benzothio[3,2-d]pyrazine, 8-benzothio[3,2-d]pyrazine, 9-benzothio[3,2-d]pyrazine, 1-siliconyl, 2-siliconyl, 3-siliconyl, 4-siliconyl, 1-germaniumyl, 2-germaniumyl, 3-germaniumyl, 4-germaniumyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, etc. In addition, "halogens" include F, Cl, Br, and I.

[0032] Furthermore, "ortho (o-)," "meta (m-)," and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that the two substituents are adjacent to each other, and for example, when the two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that the two substituents are at positions 1 and 3, and for example, when the two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that the two substituents are at positions 1 and 4, and for example, when the two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0033] In this document, "substituted" in the phrase "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 the substitution of a hydrogen atom by a group formed by the linkage of two or more of the aforementioned substituents. For example, "a group formed by the linkage of two or more substituents" can be pyridine-triazine. That is, pyridine-triazine can be interpreted as a heteroaryl substituent, or a substituent in which two heteroaryl substituents are linked. In this article, substituted alkyl, substituted alkylene, substituted aryl, substituted arylene, substituted aromatic hydrocarbon, substituted heteroaryl, substituted heteroarylene, substituted heteroaromatic hydrocarbon, substituted cycloalkyl, substituted cycloalkylene, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or dialkylamino, substituted mono- or di-enylamino, substituted mono- or di-arylamino, substituted mono- or di-heteroarylamino, substituted alkylenylamino, One or more substituents of the substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino groups are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocyclic alkyl; ( (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or substituted (3- to 50-membered) heteroaryl group, or substituted with at least one of (C1-C30) alkyl, (C6-C30) aryl, (3- to 50-membered) heteroaryl, and di(C6-C30) arylamino; unsubstituted or substituted (C6-C30) aryl group, or substituted with at least one of deuterium, cyano, (C1-C30) alkyl, (3- to 50-membered) heteroaryl, mono- or di-(C6-C30) arylamino, and tri(C6-C30) arylsilyl; tri(C1-C30) alkylsilyl; tri(C6-C 30) Arylsilyl; Di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; Mono- or Di-(C1-C30)alkylamino; Mono- or Di-(C2-C30)alkenylamino; Mono- or Di-(C6-C30)arylamino; Mono- or Di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (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; di(C6-C30)arylboroncarbonyl; di(C1-C30)alkylboroncarbonyl; (C1-C30)alkyl(C6-C30)arylboroncarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, each of the one or more substituents is independently selected from at least one of the following groups: deuterium; cyano; (C1-C20) alkyl; unsubstituted or substituted with at least one of deuterium, cyano, (C1-C20) alkyl and (5- to 30-membered) heteroaryl; and unsubstituted or substituted with at least one of (C6- to 30-membered) heteroaryl. According to another embodiment of this disclosure, the one or more substituents are each independently selected from at least one of the following groups: deuterium; cyano; (C1-C10)alkyl; unsubstituted (C6-C18)aryl or substituted with at least one of deuterium, cyano, (C1-C10)alkyl and (5- to 26-membered) heteroaryl; and unsubstituted (5- to 26-membered) heteroaryl or substituted with at least one of (C6-C18)aryl and (5- to 26-membered) heteroaryl. For example, the one or more substituents may be at least one selected from the group consisting of: deuterium; cyano; methyl; an unsubstituted phenyl group or substituted with at least one of deuterium, cyano, and (26-membered) heteroaryl; naphthyl, biphenyl; naphthylphenyl; phenylnaphthyl; phenanthrene; dimethylfluorenyl; dimethylbenzofluorenyl; spirodifluorenyl; terphenyl; benzophenanthrene; an unsubstituted pyridyl group or substituted with one or more phenyl groups; pyrimidinyl; triazine group substituted with at least one of phenyl, naphthyl, biphenyl, and pyrimidinyl; dibenzofuranyl; dibenzothiopheneyl; benzonaphthiopheneyl; an unsubstituted carbazole group or substituted with one or more phenyl groups; an unsubstituted benzocarbazole group or substituted with one or more phenyl groups; dibenzocarbazole; (26-membered) heteroaryl; and diphenylamino.

[0034] In this document, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected or fused together to form a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic ring, or a combination thereof. Preferably, the ring can be a substituted or unsubstituted monocyclic or polycyclic (3-membered to 26-membered) alicyclic or aromatic ring, or a combination thereof. More preferably, the ring can be an unsubstituted monocyclic or polycyclic (5-membered to 25-membered) aromatic ring substituted with at least one of (C1-C6) alkyl, (C6-C18) aryl, and (3-membered to 20-membered) heteroaryl. Furthermore, 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. For example, the ring can be a benzene ring, a cyclopentane ring, an indene ring, an indene ring, a fluorene ring, a phenanthrene ring, an indole ring, a benzofuran ring, an oxane ring, etc., wherein the ring may be substituted with at least one methyl group.

[0035] In this disclosure, the heteroaryl, heteroaryl and heterocycloalkyl groups may each independently contain at least one heteroatom selected from B, N, O, S, Si and P. Furthermore, the heteroatom may bond to at least one of the following groups: 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, substituted or unsubstituted mono- or di-(C1-C30)alkyl Amino, substituted or unsubstituted mono- or di-(C2-C30)-alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)-arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30)-alkyl(C2-C30)-alkenylamino, substituted or unsubstituted (C1-C30)-alkyl(C6-C30)-arylamino, substituted or unsubstituted (C1-C30)-alkyl(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)-alkenyl(C6-C30)-arylamino, substituted or unsubstituted (C2-C30)-alkenyl(3- to 30-membered) heteroarylamino, and substituted or unsubstituted (C6-C30)-aryl(3- to 30-membered) heteroarylamino.

[0036] The various host materials disclosed herein comprise one or more first host materials and one or more second host materials, wherein the one or more first host materials comprise at least one compound represented by Formula 1, and the one or more second host materials comprise at least one compound represented by Formula 2. According to one embodiment of the present disclosure, the compound represented by Formula 1 is different from the compound represented by Formula 2.

[0037] In Formula 1, L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C3-C30) cycloalkylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of this disclosure, L represents a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 20-membered) heteroarylene. According to another embodiment of this disclosure, L represents a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 20-membered) heteroarylene substituted with one or more (C6-C18) arylene groups. For example, L can be a single bond, phenylene, naphthylene, biphenylene, pyridylene, pyrimidinylene, triazinylene, quinolinylene, quinazolinylene, quinoxalinylene, naphthinylene, carbazolyl, dibenzofuranylene, benzofuranopyrimidinylene, benzothiophenopyrimidinylene, pyrimidindoleylene, benzoquinazolinylene, benzoquinoxalinylene, phenylquinoxalinylene, phenylquinoxalinylene, etc.

