A plurality of host materials and organic electroluminescent device comprising the same
Patent Information
- Application Number
- KR1020190175302
- Authority / Receiving Office
- KR · KR
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2019-12-26
- Publication Date
- 2026-09-16
- Estimated Expiration
- 2039-12-26
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Figure 112019134207528-PAT00001 
Figure 112019134207528-PAT00002 
Figure 112019134207528-PAT00003
Abstract
Description
Technology Field
[0001] The present invention relates to a plurality of host materials and an organic electroluminescent device containing the same. Background Technology
[0002] Since Tang et al. at Eastman Kodak first developed a TPD / Alq3 double-layer small molecule green organic light-emitting diode (OLED) consisting of an emissive layer and a charge transport layer in 1987, research on organic light-emitting diodes has progressed rapidly, leading to their current commercialization. Currently, organic light-emitting diodes primarily utilize phosphorescent materials with excellent luminous efficiency for panel implementation. To ensure long-term display usage and high resolution, OLEDs with high luminous efficiency and / or long lifespan are required.
[0003] Various materials or concepts have been proposed for the organic layer of organic electroluminescent devices to improve luminous efficiency, driving voltage, and / or lifespan, but they have not been satisfactory for practical use.
[0004] Korean Patent Publication No. 2015-0124902 discloses multiple types of host materials using compounds of carbazole derivatives, and Korean Patent Publication No. 2017-0022865 and Korean Patent Publication No. 2018-0099487 disclose host compounds having a basic framework of phenantrooxazole-based and / or phenantrothiazole-based compounds, but they do not specifically disclose the multiple types of host materials claimed herein. Furthermore, there is a need to continuously develop luminescent materials with improved performance, such as low driving voltage, high luminous efficiency, high power efficiency, and / or excellent lifespan characteristics. Prior art literature
[0005] Korean Patent Publication No. 2015-0124902 (Published Nov. 06, 2015) Korean Patent Publication No. 2017-0022865 (Published Mar. 02, 2017) Korean Patent Publication No. 2018-0099487 (Published Sep. 05, 2018) The problem to be solved
[0006] The objective of the present invention is to provide an organic electroluminescent device having low driving voltage, high luminous efficiency, high power efficiency and / or excellent lifespan characteristics by including multiple types of host materials comprising a specific combination of compounds. means of solving the problem
[0007] As a result of diligent research to solve the above technical problem, the inventors have completed the present invention by discovering that a plurality of host materials comprising a first host material containing a compound represented by the following chemical formula 1 and a second host material containing a compound represented by the following chemical formula 2 achieve the above-described objective.
[0008] [Chemical Formula 1]
[0009]
[0010] In the above chemical formula 1,
[0011] X1 and Y1 are independently -N=, -NR 15 -, -O- or -S-, provided that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR 15 -, -O- or -S- and;
[0012] L1 is a single bond, or a substituted or unsubstituted (C6-C30)arylene;
[0013] Ar1 is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30)heteroarylamino;
[0014] R 11 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl;
[0015] R 12 to R 15 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; can form a ring by connecting to an adjacent substituent;
[0016] a and b are each independently 1 or 2, c is an integer from 1 to 3, and if a to c are integers of 2 or more, each R 12 to R 14 They may be identical or different from each other;
[0017] [Chemical Formula 2]
[0018]
[0019] In the above chemical formula 2,
[0020] HAr is a substituted or unsubstituted (3-30) heteroaryl containing a nitrogen atom;
[0021] L2 is a single bond, or a substituted or unsubstituted (C6-C30)arylene;
[0022] R1 to R8 are each independently (C6-C30)aryls substituted or unsubstituted with hydrogen, deuterium, or deuterium. Effects of the invention
[0023] By including a plurality of host materials according to the present invention, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, higher power efficiency and / or excellent lifespan characteristics compared to conventional organic electroluminescent devices is provided, and it is possible to manufacture a display device or lighting device using the same. Specific details for implementing the invention
[0024] The present invention is described in more detail below, but this is for illustrative purposes only and should not be interpreted as limiting the scope of the present invention.
[0025] In the present invention, "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device, may include one or more compounds, and 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 assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
[0026] In the present invention, "multiple types of organic electroluminescent materials" refers to an organic electroluminescent material composed of two or more compounds that may be included in any layer constituting an organic electroluminescent device, and may refer to both the material before (e.g., before deposition) and after (e.g., after deposition) inclusion in the organic electroluminescent device. For example, the multiple types of organic electroluminescent materials may be a combination of two or more compounds that may be included in one or more layers among a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. These two or more compounds may be included in the same layer or different layers, may be mixed-deposited or co-deposited, or may be deposited individually.
[0027] In this invention, "multiple types of host materials" refers to an organic electroluminescent material composed of two or more types of host materials, and may refer to both the materials before (e.g., before deposition) and after (e.g., after deposition) inclusion in an organic electroluminescent device. The multiple types of host materials of this invention may be included in any light-emitting layer constituting an organic electroluminescent device, and the two or more compounds included in the multiple types of host materials may be included together in one light-emitting layer or each may be included in different light-emitting layers. When two or more types of host materials are included in one layer, for example, they may be mixed-deposited to form a layer, or they may be separately and simultaneously co-deposited to form a layer.
