CN116891442A - Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same - Google Patents

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Download PDF

Info

Publication number
CN116891442A
CN116891442A CN202310312100.7A CN202310312100A CN116891442A CN 116891442 A CN116891442 A CN 116891442A CN 202310312100 A CN202310312100 A CN 202310312100A CN 116891442 A CN116891442 A CN 116891442A
Authority
CN
China
Prior art keywords
substituted
unsubstituted
group
membered
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202310312100.7A
Other languages
Chinese (zh)
Inventor
朴孝淳
全廷桓
姜熙龙
赵相熙
李东炯
金辰万
吴洪世
姜炫宇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Electronic Materials Korea Ltd
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020230031333A external-priority patent/KR20230143559A/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Publication of CN116891442A publication Critical patent/CN116891442A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same. By including a specific combination of compounds according to the present disclosure as a variety of host materials, or by including a compound according to the present disclosure, an organic electroluminescent device having improved driving voltage, luminous efficiency, and/or lifetime characteristics compared to conventional organic electroluminescent devices may be provided.

Description

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
Technical Field
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.
Background
In 1987, tang et al, eastman Kodak, inc., by using a TPD/Alq composed of a light-emitting layer and a charge-transporting layer 3 The bilayer was first developed for small molecule green organic electroluminescent devices (OLEDs). Thereafter, the development of the OLED is rapidly completed and the OLED has been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. In many applications, such as TV and lighting devices, the lifetime of the OLED is insufficient and still a higher efficiency of the OLED is required. Typically, the higher the luminance of an OLED, the shorter the lifetime an OLED has. Accordingly, for long-term use and high resolution displays, OLEDs having high luminous efficiency and/or long lifetime are required.
Various materials or concepts for organic layers of organic electroluminescent devices have been proposed in order to improve luminous efficiency, driving voltage and/or lifetime, but they are not satisfactory in practical use. Accordingly, there is a continuing need to develop organic electroluminescent materials having more improved properties (e.g., improved driving voltage, luminous efficiency, power efficiency, and/or lifetime characteristics) compared to the combination of the specific compounds previously disclosed.
On the other hand, chinese patent application publication No. 110903258 discloses aromatic amine compounds. However, the foregoing references do not specifically disclose specific combinations of specific compounds and host materials as claimed in the present disclosure. Furthermore, there is a continuing need to develop luminescent materials with more improved performance (e.g., improved driving voltage, luminous efficiency, and/or lifetime characteristics) compared to the combination of the specific compounds previously disclosed.
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide host materials capable of producing an organic electroluminescent device having improved driving voltage, luminous efficiency and/or lifetime characteristics. It is another object of the present disclosure to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. It is still another object of the present disclosure to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and/or lifetime characteristics by including the compound according to the present disclosure or a specific combination of compounds according to the present disclosure.
Solution to the problem
As a result of intensive studies to solve the above technical problems, the present inventors 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 the following formula 1, and the second host material comprises a compound represented by the following formula 2. Furthermore, the present inventors have found that the above object can be achieved by a compound represented by the following formula 11.
In the formula (1) of the present invention,
X 1 and X 2 Is represented by-n=, and the other is represented by-O-or-S-;
r 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;
ring A represents a (C6-C12) aromatic hydrocarbon;
L 1 and L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
in the formula (2) of the present invention,
T 5 and T 6 、T 7 And T 8 Or all of them are linked to each other to form a ring having the following formula 3:
In the formulae 2 and 3,
t without formation of one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 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, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-di- (C2-C30) alkenyl, substituted or unsubstituted (C1-C30) alkylamino, substituted or unsubstituted tri (C6-C30) alkenylAmino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted mono-or di- (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino, or-L 3 -Ar 5 Provided that T 1 To T 14 At least one of them represents-L 3 -Ar 5 ；
L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 5 each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
-represents a fused site with formula 2; and is also provided with
The heteroaryl and the heteroarylene contain one or more heteroatoms selected from B, N, O, S, si and P.
In the case of the method of claim 11,
X 1 and X 2 Is represented by-n=, and the other is represented by-O-or-S-;
r 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;
ring A represents a (C6-C12) aromatic hydrocarbon; and is also provided with
Ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
with the proviso that when ring A is benzene, -N (Ar) 1 )(Ar 2 ) and-N (Ar) 3 )(Ar 4 ) In ortho-position with respect to each otherOr meta.
The beneficial effects of the invention are that
By including a specific combination of compounds according to the present disclosure as a variety of host materials, or by including a compound according to the present disclosure, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or excellent lifetime characteristics as compared to conventional organic electroluminescent devices is provided. Further, a display device or a lighting device may be manufactured using the organic electroluminescent device of the present disclosure.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including host materials and dopant materials), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The term "multiple host materials" in the present disclosure means a host material comprising a combination of two or more compounds, which may be contained in any light emitting layer constituting an organic electroluminescent device. It may mean both a material before (i.e., before vapor deposition) being included in the organic electroluminescent device and a material after (i.e., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of host materials of the present disclosure may be a combination of at least two host materials, which may optionally further comprise conventional materials included in organic electroluminescent materials. At least two compounds contained in a plurality of host materials may be contained together in one light-emitting layer, or may be contained in different light-emitting layers each. For example, at least two host materials may be co-evaporated or co-evaporated, or may be separately evaporated.
