Multiple host materials and organic electroluminescent devices comprising the same
By using a variety of main materials combined with compounds of Formula 1 and Formula 2 in OLED, the problem of short life of OLED at high brightness is solved, and a more efficient and longer life OLED is achieved, suitable for display and lighting systems.
Patent Information
- Application Number
- CN201980050321.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-07-23
- Filing Date
- 2019-07-26
- Publication Date
- 2025-07-18
- Estimated Expiration
- 2039-07-26
AI Technical Summary
Existing organic electroluminescent devices (OLEDs) have short lifespans at high brightness, and new materials with higher luminescence efficiency and longer lifespan are needed.
Using the combination of compounds represented by Formula 1 and 2 as the host material, a variety of host materials are formed to improve the luminous efficiency and lifetime of OLED by adjusting the balance of HOMO and LUMO energy levels of hole and electronic characteristics.
It achieves higher luminous efficiency and longer life compared to conventional OLEDs, suitable for display systems and lighting systems.
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Figure BDA0002920287770000021 
Figure BDA0002920287770000031 
Figure BDA0002920287770000101
Abstract
Description
Technical Field
[0001] The present disclosure relates to a plurality of host materials comprising a combination of specific compounds, and an organic electroluminescent device comprising the plurality of host materials. Background Art
[0002] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) of a TPD / Alq3 bilayer composed of a light emitting layer and a charge transport layer. Since then, research on OLEDs has been rapidly carried out and it has been commercialized.
[0003] Currently, phosphorescent materials, which provide excellent luminous efficiency in clear panels, are mainly used in organic electroluminescent devices. In many applications such as TVs and lighting devices, the OLED lifetime is insufficient and there is still a need for high-efficiency OLEDs. Typically, the higher the brightness of an OLED, the shorter its lifetime. Therefore, for long-term use and high resolution of displays, new luminescent materials that exhibit high luminous efficiency and long lifetime are needed.
[0004] Korean Patent Application Publication No. 2017-0022865A discloses phenanthrooxazole derivative compounds. However, there is still a need to develop materials for improving the performance of OLEDs. Summary of the Invention
[0005] Technical Problem
[0006] An object of the present disclosure is to provide an improved host material that can provide an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics.
[0007] Solution to the Problem
[0008] The inventors of the present invention have focused on how compounds having a phenanthrooxazole nucleus uniquely have a lower LUMO energy level compared to typical hole-type hosts, and have studied hole-type hosts that can form an appropriate energy gap with these compounds. Thus, it has been found that when a combination of a compound represented by Formula 1 and a compound represented by Formula 2 is used in a light emitting layer, hole and electron characteristics are balanced by appropriate HOMO and LUMO energy levels, and an OLED having higher luminous efficiency and / or longer lifetime characteristics compared to a conventional OLED can be provided. Specifically, the inventors of the present invention have found that the above object can be achieved by a plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by Formula 1 and the second host material comprises a compound represented by Formula 2:
[0009]
[0010] Wherein,
[0011] X1 and Y1 each independently represent -N=, -NR5-, -O- or -S-, provided that any one of X1 and Y1 represents -N=, and the other represents -NR5-, -O- or -S-;
[0012] L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene;
[0013] Ar represents a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) 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- to 30-membered) heteroarylamino;
[0014] R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl;
[0015] R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tris(C6-C30) arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; or adjacent ones of R2 to R5 may be connected to each other to form one or more rings;
[0016] a represents the integer 1; b and c each independently represent an integer of 1 or 2; d represents an integer of 1 to 3; wherein if b to d are each independently an integer of 2 or greater, then each of R2 to R4 may be the same or different; and
[0017]
[0018] Wherein,
[0019] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl;
[0020] L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;
[0021] R 21 and R 22 each independently represents hydrogen, deuterium, halogen, cyano, 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, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 11 R 12 、 or -SiR 13 R 14 R 15 ; or adjacent Rs 21 or adjacent Rs 22 each independently may be connected to each other to form one or more rings, provided that at least one ring is formed;
[0022] R 11 to R 15 each independently represents a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl; and
[0023] e and f each independently represent an integer from 1 to 4; wherein if e and f are each independently an integer of 2 or greater, each R 21 and each R 22 may be the same or different.
