Multiple host material and organic electroluminescent device including the same
A combination of host materials in OLEDs, represented by Formulas 1 and 2, addresses the issues of high voltage and low efficiency in OLEDs, resulting in improved performance and longevity.
Patent Information
- Application Number
- JP2024083858
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-17
- Filing Date
- 2024-05-23
- Publication Date
- 2024-12-25
AI Technical Summary
Existing organic electroluminescent devices (OLEDs) face challenges with high driving voltage, low luminous efficiency, and insufficient lifetime, particularly in applications like TVs and lighting, necessitating host materials that can improve these performance metrics.
The use of a first host material represented by Formula 1 and a second host material represented by Formula 2, which are combined in various ratios to form a plurality of host materials, enhancing the performance of organic electroluminescent devices by reducing driving voltage and improving luminous efficiency and lifetime.
The combination of host materials achieves low driving voltage, high luminous efficiency, and excellent lifetime characteristics in OLEDs, outperforming conventional host combinations in terms of operational stability and efficiency.
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Abstract
Description
[Technical field]
[0001] The present disclosure relates to a number of host materials and organic electroluminescent devices containing same. [Background technology]
[0002] In 1987, Tang et al. at Eastman Kodak developed a small molecule green organic electroluminescent device (OLED) by using a TPD / Alq3 bilayer consisting of an emitting layer and a charge transport layer. Since then, the development of OLEDs has progressed rapidly, and OLEDs have been commercialized. Currently, OLEDs mainly use phosphorescent materials with excellent luminous efficiency in panel packaging. However, in many applications such as TV and lighting, the OLED lifetime is insufficient, and higher efficiency of OLEDs is still required. Typically, as the brightness of OLEDs increases, the lifetime of OLEDs decreases. Therefore, OLEDs with high luminous efficiency and / or long lifetime are required for long-term use and high display resolution.
[0003] In order to improve the luminous efficiency, driving voltage, and / or life span, various materials or concepts have been proposed for the organic layer of OLED. However, they have not been satisfactory in practical use. In addition, there is a need to develop organic electroluminescent materials with improved performance, such as improved driving voltage, luminous efficiency, power efficiency, and / or life span characteristics, compared with the combination of specific compounds previously disclosed.
[0004] On the other hand, Patent Document 1 discloses a compound having a condensed structure containing benzocarbazole and azulene, and a compound having a condensed structure containing indolocarbazole and azepine as a host material. However, the above-mentioned reference does not specifically disclose a plurality of host materials including a specific combination of compounds according to the present disclosure. [Prior art documents] [Patent documents]
[0005] [Patent Document 1] Korean Patent Application Publication No. 2020-0014189 [Patent Document 2] Korean Patent Application Publication No. 2018-0021961 [Patent Document 3] Korean Patent Application Publication No. 2018-0012709 Summary of the Invention [Problem to be solved by the invention]
[0006] The object of the present disclosure is, first, to provide a plurality of host materials that enable the provision of an organic electroluminescent device having a low driving voltage, and / or a high luminous efficiency, and / or an excellent life characteristic, and, second, to provide an organic electroluminescent device including those host materials. [Means for solving the problem]
[0007] As a result of intensive research to solve the technical problems, the present inventors have found that the above object can be achieved by a plurality of host materials including a first host material containing a compound represented by the following formula 1 and a second host material containing a compound represented by the following formula 2: [ka]
[0008] In formula 1, L1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar1 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, -N-(L2-Ar2)(L3-Ar3), a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; [ka] is represented by the following formula 1-1 or 1-2: [ka] It is expressed as:
[0009] In formulas 1-1 and 1-2, X1~X 25 are each independently N or CR a represents R aare each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl. 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, or may be linked to adjacent substituents to form a ring; * indicates the position where it is linked to L1. [ka]
[0010] In formula 2, X represents O or S; L4 and L5 each independently represent a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar4 and Ar5 each independently represent a substituted or unsubstituted (C6 to C30) aryl or a substituted or unsubstituted (3 to 30 membered) heteroaryl; R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -SiR 11 R 12 R 13 represents; a represents an integer of 1 to 4, b represents an integer of 1 to 3, and when a and b each represent an integer of 2 or more, each R1 and each R2 may be the same as or different from each other.
[0011] Advantageous Effects of the Invention By using several host materials of the present disclosure, organic electroluminescent devices having low driving voltage, high luminous efficiency, and / or excellent life characteristics can be fabricated. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0012] The present disclosure will be described in detail below. However, the following description is intended to explain the present disclosure, and is in no way intended to limit the scope of the present disclosure.
[0013] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any layer that makes up the organic electroluminescent device.
[0014] The term "organic electroluminescent material" in the present disclosure means a material that can include at least one compound that can be used in an organic electroluminescent device. The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device as necessary. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary 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.
[0015] The term "multiple host materials" in the present disclosure means a host material that includes a combination of at least two compounds that can be included in any light-emitting layer that constitutes an organic electroluminescent device. It can mean both the material before being included in an organic electroluminescent device (e.g., before deposition) and the material after being included in an organic electroluminescent device (e.g., after deposition). For example, the multiple host materials of the present disclosure are a combination of at least two host materials, and can optionally further include conventional materials that are included in organic electroluminescent materials. The at least two compounds included in the multiple 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 host materials can be mixed and evaporated or co-evaporated, or can be evaporated separately.
