Multiple host materials and organic electroluminescent devices containing them

Abstract

The present invention provides multiple host materials and an organic electroluminescent device containing them. [Solution] This disclosure relates to a plurality of host materials, each comprising a first host material containing a compound represented by formula 1 and a second host material containing a compound represented by formula 2, and an organic electroluminescent device comprising the same. By including specific combinations of compounds as host materials, it is possible to provide an organic electroluminescent device having a lower drive voltage and / or higher luminescence efficiency and / or longer lifespan compared to conventional organic electroluminescent devices.

Description

[Technical Field]

[0001] This disclosure relates to a plurality of host materials and an organic electroluminescent device containing them. [Background technology]

[0002] The green-emitting TPD / Alq3 bilayer small molecule organic electroluminescent device (OLED), consisting of a light-emitting layer and a charge transport layer, was first developed in 1987 by Tang et al. at Eastman Kodak. Since then, OLED research has been rapidly commercialized.

[0003] The most important factor determining the luminescence efficiency in OLEDs is the luminescent material. To date, iridium(III) complexes have been widely known as phosphorescent luminescent materials, such as bis(2-(2'-benzothienyl)-pyridinate-N,C-3')iridium(acetylacetonate)[(acac)Ir(btp)2], tris(2-phenylpyridine)iridium[Ir(ppy)3], and bis(4,6-difluorophenylpyridinate-N,C2)picolinatoiridium (Firpic), which are red, green, and blue luminescent materials, respectively.

[0004] However, while conventional materials have advantages in terms of luminescence properties, when used in OLEDs, they are unsatisfactory in terms of operating life and luminous efficiency, and improvements in high-efficiency luminescent materials for OLEDs are still needed. In particular, recently, there is a demand for OLEDs with high luminous efficiency and / or long lifespan for long-term use and high resolution in displays. [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] The object of the present disclosure is, firstly, to provide a plurality of host materials capable of manufacturing an organic electroluminescent device having a low driving voltage and / or a high luminous efficiency and / or a long lifespan, and secondly, to provide an organic electroluminescent device containing the host material.

Means for Solving the Problem

[0006] As a result of intensive studies to solve the above technical problems, the present inventors have found that a compound as an electron host material represented by the following formula (1) having a structure in which an aryl is bonded to a heteroaryl site; and a compound as a hole host material represented by the following formula (2) having a structure in which residues of an 8-membered ring are polycondensed can achieve the above-described object. As a result, the formation of excitons in the light-emitting layer is improved, and at the same time, the highest occupied molecular orbital (HOMO) barrier between the hole transport layer and the light-emitting layer is reduced, and as a result, the present invention has been completed. HAr-(L1-Ar1) a --- (1) (In the formula, HAr represents a substituted or unsubstituted nitrogen-containing (3- to 10-membered) heteroaryl; L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl; a represents an integer of 1 to 3, and when a is an integer of 2 or more, each (L1-Ar1) may be the same or different);

Chemical formula

[0007] Advantageous effects of the invention By including specific combinations of compounds as host materials according to this disclosure, it is possible to provide organic electroluminescent devices having lower drive voltage and / or higher luminous efficiency and / or longer lifespan compared to conventional organic electroluminescent devices, and to manufacture display devices or lighting devices using the same. [Modes for carrying out the invention]

[0008] This specification further describes the present disclosure. However, the following description is intended to illustrate the present invention and is not intended to limit the scope of the invention in any way.

[0009] This disclosure relates to a plurality of host materials, each comprising at least one first host material represented by Formula 1 and at least one second host material represented by Formula 2, and to an organic electroluminescent device comprising these host materials.

[0010] In this disclosure, the term "organic electroluminescent material" means a material that may contain at least one compound and can be used in an organic electroluminescent device. The organic electroluminescent material may be included in any layer constituting the organic electroluminescent device, as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emission material (containing a host and dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.

[0011] In this disclosure, the term “multiple organic electroluminescent materials” means organic electroluminescent materials comprising a combination of at least two compounds that may be included in any layer constituting an organic electroluminescent device. It may mean both the material before it is included in the organic electroluminescent device (e.g., before deposition) and the material after it is included in the organic electroluminescent device (e.g., after deposition). For example, multiple organic electroluminescent materials may be a combination of at least two compounds that may be included in at least one layer of the hole injection layer, hole transport layer, hole auxiliary layer, light emission auxiliary layer, electron blocking layer, light emission layer, electron buffer layer, hole blocking layer, electron transport layer, and electron injection layer. Such at least two compounds may be included in the same layer or different layers, may be evaporated together or simultaneously, or may be evaporated individually.

[0012] In this disclosure, the term “multiple host materials” means an organic electroluminescent material comprising a combination of at least two host materials. It may mean both the material before inclusion in the organic electroluminescent device (e.g., before deposition) and the material after inclusion in the organic electroluminescent device (e.g., after deposition). The multiple host materials of this disclosure may be included in any light-emitting layer constituting the organic electroluminescent device. Two or more compounds included in the multiple host materials of this disclosure may be included in one light-emitting layer or each may be included in different light-emitting layers. If at least two host materials are included in one layer, the at least two host materials may be mixed-deposited to form the layer, or they may be co-deposited simultaneously and individually to form the layer.