[0038] In Formula 1, Ar represents deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 11 R 12 or -SiR 13 R 14 R 15 According to one embodiment of this disclosure, Ar represents a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5- to 20-membered) heteroaryl, or -NR. 11 R 12 According to another embodiment of this disclosure, Ar represents an unsubstituted (C6-C25) aryl group or one or more (C1-C6) alkyl groups substituted with an unsubstituted (5- to 20-membered) heteroaryl group or one or more (C6-C18) aryl groups substituted with at least one of deuterium, (C1-C6) alkyl, (C6-C18) aryl, and (5- to 26-membered) heteroaryl groups; or -NR 11 R 12. For example, Ar can be an unsubstituted phenyl, a phenyl substituted with at least one deuterium, a phenyl substituted with one or more (26-membered) heteroaryl groups, naphthyl, biphenyl, a fluorenyl substituted with one or more methyl groups, a benzo[fluorenyl] substituted with one or more methyl groups, spirodifluorenyl, terphenyl, triphenylene, an unsubstituted or substituted pyridyl group, a pyrimidinyl group substituted with one or more phenyl groups, a substituted triazine group, a substituted quinoxalinyl group, a substituted quinoxalinyl group, a quinoxalinyl group substituted with one or more phenyl groups, a naphthidyl group substituted with one or more phenyl groups, a benzo[quinoxalinyl] substituted with one or more phenyl groups, a benzo[quinoxalinyl] substituted with one or more phenyl groups, an unsubstituted or substituted carbazolyl group, an unsubstituted or substituted dibenzofuranyl group, an unsubstituted or substituted dibenzothiophenyl group, a benzo[furanopyrimidinyl group substituted with one or more phenyl groups, a benzo[thiophenopyrimidinyl group substituted with one or more phenyl groups, a pyrimidindolyl group substituted with one or more phenyl groups, or -NR. 11 R 12 At least one of the following. One or more of the substituted triazine, substituted quinoxalin, and substituted quinazolinyl groups are each independently unsubstituted or substituted with at least one of deuterium and (26-membered) heteroaryl groups, namely phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, pyridyl substituted with one or more phenyl groups, dibenzofuranyl, and dibenzothiophene.

[0039] R 11 To R 15 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl. According to one embodiment of this disclosure, R 11 To R 15 Each independently represents a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, R 11 To R 15 Each independently represents an unsubstituted (C6-C18) aryl group or a (C1-C6) substituted (C6-C18) alkyl group, or an unsubstituted (5- to 20-membered) heteroaryl group or a (C6-C18) substituted (C6-C18) aryl group. For example, R 11 To R 15 Each can be phenyl, naphthyl, biphenyl, or dimethylfluorenyl, etc.

[0040] In Equation 1, The structure comprises 5 to 8 rings selected from the group consisting of substituted or unsubstituted (C6-C30) aromatic rings and substituted or unsubstituted (3- to 30-membered) heteroaromatic rings fused around a heptagonal or octagonal ring, and the structure includes at least one nitrogen-containing pentagonal ring. * indicates the binding position with L. According to one embodiment of this disclosure, It can be represented by any one of the following equations 1-1 to 1-3:

[0041]

[0042] In equations 1-1 to 1-3, X1 to X 37 Each can be independently represented as -N = or -C(R) a According to one embodiment of this disclosure, X1 to X... 37 Each is independently represented as -C(R) a = ).

[0043] R a Each of these elements 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, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- Or di-(C2-C30)-enylamino, substituted or unsubstituted mono- or di-(C6-C30)-arylamino, substituted or unsubstituted mono- or di-(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30)-alkyl(C2-C30)-enylamino, substituted or unsubstituted (C1-C30)-alkyl(C6-C30)-arylamino, substituted or unsubstituted (C1-C30)-alkyl(3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30)-enyl(3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30)-aryl(3- to 30-membered) heteroarylamino, or adjacent R a They can be connected to each other to form one or more loops, and if there are multiple R... a Then each R a They can be the same as or different from each other. According to one embodiment of this disclosure, R... aEach independently represents hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-membered to 25-membered) heteroaryl, or adjacent R a They can be linked together to form one or more substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic or aromatic rings, or combinations thereof. According to another embodiment of this disclosure, R a Each independently represents hydrogen, an unsubstituted (C6-C18) aryl group, or an unsubstituted (5- to 20-membered) heteroaryl group substituted with one or more (C6-C18) aryl groups, or an adjacent R a They can connect with each other to form one or more substituted or unsubstituted monocyclic or polycyclic (5-membered to 20-membered) alicyclic or aromatic rings, or combinations thereof. For example, R a Each can be independently hydrogen, phenyl, naphthyl, or a triazine group substituted with one or more phenyl groups, or an adjacent R a They can connect with each other to form one or more benzene rings, one or more benzofuran rings, or one or more indene rings substituted with one or more methyl groups.

[0044] In equations 1-3, Y1 represents -N(L′1-(Ar′1)). n -, -O-, -S-, or -C(R) b (R) c )-.

[0045] L′1 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group. For example, L′1 can be a single bond.

[0046] Ar′1 represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a -N(R) group. d (R) e According to one embodiment of this disclosure, Ar′1 represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, Ar′1 represents an unsubstituted or deuterated (C6-C18) aryl group, or an unsubstituted (5-membered to 20-membered) heteroaryl group. For example, Ar′1 may be an unsubstituted or deuterated phenyl, biphenyl, or pyridyl group.

[0047] R b To R eEach can 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, or substituted or unsubstituted (C3-C30) cycloalkyl, or can be linked with one or more adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R b To R e Each can independently represent a substituted or unsubstituted (C1-C10) alkyl group. For example, R b To R e Each can be a methyl group independently.

[0048] n represents an integer of 1 or 2, and if n is an integer of 2, then each Ar′1 can be the same as or different from each other.

[0049] Equation 1-1 can be represented by the following equation 1-1-1:

[0050]

[0051] In equation 1-1-1,

[0052] R 31 To R 33 Each independently with R a The definitions are the same; and

[0053] aa represents integers from 1 to 5, ab represents integers from 1 to 4, and ac represents integers from 1 to 3, where if each of aa, ab, and ac is an integer of 2 or greater, then each R... 31 Each R 32 and each R 33 They can be the same as or different from each other.

[0054] Equation 1-2 can be expressed by the following equation 1-2-1:

[0055]

[0056] In Equation 1-2-1,

[0057] R 41 To R 44 Each independently with R a The definitions are the same; and

[0058] ba represents an integer of 1 or 2, bb and bc each independently represent integers from 1 to 4, bd represents integers from 1 to 3, and where if each of ba, bb, bc, and bd is an integer of 2 or greater, then each R 41 Each R 42 Each R 43 and each R44 They can be the same as or different from each other.

[0059] Equation 1-3 can be represented by the following equation 1-3-1:

[0060]

[0061] In Equation 1-3-1,

[0062] R 51 To R 54 Each independently with R a The definitions are the same;

[0063] ca represents an integer of 1 or 2, cb and cd each independently represent integers from 1 to 3, cc represents integers from 1 to 4, and where if each of ca, cb, cc, and cd is an integer of 2 or greater, then each R 51 Each R 52 Each R 53 and each R 54 They can be the same as or different from each other; and

[0064] L′1 and Ar′1 are the same as those defined in Equation 1-3.

[0065] In Equation 2, X' represents O, S, or CR5R6.