[0024] Advantages of the present invention
[0025] By including a specific combination of the compounds of the present disclosure as host materials, an organic electroluminescent device having higher luminous efficiency and / or longer lifetime characteristics compared to conventional organic electroluminescent devices can be provided, and a display system or a lighting system using the organic electroluminescent device is manufactured. Detailed embodiments
[0026] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and does not mean to limit the scope of the present disclosure in any way.
[0027] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be included in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole assisting material, a light emitting assisting 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.
[0028] The term "a plurality of organic electroluminescent materials" in the present disclosure means one or more combinations of organic electroluminescent materials containing at least two compounds, and the materials can be included in any organic layer constituting the organic electroluminescent device. It can mean both the materials before being included in the organic electroluminescent device (e.g., before vapor deposition) and the materials after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of organic electroluminescent materials can be a combination of at least two compounds, and the materials can be included in at least one of the following: a hole injection layer, a hole transport layer, a hole assisting layer, a light emitting assisting 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. By means of the methods used in the art, at least two compounds can be included in the same layer or different layers. For example, they can be co-evaporated or co-deposited, or can be deposited separately.
[0029] The term "a plurality of host materials" in the present disclosure means a host material containing a combination of at least two compounds, and the materials can be included in any light emitting layer constituting the organic electroluminescent device. It can mean both the materials before being included in the organic electroluminescent device (e.g., before vapor deposition) and the materials after being included in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of host materials in the present disclosure can be a combination of two or more host materials, and can optionally further include conventional materials included in the organic electroluminescent materials. Two or more compounds included in the plurality of host materials in the present disclosure can be included in one light emitting layer, or can be separately included in different light emitting layers. For example, two or more host materials can be co-evaporated or co-deposited, or deposited separately.
[0030] In this text, the term “(C1-C30) alkyl” means a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms forming the chain, where the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C3-C30) cycloalkyl” or “(C3-C30) cycloalkylene” means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 carbon atoms in the ring skeleton, where the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7-membered) heteroalkyl” means a cycloalkyl group having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably consisting of the group of O, S, and N. The above heteroalkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term “(C6-C30) aryl” or “(C6-C30) arylene” means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton. The above aryl or arylene group may be partially saturated and may contain a spiro structure. The above aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, yl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, etc. More specifically, the aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, benzanthracenyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacenyl, pyrenyl, 1- yl, 2- yl, 3- yl, 4- yl, 5- yl, 6- yl, benzo[c]phenanthrenyl, benzo[g] Base, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, dibenzo[a,h]fluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl-4-yl, 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-4-yl, 3-fluorenyl, 4-fluorenyl, 8-fluorenyl, 9-fluorenyl, benzo[a]fluorenyl, 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, etc.
[0031] The term “(3- to 30-membered) heteroaryl” or “(3- to 30-membered) heteroarylene” refers to the following aryl or arylene groups which have 3 to 30 ring skeleton atoms, where the number of ring skeleton atoms is preferably 5 to 30 and includes at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above-mentioned (hetero)aryl can be monocyclic or a fused ring condensed with at least one benzene ring; it can be partially saturated; it can be a heteroaryl or heteroarylene formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds; and it can contain a spiro structure. The above-mentioned heteroaryl can include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzonaphthothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. More specifically, the heteroaryl can 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-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl,7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germaf luorenyl, 2-germaf luorenyl, 3-germaf luorenyl, 4-germaf luorenyl, etc. "Halogen" includes F, Cl, Br, and I.
[0032] In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes indicating the relative positions of substituents. Ortho means that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, they are called ortho. Meta means that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, they are called meta. Para means that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, they are called para.
