Multiple host materials and organic electroluminescent devices comprising the same

By using a combined host material of the compounds of Formula 1 and Formula 2 in an organic electroluminescent device, the driving voltage and life problems are solved, and the luminescence efficiency is improved. It is suitable for a variety of display and lighting devices.

CN112689911BActive Publication Date: 2025-07-18DUPONT SPECIALTY MATERIALS KOREA LTD
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Patent Information

Application Number
CN201980059485.2
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Priority Date
2019-07-09
Filing Date
2019-08-07
Publication Date
2025-07-18
Estimated Expiration
2039-08-07

AI Technical Summary

Technical Problem

There is room for improvement in existing organic electroluminescent devices in terms of driving voltage, luminescence efficiency and lifetime, especially the electroluminescent characteristics requirements of medium and large OLED panels are not met.

Method used

A variety of host materials are used to constitute the light emitting layer of the organic electroluminescent device using at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2, and are formed by co-evaporation or mixed evaporation technology.

Benefits of technology

It realizes an organic electroluminescent device with low driving voltage, improved luminescence efficiency and extended life, and is suitable for a variety of application scenarios.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

The present disclosure relates to various host materials and an organic electroluminescent device including the same. By including the host materials according to the present disclosure, an organic electroluminescent device having a low driving voltage and / or high efficiency and / or long lifespan can be provided.
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Description

Technical Field

[0001] The present disclosure relates to various host materials and an organic electroluminescent device including the same. Background Art

[0002] The first organic electroluminescent device was developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0003] An organic electroluminescent device (OLED) converts electrical energy into light by applying electric power to an organic electroluminescent material, and generally includes an anode, a cathode, and an organic layer formed between the two electrodes.

[0004] The most important factor determining the luminous efficiency in an organic electroluminescent device is the light-emitting material. In terms of function, the light-emitting material is classified into a host material and a dopant material, and the light-emitting material can be used as a combination of a host and a dopant to improve color purity, luminous efficiency, and stability. Generally, a device having excellent EL (electroluminescence) characteristics has a structure including a light-emitting layer formed by doping a dopant into a host. When using such a dopant / host material system as the light-emitting material, the selection of the host material is important because it greatly affects the efficiency and lifetime of the organic electroluminescent device.

[0005] Recently, there has been an urgent task of developing an organic electroluminescent device having high efficiency and long lifetime. In particular, considering the electroluminescent characteristics required for medium and large OLED panels, there is an urgent need to develop highly excellent light-emitting materials superior to conventional materials.

[0006] KR 2015-0117173 A and KR2015-0042603 A disclose a composition for an organic electroluminescent device including various host compounds, and an organic electroluminescent device; however, improvements are still needed in terms of driving voltage, luminous efficiency, and lifetime. Summary of the Invention

[0007] Technical Problem

[0008] An object of the present disclosure is, firstly, to provide various host materials capable of producing an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long lifetime, and secondly, to provide an organic electroluminescent device including the host materials.

[0009] Solution to the Problem

[0010] As a result of in-depth research to solve the above technical problems, the inventors of the present invention have found that the above object can be achieved by a plurality of host materials including at least one first host compound represented by Formula 1 below and at least one second host compound represented by Formula 2 below, so as to complete the present invention.

[0011]

[0012] In Formula 1,

[0013] L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; and

[0014] Ar1 to Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;

[0015] Provided that compounds in which all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen are excluded;

[0016] HAr-(L-Ar) a′ ---(2)

[0017] In Formula 2,

[0018] HAr represents a substituted or unsubstituted nitrogen-containing (3- to 10-membered) heteroaryl group;

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

[0020] Ar represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and

[0021] a' represents an integer from 1 to 3, and when a' is 2 or greater, each (L-Ar) can be the same or different.

[0022] Advantages of the present invention

[0023] By using various host materials according to the present disclosure, an organic electroluminescent device having a low driving voltage and / or a high luminous efficiency and / or a long lifespan can be fabricated. Detailed implementation manners

[0024] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present invention and does not mean to limit the scope of the present invention in any way.

[0025] The present disclosure relates to various host materials and an organic electroluminescent device including the host materials, the host materials including at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2.