In this context, the term "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, and preferably from 3 to 20 ring backbone carbon atoms, more preferably from 3 to 7 ring backbone carbon atoms. Examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3-to 7-membered) heterocycloalkyl" in the present disclosure means cycloalkyl having 3 to 7 ring backbone atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably O, S and N. The above heterocycloalkyl group includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiophane), tetrahydropyran and the like. The term "(C6-C30) aryl", "(C6-C30) arylene" or "(C6-C30) arene" in the present disclosure means a monocyclic or fused ring group derived from an aromatic hydrocarbon having from 6 to 30 ring backbone carbon atoms. The aryl groups described above may be partially saturated and may contain spiro structures. The aryl group may include phenyl, biphenyl, terphenyl, pentabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, benzophenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, Group, naphto-naphthyl group, fluoranthenyl group, spirobifluorenyl group, spiro [ fluorene-benzofluorene ]]Base, spiro [ cyclopentene-fluorene ]]Base, spiro [ indan-fluorene ]]Radical, azulene radicalTetramethyl dihydrophenanthryl, and the like. More specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthracenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthaceneyl, pyrenyl, 1->Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [ a ]]Fluorenyl and benzo [ b ]]Fluorenyl and 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-tetrabiphenyl, 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-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, 9-dimethyl-1-fluorenyl, 9 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl 9, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 11-dimethyl-1-benzo [ a ]]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ]]Fluorenyl, 11-dimethyl-4-benzo [ c ] ]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ]]Fluorenyl group11, 11-diphenyl-3-benzo [ c ] ]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like.
The term "(3-to 30-membered) heteroaryl" or "(3-to 30-membered) heteroarylene" in the present disclosure means an aryl or arylene group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si and P. It may be a single ring, or a fused ring condensed with at least one benzene ring, and may be partially saturated. In addition, the above heteroaryl or heteroarylene group includes a heteroaryl or heteroarylene group formed by connecting at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and may include a spiro structure. The above heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like, and fused ring heteroaryl groups, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthafuranyl, naphthabenzofuranyl, naphthacene thienyl, naphthazolyl, benzofuranquinolinyl, benzobenzoquinazolinyl, benzofurannaphthyridinyl, benzofuranpyrimidinyl, benzothiophenoquinolinyl, benzothiophenoquinazolinyl, naphthyridinyl, benzothiophenopyridinyl, benzothiophenopyrimidinyl, naphthaceneopyrimidinyl, pyrimidoindolyl, benzopyrimidinyl, benzofuranpyrazinyl, naphthafuranpyrazinyl, benzothiophenopyrazinyl, naphthacene naphthazinyl, naphthaceneopyrazinyl, naphthazinyl, benzofuranpyrimidinyl, benzofuranyl, and naphthazinyl pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolophenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzo pyridinyl, indolocarbazolyl, quinazolinyl, benzoquinoxalinyl, benzocarbazolyl, benzodiazinyl, and the like, indenocarbazolyl and the like. More specifically, the process is carried out, heteroaryl groups may 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-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 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-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-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-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-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, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 2-dibenzo- [1,2-b ] -2- [ 2-b ] -2, 2- [ 2-b ] -2-naphtho-b ] -1, 2-naphtho- [ b ] -2-naphthyridinyl 5-naphtho- [1,2-b ] -benzofuranyl, 6-naphtho- [1,2-b ] -benzofuranyl, 7-naphtho- [1,2-b ] -benzofuranyl, 8-naphtho- [1,2-b ] -benzofuranyl, 9-naphtho- [1,2-b ] -benzofuranyl, 10-naphtho- [1,2-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-naphtho- [2,3-b ] -benzofuranyl, 3-naphtho- [2,3-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 6-naphtho- [2,3-b ] -benzofuranyl, 7-naphtho- [2,3-b ] -benzofuranyl, 8-naphtho- [2,3-b ] -benzofuranyl, 9-naphtho- [2,3-b ] -benzofuranyl, 10-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2,3-b ] -benzofuranyl, 2-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 5-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2, 2-b ] -benzofuranyl, 5-naphtho-b ] -benzofuranyl, 6-naphtho- [2,1-b ] -benzofuranyl, 7-naphtho- [2,1-b ] -benzofuranyl, 8-naphtho- [2,1-b ] -benzofuranyl, 9-naphtho- [2,1-b ] -benzofuranyl, 10-naphtho- [2,1-b ] -benzofuranyl, 1-naphtho- [1,2-b ] -benzothienyl, 2-naphtho- [1,2-b ] -benzothienyl, 3-naphtho- [1,2-b ] -benzothienyl, 4-naphtho- [1,2-b ] -benzothienyl, 5-naphtho- [1,2-b ] -benzothienyl, 6-naphtho- [1,2-b ] -benzothienyl 7-naphtho- [1,2-b ] -benzothienyl, 8-naphtho- [1,2-b ] -benzothienyl, 9-naphtho- [1,2-b ] -benzothienyl, 10-naphtho- [1,2-b ] -benzothienyl, 1-naphtho- [2,3-b ] -benzothienyl, 2-naphtho- [2,3-b ] -benzothienyl, 3-naphtho- [2,3-b ] -benzothienyl, 4-naphtho- [2,3-b ] -benzothienyl, 5-naphtho- [2,3-b ] -benzothienyl, 1-naphtho- [2,1-b ] -benzothienyl, 2-naphtho- [2,1-b ] -benzothienyl, 3-naphtho- [2,1-b ] -benzothienyl, 4-naphtho- [2,1-b ] -benzothienyl, 5-naphtho- [2,1-b ] -benzothienyl, 6-naphtho- [2,1-b ] -benzothienyl, 7-naphtho- [2,1-b ] -benzothienyl, 8-naphtho- [2,1-b ] -benzothienyl, 9-naphtho- [2,1-b ] -benzothienyl, 10-naphtho- [2,1-b ] -benzothienyl, 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-benzo [3, 1-b ] -benzothienyl, 6-benzo [2, 1-d ] pyrimidinyl, 6-benzo [3, 1-b ] -benzothienyl, 2-benzofuro [3,2-d ] pyrimidinyl, 6-benzofuro [3,2-d ] pyrazinyl, 7-benzofuro [3,2-d ] pyrazinyl, 8-benzofuro [3,2-d ] pyrazinyl, 9-benzofuro [ 2-d ] 2-d-naphtyl, 6-benzofurano [2, 2-d ] pyrazinyl, 6-b-benzofurano [ 2-d-b ] pyrazinyl, 2-benzothio [3,2-d ] pyrazinyl, 6-benzothio [3,2-d ] pyrazinyl, 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-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. In the present disclosure, "halogen" includes F, cl, br and I.
In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2 or positions 2 and 3. Meta-position means that two substituents are at positions 1 and 3 and is referred to as meta-position, for example, when two substituents in the benzene derivative occupy positions 1 and 3. Para represents two substituents at positions 1 and 4, and is referred to as para, for example, when two substituents in the benzene derivative occupy positions 1 and 4.
Further, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced with a group formed by the connection of two or more substituents among the above-mentioned substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazines may be interpreted as heteroaryl substituents, or substituents in which two heteroaryl groups are linked. Herein, one or more substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring groups of one or more aliphatic and one or more aromatic rings, substituted mono-or di-alkylamino, substituted mono-or di-alkenylamino, substituted alkylalkenylamino, substituted mono-or di-arylamino, substituted alkylarylamino, substituted mono-or di-heteroarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (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 substituted (C1-C30) At least one substituted (3-to 30-membered) heteroaryl group of an alkyl group and a (C6-C30) aryl group; (C6-C30) aryl, unsubstituted or substituted with at least one of: deuterium, cyano, halogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl and (3-to 30-membered) heteroaryl; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; (C1-C30) alkyl (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: halogen; cyano group; (C1-C20) alkyl; (C3-C25) cycloalkyl; (5-to 25-membered) heteroaryl, unsubstituted or substituted by one or more (C6-C25) aryl groups; (C6-C25) aryl, unsubstituted or substituted with at least one of: halo, cyano, (C1-C20) alkyl, (C3-C25) cycloalkyl, tri (C1-C20) alkylsilyl, tri (C6-C25) arylsilyl, (C6-C25) aryl and (5-to 25-membered) heteroaryl; tri (C1-C20) alkylsilyl; and tri (C6-C25) arylsilyl groups. According to another embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: cyano group; (C1-C10) alkyl; (C3-C18) cycloalkyl; (5-to 