[0033] As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). In the present disclosure, the substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, and substituted alkylarylamino are each independently at least one selected from the group consisting of: 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; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more (3- to 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 mono- or di-(C6-C30)arylamino substituted with one or more (C1-C30)alkyl; (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. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: (C1-C20)alkyl; (C6-C25)aryl; and (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of (C1-C10)alkyl and (C6-C18)aryl. For example, the substituents can each independently be at least one selected from the group consisting of: methyl, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl.
[0034] In the formulas of the present disclosure, a ring formed by the connection of adjacent substituents means that at least two adjacent substituents are connected or fused to form a substituted or unsubstituted monocyclic or polycyclic (3-membered to 30-membered) alicyclic ring or aromatic ring, or a combination thereof; preferably, a substituted or unsubstituted monocyclic or polycyclic (3-membered to 25-membered) alicyclic ring or aromatic ring, or a combination thereof; more preferably, an unsubstituted or one or more alkyl-substituted monocyclic or polycyclic (5-membered to 20-membered) aromatic ring. In addition, the 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. For example, the ring may be a benzene ring, a benzothiophene ring, a benzofuran ring, an indene ring substituted with one or more phenyl groups, or a benzindene ring substituted with at least one of a phenyl group and a biphenyl group.
[0035] As used herein, each of heteroaryl, heteroarylene, and heterocycloalkyl may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
[0036] In Formula 1, X1 and Y1 each independently represent -N=, -NR5-, -O-, or -S-, provided that any one of X1 and Y1 represents -N=, and the other represents -NR5-, -O-, or -S-.
[0037] In Formula 1, L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene. According to one embodiment of the present disclosure, L1 represents a single bond, or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L1 represents a single bond, or a substituted or unsubstituted (C6-C18) arylene. For example, L1 may represent a single bond, phenylene, naphthylene, or biphenylene.
[0038] In Formula 1, Ar represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino group, or a substituted or unsubstituted (C6-C30) aryl(3- to 30-membered) heteroarylamino group. According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5- to 25-membered) heteroaryl group, a substituted or unsubstituted mono- or di-(C6-C25) arylamino group, or a substituted or unsubstituted (C6-C25) aryl(5- to 25-membered) heteroarylamino group. According to another embodiment of the present disclosure, Ar represents a (C6-C30) aryl group that is unsubstituted or substituted with at least one of a (C1-C10) alkyl group and a (C6-C18) aryl group; an unsubstituted (5- to 25-membered) heteroaryl group; a mono- or di-(C6-C25) arylamino group that is unsubstituted or substituted with at least one of a (C1-C10) alkyl group, a (C6-C18) aryl group, and a (C1-C10) alkyl(C6-C18) aryl group; or a (C6-C18) aryl(5- to 20-membered) heteroarylamino group that is unsubstituted or substituted with one or more (C6-C18) aryl groups. Specifically, Ar may represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzo[a]phenanthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzo[a]fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted nitrogen-containing 23-membered heteroaryl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted spiro[cyclopentane-fluorene] group, a substituted or unsubstituted spiro[indane-fluorene] group, a substituted or unsubstituted spiro[fluorene-benzo[a]fluorene] group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted phenylnaphthylamino group, a substituted or unsubstituted phenylterphenylamino group, a substituted or unsubstituted phenylfluorenylamino group, a substituted or unsubstituted naphthylbiphenylamino group, a substituted or unsubstituted naphthylterphenylamino group, a substituted or unsubstituted naphthylphenanthrylamino group, a substituted or unsubstituted dinaphthylamino group, a substituted or unsubstituted dibiphenylamino group, a substituted or unsubstituted biphenylfluorenylamino group, a substituted or unsubstituted difluorenylamino group, a substituted or unsubstituted biphenyldibenzofuranylamino group, a substituted or unsubstituted biphenyldibenzothiophenylamino group, or a substituted or unsubstituted phenylcarbazolylamino group.For example, Ar may represent phenyl, naphthyl, biphenyl, dimethylfluorenyl, diphenylfluorenyl, phenanthryl, fluoranthenyl, dimethylbenzofluorenyl, diphenylbenzofluorenyl, terphenyl, triphenylene, benzophenanthryl, spirobifluorenyl, spiro[cyclopentane-fluorene]yl, spiro[indane-fluorene]yl, a 23-membered nitrogen-containing heteroaryl, diphenylamino, phenylbiphenylamino, phenylnaphthylamino, phenylterphenylamino, naphthylphenylphenylamino, dimethylfluorenylphenylamino, naphthylterphenylamino, dinaphthylamino, naphthylphenanthrylamino, dibiphenylamino, biphenylnaphthylamino, dimethylfluorenylbiphenylamino, diphenylfluorenylbiphenylamino, dimethylfluorenyldimethylfluorenylamino, biphenyldibenzofuranylamino, biphenyldibenzothiophenylamino, or phenylcarbazolylphenylamino.