[0013] In this disclosure, the term "(C1-C30) alkyl(ene)" means a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. In this specification, the term "(C2-C30) alkenyl" means a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbuto-2-enyl. In this specification, the term "(C3-C30) cycloalkyl(ene)" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in the cyclic skeleton, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the above cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In this specification, "(C6-C30) aryl(ene)" refers to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the cyclic skeleton (where the number of carbon atoms in the cyclic skeleton is preferably 6 to 20, more preferably 6 to 15), which may be partially saturated and may contain a spiro structure. Examples of the above aryl compounds include, specifically, phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenantrenyl, phenylphenantrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perilenyl, crisenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluoren-fluoren]yl, azlenyl, etc. More specifically, aryl compounds include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl,9-Phenanthryl, Naphthacenyl, Pyrenyl, 1-Crysenyl, 2-Crysenyl, 3-Crysenyl, 4-Crysenyl, 5-Crysenyl, 6-Crysenyl, Benzo[c]phenanthryl, Benzo[g]Crysenyl, 1-Triphenylenyl, 2-Triphenylenyl, 3-Triphenylenyl, 4-Triphenylenyl, 1-Fluorenyl, 2-Fluorenyl, 3-Fluorenyl, 4-Fluorenyl, 9-Fluorenyl, Benzofluorenyl, Dibenzofluorenyl, 2-Biphenylyl, 3-Biphenylyl, 4-Biphenylyl, o-Terphenyl, m-Terphenyl-4-yl, m-Terphenyl-3-yl, m-Terphenyl-2-yl, p-Terphenyl-4-yl, p-Terphenyl-3-yl, p-Terphenyl-2-yl, m-Quaterphenyl, 3-Fluoranthenyl, These can be 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 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. In this specification, the term "(3-30 member) heteroaryl(ene)" means an aryl having 3 to 30 ring skeleton atoms, comprising at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge, wherein the number of ring skeleton atoms is preferably 3 to 30, more preferably 5 to 20. The heteroaryl or heteroarylene may be a monocyclic ring or a fused ring fused with at least one benzene ring; it may also be partially saturated. Furthermore, the heteroaryl or heteroarylene in this specification isThe heteroaryl group may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group via a single bond, and may also contain a spiro structure. Examples of heteroaryls include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetradinyl, triazolyl, tetrazolyl, flazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, etc., as well as benzofuranil, benzothiophenyl, isobenzofuranil, dibenzofuranil, benzonaphthofuranil, dibenzothio Examples of condensed ring heteroaryls include phenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthilidinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenanthridine, phenanthroxazolyl, benzodioxolyl, and others. More specifically, heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, and 8-indolidinyl. Nyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuranyl,3-benzofuranil, 4-benzofuranil, 5-benzofuranil, 6-benzofuranil, 7-benzofuranil, 1-isobenzofuranil, 3-isobenzofuranil, 4-isobenzofuranil, 5-isobenzofuranil, 6-isobenzofuranil, 7-isobenzofuranil, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl Linyl, 6-Quinoxalinyl, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolyl-1-yl, Azacarbazolyl-2-yl, Azacarbazolyl-3-yl, Azacarbazolyl-4-yl, Azacarbazolyl-5-yl, Azacarbazolyl-6-yl, Azacarbazolyl-7-yl, Azacarbazolyl-8-yl, Azacarbazolyl-9-yl, 1-Phenantridinyl, 2-Phenantridinyl, 3-Phenantridinyl, 4-Phenantridinyl, 6-Phenantridinyl, 7-Phenantridinyl Phenantridinyl, 8-phenantridinyl, 9-phenantridinyl, 10-phenantridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-flazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-tert-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolly, 4-methyl-1-indolly, 2-methyl-3-indolly, 4-methyl-3-indolly, 2-tert-butyl-1-indolly, 4-tert-butyl-1-indolly, 2-tert-butyl-3-indolly, 4-tert-butyl-3-indolly, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl,These can be 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. In this specification, the term "(C3~C30) aliphatic ring and (C6~C30) aromatic ring condensed ring" means a ring formed by condensing at least one aliphatic ring having 3 to 30, preferably 3 to 25, more preferably 3 to 18 ring skeleton carbon atoms with at least one aromatic ring having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring skeleton carbon atoms. For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane. In this specification, carbon atoms in the fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. In this specification, the term "halogen" includes F, Cl, Br, and I.

[0014] Furthermore, "ortho (o)", "meta (m)", and "para (p)" indicate the substitution positions of all substituents. The ortho position is, for example, a compound with substituents adjacent to each other at positions 1 and 2 of benzene. The meta position is the substitution position immediately following the directly adjacent substitution position, for example, a compound with substituents at positions 1 and 3 of benzene. The para position is the substitution position immediately following the meta position, for example, a compound with substituents at positions 1 and 4 of benzene.

[0015] In this specification, “ring formed by linking to adjacent substituents” means a substituted or unsubstituted (3-30 member) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof, formed by linking or condensing two or more adjacent substituents, preferably a substituted or unsubstituted (5-25 member) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. According to one embodiment of this disclosure, the number of atoms in the ring skeleton is 5-20, and according to another embodiment of this disclosure, the number of atoms in the ring skeleton is 5-15. In one embodiment, the condensed ring may be, for example, 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.

[0016] In addition, the term "substituted" in the expression "substituted or unsubstituted" as described in this disclosure means that a hydrogen atom in a particular functional group is replaced by another atom or functional group, i.e., a substituent. In the formulas of this disclosure, the substituents of substituted (C1-C30) alkyl(ene), substituted (C2-C30) alkenyl, substituted (C3-C30) cycloalkyl(ene), substituted (C3-C30) fused ring of an aliphatic ring and a (C6-C30) aromatic ring, substituted (C6-C30) aryl(ene), substituted nitrogen-containing (3-10 member) heteroaryl, and substituted (3-30 member) heteroaryl(ene) are, each independently, deuterium, halogen, cyano, carboxy, nitro, hydroxy, (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, (3~7 member)heterocycloalkyl, (C6~C30)aryloxy, (C6~C30)arylthio, unsubstituted or (C6~C30)aryl-substituted (5~30 member)heteroaryl, unsubstituted or (5~30 member)heteroaryl-substituted (C6~C30)aryl, tri(C1 ~C30) alkylsilyl, tri(C6~C30)arylsilyl, di(C1~C30)alkyl(C6~C30)arylsilyl, (C1~C30)alkyldi(C6~C30)arylsilyl, (C3~C30) condensed ring of aliphatic ring and (C6~C30) aromatic ring, amino, mono- or di-(C1~C30) alkylamino, mono- or di-(C2~C30) alkenylamino, (C1~C30) alkyl(C2~C30) alkenylamino, substituted or unsubstituted mono- or di-(C6~C30 )arylamino, (C1~C30)alkyl(C6~C30)arylamino, mono- or di-(3~30 member) heteroarylamino, (C1~C30)alkyl(3~30 member) heteroarylamino, (C2~C30)alkenyl(C6~C30)arylamino, (C2~C30)alkenyl(3~30 member) heteroarylamino, (C6~C30)aryl(3~30 member) heteroarylamino, (C1~C30)alkylcarbonyl, (C1~C30)alkoxycarbonyl,The substituent represents at least one selected from the group consisting of (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. For example, the substituent may be deuterium; methyl; unsubstituted or deuterium or naphthyl-substituted phenyl; biphenyl; naphthyl; dimethylfluorenyl; dimethylbenzofluorenyl; unsubstituted or phenyl-substituted pyridyl; dibenzofuranyl, dibenzothiophenyl; or substituted or unsubstituted carbazolyl.