[0028] In the present invention, "(C1-C30)alkyl" refers to a straight-chain or branched-chain alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. Specific examples of the above alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. In the present invention, "(C2-C30)alkenyl" refers to a straight-chain or branched-chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Specific examples of the above alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. In the present invention, "(C2-C30)alkynyl" refers to a straight-chain or branched-chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10. Examples of the alkynyl include ethinyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-inyl, etc. In the present invention, "(C3-C30)cycloalkyl" refers to a single-ring or polycyclic hydrocarbon having 3 to 30 carbon atoms in a ring skeleton, wherein the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. In this document, "(3-7)heterocycloalkyl" refers to a cycloalkyl having 3 to 7, preferably 5 to 7, ring-skeleton atoms and comprising one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N; examples include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. In this document, "(C6-C30)aryl(lene)" refers to a single-ring or fused-ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in a ring-skeleton, andIt may be partially saturated. The number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, non-naphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, azulenyl, etc. More specifically, examples of the above aryls include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzantryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-crisenyl, 2-crisenyl, 3-crisenyl, 4-crisenyl, 5-crisenyl, 6-crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, 1-triphenyllenyl, 2-triphenyllenyl, 3-triphenyllenyl, 4-triphenyllenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl. Benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, 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-quaternphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesithyl, o-cumenyl, m-cumenyl, p-cumenyl, pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenylyl, 4"-t-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, 11,11-dimethyl-1-benzo[a]fluorenyl, 11,11-dimethyl-2-benzo[a]fluorenyl, 11,11-dimethyl-3-benzo[a]fluorenyl, 11,11-dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11-dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl-6-benzo[b]fluorenyl, 11,11-dimethyl-7-benzo[b]fluorenyl, 11,11-dimethyl-8-benzo[b]fluorenyl, 11,11-dimethyl-9-benzo[b]fluorenyl, 11,11-dimethyl-10-benzo[b]fluorenyl, 11,11-dimethyl-1-benzo[c]fluorenyl, 11,11-dimethyl-2-benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a]fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl, 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl Fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, Examples include 11,11-diphenyl-10-benzo[c]fluorenyl, etc.
[0029] In this document, "(3-30)heteroaryl or (3-50)heteroaryl" refers to an aryl group having 3 to 30 or 3 to 50 ring skeleton atoms and comprising one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. Additionally, in this document, the heteroaryl includes a form in which one or more heteroaryl or aryl groups are connected to a heteroaryl group by a single bond, and also includes a form having a spiro structure. Examples of the above heteroaryls include single-cyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazineyl, tetrazineyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazineyl, pyrimidineyl, pyridazineyl, etc., benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, There are fused cyclic heteroaryls such as isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naftiridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, and dihydroacridinyl. More specifically, examples of the above heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl,3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 3-Pyridinyl, 4-Pyridinyl, 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-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 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-Isoquinolil, 3-Isoquinolil, 4-Isoquinolil, 5-Isoquinolil, 6-Isoquinolil, 7-Isoquinolil, 8-Isoquinolil, 2-Quinoxalinil, 5-Quinoxalinil, 6-Quinoxalinil, 1-Carbazolyl, 2-Carbazolyl, 3-Carbazolyl, 4-Carbazolyl, 9-Carbazolyl, Azacarbazolil-1-yl, Azacarbazolil-2-yl, Azacarbazolil-3-yl, Azacarbazolil-4-yl, Azacarbazolil-5-yl, Azacarbazolil-6-yl, Azacarbazolil-7-yl, Azacarbazolil-8-yl, Azacarbazolil-9-yl, 1-Phenantridinyl, 2-Phenantridinyl, 3-Phenantridinyl, 4-Phenantridinyl, 6-Phenantridinyl, 7-Phenantridinyl, 8-Phenantridinyl, 9-Phenantridinyl, 10-Phenantridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolil, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazinyl, 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-t-butylpyrrole-4-yl, 3-(2-phenylpropyl)pyrrole-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl,2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-naphtho-[1,2-b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-Naphtho-[1,2-b]-Benzofuranyl, 7-Naphtho-[1,2-b]-Benzofuranyl, 8-Naphtho-[1,2-b]-Benzofuranyl, 9-Naphtho-[1,2-b]-Benzofuranyl, 10-Naphtho-[1,2-b]-Benzofuranyl, 1-Naphtho-[2,3-b]-Benzofuranyl, 2-Naphtho-[2,3-b]-Benzofuranyl, 3-Naphtho-[2,3-b]-Benzofuranyl, 4-Naphtho-[2,3-b]-Benzofuranyl, 5-Naphtho-[2,3-b]-Benzofuranyl, 6-Naphtho-[2,3-b]-Benzofuranyl, 7-Naphtho-[2,3-b]-Benzofuranyl, 8-Naphtho-[2,3-b]-Benzofuranyl, 9-Naphtho-[2,3-b]-Benzofuranyl, 10-Naphtho-[2,3-b]-Benzofuranyl, 1-Naphtho-[2,1-b]-Benzofuranyl, 2-Naphtho-[2,1-b]-Benzofuranyl, 3-Naphtho-[2,1-b]-Benzofuranyl, 4-Naphtho-[2,1-b]-Benzofuranyl, 5-Naphtho-[2,1-b]-Benzofuranyl, 6-Naphtho-[2,1-b]-Benzofuranyl, 7-Naphtho-[2,1-b]-Benzofuranyl, 8-Naphtho-[2,1-b]-Benzofuranyl, 9-Naphtho-[2,1-b]-Benzofuranyl, 10-Naphtho-[2,1-b]-Benzofuranyl, 1-Naphtho-[1,2-b]-Benzothiophenyl, 2-Naphtho-[1,2-b]-Benzothiophenyl, 3-Naphtho-[1,2-b]-Benzothiophenyl, 4-Naphtho-[1,2-b]-Benzothiophenyl, 5-Naphtho-[1,2-b]-Benzothiophenyl, 6-Naphtho-[1,2-b]-Benzothiophenyl, 7-Naphtho-[1,2-b]-Benzothiophenyl, 8-Naphtho-[1,2-b]-Benzothiophenyl, 9-naphtho-[1,2-b]-benzothiophenyl, 10-naphtho-[1,2-b]-benzothiophenyl,1-Naphtho-[2,3-b]-benzothiophenyl, 2-Naphtho-[2,3-b]-benzothiophenyl, 3-Naphtho-[2,3-b]-benzothiophenyl, 4-Naphtho-[2,3-b]-benzothiophenyl, 5-Naphtho-[2,3-b]-benzothiophenyl, 1-Naphtho-[2,1-b]-benzothiophenyl, 2-Naphtho-[2,1-b]-benzothiophenyl, 3-Naphtho-[2,1-b]-benzothiophenyl, 4-Naphtho-[2,1-b]-benzothiophenyl, 5-Naphtho-[2,1-b]-benzothiophenyl, 6-Naphtho-[2,1-b]-benzothiophenyl, Examples include 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, etc. In this document, "halogen" includes F, Cl, Br, and I atoms.