[0026] As used herein, "organic electroluminescent material" means a material that can be used in an organic electroluminescent device and can include at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a luminescence assisting material, an electron blocking material, a luminescent material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0027] As used herein, "various host materials" means a host material including a combination of at least two compounds, which can be included in any light-emitting layer constituting the organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (e.g., before vapor deposition) and the material after being included in the organic electroluminescent device (e.g., after vapor deposition). In one embodiment, the various host materials of the present disclosure can be a combination of at least two host materials, and optionally, can additionally include conventional materials included in the organic electroluminescent material. By methods known in the art, at least two compounds included in the various host materials of the present disclosure can be included together in one light-emitting layer, or can be included in different light-emitting layers respectively. For example, the at least two compounds can be co-evaporated or co-evaporated, or can be evaporated individually.

[0028] As used herein, “(C1-C30) (sub)alkyl” means a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms forming the chain, preferably 1 to 20 carbon atoms, and more preferably 1 to 10 carbon atoms. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C3-C30) (sub)cycloalkyl” is a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “(C6-C30) (sub)aryl” is a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, preferably 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms, which may be partially saturated and may contain a spiro structure. Specific examples of aryl groups include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthryl, benzoanthryl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, yl, benzo yl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulyl, etc. More specifically, the aryl group may be 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'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 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, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1- yl, 2- yl, 3- yl, 4- yl, 5- Group, 6- Group, benz[c]phenanthrenyl, benzo[g] Base, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluorenyl, 4-fluorenyl, 8-fluorenyl, 9-fluorenyl, benzofluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, etc. "(3- to 30-membered)(hetero)aryl" is an aryl group having 3 to 30 ring skeleton atoms, preferably 5 to 25 ring skeleton atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge. The above heteroatoms can be connected to at least one substituent selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(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(C6-30)arylamino. In addition, the above heteroaryl can be a heteroaryl formed by connecting at least one heteroaryl or aryl to the heteroaryl via one or more single bonds; and can contain a spiro structure. Specific examples of the heteroaryl can include monocyclic heteroaryls, which include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and polycyclic heteroaryls, which include benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl,indolizidinyl, acrylidinyl, silafluorenyl, germafluorenyl, etc. More specifically, the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-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-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 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-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-iso-benzofuryl, 3-iso-benzofuryl, 4-iso-benzofuryl, 5-iso-benzofuryl, 6-iso-benzofuryl, 7-iso-benzofuryl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl,2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-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-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germaf luorenyl, 2-germaf luorenyl, 3-germaf luorenyl, 4-germaf luorenyl, etc. In this text, "halogen" includes F, Cl, Br, and I.

[0029] In addition, "ortho (o)", "meta (m)", and "para (p)" mean the substitution positions indicating all substituents. The ortho position is a compound having substituents adjacent to each other, such as at the 1-position and 2-position on benzene. The meta position is the next substitution position adjacent to the adjacent substitution positions. For example, the compound has substituents at the 1-position and 3-position on benzene. The para position is the next substitution position after the meta position. For example, the compound has substituents at the 1-position and 4-position on benzene.

[0030] In this text, "substituted or unsubstituted ring formed by connecting with adjacent substituents" means a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by connecting or fusing two or more adjacent substituents; preferably, it can be a substituted or unsubstituted (3-membered to 26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. In addition, at least one of the carbon atoms in the formed ring can be replaced by at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is (5-membered to 20-membered), and according to another embodiment of the present disclosure, the number of ring backbone atoms is (5-membered to 15-membered).