[0066] R5 and R6 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, or R5 and R6 may be linked together to form one or more rings. According to one embodiment of this disclosure, R5 and R6 each independently represent a substituted or unsubstituted (C1-C10) alkyl. According to another embodiment of this disclosure, R5 and R6 each independently represent an unsubstituted (C1-C6) alkyl. For example, R5 and R6 may each independently be methyl.

[0067] In Formula 2, R1 to R4 each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -L3-NR 16 R 17 or -SiR 18 R 19 R 20Alternatively, it can be linked with one or more adjacent substituents to form one or more rings. According to one embodiment of this disclosure, R1 to R4 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-membered to 25-membered) heteroaryl, or -L3-NR. 16 R 17 Alternatively, it can be linked with one or more adjacent substituents to form one or more rings. According to another embodiment of this disclosure, R1 to R4 each independently represent hydrogen; deuterium; an unsubstituted (C6-C18) aryl group or substituted with one or more (3- to 30-membered) heteroaryl groups; an unsubstituted (5- to 20-membered) heteroaryl group or substituted with at least one of cyano, (C6- to 18-membered) aryl, and (5- to 20-membered) heteroaryl groups; or -L3-NR 16 R 17 Alternatively, it can be linked with one or more adjacent substituents to form one or more rings.

[0068] Here, at least one of R1 to R4 represents a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or -L3-NR. 16 R 17 or -SiR 18 R 19 R 20 According to one embodiment of this disclosure, at least one of R1 to R4 may represent an unsubstituted (C6-C30) aryl group or a (C6-C30) aryl group substituted with one or more (C6-C30) heteroaryl groups, a substituted or unsubstituted (C6-C30) heteroaryl group, or a -L3-NR group. 16 R 17 According to another embodiment of this disclosure, at least one of R1 to R4 may represent an unsubstituted (C6-C18) aryl group or a (C6-C18) aryl group substituted with one or more (5- to 25-membered) heteroaryl groups, or an unsubstituted (C6- to 20-membered) heteroaryl group substituted with at least one of cyano, (C6- to 20-membered) aryl, and (C6- to 20-membered) heteroaryl groups; or -L3-NR 16 R 17 According to one embodiment of this disclosure, at least one of R1 to R4 represents -L2-HAr or -L3-NR. 16 R 17 .

[0069] L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of this disclosure, L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene. According to another embodiment of this disclosure, L2 and L3 each independently represent a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 20-membered) heteroarylene. For example, L2 and L3 can each independently be a single bond, a phenylene, a naphthylene, a biphenylene, or a pyridylene.

[0070] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of N, O, and S. According to one embodiment of this disclosure, HAr represents an unsubstituted or (5- to 25-membered) heteroaryl group containing at least one of N, O, and S, or substituted with one or more (C6-C30) aryl groups. According to another embodiment of this disclosure, HAr represents an N-containing (5- to 25-membered) heteroaryl group substituted with one or more (C6-C25) aryl groups. For example, HAr can be a substituted pyrimidinyl group, a substituted triazine group, a quinoxalinyl group substituted with one or more naphthyl groups, a quinazolinyl group substituted with one or more biphenyl groups, or a benzofuranopyrimidinyl group substituted with one or more phenyl groups, wherein the one or more substituents of the substituted pyrimidinyl group and the substituted triazine group can each independently be at least one of phenyl, phenyl substituted with one or more cyano groups, naphthyl, biphenyl, phenylnaphthyl, naphthylphenyl, phenanthryl, terphenyl, dimethylfluorenyl, pyrimidinyl, dibenzofuranoyl, and dibenzothiopheneyl.

[0071] R 16 To R 20 Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl. According to one embodiment of this disclosure, R 16 To R 20 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, R 16 To R 20 Each can independently represent an unsubstituted or (C1-C6) alkyl-substituted (C6-C25) aryl group, or an unsubstituted (5-membered to 20-membered) heteroaryl group. For example, R 16 To R 20 Each can be independently phenyl, naphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, phenanthryl, naphthylphenyl, phenylnaphthyl, terphenyl, dibenzofuranyl, or dibenzothiophene.

[0072] In Equation 2, a' and d' each independently represent integers from 1 to 4, b' and c' each independently represent integers of 1 or 2, and each R1 to each R4 can be the same or different from each other if each of a' to d' is an integer of 2 or greater.

[0073] The compound represented by Equation 2 can be represented by any one of Equations 2-1 to 2-4:

[0074]

[0075]

[0076] In equations 2-1 to 2-4,

[0077] X', R1 to R4, and a' to d' are defined as in Equation 2;

[0078] L2 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0079] Z1 to Z3 each independently represent N or CH, provided that at least one of Z1 to Z3 is N;

[0080] Ar2 and Ar3 each independently represent substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0081] e' represents an integer from 1 to 3 independently, and each R1 and each R4 can be the same or different from each other if e' is an integer of 2 or greater.

[0082] According to one embodiment of this disclosure, at least two of Z1 to Z3 are N. According to another embodiment of this disclosure, all of Z1 to Z3 are N.

[0083] According to one embodiment of this disclosure, Ar2 and Ar3 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of this disclosure, Ar2 and Ar3 each independently represent an unsubstituted or substituted (C6-C18) aryl group, or an unsubstituted (5-membered to 20-membered) heteroaryl group, substituted with at least one of a cyano group and a (C1-C6) alkyl group. For example, Ar2 and Ar3 can each independently be an unsubstituted or substituted phenyl, naphthyl, biphenyl, phenylnaphthyl, naphthylphenyl, phenanthryl, terphenyl, dimethylfluorenyl, pyrimidinyl, dibenzofuranyl, or dibenzothiopheneyl group.

[0084] The compound represented by Equation 2 can be represented by any one of Equations 2-5 to 2-8:

[0085]

[0086]

[0087] In equations 2-5 to 2-8,

[0088] X', L3, R1 to R4, R 16 R 17 , and a' to d' are defined as in Equation 2;

[0089] e' represents an integer from 1 to 3 independently, and each R1 and each R4 can be the same or different from each other if e' is an integer of 2 or greater.

[0090] The compound represented by Formula 1 may be at least one selected from the group consisting of, but is not limited to, the following compounds.

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The compound represented by Formula 2 may be at least one selected from the group consisting of, but is not limited to, the following compounds.

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] A combination of at least one of compounds H1-1 to H1-245 and at least one of compounds H2-1 to H2-294 can be used in organic electroluminescent devices.

[0117] The compounds represented by Formulas 1 and 2 according to this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compounds represented by Formula 1 according to this disclosure can be prepared by referring to Korean Patent Application Publication Nos. 2018-0099510 (published September 5, 2018), 2018-0012709 (published February 6, 2018), and 2020-0103524 (published September 2, 2020); and the compounds represented by Formula 2 according to this disclosure can be prepared by referring to reaction schemes 1 to 4 below and Korean Patent Application Publication No. 2017-0043439 (published April 21, 2017), but are not limited thereto.

[0118] [Reaction Scheme 1]

[0119]

[0120] [Reaction Scheme 2]

[0121]

[0122] [Reaction Scheme 3]

[0123]

[0124] [Reaction Scheme 4]

[0125]

[0126] In reaction scheme 4, X' is as defined in equation 2.