[0030] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other; for example, in a benzene substituent, when the substituents are at the 1,2 position, it is called the ortho position. Meta indicates that two substituents are at the 1,3 position; for example, in a benzene substituent, when the substituents are at the 1,3 position, it is called the meta position. Para indicates that two substituents are at the 1,4 position; for example, in a benzene substituent, when the substituents are at the 1,4 position, it is called the para position.
[0031] In addition, in the descriptions of "substituted or non-substituted" as set forth herein, "substituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent).The substituents of the substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino and substituted arylheteroarylamino in the formulas of the present invention are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3-7 won)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)aryltio; (3-50 won)heteroaryl substituted or unsubstituted with one or more of (C1-C30)alkyl, (C6-C30)arylamino and di(C6-C30)arylamino; (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, cyano, (C1-C30)alkyl, (3-50 won)heteroaryl, di(C6-C30)arylamino and tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; One or more are selected from the group consisting of mono- or di- (C1-C30)alkylamino; mono- or di- (C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, and said substituents may be substituted with deuterium instead of hydrogen at any position.According to one embodiment of the present invention, the substituents are each independently one or more of deuterium, (C1-C6)alkyl, (C6-C25)aryl substituted or unsubstituted with deuterium, (5-15)heteroaryl, and di(C6-C12)arylamino. Specifically, the substituents may each independently be one or more of deuterium, methyl, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, spirobifluorenyl, phenanthrenyl, deuterium-substituted phenyl, naphthylphenyl, deuterium-substituted naphthyl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and diphenylamino.
[0032] In the formula of the present invention, when a ring is formed by connecting adjacent substituents, the ring may be a single ring or polycyclic ring of (3-30 members) that is substituted or unsubstituted and formed by connecting two or more adjacent substituents, and may be an alicyclic, aromatic, or combination thereof. Additionally, the formed ring may include one or more heteroatoms selected from B, N, O, S, Si, and P, preferably one or more heteroatoms selected from N, O, and S. According to one embodiment of the present invention, the number of ring skeleton atoms is (5-20 members), and according to another embodiment of the present invention, the number of ring skeleton atoms is (5-15 members).
[0033] In the present chemical formula, the heteroaryl may each independently include one or more heteroatoms selected from B, N, O, S, Si, and P. In addition, the heteroatom is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or One or more selected from the group consisting of unsubstituted (C1-C30)alkyl(C6-C30)arylaminos may be bonded.
[0034] According to one embodiment of the present invention, a plurality of host materials comprises a first host material comprising a compound represented by Chemical Formula 1 and a second host material comprising a compound represented by Chemical Formula 2, and may be included in the light-emitting layer of an organic electroluminescent device according to one embodiment of the present invention.
[0035] The compound represented by the above chemical formula 1 is described in more detail as follows.
[0036] In the above Chemical Formula 1, L1 can be connected to the parent nucleus at any position of the phenanthrene ring of the parent nucleus. Preferably, L1 is R 14 It can be connected to a connected benzene ring, and more preferably, R 14 It can be connected at position 2 or 3 of the connected benzene ring.
[0037] According to one example of the present invention, the compound represented by the above chemical formula 1 may be represented by one or more of the following chemical formulas 1-1 and 1-2.
[0038] [Chemical Formula 1-1] [Chemical Formula 1-2]
[0039]
[0040] In the above chemical formulas 1-1 and 1-2, X1, Y1, Ar1, L1, R 11 to R 14 and a to c are as defined in Chemical Formula 1.
[0041] In the above Chemical Formula 1, X1 and Y1 are each independently -N=, -NR 15 -, -O- or -S-, provided that one of X1 and Y1 is -N= and the other of X1 and Y1 is -NR 15 -, -O- or -S-. According to one embodiment of the present invention, if X1 is -N=, Y1 is -NR 15 If -, -O- or -S- and Y1 is -N=, then X1 is -NR 15 It may be -, -O- or -S-, and according to another embodiment of the present invention, if X1 is -N=, Y1 is -O- or -S-, and if Y1 is -N=, X1 may be -NR5-, -O- or -S-. In this case, R 15hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted It is a (C1-C30)alkyl(C6-C30)arylamino; or can form a ring by connecting to an adjacent substituent. According to one embodiment of the present invention, R 15 may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (3-30)heteroaryl, and according to another embodiment of the present invention, R 15 may be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C10)alkyl, or substituted or unsubstituted (C6-C25)aryl, and according to another embodiment of the present invention, R 15 It can be hydrogen or a substituted or unsubstituted (C6-C18)aryl.
[0042] In the above Chemical Formula 1, L1 is a single bond, or a substituted or unsubstituted (C6-C30)arylene. According to one embodiment of the present invention, L1 is a single bond, or a substituted or unsubstituted (C6-C25)arylene, and according to another embodiment of the present invention, L1 is a single bond, or a substituted or unsubstituted (C6-C18)arylene. Specifically, L1 may be a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, etc.
[0043] In the above chemical formula 1, Ar1 is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30)heteroarylamino. According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5-30)heteroaryl, a substituted or unsubstituted di(C6-C25)arylamino, or a substituted or unsubstituted (C6-C25)aryl(5-25)heteroarylamino, and according to another embodiment of the present invention, Ar1 is a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5-25)heteroaryl comprising at least one nitrogen, a substituted or unsubstituted di(C6-C18)arylamino, or a substituted or unsubstituted (C6-C18)aryl(5-18)heteroarylamino.Specifically, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzophenanthrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzoflurenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-fluorene]yl, substituted or unsubstituted spiro[dihydroindene-fluorene]yl, substituted or unsubstituted spiro[fluorene-benzofluren]yl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, At least one of the substituted aminos selected from the group consisting of substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, dibenzofuranyl, and dibenzothiophenyl may be substituted aminos, etc.