[0031] In addition, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). In L1 to L3, Ar1 to Ar3, HAr, L, and Ar of Formulas 1 and 2, the substituents of substituted (C1-C30) (sub)alkyl, substituted (C6-C30) (sub)aryl, substituted (3-membered to 30-membered) (sub)heteroaryl, substituted (C3-C30) (sub)cycloalkyl, substituted (C1-C30) alkoxy, substituted tris(C1-C30) alkylsilyl, substituted bis(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkylbis(C6-C30) arylsilyl, substituted tris(C6-C30) arylsilyl, substituted mono- or di-(C1-C30) alkylamino, substituted mono- or di-(C6-C30) arylamino, or substituted (C1-C30) alkyl(C6-C30) arylamino are each independently at least one selected from the group consisting of: deuterium, halogen, cyano, carboxyl, 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-membered to 7-membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl-substituted or unsubstituted (5-membered to 30-membered) heteroaryl, (5-membered to 30-membered) heteroaryl-substituted or unsubstituted (C6-C30) aryl, tris(C1-C30) alkylsilyl, tris(C6-C30) arylsilyl, bis(C1-C30) alkyl(C6-C30) arylsilyl, (C1-C30) alkylbis(C6-C30) arylsilyl, amino, mono- or di-(C1-C30) alkylamino, (C1-C30) alkyl-substituted or unsubstituted mono- or di-(C6-C30) arylamino, (C1-C30) alkyl(C6-C30) arylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, bis(C6-C30) arylboronyl, bis(C1-C30) alkylboronyl, (C1-C30) alkyl(C6-C30) arylboronyl, (C6-C30) aryl(C1-C30) alkyl, and (C1-C30) alkyl(C6-C30) aryl. For example, the substituents may be methyl, phenyl, biphenyl, naphthyl, fluorenyl, or pyridyl, etc.

[0032] Hereinafter, a host material according to an embodiment will be described.

[0033] The host material according to one embodiment includes at least one first host compound represented by Formula 1 below and at least one second host compound represented by Formula 2 below; and according to one embodiment, the host material may be included in the light-emitting layer of an organic electroluminescent device.

[0034] According to one embodiment, the first host compound as the host material may be represented by Formula 1 below.

[0035]

[0036] In Formula 1,

[0037] L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; and

[0038] Ar1 to Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group;

[0039] Provided that compounds in which all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen are excluded.

[0040] In one embodiment, L1 to L3 may each independently be a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene group, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5-membered to 25-membered) heteroarylene group, more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene group. For example, L1 to L3 may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted o-biphenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted p-biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group.

[0041] In one embodiment, Ar1 to Ar3 may each independently be hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5- to 30-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C20) aryl, or a substituted or unsubstituted (5- to 25-membered) heteroaryl. For example, Ar1 to Ar3 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzothienyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzocarbazolyl, a substituted or unsubstituted indeno-carbazolyl, a substituted or unsubstituted benzothieno-carbazolyl, a substituted or unsubstituted benzofuro-carbazolyl, or a substituted or unsubstituted indolo-carbazolyl.

[0042] The compound represented by Formula 1 may be represented by any one of Formulas 1-1 to 1-6 below.

[0043]

[0044]

[0045] In Formulas 1-1 to 1-6,

[0046] Y represents CR6R7, NR8, O, or S;

[0047] R1 to R8 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be connected to an adjacent substituent to form a ring;

[0048] L4 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;

[0049] Ar4 represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group;

[0050] a, b, c, and e each independently represent an integer from 1 to 4, b", c", and e" each independently represent an integer from 1 to 3, d represents an integer of 1 or 2, d" represents the integer 1, and when a to e, b", c", and e" are 2 or greater, each of R1 to R5 can be the same or different; and

[0051] Ar2, Ar3, and L1 to L3 are as defined in Formula 1.

[0052] In one embodiment, Y can be NR8, O, or S.

[0053] In one embodiment, R1 to R5 can each independently be hydrogen, deuterium, a halogen, a cyano group, or can be joined to an adjacent substituent to form a ring, preferably hydrogen, deuterium, or can be joined to an adjacent substituent to form a substituted or unsubstituted (3- to 18-membered) monocyclic or polycyclic ring, more preferably hydrogen or can be joined to an adjacent substituent to form an unsubstituted (3- to 10-membered) monocyclic or polycyclic aromatic ring. For example, adjacent R1 or adjacent R2 can be joined to each other to form a benzene ring.

[0054] In one embodiment, R6 to R8 can each independently be hydrogen, deuterium, a halogen, a cyano group, or a substituted or unsubstituted (C6-C30) aryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group. For example, R6 to R8 can each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0055] In one embodiment, L4 can be a single bond or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond or a substituted or unsubstituted (C6-C25) arylene group, more preferably a single bond or a substituted or unsubstituted (C6-C18) arylene group. For example, L4 can be a single bond or a substituted or unsubstituted phenylene group.