20-membered) heteroaryl, unsubstituted or substituted by one or more (C6-C18) aryl groups; is not taken out (C6-C25) aryl substituted by at least one of the following: cyano, halogen, (C1-C10) alkyl, (C3-C18) cycloalkyl, tri (C1-C10) alkylsilyl, tri (C6-C18) arylsilyl, (C6-C18) aryl and (5-to 20-membered) heteroaryl; tri (C1-C10) alkylsilyl; and tri (C6-C18) arylsilyl groups. For example, the one or more substituents may each independently be at least one selected from the group consisting of: fluorine; a methyl group; a substituted or unsubstituted phenyl group; a naphthyl group; a biphenyl group; phenanthryl; a dimethylfluorenyl group; diphenyl fluorenyl; an anthracene group; a naphthylphenyl group; phenyl naphthyl; a terphenyl group;a base; triphenylene; spirobifluorenyl; (C22) aryl; pyridyl substituted with one or more phenyl groups; benzofuranyl; benzothienyl; dibenzofuranyl unsubstituted or substituted with one or more phenyl groups or one or more biphenyl groups; dibenzothienyl; carbazolyl that is unsubstituted or substituted with one or more phenyl groups; naphthooxazolyl, unsubstituted or substituted with one or more phenyl groups; phenoxazinyl and the like; wherein the one or more substituents of the one or more substituted phenyl groups may be selected from at least one of the group consisting of: cyano, fluoro, t-butyl, cyclohexyl, carbazolyl, trimethylsilyl and triphenylsilyl.
In the present disclosure, the heteroaryl, heteroarylene, and heterocycloalkyl groups each independently may include at least one heteroatom selected from the group consisting of B, N, O, S, si and P. Further, 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 (3-to 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, 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- (C2-C30) alkenylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, substituted or unsubstituted mono-to 30-membered hetero (C1-to 30) alkylamino, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C2-C30) alkylamino, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or di (C1-to 30-membered alkylamino, substituted or unsubstituted (C30-to 30-C amino Substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino.
The plurality of host materials according to the present disclosure include a first host material and a second host material, wherein the first host material includes at least one compound represented by formula 1, and the second host material includes at least one compound represented by formula 2. According to one embodiment of the present disclosure, the compound represented by formula 1 and the compound represented by formula 2 are different from each other.
The present disclosure provides compounds represented by formula 1, 2, or 11. The present disclosure may provide an organic electroluminescent material or an organic electroluminescent device including an organic electroluminescent compound, and the organic electroluminescent compound may be included as a host material in a light emitting layer.
In formulas 1 and 11, X 1 And X 2 Each independently is-n=, -O-, or-S-. According to one embodiment of the present disclosure, X 1 And X 2 One of which represents-n=, and the other represents-O-or-S-. According to another embodiment of the present disclosure, X 1 And X 2 One of which represents-n=, and the other represents-O-.
In formulae 1 and 11, R 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. According to one embodiment of the present disclosure, R represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, R represents an unsubstituted (C6-C18) aryl group, or an unsubstituted (5-to 20-membered) heteroaryl group. For example, R may be phenyl, naphthyl, dibenzofuranyl, or the like.
In formulae 1 and 11, ring A represents a (C6-C12) aromatic hydrocarbon. For example, ring a may be benzene or naphthalene.
In formulae 1 and 11, L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L 1 And L 2 Each independently represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. According to another embodiment of the present disclosure, L 1 And L 2 Each independently represents a single bond, or an unsubstituted (C6-C18) arylene group. For example, L 1 And L 2 Each independently may be a single bond, phenylene, or the like.
In formulas 1 and 11, ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, ar 1 To Ar 4 Each independently represents a (C6-C18) aryl group unsubstituted or substituted by one or more (C1-C30) alkyl groups, or a (5-to 20-membered) heteroaryl group unsubstituted or substituted by one or more (C6-C18) aryl groups. For example, ar 1 To Ar 4 Each independently may be phenyl, naphthyl, biphenyl, dimethylfluorenyl, phenanthryl, terphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl substituted with one or more phenyl groups, and the like.
According to one embodiment of the present disclosure, in formula 1, R and Ar 1 To Ar 4 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, or a substituted or unsubstituted spirobifluorenyl groupSubstituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothienyl.
According to one embodiment of the present disclosure, in formula 11, R represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
According to one embodiment of the present disclosure, when ring A in formula 1 is benzene, -L 1 -N(Ar 1 )(Ar 2 ) and-L 2 -N(Ar 3 )(Ar 4 ) At ortho or meta positions relative to each other. When ring A in formula 11 is benzene, -N (Ar) 1 )(Ar 2 ) and-N (Ar) 3 )(Ar 4 ) At ortho or meta positions relative to each other.
According to one embodiment of the present disclosure, formula 1 may be represented by at least one of the following formulas 4 to 6.
R, X in formulae 4 to 6 1 、X 2 、L 1 、L 2 And Ar 1 To Ar 4 Is as defined in formula 1.
In formula 2, T 5 And T 6 、T 7 And T 8 Or all of them are connected to each other to form a toolThere is a ring of formula 3. According to one embodiment of the present disclosure, T 5 And T 6 Are linked to each other to form a ring of formula 3, or T 7 And T 8 Are connected to each other to form a ring having formula 3.
In formulae 2 and 3, T which does not form one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 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, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C3-C30) aliphatic ring, substituted or unsubstituted mono-or unsubstituted (C1-C30) alkylamino, substituted or di- (C1-C30) alkylamino, mono-or di- (C30) alkylamino, substituted or di- (C1-C30) alkylamino, di- (C2-or C30) alkylamino, or di (C30-C30) amino Substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino, or-L 3 -Ar 5 . According to one embodiment of the present disclosure, T does not form one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, substituted or unsubstituted (C6-C25) aryl, or-L 3 -Ar 5 . According to another embodiment of the present disclosure, T does not form one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, unsubstituted (C6-C18) aryl, or-L 3 -Ar 5 . For example T without forming one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, phenyl, naphthyl, biphenyl, or-L 3 -Ar 5 。T 1 To T 14 At least one of them represents-L 3 -Ar 5 . According to one embodiment of the present disclosure, T 1 To T 14 At least one of them is-L 3 -Ar 5 。
L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L 3 Each independently represents a single bond, or a substituted or unsubstituted (C6-C25) arylene group. According to another embodiment of the present disclosure, L 3 Each independently represents a single bond, or a (C6-C18) arylene group which is unsubstituted or substituted by one or more (C6-C18) aryl groups. For example, L 3 May each independently be a single bond, phenylene, naphthylene, biphenylene, or the like, unsubstituted or substituted with one or more phenyl groups.
Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, ar 5 Each independently represents a substituted or unsubstituted (5-to 25-membered) heteroaryl group, and one or more substituents of the substituted heteroaryl group may be at least one selected from the group consisting of: cyano, halogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (3-to 30-membered) heteroaryl, tri (C1-C30) alkylsilyl and tri (C6-C30) arylsilyl. Specifically, ar 5 Can be substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzothienoquinolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinazolineA group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted benzofuranopyrimidinyl group, a substituted or unsubstituted acenaphthylene pyrimidinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzonaphthaphthyl furyl group, a substituted or unsubstituted benzonaphthaphthioyl group, a substituted or unsubstituted benzimidazolyl group, or a substituted or unsubstituted phenanthroimidazolyl group. For example, ar 5 May be a substituted triazinyl group, a substituted pyrimidinyl group, a quinolinyl group substituted with one or more phenyl groups, an isoquinolinyl group substituted with one or more phenyl groups, an unsubstituted benzothiophenoquinolinyl group, a naphthyridinyl group substituted with one or more phenyl groups, a quinazolinyl group substituted with at least one of phenyl and biphenyl groups, a quinoxalinyl group substituted with at least one of phenyl and biphenyl groups, a benzoquinoxalinyl group substituted with one or more biphenyl groups, a dibenzoquinoxalinyl group substituted with one or more biphenyl groups, a benzofuropyrimidinyl group substituted with one or more biphenyl groups, an acenaphthopyrimidinyl group substituted with one or more phenyl groups, a benzimidazolyl group substituted with one or more phenyl groups, a phenanthroimidazolyl group substituted with one or more phenyl groups, a nitrogen-containing 17 membered heteroaryl group substituted with one or more methyl groups, a 25 membered heteroaryl group containing N and O, or the like. The one or more substituents of the substituted triazinyl group may be at least two selected from the group consisting of: phenyl unsubstituted or substituted with one or more cyano groups, one or more fluoro groups, one or more tert-butyl groups, one or more cyclohexyl groups, one or more carbazolyl groups, one or more trimethylsilyl groups, or one or more triphenylsilyl groups; a naphthyl group; a biphenyl group; phenanthryl; a dimethylfluorenyl group; diphenyl fluorenyl; an anthracene group; a naphthylphenyl group; phenyl naphthyl; a terphenyl group; A base; triphenylene; spirobifluorenyl;(C-22) aryl; benzothienyl; dibenzofuranyl unsubstituted or substituted with one or more phenyl groups or one or more biphenyl groups; dibenzothienyl; carbazolyl that is unsubstituted or substituted with one or more phenyl groups; naphthooxazolyl substituted with one or more phenyl groups; a phenoxazinyl group. The one or more substituents of the substituted pyrimidinyl group may be at least one selected from the group consisting of: fluorine, phenyl, biphenyl, pyridyl substituted with one or more phenyl groups, and dibenzofuranyl.
In formula 3- - -represents a condensed site with formula 2.
Heteroaryl and heteroarylene contain one or more heteroatoms selected from B, N, O, S, si and P.
According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas 2-1 and 2-2.
In the formulae 2-1 and 2-2, T 1 To T 4 And T 9 To T 14 Is as defined in formula 2, and T 5 To T 8 Is as in formula 2 for T which does not form one or more rings 5 To T 8 As defined.
According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas.
In the above-mentioned formula (i), the water,
T 1 to T 14 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 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 A substituted or unsubstituted (C6-C30) arylsilyl group, a substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl group, a substituted or unsubstituted tri (C6-C30) arylsilyl group, a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted mono-or di- (C1-C30) alkylamino group, a substituted or unsubstituted mono-or di- (C2-C30) alkenylamino group, a substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino group, a substituted or unsubstituted mono-or di- (C6-C30) arylamino group, a substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino group, a substituted or unsubstituted mono-or di- (3-to 30) heteroarylamino group, a substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered heteroaryl (C2-or 30) arylamino group, a substituted or unsubstituted (C6-C30) heteroaryl group
L 3 And Ar is a group 5 Is as defined in formula 2.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
The compound represented by formula 11 may be at least one selected from the group consisting of compounds C-1 to C-120 and C-126 to C-435, but is not limited thereto.
The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
At least one of the compounds C-1 to C-120 and C-126 to C-435 may be used in an organic electroluminescent device. Furthermore, a combination of at least one of the compounds C-1 to C-437 and at least one of the compounds H2-1 to H2-281 may be used in the organic electroluminescent device.
The organic electroluminescent compound represented by formula 11 according to the present disclosure may be contained in at least one layer selected from the group consisting of: a light emitting layer, a hole injecting layer, a hole transporting layer, a hole assisting layer, a light emitting assisting layer, an electron transporting layer, an electron buffer layer, an electron injecting layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, and in some cases, may be preferably contained in at least one layer selected from the group consisting of: a light emitting layer, a hole transporting layer, a hole assisting layer, a light emitting assisting layer, an electron transporting layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. When used in the light emitting layer, the organic electroluminescent compound represented by formula 11 may be contained as a host material, and may be contained as an electron transporting layer material and/or an electron buffer layer material. If desired, the organic electroluminescent compounds of the disclosure can be used as co-host materials.
The compounds represented by formulas 1 and 11 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, by referring to the following schemes 1-1 and 1-2 and Yeon-Ho Cho et al, tetrahedron [ Tetrahedron journal ], volume 69, stage 32, 2013, pages 6565-6573, etc., but are not limited thereto. The compound represented by formula 2 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art, for example, by referring to the following reaction schemes 2-1 and 2-2, but is not limited thereto.
[ reaction scheme 1-1]
[ reaction schemes 1-2]
In schemes 1-1 and 1-2, X represents halogen, and R, L 1 、L 2 Ar, ar 1 To Ar 4 Is as defined in formulas 1 and 11.
[ reaction scheme 2-1]
[ reaction scheme 2-2]
In schemes 2-1 and 2-2, T and T' are each independently as in formula 2 for T 1 To T 4 Defined, x represents an integer from 1 to 8, and z represents 1An integer of to 4, wherein if x and z are 2 or more, each of T and each of T' may be the same as or different from each other.
Although illustrative synthetic examples of the compounds represented by formulas 1, 2 and 11 are described above, those skilled in the art will readily understand that they are all based on a buhwald-hartmash (Buchwald-Hartwig) cross-coupling reaction, an N-arylation reaction, an acidified montmorillonite (H-mont) mediated etherification reaction, a Miyaura) boronation reaction, a Suzuki (Suzuki) cross-coupling reaction, an intramolecular acid-induced cyclization reaction, a Pd (II) catalyzed oxidative cyclization reaction, a grignard reaction (Grignard Reaction), a Heck reaction (Heck reaction), a dehydrocyclization reaction, a SN1 substitution reaction, a SN2 substitution reaction, a phosphine-mediated reductive cyclization reaction, a Wittig (Wittig) reaction, and the like, and that the above reactions proceed even when substituents defined in formulas 1, 2 and 11 other than the substituents specified in the specific synthetic examples are bonded.