[0044] In the above chemical formula 1, R 11 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl. According to one aspect of the present invention, R 11 is a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5-25)heteroaryl, and according to another aspect of the present invention, R 11 is a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5-18)heteroaryl. Specifically, R 11 It may be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, etc.
[0045] In the above chemical formula 1, R 12 to R14 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted It is a (C1-C30)alkyl(C6-C30)arylamino; or can form a ring by connecting to an adjacent substituent. According to one embodiment of the present invention, R 12 to R 14 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C10)alkyl, substituted or unsubstituted (C6-C25)aryl, or substituted or unsubstituted (5-25 group)heteroaryl, and according to another aspect of the present invention, R 12 to R 14 Each is independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted (C1-C10)alkyl.
[0046] a and b are each independently 1 or 2, c is an integer from 1 to 3, and if a to c are integers of 2 or more, each R 12 to R 14 They may be the same or different from each other.
[0047] The compound represented by the above chemical formula 1 may be one or more selected from the following compounds, but is not limited to these.
[0048]
[0049]
[0050]
[0051]
[0052]
[0053]
[0054]
[0055]
[0056]
[0057]
[0058]
[0059]
[0060]
[0061]
[0062]
[0063]
[0064]
[0065]
[0066]
[0067]
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074]
[0075]
[0076]
[0077]
[0078]
[0079]
[0080] The compound represented by the above chemical formula 2 is described in more detail as follows.
[0081] In the above chemical formula 2, HAr is a substituted or unsubstituted (3-30) heteroaryl containing a nitrogen atom. According to one embodiment of the present invention, HAr is a substituted or unsubstituted (5-15) heteroaryl containing a nitrogen atom. According to another embodiment of the present invention, HAr is a (5-15) heteroaryl containing a nitrogen atom and substituted or unsubstituted with a (C6-C20) aryl, wherein the (C6-C20) aryl is substituted or unsubstituted with a deuterium. Specifically, HAr may be substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naftiridinyl, or substituted or unsubstituted benzothienopyrimidinyl, etc. In addition, for example, HAr is a substituted triazinyl, wherein the substituent of the substituted triazinyl may be one or more, preferably two, of phenyl, naphthyl, biphenyl, terphenyl, deuterium-substituted phenyl, naphthylphenyl, deuterium-substituted naphthyl, and phenylnaphthyl.
[0082] In the above formula 2, L2 is a single bond, or a substituted or unsubstituted (C6-C30)arylene. According to one embodiment of the present invention, L2 is a single bond, or a (C6-C18)arylene substituted or unsubstituted with deuterium and / or (C1-C6)alkyl. Specifically, L2 may be a single bond, a deuterium-substituted or unsubstituted phenylene, a deuterium-substituted or unsubstituted naphthylene, a deuterium-substituted or unsubstituted biphenylene, a deuterium-substituted or unsubstituted terphenylene, or a deuterium-substituted or unsubstituted phenylene-naphthylene, etc.
[0083] In the above chemical formula 2, R1 to R8 are each independently a (C6-C30)aryl substituted or unsubstituted with hydrogen, deuterium, or deuterium. According to one embodiment of the present invention, R1 to R8 are each independently a (C6-C18)aryl substituted or unsubstituted with hydrogen, deuterium, or deuterium. Specifically, R1 to R8 may each independently be hydrogen, deuterium, phenyl, naphthyl, biphenyl, phenyl substituted with deuterium, etc.
[0084] The compound represented by the above chemical formula 2 may be one or more selected from the following compounds, but is not limited to these.
[0085]
[0086]
[0087]
[0088]
[0089]
[0090]
[0091]
[0092]
[0093]
[0094]
[0095]
[0096]
[0097]
[0098]
[0099]
[0100]
[0101]
[0102]
[0103]
[0104]
[0105]
[0106]
[0107]
[0108]
[0109]
[0110]
[0111]
[0112]
[0113] One or more of the above compounds H1-1 to H1-160 and one or more of the above compounds H2-1 to H2-139 can be combined and used in an organic electroluminescent device.
[0114] The compound represented by Chemical Formula 1 of the present invention can be prepared by synthesis methods known to those skilled in the art, for example, by referring to Korean Patent Publication No. 2017-0022865 (published March 2, 2017), but is not limited thereto.
[0115] The compound represented by Chemical Formula 2 of the present invention can be prepared by synthesis methods known to those skilled in the art, for example, as shown in the reaction scheme below, but is not limited thereto.
[0116] [Reaction Equation 2]
[0117]
[0118] R1 to R8, L2, and HAr are the same as defined in Chemical Formula 2, and Hal is a halogen.
[0119] In addition, non-deuterated analogs of the compound represented by Formula 2 can be prepared by known coupling and substitution reactions, and deuterated analogs can be prepared in a similar manner using a deuterated precursor material, or more generally by treating the non-deuterated compound with a deuterated solvent, D6-benzene, in the presence of a Lewis acid such as aluminum trichloride or ethyl aluminum chloride, or an H / D exchange catalyst such as trifluoromethanesulfonic acid or trifluoromethanesulfonic acid-D. In addition, the degree of deuteration can be controlled by varying reaction conditions, such as the reaction temperature. For example, the degree of deuteration in Formula 2 can be controlled by adjusting the reaction temperature and time, the acid equivalent, etc.
[0120] An organic electroluminescent device according to the present invention comprises an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may comprise a plurality of organic electroluminescent materials, wherein the organic layer comprises a compound represented by Formula 1 as a first organic electroluminescent material and a compound represented by Formula 2 as a second organic electroluminescent material. According to one embodiment of the present invention, an organic electroluminescent device according to the present invention comprises an anode, a cathode, and at least one emitting layer between the anode and the cathode, wherein the emitting layer may comprise a compound represented by Formula 1 and a compound represented by Formula 2.