[0056] In one embodiment, Ar4 may be hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group. For example, Ar4 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-biphenyl group, or a substituted or unsubstituted p-biphenyl group.

[0057] According to one embodiment, the first host compound represented by Formula 1 may be illustrated by the following compounds, but is not limited thereto.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] The compound having Formula 1 according to the present disclosure may be produced by synthesis methods known to those skilled in the art. For example, it may be synthesized by the methods disclosed in KR 2013-0106255 A (September 27, 2013), KR 2012-0042633 A (May 3, 2012), and KR 2015-0066202 A (June 16, 2015), but is not limited thereto.

[0065] According to one embodiment, a second host compound as another host material may be represented by Formula 2 below.

[0066] HAr-(L-Ar) a′ ---(2)

[0067] In Formula 2,

[0068] HAr represents a substituted or unsubstituted nitrogen-containing (3- to 10-membered) heteroaryl group;

[0069] L represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group;

[0070] Ar represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and

[0071] a' represents an integer from 1 to 3, and when a' is 2 or greater, each (L-Ar) can be the same or different.

[0072] In one embodiment, HAr can be a substituted or unsubstituted nitrogen-containing (5- to 10-membered) heteroaryl, preferably an unsubstituted nitrogen-containing (6- to 10-membered) heteroaryl. For example, HAr can be pyridyl, pyrimidinyl, triazinyl, quinolinyl, quinoxalinyl, or quinazolinyl.

[0073] In one embodiment, L can be a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene, preferably a single bond, an unsubstituted (C6-C20) arylene, or a substituted or unsubstituted (5- to 18-membered) heteroarylene. For example, L can be a single bond, a naphthyl-substituted or unsubstituted phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted fluorenylene, or a substituted or unsubstituted pyridylene.

[0074] In one embodiment, Ar can be a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, preferably a (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar can be a naphthyl- or fluorenyl-substituted or unsubstituted phenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted phenanthryl, a fluorenyl substituted with at least one phenyl or at least one methyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzofuranyl, a phenyl-substituted or unsubstituted carbazolyl, or a benzofluorene substituted with at least one of methyl, phenyl, biphenyl, naphthyl, and pyridyl.

[0075] In one embodiment, a' can be an integer of 2 or 3, where each (L-Ar) can be the same or different.

[0076] The compound represented by Formula 2 can be represented by the following Formula 2-1 or 2-2.

[0077]

[0078] In Formulas 2-1 and 2-2,

[0079] X1 to X6 and Z1 to Z4 each independently represent CR a or N, where at least one of X1 to X6 is N, and at least one of Z1 to Z4 is N;

[0080] R a each independently represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, or substituted or unsubstituted (C6-C30) aryl; and

[0081] L, Ar, and a' are as defined in Formula 2.

[0082] In one embodiment, in Formula 2-1, at least one of X1 to X6 is N, preferably, at least two of X1 to X6 can be N, more preferably, at least three of X1 to X6 can be N. For example, the compound represented by Formula 2-1 can be (L-Ar) a’ -substituted pyridine, pyrimidine, or triazine.

[0083] In one embodiment, in Formula 2-2, at least one of Z1 to Z4 is N, preferably, at least two of Z1 to Z4 can be N. For example, the compound represented by Formula 2-2 can be (L-Ar) a’ -substituted quinoline, quinoxaline, or quinazoline.

[0084] In one embodiment, R a can all be hydrogen.

[0085] According to one embodiment, the second host compound represented by Formula 2 can be more specifically illustrated by the following compounds, but not limited thereto.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] The compound having Formula 2 according to the present disclosure can be produced by a synthesis method known to those skilled in the art. For example, the compound represented by Formula 2-1 or 2-2 can be synthesized by referring to the following Reaction Scheme 1 or 2, but not limited thereto:

[0094] [Reaction Scheme 1]

[0095]

[0096] [Reaction Scheme 2]

[0097]

[0098] In Reaction Schemes 1 and 2, L, Ar, and a' are as defined in Formula 2, and X1 to X6 and Z1 to Z4 are as defined in Formulas 2-1 and 2-2.

