Composition materials for organic electroluminescent devices, a plurality of host materials, and organic electroluminescent devices comprising the same

Abstract

This disclosure relates to a compositional material for an organic electroluminescent device, various host materials, and an organic electroluminescent device comprising the same. By including a compositional material for an organic electroluminescent device comprising a specific combination of compounds, organic electroluminescent devices with high luminous efficiency and / or long lifetime characteristics can be produced.

Description

Technical Field

[0001] This disclosure relates to a compositional material for an organic electroluminescent device, various host materials, and an organic electroluminescent device comprising the same. Background Technology

[0002] Small-molecule green organic electroluminescent devices (OLEDs) were first developed in 1987 by Tang et al. of Eastman Kodak using a TPD / ALq3 bilayer consisting of a light-emitting 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 displays, OLEDs with high luminous efficiency and / or long lifetime characteristics are required.

[0003] US Patent No. 6,902,831 discloses azulene derivatives as organic electroluminescent compounds, and Korean Patent Application Publications Nos. 2016-0022784 and 2017-0001563 disclose an organic electroluminescent device comprising carbazole derivatives and compounds having a carbazole-carbazole structure as multiple host compounds. However, there is still a need to develop methods to improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] Technical issues

[0005] The purpose of this disclosure is to provide an organic electroluminescent device with high luminous efficiency and / or long lifetime characteristics by means of a compositional material comprising a specific combination of compounds for an organic electroluminescent compound.

[0006] Solution to the problem

[0007] The inventors of this invention have discovered that the above-mentioned objective can be achieved by a compositional material for an organic electroluminescent device comprising a compound represented by Formula 1 and a compound represented by Formula 2:

[0008]

[0009] in

[0010] M represents NL-(Ar) a S or O;

[0011] L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0012] Ar 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 mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;

[0013] Y1 to Y 12 Each can be represented independently as N or CR1;

[0014] R1 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)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent R1s may be fused together to form a substituted or unsubstituted ring; and

[0015] a represents an integer from 1 to 4, where if a is an integer of 2 or greater, each Ar can be the same or different;

[0016]

[0017] in

[0018] Ar1 represents substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl;

[0019] L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0020] X1 to X8 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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, -NR5R6, or -SiR7R8R9; or may be fused with adjacent X1 to X8 to form a ring, provided that none of X1 to X8 is a substituted or unsubstituted carbazole group; and

[0021] R5 to R9 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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- to 30-membered) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be fused with adjacent R5 to R9 to form a ring.

[0022] Beneficial effects of the present invention

[0023] By using the compositional materials for organic electroluminescent devices according to the present disclosure, organic electroluminescent devices with high luminous efficiency and / or long lifetime characteristics can be produced. Detailed Implementation

[0024] 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.

[0025] The term "composition material for an organic electroluminescent device" in this disclosure means that at least two materials that can be used in an organic electroluminescent device are present together or are prepared to be present together. In this document, "present together" means not only that the at least two materials are mixed but also that the at least two materials are separate from each other. Furthermore, the concept of composition material for an organic electroluminescent device encompasses materials included before (e.g., before vapor deposition) and after (e.g., after vapor deposition) the organic electroluminescent device. For example, composition material for an organic electroluminescent device may include at least two of hole injection materials, hole transport materials, hole assist materials, luminescence assist materials, electron blocking materials, luminescent materials (host materials and / or dopant materials), electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. The compositional material for an organic electroluminescent device may comprise at least two hole injection materials, at least two hole transport materials, at least two hole assist materials, at least two light-emitting assist materials, at least two electron blocking materials, at least two light-emitting materials (host material and / or dopant material), at least two electron buffer materials, at least two hole blocking materials, at least two electron transport materials, and / or at least two electron transport materials. The compositional material for an organic electroluminescent device disclosed herein may be contained in any layer constituting the organic electroluminescent device. The at least two materials contained in the compositional material may be contained together in one layer or may be contained separately in different layers. When at least two materials are contained in one layer, they may be mixed and evaporated to form a layer, or they may be co-evaporated separately and simultaneously to form a layer.

[0026] 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. For example, the multiple host materials of this disclosure may be a combination of at least two host materials, and may optionally further include conventional materials included in organic electroluminescent materials. Using methods known in the art, 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 compounds may be evaporated individually.