[0016] In this specification, the term "(C1-C30) alkyl" means a straight or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 10, more preferably 1 to 6. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, and the like.
[0017] As used herein, the term "(C3-C30)cycloalkyl" refers to a mono- or poly-cyclic hydrocarbon having 3 to 30 ring skeletal carbon atoms, where the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7. Said cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like.
[0018] The term "(3- to 7-membered)heterocycloalkyl" is intended to mean a cycloalkyl having 3 to 7 skeletal ring atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N. The heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like.
[0019] The terms "(C6-C30)aryl" and "(C6-C30)arylene" refer to a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 skeletal carbon atoms. The aryl and arylene may be partially saturated. The aryl may include a spiro structure. The aryl may include phenyl, biphenyl, terphenyl, quinquephenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, benzophenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorenyl]yl, spiro[cyclopentene-fluorenyl]yl, spiro[dihydroindene-fluorenyl]yl, azulenyl, tetramethyldihydrophenanthrenyl, and the like. Specifically, the above aryl includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, fluoranyl, 4-fluorenyl, 9-fluoranyl, benzo[a]fluorenyl, benzo[b]fluorenyl, benzo[c]fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-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, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl,p-Tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9- Diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 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, 11,1 1-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, 1 1,11-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, 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 nyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl-6-benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthrenyl,These may include 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthrenyl, 9,9,10,10-tetramethyl-9,10-dihydro-4-phenanthrenyl, and the like.
[0020] The term "(3- to 30-membered)heteroaryl" or "(3- to 30-membered)heteroarylene" refers to an aryl group having 3 to 30 ring skeletal atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is preferably 1 to 4. The heteroaryl may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, may be formed by binding at least one heteroaryl or aryl group to the heteroaryl group via a single bond, and may include a spiro structure. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzothiophenyl, naphthoxazolyl, benzofuroquinolinyl, benzofuroquinazolinyl, benzofuronaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, benzothienoquinolinyl, benzothienoquinazolinyl, naphthyridinyl, benzothienonaphthyridinyl, and benzothienopyrimidinyl. midinyl, naphthothienopyrimidinyl, pyrimidoindolyl, benzopyrimidoindolyl, benzofuropyrazinyl, naphthofuropyrazinyl, benzothienopyrazinyl, naphthothienopyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridyl, chromenoquinazolinyl, thiochromenoquinazolinyl,Examples of condensed ring heteroaryls include dimethylbenzopyrimidinyl, indolocarbazolyl, indenocarbazolyl, etc. More specifically, the heteroaryls include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, and 7-indolizidinyl. , 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl , 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 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-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]-benzo furanyl, 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 1-naphtho-[1,2-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, 7-naphtho-[2,1-b]-benzothiophenyl, 8-naphtho-[2,1-b]-benzothiophenyl, 9-naphtho-[2,1-b]-benzothiophenyl, 10-naphtho-[2,1-b]-benzothiophenyl, 2-benzofuro[3,2-d]pyrimidinyl, 6-benzofuro[3,2-d]pyrimidinyl, 7-benzofuro[3,2-d]pyrimidinyl, 8-benzofuro[3,2-d]pyrimidinyl, 9-benzofuro[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl,6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofuro[3,2-d]pyrazinyl, 6-benzofuro[3,2-d]pyrazinyl, 7-benzofuro[3,2-d]pyrazinyl, 8-benzofuro[3,2-d]pyrazinyl, 9-benzofuro[3,2-d]pyrazinyl, 2-benzothio[3,2-d]pyrazinyl, 6-benzothio[3,2-d]pyrazinyl Examples of the silafluorenyl include 7-benzothio[3,2-d]pyrazinyl, 8-benzothio[3,2-d]pyrazinyl, 9-benzothio[3,2-d]pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, and 4-dibenzoselenophenyl. Furthermore, examples of the "halogen" include F, Cl, Br, and I.
[0021] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes that indicate the relative positions of the substituents, respectively. Ortho indicates that two substituents are adjacent to each other, for example, when two substituents of a benzene derivative occupy the 1st and 2nd positions or the 2nd and 3rd positions, it is called the ortho position. Meta indicates that two substituents are at the 1st and 3rd positions, for example, when two substituents of a benzene derivative occupy the 1st and 3rd positions, it is called the meta position. Para indicates that two substituents are at the 1st and 4th positions, for example, when two substituents of a benzene derivative occupy the 1st and 4th positions, it is called the para position.