[0127] Although illustrative synthetic examples of compounds represented by Formulas 1 and 2 have been described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II) catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, Wittig reactions, Negishi reactions, bromination reactions, and phosphine-mediated reductive cyclization reactions, etc., and that the above reactions are carried out even if substituents defined in Formulas 1 and 2 above but not specified in the specific synthetic examples are bonded.

[0128] This disclosure provides an organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials of this disclosure. A first host material and a second host material may be contained in one light-emitting layer or may be contained in separate light-emitting layers. The ratio of the compound represented by Formula 1 to the compound represented by Formula 2 in the plurality of host materials 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. Furthermore, the compound represented by Formula 1 and the compound represented by Formula 2 can be combined by mixing them in a desired amount in a shaker, by dissolving them in a glass tube by heating, or by dissolving them in a solvent, etc.

[0129] According to one embodiment of this disclosure, the doping concentration of the dopant compound in the light-emitting layer relative to the host compound may be less than about 20 wt%. The dopant included in the organic electroluminescent device of this disclosure may be at least one phosphorescent dopant or fluorescent dopant, and preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but may be a complex compound of metal atoms selected from: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and preferably a complex compound with ortho-metallized metal atoms selected from: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably an ortho-metallized iridium complex compound.

[0130] The dopants included in the organic electroluminescent devices of this disclosure may include, but are not limited to, compounds represented by the following formula 101.

[0131]

[0132] In Equation 101,

[0133] L is selected from the following structures 1 to 3:

[0134]

[0135]

[0136] R 100 To R 103 Each of these can independently represent 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 can be linked with one or more adjacent substituents to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indoquinoline;

[0137] R 104 To R 107 Each of these can independently represent 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 can be linked with one or more adjacent substituents to form one or more rings with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuran-pyridine, or substituted or unsubstituted benzothiophene-pyridine;

[0138] R 201 To R 220Each of these groups 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 linked with one or more adjacent substituents to form one or more substituted or unsubstituted rings; and

[0139] s represents an integer from 1 to 3.

[0140] Specific examples of dopant compounds are shown below, but are not limited to.

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] The organic electroluminescent device according to this disclosure has an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of these layers may be further configured as multiple layers.

[0147] The anode and cathode can each be formed from transparent conductive materials, or semi-transparent or reflective conductive materials. Depending on the materials used to form the anode and cathode, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type. Furthermore, the hole injection layer can be further doped with p-type dopant, and the electron injection layer can be further doped with n-type dopant.

[0148] The organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0149] Furthermore, in the organic electroluminescent device disclosed herein, the organic layer may further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, organometals of lanthanides and d-transition elements, or at least one complex compound comprising said metal.

[0150] Furthermore, the organic electroluminescent device of this disclosure can emit white light by further comprising at least one light-emitting layer, which, in addition to the compounds disclosed herein, also comprises blue, red, or green electroluminescent compounds known in the art. If desired, it may further comprise a yellow or orange light-emitting layer.

[0151] In the organic electroluminescent device of this disclosure, preferably, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") can be placed on one or more inner surfaces of one or two electrodes. Specifically, it is preferred to place silicon and aluminum chalcogenide (including oxide) layers on the anode surface of the electroluminescent dielectric layer, and preferably to place the metal halide layer or metal oxide layer on the cathode surface of the electroluminescent dielectric layer. This surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO2. X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0152] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting 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 each of the multilayers can use two compounds simultaneously. The hole transport layer or electron blocking layer can also be multilayered.

[0153] 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, wherein each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each of the multilayers can use multiple compounds.

[0154] A light-emitting auxiliary layer can be 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, it can be used to promote hole injection and / or hole transport, or to prevent electron leakage. When placed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport, or to prevent hole leakage. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling charge balance control. Additionally, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine excitons within the light-emitting layer by blocking electron leakage from the light-emitting layer to prevent light leakage. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0155] Furthermore, preferably, in the organic electroluminescent device of this disclosure, a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and 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 anion, and thus it becomes easier to inject and transport electrons from the mixed region into the light-emitting medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the light-emitting medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds; and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0156] The organic electroluminescent compounds or materials according to this disclosure can be used as luminescent materials for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting devices, such as side-by-side or stacked structures, depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) luminescent components, or color conversion material (CCM) methods, etc. The organic electroluminescent materials according to this disclosure can also be used in organic electroluminescent devices incorporating quantum dots (QDs).

[0157] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used. When the first and second host compounds of this disclosure are used to form the film, a co-evaporation process or a mixed evaporation process is performed.

[0158] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no problems with film-forming ability.

[0159] Furthermore, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be produced using the organic electroluminescent devices disclosed herein; or lighting systems, such as outdoor or indoor lighting systems.

[0160] In the following sections, the preparation methods of the compounds according to this disclosure and the properties of the compounds will be explained in detail with reference to representative compounds of this disclosure. However, this disclosure is not limited to the following examples.

[0161] [Example 1] Preparation of compound H1-1

[0162]

[0163] Compound 5 (5 g, 17.16 mmol), 4-bromo-1,1′:2′,1″-terphenyl (5.3 g, 17.16 mmol), Pd2(dba)3 (0.8 g, 0.858 mmol), Sphos (0.7 g, 1.716 mmol), NaOt-Bu (5 g, 51.48 mmol), and 86 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in CHCl3, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-1 (2.4 g, yield: 26%).

[0164] 1H NMR (DMSO-d6) δ: 7.92-7.88 (m, 1H), 7.87-7.83 (m, 1H), 7.79 (d, J=9.1Hz, 1H), 7.74 (t, J=8.3Hz, 2H), 7.59-7.54 (m, 2H), 7.53-7.49 (m, 2H), 7.48 -7.41(m, 6H), 7.38(d, J=2.3Hz, 1H), 7.36(d, J=2.1Hz, 2H), 7.34-7.31( m, 2H), 7.30-7.25 (m, 2H), 7.21-7.17 (m, 2H), 7.12 (dd, J=8.1, 0.6Hz, 1H)

[0165] [Example 2] Preparation of compound H1-122

[0166]

[0167] Compound 5 (5 g, 17.16 mmol), 1-(3-bromophenyl)dibenzo[b,d]thiophene (7 g, 20.59 mmol), CuI (0.16 g, 0.858 mmol), ethylenediamine (EDA) (1 g, 17.16 mmol), K3PO4 (9.1 g, 42.90 mmol), and 90 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The filtered solid was dissolved in CHCl3, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-122 (2.2 g, yield: 22%).