[0121] The light-emitting layer comprises a host and a dopant, and the host comprises a plurality of host materials, and the compound represented by Chemical Formula 1 may be included as a first host compound among the plurality of host materials, and the compound represented by Chemical Formula 2 may be included as a second host compound among the plurality of host materials. Here, the weight ratio of the first host compound and the second host compound is about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to 60:40, and even more preferably about 50:50.
[0122] In the present invention, the light-emitting layer may be a single layer as a layer in which light is emitted, or it may be a plurality of layers in which two or more layers are stacked. Among the plurality of host materials of the present invention, the first and second host materials may both be included in a single layer, or the first and second host materials may each be included in different light-emitting layers. According to one aspect of the present invention, the doping concentration of the dopant compound for the host compound of the light-emitting layer may be less than 20 weight%.
[0123] The organic electroluminescent device of the present invention may further include one or more layers selected from a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron transport layer, an electron injection layer, an interlayer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present invention, the organic electroluminescent device of the present invention may further include one or more amine-based compounds among a hole injection material, a hole transport material, a hole assist material, a light-emitting material, a light-emitting assist material, and an electron blocking material, in addition to the plurality of host materials of the present invention. Furthermore, according to one embodiment of the present invention, the organic electroluminescent device of the present invention may further include one or more azine-based compounds among an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material, in addition to the plurality of host materials of the present invention.
[0124] The multiple types of host materials according to the present invention can be used as light-emitting materials for a White Organic Light Emitting Device. Various structures of the White Organic Light Emitting Device are proposed, such as a side-by-side arrangement, a stacking arrangement, or a color conversion material (CCM) arrangement, depending on the arrangement of R (red), G (green), YG (yellow-green), and B (blue) light-emitting parts. In addition, the multiple types of host materials according to one example can also be used in an organic light-emitting device containing quantum dots (QDs).
[0125] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the emissive layer. Multiple layers of the hole injection layer may be used to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, and two compounds may be used simultaneously in each layer. Additionally, the hole injection layer may be doped with a p-dopant. The electron blocking layer is located between the hole transport layer (or hole injection layer) and the emissive layer and can prevent light leakage by blocking the overflow of electrons from the emissive layer and trapping excitons within the emissive layer. Multiple layers of the hole transport layer or electron blocking layer may be used, and multiple compounds may be used in each layer.
[0126] 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 emitting layer and the cathode. Multiple layers of the electron buffer layer may be used to control electron injection and improve interface characteristics between the emitting layer and the electron injection layer, and two compounds may be used simultaneously in each layer. Multiple layers of the hole blocking layer or electron transport layer may also be used, and multiple compounds may be used in each layer. Additionally, the electron injection layer may be doped with an n-dopant.
[0127] One or more phosphorescent or fluorescent dopants may be used as dopants included in the organic electroluminescent device of the present invention, and a phosphorescent dopant is preferred. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but may be a complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, preferably, may be an orthometallated complex compound of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and in some cases, more preferably, may be an orthometallated iridium complex compound.
[0128] A compound represented by the following chemical formula 101 may be used as a dopant included in the organic electroluminescent device of the present invention, but is not limited thereto.
[0129] [Chemical Formula 101]
[0130]
[0131] In the above chemical formula 101,
[0132] L is selected from the following structure 1 or 2;
[0133] [Structure 1] [Structure 2]
[0134]
[0135] R 100 to R 103Each is independently a (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3-30)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy, which is hydrogen, deuterium, halogen, deuterium and / or halogen substituted or unsubstituted (C1-C30)alkoxy; and can be connected to adjacent substituents to form a ring, and, for example with pyridine, can form a substituted or unsubstituted quinoline, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothyenopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothyenoquinoline, or substituted or unsubstituted indenopyridine;
[0136] R 104 to R 107 Each is independently a (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy, which is a hydrogen, deuterium, halogen, deuterium and / or halogen-substituted (C1-C30)alkoxy; and can be connected to adjacent substituents to form a ring, for example, with benzene to form a substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopuropyridine, or substituted or unsubstituted benzothienopyridine;
[0137] R 201 to R 211 Each is independently a (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl, which is a hydrogen, deuterium, halogen, deuterium and / or halogen; and may be connected to an adjacent substituent to form a ring;
[0138] s is an integer from 1 to 3.
[0139] Specifically, specific examples of the above-mentioned dopant compounds are as follows, but are not limited thereto.
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157]
[0158]
[0159]
[0160]
[0161]
[0162]
[0163]
[0164] Each layer of the organic electroluminescent device of the present invention can be formed by any one of dry film deposition methods such as vacuum deposition, sputtering, plasma, or ion plating, or wet film deposition methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, or flow coating.
[0165] In the case of the wet film deposition method, a thin film is formed by dissolving or dispersing the material forming each layer in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. Any solvent may be used as long as the material forming each layer can be dissolved or dispersed and there is no problem with film formation properties.
[0166] In addition, the first and second host compounds of the present invention can be deposited using the methods listed above, and commonly, they can be deposited by a co-deposition or mixed deposition process. The co-deposition is a method of mixed deposition in which two or more materials are placed in separate crucible sources and current is applied to two cells simultaneously to evaporate the materials, and the mixed deposition is a method of mixed deposition in which two or more materials are mixed in a single crucible source before deposition and then current is applied to one cell to evaporate the materials. In addition, when the first and second host compounds exist in the same layer or different layers within an organic electroluminescent device, the two host compounds can be deposited individually. For example, the second host compound can be deposited after the first host compound has been deposited.
[0167] The present invention can provide a display device using a plurality of host materials comprising a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. That is, it is possible to manufacture a display device or a lighting device using the plurality of host materials of the present invention. Specifically, it is possible to manufacture a display device, for example, a white organic light-emitting device, a smartphone, a tablet, a laptop, a PC, a TV, or a display device for a vehicle, or a lighting device, for example, an outdoor or indoor lighting device, using the plurality of host materials of the present invention.