[0027] In this document, "(C1-C30)alkyl" refers 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, more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(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, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7-membered)heterocyclic alkyl" refers to a cycloalkyl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably selected from the group consisting of O, S, and N, and 3 to 7 cyclic skeleton atoms, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. "(C6-C30)(aryl)" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, and may be partially saturated. The number of ring skeleton carbon atoms is preferably 6 to 20, more preferably 6 to 15, and includes phenyl, biphenyl, terphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, phenylphenanthryl, anthracene, indene, triphenylene, pyrene, tetraphenyl, perylene, etc. Aryl, naphthyl, fluoranthyl, spirodifluorenyl, azuleyl, etc. More specifically, the above-mentioned aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, benzanthyl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, naphthyl, pyrene, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Trimethylene, 2-Trimethylene, 3-Trimethylene, 4-Trimethylene, 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl, 9-Fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, 2-Biphenyl, 3-Biphenyl, 4-Biphenyl, o-Triphenyl, m-Triphenyl-4-yl, m-Triphenyl-3-yl, m-Triphenyl-2-yl, p-Triphenyl-4-yl, p-Triphenyl-3-yl, p-Triphenyl-2-yl, m-Tetraphenyl, 3-Fluoranthryl, 4-Fluoranthryl, 8-Fluoranthryl, 9-Fluoranthryl, benzo[a]fluoranyl, o-Tolyl, m-Tolyl, p-Tolyl, 2,3-Xylyl, 3,4-Xylyl, 2,5-Xylyl, Trimethylyl, o-Isopropylphenyl, m-Isopropylphenyl, p-Isopropylphenyl, p-Tertiaryl Butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4'-tert-butyl-p-terphenyl-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, etc. "(3- to 50-membered) (hybrid)aryl" means an aryl group having at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 3 to 50 ring skeleton atoms; wherein the number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20; and can be It is a monocyclic or fused ring condensed with at least one benzene ring; it may be partially saturated; it may be a (sub)heteroaryl formed by linking at least one heteroaryl or aryl to a heteroaryl via one or more single bonds; and it includes monocyclic heteroaryl, including furanyl, thiophene, pyrrole, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazonyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and fused-ring heteroaryl, including benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophene, benzonaphthothiophene, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxoxazolyl, benzoxoxazolyl, etc. Azolyl, isoindolyl, indolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxazinyl, carbazole, quinoxazinyl, phenanthridine, benzodioxanepentenyl, etc. More specifically, the above heteroaryl groups may include 1-pyrroleyl, 2-pyrroleyl, 3-pyrroleyl, pyrazinyl, 2-pyridinyl, 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-indololinyl, 2-indololinyl, 3-indololinyl, 5-indololinyl, 6-indololinyl, 7-indololinyl, etc.8-Indololinyl, 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-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furanyl, 3-Furanyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 7-Benzofuranyl, 1-Isobenzofuranyl, 3-Isobenzofuranyl, 4 -Isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-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-carbazoleyl, azacarbazoleyl-1-yl, azacarbazoleyl-2-yl, azacarbazoleyl-3-yl, azacarbazoleyl-4-yl, azacarbazoleyl-5-yl, azacarbazoleyl-6-yl, azacarbazoleyl- 7-yl, azacarbazolyl-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, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silylfluorenyl (1-silafluorenylgroup), 2-silylfluorenyl, 3-silylfluorenyl, 4-silylfluorenyl,1-Germanium fluorenyl group, 2-germanium fluorenyl, 3-germanium fluorenyl, and 4-germanium fluorenyl. "Halogens" include F, Cl, Br, and I.

[0028] 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.