[0017] In the formulas of this disclosure, each heteroaryl(ene) may independently comprise at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. Furthermore, the heteroatom may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) 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(C It may be bonded to at least one substituent selected from the group consisting of (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, and substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino.

[0018] A host material according to one embodiment will be described below.

[0019] The host material according to one embodiment comprises at least one first host compound represented by formula 1 above and at least one second host compound represented by formula 2 above, and the host material may be included in the light-emitting layer of the organic electroluminescent device according to one embodiment.

[0020] A first host material, as a host material according to one embodiment, can be represented by the following formula 1. HAr-(L1-Ar1) a --- (1)

[0021] In Equation 1, HAr represents a substituted or unsubstituted nitrogen-containing (3-10 member) heteroaryl; L1 represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar1 represents a substituted or unsubstituted (C6-C30) aryl; 'a' represents an integer between 1 and 3, and if 'a' is an integer greater than or equal to 2, then each (L1-Ar1) can be the same or different.

[0022] In one embodiment, HAr may be a substituted or unsubstituted nitrogen-containing (5-10 membered) heteroaryl, preferably an unsubstituted nitrogen-containing (6-10 membered) heteroaryl. Specifically, HAr may be a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthilidinyl, a substituted or unsubstituted triazanaphthyl, or a substituted or unsubstituted benzothienopyrimidinyl. For example, HAr may be a triazinyl, pyrimidinyl, quinolinyl, quinoxalinyl, or quinazolinyl.

[0023] In one embodiment, L1 may be a single-bonded, substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 member) heteroarylene, preferably a single-bonded, unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (5-18 member) heteroarylene. For example, L1 may be a single-bonded, unsubstituted or naphthyl-substituted phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, or a substituted or unsubstituted naphthylene.

[0024] In one embodiment, Ar1 may be a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5-25 member) heteroaryl, preferably a (C6-C18) aryl or a substituted or unsubstituted (5-18 member) heteroaryl. For example, Ar1 may be an unsubstituted or phenyl, naphthyl, or fluorenyl-substituted phenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, an unsubstituted or phenyl-substituted naphthyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted phenantrenyl, fluorenyl substituted with at least one phenyl or methyl, or benzofluorenyl substituted with at least one methyl or phenyl.

[0025] In one embodiment, a may be an integer of 2 or 3, and each of (L1-Ar1) may be the same or different.

[0026] According to one embodiment, the host material represented by formula 1 above can be represented by the following formulas 1-1 or 1-2. [ka]

[0027] In equations 1-1 and 1-2, Y1-Y6 and Z1-Z4 are each independently CR a Or it represents N, but at least one of Y1 to Y6 represents N, and at least one of Z1 to Z4 represents N; R a Each of these elements may independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, or a substituted or unsubstituted (C6-C30) aryl, or may be linked with an adjacent substituent to form a ring; L1, Ar1, and a are as defined in Equation 1.

[0028] In one embodiment, at least one of Y1 to Y6 in formula 1-1 represents N, preferably at least two of Y1 to Y6 are N, and more preferably at least three of Y1 to Y6 are N. For example, the compound represented by formula 1-1 is (L1-Ar1) a It may also be a pyrimidine or triazine in which the substituted compound is present.

[0029] In one embodiment, at least one of Z1 to Z4 in formula 1-2 represents N, and preferably at least two of Z1 to Z4 are N. For example, the compound represented by formula 1-2 is (L1-Ar1) a It may also be quinoline, quinoxaline, or quinazoline in which the substituted is present.

[0030] In one embodiment, R a All of it may be hydrogen.

[0031] According to one embodiment, the first host compound represented by the above formula 1 can be more specifically exemplified by the following compounds, but is not limited to them. [ka] [ka] [ka] [ka] [ka]

[0032] The compounds represented by Formula 1 of this disclosure can be produced by synthetic methods known to those skilled in the art. For example, the compounds represented by Formula 1-1 or 1-2 can be synthesized by referring to, but are not limited to, the following reaction schemes 1 or 2: [ka]

[0033] In reaction schemes 1 and 2, the definitions of substituents are as defined in formulas 1-1 and 1-2.

[0034] As described above, exemplary synthetic examples of compounds represented by formula 1-1 or 1-2 according to one embodiment have been described, which are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-mont-mediated etherification reactions, Miyaura boration reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclic dehydration reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions. It will be understood by those skilled in the art that the above reactions proceed even when other substituents defined by formula 1-1 or 1-2, other than those described in the specific synthetic examples, are attached.

[0035] A second host compound, which serves as another host material according to one embodiment, can be represented by the following formula 2. [ka]

[0036] In Equation 2, B1 to B7 each independently do not exist, or each independently represents a substituted or unsubstituted (C5 - C20) ring, and the carbon atoms of this ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur, provided that at least 5 of B1 to B7 are present, and the rings immediately adjacent to B1 to B7 may be fused to each other; Y represents -N - L2 - (Ar2) n , -O -, -S -, or -CR1R2; L2 represents a single bond, a substituted or unsubstituted (C1 - C30) alkylene, a substituted or unsubstituted (C6 - C30) arylene, a substituted or unsubstituted (3 - 30 - member) heteroarylene, or a substituted or unsubstituted (C3 - C30) cycloalkylene; Ar2 represents a substituted or unsubstituted (C6 - C30) aryl, a substituted or unsubstituted (3 - 30 - member) heteroaryl, or -NR3R4; R1 to R4 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1 - C30) alkyl, a substituted or unsubstituted (C2 - C30) alkenyl, a substituted or unsubstituted condensed ring of a (C3 - C30) aliphatic ring and a (C6 - C30) aromatic ring, a substituted or unsubstituted (C6 - C30) aryl, a substituted or unsubstituted (3 - 30 - member) heteroaryl, or a substituted or unsubstituted (C3 - C30) cycloalkyl, or adjacent substituents may be linked to form a ring; n represents an integer of 1 or 2, and when n is 2, each of Ar2 may be the same or different.