[0168] In the following, for a detailed understanding of the present invention, representative compounds of the present invention are cited to examine the method for manufacturing the compounds according to the present invention, the physical properties thereof, and the characteristics of an OLED device comprising multiple types of host materials according to the present invention. However, the following examples are merely intended to explain the characteristics of the compounds according to the present invention and the OLED devices comprising multiple types of host materials according to the present invention for a detailed understanding of the present invention, and the present invention is not limited to the following examples.
[0169] [Synthesization Example 1] Synthesis of Compound H1-147
[0170]
[0171] Compound in the reaction vessel A(CAS: 2085325-18-2, 4.0 g, 9.5 mmol), 2-chloro-3-phenylquinoxaline (2.8 g, 11.4 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.5 g, 0.5 mmol), potassium carbonate (K2CO3) (2.0 g, 19 mmol), 30 mL of toluene, 7 mL of EtOH, and 10 mL of water were added, and the mixture was stirred under reflux for one day. After the reaction was complete, the mixture was cooled to room temperature, filtered through a Celite filter using methylene chloride (MC), subjected to vacuum distillation, and then separated into compounds using methylene chloride / hexane (MC / Hex) column chromatography. H1-147 (2.7 g, yield: 57%) was obtained.
[0172]
[0173] [Synthesization Example 2] Synthesis of Compound H1-146
[0174]
[0175] Compound in the reaction vessel A (23.8 g, 56.6 mmol), 2-chloro-4-(naphthalene-1-yl)-6-phenyl-1,3,5-triazine (15.0 g, 47.2 mmol), Pd(PPh3)4 (2.72 g, 2.36 mmol), K2CO3 (16.3 g, 118 mmol), 240 mL of toluene, 60 mL of EtOH, and 60 mL of purified water were added, and the mixture was refluxed and stirred for 2 hours. After the reaction was complete, the mixture was cooled to room temperature and separated using a silica filter. The organic layer was subjected to vacuum distillation, and the compound was recrystallized with toluene. H1-146 (13.8 g, yield: 51%) was obtained.
[0176]
[0177] [Synthesization Example 3] Synthesis of Compound H1-157
[0178]
[0179] Compound in the reaction vessel A (4.0 g, 9.5 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (3.9 g, 11.4 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (2.6 g, 19 mmol), 30 mL of toluene, 7 mL of EtOH, and 10 mL of purified water were added, and the mixture was refluxed and stirred for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and stirred at room temperature. Methanol (MeOH) was added, the resulting solid was filtered under reduced pressure, and the compound was separated by MC column chromatography. H1-157 (4.6 g, yield: 80%) was obtained.
[0180]
[0181] [Synthesization Example 4] Synthesis of Compound H1-145
[0182]
[0183] Compound in the reaction vessel A 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (3.4 g, 9.26 mmol), Pd(PPh3)4 (0.4 g, 0.36 mmol), K2CO3 (2.0 g, 14 mmol), 36 mL of toluene, 8 mL of EtOH, and 12 mL of purified water were added, and the mixture was refluxed and stirred for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, stirred at room temperature, and MeOH was added. The resulting solid was filtered under reduced pressure, and the compound was separated by MC column chromatography. H1-145 (3.3 g, yield: 75%) was obtained.
[0184]
[0185] [Synthesization Example 5] Synthesis of Compound H1-156
[0186]
[0187] Compound in the reaction vessel A(4.0 g, 9.5 mmol), 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine (3.6 g, 11.4 mmol), Pd(PPh3)4 (0.5 g, 0.5 mmol), K2CO3 (2.6 g, 19 mmol), 30 mL of toluene, 7 mL of EtOH, and 10 mL of purified water were added, and the mixture was refluxed and stirred for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, stirred at room temperature, and MeOH was added. The resulting solid was filtered under reduced pressure, and the compounds were separated by MC column chromatography. H1-156 (3.45 g, yield: 63%) was obtained.
[0188]
[0189] [Synthesizing Example 6] Preparation of Compound H1-51
[0190]
[0191] Compound in the reaction vessel 1-1 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]amine (6.8 g, 13 mmol), palladium(II) acetate (Pd(OAc)2) (0.3 g, 1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl(s-Phos) (0.9 g, 2 mmol), cesium carbonate (Cs2CO3) (11.5 g, 35 mmol), 60 mL of o-xylene, 15 mL of ethanol (EtOH), and 15 mL of distilled water were added, and the mixture was refluxed and stirred at 150°C for 3 hours. After the reaction is complete, the compound is washed with distilled water, extracted with ethyl acetate, dried with magnesium sulfate to remove the solvent using a rotary evaporator, and purified by column chromatography. H1-51 (2.2 g, yield: 27%) was obtained.
[0192]
[0193] [Synthesizing Example 7] Preparation of Compound H1-80
[0194]
[0195] Compound in the reaction vessel 2-1 N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (4.8 g, 11.34 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.4 g, 0.34 mmol), sodium carbonate (Na2CO3) (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added, and the mixture was stirred at 120°C for 4 hours. After the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by recrystallization using column chromatography to obtain the compound H1-80 (1.4 g, yield: 20.0%) was obtained.
[0196]
[0197] [Synthesizing Example 8] Preparation of Compound H1-158
[0198]
[0199] Compound in the reaction vessel 2-1 After adding 2-chloro-4,6-diphenyltriazine (CAS: 3842-55-5, 5.8 g, 21.6 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.2 g, 1.0 mmol), potassium carbonate (K2CO3) (7.5 g, 59 mmol), 90 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water, the mixture was stirred at 120°C for 4 hours. Once the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by recrystallization using column chromatography to obtain the compound H1-158 (5.7 g, yield: 50%) was obtained.