[0029] In this text, "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Ar, L, R1 to R9, R 16The substituents of the substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (aryl), substituted (heteroaryl), substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono- or dialkylamino, substituted mono- or diarylamino, and substituted alkylarylamino 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; (3- to 7-membered)heterocyclic alkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or substituted with (C1-C30)alkyl, (C6-C30)aryl and / or di(C6-C30)aryl Amino-substituted (3- to 50-membered) heteroaryl; unsubstituted or (C6-C30) aryl substituted with cyano, (3- to 50-membered) heteroaryl and / or tri(C6-C30)arylsilyl; 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-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. Preferably, the substituent may be at least one selected from the group consisting of: (C1-C20)alkyl; unsubstituted or (C6-C25)aryl substituted with (C1-C20)alkyl and / or (3- to 30-membered)heteroaryl; unsubstituted or (C1-C20)aryl substituted with (C6-C25)aryl (3- to 40-membered)heteroaryl and di(C6-C20)arylamino.For example, the substituent may be methyl; tert-butyl; unsubstituted or substituted phenyl groups, or substituted with pyridyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinoxalinyl, biphenylquinoxalinyl, dibenzofuranyl and / or dibenzothiopheneyl; unsubstituted or substituted naphthyl groups, or substituted with diphenyltriazinyl; biphenyl; naphthylphenyl; terphenyl; dimethylfluorenyl; phenylfluorenyl; diphenylfluorenyl; phenanthreneyl; benzophenanthreneyl; pyridyl; triazinyl group substituted with at least one of phenyl and naphthyl; or substituted with diphenyl... Substituted indolyl; benzimidazole substituted with phenyl; quinolinyl; quinazolinyl substituted with phenyl and / or biphenyl; quinoxalinyl substituted with phenyl; unsubstituted or phenyl-substituted carbazolyl; dibenzofuranyl; dibenzothiopheneyl; unsubstituted or phenyl-substituted benzocarbazolyl; dibenzocarbazolyl; benzophenanthrenethiopheneyl; diphenylamino; dimethylfluorenylphenylamino; or substituted or unsubstituted (16- to 33-membered) heteroaryl groups containing at least one of nitrogen, oxygen, or sulfur.

[0030] In the formulas of this disclosure, if adjacent substituents are connected or fused to form a substituted or unsubstituted (3-membered to 30-membered) ring, the ring may be monocyclic or polycyclic, alicyclic or aromatic, or a combination thereof, wherein the ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur. For example, the ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.

[0031] In the formula disclosed herein, each (hetero)aryl group may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be associated with at least one combination 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-membered 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)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0032] In Equation 1 above, M represents NL-(Ar). a S or O.

[0033] In Formula 1 above, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 18-membered) heteroarylene, wherein the heteroarylene may contain at least one of nitrogen, oxygen, and sulfur. According to embodiments of this disclosure, in Formula 1, L can represent a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted pyrimidinylene, a substituted or unsubstituted triazineylene, a substituted or unsubstituted quinazolinylene, a substituted or unsubstituted quinoxalinylene, a substituted or unsubstituted naphthinylene, a substituted or unsubstituted benzoquinazolinylene, a substituted or unsubstituted benzothiophenepyrimidinylene, a substituted or unsubstituted acenaphthylpyrimidinylene, or a substituted or unsubstituted (13- to 16-membered) heteroaryl group containing at least one of nitrogen, oxygen, and sulfur.

[0034] In Formula 1 above, Ar 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 mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl. The aryl(C6-C30) arylamino group; preferably, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5- to 30-membered) heteroaryl, or a substituted or unsubstituted di(C6-C25) arylamino group; and more preferably, a substituted or unsubstituted (C6-C18) aryl, a substituted or unsubstituted (5- to 25-membered) heteroaryl, or a substituted or unsubstituted di(C6-C18) arylamino group.

[0035] According to embodiments of this disclosure, in Formula 1, Ar can represent substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triazine, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted carbazole, substituted or unsubstituted Substituted dibenzothiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted benzofuran, substituted or unsubstituted naphridyl, substituted or unsubstituted benzothiophene-pyrimidinyl, substituted or unsubstituted benzothiophene-quinolinyl, substituted or unsubstituted benzofuran-quinolinyl, substituted or unsubstituted triindenyl, substituted or unsubstituted phenanthimidazole, substituted or unsubstituted (9- to 25-membered) heteroaryl containing at least one of nitrogen, oxygen and sulfur, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted diphenylamino, substituted or unsubstituted fluorenylphenylamino, or substituted or unsubstituted fluorenylbiphenylamino.

[0036] In Equation 1 above, a represents an integer from 1 to 4, preferably 1 or 2. If a is an integer of 2 or greater, then each Ar can be the same or different.

[0037] In Equation 1 above, Y1 to Y 12 Each of them independently represents N or CR1. According to embodiments of this disclosure, Y1 to Y 12 All can represent CR1. According to another embodiment of this disclosure, Y1 to Y 12 At least one of them can represent N.

[0038] In this document, R1 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)arylmethyl Silyl, substituted or unsubstituted (C1-C30)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent R1s may be fused together to form a substituted or unsubstituted ring. Preferably, R1 represents hydrogen, a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5- to 25-membered) heteroaryl, or a substituted or unsubstituted di(C6-C25) arylamino; or adjacent R1s may be fused together to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C25) aromatic ring, wherein at least one carbon atom in the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. More preferably, R1 represents hydrogen, a substituted or unsubstituted (C1-C10) alkyl, a substituted or unsubstituted (C6-C18) aryl, a substituted or unsubstituted (5- to 18-membered) heteroaryl, or a substituted or unsubstituted di(C6-C18) arylamino; or adjacent R1s may be fused together to form a substituted or unsubstituted, monocyclic or polycyclic (C5-C18) aromatic ring, wherein at least one carbon atom in the formed aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. According to embodiments of this disclosure, R1 may represent hydrogen, a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted phenylbiphenylamino, etc.

[0039] According to embodiments of this disclosure, in Formula 1, Y1 to Y... 12 At least one adjacent pair in the equation represents CR1, and the R1 of two adjacent CR1s fused together to independently form a ring represented by any one of equations 1-11 to 1-15 below, but not limited thereto. In this document, Y1 and Y2, R5 and Y6, and Y9 and Y 10They are also considered to be adjacent to each other. For example, the formed rings can be substituted or unsubstituted benzene rings, naphthyl rings, furan rings, thiophene rings, substituted or unsubstituted pyrrole rings, pyridine rings, benzofuran rings, benzothiophene rings, substituted or unsubstituted indole rings, dibenzofuran rings, dibenzothiophene rings, substituted or unsubstituted carbazole rings, or phenanthrene rings, including rings represented by formulas 1-11 to 1-15.

[0040]

[0041] In equations 1-11 to 1-15 above, The fusion sites of C and R1 in adjacent CR1 in Equation 1.

[0042] In formulas 1-13 to 1-15 above, X represents N or CR4. According to embodiments of this disclosure, all X can be CR4. According to another embodiment of this disclosure, at least one X can be N. R4 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, or substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl. Alkyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; preferably, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; and more preferably, substituted or unsubstituted (C6-C18)aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl.

[0043] In formulas 1-14 above, R3 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. Silyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; preferably, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; and more preferably, substituted or unsubstituted (C6-C18)aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl; for example, phenyl.

[0044] The compound represented by Formula 1 can be represented by Formula 1-1 or 1-2.

[0045]

[0046] In equations 1-1 and 1-2 above, M and Y2 to Y 12 As defined in Equation 1, and Y 13 and Y 14 Each is independent as defined for Y2.

[0047] In Formula 1-1 above, Y1 represents N or CR2, where R2 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) alkylsilyl, etc. 1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0048] In Formula 2 above, A1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-membered to 30-membered) heteroaryl group; preferably, an unsubstituted (C6-C25) aryl group, or an unsubstituted or (C6-C30) substituted (5-membered to 25-membered) heteroaryl group; and more preferably, an unsubstituted (C6-C18) aryl group, or an unsubstituted or (C6-C18) substituted (5-membered to 18-membered) heteroaryl group. For example, A1 can represent phenyl; naphthyl; biphenyl; terphenyl; a triazine group substituted with at least one of phenyl, naphthyl, and biphenyl; diphenylpyridyl; phenylquinoline; phenylquinoxaloline; phenylquinazoline; diphenylquinazoline; a quinazoline group substituted with phenylcarbazole; dibenzofuranyl; dibenzothiopheneyl; or phenylcarbazoleyl.

[0049] In Formula 2 above, L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; preferably, a single bond, an unsubstituted (C6-C25) arylene, or an unsubstituted (5- to 25-membered) heteroarylene; and more preferably, a single bond, an unsubstituted (C6-C18) arylene, or an unsubstituted (5- to 18-membered) heteroarylene. For example, L1 can represent a single bond, phenylene, naphthylene, biphenylene, quinoline, quinoxalinyl, quinoxalinyl, or carbazoline.

[0050] In Formula 2 above, X1 to X8 independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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, -N R5R6, or -SiR7R8R9; or may be fused with adjacent X1 to X8 to form a ring; preferably, hydrogen, unsubstituted (C6-C25) aryl, or unsubstituted (5-membered to 25-membered) heteroaryl; or may be fused with adjacent X1 to X8 to form a ring; and more preferably, hydrogen, unsubstituted (C6-C18) aryl, or unsubstituted (5-membered to 18-membered) heteroaryl; or may be fused with adjacent X1 to X8 to form a ring. However, none of X1 to X8 is a substituted or unsubstituted carbazole group. For example, X1 to X8 may each independently represent hydrogen, phenyl, dibenzofuranyl or dibenzothiophene, or may be fused with adjacent X1 to X8 to form a benzene ring, a substituted indole ring, a benzothiophene ring, a benzofuran ring, a substituted benzoindole ring, a naphthofuran ring, a naphthothiophene ring or an aza-azo ring. The substituent of the substituted indole ring may be selected from at least one of the following: unsubstituted phenyl or substituted with phenyltriazinyl, phenylquinoxalinyl, phenylquinoxalinyl, biphenylquinoxalinyl, dibenzofuranyl and / or dibenzothiopheneyl; unsubstituted naphthylphenyl; unsubstituted biphenyl; unsubstituted terphenyl; phenyl-substituted quinoxalinyl; phenyl-substituted quinoxalinyl; and naphthyl substituted with diphenyltriazinyl. The substituent of the substituted benzoindole ring may be selected from at least one of the following: unsubstituted phenyl or substituted with benzofuranyl or dibenzothiopheneyl; naphthylphenyl; biphenyl; and dibenzofuranyl.

[0051] In Formula 2 above, R5 to R9 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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 fused with adjacent R5 to R9 to form a ring.

[0052] The compound represented by formula 2 can be represented by any one of the following formulas 2-1 to 2-8.

[0053]

[0054] In equations 2-1 to 2-8 above, A1, L1, and X1 to X4 are as defined in equation 2; X9 to X 38 Each is independently defined as for X1; b, e, f, g, h, and l each independently represent 1 or 2; c, d, and i each independently represent integers from 1 to 3; j and k each independently represent integers from 1 to 4; where if b to l are integers of 2 or greater, X9, X 14 X 19 X 20 X 21 X 30 X 31 and X 35 To X 38 Each of them can be the same or different. In Equation 2-2 above, Z represents O or S.

[0055] In equations 2-1 and 2-4 to 2-6 above, V and W independently represent single bonds and NR. 16 O or S, provided that V and W are not both single bonds, and that V and W are not both NR bonds. 16 According to embodiments of this disclosure, one of V and W can represent a single bond, and the other can represent NR. 16 、O or S.

[0056] R 16 The term represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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; preferably, unsubstituted or substituted (3- to 30-membered) heteroaryl (C6-C25) aryl, or unsubstituted or substituted (C6-C30) aryl (5- to 25-membered) heteroaryl; and more preferably, unsubstituted or substituted (5- to 25-membered) heteroaryl (C6-C18) aryl, or unsubstituted or substituted (C6-C18) aryl (5- to 18-membered) heteroaryl. For example, R 16 It can represent an unsubstituted or substituted phenyl group, or a phenyl quinoxalinyl, phenyl quinoxalinyl, biphenyl quinoxalinyl, dibenzothiopheneyl and / or dibenzofuranyl; a naphthyl group substituted with a diphenyl triazinyl; a biphenyl; a terphenyl; a naphthylphenyl; a quinoxalinyl group substituted with a phenyl; or a quinoxalinyl group substituted with a phenyl.

[0057] In equations 2-1 to 2-8 above, X1 to X4 and X9 to X... 38 Each of the elements preferably represents hydrogen or an unsubstituted (C6-C25) aryl group independently; or may be associated with adjacent elements X1 to X4 and X9 to X. 38 Fusing to form a ring; more preferably, representing hydrogen or an unsubstituted (C6-C18) aryl group; or may be fused with adjacent X1 to X4 and X9 to X 38 Fusing together to form rings. For example, X1 to X4 and X9 to X 30 Each can independently represent hydrogen or phenyl; X 31 To X 38 It can represent hydrogen; X1 and X2, X3 and X4, and two adjacent X's. 21 They can independently fuse together to form either a phenyl-substituted indole ring or an unsubstituted benzene ring.

[0058] The compound represented by Formula 1 may be selected from at least one of the following compounds, but is not limited thereto.

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] The compound represented by Formula 2 may be selected from at least one of the following compounds, but is not limited thereto.