[0039] In Formula 1, R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl. According to one embodiment of the present disclosure, R1 represents a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl. According to another embodiment of the present disclosure, R1 represents an unsubstituted (C6-C18) aryl, or an unsubstituted (5-membered to 20-membered) heteroaryl. For example, R1 may represent phenyl, biphenyl, pyridyl, quinolinyl, or isoquinolinyl.
[0040] In Formula 1, R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30)alkylsilyl, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tris(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or adjacent ones of R2 to R5 may be connected to each other to form one or more rings. According to one embodiment of the present disclosure, R2 to R4 may represent hydrogen; and R5 may represent a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl.
[0041] In Formula 1, a represents the integer 1; b and c each independently represent an integer of 1 or 2; d represents an integer from 1 to 3; provided that if each of b to d is independently an integer of 2 or greater, each R2 to each R4 may be the same or different. According to one embodiment of the present disclosure, each of a to d independently represents the integer 1.
[0042] According to one embodiment of the present disclosure, the compound represented by Formula 1 may be represented by at least one of the following Formulas 1-1 and 1-2.
[0043]
[0044] In Formulas 1-1 and 1-2, X1, Y1, Ar, L1, R1 to R4, and a to d are as defined in Formula 1.
[0045] In Formula 2, HAr represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl. According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5-membered to 25-membered) heteroaryl. According to another embodiment of the present disclosure, HAr represents an unsubstituted or (C6-C30) aryl-substituted (5-membered to 20-membered) heteroaryl. Specifically, HAr may represent a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted benzoquinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted benzoisoquinolinyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl. For example, HAr may represent a substituted triazinyl, a substituted pyridyl, a substituted pyrimidinyl, a substituted quinazolinyl, or a substituted quinoxalinyl, wherein the substituents of the substituted triazinyl, substituted pyridyl, substituted pyrimidinyl, substituted quinazolinyl, and substituted quinoxalinyl may be at least one of the following: one or more phenyl groups, one or more biphenyl groups, one or more naphthyl groups, one or more naphthylphenyl groups, one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, one or more benzonaphthofuranyl groups, and one or more benzonaphthothiophenyl groups.
[0046] In Formula 2, L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene. According to one embodiment of the present disclosure, L2 represents a single bond, or a substituted or unsubstituted (C6-C25) arylene. According to another embodiment of the present disclosure, L2 represents a single bond, or an unsubstituted or (C1-C10) alkyl-substituted (C6-C18) arylene. For example, L2 may represent a single bond, phenylene, naphthylene, biphenylene, fluoreneylene substituted with one or more methyl groups, or benzofluoreneylene substituted with one or more methyl groups.