[0022] In this specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or another functional group, i.e., a substituent, and also includes the case where a hydrogen atom is replaced with a group formed by the bonding of two or more of the above-mentioned substituents.For example, the "group formed by the bonding of two or more substituents" can be pyridine-triazine.That is, pyridine-triazine can be interpreted as one heteroaryl substituent or as a substituent to which two heteroaryl substituents are bonded.In the present specification, the terms "substituted (C1-C30) alkyl", "substituted (C6-C30) aryl(ene)", "substituted (3- to 7-membered) heteroaryl(ene)", "substituted (C3-C30) cycloalkyl", "substituted (C3-C30) cycloalkenyl", "substituted (3- to 7-membered) heterocycloalkyl", "substituted (C1-C30) alkoxy", "substituted tri(C1-C30) alkylsilyl", "substituted di(C1-C30) alkyl(C6-C30) arylsilyl", "substituted (C1-C30) alkyldi(C6-C30) arylsilyl", "substituted tri(C6-C30) arylsilyl", "substituted mono- or di(C1-C30) alkylsilyl", "substituted di( ... The substituents of the (C30)alkylamino, substituted mono- or di(C6-C30)arylamino, and substituted (C1-C30)alkyl(C6-C30)arylamino 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- to 7-membered)heterocycloalkyl; ( (C6-C30)aryloxy;(C6-C30)arylthio;(5-30 membered)heteroaryl unsubstituted or substituted with (C6-C30)aryl;(C6-C30)aryl unsubstituted or substituted with (5-30 membered)heteroaryl;Tri(C1-C30)alkylsilyl;Tri(C6-C30)arylsilyl;Di(C1-C30)alkyl(C6-C30)arylsilyl;(C1-C30)alkyldi(C6-C30)arylsilyl;Amino;Mono- or di(C1-C30)alkylamino;Unsubstituted or (C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl. At least one selected from the group consisting of mono- or di(C6-C30)arylamino substituted with; (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)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.For example, the substituents may each independently be at least one selected from the group consisting of carbazolyl, phenyl unsubstituted or substituted with naphthyl, biphenyl, naphthyl, dibenzofuranyl, phenanthrenyl, benzocarbazolyl, dimethylfluorenyl, or naphthyl unsubstituted or substituted with phenyl.
[0023] In the formula of the present disclosure, when a ring is formed by the bonding of adjacent substituents, the ring may be a substituted or unsubstituted, monocyclic or polycyclic, (3-30 membered) alicyclic or aromatic ring, or a combination thereof, formed by the bonding of at least two adjacent substituents. In addition, the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. According to one embodiment of the present disclosure, the number of ring skeletal atoms is 5-20, and according to another embodiment of the present disclosure, the number of ring skeletal atoms is 5-15.
[0024] In the formulas of the present disclosure, heteroaryl or heteroarylene may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, and the like. arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
[0025] Several host materials are described in more detail below.
[0026] The multiple host materials according to the present disclosure include a first host material comprising a compound represented by Formula 1 and a second host material comprising a compound represented by Formula 2. The multiple host materials can be included in an emissive layer of an organic electroluminescent device according to one embodiment.
[0027] The first host material according to one embodiment of the present disclosure can be represented by Formula 1 below: [ka]
[0028] In formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L1 may represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5-25 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5-18 membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted carbazolylene, or a substituted or unsubstituted benzocarbazolylene. For example, L1 may represent a single bond, unsubstituted or phenyl- or deuterium-substituted carbazolylene, dibenzofuranylene, naphthylene, unsubstituted or carbazolyl- or deuterium-substituted phenylene, biphenylene, phenanthrenylene, or benzocarbazolylene.
[0029] Ar1 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, -N-(L2-Ar2)(L3-Ar3), a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar1 is hydrogen, deuterium, substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C25) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, -N-(L2-Ar2)(L3-Ar3), substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl, preferably hydrogen, substituted or unsubstituted carbazolyl, substituted or unsubstituted aryl, or substituted or unsubstituted aryl. or unsubstituted phenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenyldibenzofuranylamino, or -N-(L2-Ar2)(L3-Ar3).For example, Ar1 may represent hydrogen; deuterium; carbazolyl unsubstituted or substituted with phenyl, naphthyl, or biphenyl; phenyl unsubstituted or substituted with deuterium, dibenzofuranyl, phenanthrenyl, naphthyl, biphenyl, benzocarbazolyl, or dimethylfluorenyl; terphenyl; biphenyl unsubstituted or substituted with phenyl or deuterium; phenanthrenyl unsubstituted or substituted with phenyl; naphthyl unsubstituted or substituted with phenyl; dibenzofuranyl unsubstituted or substituted with phenyl, biphenyl, or deuterium; dibenzothiophenyl; benzocarbazolyl substituted with phenyl; dimethylfluorenyl; dimethylbenzofluorenyl; spirobifluorenyl; dibenzoselenophenyl; phenylcarbazolylamino; diphenylamino; or -N-(L2-Ar2)(L3-Ar3).
[0030] L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to an embodiment of the present disclosure, L2 and L3 each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (6-25 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (6-18 membered) heteroarylene. For example, L2 and L3 each independently represent a single bond, a phenylene, or a carbazolylene that is unsubstituted or substituted with deuterium.