The present disclosure provides an organic electroluminescent device including an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer may comprise 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 contained together in one light emitting layer, or may be contained in different light emitting layers among a plurality of light emitting layers, respectively. The various host materials of the present disclosure may comprise the compound represented by formula 1 and the 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. Further, the compound represented by formula 1 and the compound represented by formula 2 in a desired ratio may be combined by mixing them in a shaker, by dissolving them in a glass tube via heating, or by dissolving them in a solvent or the like.
According to one embodiment of the present disclosure, the dopant compound may have a doping concentration of less than 20wt% relative to the host compound in the light emitting layer. The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but may be a complex compound of metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably orthometalated complex compounds of metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metalated iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following formula 101, but is not limited thereto.
In the case of the method 101,
l is selected from the following structures 1 to 3:
R 100 to R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or one or more halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to one or more adjacent substituents to form together with pyridine one or more rings, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenoquinoline;
R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to one or more adjacent substituents to form together with benzene one or more substituted or unsubstituted rings, for example, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothiophenopyridine;
R 201 to R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted with deuterium and/or one or more halogens, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to one or more adjacent substituents to form one or more substituted or unsubstituted rings; and is also provided with
s is an integer from 1 to 3.
Specific examples of the dopant compounds are as follows, but are not limited thereto.
/>
/>
/>
/>
/>
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 comprises a light emitting layer, and may further comprise at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist 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 these layers may be further configured as multiple layers.
The anode and cathode may be formed of a transparent conductive material, or a transflective or reflective conductive material. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a two-side emission type according to the types of materials forming the anode and the cathode. 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.
The organic layer may further include at least one selected from the group consisting of: aryl amine-based compounds and styrylamine-based compounds. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: a metal of group 1 of the periodic table, a metal of group 2, a transition metal of group 4, a transition metal of group 5, an organometallic of a lanthanide and a d-transition element, or at least one complex compound comprising the metal.
In addition, the organic electroluminescent device according to the present disclosure may emit white light by further including at least one light emitting layer including a blue, red or green electroluminescent compound known in the art in addition to the compound of the present disclosure. It may further comprise a yellow or orange light emitting layer, if desired.
In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a halogenated metal layer, and a metal oxide layer may be preferably placed on one or both electrodesIs provided on the inner surface or surfaces of the housing. In particular, it is preferable to place a layer of chalcogenides (including oxides) of silicon and aluminum on the anode surface of the electroluminescent medium layer, and to place a layer of a metal halide or metal oxide on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like; the halogenated metal comprises LiF, mgF 2 、CaF 2 Rare earth metal fluorides, etc.; and the metal oxide includes Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. The hole transport layer or the electron blocking layer may be a multilayer.
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 a plurality of layers in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the plurality of layers may use two compounds at the same time. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein each layer may use a plurality of compounds.
The light emitting auxiliary layer may be placed between the anode and the light emitting layer, or between the cathode and the light emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to promote hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to promote electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and the hole transport rate (or hole injection rate) may be effectively promoted or limited, thereby enabling control of charge balance. Further, an electron blocking layer may be disposed between the hole transporting layer (or hole injecting layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving efficiency and/or lifetime of the organic electroluminescent device.
Further, in the organic electroluminescent device of the present disclosure, it is preferable that a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant is placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus injection and transport of electrons from the mixing region to the electroluminescent medium becomes easier. Furthermore, the hole transporting compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the electroluminescent medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds, and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer may be used as a charge generation layer to produce an organic electroluminescent device having two or more light emitting layers and emitting white light.
According to one embodiment, an organic electroluminescent material may be used as a light emitting material for a white organic light emitting device. A white organic light emitting device has been proposed to have various structures such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light emitting members, or a Color Conversion Material (CCM) method, or the like. Furthermore, according to one embodiment, the organic electroluminescent material may also be applied in an organic electroluminescent device including Quantum Dots (QDs).
In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, or the like may be used. When the first host compound and the second host compound of the present disclosure are used to form a film, a co-evaporation method or a mixed evaporation method is performed. Co-deposition or hybrid deposition is performed when forming films of the first and second host materials of the present disclosure.
When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in terms of film forming ability.
Further, a display system, for example, a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, can be manufactured by using the organic electroluminescence device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, a method of preparing the compound according to the present disclosure and physical characteristics thereof, and a driving voltage and light emitting efficiency of an organic electroluminescent device (OLED) including various host materials of the present disclosure will be explained with reference to representative compounds of the present disclosure. However, the following examples only describe the features of OLED devices comprising compounds according to the present disclosure, but the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-235
1) Synthesis of Compound A-1
In a flask, compound A (9 g,50.6 mmol), benzaldehyde (6.44 g,60.7 mmol) and NaCN (2.48 g,50.6 mmol) were dissolved in 180mL DMF and then stirred at 140℃under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and separated with a silica filter to obtain compound A-1 (6.0 g, yield: 45%).
2) Synthesis of Compound C-235
Compound A-1 (4.0 g,15.1 mmol), N, 4-diphenylaniline (8.2 g,33.3 mmol), pd 2 (dba) 3 (0.693 g,0.757 mmol), spos (0.622 g,1.51 mmol) and NaOt-Bu (1.46 g,15.1 mmol) were added to 80mL of o-xylene and then stirred at 180℃for 0.5 hours under reflux. Thereafter, the mixture was cooled to room temperature, and separated with a silica filter to obtain compound C-235 (4.50 g, yield: 43.6%).