[0168] 1 H NMR (DMSO-d6) δ: 8.09 (dd, J=8.0, 1.1Hz, 1H), 8.04 (ddd, J=8.0, 1.1, 0.7Hz, 1H), 7.92-7.87 (m, 2H), 7.85-7.82 (m, 1H), 7.80 (ddd, J=8.0, 2.1, 1.2Hz, 1H), 7.78-7.71(m, 3H), 7.68-7.63(m, 2H), 7.60-7.52(m, 3H), 7.48-7.38(m, 5H), 7.36-7.24(m, 4H)

[0169] [Example 3] Preparation of compound H1-16

[0170]

[0171] In a flask, 70 mL of toluene was added dropwise to compound 5 (4.0 g, 14 mmol), 9-(3-bromophenyl)-9H-carbazole (4.87 g, 15 mmol), CuI (1.307 g, 7 mmol), EDA (1.647 g, 27 mmol), and K3PO4 (5.83 g, 27 mmol), and the mixture was then stirred under reflux at 180 °C for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, dried over magnesium sulfate, and then separated by column chromatography. Subsequently, methanol was added to the residue, and the resulting solid was filtered under reduced pressure to obtain compound H1-16 (2.3 g, yield: 31.5%).

[0172] 1 H NMR (600MHz, DMSO-d6, δ) 8.27 (d, J=7.8Hz, 2H), 8.01 (t, J=8.0Hz, 1H), 7.95-7.92 (m, 1H), 7.91-7.84 (m, 4H), 7.83 (d, J=6.9H z, 1H), 7.81-7.77 (m, 2H), 7.66 (d, J=8.9Hz, 1H), 7.63-7.57 (m, 3H), 7.51-7.44 (m, 5H), 7.44-7.40 (m, 2H), 7.35-7.30 (m, 2H)

[0173] [Example 4] Preparation of compound H1-120

[0174]

[0175] 1) Synthesis of compound S2

[0176] Compound S1 (36 g, 125.38 mmol), 3-bromo-2-chloronitrobenzene (27 g, 113.98 mmol), tetrakis(triphenylphosphine)palladium (4 g, 3.42 mmol), sodium carbonate (30 g, 285.95 mmol), 570 mL of toluene, 140 mL of ethanol, and 140 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 120 °C under reflux for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound S2 (30 g, yield: 66%).

[0177] 2) Synthesis of compound S3

[0178] Compound S2 (27 g, 68.20 mmol), palladium(II) acetate (1.5 g, 6.82 mmol), tricyclohexylphosphine tetrafluoroborate (5.0 g, 13.64 mmol), cesium carbonate (66 g, 204.60 mmol), and 340 mL of o-xylene were added to a reaction vessel, and the mixture was stirred under reflux for 2 hours. After the reaction was complete, the mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound S3 (24.8 g, yield: 100%).

[0179] 3) Synthesis of compound S4

[0180] Compound S3 (24.8 g, 68.20 mmol), triethyl phosphite (176 mL, 0.4 M), and 341 mL of 1,2-dichlorobenzene (DCB) were added to a reaction vessel, and the mixture was stirred at 200 °C for 4 hours. After the reaction was complete, the mixture was distilled under reduced pressure to remove triethyl phosphite. The product was then washed with distilled water, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound S4 (16.4 g, yield: 70%).

[0181] 4) Synthesis of compound H1-120

[0182] Compound S4 (5.0 g, 15.2 mmol), 4-bromo-N,N-di-phenylaniline (5.4 g, 16.7 mmol), Pd2(dba)3 (0.7 g, 0.76 mmol), Sphos (0.6 g, 1.52 mmol), NaOtBu (2.9 g, 30.4 mmol), and 80 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred at room temperature. Subsequently, the solid formed by the addition of MeOH was filtered under reduced pressure, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-120 (4.0 g, yield: 46%).

[0183] compound MW MP H1-120 573.7 317℃

[0184] [Example 5] Preparation of compound H1-121

[0185]

[0186] Compound 6 (14.0 g, 31.4 mmol), N-phenyl-[1,1′-biphenyl]-3-amine (7.78 g, 31.7 mmol), Pd2(dba)3 (1.44 g, 1.57 mmol), t-Bu3P (635 mg, 3.14 mmol), and t-BuONa (6.04 g, 62.8 mmol) and 160 mL of toluene were added to a flask, dissolved, and then stirred under reflux for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was distilled under reduced pressure, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-121 (14.6 g, yield: 76%).

[0187] compound MW MP H1-121 610.7 141℃

[0188] [Example 6] Preparation of compound H1-119

[0189]

[0190] Compound 5 (10 g, 34.3 mmol), 3-bromodibenzo[b,d]furan (12.7 g, 51.45 mmol), CuI (3.3 g, 17.15 mmol), ethylenediamine (EDA) (4.6 mL, 68.8 mmol), K3PO4 (21.8 g, 102.9 mmol), and 170 mL of toluene were added to a flask, dissolved, and then stirred under reflux for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred at room temperature. Subsequently, the solid formed by the addition of MeOH was filtered under reduced pressure, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-119 (8.3 g, yield: 53%).

[0191] compound MW MP H1-119 457.53 255.4℃

[0192] [Example 7] Preparation of compound H1-12

[0193]

[0194] 1) Synthesis of compound 12-1

[0195] Compound 5 (10.0 g, 34.3 mmol), 1-bromo-4-iodobenzene (14.6 g, 51.5 mmol), CuI (3.28 g, 17.2 mmol), EDA (4.12 g, 68.6 mmol), K3PO4 (14.6 g, 68.6 mmol), and 170 mL of toluene were added to a flask, and the mixture was stirred under reflux at 145 °C for 3 hours. After the reaction was complete, the solid was extracted with MC, dried over MgSO4, and separated by column chromatography. Subsequently, MeOH was added to the residue, and the resulting solid was filtered under reduced pressure to obtain compound H12-1 (9.0 g, yield: 59%).

[0196] 2) Synthesis of compound H1-12

[0197] Compound 12-1 (5.0 g, 11 mmol), N-phenyl-[1,1′-biphenyl]-4-amine (3.3 g, 13 mmol), Pd2(dba)3 (0.513 g, 0.56 mmol), Sphos (0.460 g, 1 mmol), NaOt-Bu (2.691 g, 28 mmol), and 60 mL of toluene were added to a flask, and the mixture was stirred under reflux at 100 °C for half an hour. After the reaction was complete, the solid was extracted with MC, dried over MgSO4, and then separated by column chromatography. Subsequently, MeOH was added to the residue, and the resulting solid was filtered under reduced pressure to obtain compound H1-12 (1.3 g, yield: 19%).

[0198] compound MW MP H1-12 610.76 168℃

[0199] [Example 8] Preparation of compound H1-35

[0200]

[0201] 14H-7b,14-diazadibenzo[3,4:5,6]azolo[7,8,1-lma]fluorene (5.0 g, 15.1 mmol), 2-bromodibenzo[b,d]furan (4.1 g, 16.6 mmol), Pd2(dba)3 (0.691 g, 0.755 mmol), Sphos (0.620 g, 1.51 mmol), NaOtBu (3.63 g, 37.8 mmol), and 75 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred. The solid formed by the addition of MeOH was filtered under reduced pressure, extracted with MC / Hex, and separated by column chromatography to obtain compound H1-35 (1.9 g, yield: 25%).