[0099] As described above, exemplary synthesis examples of compounds represented by Formula 2-1 or 2-2 according to an embodiment are described. Those skilled in the art will understand that the above reactions will proceed even if other substituents defined in Formula 2-1 or 2-2 other than the substituents described in the specific synthesis examples are bonded.

[0100] Hereinafter, an organic electroluminescent device applied to the above-described various host materials will be described.

[0101] The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer interposed 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 host material, and the host material includes at least one first host compound represented by Formula 1 and at least one second host compound represented by Formula 2.

[0102] According to an embodiment, the first host compound represented by Formula 1 and the second host compound represented by Formula 2 may be included in the same organic layer or may be separately included in different organic layers.

[0103] The light-emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the light-emitting layer, it is preferable that the doping concentration of the dopant compound is less than 20 wt%, preferably 17 wt%, based on the host compound.

[0104] One of the first electrode and the second electrode may be an anode, and the other may be a cathode; wherein, the first electrode and the second electrode may each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials forming the first electrode and the second electrode, the organic electroluminescent device may be a top-emission type, a bottom-emission type, or a side-emission type. The organic layer may include a light-emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting 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.

[0105] The organic layer may further include an amine-based compound and / or an azine-based compound in addition to the luminescent materials of the present disclosure. Specifically, the hole injection layer, the hole transport layer, the hole assisting layer, the light emitting layer, the light emitting assisting layer, or the electron blocking layer may contain an amine-based compound (e.g., an arylamine-based compound and a styrylarylamine-based compound, etc.) as a hole injection material, a hole transport material, a hole assisting material, a luminescent material, a light emitting assisting material, or an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, or the hole blocking layer may contain an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole blocking material.

[0106] In addition, the organic layer may further include at least one metal selected from the group consisting of metals of Group 1 of the periodic table, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organometals of d-transition elements, or at least one complex compound containing such a metal.

[0107] According to one embodiment, the organic electroluminescent material can be used as a luminescent material for a white organic light emitting device. According to the arrangement of R (red), G (green), B (blue), or YG (yellow-green) light emitting units, various structures of white organic light emitting devices have been proposed, such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, etc. In addition, according to one embodiment, the organic electroluminescent material can also be applied to an organic electroluminescent device containing QD (quantum dots).

[0108] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and each of the multilayers may use two compounds simultaneously. In addition, the hole injection layer may be doped with a p-type dopant. The electron blocking layer may be placed between the hole transport layer (or the hole injection layer) and the light emitting layer, and excitons can be confined within the light emitting layer by blocking the overflow of electrons from the light emitting layer to prevent light leakage. The hole transport layer or the electron blocking layer may be multilayered, and each layer thereof may use a plurality of compounds.

[0109] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be multilayered to control the injection of electrons and improve the interfacial characteristics between the light emitting layer and the electron injection layer, and each of the multilayers may use two compounds simultaneously. The hole blocking layer or the electron transport layer may also be multilayered, and each layer thereof may use a plurality of compounds. In addition, the electron injection layer may be doped with an n-type dopant.

[0110] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to facilitate hole injection and / or hole transport, or to prevent electron spillage. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to facilitate electron injection and / or electron transport, or to prevent hole spillage. In addition, a hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), so as to enable the control of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer can have the effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

[0111] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") can preferably be disposed on one or more inner surfaces of one or both electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface of the electroluminescent medium layer. The operating stability of the organic electroluminescent device can be obtained through the surface layer. Preferably, the chalcogenide includes SiO X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0112] In addition, in the organic electroluminescent device of the present disclosure, 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 can be disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport 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. In addition, the reducing dopant layer can be used as a charge generation layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0113] According to one embodiment, the organic electroluminescent device may further include at least one dopant in the light-emitting layer.

[0114] The dopant included in the organic electroluminescent material of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be a complex compound of one or more metallized metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably a complex compound of one or more ortho-metallized metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably a complex compound of one or more ortho-metallized iridium complex compounds.

[0115] The dopant included in the organic electroluminescent device may use the compound represented by Formula 101, but is not limited thereto:

[0116]

[0117] In Formula 101,

[0118] wherein, L is selected from the following Structure 1 or 2:

[0119]

[0120] R 100 to R 103 each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be connected to one or more adjacent substituents to form a substituted or unsubstituted fused ring, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indolopyridine, substituted or unsubstituted benzofuranquinoline, substituted or unsubstituted benzothienquinoline, or substituted or unsubstituted indoloquinoline;

[0121] R 104 to R 107Each independently represents hydrogen, deuterium, a halogen, a halogen-substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; or may be linked to one or more adjacent substituents to form a substituted or unsubstituted fused ring, for example, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted indolopyridine, a substituted or unsubstituted benzofuropyridine, or a substituted or unsubstituted benzothiophenopyridine;

[0122] R 201 to R 211 Each independently represents hydrogen, deuterium, a halogen, a halogen-substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or a substituted or unsubstituted (C6-C30) aryl group; or may be linked to one or more adjacent substituents to form a substituted or unsubstituted fused ring; and

[0123] s represents an integer from 1 to 3.

[0124] Specific examples of the dopant compound include, but are not limited to, the following items.

[0125]

[0126]

[0127]

[0128]

[0129] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating method, etc., or a wet film-forming method such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, flow coating method, etc. can be used. When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material for forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0130] When forming a layer from a first host compound and a second host compound according to an embodiment, the above methods can be used, and preferably co-evaporation or mixed evaporation can be used. Co-deposition is a mixed deposition method in which two or more isomeric materials are placed in corresponding individual crucible sources and a current is applied to two chambers simultaneously to evaporate the materials and perform mixed deposition; and mixed deposition is a mixed deposition method in which two or more isomeric materials are mixed in one crucible source before deposition and then a current is applied to one chamber to evaporate the materials.

[0131] When the first host compound and the second host compound are present in the same layer or different layers in an organic electroluminescent device according to an embodiment, the two host compounds can be deposited individually. For example, the first host compound can be deposited, and then the second host compound can be deposited.

[0132] According to an embodiment, by using a plurality of host materials including a compound represented by Formula 1 and a compound represented by Formula 2, the present disclosure can provide a display device such as a display device of a smartphone, a tablet computer, a laptop computer, a PC, a TV, or a vehicle, or a lighting device such as outdoor or indoor lighting.

[0133] Hereinafter, a method for manufacturing an organic electroluminescent device including a plurality of host materials according to the present disclosure and its characteristics will be explained in order to understand the present disclosure in detail.

[0134] [Device Examples 1-1, 1-2, 2-1 to 2-7, 3-1 to 3-4, 4-1 to 4-6, 5-1, and 5-2] Produce an OLED deposited with a first host compound and a second compound as hosts according to the present disclosure

[0135] Produce an OLED containing the compound of the present disclosure. First, an indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) of a transparent electrode on a glass substrate for an OLED device is subjected to ultrasonic washing successively with acetone, trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. Then, the ITO substrate is mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 is introduced into a chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus is controlled to 10 -6Then, an electric current is applied to the chamber to evaporate the materials introduced above, thereby forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: The first host compound and the second host compound in Table 1 below are introduced as hosts into one chamber of the vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into another chamber. The two host materials are evaporated at a rate of 1:1, and the dopant is deposited at a doping amount of 3 wt% simultaneously to form a light-emitting layer with a thickness of 40 nm on the hole transport layer. Next, compounds ET-1 and EI-1 are evaporated and deposited at a rate of 1:1 to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED is produced.

[0136] [Comparative Examples 1 to 5] Production of OLEDs Containing Comparative Compounds as Hosts

[0137] Except for using the compounds in Table 1 below as the hosts of the light-emitting layer, OLEDs are produced in the same manner as in Device Example 1-1.

[0138] Table 1 below shows the driving voltage, luminous efficiency, efficiency increase rate compared to a single host, and power efficiency of the organic electroluminescent devices of Device Examples 1-1, 1-2, 2-1 to 2-7, 3-1 to 3-4, 4-1 to 4-6, 5-1, and 5-2 and Comparative Examples 1 to 5 produced as described above at a brightness of 5,000 nits, as well as the results of the time (lifetime; T96) taken to decrease from 100% to 96% at a brightness of 5,000 nits.

[0139] Table 1

[0140]

[0141]

[0142] [Device Examples 6 to 8] Produce an OLED in which a first host compound and a second compound according to the present disclosure are deposited as hosts

[0143] Except for using the compounds in Table 2 below as the host of the light-emitting layer, an OLED was produced in the same manner as in Device Example 1-1.

[0144] [Comparative Example 6] Produce an OLED containing a comparative compound as the host

[0145] Except for using the compounds in Table 2 below as the host of the light-emitting layer, an OLED was produced in the same manner as in Device Example 1-1.

[0146] The results of the luminous efficiency, power efficiency, and the time (lifetime; T70) taken to decrease from 100% to 70% at a brightness of 1,000 nits of the organic electroluminescent devices of Device Examples 6 to 8 and Comparative Example 6 produced as described above are shown in Table 2 below.

[0147] Table 2

[0148]

[0149] Referring to Tables 1 and 2 above, it was confirmed that an organic electroluminescent device containing a specific combination of compounds according to an embodiment as a host material can significantly reduce the driving voltage and has improved characteristics in terms of efficiency and lifetime compared to conventional organic electroluminescent devices.

[0150] The compounds used in the device examples and comparative examples are shown in Table 3 below.

[0151] Table 3

[0152]

[0153]

[0154]

Claims

1. A plurality of host materials, the host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by Formula 1 and the second host compound is represented by Formula 2-1 or 2-2: Wherein, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; and Ar1 to Ar3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; Provided that compounds in which all of L1 to L3 are single bonds and all of Ar1 to Ar3 are hydrogen are excluded; Wherein, X1 to X6 and Z1 to Z4 each independently represent CR a or N, where at least one of X1 to X6 is N, and at least one of Z1 to Z4 is N; R a each independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, or a substituted or unsubstituted (C6-C30) aryl group; L represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3- to 30-membered) heteroarylene group; Ar in Formula 2-1 represents a naphthyl- or fluorenyl-substituted or unsubstituted phenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted phenanthryl group, a fluorenyl group substituted with one phenyl group or at least one methyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a benzo[9,10]fluorene group substituted with at least one of methyl, phenyl, terphenyl, naphthyl, and pyridyl; Ar in Formula 2-2 represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a phenyl-substituted or unsubstituted carbazolyl group; and a' represents an integer from 1 to 3, and when a' is 2 or greater, each (L-Ar) may be the same or different.

2. The main material according to claim 1, wherein, The Formula 1 is represented by any one of Formula 1-1 to 1-6: Wherein, Y represents CR6R7, NR8, O, or S; R1 to R8 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; or may be connected to adjacent substituents to form a ring; L4 represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; Ar4 represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group; a, b, c, and e each independently represent an integer from 1 to 4, b", c", and e" each independently represent an integer from 1 to 3, d represents an integer of 1 or 2, d" represents 1, and when a to e, b", c", and e" are 2 or greater, each of R1 to R5 may be the same or different; and Ar2, Ar3, and L1 to L3 are as defined in claim 1.

3. The main material according to claim 1, wherein, Among L1 to L3, Ar1 to Ar3, L, and Ar, the substituents of the substituted (C1-C30)(sub)alkyl, substituted (C6-C30)(sub)aryl, substituted (3-membered to 30-membered)(sub)heteroaryl, substituted (C3-C30)(sub)cycloalkyl, substituted (C1-C30)alkoxy, substituted tris(C1-C30)alkylsilyl, substituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tris(C6-C30)arylsilyl, substituted mono- or di-(C1-C30)alkylamino, substituted mono- or di-(C6-C30)arylamino, or substituted (C1-C30)alkyl(C6-C30)arylamino each independently represent at least one selected from the group consisting of: deuterium, halogen, cyano, carboxyl, 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-membered to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl-substituted or unsubstituted (5-membered to 30-membered)heteroaryl, (5-membered to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl, tris(C1-C30)alkylsilyl, tris(C6-C30)arylsilyl, bis(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, (C1-C30)alkyl-substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, bis(C6-C30)arylboronyl, bis(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

4. The main material according to claim 1, wherein, The compound represented by Formula 1 is selected from the group consisting of:

5. The main material according to claim 1, wherein, The compound represented by Formula 2-1 or 2-2 is selected from the group consisting of:

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 contains a plurality of host materials according to Claim 1.

Citation Information

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