Compounds of formula (I) MW Melting point Color of
C-235 681.82 130.9℃ Yellow colour
Example 2: preparation of Compound C-21
1) Synthesis of Compound C-21
Compound B (4.0 g,15.1 mmol), N-phenyldibenzofuran-3-amine (8.05 g,31.0mmol)、Pd 2 (dba) 3 (0.693 g,0.757 mmol), spos (0.622 g,1.51 mmol) and NaOt-Bu (3.64 g,37.9 mmol) were added to 80mL o-xylene and then stirred at 180℃for 2 hours under reflux. Thereafter, the mixture was cooled to room temperature, and separated with a silica filter to obtain compound C-21 (2.20 g, yield: 20.5%).
Compounds of formula (I) MW Melting point Color of
C-21 709.79 247.8℃ Huang Baise
Example 3: preparation of Compound C-436
1) Synthesis of Compound D-1
Compound D (10.0 g,15.1 mmol), N-phenyldibenzofuran-2-amine (9.24 g,35.6 mmol), pd (OAc) 2 (0.728g，3.24mmol)、P(t-Bu) 3 (2.62 g,6.48 mmol) and NaOt-Bu (7.79 g,81.0 mmol) were added to 160mL of toluene and then stirred at 180℃for 2 hours under reflux. Thereafter, the mixture was cooled to room temperature and oxidized withThe silica filter was separated to obtain compound D-1 (5.00 g, yield: 31.7%).
2) Synthesis of Compound C-436
Compound D-1 (4.4 g,15.1 mmol), N, 2-diphenylaniline (2.44 g,9.94 mmol), pd 2 (dba) 3 (0.693 g,0.757 mmol), spos (0.622 g,1.51 mmol) and NaOt-Bu (3.64 g,37.9 mmol) were added to 50mL of o-xylene and then stirred at 180℃for 2 hours under reflux. Thereafter, the mixture was cooled to room temperature, and separated with a silica filter to obtain compound C-436 (2.00 g, yield: 31.8%).
Compounds of formula (I) MW Melting point Color of
C-436 695.81 179.5℃ Huang Baise
Example 4: preparation of Compound C-437
1) Synthesis of Compound C-437
In a flask, compound E (6.2 g,15.6 mmol), N- ([ 1,1' -biphenyl) was taken upPhenyl group]-4-yl) dibenzo [ b, d]Furan-3-amine (4.73 g,14.1 mmol), pd 2 (dba) 3 (0.64g，0.7mmol)、50％ P(t-Bu) 3 (0.7 mL,1.4 mmol) and NaOt-Bu (2.70 g,22.0 mmol) were added to 70mL of toluene and then stirred at 150℃under reflux. After cooling to room temperature, the mixture was filtered through a celite filter, dissolved in dichloromethane, and separated by column chromatography. After the addition of MeOH, the resulting solid was filtered under reduced pressure to obtain compound C-437 (5.7 g, yield: 58%).
Compounds of formula (I) MW Melting point Color of
C-437 695.82 208℃ Yellow colour
Device examples 1 to 3: fabrication of a co-deposited first host compound and second host compound according to the present disclosure OLED
An OLED according to the present disclosure was fabricated. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (japanese Ji Aoma limited (GEOMATEC co., ltd., japan)) on a glass substrate for OLED was sequentially ultrasonically washed with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Introduction of the Compound HI-1 into vacuum vapor deposition One cell of the device and the compound HT-1 is introduced into the other cell. The two materials were evaporated at different rates, and compound HI-1 was deposited in a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, the compound HT-1 was deposited on the 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 vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby depositing a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: the first host compound and the second host compound shown in table 1 below were introduced as hosts into two cells of a vacuum vapor deposition apparatus, respectively, and the compound D-39 was introduced as a dopant into the other cell. The two host compounds were evaporated at a rate of 1:1 and the dopant materials were simultaneously evaporated at different rates, and the dopants were deposited at a doping amount of 3wt% based on the total of the host and dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Then, the compound ET-1 and the compound EI-1 were evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After depositing the compound EI-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used to make OLEDs are shown at 10 -6 Purification by vacuum sublimation was performed under the tray.
Device comparative example 1: fabrication of an OLED containing only the contrast compound as the host
An OLED was manufactured in the same manner as in device example 1, except that only H2-146 was used as the second host compound as the host of the light-emitting layer.
The driving voltage, the light emitting efficiency and the light emitting color of the OLEDs produced in device examples 1 to 3 and device comparative example 1 at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nit (lifetime; T95) are shown in table 1 below.
TABLE 1
As can be confirmed from table 1 above, the OLEDs (device examples 1 to 3) including the specific combinations of the compounds according to the present disclosure as the host materials exhibited excellent light emitting efficiency and lifetime characteristics while having equal or higher driving voltages, as compared to the OLEDs (device comparative example 1) not including the plurality of host materials according to the present disclosure.
The compounds used in the above device examples 1 to 3 and device comparative example 1 are shown in table 2 below.
TABLE 2
Device example 4: fabricating an OLED deposited with a second hole transport layer according to the present disclosure
An OLED according to the present disclosure was fabricated. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (japanese Ji Aoma limited (GEOMATEC co., ltd., japan)) on a glass substrate for OLED was sequentially ultrasonically washed with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus and the compound HT-3 was introduced into the other cell. The two materials were evaporated at different rates and compound HI-1 was deposited in a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-3 to form a first hole injection layer having a thickness of 10 nm. Subsequently, the compound HT-3 was deposited on the first hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, compound C-235 is introduced into another cell of the vacuum vapor deposition apparatus, and by applying to the cell The compound was evaporated by applying an electric current, thereby depositing a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: the host compounds shown in table 4 below were introduced as hosts into two cells of a vacuum vapor deposition apparatus, and compound D-1 was introduced as a dopant into the other cell. The two materials were evaporated at different rates, and the dopant was deposited at a doping amount of 2wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Subsequently, a compound HBL was deposited on the light emitting layer to form an electron buffer layer having a thickness of 5 nm. Then, the compound ET-2 and the compound EI-1 were evaporated as electron transport materials at a weight ratio of 50:50 to form an electron transport layer having a thickness of 30nm on the electron buffer layer. After depositing the compound EI-1 as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used to make OLEDs are shown at 10 -6 Purification by vacuum sublimation was performed under the tray.
Device comparative example 2
An OLED was fabricated in the same manner as in device example 4, except that compound F was used as the material of the second hole transport layer.
The driving voltage, light emitting efficiency and light emitting color at a luminance of 1,000 nits of the OLED produced in the device example 4 and the device comparative example 2 manufactured as described above are shown in table 3 below.
TABLE 3
As can be confirmed from table 3 above, the OLED (device example 4) including the specific compound according to the present disclosure as the material of the second hole transport layer exhibited equal or higher light emitting efficiency at a much lower driving voltage, as compared to the OLED (device comparative example 2) including no specific compound according to the present disclosure as the material of the second hole transport layer.
The compounds used in the above device example 4 and device comparative example 2 are shown in table 4 below.
TABLE 4
/>