[0047] In Formula 2, R 21 and R 22 each independently represent hydrogen, deuterium, halogen, cyano, 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, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR 11 R 12 、or -SiR 13 R 14 R 15 ; or adjacent R 21 or adjacent R 22 each independently may be connected to each other to form one or more rings, provided that at least one ring must be formed. R 11 to R 15 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, R 21 and R 22 each independently represent hydrogen, or a substituted or unsubstituted (C6-C25) aryl; or adjacent R 21 or adjacent R 22 each independently may be connected to each other to form one or more rings. According to another embodiment of the present disclosure, R 21 and R 22 each independently represent hydrogen, or an unsubstituted (C6-C18) aryl; or adjacent R 21 or adjacent R 22 each independently may be connected to each other to form one or more rings. For example, R 21 and R 22 each independently represent hydrogen or phenyl; or adjacent R 21 or adjacent R 22 each independently may be connected to each other to form one or more rings. Two adjacent R21 and two adjacent Rs 22 at least one of which must be connected to each other to form one or more rings. According to one embodiment of the present disclosure, when adjacent Rs 21 or adjacent Rs 22 are connected to each other to form one or more rings, the ring can be at least one of the following: an unsubstituted benzene ring, an indene ring substituted with one or more phenyl groups, a benzofuran ring, a benzothiophene ring, and a benzoindene ring substituted with at least one of a phenyl group and a biphenyl group.
[0048] In Formula 2, e and f each independently represent an integer from 1 to 4; wherein if e and f are each independently an integer of 2 or greater, then each R 21 and each R 22 can be the same or different.
[0049] According to one embodiment of the present disclosure, the compound represented by Formula 2 can be represented by at least one of Formulas 2-1 to 2-7 below.
[0050]
[0051] In Formulas 2-1 to 2-7, HAr and L2 are as defined in Formula 2.
[0052] In Formulas 2-1 to 2-7, V and W each independently represent NR 16 , O or S.
[0053] R 16 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, R 16 represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-membered to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R 16 represents an unsubstituted (C6-C18) aryl group. For example, R 16 can represent a phenyl group or a biphenyl group.
[0054] In Formulas 2-1 to 2-7, R 31 to R 45 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-membered to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, -NR6R7, or -SiR8R9R 10 . According to one embodiment of the present disclosure, R 31 to R45 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C25) aryl group. According to another embodiment of the present disclosure, R 31 to R 45 Each independently represents hydrogen, or an unsubstituted (C6-C18) aryl group. For example, R 31 to R 45 Each independently may represent hydrogen, or phenyl.
[0055] R6 to R 10 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl group.
[0056] In Formulas 2-1 to 2-7, g, k, l, m, o, q, s, t, and u each independently represent an integer from 1 to 4; h, i, j, n, and p each independently represent an integer from 1 to 6; r represents an integer of 1 or 2; wherein if g to u are each independently an integer of 2 or greater, then each R 31 to each R 45 may be the same or different.
[0057] According to one embodiment of the present disclosure, the compound represented by Formula 2 may be represented by at least one of Formulas 2-11 to 2-38 below.
[0058]
[0059]
[0060] In Formulas 2, 2-1 to 2-7, and 2-11 to 2-38, HAr may represent any one selected from the group consisting of the following Structures 4-1 to 4-28.
[0061]
[0062]
[0063] In Formulas 2, 2-1 to 2-7, and 2-11 to 2-38, L2 may represent a single bond, or any one selected from the group consisting of the following Structures 3-1 to 3-40.
[0064]
[0065]
[0066] The compound represented by Formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.
[0067]
[0068]
[0069]
[0070]
[0071]
[0072]
[0073]
[0074]
[0075]
[0076] The compound represented by Formula 2 can be specifically exemplified by any one of the following compounds C2-1 to C2-259, but is not limited thereto. Each of Compounds C2-1 to C2-259 is independently represented by any one of Formulas 2-11 to 2-38, L2 represents a single bond, or any one of Structures 3-1 to 3-40, and HAr represents any one of Structures 4-1 to 4-28.