[0037] In one embodiment, B1 to B7 are either absent or each independently represents a substituted or unsubstituted (C5 to C20) ring, preferably a substituted or unsubstituted (C5 to C13) ring, where the carbon atoms of this ring may be substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur, provided that at least five of B1 to B7 are present, and the rings immediately adjacent to B1 to B7 may be fused to each other. In this specification, "the rings immediately adjacent to B1 to B7 are fused to each other" means that the B1 ring and the B2 ring, the B2 ring and the B3 ring, the B3 ring and the B4 ring, the B4 ring and the B5 ring, the B5 ring and the B6 ring, or the B6 ring and the B7 ring are fused to each other.

[0038] According to one embodiment of the present disclosure, if any one of B1 to B7 represents a (C6 to C20) ring, then the immediately adjacent ring may not be present, or it may be a C5 ring in which the carbon atoms of the ring are substituted with one or more heteroatoms selected from nitrogen, oxygen, and sulfur.

[0039] According to another embodiment of the present disclosure, B1 to B7 may be absent independently, or each may be a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted cyclopentadiene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted pyridine ring, or a substituted or unsubstituted dibenzofuran ring. For example, B1 to B7 may be absent independently, or each may be an unsubstituted or substituted benzene ring with phenyl, naphthyl, and / or diphenyltriazinyl; a naphthalene ring; an unsubstituted or substituted cyclopentadiene ring with at least one methyl; a fluorene ring with at least one methyl; a pyrrole ring substituted with unsubstituted phenyl; a phenyl ring substituted with at least one deuterium, biphenyl, and / or pyridyl; a furan ring; a thiophene ring; a pyridine ring; or an unsubstituted or substituted diphenyltriazinyl dibenzofuran ring.

[0040] In one embodiment, Y is -N-L2-(Ar2) n Alternatively, it may be -O-, preferably -N-L2-(Ar2) n That's fine.

[0041] In one embodiment, Ar2 may be a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5-30 member) heteroaryl, or -NR3R4, preferably a substituted or unsubstituted (C6-C25) aryl, a substituted or unsubstituted (5-25 member) heteroaryl, or -NR3R4, more preferably an unsubstituted (C6-C25) aryl or a (C6-C25) aryl substituted with at least one of deuterium, (C1-C6) alkyl, and (3-30 member) heteroaryl; an unsubstituted (5-25 member) heteroaryl or a (C6-C18) aryl or a (C6-30 member) heteroaryl; or -NR3R4. For example, Ar2 is unsubstituted or deuterium-substituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted m-biphenyl; substituted or unsubstituted p-biphenyl; substituted or unsubstituted o-terphenyl; substituted or unsubstituted p-terphenyl; substituted or unsubstituted m-terphenyl; substituted or unsubstituted triphenylenyl; unsubstituted or phenyl-substituted pyridyl; unsubstituted or phenyl-substituted pyrimidinyl; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted dibenzofuranyl; unsubstituted or quinoxaline substituted with at least one of phenyl, m-biphenyl, p-biphenyl, dibenzofuranyl, and dibenzothiophenyl; unsubstituted or phenyl-substituted Benzoquinoxalines that have been modified; quinazolines that are unsubstituted or substituted with at least one of phenyl, m-biphenyl, p-biphenyl, dibenzofuranil, and dibenzothiophenyl; benzoflopyrimidinil that is unsubstituted or phenyl; benzothienopyrimidinil that is unsubstituted or phenyl; unsubstituted triazinyl, naphthyl, pyridyl, m-biphenyl, p-biphenyl, m-terphenyl that is unsubstituted or phenyl; fluorenyl, dibenzofuranil, and dibenzothiophenyl that are unsubstituted or methyl; or -NR3R4.

[0042] In one embodiment, L2 may be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-30 member) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 member) heteroarylene, and more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5-18 member) heteroarylene. For example, L2 may be a single bond, phenylene, m-biphenylene, naphthylene, pyridylene, triazinylene, dibenzofuranylene, quinoxalinylene, benzoquinoxalinylene, quinazolinylene, benzophropyrimidinylene, or benzothienopyrimidinylene.

[0043] According to one embodiment, the second host material represented by formula 2 above can be represented by any one of the following formulas 2-1 to 2-5. [ka]

[0044] In equations 2-1 to 2-5, Y1, Y2, Y3, and Y4 are each independently defined as Y in Equation 2, and if there are multiple Ar2s, each Ar2 may be the same or different; X1~X 12 These are, independently, -N= or -C(R b ) = represents, R b This represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl, or adjacent R b They may be connected to each other to form a ring, and multiple R b If present, each R b They may be the same or different.

[0045] In one embodiment, R b This may be hydrogen, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 member) heteroaryl, or adjacent R b The ' may be linked to each other to form a ring, preferably hydrogen, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25 member) heteroaryl, or adjacent R b ' may be linked together to form substituted or unsubstituted (5-30 member) monocyclic or polycyclic alicyclic rings, aromatic rings, or combinations thereof, more preferably hydrogen, substituted or unsubstituted (C6-C18) aryls, or substituted or unsubstituted (5-18 member) heteroaryls, or adjacent R b These may be linked together to form a substituted or unsubstituted (5-25 member) monocyclic or polycyclic aromatic ring. For example, R b may be phenyl, naphthyl, or a phenyl-substituted triazinyl; or adjacent R b These may be linked together to form a benzene ring, an indene ring substituted with at least one methyl group, or an unsubstituted or diphenyltriazinyl-substituted benzofuran ring.