[0031] Ar2 and Ar3 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar2 and Ar3 each independently represent substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C3-C25) cycloalkyl, substituted or unsubstituted (C3-C25) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (3-25 membered) heteroaryl, preferably substituted or unsubstituted (C3-C18) alkyl, substituted or unsubstituted (C6-C18) cycloalkyl, substituted or unsubstituted (C6-C18) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (3-18 membered) heteroaryl, more preferably substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, dibenzofuranyl, or dibenzothiophenyl. For example, Ar2 and Ar3 can each independently represent unsubstituted or deuterium-substituted phenyl, dibenzofuranyl, or carbazolyl; unsubstituted or deuterium-substituted carbazolyl, phenyl, biphenyl, or naphthyl; unsubstituted or deuterium-substituted dibenzofuranyl; or dibenzothiophenyl. [ka] can be expressed by the following formula 1-1 or formula 1-2. [ka]
[0032] In formulas 1-1 and 1-2, X1 to X 25 are each independently N or CR a R aare each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl. Each of the substituents may be linked to an adjacent substituent to form a ring. For example, R a can represent hydrogen, deuterium, substituted or unsubstituted phenyl, or may be linked with adjacent substituents to form a substituted or unsubstituted aromatic ring.
[0033] According to one embodiment of the present disclosure, X1, X2, X 10 , X 13 , and X 15 ~X 18 are each independently a where R a may be hydrogen or deuterium, or may be linked with adjacent substituents to form a benzene ring.
[0034] * indicates the position where it is linked to L1.
[0035] According to one embodiment of the present disclosure, Formula 1 can be represented by the following Formula 1-1-1. [ka]
[0036] In formula 1-1-1, R 41 ~R 43are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl. Each of the substituents may be linked to an adjacent substituent to form a ring. For example, R 41 ~R 43 can each independently represent hydrogen, deuterium, or a substituted or unsubstituted phenyl, or may be fused with each other to form a substituted or unsubstituted aromatic ring.
[0037] ba can represent an integer of 1 to 3, bb can represent an integer of 1 to 4, and bc can represent an integer of 1 to 5. When ba, bb, and bc each represent an integer of 2 or more, R 41 Each of R 42 and R 43 may be the same or different from each other.
[0038] According to one embodiment of the present disclosure, formula 1-2 can be represented by the following formula 1-2-1. [ka]
[0039] In formula 1-2-1, R 31 ~R 34are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, aryl, 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, or may be linked to adjacent substituents to form a ring. For example, R 31 ~R 34 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl, or may be fused with each other to form a substituted or unsubstituted aromatic ring.
[0040] aa can represent an integer of 1 to 3, ab and ac can each independently represent an integer of 1 to 4, and ad can represent an integer of 1 or 2. When aa, ab, ac, and ad each represent an integer of 2 or more, R 31 Each of R 32 Each of R 33 and R 34 Each may be the same as or different from the others.
[0041] According to one embodiment of the present disclosure, at least one of Ar2 and Ar3 in formula 1 can be represented by any one of the following formulas 1-3-1 to 1-3-4. [ka]
[0042] In formulae 1-3-1 to 1-3-4, T represents O, S, CR5R6, NR7, or Se. R3 to R7 are R a wherein c represents an integer of 1 to 4, d represents an integer of 1 to 3, and when c and d each represent an integer of 2 or greater, each R3 and each R4 may be the same as or different from each other.
[0043] For example, T can represent O, S, CR5R6, NR7, or Se, where R5-R7 can each independently represent methyl, phenyl, biphenyl, or naphthyl.
[0044] As another host material according to an embodiment of the present disclosure, the second host compound is represented by Formula 2: [ka]
[0045] In formula 2, X represents O or S.
[0046] L4 and L5 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene. According to one embodiment of the present disclosure, L4 and L5 each independently represent a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (3-25 membered) heteroarylene, and preferably a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted dibenzofuranylene. For example, L4 and L5 may each independently represent a single bond, unsubstituted or naphthyl-substituted phenylene, biphenylene, terphenylene, phenanthrenylene, unsubstituted or phenyl- or naphthyl-substituted dibenzofuranylene, unsubstituted or phenyl-substituted naphthylene, phenanthro[3,4-d]oxazolyl, phenanthro[4,3-d]oxazolyl, or phenanthro[3,4-d]thiazolyl.
[0047] Ar4 and Ar5 each independently represent a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl. According to one embodiment of the present disclosure, Ar4 and Ar5 each independently represent a substituted or unsubstituted (C6-C25) aryl, preferably a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quaterphenyl, a substituted or unsubstituted benzophenanthrenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted fluoranthenyl, or a substituted or unsubstituted triphenylenyl. For example, Ar4 and Ar5 may each independently represent phenyl substituted with naphthyl, phenanthrenyl, biphenyl, terphenyl, or phenyl-substituted naphthyl; biphenyl substituted with phenyl or biphenyl; terphenyl substituted with phenyl; quaterphenyl; benzophenanthrenyl; dibenzofuranyl substituted with phenyl, biphenyl, phenyl-substituted naphthyl, naphthyl, naphthyl-substituted phenyl, or phenanthrenyl; naphthyl substituted with phenyl, biphenyl, or naphthyl; phenanthrenyl substituted with phenyl, biphenyl, or naphthyl; fluorantrenyl; triphenylenyl; phenanthro[3,4-d]oxazolyl substituted with phenyl; phenanthro[4,3-d]oxazolyl substituted with phenyl; or phenanthro[3,4-d]thiazolyl substituted with phenyl.