[0086]

[0087]

[0088]

[0089]

[0090] The compounds represented by Formula 1 according to this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, they can be prepared according to the following reaction scheme.

[0091] [Reaction Scheme 1]

[0092]

[0093] [Reaction Scheme 2]

[0094]

[0095] [Reaction Scheme 3]

[0096]

[0097] [Reaction Scheme 4]

[0098]

[0099] [Reaction Scheme 5]

[0100]

[0101] [Reaction Scheme 6]

[0102]

[0103] In reaction schemes 1 to 6, L, Ar, Y1 to Y 12 And a is as defined in Equation 1.

[0104] The compound represented by Formula 2 of this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared by referring to Korean Patent Application Publication Nos. 2015-0135109 (published December 2, 2015), 2015-0032447 (published March 26, 2015), 2016-0099471 (published August 22, 2016) and 2018-0012709 (published February 6, 2018), but is not limited thereto.

[0105] Furthermore, the compositional material for organic electroluminescent devices disclosed herein can be a variety of host materials, wherein the compound represented by Formula 1 can be a first host material and the compound represented by Formula 2 can be a second host material. The compositional material for organic electroluminescent devices disclosed herein can consist solely of the first host material represented by Formula 1 and the second host material represented by Formula 2, or may further include conventional materials contained in the host materials. The compositional material for organic electroluminescent devices disclosed herein may contain the compound represented by Formula 1 and the compound represented by Formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and 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 in desired amounts by placing them in an oscillator and then mixing them, by dissolving them in a glass tube by means of heating and then collecting the result, or by dissolving them in a solvent, etc. According to embodiments of this disclosure, organic electroluminescent materials comprising a variety of host materials of this disclosure are provided.

[0106] Furthermore, an organic electroluminescent device comprising the compounds represented by Formula 1 and Formula 2 of this disclosure can be provided. Specifically, the organic electroluminescent device of this disclosure may include at least one light-emitting layer between an anode and a cathode, wherein the light-emitting layer may comprise a host and a dopant, and the host may comprise the compositional material of the organic electroluminescent device of this disclosure. The organic electroluminescent device of this disclosure may comprise a compound represented by Formula 1 as a first host material and a compound represented by Formula 2 as a second host material.

[0107] In this document, the light-emitting layer is the layer from which light is emitted, and can be a single layer or a multilayer in which two or more layers are stacked. According to embodiments of this disclosure, the doping concentration of the dopant compound in the light-emitting layer relative to the host compound can be less than 20 wt%.

[0108] The organic electroluminescent device disclosed herein may further include at least one layer selected from the following: hole injection layer, hole transport layer, hole auxiliary layer, light emission auxiliary layer, electron transport layer, electron injection layer, intermediate layer, electron buffer layer, hole blocking layer, and electron blocking layer.

[0109] The dopant included in the organic electroluminescent device of this disclosure is at least one phosphorescent dopant or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but may 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.

[0110] The dopants included in the organic electroluminescent device according to the present disclosure may include, but are not limited to, compounds represented by formula 101.

[0111]

[0112] In Equation 101, L is selected from the following structures 1 to 3:

[0113]

[0114] R 100 To R 103 Each can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (C3-C30) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be associated with adjacent R. 100 To R 103 Linked to form substituted or unsubstituted fused rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenepyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenequinoline;

[0115] R 104 To R 107 Each can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be combined with the adjacent R 104 To R 107Linked to form substituted or unsubstituted fused rings, such as substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothiophenopyridine;

[0116] R 201 To R 220 Each can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be combined with adjacent R 201 To R 220 Connect to form substituted or unsubstituted fused rings; and

[0117] n represents an integer from 1 to 3.

[0118] Specifically, the dopant compounds include, but are not limited to, the following compounds.

[0119]

[0120]

[0121]

[0122]

[0123] The organic electroluminescent device according to this disclosure includes a first electrode; a second electrode; and at least one organic layer between the first electrode and the second electrode.

[0124] One of the first and second electrodes can be an anode, and the other can be a cathode. The organic layer includes a light-emitting layer and may further include at least one layer selected from the following: 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 layer may further consist of multiple layers.

[0125] The first and second electrodes can be formed of transmissive conductive materials, semi-transmissive reflective conductive materials, or reflective conductive materials, respectively. Depending on the types of materials used to form the first and second electrodes, 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 a p-type dopant, and the electron injection layer can be further doped with an n-type dopant.