[0202] compound MW MP H1-35 496.56 280℃

[0203] [Example 9] Preparation of compound H1-36

[0204]

[0205] 14H-7b,14-diazadibenzo[3,4:5,6]azolo[7,8,1-lma]fluorene (5.0 g, 15.1 mmol), 3-bromo-N,N-diphenylaniline (5.4 g, 16.6 mmol), Pd2(dba)3 (0.693 g, 0.757 mmol), Sphos (0.621 g, 1.51 mmol), NaOt-Bu (3.64 g, 37.8 mmol), and 60 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux at 190 °C for one hour. After the reaction was complete, the mixture was cooled to room temperature and separated through a silica filter to obtain compound H1-36 (6.3 g, yield: 72.6%).

[0206] compound MW MP color H1-36 573.70 230.4℃ green yellow

[0207] [Example 10] Preparation of compound H1-14

[0208]

[0209] Compound 1 (5 g, 15.13 mmol), compound 2 (4 g, 15.13 mmol), Pd2(dba)3 (0.7 g, 0.756 mmol), NaOt-Bu (4.3 g, 45.40 mmol), s-phos (0.6 g, 1.513 mmol), and 75 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 1 hour and 20 minutes. After the reaction was complete, the mixture was cooled to room temperature and methanol was added dropwise. Subsequently, the mixture was filtered, dissolved in MC, and separated by column chromatography to obtain compound H1-14 (3.1 g, yield: 36%).

[0210] compound MW MP H1-14 538.7 245.2℃

[0211] [Example 11] Preparation of compound H2-9

[0212]

[0213] Compound 2 (5.0 g, 12.7 mmol), compound 3 (5.5 g, 15.3 mmol), K₂CO₃ (3.5 g, 25.4 mmol), and Pd(PPh₃)₄ (0.73 g, 0.63 mmol) were added to a flask, dissolved in 39 mL of toluene, 10 mL of ethanol, and 13 mL of water, and then stirred under reflux at 130 °C for 6 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, the residual water was dried over magnesium sulfate, and the residue was separated by column chromatography to obtain compound H₂-9 (4.4 g, yield: 20%).

[0214] compound MW MP H2-9 589.65 318℃

[0215] [Example 12] Preparation of compound H2-2

[0216]

[0217] Compound 2 (5.0 g, 12.7 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (4.8 g, 15.2 mmol), K₂CO₃ (3.5 g, 25.4 mmol), and Pd(PPh₃)₄ (0.73 g, 0.63 mmol) were added to a flask, dissolved in 39 mL of toluene, 10 mL of ethanol, and 13 mL of water, and then stirred under reflux at 130 °C for 6 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, the residual water was dried over magnesium sulfate, and the residue was separated by column chromatography to obtain compound H₂-2 (4.4 g, yield: 20%).

[0218] compound MW MP H2-2 549.62 229℃

[0219] [Example 13] Preparation of compound H2-191

[0220]

[0221] 1) Synthesis of compound 4

[0222] 1-Bromo-3-chlorodibenzo[b,d]furan (39.2 g, 139.3 mmol), (2-formylphenyl)boronic acid (52.2 g, 348.1 mmol), tetrakis(triphenylphosphine)palladium(0) (16.1 g, 13.9 mmol), Cs₂CO₃ (136.1 g, 418 mmol), 840 mL of toluene, 160 mL of ethanol, and 210 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 140 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by rotary evaporator. The residue was then purified by column chromatography to obtain compound 4 (32.1 g, yield: 75%).

[0223] 2) Synthesis of Compound 5

[0224] Compound 4 (31.6 g, 103 mmol), (methoxymethyl)triphenylphosphine chloride (45.9 g, 133.9 mmol), and 515 mL of tetrahydrofuran were added, and the reaction mixture was stirred for 10 minutes. Subsequently, potassium tert-butoxide (1 M, 150 mL in THF) was slowly added dropwise at 0 °C. The temperature was slowly increased, and the mixture was stirred at room temperature for 3 hours. After the reaction was complete by adding distilled water, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 5 (31.2 g, yield: 90%).

[0225] 3) Synthesis of Compound 6

[0226] Compound 5 (29.8 g, 89.0 mmol), 22.4 mL of boron trifluoride ether, and 890 mL of dichloromethane (MC) were added to a reaction vessel, and the mixture was stirred for 3 hours. After the reaction was complete, the organic layer was extracted with dichloromethane (MC) and water. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 6 (24.2 g, yield: 90%).

[0227] 4) Synthesis of Compound 7

[0228] Compound 6 (18.0 g, 59.5 mmol), bis(pinacol)diboron (19.7 g, 77.3 mmol), tris(dibenzylacetone)dipalladium(0) (2.8 g, 2.9 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (2.4 g, 5.9 mmol), potassium acetate (17.5 g, 178.5 mmol), and 300 mL of 1,4-dioxane were added to a reaction vessel, and the mixture was stirred at 150 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 7 (1.84 g, yield: 78%).

[0229] 5) Synthesis of compound H2-191

[0230] Compound 7 (4.0 g, 10.1 mmol), compound 8 (3.9 g, 12.2 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.51 mmol), potassium carbonate (2.8 g, 20.2 mmol), 30 mL of toluene, 7 mL of ethanol, and 10 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130 °C for 6 hours. After the reaction was complete, methanol was added dropwise to the mixture, and the resulting solid was filtered and purified by column chromatography to obtain compound H2-191 (4.5 g, yield: 81%).

[0231] compound MW MP H2-191 549.6 228℃

[0232] [Example 14] Preparation of compound H2-192

[0233]

[0234] Compound 7 (4.0 g, 10.1 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (4.4 g, 12.2 mmol), tetra(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol), potassium carbonate (2.8 g, 20.2 mmol), 30 mL of toluene, 7 mL of ethanol, and 10 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130 °C for 6 hours. After the reaction was complete, methanol was added dropwise to the mixture, and the resulting solid was filtered off. The solid was purified by column chromatography to obtain compound H2-192 (3.13 g, yield: 53%).

[0235] compound MW MP H2-192 589.6 250℃

[0236] [Example 15] Preparation of compound H2-229

[0237]

[0238] Compound 6 (4.0 g, 13.2 mmol), N-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine (4.4 g, 13.2 mmol), Pd(OAc)2 (0.15 g, 0.66 mmol), P(tert-Bu)3 (0.65 mL, 1.32 mmol), sodium tert-butoxide (2.5 g, 26.4 mmol), and 66 mL of xylene were added to a reaction vessel, and the mixture was stirred at 165 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by rotary evaporator. The residue was then purified by column chromatography to obtain compound H2-229 (4.9 g, yield: 61%).

[0239] compound MW MP H2-229 601.7 200℃

[0240] [Example 16] Preparation of compound H2-171

[0241]

[0242] 1) Synthesis of compound B

[0243] Compound A (5.0 g, 10.3 mmol), (2-formylphenyl)boronic acid (2.3 g, 15.5 mmol), Pd2(dba)3 (0.47 g, 0.52 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.43 g, 1.03 mmol), K3PO4 (5.5 g, 25.8 mmol), and 52 mL of xylene were added to a reaction vessel, and the mixture was stirred at 165 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound B (4.55 g, yield: 80%).