[0048] R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or -SiR 11 R 12 R 13According to one embodiment of the present disclosure, R1 and R2 may each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C25) alkyl, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-membered to 25-membered) heteroaryl, preferably hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted phenanthrenyl. For example, R1 and R2 may each independently represent hydrogen, unsubstituted or naphthyl-substituted phenyl, biphenyl, unsubstituted or phenyl-substituted naphthyl, or phenanthrenyl.
[0049] a represents an integer of 1 to 4, and b represents an integer of 1 to 3. When a and b each represent an integer of 2 or more, each R1 and each R2 may be the same as or different from each other.
[0050] According to one embodiment of the present disclosure, formula 2 can be represented by any one of the following formulas 2-1 to 2-4. [ka]
[0051] In formulas 2-1 to 2-4, X, R1, R2, L4, L5, Ar4, Ar5, a, and b have the same definitions as those in formula 2.
[0052] According to one embodiment of the present disclosure, the compound represented by formula 1 may be selected from the group consisting of, but is not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0053] In the above compound, Dn indicates that n hydrogen atoms have been replaced with deuterium atoms.
[0054] According to one embodiment of the present disclosure, the compound represented by formula 2 may be selected from the group consisting of, but is not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0055] A combination of at least one of the compounds H1-1 to H1-151 and at least one of the compounds C-1 to C-397 can be used in an organic electroluminescent device.
[0056] The compound represented by formula 1 according to the present disclosure, specifically, the compound represented by formula 1-1, can be synthesized by referring to the method disclosed in (Patent Document 2) (filed on February 23, 2018), and the compound represented by formula 1-2 can be synthesized by referring to the method disclosed in (Patent Document 3) (published on February 6, 2018), but is not limited thereto, and can also be prepared by other synthesis methods known to those skilled in the art.
[0057] The compound represented by formula 2 can be prepared by synthetic methods known to those skilled in the art, for example, but not limited to, by referring to the following Reaction Scheme 1. [Reaction Scheme 1] [ka]
[0058] In Reaction Scheme 1, X, R1, R2, L4, L5, Ar4, Ar5, a, and b have the same definitions as defined in Formula 2, and Hal represents a halogen.
[0059] Although exemplary synthetic examples of the compounds represented by formulas 1 and 2 are described above, those skilled in the art can easily understand that all of them are based on Buchwald-Hartwig cross-coupling reaction, N-arylation reaction, H-mont mediated etherification reaction, Miyaura boronation reaction, Suzuki cross-coupling reaction, intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, dehydration ring closure reaction, SN1 substitution reaction, SN2 substitution reaction, and phosphine-mediated reductive cyclization reaction, etc., and that the above reactions proceed even when substituents defined in formulas 1 and 2 but not specified in the specific synthetic examples are attached.
[0060] Organic electroluminescent devices using some of the host materials described above are described in more detail below.
[0061] The present disclosure provides an organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, the at least one light-emitting layer comprising a plurality of host materials according to the present disclosure. The first host material and the second host material according to the present disclosure may be included in one light-emitting layer, or may be included in different light-emitting layers among the plurality of light-emitting layers. The plurality of host materials according to the present disclosure may comprise a compound represented by formula 1 and a compound represented by formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30. In addition, the compound represented by formula 1 and the compound represented by formula 2 in the desired ratio may be combined by mixing them in a shaker, by dissolving them by heat in a glass tube, or by dissolving them in a solvent, etc.
[0062] According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound of the light-emitting layer can be less than 20% by weight.The dopant contained in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, and is preferably a phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure can be, but is not limited to, a metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), preferably an ortho-metallized complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metallized iridium complex compound.
[0063] The dopant included in the organic electroluminescent device of the present disclosure can be, but is not limited to, a compound represented by Formula 101 below. [ka]
[0064] In formula 101, L' is one of the following structures 1 to 3: [ka] One of the following is selected from the R 100 ~R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen, (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a ring together with pyridine, such as substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline; R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy, or may be linked with adjacent substituents to form a substituted or unsubstituted ring, for example, substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothienopyridine together with benzene; R 201 ~R 220 each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium and / or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl, or may be bonded to an adjacent substituent to form a substituted or unsubstituted ring, s represents an integer of 1 to 3.
[0065] Specific examples of the dopant compound are as follows, but are not limited to these. [ka] [ka] [ka] [ka] [ka] [ka]
[0066] The organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes an emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of the layers may further be configured as a plurality of layers.
[0067] Each of the anode and cathode may be made of a transparent conductive material, or may be made of a semi-transparent or reflective conductive material. Depending on the type of material that forms the anode and cathode, the organic electroluminescent device may be top-emitting, bottom-emitting, or double-sided emitting. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.
[0068] The organic layer may further include at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds. Furthermore, the organic material layer may further include at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic elements of d-transition elements of the periodic table, or at least one complex compound containing the metal.