[0046] According to one embodiment, Ar2 and R b Each of these can independently select one of the substituents listed in Group 1 below. [ka]

[0047] In Group 1, D1 and D2 each independently represent a benzene ring or a naphthalene ring; X 21 represents O, S, NR5, or CR6R7; X 22 Each of these independently represents either CR8 or N, but X 22 On the condition that at least one of them represents N; X 23 Each of these independently represents either CR9 or N; L 11 ~L 18 Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; R 11 ~R 21 And R5~R9 can each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1~C30) alkyl, substituted or unsubstituted (C6~C30) aryl, substituted or unsubstituted (3~30 member) heteroaryl, or substituted or unsubstituted (C3~C30) cycloalkyl, or can bond to adjacent substituents to form a ring; aa, ff, and gg each independently represent integers from 1 to 5, bb represents integers from 1 to 7, and cc, dd, and ee each independently represent integers from 1 to 4.

[0048] In one embodiment, D1 and D2 may be benzene rings; X 21 This may be O, S, or CR6R7; L 11 ~L 18 These may each be independent single bonds; R 11 ~R 21 And R5~R9 may each be independently hydrogen, deuterium, substituted or unsubstituted (C1~C20) alkyl, substituted or unsubstituted (C6~C25) aryl, or substituted or unsubstituted (5~25 member) heteroaryl, or adjacent substituents may be linked to each other to form a ring; aa, bb, ff, and gg may each be independently integers from 1 to 5; cc, dd, and ee may each be independently integers from 1 to 4. For example, R 11 R may be hydrogen, deuterium, phenyl, biphenyl, or a 26-membered heteroaryl; 12 It may be hydrogen, or adjacent R 12 ' may be linked to each other to form a benzene ring; R 13 , R 16 , and R 17R may be hydrogen; 18 and R 19 R may be hydrogen or phenyl; 21 R8 may be phenyl; R6 and R7 may be methyl; R8 may be hydrogen, phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, or adjacent R8' may be linked to each other to form a benzene ring; R9 may be hydrogen, unsubstituted phenyl, phenyl substituted with at least one deuterium, phenyl substituted with a 26-membered heteroaryl, naphthyl, biphenyl, dimethylfluorenyl, terphenyl, pyridyl substituted with phenyl, dibenzofuranyl, or dibenzothiophenyl; aa may be an integer of 1 or 5; bb may be an integer of 1 or 4; cc may be 1.

[0049] According to another embodiment, Ar2 and R b Each of these can independently select one of the substituents listed in Group 2 below. [ka] [ka] [ka] [ka]

[0050] In Group 2, L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; A1 to A3 each independently represent a substituted or unsubstituted (C1 to C30) alkyl group, or a substituted or unsubstituted (C6 to C30) aryl group.

[0051] According to another embodiment, Ar2 and Rb can each be independently selected from any one of the substituents listed in Group 3 below. [ka] [ka] [ka]

[0052] According to one embodiment, the second host material represented by the above formula 2 may be more specifically exemplified by, but is not limited to, the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0053] The compounds represented by Formula 2 in this disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compounds represented by Formula 2 can be prepared by referring to, but are not limited to, the following reaction schemes 3 to 6: [ka] [ka]

[0054] In reaction schemes 3 to 6, the definitions of substituents are as defined in formulas 2-1 to 2-5.

[0055] As described above, exemplary synthetic examples of compounds represented by Formula 2 in this disclosure are based on reactions such as the Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, cyclic dehydration reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction. It will be understood by those skilled in the art that these reactions proceed even when other substituents defined by Formulas 2-1 to 2-5, other than those described in the specific synthetic examples, are attached.

[0056] The following sections will describe organic electroluminescent devices that utilize the aforementioned host materials and / or organic electroluminescent materials containing them.

[0057] An organic electroluminescent device according to one embodiment includes a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode. The organic layer may include a light-emitting layer, and the light-emitting layer may include a plurality of host materials, including at least one first host material represented by formula 1 above and at least one second host material represented by formula 2 above.

[0058] According to one embodiment, the organic electroluminescent material of the present disclosure comprises at least one compound from compounds H1-1 to H1-124 as a first host material represented by formula 1 above, and at least one compound from compounds C-1 to C-300 as a second host material represented by formula 2 above, wherein the multiple host materials may be contained in the same organic layer or in different organic layers.

[0059] The light-emitting layer is a layer that emits light and may be a single layer or a multilayer in which two or more layers are laminated. In the light-emitting layer, the doping concentration of the dopant compound based on the host compound can preferably be less than 20% by weight, more preferably less than 17% by weight.

[0060] In addition to the light-emitting layer, the organic layer may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.

[0061] The organic layer may further include amine compounds and / or azine compounds in addition to the light-emitting material of this disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may include amine compounds, such as arylamine compounds and styrylarylamine compounds, as hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, or electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may include azine compounds as electron transport material, electron injection material, electron buffer material, and hole blocking material.

[0062] Furthermore, the organic layer further comprises 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, lanthanides, and organometallic d-transition elements, or at least one complex compound containing such a metal.

[0063] An organic electroluminescent material according to one embodiment can be used as a light-emitting material for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting devices, such as parallel side-by-side arrangements, stacked arrangements, or color conversion material (CCM) methods, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. In addition, the organic electroluminescent material according to one embodiment can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0064] One of the first and second electrodes may be an anode, and the other may be a cathode. In this case, the first and second electrodes can be formed from a permeable conductive material, a semi-permeable conductive material, or a reflective conductive material, respectively. Depending on the type of material used to form the first and second electrodes, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0065] 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 may be multilayered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each layer may use two compounds simultaneously. The hole injection layer may also be doped as a p-dopant. An electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, preventing electron overflow from the light-emitting layer and thus confining excitons within the light-emitting layer to prevent light leakage. The hole transport layer or electron blocking layer may consist of multiple layers, in which case each layer may use multiple compounds.

[0066] Electron buffer layers, hole blocking layers, electron transport layers, electron injection layers, or combinations thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each layer may use two compounds simultaneously. The hole blocking layer or electron transport layer may also be multilayered, where each layer may use multiple compounds. The electron injection layer may also be doped as an n-type dopant.

[0067] A luminescence auxiliary layer may be placed between the anode and the luminescence layer, or between the cathode and the luminescence layer. When the luminescence auxiliary layer is placed between the anode and the luminescence layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron overflow. When the luminescence auxiliary layer is placed between the cathode and the luminescence layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole overflow. In addition, a hole auxiliary layer may be placed between a hole transport layer (or hole injection layer) and the luminescence layer, and may be effective in facilitating or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. If the organic electroluminescent device includes two or more hole transport layers, any additionally included hole transport layers can be used as hole auxiliary layers or electron blocking layers. Luminescence auxiliary layers, hole auxiliary layers, or electron blocking layers may have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0068] In the organic electroluminescent device of this disclosure, at least one layer (hereinafter referred to as the "surface layer") preferably selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be disposed on the inner surface of one or both electrodes. Specifically, silicon and aluminum chalcogenide (including oxide) layers are preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. Operational stability for the organic electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X Examples of metal halides (1≦X≦1.5) include SiON and SiAlON; examples of metal halides include LiF, MgF2, CaF2, and rare earth metal fluorides; and examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, and CaO.

[0069] Furthermore, in the organic electroluminescent device of this disclosure, preferably, a mixed region of an electron transport compound and a reducing dopant or a mixed region of a hole transport compound and an oxidizing dopant may be located on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, thus facilitating the injection and transport of electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thus facilitating the injection and transport of holes from the mixed region into the electroluminescent 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. An organic electroluminescent device having two or more light-emitting layers and emitting white light can be fabricated by using the reducing dopant layer as a charge-generating layer.

[0070] An organic electroluminescent device according to one embodiment may further include at least one dopant in the light-emitting layer.

[0071] The dopants included in the organic electroluminescent devices of this disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent devices of this disclosure is not particularly limited, but is preferably a metallized complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an orthometallated complex compound of a metal atom selected as necessary from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an orthometallated iridium complex compound.

[0072] The dopants included in the organic electroluminescent devices of this disclosure may, but are not limited to, compounds represented by the following formula 101: [ka]

[0073] In Equation 101, L has the following structure 1 or 2: [ka] Selected from, In structures 1 and 2, R 100 ~R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or R 100 ~R 103 It may be linked to an adjacent substituent to form a substituted or unsubstituted condensed ring, for example, a substituted or unsubstituted quinoline, a substituted or unsubstituted benzoflopyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine, a substituted or unsubstituted benzofloxoquinoline, a substituted or unsubstituted benzothienoquinoline, or a substituted or unsubstituted indenoquinoline; R 104 ~R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or R 104 ~R 107It may bond to an adjacent substituent to form a substituted or unsubstituted condensed ring, such as substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzoflopyridine, or substituted or unsubstituted benzothienopyridine; R 111 ~R 121 Each of these elements independently represents hydrogen, deuterium, a halogen, an unsubstituted or halogen-substituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, or a substituted or unsubstituted (C6-C30) aryl, or may be bonded to an adjacent substituent to form a substituted or unsubstituted condensed ring; s represents an integer between 1 and 3.

[0074] In particular, specific examples of dopant compounds include, but are not limited to, the following. [ka] [ka] [ka] [ka]

[0075] To form each layer of the organic electroluminescent device of this disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating can be used, or wet film formation methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating can be used.

[0076] When using a wet film formation method, thin films can be formed by dissolving or diffusing the materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solvent can be any solvent that allows the materials forming each layer to dissolve or diffuse and that does not pose a problem in terms of film formation ability.

[0077] When forming a layer with a first host material and a second host material according to one embodiment, the layer can be formed by the methods listed above, and in many cases can be formed by co-evaporation or mixed evaporation. Co-evaporation is a mixed evaporation method in which two or more materials are placed in separate crucible sources and an electric current is passed through both cells simultaneously to evaporate the materials and perform mixed evaporation; mixed evaporation is a mixed evaporation method in which two or more materials are mixed in one crucible source before evaporation, and then an electric current is passed through one cell to evaporate the materials.

[0078] According to one embodiment, when the first host material and the second host material are present in the same or different layers of an organic electroluminescent device, the layers of the two host compounds can be formed separately. For example, the second host material may be deposited after the first host material has been deposited.

[0079] According to one embodiment, the present disclosure can provide a display device comprising a plurality of host materials, including a first host material represented by Formula 1 and a second host material represented by Formula 2. Furthermore, it is possible to manufacture a display device or a lighting device using the organic electroluminescent device of the present disclosure. Specifically, the organic electroluminescent device of the present disclosure can be used to manufacture display devices such as smartphones, tablets, notebooks, PCs, and TVs, or display devices for automobiles, or lighting devices such as outdoor or indoor lighting.

[0080] In the following sections, in order to understand this disclosure in detail, we will describe the method of preparing compounds according to this disclosure and their properties, referring to the synthesis methods of representative compounds. [Examples]

[0081] [Example 1] Preparation of Compound C-1 [ka] 1) Synthesis of compound 1-1 (9-phenyl-9H-carbazole-4-yl)boronic acid (96 g, 334.3 mmol), 2-bromo-1-chloro-3-nitrobenzene (71.8 g, 304 mmol), Pd2(dba)3 (15 g, 16.71 mmol), S-Phos (10.9 g, 26.76 mmol), and K3PO4 (315 g, 1.64 mmol) in a flask were dissolved in 1,500 mL of toluene and then stirred at 130 °C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual water was removed with magnesium sulfate, and the mixture was dried. Compound 1-1 (67 g, yield: 56.6%) was then separated by column chromatography.

[0082] 2) Synthesis of Compounds 1-2 Compound 1-1 (23.5 g, 58.9 mmol), (2-chlorophenyl)boronic acid (18.4 g, 117.8 mmol), Pd2(dba)3 (2.7 g, 2.95 mmol), S-Phos (2.4 g, 5.89 mmol), and K3PO4 (63 g, 294.5 mmol) in a flask were dissolved in 300 mL of toluene and then stirred at 130 °C for 12 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual water was removed with magnesium sulfate, and the mixture was dried. Compound 1-2 (14 g, yield: 50%) was then separated by column chromatography.

[0083] 3) Synthesis of compounds 1-3 Compounds 1-2 (13 g, 27.4 mmol) and triphenylphosphine (21.5 g, 82.1 mmol) in a flask were dissolved in 140 mL of o-DCB and then stirred at 220°C for 7 hours. After the reaction was complete, the reaction products were removed by distillation and then separated by column chromatography to obtain compound 1-3 (4 g, yield: 32%).