[0077]
[0078]
[0079]
[0080]
[0081]
[0082] A combination of at least one of Compounds C-1 to C-191 and at least one of Compounds C2-1 to C2-259 can be used in an organic electroluminescent device.
[0083] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to Korean Patent Application Publication No. 10-2017-0022865A (published on March 2, 2017), but is not limited thereto.
[0084] The compound represented by Formula 2 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 2 can be prepared by referring to Korean Patent Application Publication Nos. 10-2010-0007780A (published on January 22, 2010), 10-2010-0105099A (published on September 29, 2010), 10-2010-0108903A (published on October 8, 2010), 10-2015-0032447A (published on March 26, 2015), 10-2015-0077513A (published on July 8, 2015), 10-2016-0099471A (published on August 22, 2016), 10-2016-0136220A (published on November 29, 2016), and 10-2018-0066818A (published on June 19, 2018), and Korean Patent No. 10-1478990B (published on December 29, 2014), but is not limited thereto.
[0085] The organic light-emitting 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 may contain various organic light-emitting materials, including the compound represented by Formula 1 as a first organic light-emitting material and the compound represented by Formula 2 as a second organic light-emitting material. According to an embodiment of the present disclosure, the organic light-emitting device includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, and the light-emitting layer contains one or more compounds represented by Formula 1 and one or more compounds represented by Formula 2.
[0086] The light-emitting layer contains a host and a dopant. The host contains various host materials. The compound represented by Formula 1 may be included as a first host compound of the various host materials, and the compound represented by Formula 2 may be included as a second host compound of the various host materials. The weight ratio of the first host compound to 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 about 60:40, and still more preferably about 50:50.
[0087] The light-emitting layer is a layer from which light is emitted and may be a single layer or a multilayer in which two or more layers are stacked. Among the various host materials according to the present disclosure, the first host material and the second host material may both be included in one layer or may be separately included in different light-emitting layers. According to an embodiment of the present disclosure, the doping concentration of the dopant compound with respect to the host compound in the light-emitting layer is less than about 20 wt%.
[0088] The organic electroluminescent device of the present disclosure may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole assisting layer, a light-emitting assisting layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to an embodiment of the present disclosure, in addition to the various host materials of the present disclosure, the organic electroluminescent device may further include an amine-based compound as at least one of the following: a hole injection material, a hole transport material, a hole assisting material, a light-emitting material, a light-emitting assisting material, and an electron blocking material. Additionally, according to an embodiment of the present disclosure, in addition to the various host materials of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of the following: an electron transport material, an electron injection material, an electron buffer material, and a hole blocking material.
[0089] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot die coating, spin coating, dip coating, and flow coating methods may be used.
[0090] When a solvent is used in the wet film-forming method, a thin film may be formed by dissolving or dispersing the material for forming each layer in any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material for forming each layer can be dissolved or dispersed and which has no problem in film-forming ability.
[0091] Additionally, the first host compound and the second host compound may be formed into a film by the methods listed above, typically by co-evaporation method or mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in corresponding individual crucible sources and current is applied to two chambers simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporation and current is applied to the chamber to evaporate the materials. Additionally, when the first host compound and the second host compound are present in the same layer or different layers in the organic electroluminescent device, the two host compounds may be deposited separately. For example, the first host compound may be deposited, and then the second host compound may be deposited.
[0092] The present disclosure may provide a display system by using various host materials, the various host materials including a compound represented by Formula 1 and a compound represented by Formula 2. That is, a display system or a lighting system may be produced by using the various host materials of the present disclosure. Specifically, it is possible to produce a display system, such as a display system for a smartphone, a tablet computer, a notebook, a PC, a TV, or an automobile, or a lighting system, such as an outdoor or indoor lighting system, by using the various host materials of the present disclosure.
[0093] Hereinafter, the characteristics of the OLED according to the present disclosure will be explained in detail. However, the following examples only illustrate in detail the characteristics of the OLED according to the present disclosure, but the present disclosure is not limited to the following examples.