[0200]
[0201] [Synthesization Example 9] Preparation of Compound H1-102
[0202]
[0203] Compound in the reaction vessel 2-1 After adding 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (CAS: 1472062-94-4, 3.53 g, 9.1 mmol), tetrakis(triphenylphosphine)palladium (0.48 g, 0.41 mmol), sodium carbonate (2.2 g, 20.7 mmol), 28 mL of toluene, 7 mL of ethanol, and 7 mL of distilled water, the mixture was stirred at 120°C for 5 hours. Once the reaction was complete, the mixture was added dropwise to methanol, and the resulting solid was filtered. The resulting solid was purified by recrystallization using column chromatography to obtain the compound H1-102 (3.7 g, yield: 74%) was obtained.
[0204]
[0205] [Synthesizing Example 10] Preparation of Compound H2-22
[0206]
[0207] 1) Synthesis of Compound 3-1
[0208] 2-chloro-4,6-di(naphthalene-2-yl)-1,3,5-triazine (20 g, 79.7 mmol), (4-bromonaphthalene-1-yl)boronic acid (32.2 g, 87.7 mmol), Pd(PPh3)4 (4.6 g, 3.985 mmol), Cs2CO3 (65 g, 199.25 mmol), and 400 mL of toluene were added to a flask, dissolved, and refluxed and stirred for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, the mixture was dried, and the compounds were separated using column chromatography. 3-1 (30 g, yield: 74%) was obtained.
[0209] 2) Synthesis of Compound H2-22
[0210] Compound in the flask 3-190 mL of sodium tert-butoxide (4.3 g, 44.75 mmol), 9H-carbazole (3.0 g, 17.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.8 g, 0.9 mmol), dicyclohexylphosphino-2',6'-dimethoxybiphenyl(s-phos) (0.73 g, 1.79 mmol), sodium tert-butoxide (4.3 g, 44.75 mmol), and xylene were added and dissolved, then refluxed and stirred for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate and separated by column chromatography to obtain the compounds. H2-22 (1.5 g, yield: 13%) was obtained.
[0211]
[0212] [Synthesizing Example 11] Preparation of Compound H2-115
[0213]
[0214] 1) Synthesis of Compound 3-2
[0215] 4-bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), Na2CO3 (13 g, 121.8 mmol), 200 mL of toluene, 100 mL of ethanol, and 100 mL of water were added to a flask, dissolved, and refluxed and stirred for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, the mixture was dried, and the compounds were separated using column chromatography. 3-2 (9 g, yield: 91%) was obtained.
[0216] 2) Synthesis of Compound H2-115
[0217] Compound in the flask 3-1 (8.5 g, 13.5 mmol), compound 3-260 mL of (3.0 g, 12.3 mmol), Pd2(dba)3 (0.56 g, 0.615 mmol), s-phos (0.51 g, 1.23 mmol), NaOtBu (2.9 g, 30.75 mmol), and o-xylene were added and dissolved, then refluxed and stirred for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate and separated by column chromatography to obtain the compounds. H2-115 (2.8 g, yield: 32.5%) was obtained.
[0218]
[0219] [Synthesizing Example 12] Preparation of Compound H2-14
[0220]
[0221] 4-phenyl-9H-carbazole (3.0 g, 12.3 mmol), 2-(4-bromonaphthalene-1-yl)-4,6-diphenyl-1,3,5-triazine (5.4 g, 12.3 mmol), Pd2(dba)3 (0.56 g, 0.62 mmol), s-phos (0.51 g, 1.23 mmol), NaOtBu (2.4 g, 24.7 mmol), and 62 mL of o-xylene were added to a flask, dissolved, and refluxed and stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and MeOH was added while stirring at room temperature. The resulting solid was filtered under reduced pressure, extracted using MC / Hex, and separated by column chromatography to obtain the compound. H2-14 (3.3 g, yield: 45%) was obtained.
[0222]
[0223] [Synthesizing Example 13] Preparation of Compound H2-16
[0224]
[0225] Compound in the flask B8.0 g, 16.4 mmol (9H-carbazole), 3.0 g, 18.0 mmol, Pd2(dba)3 (0.8 g, 0.8 mmol), s-phos (0.7 g, 1.64 mmol), NaOtBu (2.4 g, 24.6 mmol), and 82 mL of o-xylene were added and dissolved, then refluxed and stirred for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate and separated by column chromatography to obtain the compounds. H2-16 (6.0 g, yield: 69%) was obtained.
[0226]
[0227] [Synthesizing Example 14] Preparation of Compound H2-116
[0228]
[0229] 1) Synthesis of Compound 3-3
[0230] 1-Bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (6.2 g, 48.7 mmol), Pd(PPh3)4 (2.3 g, 2.03 mmol), Na2CO3 (13 g, 121.8 mmol), 200 mL of toluene, 100 mL of ethanol, and 100 mL of water were added to a flask, dissolved, and refluxed and stirred for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was extracted with ethyl acetate, residual moisture was removed using magnesium sulfate, the mixture was dried, and the compounds were separated using column chromatography. 3-3 (9 g, yield: 96%) was obtained.
[0231] 2) Synthesis of Compound H2-116
[0232] Compound in the flask 3-3 (3.0 g, 12.3 mmol), compound B8 g (18.5 mmol), Cu powder (0.39 g, 6.15 mmol), K2CO3 (3.4 g, 24.6 mmol), and 60 mL of dichlorobenzene (DCB) were added and dissolved, then refluxed and stirred for 24 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and MeOH was added while stirring at room temperature to filter the resulting solid under reduced pressure. The solid was then extracted using MC / Hex and separated by column chromatography to obtain the compound. H2-116 (1.1 g, yield: 14.8%) was obtained.