Claims (15)

1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2:
in the formula (1) of the present invention,
X 1 and X 2 Is represented by-n=, and the other is represented by-O-or-S-;
R 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;
ring A represents a (C6-C12) aromatic hydrocarbon;
L 1 and L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
in the formula (2) of the present invention,
T 5 and T 6 、T 7 And T 8 Or all of them are connected to each other to form a ring having the following formula 3;
in the formulae 2 and 3,
t without formation of one or more rings 1 To T 4 、T 9 To T 14 And T 5 To T 8 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 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, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C3-C30) aliphatic ring, substituted or unsubstituted mono-or unsubstituted (C1-C30) alkylamino, substituted or di- (C1-C30) alkylamino, mono-or di- (C30) alkylamino, substituted or di- (C1-C30) alkylamino, di- (C2-or C30) alkylamino, or di (C30-C30) amino Substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino, or-L 3 -Ar 5 Provided that T 1 To T 14 At least one of them represents-L 3 -Ar 5 ；
L 3 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 5 each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
-represents a fused site with formula 2; and is also provided with
The heteroaryl and the heteroarylene contain one or more heteroatoms selected from B, N, O, S, si and P.
2. The plurality of host materials of claim 1, wherein one or more substituents of the substituted alkyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring groups of the one or more aliphatic and one or more aromatic rings, the substituted mono-or di-alkylamino, the substituted mono-or di-alkenylamino, the substituted alkylalkenylamino, the substituted mono-or di-arylamino, the substituted alkylarylamino, the substituted mono-or di-heteroarylamino, the substituted alkylheteroarylamino, the substituted alkenylarylamino, the substituted alkenylheteroarylamino, and the substituted arylheteroarylamino are each independently selected from at least one of the following: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (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; (3-to 30-membered) heteroaryl, unsubstituted or substituted with at least one of (C1-C30) alkyl and (C6-C30) aryl; (C6-C30) aryl, unsubstituted or substituted with at least one of: deuterium, cyano, halogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl and (3-to 30-membered) heteroaryl; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; (C1-C30) alkyl (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
3. The plurality of host materials of claim 1, wherein formula 1 is represented by at least one of the following formulas 4 to 6:
r, X in formulae 4 to 6 1 、X 2 、L 1 、L 2 And Ar 1 To Ar 4 Is as defined in claim 1.
4. The plurality of host materials of claim 1, wherein R and Ar in formula 1 1 To Ar 4 Each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene groupA group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted benzofuropyrimidinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzonaphthyridinyl group, or a substituted or unsubstituted benzonaphthyridinyl group.
5. The plurality of host materials of claim 1, wherein formula 2 is represented by at least one of the following formulas 2-1 and 2-2:
in formulas 2-1 and 2-2,
T 1 to T 4 And T 9 To T 14 Is as defined in claim 1, and
T 5 to T 8 Is T as in claim 1 for the absence of one or more rings 5 To T 8 As defined.
6. The plurality of host materials of claim 1, wherein formula 2 is represented by at least one of the following formulas:
in the above-mentioned formula (i), the water,
T 1 to T 14 Each independently ofAnd standing for hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 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, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted tri (C3-C30) aliphatic ring, substituted or unsubstituted (C3-C30) aromatic ring, substituted or unsubstituted mono-or unsubstituted fused ring groups, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or di- (C1-C30) alkenyl) or amino Substituted or unsubstituted (C1-C30) alkyl (3-to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino, and
L 3 And Ar is a group 5 Is as defined in claim 1.
7. The plurality of host materials of claim 1, wherein Ar in formula 2 5 Is a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzothienoquinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted dibenzoquinazolinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted benzopyrimidinyl group, a substituted or unsubstituted acenaphthylenepyrimidinyl group, a substituted or unsubstitutedSubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzonaphthyridinyl, substituted or unsubstituted benzimidazolyl, or substituted or unsubstituted phenanthroimidazolyl.
8. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
9. the plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
10. an organic electroluminescent compound represented by the following formula 11:
in the case of the method of claim 11,
X 1 and X 2 Is represented by-n=, and the other is represented by-O-or-S-;
r 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;
ring A represents a (C6-C12) aromatic hydrocarbon; and is also provided with
Ar 1 To Ar 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
with the proviso that when ring A is benzeneWhen, -N (Ar) 1 )(Ar 2 ) and-N (Ar) 3 )(Ar 4 ) At ortho or meta positions relative to each other.
11. The organic electroluminescent compound according to claim 10, wherein R is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothienyl.
12. The organic electroluminescent compound according to claim 10, wherein the compound represented by formula 11 is at least one selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
13. an organic electroluminescent device, comprising: an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises the plurality of host materials according to claim 1.
14. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 10.
15. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 10.
CN202310312100.7A 2022-04-05 2023-03-28 Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Pending CN116891442A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2022-0042328 2022-04-05
KR10-2023-0031333 2023-03-09
KR1020230031333A KR20230143559A (en) 2022-04-05 2023-03-09 A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same

