Organic electroluminescent compound, plurality of host materials, and organic electroluminescent device comprising the same

Abstract

The present disclosure relates to an organic electroluminescent compound represented by Formula 1, a plurality of host materials comprising a combination of specific compounds, and an organic electroluminescent device comprising the same. By comprising an organic electroluminescent compound or a specific combination of compounds according to the present disclosure as a host material and / or an electron transport zone material, an organic electroluminescent device having improved driving voltage, luminous efficiency, and / or lifespan characteristics compared to conventional organic electroluminescent devices can be provided.

Description

Technical Field

[0001] This disclosure relates to organic electroluminescent compounds, host materials comprising combinations of specific compounds, and organic electroluminescent devices comprising the same. Background Technology

[0002] Small-molecule organic light-emitting diodes (OLEDs) were first developed in 1987 by Tang et al. of Eastman Kodak using a TPD / ALq3 bilayer consisting of an emissive layer and a charge transport layer. Since then, OLED development has been rapidly influenced, and OLEDs have been commercialized. Currently, OLEDs primarily use phosphorescent materials with excellent luminous efficiency in panel implementation. For long-term use and high resolution of displays, OLEDs with low driving voltage, high luminous efficiency, and / or long lifetime are required. Furthermore, in addition to conventional red, green, and blue emissive materials, green emissive materials have recently been used in OLEDs. However, compared to phosphorescent red materials, phosphorescent green materials have a shorter lifetime, thus requiring improvements in their lifetime.

[0003] Meanwhile, Korean Patent Application Publication No. 2015-0116776 discloses an organic electroluminescent device comprising bicarbazole derivative compounds and carbazole derivative compounds as multiple host materials. Furthermore, Korean Patent No. 1498278 discloses carbazole derivative compounds as a single host material, a hole transport layer material, or a light-emitting auxiliary layer material. Additionally, Chinese Patent Application Publication No. 103467450 discloses a carbazole derivative compound as a single host material. However, there is still a need to develop light-emitting materials with improved performance (e.g., improved driving voltage, luminous efficiency, power efficiency, and / or lifetime characteristics) compared to the specific compounds disclosed in the aforementioned references. Summary of the Invention

[0004] Technical issues

[0005] The purpose of this disclosure is to provide an organic electroluminescent compound having a novel structure suitable for application in organic electroluminescent devices. Another purpose of this disclosure is to provide an improved organic electroluminescent material capable of providing organic electroluminescent devices with improved luminous efficiency and / or long lifetime characteristics. Yet another purpose of this disclosure is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency, and / or lifetime characteristics by comprising a specific combination of compounds as a host material and / or an electron transport region material.

[0006] Solution to the problem

[0007] The inventors of this invention have discovered that the above-mentioned objectives can be achieved by a compound represented by Formula 1. The compound represented by Formula 1 can be applied as a variety of host materials in organic electroluminescent devices in combination with a compound represented by Formula 2.

[0008]

[0009] In Equation 1,

[0010] HAr indicates substituted or unsubstituted heteroaryl groups (ranging from 3 to 30 ppm);

[0011] L1 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene.

[0012] R1 to R8 independently represent hydrogen, 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 13 R 14 or -SiR 15 R 16 R 17 Alternatively, it can be attached to adjacent substituents to form one or more rings.

[0013] The prerequisite is that at least one of the groups R5 and R6, R6 and R7, and R7 and R8 of Formula 1 is fused with *of Formula 1-a below to form one or more rings.

[0014]

[0015] In equation 1-a,

[0016] Y1 represents O or S.

[0017] R9 to R 12 Each of these can independently represent hydrogen, 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 18 R 19 or -SiR 20 R 21 R22 ,

[0018] R 13 To R 22 Each can independently represent hydrogen, 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, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;

[0019] Dn represents n hydrogen atoms being replaced by deuterium; and

[0020] n represents an integer from 1 to 50.

[0021]

[0022] In Equation 2,

[0023] A1 and A2 each independently represent substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-membered to 30-membered) heteroaryl;

[0024] L 11 Indicates a single bond, or a substituted or unsubstituted (C6-C30) aryl group;

[0025] X', X", X 11 To X 14 and X 23 To X 26 Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) ynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 23 R 24 or -SiR 25 R 26 R 27 Alternatively, it can be attached to adjacent substituents to form one or more rings;

[0026] R 23 To R 27Each can independently represent hydrogen, 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, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;

[0027] m and n each independently represent integers from 1 to 3; and

[0028] If m and n are integers of 2 or greater, then each X' and each X" can be the same or different.

[0029] Beneficial effects of the present invention

[0030] The organic electroluminescent compounds according to this disclosure exhibit performance suitable for use in organic electroluminescent devices. Furthermore, by including specific combinations of compounds according to this disclosure as host materials and / or electron transport region materials, an organic electroluminescent device with high luminous efficiency and / or long lifetime characteristics compared to conventional organic electroluminescent devices is provided. For example, by including compounds according to this disclosure, a green-emitting or blue-emitting organic electroluminescent device with improved lifetime characteristics can be provided. Detailed Implementation

[0031] 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.

[0032] 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. If desired, 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.

[0033] The term "multiple organic electroluminescent materials" in this disclosure refers to an organic electroluminescent material comprising a combination of at least two compounds, said material being contained in any organic layer constituting an organic electroluminescent device. It can mean both materials contained before (e.g., before vapor deposition) and materials contained after (e.g., after vapor deposition) the organic electroluminescent device. For example, the multiple organic electroluminescent materials of this disclosure can be a combination of at least two compounds, said material being contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The at least two compounds can be contained in the same or different layers by methods used in the art, and can be co-evaporated or mixed, or can be evaporated individually.

[0034] The term "multiple host materials" in this disclosure refers to a host material comprising a combination of at least two host materials, 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. For example, the multiple host materials of this disclosure are combinations of at least two host materials, and may optionally further include conventional materials included in organic electroluminescent materials. 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, they may be co-evaporated or mixed, or the at least two host materials may be evaporated individually.