[0069] In addition, the organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer that comprises the blue, red or green light-emitting compound known in the art in addition to the compound of the present disclosure.In addition, if necessary, it can also comprise a yellow or orange light-emitting layer.
[0070] 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 referred to as a "surface layer") is preferably disposed on the inner surface of at least one of a pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode surface on the electroluminescent medium layer side, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode surface on the electroluminescent medium layer side. The driving stability of the organic electroluminescent device can be obtained by the surface layer. A preferred example of the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc.; preferred examples of metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc., and preferred examples of metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
[0071] A hole injection layer, a hole transport layer, an electron blocking layer or a combination thereof can be used between the anode and the light emitting layer. The hole injection layer can be a multi-layer 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 kinds of compounds can be used simultaneously in each of the multi-layers. The hole transport layer or the electron blocking layer can be a multi-layer.
[0072] 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 multi-layered for the purpose of controlling electron injection and improving the interface properties between the light emitting layer and the electron injection layer, and two kinds of compounds may be used simultaneously in each of the multi-layered layers. The hole blocking layer or the electron transport layer may be multi-layered, and multiple compounds may be used in each of the multi-layered layers.
[0073] The light-emitting auxiliary layer can be a layer disposed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer, or between the cathode and the light-emitting layer. When disposed between the anode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote hole injection and / or hole transport, or to block electron overflow. When disposed between the cathode and the light-emitting layer, the light-emitting auxiliary layer can be used to promote electron injection and / or electron transport, or to block hole overflow. In addition, the hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can exhibit the effect of promoting or blocking the transport rate of holes (or hole injection rate), thereby adjusting the charge balance. Furthermore, the electron blocking layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can block the overflow of electrons from the light-emitting layer and confine excitons in the light-emitting layer to prevent light leakage. When organic electroluminescent device includes two or more hole transport layers, the additional hole transport layer can be used as hole auxiliary layer or electron blocking layer. The light emitting auxiliary layer, hole auxiliary layer or electron blocking layer can have the effect of improving the efficiency and / or life of organic electroluminescent device.
[0074] In addition, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reductive dopant or the mixed region of the hole transport compound and the oxidative dopant can be disposed on at least one surface of the electrode pair. In this case, the electron transport compound is reduced to anion, so that it is easier to inject and transport electrons from the mixed region to the luminescent medium. Furthermore, the hole transport compound is oxidized to cation, so that it is easier to inject and transport holes from the mixed region to the luminescent medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds, and preferred reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, by using a reductive dopant layer as a charge generating layer, an organic electroluminescent device having at least two luminescent layers and emitting white light can be manufactured.
[0075] The organic electroluminescent material according to an embodiment of the present disclosure can be used as the light-emitting material for white organic light-emitting devices. The white organic light-emitting devices have been proposed to have various structures, such as side-by-side arrangement method, stacked arrangement method, or color conversion material (CCM) method, etc., depending on the arrangement of R (red), G (green) or YG (yellow-green) and B (blue) light-emitting units. In addition, the organic electroluminescent material according to an embodiment of the present disclosure can also be used in organic electroluminescent devices that include quantum dots (QDs).
[0076] To form each layer of the organic electroluminescent device of the present disclosure, dry film forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc. can be used. When forming a film of the first host compound and the second host compound of the present disclosure, co-evaporation or mixed deposition is carried out.
[0077] When using a wet film-forming method, the thin film can be formed by dissolving or dispersing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or dispersed and which has no problem in film-forming ability.
[0078] In addition, the organic electroluminescent devices of the present disclosure can be used to manufacture display systems, such as display systems for smartphones, tablets, notebooks, PCs, TVs, or automobiles; or lighting systems, such as outdoor or indoor lighting systems.
[0079] Hereinafter, the preparation method of the compounds of the present disclosure and their properties, and the driving voltage and luminous efficiency of the organic electroluminescent device (OLED) that comprises multiple host materials according to the present disclosure are described in detail with respect to the representative compounds of the present disclosure.However, the following examples only describe the properties of the compounds of the present disclosure and the OLED that comprises them, and the present disclosure is not limited to the following examples. EXAMPLES
[0080] Example 1: Preparation of Compound H-99 [ka] In a flask, compound 1 (35 g, 120.13 mmol), 2-bromo-9-phenyl-9H-carbazole (58 g, 180.19 mmol), CuI (11 g, 60.06 mmol), ethylenediamine (8 mL, 120.13 mmol), and cesium carbonate (Cs2CO3) (78 g, 240.26 mmol) were dissolved in 600 mL of o-xylene, and the mixture was stirred under reflux for 6 h. The mixture was cooled to room temperature, and H2O was added to the solid reaction product, which was stirred for 30 min, filtered, and separated by column chromatography to obtain compound H-99 (29.5 g, yield: 46.8%).