[0084] 4) Synthesis of compounds 1-4 Compounds 1-3 (10 g, 22.5 mmol), Pd(OAc)2 (505 mg, 2.25 mmol), Pcy3-HBF4 (1.63 g, 4.5 mmol), and Cs2CO3 (22 g, 67.5 mmol) in a flask were dissolved in 113 mL of o-xylene and stirred at 160°C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual water was removed with magnesium sulfate, and the mixture was dried. Compound 1-4 (1 g, 11% yield) was then separated by column chromatography.

[0085] 5) Synthesis of compound C-1 Compounds 1-4 (4.5 g, 11.06 mmol), 2-chloro-3-phenylquinoxaline (4 g, 16.6 mmol), DMAP (67 mg, 0.553 mmol), and Cs2CO3 (10.8 g, 331.8 mmol) in a flask were dissolved in 60 mL of DMSO and then refluxed at 140°C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual water was removed with magnesium sulfate, the mixture was dried, and then separated by column chromatography to obtain compound C-1 (2.5 g, 37% yield).

[0086] [Table 1]

[0087] [Example 2] Preparation of compound C-29 [ka] Compounds 1-4 (4g, 9.84 mmol), 3-bromo-1,1':2',1”-terphenyl (3.65g, 11.8 mmol), Pd2(dba)3 (448 mg, 0.492 mmol), S-Phos (448 mg, 0.984 mmol), and NaOtBu (2.84 g, 29.52 mmol) in a flask were dissolved in 50 mL of o-xylene and then stirred at 170°C for 4 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate, residual water was removed with magnesium sulfate, and the mixture was dried. Compound C-29 (1.5 g, yield: 24%) was then separated by column chromatography.

[0088] [Table 2]

[0089] [Example 3] Preparation of compound C-196 [ka] 1) Synthesis of compound 3-1 Compound A (60 g, 283 mmol), Compound B (100 g, 424 mmol), tetrakis(triphenylphosphine)palladium (16.3 g, 14.1 mmol), cesium carbonate (276 g, 849 mmol), 1,400 mL of toluene, 350 mL of ethanol, and 350 mL of distilled water were placed in a reaction vessel and stirred at 130 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and the organic layer was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed using a rotary evaporator. This was then separated by column chromatography to obtain Compound 3-1 (38 g, yield: 41%).

[0090] 2) Synthesis of compound 3-2 Compound 3-1 (38 g, 117 mmol), (2-chlorophenyl)boronic acid (35 g, 234 mmol), tris(dibenzylindenacetone)dipalladium (5.3 g, 5.86 mmol), S-Phos (4.8 g, 11.7 mmol), potassium triphosphate (62 g, 293 mmol), and 600 mL of toluene were placed in a reaction vessel and stirred under reflux for 2 hours. After the reaction was complete, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. This was then separated by column chromatography to obtain compound 3-2 (31 g, yield: 67%).

[0091] 3) Synthesis of compound 3-3 Compound 3-2 (21 g, 53.7 mmol), triphenyl phosphite (70 mL, 268 mmol), and 180 mL of DCB were placed in a reaction vessel and stirred at 200°C for 12 hours. After the reaction was complete, the DCB was removed by vacuum distillation and then washed with distilled water. The organic layer was then extracted with ethyl acetate, dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. Next, the mixture was separated by column chromatography to obtain compound 3-3 (10 g, yield: 55%).

[0092] 4) Synthesis of compounds 3-4 Compound 3-3 (6.6 g, 17.9 mmol), palladium(II) acetate (0.2 g, 0.89 mmol), PCy3-BF4 (1.3 g, 3.58 mmol), cesium carbonate (17 g, 53.7 mmol), and 90 mL of o-xylene were placed in a reaction vessel and stirred under reflux at 160°C for 4 hours. After the reaction was complete, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. Next, the organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. This was then separated by column chromatography to obtain compound 3-4 (1.8 g, yield: 32%).

[0093] 5) Synthesis of compound C-196 Compound 3-4 (1.8 g, 5.43 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2.3 g, 5.97 mmol), tris(dibenzylideneacetone)dipalladium (0.2 g, 0.27 mmol), tri-tert-butylphosphine (0.3 mL, 0.54 mmol), sodium tert-butoxide (1.3 g, 13.5 mmol), and 30 mL of toluene were placed in a reaction vessel and stirred under reflux for 3 hours. After the reaction was complete, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate. Next, the organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. This was then separated by column chromatography to obtain compound C-196 (3.3 g, yield: 95%).

[0094] [Table 3]

[0095] [Example 4] Preparation of compound C-36 [ka] Compounds 1-4 (4.0 g, 9.84 mmol), 4-bromo-N,N-diphenylaniline (3.2 g, 9.84 mmol), Pd2(dba)3 (0.45 g, 0.5 mmol), s-phos (0.4 g, 0.98 mmol), and NaOtBu (1.9 g, 19.7 mmol) in a flask were dissolved in 50 mL of o-xylene and then stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate and then separated by column chromatography to obtain compound C-36 (2.67 g, yield: 42%).

[0096] [Table 4]

[0097] [Example 5] Preparation of compound C-32 [ka] Compounds 1-4 (4.0 g, 9.84 mmol), 2-bromodibenzo[b,d]furan (1.7 g, 9.84 mmol), Pd2(dba)3 (0.45 g, 0.5 mmol), s-phos (0.4 g, 0.98 mmol), and NaOtBu (1.9 g, 19.7 mmol) in a flask were dissolved in 50 mL of o-xylene and then stirred under reflux for 5 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate and then separated by column chromatography to obtain compound C-32 (1.68 g, yield: 30%).

[0098] [Table 5]

[0099] In the following sections, the method for fabricating OLEDs according to this disclosure and their characteristics will be described in order to understand this disclosure in detail. However, this is merely a description of the features of the OLEDs according to this disclosure and is not limited to the following examples.

[0100] [Device Examples 1-3] Fabrication of OLEDs containing a host compound according to the present disclosure An OLED was manufactured using the host material according to this disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan), which is a transparent electrode on a glass substrate for the OLED, was sequentially ultrasonically cleaned with acetone and isopropyl alcohol, then stored in isopropanol, and subsequently used. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus. Then, compound HI-1 as the first hole injection compound was introduced into the cell of the vacuum deposition apparatus, and compound HT-1 as the first hole transport compound was introduced into another cell of the vacuum deposition apparatus. The two materials were evaporated at different rates, and the first hole injection compound was deposited with a doping amount of 3 wt% based on the total amount of the first hole injection compound and the first hole transport compound to form a first hole injection layer with a thickness of 10 nm. Next, compound HT-1 was deposited on the first hole injection layer as a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was introduced into another cell of the vacuum deposition apparatus, and an electric current was passed through the cell to evaporate it, thereby forming a 60 nm thick second hole transport layer on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was formed on top of them as follows: The first and second host compounds shown in Table 1 below were introduced as hosts into two cells of the vacuum deposition apparatus, and compound D-39 was introduced as a dopant into another cell. The two host materials were evaporated in a 1:1 ratio, and the dopant materials were evaporated simultaneously in different ratios. This was deposited with a doping amount of 3 wt% based on the total amount of host and dopant to form a 40 nm thick emissive layer on the hole transport layer. Next, compounds ETL-1 and EIL-1 were deposited as electron transport materials in a 50:50 weight ratio to form a 35 nm thick electron transport layer on the emissive layer. After depositing compound EIL-1 as an electron injection layer to a thickness of 2 nm onto the electron transport layer, an 80 nm thick Al cathode was deposited onto the electron injection layer using a separate vacuum deposition apparatus. In this way, an OLED was manufactured. Each compound used in all materials was 10 -6 It was purified by vacuum sublimation using a Thor device.

[0101] [Device Comparative Examples 1-3] Fabrication of OLEDs containing conventional compounds as hosts An OLED was manufactured using the same method as in Device Example 1, except that the host compounds listed in Table 1 below were used individually as hosts for the light-emitting layer.

[0102] As described above, the driving voltage, luminous efficiency, and emitted color of the organic electroluminescent devices manufactured using Device Examples 1-3 and Device Comparative Examples 1-3 were measured at a brightness of 1,000 nits, as well as the time required for the emission to decrease from 100% to 95% (lifetime; T95) at a brightness of 5,000 nits. The results are shown in Table 1 below.

[0103] [Table 6]

[0104] Table 1 above confirms that by including a specific combination of compounds according to this disclosure as a host material, it is possible to provide a long-life organic electroluminescent device that exhibits a low driving voltage and high luminescence efficiency, and significantly improves lifetime characteristics.

[0105] The compounds used in the above-mentioned device examples and device comparison examples are shown in Table 2 below.

[0106] [Table 7]

Claims

1. Formula 1-1 below: 【Chemistry 1】 (In the formula, Y １ , Y ３ and Y ５ represents N, and Y ２ , Y ４ and Y ６ CR ａ It represents; R ａ Each of these elements may independently represent hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C2-C30) alkenyl, or a substituted or unsubstituted (C6-C30) aryl, or may be linked with an adjacent substituent to form a ring; L １ represents a single bond or a substituted or unsubstituted (C6-C30) arylene; Ar １ This represents a substituted or unsubstituted (C6-C30) aryl; Ar １ The aforementioned substituted or unsubstituted (C6-C30) aryls are selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted binaphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted dibenzofluorenyl, substituted or unsubstituted phenantrenyl, substituted or unsubstituted phenylphenantrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted indenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted tetracenyl, substituted or unsubstituted perilenyl, substituted or unsubstituted crisenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[fluoren-fluoren]yl, and substituted or unsubstituted azlenyl, provided that Ar １ Triphenylenyl is excluded from the aforementioned substituted (C6-C30) aryl substituents, a represents an integer from 1 to 3, and if a is an integer of 2 or more, then each (L １ -Ar １ (They may be the same or different.) A first host material containing a compound represented by, Equation 2-1 below: 【Chemistry 2】 (In the formula, Y １ and Y ２ Each of these is independently -N(L ２ - (Ar ２ ) ｎ )-, -O-, -S-, or -C(R １ ) (Caution ２ ) - represents multiple Ar ２ If there exists, each Ar ２ They may be the same or different; L ２ This represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene. Ar ２ This includes substituted or unsubstituted (C6-C30) aryls, substituted or unsubstituted (3-30 member) heteroaryls, or -NR ３ R ４ This represents, X １ ~X １２ Each of these is independently -C(R ｂ ) = represents; R ｂ This represents hydrogen; R １ ~R ４ Each of these independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl, or adjacent substituents may be linked to form a ring; n represents an integer of 1 or 2, and if n is 2, Ar ２ (Each of them may be the same or different.) A plurality of host materials comprising a second host material containing a compound represented by .

2. The Ar ２ However, the following group 1: 【Transformation 3】 (In the formula, D1 and D2 each independently represent a benzene ring or a naphthalene ring; X ２１ O, S, NR ５ , or CR ６ R ７ It represents; X ２２ Each of them operates independently, CR ８ Or it represents N, but X ２２ On the condition that at least one of them represents N; X ２３ Each of them is independently CR ９ Or it represents N; L １１ ~L １８ Each of these independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 member) heteroarylene; R １１ ~R ２１ and R ５ ~R ９ Each of these independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 member) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl, or can be bonded to an adjacent substituent to form a ring; aa, ff, and gg each independently represent integers from 1 to 5, bb represents an integer from 1 to 7, and cc, dd, and ee each independently represent integers from 1 to 4. The host material according to claim 1, wherein one substituent is selected from any of the substituents listed in (1).

3. The Ar ２ However, the following groups 2 and 3: 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 (In the formula, L represents a single bond, a substituted or unsubstituted (C1-C30) alkylene, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3-30 member) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; A １ ~A ３ Each of these independently represents a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group. The host material according to claim 1, wherein one substituent is selected from any of the substituents listed in (1).

4. The compound represented by formula 1-1 is the following compound: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 A plurality of host materials according to claim 1, selected from the following.

5. The compound represented by formula 2-1 is the following compound: 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] A plurality of host materials according to claim 1, selected from the following.

6. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the at least one light-emitting layer comprises a plurality of host materials as described in claim 1.

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