[0035] The organic electroluminescent material disclosed herein may contain at least one compound represented by Formula 1. The compound represented by Formula 1 may be contained in the emissive layer, but is not limited thereto. When contained in the emissive layer, the compound represented by Formula 1 may be contained as a host material. Furthermore, the compound represented by Formula 1 may be contained in the electron transport region. Additionally, the compound represented by Formula 1 may be contained in the electron buffer layer, but is not limited thereto.

[0036] In this document, the term "(C1-C30)alkylene" refers to a straight-chain or branched (alkylene)ene 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)cycloalkylene" 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 selected from the group consisting of O, S, and N. The above heterocyclic alkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. The term "(C6-C30)(aryl) group" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 cyclic skeleton carbon atoms. The above (aryl) groups may be partially saturated and may 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, anthracene, indene, benzo[a]phenanthrene, pyrene, tetraphenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, spiro[fluorene-benzo[fluorene]]yl, azuleyl, 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, benzo[fluoranthyl]fluoranthyl, 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.

[0037] The term "(3- to 30-membered) (hypo)aryl" refers 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 (hypo)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 (hypo)aryl group formed by linking at least one heteroaryl group or an 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, and diphenyl benzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuran-quinolinyl, benzofuran-quinazolinyl, benzofuran-naphthidyl, benzofuran-pyrimidyl, naphthofuran-pyrimidyl, benzothiophene-quinolinyl, benzothiophene-quinazolinyl, benzothiophene-naphthidyl, benzothiophene-pyrimidyl, naphthophene-pyrimidyl, pyrimidylindole Benzyl, benzopyrimidine-indolyl, benzofuran-pyrazinyl, naphthofuran-pyrazinyl, benzothiophene-pyrazinyl, naphthothiophene-pyrazinyl, pyrazin-indolyl, benzopyrazin-indolyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl The compounds include quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthidyl, benzodioxanepentenyl, dihydroacridinyl, benzotriazolephenazinyl, imidazopyridyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzoperimidinyl, indolocarbazolyl, indolecarbazolyl, and indolecarbazolyl. More specifically, the aforementioned heteroaryl groups may include 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, 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 -Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 8-Indolyl, 2-Imidazolopyridyl, 3-Imidazolopyridyl, 5-Imidazolopyridyl, 6-Imidazolopyridyl, 7-Imidazolopyridyl, 8-Imidazolopyridyl, 3-pyridyl, 4-pyridyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl 2-quinolinyl, 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 -quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 9-carbazoleyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole 8-yl, azacarbazolyl-9-yl, 1-phenanthrynyl, 2-phenanthrynyl, 3-phenanthrynyl, 4-phenanthrynyl, 6-phenanthrynyl, 7-phenanthrynyl, 8-phenanthrynyl, 9-phenanthrynyl, 10-phenanthrynyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl 5-Oxadiazolyl, 3-Furazolyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrolo-1-yl, 2-Methylpyrrolo-3-yl, 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 Furanyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2]-benzofuranyl [-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl, 8-naphtho-[1,2-b]-benzofuranyl, 9-naphtho-[1,2-b]-benzofuranyl, 10-naphtho-[1,2-b]-benzofuranyl,1-Naphtho-[2,3-b]-benzofuranyl, 2-Naphtho-[2,3-b]-benzofuranyl, 3-Naphtho-[2,3-b]-benzofuranyl, 4-Naphtho-[2,3-b]-benzofuranyl, 5-Naphtho-[2,3-b]-benzofuranyl, 6-Naphtho-[2,3-b]-benzofuranyl, 7-Naphtho-[2,3-b]-benzofuranyl ]-Benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuranyl, 1-naphtho-[2,1-b]-benzofuranyl, 2-naphtho-[2,1-b]-benzofuranyl, 3-naphtho-[2,1-b]-benzofuranyl, 4- Naphtho-[2,1-b]-benzofuranyl, 5-naphtho-[2,1-b]-benzofuranyl, 6-naphtho-[2,1-b]-benzofuranyl, 7-naphtho-[2,1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b] -Benzofuranyl, 1-Naphtho-[1,2-b]-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 -[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]-benzyl 4-Naphtho-[2,3-b]-benzothiophene, 5-Naphtho-[2,3-b]-benzothiophene, 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]pyrimidine 6-benzofuran[3,2-d]pyrimidinyl, 7-benzofuran[3,2-d]pyrimidinyl, 8-benzofuran[3,2-d]pyrimidinyl, 9-benzofuran[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl,8-Benzothio[3,2-d]pyrimidinyl, 9-Benzothio[3,2-d]pyrimidinyl, 2-Benzofuran[3,2-d]pyrazinyl, 6-Benzofuran[3,2-d]pyrazinyl, 7-Benzofuran[3,2-d]pyrazinyl, 8-Benzofuran[3,2-d]pyrazinyl, 9-Benzofuran[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio [3,2-d]pyrazinyl, 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-siliconyl, 2-siliconyl, 3-siliconyl, 4-siliconyl, 1-germaniumyl, 2-germaniumyl, 3-germaniumyl, 4-germaniumyl, 1-dibenzo[2,2-d]selenophenyl, 2-dibenzo[2,2-d]selenophenyl, 3-dibenzo[2,2-d]selenophenyl, 4-dibenzo[2,2-d]selenophenyl, etc. In addition, "halogens" include F, Cl, Br, and I.

[0038] 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.

[0039] 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 document, one or more substituents of substituted ()alkylene, substituted alkenyl, substituted alkynyl, substituted ()aryl, substituted ()heteroaryl, substituted ()cycloalkylene, substituted cycloalkenyl, and substituted heterocycloalkyl are each independently selected from at least one of the following groups: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; phosphine oxide; (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 deuterium and (C6- to 30-membered) aryl; unsubstituted or substituted (C6-C30)aryl with at least one of deuterium and (C6- to 30-membered) heteroaryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6- (C30) arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C2-C30)alkenylamino; unsubstituted or mono- or di-(C6-C30)arylamino substituted with one or more (C1-C30)alkyl groups; 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)aryl Amino; (C2-C30)alkenyl(3- to 30-membered)heteroarylamino; (C6-C30)aryl(3- to 30-membered)heteroarylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; (C6-C30)arylphosphine; di(C6-C30)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 at least one selected from the group consisting of: deuterium; (C1-C20)alkyl; unsubstituted (5- to 25-membered) heteroaryl group substituted with at least one of deuterium and (C6-C25) aryl group; unsubstituted (C6-C25) aryl group substituted with at least one of deuterium and (C6- to 25-membered) heteroaryl group; and tri(C6-C25) arylsilyl. According to another embodiment of the present disclosure, each of the one or more substituents is independently at least one selected from the group consisting of: deuterium; (C1-C10)alkyl; unsubstituted (5- to 20-membered) heteroaryl group substituted with at least one of deuterium and (C6-C18) aryl group; unsubstituted (C6-C18) aryl group substituted with at least one of deuterium and (C6- to 20-membered) heteroaryl group; and tri(C6-C18) arylsilyl. For example, the one or more substituents may be at least one selected from the group consisting of: deuterium; methyl; phenyl; phenyl substituted with at least one deuterium; phenyl substituted with one or more carbazolyls; naphthyl; biphenyl; unsubstituted or substituted with one or more phenyl groups; dibenzofuranyl; dibenzothiophenyl; carbazolyl substituted with one or more phenyl groups; and triphenylsilyl.

[0040] 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 (C6-C18) aryl and (3-membered to 20-membered) heteroaryl groups. 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 may be a benzene ring; an indole ring substituted with at least one of phenyl, biphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, terphenyl, benzophenanthryl, phenylpyridyl, and phenylpyrimidinyl; an unsubstituted or substituted spiro[indene-xanton] ring; an unsubstituted or substituted xanton ring, etc.

[0041] 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 be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)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. alkylamino, 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.

[0042] The various host materials disclosed herein include 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. According to one embodiment of this disclosure, the compound represented by Formula 1 and the compound represented by Formula 2 are different from each other.

[0043] In Formula 1, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, HAr represents a substituted or unsubstituted nitrogen-containing (5- to 25-membered) heteroaryl group. According to another embodiment of this disclosure, HAr represents a nitrogen-containing (5- to 20-membered) heteroaryl group substituted with at least one of deuterium, (C6-C30) aryl, and (3- to 30-membered) heteroaryl. Specifically, HAr can be a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted isoquinoxalinyl group, a substituted or unsubstituted benzoisoquinoxalinyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphridyl group, a substituted or unsubstituted triazanaphthyl group, or a substituted or unsubstituted benzothiophene pyrimidinyl group. For example, HAr can be a substituted triazine, substituted pyrimidin, substituted quinazoline, or substituted quinoxaline, wherein one or more of the substituted triazine, substituted pyrimidin, substituted quinoxaline, and substituted quinoxaline can each independently be at least one of an unsubstituted or deuterated and / or carbazoline-substituted phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, and carbazoline-substituted with one or more phenyl groups.

[0044] In Formula 1, L1 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. According to one embodiment of this disclosure, L1 represents 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, L1 represents a single bond, an unsubstituted or deuterated (C6-C18) arylene, or an unsubstituted or deuterated (5- to 20-membered) heteroarylene. For example, L1 may be a single bond, an unsubstituted or deuterated phenylene, an unsubstituted or deuterated biphenylene, or an unsubstituted or deuterated dibenzofuranyl. Specifically, L1 can be a single bond or an unsubstituted or at least deuterated dibenzofuranyl group, or can be represented by any one of the following groups:

[0045]

[0046]

[0047] In the above formula, X iTo X p Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) ynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 28 R 29 or -SiR 30 R 31 R 32 Alternatively, it can be attached to adjacent substituents to form one or more rings. For example, X i Each of X can be either hydrogen or deuterium.

[0048] In Formula 1, R1 to R8 each independently represent hydrogen, 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 13 R 14 or -SiR 15 R 16 R 17 Alternatively, it can be attached to an adjacent substituent to form one or more rings.

[0049] According to one embodiment of this disclosure, R1 to R4 each independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-membered to 25-membered) heteroaryl. According to another embodiment of this disclosure, R1 to R4 each independently represent hydrogen, deuterium, unsubstituted or deuterated (C6-C18) aryl, or unsubstituted or deuterated (5-membered to 20-membered) heteroaryl. For example, R1 to R4 each independently can be hydrogen, deuterium, unsubstituted or deuterated phenyl, unsubstituted or deuterated biphenyl, unsubstituted or deuterated dibenzofuranyl, or unsubstituted or deuterated carbazolyl.

[0050] According to one embodiment of this disclosure, R5 to R8 each independently represent hydrogen or deuterium; or they may be attached to adjacent substituents to form one or more rings. For example, R5 to R8 each independently can be hydrogen or deuterium; or they may be attached to adjacent substituents to form an unsubstituted or deuterated benzene ring, an unsubstituted or deuterated benzofuran ring, or an unsubstituted or deuterated benzothiophene ring.

[0051] At least one of the groups R5 and R6, R6 and R7, and R7 and R8 of Formula 1 is fused with * of Formula 1-a below to form one or more rings.

[0052]

[0053] In Equation 1-a, Y1 represents O or S.

[0054] In equation 1-a, R9 to R 12 Each of these can independently represent hydrogen, 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 18 R 19 or -SiR 20 R 21 R 22 According to one embodiment of this disclosure, R9 to R 12 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C25) aryl group. According to another embodiment of this disclosure, R9 to R... 12 Each can independently represent hydrogen, deuterium, or an unsubstituted or deuterated (C6-C18) aryl group. For example, R9 to R 12 Each can be hydrogen, deuterium, or an unsubstituted or deuterated phenyl group.

[0055] In Formula 1, Dn represents n hydrogen atoms replaced by deuterium; and n independently represents an integer from 1 to 50. According to one embodiment of this disclosure, n independently represents an integer from 5 to 50. According to another embodiment of this disclosure, n independently represents an integer from 6 to 50. According to yet another embodiment of this disclosure, n independently represents an integer from 7 to 50. When deuteration reaches the lower limit number or more, the bond dissociation energy associated with deuteration may increase to exhibit improved lifetime characteristics. The upper limit of n is determined by the number of hydrogen atoms that can be substituted in each compound.

[0056] R 13 To R 22 and R 28 To R 32Each can independently represent hydrogen, 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) heterocyclic alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to an adjacent substituent to form one or more rings.

[0057] According to one embodiment of this disclosure, Formula 1 can be represented by at least one of Formulas 1-1 to 1-18 below.

[0058]

[0059]

[0060]

[0061] In equations 1-1 to 1-18, R1 to R 12 Y1, L1, HAr and Dn are defined as in Equation 1.

[0062] In Formula 2, A1 and A2 each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of this disclosure, A1 and A2 each independently represent a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group. According to another embodiment of this disclosure, A1 and A2 each independently represent an unsubstituted (C6-C18) aryl group, or a group substituted with at least one of deuterium, (C1-C30) alkyl, (C6-C30) aryl, (3- to 30-membered) heteroaryl, and tri(C6-C30)arylsilyl. Specifically, A1 and A2 can each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzo[a]fluorenyl, a substituted or unsubstituted benzo[a]phenanthryl, a substituted or unsubstituted fluoranyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazoleyl, or a substituted or unsubstituted dibenzothiopheneyl. For example, A1 and A2 can each independently be a substituted or unsubstituted phenyl, naphthyl, biphenyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, or dimethylbenzo[a]fluorenyl, wherein the substituent of the substituted phenyl can be at least one of unsubstituted or substituted methyl, naphthyl, triphenylsilyl, and pyridyl groups.

[0063] In Equation 2, L 11This represents a single-bonded, substituted, or unsubstituted (C6-C30) aryl group. According to one embodiment of this disclosure, L... 11 This represents a single-bonded, substituted, or unsubstituted (C6-C25) aryl group. According to another embodiment of this disclosure, L... 11 This indicates a single bond or an unsubstituted (C6-C18) aryl group. For example, L 11 It can be a single bond, phenylene, naphthylene, or biphenylene.

[0064] In Equation 2, X', X", X 11 To X 14 and X 23 To X 26 Each of these can independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) ynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 23 R 24 or -SiR 25 R 26 R 27 Alternatively, they can be attached to adjacent substituents to form one or more rings. According to one embodiment of this disclosure, X', X”, X… 11 To X 14 and X 23 To X 26 Each can independently represent hydrogen, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group; or can be attached to an adjacent substituent to form one or more rings. According to another embodiment of this disclosure, X', X”, X… 11 To X 14 and X 23 To X 26 Each can independently represent hydrogen or an unsubstituted (5- to 20-membered) heteroaryl group; or it can be attached to an adjacent substituent to form one or more rings. For example, X' and X” can be hydrogen; and X 11 To X 14 and X 23 To X 26 Each can be independently hydrogen, dibenzothiophene, or dibenzofuran, or can be attached to an adjacent substituent to form one or more benzene rings.

[0065] R 23 To R 27Each can independently represent hydrogen, 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) heterocyclic alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to an adjacent substituent to form one or more rings.

[0066] In Equation 2, m and n each independently represent integers from 1 to 3, where if m and n are integers of 2 or greater, each X' and each X” can be the same or different. For example, m and n can each independently be 1.

[0067] According to one embodiment of this disclosure, formula 2 can be represented by at least one of formulas 2-1 to 2-8 below.

[0068]

[0069]

[0070] In equations 2-1 to 2-8, A1, A2, X 11 To X 14 and X 23 To X 26 It is as defined in Equation 2; and X 15 To X 22 Each is independently identical to the definition of X' in Equation 2.

[0071] The compounds represented by Formula 1 can be exemplified as the following compounds, but are not limited thereto.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] A combination of at least one of compounds H1-1 to H1-236 and at least one of compounds H2-1 to H2-33 can be used in organic electroluminescent devices.

[0085] This disclosure provides an organic electroluminescent compound represented by Formula 1, wherein n represents an integer from 5 to 50. According to one embodiment of this disclosure, the compound may be at least one of compounds H1-1 to H1-236, wherein n independently represents an integer from 5 to 50. According to another embodiment of this disclosure, at least one of compounds H1-1 to H1-236 (where n represents an integer from 5 to 50) may be used in an organic electroluminescent device. This disclosure may provide an organic electroluminescent device comprising the organic electroluminescent compound, wherein the organic electroluminescent compound may be contained in a light-emitting layer.

[0086] Non-deuterated analogues of the compounds represented by Formula 1 can be prepared via known coupling and substitution reactions. Alternatively, compounds of Formula 1 can be prepared in a similar manner using deuterated precursor materials, or more generally by treating undeuterated compounds with a deuterated solvent or D6-benzene in the presence of an H / D exchange catalyst (such as a Lewis acid, e.g., aluminum trichloride or ethylaluminum chloride, trifluoromethanesulfonic acid, or trifluoromethanesulfonic acid-D). Furthermore, the degree of deuteration can be controlled by altering reaction conditions such as reaction temperature. For example, the number n in Formula 1 can be controlled by adjusting the reaction temperature and time, the acid stoichiometry, etc.

[0087] The compound represented by Formula 1 according to this disclosure can be produced by synthetic methods known to those skilled in the art, and for example, by reference to Korean Patent No. 1427457 (published August 8, 2014), Korean Patent Application Publication No. 2012-0101029 (published September 12, 2012), or according to reaction schemes 1 to 3 below, but not limited thereto.

[0088] [Reaction Scheme 1]

[0089]

[0090] [Reaction Scheme 2]

[0091]

[0092] [Reaction Scheme 3]

[0093]

[0094] In reaction schemes 1 to 3, R1 to R6, R9 to R... 12 Y1, L1, HAr and Dn are defined as in Equation 1; and X1 and X2 indicate that deuterium can be substituted by substituents defined in this disclosure.

[0095] The compound represented by Formula 2 according to this disclosure can be synthesized by methods known to those skilled in the art, and, for example, by reference to Japanese Patent No. 3139321 (published February 26, 2001), Korean Patent Application Publication No. 2010-0079458 (published July 8, 2010), Korean Patent No. 1170666 (published August 7, 2012), Korean Patent Application Publication No. 2012-0085827 (published August 1, 2012), Korean Patent Application Publication No. 2014-0037814 (published March 27, 2014), International Patent Publication No. WO 2012 / 153725 (published November 15, 2012), Korean Patent Application Publication No. 2013-009614 (published January 23, 2013), and International Patent Publication No. WO It can be produced using patents such as 2013 / 084881 (published on June 13, 2013), International Patent Publication No. WO2013 / 146117 (published on October 3, 2013), International Patent Publication No. WO 2013 / 146942 (published on October 3, 2013), and International Patent Publication No. WO 2014 / 017484 (published on January 30, 2014), but is not limited to these.

[0096] Although illustrative synthetic examples of the compounds represented by Formulas 1 and 2 of this disclosure 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, Miyaura borylation reactions, Suzuki cross-coupling reactions, Pd(II)-catalyzed oxidative cyclization reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, Ullmann reactions, Wittig reactions, etc., and that the above reactions continue even when substituents defined in Formulas 1 and 2 above but not specified in the specific synthetic examples are bonded.

[0097] The organic electroluminescent device according to this disclosure may include an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may contain a variety of organic electroluminescent materials, including a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of this disclosure, the organic electroluminescent device may include an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers may contain a compound represented by Formula 1 and a compound represented by Formula 2, preferably a variety of host materials disclosed herein.

[0098] In this paper, the electrodes can be semi-transparent reflective electrodes or reflective electrodes, and depending on the material, they can be top-emitting, bottom-emitting, or side-emitting. 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.

[0099] The light-emitting layer includes a host and dopants, wherein the host comprises multiple host materials, and a compound represented by Formula 1 may be included as a first host compound of the multiple host materials, and a compound represented by Formula 2 may be included as a second host compound of the multiple host materials. The weight ratio of the first host compound to the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to about 60:40, and even more preferably about 50:50. When at least two materials are included in a layer, they may be mixed and evaporated to form the layer, or they may be co-evaporated separately and simultaneously to form the layer.

[0100] In this disclosure, the light-emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. All of the first and second host materials may be contained in one layer, or the first and second host materials may be contained in their respective separate light-emitting layers. 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 20 wt%.

[0101] This disclosure may include a hole transport region between the anode and the light-emitting layer, and the hole transport region may include at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer. The hole injection layer, hole transport layer, hole auxiliary layer, light-emitting auxiliary layer, and electron blocking layer may each be a single layer or a multilayer comprising two or more layers stacked therein. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayers. The electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may prevent light leakage by confining excitons within the light-emitting layer and blocking electrons from escaping from the light-emitting layer.

[0102] Furthermore, the hole transport region may include a p-type doped hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. A p-type doped hole injection layer refers to a hole injection layer doped with a p-type dopant. A p-type dopant is a material that imparts p-type semiconductor characteristics to the layer. P-type semiconductor characteristics refer to the material's ability to inject or transport holes to HOMO (highest occupied molecular orbital) energy levels; that is, the material characteristic of high hole conductivity.

[0103] This disclosure may include an electron transport region between the light-emitting layer and the cathode, and said electron transport region may include at least one of a hole blocking layer, an electron transport layer, an electron buffer layer, and an electron injection layer. The hole blocking layer, electron transport layer, electron buffer layer, and electron injection layer may each be a single layer, or a multilayer comprising two or more layers stacked therein. The electron injection layer may be further doped with an n-type dopant. The electron buffer layer may be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers may use two compounds simultaneously. The hole blocking layer or electron transport layer may also be multilayered, wherein each of the multilayers may use multiple compounds. According to one embodiment of this disclosure, at least one layer of the electron transport region, preferably the electron buffer layer, may contain a compound represented by Formula 1.

[0104] 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 promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. 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. 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, and electron blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0105] The dopant included in the organic electroluminescent device of this disclosure can 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 can preferably be selected from metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, more preferably from ortho-metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) complexes, and even more preferably from ortho-metallized iridium complexes.

[0106] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0107] 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.

[0108] Furthermore, the compounds represented by Formula 1 and Formula 2 can be film-formed using the methods listed above, typically through co-evaporation or mixed evaporation. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective individual crucible sources and an electric current is simultaneously applied to both chambers to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in a crucible source before evaporation and an electric current is applied to the chambers to evaporate the materials.

[0109] The organic electroluminescent material according to this disclosure can be used as a luminescent material 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. This disclosure can also be applied to white organic light-emitting devices. Furthermore, the organic electroluminescent material according to this disclosure can also be used in organic electroluminescent devices incorporating quantum dots (QDs).

[0110] This disclosure provides a display system incorporating various body materials disclosed herein. Furthermore, display systems or lighting systems can be manufactured using the organic electroluminescent devices of this disclosure. Specifically, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be produced using the organic electroluminescent devices of this disclosure; or lighting systems, such as outdoor or indoor lighting systems.

[0111] 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.

[0112] Example 1: Preparation of compound H1-211

[0113] Synthesis of Compound 1-1

[0114]

[0115] In a flask, Mg (3.29 g, 135.56 mmol), 60 mL of tetrahydrofuran (THF), and I₂ (0.137 g, 0.54 mmol) were stirred. Bromobenzene-D₅ (21.9 g, 135.56 mmol) was slowly added to the mixture, which was heated to 75 °C and cooled to room temperature after 30 minutes to produce a Grignard reagent. 2,4,6-Trichloro-1,3,5-triazine (10 g, 54.22 mmol) was dissolved in 120 mL of THF, and the mixture was cooled to 0 °C, to which the produced Grignard reagent was slowly added. After stirring at room temperature for 12 hours, an aqueous solution of NH₄Cl was added to the mixture. The organic layer was extracted with ethyl acetate, and the remaining water was removed using magnesium sulfate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound 1-1 (9.5 g, yield: 63.08%).

[0116] Synthesis of Compounds 1-2

[0117]

[0118] Add 12H-benzo[4,5]thieno[2,3-a]carbazole (25 g, 91.45 mmol), 4-bromoiodobenzene (51.58 g, 182.9 mmol), CuI (13.9 g, 73.16 mmol), 1000 mL toluene, Cs₂CO₃ (74.5 g, 228.6 mmol), and ethylenediamine (12.2 mL, 182.9 mmol) to a flask. Heat the mixture to 155 °C and cool to room temperature after 5 hours. Add distilled water to the mixture and extract the organic layer with ethyl acetate. After removing the remaining water with magnesium sulfate, distill the residue under reduced pressure and separate by column chromatography to obtain compounds 1-2 (18.5 g, yield: 47.23%).

[0119] Synthesis of compounds 1-3

[0120]

[0121] Compounds 1-2 (18.5 g, 43.18 mmol), bis(pinacol)diboron (14.25 g, 56.14 mmol), PdCl2(PPh3)2 (1.5 g, 2.16 mmol), KOAc (8.5 g, 86.37 mmol), and 800 mL of 1,4-dioxane were added to a flask. The mixture was heated to 145 °C and cooled to room temperature after 4 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compounds 1-3 (14 g, yield: 68.22%).

[0122] Synthesis of compound H1-211

[0123]

[0124] Compounds 1-3 (14 g, 29.45 mmol), 1-1 (8.9 g, 32.4 mmol), Pd(PPh3)4 (1.7 g, 1.47 mmol), K2CO3 (8.1 g, 58.89 mmol), 400 mL of toluene, 60 mL of distilled water, and 40 mL of ethanol were added to a flask. The mixture was heated to 140 °C and cooled to room temperature after 5 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound H1-211 (10.5 g, yield: 60.3%).

[0125] MW MP H1-211 590 335℃

[0126] Example 2: Preparation of compound H1-212

[0127] Synthesis of Compound 2-1

[0128]

[0129] 5-Bromobenzene-D5 (36 g, 222.16 mmol), 216 mL dichloromethane, I2 (45 g, 177.7 mmol), 108 mL acetic acid, and 3.5 mL sulfuric acid were added to a flask, and the mixture was stirred at 35 °C for 10 min. Then, K2S2O8 (18.01 g, 66.65 mmol) was added to the mixture, the temperature was raised to 45 °C, and the mixture was cooled to room temperature after 4 hours. The reaction solution was slowly added to an aqueous solution of potassium carbonate. After neutralizing the reaction solution, the organic layer was extracted with dichloromethane. The organic layer was added to an aqueous solution of sodium thiosulfate and stirred. The organic and aqueous layers were then separated. The remaining water was removed with magnesium sulfate, and the residue was separated by column chromatography to obtain compound 2-1 (27 g, yield: 42.8%).

[0130] Synthesis of compound 2-2

[0131]

[0132] 12H-benzo[4,5]thieno[2,3-a]carbazole (20 g, 73.16 mmol), compound 2-1 (27.29 g, 95.11 mmol), CuI (11.14 g, 58.53 mmol), 700 mL toluene, Cs₂CO₃ (59.59 g, 182.91 mmol), and ethylenediamine (9.8 mL, 146.3 mmol) were added to a flask. The mixture was heated to 160 °C and cooled to room temperature after 19 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound 2-2 (18.5 g, yield: 47.23%).

[0133] Synthesis of Compounds 2-3

[0134]

[0135] Compound 2-2 (23 g, 53.19 mmol), bis(pinacol)diboron (17.5 g, 69.15 mmol), PdCl2(PPh3)2 (1.86 g, 2.66 mmol), KOAc (10.46 g, 106.4 mmol), and 900 mL of 1,4-dioxane were added to a flask. The mixture was heated to 145 °C and cooled to room temperature after 5 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound 2-3 (14 g, yield: 54.9%).

[0136] Synthesis of compound H1-212

[0137]

[0138] Compounds 2-3 (14 g, 29.20 mmol), 1-1 (8.9 g, 32.12 mmol), Pd(PPh3)4 (1.68 g, 1.46 mmol), K2CO3 (8.0 g, 58.40 mmol), 400 mL of toluene, 60 mL of distilled water, and 40 mL of ethanol were added to a flask. The mixture was stirred under reflux and cooled to room temperature after 5 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. The residue was distilled under reduced pressure and separated by column chromatography to obtain compound H1-212 (10.5 g, yield: 60.45%).

[0139] MW MP H1-212 594 335℃

[0140] Example 3: Preparation of compound H1-213

[0141] Synthesis of compound 3-1

[0142]

[0143] 12H-benzo[4,5]thieno[2,3-a]carbazole (20.0 g, 9.0 mmol) and benzene-D6 (1.2 kg, 14.63 mol) were added to a flask and the mixture was stirred under reflux. Trifluoromethanesulfonic acid (65.88 g, 438.9 mmol) was added to the mixture at 70 °C and cooled to room temperature after 5 hours. 40 mL of D2O was added to the mixture and stirred for 10 minutes. The reaction solution was neutralized with aqueous K3PO4, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound 3-1 (15 g, yield: 72.99%).

[0144] Synthesis of compound H1-213

[0145]

[0146] In a flask, compound 3-1 (14 g, 49.8 mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (23.21 g, 59.78 mmol), Pd(OAc)2 (0.55 g, 2.49 mmol), S-phos (2.04 g, 4.98 mmol), NaOt-Bu (8.6 g, 90.14 mmol), and 500 mL of o-xylene were stirred and heated to 185 °C for 4 hours. The mixture was then cooled to room temperature and distilled water was added. The organic layer was extracted with ethyl acetate and distilled under reduced pressure. The resulting solid was separated by column chromatography to obtain compound H1-213 (20.5 g, yield: 70.0%).

[0147] MW MP H1-213 588 334℃

[0148] Example 4: Preparation of compound H1-36

[0149] Synthesis of compound 4-1

[0150]

[0151] Add 12H-benzo[4,5]thieno[2,3-a]carbazole (20 g, 73.16 mmol), 1-bromo-4-chlorobenzene (42 g, 219.49 mmol), CuI (7 g, 36.58 mmol), 500 mL toluene, K3PO4 (47 g, 219.49 mmol), and ethylenediamine (10 mL, 146.33 mmol) to a flask. Heat the mixture to 160 °C and cool to room temperature after 16 minutes. Add distilled water to the mixture and extract the organic layer with ethyl acetate. After removing the remaining water with magnesium sulfate, distill the residue under reduced pressure and separate by column chromatography to obtain compound 4-1 (9.3 g, yield: 33.2%).

[0152] Synthesis of compound 4-2

[0153]

[0154] Compound 4-1 (8.8 g, 22.97 mmol) and benzene-D6 (528 mL, 5.49 mol) were added to a flask, and then trifluoromethanesulfonic acid (26.4 mL, 293.78 mmol) was added to the mixture. The mixture was heated to 50 °C for 3 hours and then cooled to room temperature. 8.8 mL of D2O was added to the mixture and stirred for 10 minutes. The reaction solution was neutralized with an aqueous solution of K3PO4, and the organic layer was extracted with ethyl acetate. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound 4-2 (8.2 g, yield: 93.2%).

[0155] Synthesis of compound 4-3

[0156]

[0157] Compound 4-2 (8.2 g, 53.19 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (7.95 g, 31.29 mmol), Pd2(dba)3 (1.0 g, 1.09 mmol), S-Phos (1.0 g, 2.43 mmol), KOAc (5.2 g, 52.98 mmol), and 200 mL of 1,4-dioxane were added to a flask. The mixture was heated to 140 °C and cooled to room temperature after 7 hours. Distilled water was added to the mixture and the organic layer was extracted with dichloromethane. After removing the remaining water with magnesium sulfate, the residue was distilled under reduced pressure and separated by column chromatography to obtain compound 4-3 (8.1 g, yield: 80.1%).

[0158] Synthesis of compound H1-36

[0159]

[0160] Compound 4-3 (8.1 g, 16.68 mmol), compound 4-4 (4.2 g, 14.59 mmol), PdCl2(Amphos)2 (0.6 g, 0.84 mmol), Na2CO3 (3.5 g, 33.02 mmol), 63 mL of toluene, 21 mL of distilled water, and Aliquat 336 (0.29 g, 0.73 mmol) were added to a flask. The mixture was stirred under reflux and cooled to room temperature after 4 hours. Distilled water was added to the mixture, and the organic layer was extracted with ethyl acetate. The organic layer was distilled under reduced pressure and separated by column chromatography to obtain compound H1-36 (3 g, yield: 34.2%).

[0161] The following sections will explain in detail the method for producing an organic electroluminescent device (OLED) according to this disclosure, as well as its luminous efficiency and lifetime characteristics. However, this disclosure is not limited to the following examples.

[0162] Device Example 1: Production of OLEDs comprising the host material according to this disclosure

[0163] 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. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Compound HI-1, shown in Table 2, is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1, shown in Table 2, 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 at 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 on the ITO substrate. Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm on the hole injection layer. Compound HT-2 was then introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 30 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: Compounds H1-211 and H2-6, shown in Table 1 below, were introduced as hosts into two chambers of the vacuum vapor deposition apparatus, and compound D-50 was introduced as a dopant into another chamber. The two host materials were evaporated at different rates of 1:2, and the dopant materials were evaporated simultaneously at different rates, and the dopant was deposited at a doping amount of 10 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. Compounds ETL-1 and EIL-1 were evaporated at a weight ratio of 40:60 to form an electron transport layer with a thickness of 35 nm on the emitting layer. After depositing compound EIL-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 phase deposition apparatus. This produced an OLED. All materials used in the production of the OLED were [not specified in the original text]. -6 Purification is achieved through vacuum sublimation.

[0164] Device Example 2: Production of OLEDs comprising the host material according to this disclosure

[0165] The OLED was produced in the same manner as in Device Example 1, except that compound H1-212 was used as the first host of the light-emitting layer.

[0166] Device Example 3: Production of OLEDs comprising the host material according to this disclosure

[0167] The OLED was produced in the same manner as in Device Example 1, except that compound H1-213 was used as the first host of the light-emitting layer.

[0168] Comparative Example 1: Production of OLEDs containing conventional compounds as the primary component

[0169] The OLED is produced in the same manner as in Device Example 1, except that compound C-1 is used as the first host of the light-emitting layer.

[0170] Table 1 below provides the driving voltage, luminous efficiency, and emission color of OLEDs produced in the device examples and comparative examples at a brightness of 1,000 nits, as well as the time (lifetime; T85) taken for the brightness to decrease from 100% to 85% at a brightness of 20,000 nits.

[0171] [Table 1]

[0172]

[0173] As can be seen from Table 1 above, OLEDs incorporating various host materials according to this disclosure exhibit superior luminescence properties and, in particular, improved lifetime properties compared to conventional OLEDs. Specifically, it is demonstrated that introducing one or more deuterated residues into conventional host materials can improve the lifetime properties of green phosphorescent hosts. It should be understood that deuterated compounds lower the zero-point vibrational energy and increase the bond dissociation energy (BDE), thereby improving the stability of the host. Furthermore, this can enhance the performance of the host, thereby improving the lifetime properties of the host, particularly the green phosphorescent host.

[0174] Device Example 4: Production of a blue OLED comprising an electron buffer layer compound according to the present disclosure

[0175] A blue OLED according to this disclosure is produced. A transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geoma 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. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1, shown in Table 2, is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1, shown in Table 2, 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 at 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 on the ITO substrate. Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 75 nm on the hole injection layer. Compound HT-3 was then introduced into another chamber of the vacuum vapor deposition apparatus, and the compound was evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer was formed thereon as follows: Compound C-2, shown in Table 2, was introduced as the host material into one chamber of the vacuum vapor deposition apparatus, and compound C-3 was introduced as the dopant into another chamber. The host material and the dopant material were evaporated at different rates, and the dopant was deposited with a dopant amount of 2 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 20 nm on the second hole transport layer. Compound H1-211 was evaporated to form an electron buffer layer with a thickness of 5 nm on the light-emitting layer. Compounds ETL-1 and EIL-1 were evaporated in a weight ratio of 4:6 to form an electron transport layer with a thickness of 30 nm on the electron buffer layer. After depositing compound EIL-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 phase deposition apparatus. This produced an OLED. All materials used in the production of the OLED were [not specified in the original text]. -6 Purification is achieved through vacuum sublimation.

[0176] The shortest time (lifetime; T95) for the produced OLED to decrease from 100% to 95% brightness at 1,770 nits was 51.6 hours.

[0177] Device Example 5: Production of a blue OLED comprising an electron buffer layer compound according to the present disclosure

[0178] The OLED was produced in the same manner as in Device Example 4, except that compound H1-212 was used as the electron buffer layer material.

[0179] The shortest time (lifetime; T95) for the produced OLED to decrease from 100% to 95% brightness at 1,770 nits is 54.5 hours.

[0180] Device Example 6: Production of a blue OLED comprising an electron buffer layer compound according to the present disclosure

[0181] The OLED was produced in the same manner as in Device Example 4, except that compound H1-213 was used as the electron buffer layer material.

[0182] The shortest time (lifetime; T95) for the produced OLED to decrease from 100% to 95% brightness at 1,770 nits is 54.5 hours.

[0183] Comparative Example 2: Production of Blue OLEDs Containing Conventional Compounds as Electron Buffer Layers

[0184] The OLED was produced in the same manner as in Device Example 4, except that compound C-1 was used as the electron buffer layer material.

[0185] The shortest time (lifetime; T95) for the produced OLED to decrease from 100% to 95% brightness at 1,770 nits is 31.6 hours.

[0186] As can be seen from Device Examples 4 to 6 and Comparative Example 2, OLEDs using the organic electroluminescent compound according to the present disclosure as the electron buffer layer material exhibit improved lifetime characteristics. Specifically, the lifetime characteristics of blue organic electroluminescent devices can be improved by including the compound of the present disclosure. Therefore, blue organic electroluminescent devices can also exhibit comparable performance, maintaining a balance with the lifetime characteristics of red and green organic electroluminescent devices, and are thus expected to be suitable for various fields and displays.

[0187] The compounds used in the apparatus examples and comparative examples are shown in Table 2.

[0188] [Table 2]

[0189]

Claims

1. A plurality of host materials, comprising a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2, wherein the compound represented by Formula 1 and the compound represented by Formula 2 are different from each other: ----- (1) In Equation 1, HAr represents an unsubstituted or at least substituted triazine group selected from the group consisting of 3- to 30-membered heteroaryl and C6-C30 aryl; L1 represents a deuterated or unsubstituted phenylene, a deuterated or unsubstituted biphenylene, or a deuterated or unsubstituted naphthylene; R1 to R4 each independently represent hydrogen or deuterium; at least one of groups R5 and R6, R6 and R7, and R7 and R8 is associated with the following formula 1-a. Fusing to form one or more rings, ----- (1-a) In equation 1-a, Y1 represents O or S. R9 to R 12 Each can be used independently to represent hydrogen or deuterium. Dn represents n hydrogen atoms being replaced by deuterium; and n represents an integer from 1 to 50; R5 to R8, which do not form rings, each independently represent hydrogen or deuterium; ----- (2) In Equation 2, A1 and A2 each independently represent deuterated or unsubstituted C6-C30 aryl groups, where, The C6-C30 aryl groups are selected from the group consisting of: phenyl, biphenyl, terphenyl, naphthyl, and naphthylphenyl. L 11 Represents C6-C30 arylene groups with single bonds, or deuterated or unsubstituted groups; X', X", X 11 To X 14 and X 23 To X 26 Each can be used independently to represent hydrogen or deuterium; m and n each independently represent integers from 1 to 3; and If m and n are integers of 2 or greater, then each X' and each X'' can be the same or different.

2. The various main body materials according to claim 1, wherein, Equation 1 is represented by at least one of the following equations 1-1 to 1-6: ----- (1-1) ----- (1-2) ----- (1-3) ----- (1-4) ----- (1-5) ----- (1-6) In equations 1-1 to 1-6, R1 to R 12 Y1, L1, HAr, and Dn are as defined in claim 1.

3. The various main body materials according to claim 1, wherein, L1 in Equation 1 is represented by any one of the following groups: In the above formula, X i To X p Each can be used independently to represent hydrogen or deuterium.

4. The various main body materials according to claim 1, wherein, Equation 2 is represented by at least one of the following equations 2-1 to 2-8: --- (2-1) --- (2-2) --- (2-3) --- (2-4) --- (2-5) --- (2-6) --- (2-7) --- (2-8) In equations 2-1 to 2-8, A1, A2, X 11 To X 14 and X 23 To X 26 It is as defined in claim 1; and X 15 To X 22 Each is independently identical to the definition of X' in claim 1.

5. The various main body materials according to claim 1, wherein, In Formula 2, A1 and A2 are each independently a deuterated or unsubstituted phenyl or a deuterated or unsubstituted biphenyl.

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

7. The various main body materials according to claim 1, wherein, The compound represented by Formula 2 is selected from at least one of the following compounds: 。

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