[0094] Device Examples 1 to 12: Producing OLEDs according to the present disclosure
[0095] The OLED according to the present disclosure is produced as follows: The indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) of the transparent electrode used on the glass substrate for the OLED is subjected to ultrasonic washing successively with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. The ITO substrate is mounted on the substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 is introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus is controlled to 10 -6 Torr. Thereafter, a current is applied to the chamber to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Then, the second hole transport compound shown in Table 1 below is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming 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, a light-emitting layer is formed thereon as follows: The first host compound and the second host compound shown in Table 1 below are introduced into two chambers of the vacuum vapor deposition apparatus as hosts, respectively, and compound RD is introduced into another chamber as a dopant. The two host materials are evaporated at a rate of 1:1, and at the same time, the dopant material is evaporated at a different rate, thereby depositing at 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, compound ET-1 and compound EI-1 are evaporated at a rate of 1:1 in two other chambers to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm is deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, the OLED is produced.
[0096] Comparative Examples 1 and 2: Producing OLEDs not according to the present disclosure
[0097] An OLED is produced in the same manner as in Device Example 4, except that only one host compound shown in Table 1 below is used instead of two hosts.
[0098] The luminous efficiency of the OLEDs produced in the device examples and comparative examples at a brightness of 1,000 nits, and the time (T95) taken to reduce from 100% initial brightness to 95% brightness at a constant current at a brightness of 5,000 nits are shown in Table 1 below.
[0099] [Table 1]
[0100]
[0101] It can be confirmed from the above device examples and comparative examples that, compared with conventional organic electroluminescent devices, an organic electroluminescent device containing a specific combination of the compounds of the present disclosure as host materials has significantly improved luminous efficiency and lifespan.
[0102] The compounds used in the device examples and comparative examples are shown in Table 2 below.
[0103] [Table 2]
[0104]
Claims
1. A plurality of host materials, said plurality of host materials comprising a first host material and a second host material, wherein said first host material comprises a compound represented by Formula 1: Wherein, X1 represents -N=; Y1 represents -O- or -S-; L1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene; Ar represents a substituted or unsubstituted (C6-C30) aryl, 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-membered to 30-membered) heteroarylamino; wherein the substituent of the substituted aryl is at least one selected from the group consisting of: deuterium; (C1-C30) alkyl; and unsubstituted (C6-C30) aryl; R1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-membered to 30-membered) heteroaryl; R2 to R5 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (3-membered to 30-membered) heteroaryl, a substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted (C1-C30) alkoxy, a substituted or unsubstituted tris(C1-C30) alkylsilyl, a substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, a substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, a substituted or unsubstituted tris(C6-C30) arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30) alkylamino, a substituted or unsubstituted mono- or di-(C6-C30) arylamino, or a substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; or adjacent ones of R2 to R5 may be connected to each other to form one or more rings; a represents the integer 1; b and c each independently represent an integer of 1 or 2; d represents an integer from 1 to 3; wherein if b to d are each independently an integer of 2 or greater, then each R2 to each R4 may be the same or different; and said second host material comprises a compound represented by Formula 2: Wherein, HAr represents a substituted or unsubstituted (3-membered to 30-membered) heteroaryl; L2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-membered to 30-membered) heteroarylene; R 21 and R 22 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkenyl group, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, -NR 11 R 12 、 or -SiR 13 R 14 R 15 ; or adjacent R 21 or adjacent R 22 can each independently be connected to each other to form one or more rings, provided that at least one ring is formed; R 11 to R 15 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and e and f each independently represent an integer from 1 to 4; provided that if e and f are each independently an integer of 2 or greater, then each R 21 and each R 22 may be the same or different.
2. The multiple main materials according to claim 1, wherein, The substituents of the substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, and the substituted alkylarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; unsubstituted or (3- to 30-membered)heteroaryl substituted with one or more (C6-C30)aryl; (C6-C30)aryl unsubstituted or substituted with one or more (3- to 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 mono- or di-(C6-C30)arylamino substituted with one or more (C1-C30)alkyl; (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.
3. The multiple main body materials according to claim 1, wherein, The compound represented by Formula 1 is represented by at least one of Formulas 1-1 and 1-2 below: wherein X1, Y1, Ar, L1, R1 to R4, and a to d are as defined in claim 1.
4. The multiple main materials according to claim 1, wherein The compound represented by Formula 2 is represented by at least one of Formulas 2-1 to 2-7 below: wherein HAr and L2 are as defined in claim 1; V and W each independently represent NR 16 , O or S; R 16 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; R 31 to R 45 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR6R7, or -SiR8R9R 10 ; R6 to R 10 each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; and g, k, l, m, o, q, s, t, and u each independently represent an integer from 1 to 4; h, i, j, n, and p each independently represent an integer from 1 to 6; r represents an integer of 1 or 2; provided that if each of g through u is an integer of 2 or greater, then each R 31 through each R 45 may be the same or different.
5. The multiple main body materials according to claim 1, wherein, In Formula 1, Ar represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted benzophenanthryl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted spiro[cyclopentane-fluorene]yl, a substituted or unsubstituted spiro[indane-fluorene]yl, a substituted or unsubstituted spiro[fluorene-benzofluorenyl], a substituted or unsubstituted diphenylamino, a substituted or unsubstituted phenylbiphenylamino, a substituted or unsubstituted phenylnaphthylamino, a substituted or unsubstituted phenylterphenylamino, a substituted or unsubstituted phenylfluorenylamino, a substituted or unsubstituted naphthylbiphenylamino, a substituted or unsubstituted naphthylterphenylamino, a substituted or unsubstituted naphthylphenanthrylamino, a substituted or unsubstituted dinaphthylamino, a substituted or unsubstituted dibiphenylamino, a substituted or unsubstituted biphenylfluorenylamino, a substituted or unsubstituted difluorenylamino, a substituted or unsubstituted biphenyldibenzofuranylamino, a substituted or unsubstituted biphenyldibenzothiophenylamino, or a substituted or unsubstituted phenylcarbazolylamino, wherein the substituents of the substituted phenyl, the substituted naphthyl, the substituted biphenyl, the substituted naphthylphenyl, the substituted phenylnaphthyl, the substituted terphenyl, the substituted phenanthryl, the substituted benzophenanthryl, the substituted fluoranthenyl, the substituted fluorenyl, the substituted benzofluorenyl, the substituted triphenylene, the substituted spirobifluorenyl, the substituted spiro[cyclopentane-fluorene]yl, the substituted spiro[indane-fluorene]yl, the substituted spiro[fluorene-benzofluorenyl] are at least one selected from the group consisting of: deuterium; (C1-C30)alkyl; and unsubstituted (C6-C30)aryl.
6. The multiple main materials according to claim 1, wherein, In Formula 2, HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl.
7. The multiple main materials according to claim 1, wherein, The compound represented by Formula 2 is represented by at least one of the following Formulas 2-11 to 2-38: wherein, each HAr independently represents any one selected from the group consisting of the following Structures 4-1 to 4-28: Each L2 independently represents a single bond, or any one selected from the group consisting of the following Structures 3-1 to 3-40:
8. The multi-main body material according to claim 1, wherein, The compound represented by Formula 1 is at least one selected from the group consisting of the following compounds:
9. The plurality of host materials according to claim 7, wherein, The compound represented by Formula 2 is at least one selected from the following compounds C2-1 to C2-259: Wherein, each of the compounds C2-1 to C2-259 is independently represented by any one of Formulas 2-11 to 2-38, L2 represents a single bond, or any one of Structures 3-1 to 3-40, and HAr represents any one of Structures 4-1 to 4-28.
10. 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 layer of the light-emitting layer contains the plurality of host materials according to Claim 1.
Citation Information
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