[0233]
[0234] [Device Examples 1 and 2] Preparation of an OLED in which a plurality of host materials according to the present invention are deposited as a host
[0235] An OLED according to the present invention was manufactured. First, a transparent electrode ITO thin film (10Ω / □) on an OLED glass substrate (manufactured by Geomatec) was ultrasonically cleaned using acetone and isopropyl alcohol sequentially, and then stored in isopropyl alcohol before use. Next, the ITO substrate was mounted on the substrate holder of a vacuum deposition apparatus, and then the compound of Table 2 below was placed in the cell inside the vacuum deposition apparatus. HI-1 Insert, and in another cell, the compounds in Table 2 below. HT-1 After adding, the two substances are evaporated at different rates to form a compound HI-1 and compounds HT-1 Compounds regarding the total amount of HI-1 A first hole injection layer was deposited by doping with an amount of 3 wt% to a thickness of 10 nm. Subsequently, the compound HT-1 A compound was deposited on the first hole injection layer to form a first hole transport layer with a thickness of 80 nm. Subsequently, a compound was placed in another cell within the vacuum deposition equipment. HT-2[...] was added, and current was applied to the cell to evaporate it, thereby depositing a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, an emissive layer was deposited thereon as follows. The first host compound and the second host compound listed in Table 1 below were respectively placed as hosts in two locations within the vacuum deposition apparatus, and in another cell, the compound D-39 After adding, a 40 nm thick emissive layer was deposited on the second hole transport layer by evaporating the two host materials at a 1:1 rate and simultaneously evaporating the dopant material at a different rate, thereby doping the dopant to an amount of 3 wt% relative to the total amount of the host and dopant. Subsequently, a compound was placed on the emissive layer as an electron transport material. ET-1 and compounds EI-1 The compound was deposited to a thickness of 35 nm at a weight ratio of 50:50. Subsequently, the compound was applied as the electron injection layer. EI-1 After depositing the above electron transport layer to a thickness of 2 nm, an OLED was fabricated by depositing an Al cathode to a thickness of 80 nm on the electron injection layer using a different vacuum deposition equipment. For each material, each compound was 10 -6 It was purified by vacuum sublimation under torr conditions and used.
[0236] [Comparative Example] Preparation of an OLED containing a comparative compound as a host
[0237] An OLED was manufactured in the same manner as device Examples 1 and 2, except that the second host compound listed in Table 1 was used alone as the host of the light-emitting layer.
[0238] The driving voltage, luminous efficiency, luminous color at 1,000 nit brightness, and the time taken for the light intensity at 5,500 nit brightness to drop from 100% to 95% (lifetime: T95) of the organic electroluminescent devices of Examples 1 and 2 and Comparative Example manufactured as described above were measured and are shown in Table 1 below.
[0239] [Table 1]
[0240]
[0241] From Table 1 above, it can be confirmed that an organic electroluminescent device comprising a specific combination of compounds according to the present invention as a host material can significantly lower the driving voltage compared to a conventional organic electroluminescent device using a single host material (comparative example), and that the luminous efficiency and lifespan characteristics are significantly improved.
[0242] [Table 2]
[0243]
Claims
Claim 1 A plurality of host materials comprising a first host material comprising a compound represented by the following chemical formula 1, and a second host material comprising a compound represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, X1 is -N=; Y1 is -O- or -S-; L1 is a single bond, or a substituted or unsubstituted (C6-C30)arylene; Ar1 is a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or a substituted or unsubstituted (C6-C30)aryl(3-30)heteroarylamino; and R 11 is a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3-30)heteroaryl; R 12 to R 14 Each is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; can be connected to adjacent substituents to form a ring; a and b are each independently 1 or 2, c is an integer from 1 to 3, and if a to c are integers of 2 or more, each R 12 to R 14 They may be identical or different from each other; [Chemical Formula 2] In the above Chemical Formula 2, HAr is substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzisoquinolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted naphthiridinyl, or substituted or unsubstituted benzothienopyrimidinyl; L2 is substituted or unsubstituted (C10-C30)arylene; R1 to R8 are each independently (C6-C30)aryl substituted or unsubstituted with hydrogen, deuterium, or deuterium; provided that the first host material and the second host material are mutually It is different. Claim 2 In paragraph 1, Ar1, L1, L2, HAr, and R 11 to R 15 The substituents of the substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, substituted arylheteroarylamino, substituted triazinyl, substituted pyridyl, substituted pyrimidinyl, substituted quinazolinyl, substituted benzoquinazolinyl, substituted benzoquinoxalinyl, substituted quinolyl, substituted benzoquinolyl, substituted isoquinolyl, substituted benzisoquinolyl, substituted triazolyl, substituted pyrazolyl, substituted naphthiridinyl, and substituted benzothienopyrimidinyl are each independently 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; (3-7)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3-50)heteroaryl substituted or unsubstituted with one or more of (C1-C30)alkyl, (C6-C30)aryl and di(C6-C30)arylamino; (C6-C30)aryl substituted or unsubstituted with one or more of deuterium, cyano, (C1-C30)alkyl, (3-50)heteroaryl, di(C6-C30)arylamino, and tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)aryl carbonyl; di(C6-C30)aryl boronyl; di(C1-C30)alkyl boronyl; (C1-C30)alkyl(C6-C30)aryl boronyl;A plurality of host materials, each being one or more selected from the group consisting of (C6-C30)ar(C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl. Claim 3 In claim 1, a plurality of host materials, wherein the compound represented by Chemical Formula 1 is represented by one or more of the following Chemical Formulas 1-1 and 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, X1, Y1, Ar1, L1, R 11 to R 14 and a to c are as defined in paragraph 1. Claim 4 A plurality of host materials according to claim 1, wherein in the above formula 1, Ar1 is at least one substituted amino selected from the group consisting of substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, dibenzofuranyl, and dibenzothiophenyl. Claim 5 A plurality of host materials according to claim 1, wherein in the above formula 2, HAr is substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazolyl, or substituted or unsubstituted pyrazolyl; and L2 is deuterium-substituted or unsubstituted naphthylene, deuterium-substituted or unsubstituted biphenylene, deuterium-substituted or unsubstituted terphenylene, or deuterium-substituted or unsubstituted phenylene-naphthylene. Claim 6 A plurality of host materials, wherein the compound represented by Chemical Formula 1 is one or more selected from the following compounds. Claim 7 A plurality of host materials, wherein the compound represented by Chemical Formula 2 is one or more selected from the following compounds. Claim 8 An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one of the light-emitting layers comprises a plurality of host materials as described in claim 1.
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