[0126] The organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0127] Furthermore, in the organic electroluminescent device according to this disclosure, 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.

[0128] Furthermore, the organic electroluminescent device according to this disclosure can emit white light by further including at least one light-emitting layer, said light-emitting layer comprising, in addition to the compounds according to this disclosure, blue, red, or green electroluminescent compounds known in the art. Furthermore, if desired, it can further include a yellow or orange light-emitting layer.

[0129] In the organic electroluminescent device according to this disclosure, at least one layer (hereinafter, "surface layer") is preferably disposed on one or more inner surfaces of one or two electrodes; selected from chalcogenide layers, metal halide layers, and metal oxide layers. Specifically, a silicon or aluminum chalcogenide (including oxide) layer is preferably disposed on the anode surface of the electroluminescent dielectric layer, and the metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent dielectric layer. This surface layer provides operational stability to the organic electroluminescent device. Preferably, the chalcogenide comprises SiO₂. X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; the metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and the metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0130] 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.

[0131] 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.

[0132] 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 block 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. Hole auxiliary layers and electron blocking layers can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0133] In the organic electroluminescent device according to 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 fabricate an organic electroluminescent device having two or more light-emitting layers that emit white light.

[0134] The organic electroluminescent materials according to embodiments of this disclosure can be used as luminescent materials for white organic light-emitting devices. Various structures for white organic light-emitting devices have been proposed, such as parallel arrangement (side-by-side) methods, stacking methods, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) luminescent units. Furthermore, the organic electroluminescent materials according to embodiments of this disclosure can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0135] To form each layer constituting the organic electroluminescent device of this disclosure, dry film formation methods such as vacuum deposition, sputtering, plasma, ion plating, etc., or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0136] When using a wet film-forming method, a thin film is formed by dissolving or dispersing the materials constituting each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent is not particularly limited, as long as it is soluble or dispersible in a solvent in which the materials constituting each layer have no problem with film-forming ability.

[0137] This disclosure allows the provision of display devices using compositional materials for organic electroluminescent devices comprising compounds represented by Formula 1 and compounds represented by Formula 2. In other words, the compositional materials for organic electroluminescent devices disclosed herein can be used to manufacture display systems or lighting systems. Specifically, display systems, such as those for smartphones, tablets, laptops, PCs, TVs, or automobiles, can be manufactured using the compositional materials for organic electroluminescent devices disclosed herein; or lighting systems, such as outdoor or indoor lighting systems.

[0138] The following will explain the improved luminous efficiency and lifetime characteristics of OLED devices by incorporating the compositional materials for organic electroluminescent devices of this disclosure. However, the following examples are intended to illustrate the characteristics of OLED devices incorporating the compositional materials for organic electroluminescent devices of this disclosure, and this disclosure is not limited to the following examples.

[0139] Device Examples 1 to 18: Production of OLED devices comprising compositional materials for OLED devices according to the present disclosure Produce

[0140] An OLED device comprising the compositional material for an organic light-emitting diode (OLED) device according to the present disclosure is produced. A transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geomatec, Japan) on a glass substrate for the OLED device is sequentially ultrasonically washed with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. Next, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 is introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure within the chamber is controlled to 10 Ω / sq. -6The process involves applying a current to a chamber to evaporate the introduced material, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Then, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and by applying a current to the chamber, the compound is evaporated, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and by applying a current to the chamber, the compound is evaporated, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and by applying a current to the chamber, the compound is evaporated, 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, a light-emitting layer is deposited as follows. The first and second host compounds shown in Table 1 below are introduced as hosts into one chamber of the vacuum vapor deposition apparatus, and compound D-39 is introduced into the other chamber. Two host materials were evaporated at a 1:1 ratio, while dopant materials were evaporated simultaneously at different rates. These were then deposited with a doping amount of 3 wt% based on the total amount of host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. Compounds ET-1 and EI-1 were then introduced into two separate chambers, evaporated at a 1:1 ratio, and deposited to form a 35 nm thick electron transport layer on the light-emitting layer. Next, 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. This produced an OLED device.

[0141] Comparative Example 1: Production of OLED Devices Containing Conventional Compounds

[0142] The OLED device was produced in the same manner as in Device Example 1, except that compound A was used as the second host compound.

[0143] Table 1 below provides the luminous efficacy of the manufactured OLED device at a brightness of 5,000 nits, as well as the time (lifetime; T95) it takes for the brightness to decrease from 100% to 95% at a constant current and a brightness of 5,000 nits.

[0144] [Table 1]

[0145]

[0146] As can be seen from Table 1 above, compared with organic electroluminescent devices containing conventional organic electroluminescent compounds, organic electroluminescent devices containing compounds represented by Formulas 1 and 2 of this disclosure as the main body exhibit higher luminous efficiency and longer lifetime characteristics. By using the compositional materials for organic electroluminescent devices disclosed herein, both the luminous efficiency and lifetime characteristics in organic electroluminescent devices, which are mutually conflicting, can be improved.

[0147] The compounds used in the apparatus examples and comparative examples are shown in Table 2 below.

[0148] [Table 2]

[0149]

[0150]

Claims

1. A composition material for an organic electroluminescent device, the composition material comprising a compound represented by the following formula 1-2 and a compound represented by the following formula 2-6 or 2-8: wherein L represents a single bond, or a substituted or unsubstituted phenylene, wherein the substituent of the substituted phenylene is selected from the group consisting of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl; Ar represents a substituted or unsubstituted (3- to 30-membered)heteroaryl, and is selected from the group consisting of a substituted triazinyl, a substituted quinazolinyl, a substituted quinoxalinyl, wherein the substituent of the substituted triazinyl is selected from a substituted or unsubstituted phenyl; wherein the substituent of the substituted quinazolinyl and the substituted quinoxalinyl is selected from deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, and a substituted or unsubstituted phenyl; wherein the substituent of the substituted phenyl is selected from deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl; R 1 represents hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, or t-butyl; and a represents 1; wherein in the formula 2-6, A 1 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted dibenzofuranyl; L 1 represents a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene; wherein the substituent of the substituted phenyl, the substituted biphenyl, the substituted dibenzofuranyl, the substituted phenylene, and the substituted biphenylene is selected from the group consisting of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl; in the formula 2-8, A 1 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl; L 1 represents a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene; wherein the substituent of the substituted phenyl, the substituted biphenyl, the substituted terphenyl, the substituted phenylene, and the substituted biphenylene is selected from the group consisting of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl; the substituted triazinyl is substituted with two phenyl groups. 2.The composition material for an organic electroluminescent device according to claim 1, wherein the compound represented by the formula 1-2 is at least one selected from the group consisting of: M represents N-L-(Ar) a ; 3.The composition material for an organic electroluminescent device according to claim 1, wherein the compound represented by the formula 2-6 or 2-8 is at least one selected from the group consisting of: 4.The composition material for an organic electroluminescent device according to claim 1, wherein the compound represented by the formula 1-2 is at least one selected from the group consisting of: Y3to Y 14 each independently represents CR1; 5.The composition material for an organic electroluminescent device according to claim 1, wherein the compound represented by the formula 2-6 or 2-8 is at least one selected from the group consisting of: 6.The composition material for an organic electroluminescent device according to claim 1, wherein the first host material comprises the compound represented by the formula 1-2 as claimed in claim 1, and the second host material comprises the compound represented by the formula 2-6 or 2-8 as claimed in claim 1. 7.An organic electroluminescent device comprising the composition material for an organic electroluminescent device as claimed in claim 1. ​ ​ X1to X4, X9, X 30 to X 38 each independently represents hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl; b, g and l each independently represent 1 or 2; i represents an integer of 1 to 3; j and k each independently represent an integer of 1 to 4; wherein if b, g, i, j, k and l are an integer of 2 or more, each of X9, X 30 , X 31 and X 35 to X 38 may be the same or different; V and W each independently represent a single bond or NR 16 , with the proviso that both V and W are not a single bond at the same time, and both V and W are not NR 16 ; and R 16 represents substituted or unsubstituted phenyl, wherein the substituents of the substituted phenyl are selected from the group consisting of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl.

2. The composition material for an organic electroluminescent device according to claim 1, wherein ​ 3. The composition material for an organic electroluminescent device according to claim 1, wherein ​ 4. The composition material for an organic electroluminescent device according to claim 1, wherein ​ 5. The composition material for an organic electroluminescent device according to claim 1, wherein ​ 6. A plurality of host materials comprising a first host material and a second host material, wherein, ​ ​

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