[0081] [Table 1]
[0082] Example 2: Preparation of Compound H-1 [ka] In a flask, compound 1 (10 g, 34.322 mmol), 3-bromo-9-phenyl-9H-carbazole (16.5 g, 51.484 mmol), CuI (3.2 g, 17.162 mmol), ethylenediamine (2.2 mL, 34.322 mmol), and cesium carbonate (Cs2CO3) (22.4 g, 68.646 mmol) were dissolved in 171 mL of o-xylene, and the mixture was stirred under reflux for 6 h. The mixture was cooled to room temperature, and H2O was added to the solid reaction product, which was stirred for 30 min, filtered, and separated by column chromatography to obtain compound H-1 (11.4 g, yield: 63%).
[0083] [Table 2]
[0084] Example 3: Preparation of Compound H-2 [ka] In a flask, compound 1 (9 g, 30.8 mmol), 4-bromo-9-phenyl-9H-carbazole (15 g, 46.5 mmol), Cu2SO4 (2.5 g, 15.6 mmol), and potassium carbonate (K2CO3) (8.5 g, 61.5 mmol) were dissolved in 200 mL of o-dichlorobenzene, and the mixture was stirred under reflux for 4 h. The mixture was cooled to room temperature, and H2O was added to the solid reaction product, which was stirred for 30 min, filtered, and separated by column chromatography to obtain compound H-2 (4 g, yield: 24%).
[0085] [Table 3]
[0086] Example 4: Preparation of compound H-50 [ka] In a flask, compound 2 (5 g, 15.1 mmol), 3-bromo-9-phenyl-9H-carbazole (5.3 g, 16.6 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3) (0.69 g, 0.75 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (0.72 g, 1.51 mmol), and sodium tert-butoxide (3.6 g, 37.8 mmol) were dissolved in 75 mL of o-xylene, and the mixture was stirred under reflux for 1.5 hours. The mixture was cooled to room temperature, filtered through silica, and separated by column chromatography to obtain compound H-50 (7.3 g, yield: 85%).
[0087] [Table 4]
[0088] Example 5: Preparation of Compound H-100 [ka] In a flask, compound 2 (7 g, 21.187 mmol), 2-bromo-9-phenyl-9H-carbazole (7.5 g, 23.31 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3) (1.0 g, 1.093 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (1.0 g, 2.118 mmol), and sodium tert-butoxide (3.0 g, 31.78 mmol) were dissolved in 105 mL of o-xylene, and the mixture was stirred under reflux for 1.5 hours. The mixture was cooled to room temperature, filtered through silica, and separated by column chromatography to obtain compound H-100 (6.5 g, yield: 54%).
[0089] [Table 5]
[0090] Example 6: Preparation of Compound H-51 [ka] In a flask, compound 2 (10 g, 30.2 mmol), 4-bromo-9-phenyl-9H-carbazole (10.7 g, 32 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3) (1.4 g, 1.5 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (1.45 g, 3 mmol), and sodium tert-butoxide (7.3 g, 75.96 mmol) were dissolved in 150 mL of o-xylene, and the mixture was stirred under reflux for 1 hour. After the reaction was completed, the mixture was extracted with ethyl acetate and separated by column chromatography to obtain compound H-51 (8 g, yield: 46.8%).
[0091] [Table 6]
[0092] Example 7: Preparation of Compound H-111 [ka] In a flask, compound 3 (10 g, 22.4 mmol), N,9-diphenyl-9H-carbazol-1-amine (9 g, 26 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3) (1.0 g, 1.1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (900 mg, 2.2 mmol), and sodium tert-butoxide (3.17 g, 33 mmol) were dissolved in 110 mL of xylene, and the mixture was stirred at 160° C. for 3 hours. The mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound H-111 (7.1 g, yield: 45.3%).
[0093] [Table 7]
[0094] Example 8: Preparation of Compound H-6 [ka] In a flask, compound 1 (5.0 g, 17.213 mmol), compound 8 (6.7 g, 18.93 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3) (0.78 g, 0.86 mmol), sodium tert-butoxide (2.5 g, 25.819 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (0.82 g, 1.721 mmol) were dissolved in 100 mL of o-xylene, and the mixture was stirred under reflux for 1 h. After the reaction was completed, the mixture was cooled to room temperature and filtered through Celite to obtain a solid, which was then separated by column chromatography to obtain compound H-6 (7.8 g, yield: 75%).
[0095] Device Examples 1-5: Fabrication of OLEDs by co-evaporating a first host compound and a second host compound according to the present disclosure An OLED according to the present disclosure was fabricated. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd., Japan) on a glass substrate for the OLED was subjected to ultrasonic cleaning in acetone and isopropyl alcohol, successively, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 shown in Table 2 was placed in one cell of the vacuum deposition apparatus, and compound HT-1 was placed in another cell. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 3 wt % based on the total amount of compound HI-1 and compound HT-1 to form a first hole injection layer having a thickness of 10 nm. Compound HT-1 was then deposited on the first hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, the compound HT-2 was introduced into another cell of the vacuum deposition apparatus and evaporated by passing a current through the cell, thereby depositing a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was deposited thereon as follows. Each of the first host compound and the second host compound shown in Table 1 below was introduced into two cells of the vacuum deposition apparatus as a host, and the compound D-39 was introduced into another cell as a dopant. The two host materials were evaporated in a 1:1 ratio, the dopant materials were simultaneously evaporated in different ratios, and the dopant was deposited in a doping amount of 3 wt % based on the total amount of the host and the dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, the compound ET-1 and the compound EI-1 were evaporated in a weight ratio of 50:50 as electron transport materials to form an electron transport layer having a thickness of 35 nm on the light-emitting layer. Compound EI-1 was evaporated onto the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an Al cathode was evaporated onto the electron injection layer with a thickness of 80 nm by using another vacuum evaporation apparatus, thereby fabricating an OLED. All the materials used to fabricate the OLED were 10 -6 It was purified by vacuum sublimation at torr.
[0096] Comparative Examples 1 to 5: Preparation of OLEDs containing comparative compounds as hosts OLEDs were fabricated similarly to Device Examples 1-5, except that the second host compound shown in Table 1 below was used alone as the host in the emissive layer.
[0097] The driving voltage, luminous efficiency, and luminous color at a luminance of 5,000 nits, as well as the time required for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime: T95) of the OLEDs of device Examples 1 to 5 and Comparative Examples 1 to 5 manufactured as described above are shown in Table 1 below.
[0098] [Table 8]
[0099] From Table 1 above, it can be seen that the OLED using multiple host materials according to the present disclosure not only exhibits driving voltage and luminous efficiency at least equal or similar levels to organic electroluminescent devices containing conventional host combinations, but also exhibits excellent life characteristics.
[0100] The compounds used in the device examples and comparative examples are shown in Table 2 below.
[0101] [Table 9]
[0102] [Table 10]
Claims
1. A plurality of host materials including a first host material including a compound represented by the following formula 1 and a second host material including a compound represented by the following formula 2: 【Chemistry 1】 (In formula 1, L 1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar 1 is hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, -N-(L 2 -Ar 2 ) (L 3 -Ar 3 ), substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl; L 2 and L 3 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar 2 and Ar 3 each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3-7 membered) heterocycloalkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl; 【Chemistry 2】 is represented by the following formula 1-1 or 1-2: 【Chemistry 3】 It is represented by: In formulas 1-1 and 1-2, X 1 ~X 25 are each independently N or CR a represents R a are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl, 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, or may be linked to adjacent substituents to form a ring; * is L 1 (Represents the position where the 【Chemistry 4】 (In formula 2, X represents O or S; L 4 and L 5 each independently represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar 4 and Ar 5 each independently represents a substituted or unsubstituted (C6 to C30) aryl, or a substituted or unsubstituted (3 to 30 membered) heteroaryl; R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-30 membered) heteroaryl, or -SiR 11 R 12 R 13 represents; a represents an integer of 1 to 4, b represents an integer of 1 to 3, and when a and b each represent an integer of 2 or more, R 1 and R 2 may be the same or different from each other).
2. Formula 1-1 is the following formula 1-1-1: 【Chemistry 5】 (In formula 1-1-1, R 41 ~R 43 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) aryl, 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, or may be linked to adjacent substituents to form a ring; ba represents an integer of 1 to 3, bb represents an integer of 1 to 4, and bc represents an integer of 1 to 5. When ba, bb, and bc are integers of 2 or more, R 41 Each of R 42 Each of and R 43 wherein each of said host materials is the same or different.
3. Formula 1-2 is the following formula 1-2-1: 【Chemistry 6】 (In formula 1-2-1, R 31 ~R 34 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, aryl, 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, or may be linked to adjacent substituents to form a ring; aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, ad represents 1 or 2, and when aa, ab, ac, and ad each represent an integer of 2 or more, R 31 Each of R 32 Each of R 33 Each of and R 34 wherein each of said host materials is the same or different.
4. Ar in Formula 1 2 and Ar 3 At least one of the following formulas 1-3-1 to 1-3-4: 【Chemistry 7】 (In formulas 1-3-1 to 1-3-4, T is O, S, CR 5 R 6 , N.R. 7 or Se, R 3 ~R 7 is R of claim 1 a wherein c represents an integer of 1 to 4, d represents an integer of 1 to 3, and when c and d each represent an integer of 2 or more, R 3 and R 4 wherein each of said host materials is the same or different from each other.
5. Formula 2 is the following formulas 2-1 to 2-4: 【Chemistry 8】 (In formulas 2-1 to 2-4, X, R 1 , R 2 , L 4 , L 5 , Ar 4 , Ar 5 13. The host material of claim 1, wherein a is an integer of 1 to 10, and b is an integer of 1 to 10.
6. The compound represented by formula 1 is the following compound: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 2. The host material according to claim 1, wherein Dn is at least one selected from the following: (in the above compound, Dn represents that n hydrogen atoms are replaced with deuterium atoms):
7. The compound represented by formula 2 is the following compound: 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 2. The host material of claim 1, wherein the host material is at least one selected from:
8. 13. An organic electroluminescent device comprising: an anode; a cathode; and at least one light-emitting layer between the anode and the cathode, the at least one light-emitting layer comprising a plurality of host materials according to claim 1.
Citation Information
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Printer feed roller drive control device
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