[0244] 2) Synthesis of compound C

[0245] Compound B (4.55 g, 8.22 mmol), (methoxymethyl)triphenylphosphine chloride (3.66 g, 10.7 mmol), and 41 mL of tetrahydrofuran were added to a reaction vessel, and the reaction mixture was stirred for 10 minutes. Subsequently, 11 mL of potassium tert-butoxide (1 M in THF) was slowly added dropwise at 0 °C. The temperature was slowly increased, and the mixture was stirred at room temperature for 3 hours. After the reaction was complete by adding distilled water, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound C (3.06 g, yield: 64%).

[0246] 3) Synthesis of compound H2-171

[0247] Compound C (2.3 g, 3.95 mmol), Eaton reagent (0.23 mL), and 23 mL of chlorobenzene were added to a reaction vessel, and the mixture was then refluxed for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and the organic layer was extracted with dichloromethane (MC). The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H2-171 (1.93 g, yield: 89%).

[0248] compound MW MP H2-171 549.62 204℃

[0249] [Example 17] Preparation of compound H2-242

[0250]

[0251] 1) Synthesis of compound 9

[0252] 4-Bromo-9,9-dimethyl-9H-fluorene (50 g, 183 mmol), (5-chloro-2-formylphenyl)boronic acid (40.5 g, 219 mmol), tetrakis(triphenylphosphine)palladium(0) (10.6 g, 9.15 mmol), potassium carbonate (63 g, 457 mmol), 690 mL of toluene, 180 mL of ethanol, and 230 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 140 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 9 (40.3 g, yield: 66%).

[0253] 2) Synthesis of Compound 10

[0254] Compound 9 (40.3 g, 121 mmol), (methoxymethyl)triphenylphosphine chloride (53.9 g, 157.4 mmol), and 600 mL of tetrahydrofuran were added to a reaction vessel, and the reaction mixture was stirred for 10 minutes. Subsequently, 162 mL of potassium tert-butoxide (1 M in THF) was slowly added dropwise at 0 °C. The temperature was slowly increased, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed by adding distilled water to the reaction solution, the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The residue was then purified by column chromatography to obtain compound 10 (39 g, yield: 89%).

[0255] 3) Synthesis of Compound 11

[0256] Compound 10 (38 g, 105.3 mmol), 26.5 mL of boron trifluoride ether, and 1000 mL of dichloromethane (MC) were added to a reaction vessel, and the mixture was stirred for 3 hours. After the reaction was complete, the organic layer was extracted with dichloromethane (MC) and water. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 11 (23.2 g, yield: 67%).

[0257] 4) Synthesis of Compound 12

[0258] Compound 11 (19.1 g, 58.1 mmol), bis(pinacol)diboron (19.1 g, 75.5 mmol), tris(dibenzylacetone)dipalladium(O) (2.7 g, 2.9 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (2.4 g, 5.81 mmol), potassium acetate (17.1 g, 174.3 mmol), and 290 mL of 1,4-dioxane were added to a reaction vessel, and the mixture was stirred at 150 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound 12 (12.7 g, yield: 52%).

[0259] 5) Synthesis of compound H2-242

[0260] Compound 12 (4 g, 9.5 mmol), compound 13 (4.1 g, 11.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.48 mmol), potassium carbonate (2.6 g, 19.0 mmol), toluene (30 mL), ethanol (7 mL), and distilled water (10 mL) were added to a reaction vessel, and the mixture was stirred at 130 °C for 6 hours. After the reaction was complete, methanol was added dropwise to the mixture, and the resulting solid was filtered off. The resulting solid was purified by column chromatography to obtain compound H2-242 (4.73 g, yield: 80%).

[0261] compound MW MP H2-242 615.7 237℃

[0262] [Example 18] Preparation of compound H2-241

[0263]

[0264] Compound 12 (5.0 g, 11.9 mmol), 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (4.5 g, 14.3 mmol), tetra(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol), potassium carbonate (3.3 g, 23.8 mmol), 36 mL of toluene, 10 mL of ethanol, and 12 mL of distilled water were added to a reaction vessel, and the mixture was stirred at 130 °C for 6 hours. After the reaction was complete, methanol was added dropwise to the mixture, and the resulting solid was filtered off. The resulting solid was purified by column chromatography to obtain compound H2-241 (3.64 g, yield: 53%).

[0265] compound MW MP H2-241 575.7 209℃

[0266] [Example 19] Preparation of compound H2-57

[0267]

[0268] Compound 14 (5.0 g, 16.5 mmol), compound 15 (5.7 g, 16.5 mmol), Pd(OAc)2 (0.19 g, 0.82 mmol), P(t-Bu)3 (0.82 mL, 1.65 mmol), NaOtBu (3.2 g, 33.0 mmol), and 83 mL of o-xylene were added to a flask, dissolved, and then stirred under reflux for 2 hours. After the reaction was complete, the mixture was extracted with EA / H2O and separated by column chromatography to obtain compound H2-57 (4.46 g, yield: 43%).

[0269] compound MW MP H2-57 615.69 239℃

[0270] [Example 20] Preparation of compound H2-52

[0271]

[0272] Compound 16 (4 g, 10.14 mmol), compound 17 (4.3 g, 10.14 mmol), Pd(PPh3)4 (586 mg, 0.507 mmol), K2CO3 (2.8 g, 20.29 mmol), 50 mL of toluene, 12 mL of EtOH, and 13 mL of H2O were added to a flask, dissolved, and then stirred under reflux at 140 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and the resulting solid was filtered under reduced pressure. The resulting solid was dissolved in CHCl3, separated using a SiO2 filter, and recrystallized from o-xylene and o-dichlorobenzene (o-DCB) to obtain compound H2-52 (5.8 g, yield: 65%).

[0273] compound MW MP H2-52 675.7 270.8℃

[0274] [Example 21] Preparation of compound H2-166

[0275]

[0276] Compound 11 (3.3 g, 10.04 mmol), di([1,1′-biphenyl]-4-yl)amine (3.2 g, 10.04 mmol), tris(dibenzylacetone)dipalladium(O) (0.5 g, 0.50 mmol), tri-tert-butylphosphine (0.5 mL, 1.04 mmol), sodium tert-butoxide (1.5 g, 15.06 mmol), and 50 mL of toluene were added to a flask, and the mixture was stirred under reflux for 4 hours. After cooling the reaction mixture to room temperature, the solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound H2-166 (3.2 g, yield: 52%).

[0277] compound MW MP H2-166 613.79 213℃

[0278] [Example 22] Preparation of compound H2-230

[0279]

[0280] Compound 6 (2.14 g, 7.1 mmol), compound 15 (2.5 g, 7.1 mmol), Pd(OAc)2 (0.08 g, 0.36 mmol), tri-tert-butylphosphine (0.35 mL, 0.71 mmol), sodium tert-butoxide (1.4 g, 14.2 mmol), and 36 mL of o-xylene were added to a reaction vessel, and the mixture was stirred at 165 °C for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The residue was then purified by column chromatography to obtain compound H2-230 (2.0 g, yield: 12%).

[0281] compound MW H2-230 615.69

[0282] The luminous efficiency and lifetime characteristics of the organic electroluminescent device (OLED) according to this disclosure will be explained in detail below. However, the following examples are only illustrative of the characteristics of the OLED according to this disclosure, and this disclosure is not limited to the following examples.

[0283] Apparatus Examples 1 to 7: Production of the first and second main compounds according to the present disclosure by co-evaporation OLED

[0284] OLEDs according to this disclosure are produced. A transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol before use. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1, as shown in Table 2, is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Compound HT-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emitting layer was formed thereon as follows: each of the first and second host compounds shown in Table 1 below was introduced as a host into two chambers of the vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into the other chamber. The two host materials were evaporated at a 1:1 ratio, while the dopant materials were evaporated at different rates, and the dopant was deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form an emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ET-1 and EI-1 were deposited at a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the emitting layer. After depositing compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced. All materials used in the production of the OLED were [processed / conducted / etc.]. -6 Purification is achieved through vacuum sublimation.

[0285] Comparative Examples 1 to 3: Production of OLEDs Containing Comparative Compounds as the Main Body

[0286] The OLEDs are produced in the same manner as in Device Examples 1 to 7, except that only the second host compound in Table 1 below is used as the host of the light-emitting layer.

[0287] Table 1 below provides the driving voltage, luminous efficiency, and emission color of the OLEDs produced in Device Examples 1 to 7 and Comparative Examples 1 to 3 at a brightness of 1,000 nits, as well as the time taken for the light intensity to decrease from 100% to 95% at a brightness of 10,000 nits (lifetime: T95).

[0288] [Table 1]

[0289]

[0290] As can be seen from Table 1 above, compared with OLEDs using a single host material (Comparative Examples 1 to 3), OLEDs containing a specific combination of compounds according to the present disclosure as host materials exhibit lower driving voltage and higher luminous efficiency, and particularly significantly improved lifetime.

[0291] The compounds used in the apparatus examples and comparative examples are shown in Table 2 below.

[0292] [Table 2]

[0293]

Claims

1. A plurality of host materials, comprising a first host material and a second host material, wherein the first host material comprises a compound represented by Formula 1, and the second host material comprises a compound represented by Formula 2: ----- (1) In Equation 1, It can be represented by the following formula 1-1-1 or 1-2-1; L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -NR. 11 R 12 ;and R 11 To R 12 Each can be independently represented as a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; ---- (1-1-1) In Equation 1-1-1, R 31 To R 33 Each of these elements independently represents hydrogen, deuterium, 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 mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino; and aa represents integers from 1 to 5, ab represents integers from 1 to 4, and ac represents integers from 1 to 3. Furthermore, if aa, ab, and ac are integers of 2 or greater, then each R... 31 Each R 32 and each R 33 They can be the same as or different from each other; ---- (1-2-1) In Equation 1-2-1, R 41 To R 44 Each of these elements independently represents hydrogen, deuterium, 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 mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino; and ba represents an integer of 1 or 2, bb and bc each independently represent integers from 1 to 4, and bd represents integers from 1 to 3. Furthermore, if ba, bb, bc, and bd are integers of 2 or greater, then each R... 41 Each R 42 Each R 43 and each R 44 They can be the same as or different from each other; and ----- (2) In Equation 2, X' represents O, S, or CR5R6; R1 to R4 each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -L3-NR. 16 R 17 ; in, At least one of R1 to R4 represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, or -L3-NR. 16 R 17 ; L3 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; R5 and R6 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or R5 and R6 may be connected to each other to form one or more rings; R 16 To R 17 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and a' and d' each independently represent an integer from 1 to 4, b' and c' each independently represent an integer of 1 or 2, and each R1 to each R4 can be the same or different from each other if each of a' to d' is an integer of 2 or greater.

2. The various main body materials according to claim 1, wherein, In equation 1-1-1, R 31 To R 33 Each can be independently represented as hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl.

3. The various main body materials according to claim 1, wherein, In equation 1-2-1, R 41 To R 44 Each can be independently represented as hydrogen, deuterium, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl.

4. The various main body materials according to claim 1, wherein, In Equation 2, X' represents O or S.

5. The various main body materials according to claim 1, wherein, In Equation 2, At least one of R1 to R4 is -L2-HAr or -L3-NR 16 R 17 ; L2 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group containing at least one of N, O, and S; and L3, R 16 and R 17 Each is independently defined as in claim 1.

6. The various main body materials according to claim 1, wherein, The compound represented by formula 2 is represented by any one of the following formulas 2-1 to 2-4: ---- (2-1) ---- (2-2) ---- (2-3) ---- (2-4) In equations 2-1 to 2-4, R1 to R4 each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -L3-NR. 16 R 17 ; X', L3, R 16 R 17 , and a' to d' are as defined in claim 1; L2 independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Z1 to Z3 each independently represent N or CH, provided that at least one of Z1 to Z3 is N; Ar2 and Ar3 each independently represent substituted or unsubstituted (C6-C30) aryl groups, or substituted or unsubstituted (3- to 30-membered) heteroaryl groups; and Each e' independently represents an integer from 1 to 3, and each R1 and each R4 can be the same or different from each other if each e' is an integer of 2 or greater.

7. The various main body materials according to claim 1, wherein, The compound represented by formula 2 is represented by any one of the following formulas 2-5 to 2-8: ---- (2-5) ---- (2-6) ---- (2-7) ---- (2-8) In equations 2-5 to 2-8, R1 to R4 each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -L3-NR. 16 R 17 ; X', L3, R 16 R 17 、 and a' to d' are as defined in claim 1; and Each e' independently represents an integer from 1 to 3, and each R1 and each R4 can be the same or different from each other if each e' is an integer of 2 or greater.

8. The various main body materials according to claim 1, wherein, The compound represented by Formula 1 is at least one selected from the group consisting of: and .

9. The various main body materials according to claim 1, wherein, The compound represented by Formula 2 is at least one selected from the group consisting of: 。 10. The plurality of main body materials according to claim 1, wherein, The substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, and one or more of the substituted cycloalkyl groups are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocyclic alkyl; ( (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or substituted (3- to 30-membered) heteroaryl with at least one of (C1-C30) alkyl, (C6-C30) aryl, (3- to 30-membered) heteroaryl, and di(C6-C30) arylamino; unsubstituted or substituted (C6-C30) aryl with at least one of deuterium, cyano, (C1-C30) alkyl, (3- to 50-membered) heteroaryl, mono- or di-(C6-C30) arylamino, and tri(C6-C30) arylsilyl; tri(C1-C30) alkylsilyl; tri(C6-C 30) Arylsilyl; Di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; Amino; Mono- or Di-(C1-C30)alkylamino; Mono- or Di-(C2-C30)alkenylamino; Mono- or Di-(C6-C30)arylamino; Mono- or Di-(3- to 30-membered)heteroarylamino; (C1-C30)alkyl(C2-C30)alkenylamino; (C1-C30)alkyl(C6-C30)arylamino; (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; di(C6-C30)arylboroncarbonyl; di(C1-C30)alkylboroncarbonyl; (C1-C30)alkyl(C6-C30)arylboroncarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

11. An organic electroluminescent device, comprising: anode; cathode; and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of body materials as described in claim 1.

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