Publications (1)

Publication Number Publication Date
CN116891442A true CN116891442A (en) 2023-10-17

Family

ID=88311239

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202310312100.7A Pending CN116891442A (en) 2022-04-05 2023-03-28 Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same

Country Status (1)

Country Link
CN (1) CN116891442A (en)

Similar Documents

Publication Publication Date Title
KR102245910B1 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
CN114835626A (en) Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same
KR20190101281A (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
CN116096202A (en) Multiple host materials and organic electroluminescent device comprising the same
CN112119139A (en) Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN116514629A (en) Multiple host materials and organic electroluminescent device comprising the same
CN116082341A (en) Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same
CN116621790A (en) Multiple host materials and organic electroluminescent device comprising the same
CN115403569A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising same
CN114075193A (en) Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same
CN112239666A (en) Multiple host materials and organic electroluminescent device comprising the same
CN116891442A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117624071A (en) Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same
CN116063338A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117510422A (en) Organic electroluminescent compound, organic electroluminescent material, and organic electroluminescent device comprising the same
CN117384149A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117624223A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN116751189A (en) Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same
CN117586271A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117510423A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117886770A (en) Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same
CN116396281A (en) Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
CN117263891A (en) Multiple host materials and organic electroluminescent device comprising the same
CN117903127A (en) Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same
CN118344281A (en) Multiple host materials and organic electroluminescent device comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication