CN116731002A - Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same Download PDFInfo
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- CN116731002A CN116731002A CN202310203076.3A CN202310203076A CN116731002A CN 116731002 A CN116731002 A CN 116731002A CN 202310203076 A CN202310203076 A CN 202310203076A CN 116731002 A CN116731002 A CN 116731002A
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- organic electroluminescent
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- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present disclosure relates to organic electroluminescent compounds, a plurality of host materials comprising at least one first host compound and at least one second host compound, and organic electroluminescent devices comprising the same. By including the organic electroluminescent compound or a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device having improved driving voltage, light emitting efficiency, and/or lifetime characteristics can be provided.
Description
Technical Field
The present disclosure relates to organic electroluminescent compounds, various host materials, and organic electroluminescent devices including the same.
Background
In 1987, tang et al, eastman Kodak, had developed for the first time a method of forming a light-emitting layer and a charge-transporting layer by using TPD/Alq 3 Double-layered 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. However, 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. In general, the lifetime of an OLED becomes shorter as the luminance of the OLED becomes higher. 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 devices having improved performance, such as improved driving voltage, luminous efficiency, and/or lifetime characteristics, as compared to previously disclosed organic electroluminescent devices.
On the other hand, korean patent application laid-open No. 10-2020-0026079 discloses an organic electroluminescent device comprising a phenanthrooxazole-containing compound as a host material, and korean patent application laid-open No. 10-2021-0006283 discloses an organic electroluminescent device comprising a compound containing phenanthrooxazole and naphthobenzo structures respectively as basic skeletons as a plurality of host materials. However, the above-mentioned references do not specifically disclose an organic electroluminescent device using a specific compound or a specific combination of a plurality of host materials as claimed in the present disclosure, and there is still a need to develop a host material for improving the performance of the organic electroluminescent device.
Disclosure of Invention
Technical problem
It is an 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 another object of the present disclosure to provide a variety of host materials capable of producing an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long life characteristics. It is still another object of the present disclosure to provide an organic electroluminescent device having low driving voltage, high luminous efficiency and/or long life characteristics by including the compound according to the present disclosure as a single host material or including a plurality of host materials including a specific combination of the compounds according to the present disclosure.
Solution to the problem
The inventors of the present invention noted that a compound having a core such as phenanthrooxazole has a low HOMO (highest occupied molecular orbital) energy level in an energy level relationship with a hole transport layer as a hole-type host, and studied a hole-type host capable of forming an appropriate energy gap with a compound for a hole transport layer. On the other hand, the compounds for hole transport layer and the compounds having a phenanthrooxazole skeleton have dihedral angles as molecular forms having appropriate rigidity, but when they have a completely planar structure according to the formation of substituents, they can cause crystallization by aggregation. The present inventors found that the compound containing a terphenyl group at the terminal as shown in the following formula 1 can provide an organic electroluminescent device having a fast current characteristic and a long lifetime because an appropriate intermolecular stack is well established. In particular, when the compound represented by formula 1 is used as a hole-type host, it was confirmed that the energy barrier associated with the hole transport layer is reduced as compared with a hole-type host of a conventional phenanthrooxazole skeleton, and it was found that when it is used in a light-emitting layer in combination with a compound represented by the following formula 2, hole and electron characteristics are balanced by appropriate HOMO and LUMO energy levels, and an organic electroluminescent device having a lower driving voltage, higher luminous efficiency and/or longer life, and at the same time capable of realizing a color of high purity can be provided as compared with a conventional organic electroluminescent device.
In particular, the inventors of the present invention found that the above object can be achieved by 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 wherein the second host compound is represented by the following formula 2.
In the formula (1) of the present invention,
X 1 and Y 1 Each independently represents-N=, -NR 11 -O-, or-S-, provided that X 1 And Y 1 Any one of them represents-n=, and X 1 And Y 1 The other one of (B) represents-NR 11 -, -O-or-S-;
R 1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 2 to R 4 And R is 11 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) arylsilylSubstituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-L 2 -N(Ar 1 )(Ar 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be linked to one or more adjacent substituents to form one or more rings;
R 5 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 6 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 ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 2 -N-(Ar 1 )(Ar 2 )；
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;
Ar 1 and Ar is a group 2 Each independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl 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 (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
n represents an integer of 0 to 3, a represents an integer of 1 to 5, d represents an integer of 1 to 4, and b and c each independently represent an integer of 1 or 2, wherein each R is if a to d is an integer of 2 or more 2 To each R 4 And each R 6 May be the same or different from each other;
in the formula (2) of the present invention,
X 2 represents-O-or-S-;
R 21 and R is 22 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group;
Ar 21 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted terphenyl group;
Ar 22 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group; and is also provided with
a 'represents an integer of 1 to 3, and b' represents an integer of 1 to 4, wherein each R if a 'and b' represent integers of 2 or more 21 And each R 22 May be the same as or different from each other,
in formula 2, one or more substituents of the substituted aryl, substituted phenyl, substituted biphenyl, substituted terphenyl, substituted naphthyl, substituted dibenzofuranyl, and substituted dibenzothiophenyl groups are each independently at least one of deuterium and (C6-C30) aryl.
Furthermore, the present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by the following formula 21.
In the formula (21) of the present invention,
Ar 21 represents unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenylnaphthyl, unsubstituted or deuterium-substituted naphthylphenyl, or unsubstituted or deuterium-substituted terphenyl;
Ar 22 represents a binaphthyl group which is unsubstituted or substituted by deuterium;
R 21 and R is 22 Each independently represents hydrogen or deuterium; and is also provided with
a 'represents an integer of 1 to 3, and b' represents an integer of 1 to 4, wherein each R if a 'and b' represent integers of 2 or more 21 And each R 22 May be the same or different from each other.
Furthermore, the inventors of the present invention found that the above object can be achieved by the following organic electroluminescent compounds.
The beneficial effects of the invention are that
The organic electroluminescent compounds according to the disclosure exhibit properties suitable for use in organic electroluminescent devices. In addition, an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or longer life characteristics compared to conventional organic electroluminescent devices may be manufactured by including the compound according to the present disclosure as a single host material or as a plurality of host materials, and a display system or an illumination system may be manufactured using the organic electroluminescent device.
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 "plurality of organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of two or more compounds, which may be contained in any layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of organic electroluminescent materials may be a combination of two or more compounds that may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The two or more compounds may be contained in the same layer or different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated separately.
The term "multiple host materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of two or more host materials. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. The plurality of host materials of the present disclosure may be contained in any light emitting layer constituting an organic electroluminescent device, wherein two or more compounds contained in the plurality of host materials may be contained together in one light emitting layer or may be contained in different light emitting layers, respectively. When two or more host materials are contained in one layer, they may be mixed-evaporated to form a layer, or co-evaporated separately and simultaneously to form a layer, for example.
Herein, the term "(C1-C30) alkyl" means havingA linear or branched alkyl group of 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C2-C30) alkenyl" in the present disclosure means a straight or branched alkenyl group having 2 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. The term "(C2-C30) alkynyl" in the present disclosure means a straight or branched alkynyl group having 2 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl group may include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methylpent-2-ynyl group and the like. The term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, preferably from 3 to 20 ring backbone carbon atoms, and 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, preferably 5 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) (arylene) aryl" in the present disclosure means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. The number of ring skeleton carbon atoms is preferably 6 to 25, and more preferably 6 to 18. The aryl groups described above may be partially saturated and may contain spiro structures. The aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, and tetracenyl Phenyl, perylene, and,A group, a naphthacene group, a fluoranthene group, a spirobifluorenyl group, an azulene group, a tetramethyldihydrophenanthryl group, and the like. More specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthraceyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, tetracenyl, 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, 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) (ene) heteroaryl" in the present disclosure means an aryl 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 group includes a heteroaryl group(s) formed by connecting at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds, and may contain 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, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuranquinolinyl, benzobenzoquinazolinyl, benzofurannaphthyridinyl, benzofuropyrimidinyl, naphthofuropyrimidinyl, naphthobenzofuranyl, and naphthobenzofuranyl benzothienoquinolinyl, benzothienoquinazolinyl, benzothienonaphthyridinyl, benzothienopyrimidinyl, naphtothienopyrimidinyl, pyrimidoindolyl, benzopyrimidino indolyl, benzofuranopyrazinyl, naphtofuranopyrazinyl, benzothiophenopyrazinyl, naphtothienopyrazinyl, acenaphthopyrazinyl pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, naphthazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, dibenzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, phenanthroimidazolyl, benzodioxolyl, dihydroacridinyl, benzotriazolophenazinyl, imidazopyridinyl, chromene quinazolinyl, thiochromene quinazolinyl, dimethyl benzo pyridyl, indolocarbazolyl, 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 (indodidinyl), 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, azacarbazol-1-yl, azacarbazol-2-yl azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-azanyl, 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. The term "fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings" means a functional group in which at least one aliphatic ring having 3 to 30 ring backbone carbon atoms, preferably 3 to 25 ring backbone carbon atoms, and more preferably 3 to 18 ring backbone carbon atoms, and at least one aromatic ring having 6 to 30 ring backbone carbon atoms, preferably 6 to 25 ring backbone carbon atoms, and more preferably 6 to 18 ring backbone carbon atoms are fused. For example, the fused ring groups may include at least one benzene fused ring group with at least one cyclohexane, or at least one naphthalene fused ring group with at least one cyclopentane, and the like. In the present disclosure, the carbon atoms of the fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings may be replaced by at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. 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. 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.
The term "ring formed by the connection of adjacent substituents" means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted, mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring or combination thereof, preferably a substituted or unsubstituted, mono-or polycyclic (5-to 25-membered) alicyclic or aromatic ring or combination thereof. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. According to one embodiment of the present disclosure, the number of ring backbone atoms is 5 to 20, and according to another embodiment of the present disclosure, the number of ring backbone atoms is 5 to 15.
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, in the formulas of the present disclosure, the one or more substituents of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted fused ring groups of one or more aliphatic and one or more aromatic rings 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; (3-to 30-membered) heteroaryl; (C6-C30) aryl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl; one or more tri (C1-C30) alkylsilyl groups; one or more tri (C6-C30) arylsilyl groups; 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: deuterium; (C1-C20) alkyl; and (C6-C18) aryl unsubstituted or substituted by deuterium or one or more (C6-C18) aryl 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: deuterium; (C1-C10) alkyl; and (C6-C15) aryl unsubstituted or substituted by deuterium or one or more (C6-C30) aryl groups. For example, one or more substituents may each independently be deuterium, methyl, phenyl that is unsubstituted or substituted with one or more naphthyl, biphenyl that is unsubstituted or substituted with deuterium, naphthyl that is unsubstituted or substituted with one or more phenyl, and the like.
The plurality of host materials according to the present disclosure include a first host material including a compound represented by formula 1 and a second host material including a compound represented by formula 2, and may be included in a light emitting layer of an organic electroluminescent device according to the present disclosure.
Hereinafter, the compound represented by formula 1 will be described in more detail.
In formula 1, X 1 And Y 1 Each independently represents-N=, -NR 11 -O-, or-S-, provided that X 1 And Y 1 Any one of them represents-n=, and X 1 And Y 1 The other one of (B) represents-NR 11 -, -O-or-S-. For example, X 1 And Y 1 Any of which may be-n=, and X 1 And Y 1 The other of (C) may be-O-.
In formula 1, R 1 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, R 1 May be a substituted or unsubstituted (C6-C18) aryl group. According to another embodiment of the disclosure, R 1 May be an unsubstituted (C6-C12) aryl group. For example, R 1 Phenyl, naphthyl, and the like are possible.
In formula 1, R 2 To R 4 And R is 11 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 ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 2 -N(Ar 1 )(Ar 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings. For example, R 2 To R 4 And R is 11 May be hydrogen.
In formula 1, R 5 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, R 5 May be a substituted or unsubstituted (C6-C20) aryl group, or a substituted or unsubstituted (3-to 20-membered) heteroaryl group. According to another embodiment of the disclosure, R 5 May be a (C6-C18) aryl group, unsubstituted or substituted with one or more (C1-C10) alkyl groups, or an unsubstituted (3-to 18-membered) heteroaryl group. For example, R 5 May be phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, etc.
According to another embodiment of the disclosure, R 5 May be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzeneA fluorene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted benzofuranyl group.
In formula 1, R 6 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 ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 2 -N(Ar 1 )(Ar 2 ). For example, R 6 May be hydrogen.
In formula 1, 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 May be a single bond, or a substituted or unsubstituted (C6-C18) arylene group. According to another embodiment of the present disclosure, L 1 May be a single bond, or an unsubstituted (C6-C12) arylene group. For example, L 1 May be a single bond, phenylene, etc.
In formula 1, ar 1 And Ar is a group 2 Each independently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl 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 (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In formula 1, n represents an integer of 0 to 3, a represents an integer of 1 to 5, d represents an integer of 1 to 4, and b and c are each independently representedAn integer of 1 or 2, wherein each R is if a to d are integers of 2 or more 2 To each R 4 And each R 6 May be the same or different from each other. For example, n may be an integer of 0 or 1.
According to one embodiment of the present disclosure, formula 1 may be represented by the following formula 1-1.
In formula 1-1, d represents an integer of 1 to 3, wherein each R is if d is an integer of 2 or more 4 May be the same or different from each other; and X is 1 、Y 1 、R 1 To R 6 、L 1 N, and a to c are as defined in formula 1.
According to one embodiment of the present disclosure, formula 1 may be represented by at least one of the following formulas 1-1-1 to 1-1-4.
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In the formulae 1-1-1 to 1-1-4, d represents an integer of 1 to 3, wherein each R is if d is an integer of 2 or more 4 May be the same or different from each other; and X is 1 、Y 1 、R 1 To R 6 、L 1 N, and a to c are as defined in formula 1.
Hereinafter, the compound represented by formula 2 will be described in more detail.
In formula 2, X 2 represents-O-or-S-.
In formula 2, R 21 And R is 22 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group. According to one embodiment of the present disclosure, R 21 And R is 22 Each independently can be hydrogen, deuterium, or substituted or unsubstituted (C6-C20 Aryl group). According to another embodiment of the disclosure, R 21 And R is 22 Each independently can be hydrogen, deuterium, or a (C6-C18) aryl group that is unsubstituted or substituted with deuterium or one or more (C6-C18) aryl groups. For example, R 21 And R is 22 Each independently may be hydrogen, deuterium, phenyl unsubstituted or substituted with one or more naphthyl, biphenyl, naphthyl unsubstituted or substituted with one or more phenyl, phenanthryl, and the like.
In formula 2, ar 21 Represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted terphenyl group. According to one embodiment of the present disclosure, ar 21 Naphthyl which may be unsubstituted or substituted by one or more (C6-C30) aryl groups; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups; or unsubstituted terphenyl. According to another embodiment of the present disclosure, ar 21 Naphthyl which may be unsubstituted or substituted by one or more (C6-C18) aryl groups; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl groups; or unsubstituted terphenyl. For example, ar 21 Naphthyl which may be unsubstituted or substituted by one or more phenyl groups, one or more naphthyl groups, or one or more biphenyl groups; dibenzofuranyl that is unsubstituted or substituted with one or more phenyl groups, one or more naphthylphenyl groups, one or more unsubstituted or deuterium-substituted biphenyl groups, one or more naphthyl groups, or one or more phenylnaphthyl groups; terphenyl, and the like.
In formula 2, ar 22 Represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group. According to one embodiment of the present disclosure, ar 22 May be phenyl unsubstituted or substituted with one or more (C6-C30) aryl groups, unsubstituted biphenyl, naphthyl unsubstituted or substituted with one or more (C6-C30) aryl groups, or unsubstituted terphenyl. According to another embodiment of the present disclosure, ar 22 May be unsubstitutedOr phenyl substituted with one or more (C6-C18) aryl groups, unsubstituted biphenyl groups, unsubstituted or naphthyl substituted with one or more (C6-C12) aryl groups, or unsubstituted terphenyl groups. For example, ar 22 Phenyl which may be unsubstituted or substituted by one or more naphthyl groups; a biphenyl group; naphthyl, unsubstituted or substituted by one or more phenyl groups or one or more naphthyl groups; terphenyl, and the like.
In formula 2, a 'represents an integer of 1 to 3, and b' represents an integer of 1 to 4, wherein each R if a 'and b' represent integers of 2 or more 21 And each R 22 May be the same or different from each other.
In formula 2, the substituents of the substituted aryl, substituted phenyl, substituted biphenyl, substituted terphenyl, substituted naphthyl, substituted dibenzofuranyl, and substituted dibenzothiophenyl are each independently at least one of deuterium and (C6-C30) aryl.
According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas 2-1 to 2-4.
In the formulae 2-1 to 2-4, X 2 、Ar 21 、Ar 22 、R 21 、R 22 A ', and b' are 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 2 may be at least one selected from the following compounds, but is not limited thereto.
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The combination of at least one of the compounds H1-1 to H1-20 and at least one of the compounds H2-1 to H2-75 may be used in an organic electroluminescent device.
Hereinafter, an organic electroluminescent compound according to an embodiment of the present disclosure will be described.
The organic electroluminescent compound according to an embodiment of the present disclosure is represented by the following formula 21.
In the formula (21) of the present invention,
Ar 21 represents unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenylnaphthyl, unsubstituted or deuterium-substituted naphthylphenyl, or unsubstituted or deuterium-substituted terphenyl;
Ar 22 represents a binaphthyl group which is unsubstituted or substituted by deuterium;
R 21 and R is 22 Each independently represents hydrogen or deuterium; and is also provided with
a' tableAn integer of 1 to 3, and b ' represents an integer of 1 to 4, wherein each R if a ' and b ' represent an integer of 2 or more 21 And each R 22 May be the same or different from each other.
According to one embodiment of the present disclosure, ar 21 Can be unsubstituted or deuterium-substituted naphthyl.
According to one embodiment of the present disclosure, ar 22 Represented by one of the following formulas a-1 and a-2.
In formulas A-1 and A-2, the hydrogen of naphthalene may be replaced with deuterium.
According to one embodiment of the present disclosure, formula 21 is represented by formula 21-1 below.
In formula 21-1, ar 21 、Ar 22 、R 21 、R 22 A ', and b' are as defined in formula 21.
The compound represented by formula 21 may be at least one selected from the following compounds, but is not limited thereto.
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The organic electroluminescent compound according to another embodiment of the present disclosure is selected from the following compounds.
The compounds represented by formulas 1 and 2 according to the present disclosure may be produced by synthetic methods known to those skilled in the art. For example, the compound represented by formula 1 according to the present disclosure may be produced by referring to korean patent application publication nos. 2017-0022865 (published 3/2/2017) and 2018-0099487 (published 9/5/2018), and the compound represented by formula 2 or 21 according to the present disclosure may be produced by referring to the following reaction scheme 1, but is not limited thereto.
Reaction scheme 1
In reaction scheme 1, X 2 、Ar 21 、Ar 22 、R 21 、R 22 A ', and b' are as defined in formula 2, R represents hydrogen or (C1-C30) alkyl, and Hal means halogen.
Although illustrative synthetic examples of compounds represented by formula 2 or 21 are described above, those skilled in the art will readily understand that they are all based on Buchwald-Hartmann (Buchwald-Hartwig) cross-coupling reactions, N-arylation reactions, acidified montmorillonite (H-mont) mediated etherification reactions, miyaura) boronation reactions, suzuki (Suzuki) cross-coupling reactions, intramolecular acid-induced cyclization reactions, pd (II) catalyzed oxidative cyclization reactions, grignard reactions (Grignard Reaction), heck reactions (Heck reactions), dehydrative cyclization reactions, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like, and even when substituents defined in formula 2 or 21 other than the substituents specified in the specific synthesis examples are bonded, the above reaction proceeds.
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, wherein the organic layer may include a plurality of organic electroluminescent materials including a compound represented by formula 1 as a first organic electroluminescent material and a compound represented by formula 2 as a second organic electroluminescent material, or may include an organic electroluminescent material including a compound represented by formula 21. According to one embodiment of the present disclosure, an organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one light emitting layer between the anode and the cathode, wherein the light emitting layer may include a compound represented by formula 1 and a compound represented by formula 2 or a compound represented by formula 21.
The light emitting layer includes a host and a dopant, wherein the host includes a plurality of host materials or organic electroluminescent compounds, the compound represented by formula 1 may be included as a first host compound of the plurality of host materials, and the compound represented by formula 2 may be included as a second host compound of the plurality of host materials. Herein, the weight ratio of the first host compound to the second host compound is from about 1:99 to about 99:1, preferably from about 10:90 to about 90:10, more preferably from about 30:70 to about 70:30, still more preferably from about 40:60 to about 60:40, even more preferably about 50:50.
In the present disclosure, the light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the various host materials of the present disclosure, both the first host material and the second host material may be contained in one layer, or the first host material and the second host material may be contained in different light emitting layers, respectively. According to one embodiment of the present disclosure, the dopant compound may have a doping concentration of less than 20wt% with respect to the host compound of the light emitting layer.
The organic electroluminescent device of the present disclosure 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 injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. According to one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound as at least one of a hole injection material, a hole transport material, a hole assist material, a light emitting assist material, and an electron blocking material, in addition to the plurality of host materials or the organic electroluminescent compound of the present disclosure. Further, according to an embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound as at least one of an electron transporting material, an electron injecting material, an electron buffering material, and a hole blocking material, in addition to the plurality of host materials or the organic electroluminescent compound of the present disclosure.
A variety of host materials or organic electroluminescent compounds according to the present disclosure 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, various host materials or organic electroluminescent compounds according to one embodiment of the present disclosure may also be used in organic electroluminescent devices comprising Quantum Dots (QDs).
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 plurality of layers so as 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 plurality of layers may use two compounds at the same time. In addition, the hole injection layer may be doped with a p-type dopant. An electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing the light emitting layer to prevent light emission leakage. The hole transporting layer or the electron blocking layer may be a multilayer, wherein a plurality of compounds may be used in each of the 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 multilayer in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein two compounds may be simultaneously used in each of the multilayer. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein a plurality of compounds may be used in each of the multilayer. In addition, the electron injection layer may be doped with an n-type dopant.
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 isoquinoline, 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 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 linked to one or more adjacent substituents to form one or more rings; and is also provided with
s represents an integer of 1 to 3.
Specific examples of the dopant compounds are as follows, but are not limited thereto.
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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 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.
In addition, the first and second host compounds of the present disclosure may be formed into films by the methods listed above, typically by co-evaporation or mixed evaporation. Co-evaporation is a hybrid deposition process in which two or more materials are placed into respective single crucible sources and an electric current is applied to both chambers simultaneously to evaporate the materials. Hybrid evaporation is a hybrid deposition method in which two or more materials are mixed in one crucible source before they are evaporated, and an electric current is applied to one cell to evaporate the materials. Further, when the first host compound and the second host compound are present in the same layer or different layers of the organic electroluminescent device, each of the two host compounds may form a film separately. For example, the second host compound may be deposited after the first host compound is deposited.
The present disclosure may provide a display device by using a variety of host materials including a compound represented by formula 1 and a compound represented by formula 2 or an organic electroluminescent compound represented by formula 21. That is, a display system or an illumination system may be manufactured by using various host materials or organic electroluminescent compounds of the present disclosure. In particular, a display system, such as a display system for a white organic light emitting device, a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using various host materials or organic electroluminescent compounds 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 characteristics of an organic electroluminescent device (OLED) including various host materials or organic electroluminescent compounds of the present disclosure will be explained with reference to representative compounds of the present disclosure. However, the following examples are merely to describe the characteristics of an OLED including the compound according to the present disclosure and various host materials or organic electroluminescent compounds according to the present disclosure, but the present disclosure is not limited to the following examples.
Example 1: preparation of Compound H1-17
Compound 1-1 (91.5 g,222 mmol), compound 1-2 (70 g,162.9 mmol), pd (OAc) 2 (560 mg,0.0025 mmol), X-Phos (2-bicyclophosphino-2 ',4',6' -triisopropylbiphenyl) (1.01 g,0.002 mmol), naOtBu (30.6 g,318.4 mmol) and 2500mL of toluene were added to the flask, followed by stirring at 95℃for 48 hours. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H1-17 (34 g, yield: 30%).
| MW | Melting point | |
| H1-17 | 704.83 | 200.5℃ |
Example 2: preparation of Compound H1-16
Compound 2-1 (15 g,36.4 mmol), compound 1-2 (10.9 g,33.1 mmol), pd 2 (dba) 3 (1.56 g,1.7 mmol), S-Phos (2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl) (1.35 g,3.31 mmol), naOtBu (6.36 g,66.2 mmol) and 170mL of xylene were added to the flask followed by stirring at 130℃for 2 hours. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H1-16 (4.3 g, yield: 18%).
| MW | Melting point | |
| H1-16 | 704.83 | 230℃ |
Example 3: preparation of Compound H2-1
1) Synthesis of Compound 3-1
2, 6-Dibromonaphthalene (20 g,70 mmol), phenylboronic acid (9 g,73.4 mmol), K 2 CO 3 (24g，175mmol)、Pd(PPh 3 ) 4 (4 g,3.5 mmol), 350mL toluene, 170mL H 2 O, and 170mL of ethanol were added to the flask, followed by reflux at 130℃for 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 3-1 (13 g, yield: 67%).
2) Synthesis of Compound 3-2
Compound 3-1 (13 g,45.9 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (17.5 g,68.8 mmol), KOAc (11.3 g,114.75 mmol), pdCl 2 (PPh 3 ) 2 (3.2 g,4.59 mmol), and 230mL of 1, 4-dioxane were added to the flask followed by reflux at 150℃for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 3-2 (9 g, yield: 59.3%).
3) Synthesis of Compound H2-1
Compound 3-2 (6.4 g,19.16 mmol), compound 3-3 (6.5 g,15.96 mmol), K 2 CO 3 (5.5g，39.9mmol)、Pd(PPh 3 ) 4 (92mg, 0.798 mmol), 80mL toluene, 40mL ethanol, and 40mL H 2 O was added to the flask followed by reflux at 130 ℃ for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-1 (4.9 g, yield: 53.3%).
| MW | Melting point | |
| H2-1 | 575.20 | 242.5℃ |
Example 4: preparation of Compound H2-3
1) Synthesis of Compound 3-3
2, 4-dichloro-6- (naphthalen-2-yl) -1,3, 5-triazine (58 g,212 mmol), dibenzo [ b, d]Furan-1-ylboronic acid (30 g,141 mmol), na 2 CO 3 (45g，424mmol)、Pd(PPh 3 ) 4 (4.9 g,7.05 mmol), 1.4L toluene and 352mL H 2 O was added to the flask followed by reflux at 100 ℃ for 18 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 3-3 (30 g, yield: 52%).
2) Synthesis of Compound H2-3
Compound 3-3 (6 g,14.7 mmol), 4- (naphthalen-2-yl)Phenyl boronic acid (5.8 g,17.64 mmol), K 2 CO 3 (5.0g，36.75mmol)、Pd(PPh 3 ) 4 (0.85 mg,0.73 mmol), 70mL toluene, 35mL ethanol, and 35mL H 2 O was added to the flask followed by reflux at 130 ℃ for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining moisture was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-3 (4.9 g, yield: 58%).
| MW | Melting point | |
| H2-3 | 575.20 | 192.9℃ |
Example 5: preparation of Compound H2-39
1) Synthesis of Compound 2
Compound 1 (5 g,12.2 mmol), 3-chloronaphthalen-2-ylboronic acid (3 g,14.7 mmol), pd (PPh) 3 ) 4 (704mg，0.61mmol)、K 2 CO 3 (4.2 g,30.2 mmol), 60mL toluene, 30mL ethanol, and 30mL H 2 O was added to the flask followed by stirring at 130℃for 1 hour. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate.Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound 2 (6 g, yield: 92%).
2) Synthesis of Compound H2-39
Compound 2 (4 g,7.48 mmol), phenylboronic acid (1.1 g,8.23 mmol), pd 2 (dba) 3 (340mg，0.374mmol)、S-Phos(246mg，0.598mmol)、K 3 PO 4 (3.97 g,18.7 mmol), and 70mL of xylene were added to the flask, followed by stirring at 130℃under reflux for 12 hours. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-39 (1.4 g, yield: 32.5%).
| MW | Melting point | |
| H2-39 | 575.20 | 216.8℃ |
Example 6: preparation of Compound H2-41
Compound 1 (8.2 g,24.8 mmol), 4, 5-tetramethyl-2- (3-phenyl) Naphthalen-1-yl) -1,3, 2-dioxaborolan (12 g,29.8 mmol), pd (PPh) 3 ) 4 (1.4mg，1.24mmol)、K 2 CO 3 (8.6 g,62 mmol), 120mL toluene, 60mL ethanol, and 60mL H 2 O was added to the flask followed by stirring at 130℃for 1 hour. The mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-41 (4.1 g, yield: 28.7%).
| MW | Melting point | |
| H2-41 | 575.20 | 159.6℃ |
Example 7: preparation of Compound H2-44
Compound 7-1 (8.5 g,15.91 mol), phenylboronic acid (2.3 g,19.10 mmol), K 3 PO 4 (8.4g，39.77mmol)、S-Phos(653mg，1.591mmol)、Pd 2 (dba) 3 (1.4 g,1.591 mmol) and 100mL of toluene were added to the flask, followed by stirring at 130℃under reflux for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the remaining water was extracted with magnesium sulfateAnd (5) removing. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-44 (4.0 g, yield: 43%).
| MW | Melting point | |
| H2-44 | 575.67 | 231.9℃ |
Example 8: preparation of Compound H2-42
1) Synthesis of Compound 8-3
Compound 8-1 (21.0 g,72.77 mmol), compound 8-2 (35.6 g,87.32 mmol), pd (pph) 3 ) 4 (4.2 g,3.64 mmol), and K 2 CO 3 (138.21 g,149.54 mmol) was dissolved in 365mL toluene, 90mL ethanol and 90mL H 2 O and stirred at reflux for 2 hours. The mixture was cooled to room temperature. Will H 2 O was added to the reaction in which the solid formed, and the mixture was stirred for 30 minutes and filtered. The filtrate was recrystallized to obtain compound 8-3 (33.1 g, yield: 85.3%).
2) Synthesis of Compound H2-42
Compound 8-3 (10.0 g,18.73 mmol), phenylboronic acid (9.2 g,74.90 mm)ol)、Pd 2 (dba) 3 (1.8 g,1.88 mmol), S-Phos (0.8 g,3.74 mmol), and K 3 PO 4 (20.0 g,93.64 mmol) was dissolved in 150mL o-xylene and stirred at reflux for 2 hours 30 minutes. The mixture was cooled to room temperature, filtered through celite, separated by column chromatography, and recrystallized to obtain compound H2-42 (3.0 g, yield: 28.0%).
| MW | Melting point | |
| H2-42 | 575.66 | 227℃ |
Example 9: preparation of Compound H2-46
Compound 9-1 (15.2 g,46.03 mmol), compound 9-2 (22.5 g,55.23 mmol), pd (pph) 3 ) 4 (2.7 g,2.30 mmol), and K 2 CO 3 (12.7 g,92.06 mmol) was dissolved in 230mL toluene, 60mL ethanol and 60mL H 2 O and stirred at reflux for 3 hours. The mixture was cooled to room temperature. Will H 2 O was added to the reaction in which the solid was formed, and the mixture was stirred for 30 minutes, and then filtered. The filtrate was filtered through silica, and then recrystallized to obtain compound H2-46 (19.6 g, yield: 73.9％)。
| MW | Melting point | |
| H2-46 | 575.66 | 209℃ |
Example 10: preparation of Compound H2-37
Compound 10-1 (4.6 g,13.93 mmol), compound 10-2 (5.6 g,13.93 mmol), pd (pph) 3 ) 4 (0.8g，0.696mmol)、K 2 CO 3 (5.7g，41.79mmol)、20mL H 2 O, 20mL of ethanol, and 80mL of toluene were added to the flask, followed by stirring at reflux for 2 hours. After the reaction was completed, the mixture was cooled to room temperature. Then, methanol was added dropwise to the mixture, and filtered. The filtrate was dissolved in o-xylene, and filtered through silica to obtain compound H2-37 (3.9 g, yield: 48%).
| MW | Melting point | |
| H2-37 | 575.6 | 264.1℃ |
Example 11: preparation of Compound H2-43
Compound 11-1 (4.4 g,13.48 mmol), compound 11-2 (5 g,12.25 mmol), pd (pph) 3 ) 4 (0.7g，0.612mmol)、K 2 CO 3 (5.1g，36.77mmol)、20mL H 2 O, 20mL of ethanol, and 80mL of toluene were added to the flask, followed by stirring at reflux for 2 hours. After the reaction was completed, the mixture was cooled to room temperature. Then, methanol was added dropwise to the mixture, and filtered. The filtrate was dissolved in o-xylene, and filtered through silica to obtain compound H2-43 (4.6 g, yield: 65%).
| MW | Melting point | |
| H2-43 | 575.6 | 224.9℃ |
Example 12: preparation of Compound H2-61
Compound 12-1 (10 g,24.5 mmol), compound 12-2 (3 g,14.7 mmol), pd (PPh) 3 ) 4 (1.4g，1.225mmol)、K 2 CO 3 (6.7 g,49 mmol), 120mL toluene, 60mL ethanol, and 60mL H 2 O was added to the flask followed by stirring at 130℃for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-61 (13 g, yield: 84%).
| MW | Melting point | |
| H2-61 | 625.73 | 229.1℃ |
Example 13: preparation of Compound H2-64
Compound 13-1 (10 g,18.7 mmol), naphthalene-1-yl-boronic acid (6.5 g,37.4 mmol), pd 2 (dba) 3 (856mg，0.935mmol)、S-Phos(767mg，1.87mmol)、K 3 PO 4 (9.9 g,46.75 mmol), and 93.5mL of xylene were added to the flask, followed by stirring at 160℃for 18 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was extracted with ethyl acetate. Residual moisture in the extracted organic layer was removed with magnesium sulfate. Thereafter, the organic layer was dried and separated by column chromatography to obtain compound H2-64 (4.4 g, yield: 37.6%).
| MW | Melting point | |
| H2-64 | 625.73 | 237.2℃ |
Device examples 1 to 6: producing an OLED comprising a plurality of host materials according to the present disclosure
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (japanese Ji Aoma limited (GEOMATECCO., 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 shown in Table 7 was introduced into a small vacuum vapor deposition apparatus In a chamber and the compound HT-1 is introduced into another cell. The two materials were evaporated at different rates to deposit the compound HI-1 in a doping amount of 3wt% based on the total amount of the compound HI-1 and the 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: each of the first host compound and the second host compound shown in tables 1 to 3 below was introduced as a host into two cells of a vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into the other cell. The two host materials 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 amount of host and dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Then, the compound ETL-1 and the compound EIL-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 EIL-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 for producing the OLED are shown in 10 -6 Purification by vacuum sublimation was performed under the tray.
Comparative examples 1 to 5: producing an OLED comprising a combination of hosts not according to the present disclosure
OLEDs were produced in the same manner as in device examples 1 to 6, except that the host compounds shown in tables 1 to 3 were used as the first host compound of the light-emitting layer.
The driving voltage, the light emitting efficiency and the light emitting color 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) of the organic electroluminescent devices of the device examples 1 to 6 and the comparative examples 1 to 5 produced as described above are shown in the following tables 1 to 3.
[ Table 1 ]
[ Table 2 ]
[ Table 3 ]
As can be confirmed from the above tables 1 to 3, the OLEDs (device examples 1 to 6) comprising the specific combinations of the compounds according to the present disclosure as host materials exhibited lower driving voltages and/or higher luminous efficiencies and significantly improved lifetime characteristics compared to the OLEDs (comparative examples 1 to 5) comprising the host combinations not according to the present disclosure.
[ feature analysis ]
To support the theory of the combination of host materials and electron transport regions according to the present disclosure, hole-only devices (HODs) were produced to confirm and compare hole current characteristics in the devices based on the characteristics of biphenyl and terphenyl in phenanthrooxazole derivatives. The structure of the hole-only device is as follows.
Hole-only device (HOD) example
The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 shown in Table 7 was introduced into the cell of a vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -7 And (5) a bracket. Thereafter, a current was applied to the cells to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 10nm on the ITO substrate. Introduction of the Compound HI-1 into vacuum vapor depositionOne cell of the device and the compound HT-1 is introduced into the other cell. The two materials were evaporated at different rates to deposit the compound HI-1 in a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a first hole transport layer having a thickness of 10 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 10nm 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 compounds shown in table 4 below were introduced into one cell of a vacuum vapor deposition apparatus and evaporated to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Then, the compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus, and the compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates to deposit the compound HI-1 in a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form an electron blocking layer having a thickness of 10nm on the light emitting layer. Then, an Al cathode having a thickness of 80nm was deposited on the electron blocking layer by using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used for producing the OLED are shown in 10 -7 Purification by vacuum sublimation was performed under the tray.
Table 4 below shows the current density (mA/cm) up to a voltage of 2V 2 ) The voltage depends on the material of the light-emitting layer of the hole-only device produced as described above.
[ Table 4 ]
| Light-emitting layer | Current Density (mA/cm) 2 ) |
| Reference-1 | 11 |
| H1-16 | 20 |
As can be confirmed from table 4 above, the hole-only device comprising the compound according to the present disclosure exhibited higher current density and faster hole current characteristics than the hole-only device comprising the compound not according to the present disclosure. In comparing HOMO levels of compounds contained in the second hole transport layer and the light-emitting layer in the hole-device-only example, the biphenyl group-containing compound reference-1 and the terphenyl group-containing compound H1-16 have energy levels of-4.95 eV and-4.92 eV, respectively, and the compound HT-2 contained in the second hole transport layer has an energy level of-4.88 eV. Thus, without being limited by theory, it can be confirmed that a hole-only device comprising the compound according to the present disclosure smoothly injects holes from the hole transport layer into the light emitting layer. Accordingly, the organic electroluminescent device including the compound according to the present disclosure may exhibit low driving voltage, high luminous efficiency, and/or long life characteristics.
Device examples 7 to 12: producing an OLED comprising a plurality of host materials according to the present disclosure
An OLED was produced in the same manner as in device examples 1 to 6, except that compound HT-3 and compound HT-4 were used instead of compound HT-1 and compound HT-2, respectively, and the compounds shown in Table 5 were used as the first host compound and the second host compound of the light emitting layer.
The driving voltage, the luminous efficiency and the luminous color of the OLEDs of device examples 7 to 12 produced as described above 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 5 below.
[ Table 5 ]
Device example 13: producing an OLED comprising a unitary host material according to the present disclosure
An OLED was produced in the same manner as in device example 7, except that only the host compound shown in table 6 below was used as the host material of the light-emitting layer.
Comparative example 6: production of OLEDs comprising conventional host materials
An OLED was produced in the same manner as in device example 13, except that the host compound shown in table 6 below was used as a host material of the light-emitting layer.
The luminous efficiency and the emission color at a luminance of 1,000 nits of the OLED of device example 13 and comparative example 6 produced as described above are shown in table 6 below.
[ Table 6 ]
As can be confirmed from table 6 above, the OLED including the organic electroluminescent compound according to the present disclosure as a single host material exhibited higher luminous efficiency as compared to the OLED including the conventional host material.
Device example 14: producing an OLED comprising a plurality of host materials according to the present disclosure
An OLED was produced in the same manner as in device example 7, except that compound HT-5 was used instead of compound HT-4, and the compounds shown in table 7 were used as the first host compound and the second host compound of the light-emitting layer.
Comparative example 7: production of OLEDs comprising conventional host materials
An OLED was produced in the same manner as in device example 14, except that the host compound shown in table 7 below was used as the host material of the light-emitting layer.
The driving voltage, power efficiency and emission color 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) of the OLEDs of device example 14 and comparative example 7 produced as described above are shown in table 7 below.
[ Table 7 ]
As can be confirmed from table 7 above, the OLED including the plurality of host materials according to the present disclosure exhibited lower driving voltage, higher power efficiency, and excellent lifetime characteristics as compared to the OLED including the conventional host material.
The compounds used in the device examples, comparative examples and hole-only device examples are shown in table 8 below.
[ Table 8 ]
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Claims (16)
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 Y 1 Each independently represents-N=, -NR 11 -O-, or-S-, provided that X 1 And Y 1 Any one of them represents-n=, and X 1 And Y 1 The other one of (B) represents-NR 11 -, -O-or-S-;
R 1 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 2 to R 4 And R is 11 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 ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 2 -N(Ar 1 )(Ar 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be linked to one or more adjacent substituents to form one or more rings;
R 5 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 6 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 ring and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring group, or-L 2 -N-(Ar 1 )(Ar 2 )；
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;
Ar 1 and Ar is a group 2 Each of which is a single pieceIndependently represents hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl 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 (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
n represents an integer of 0 to 3, a represents an integer of 1 to 5, d represents an integer of 1 to 4, and b and c each independently represent an integer of 1 or 2, wherein each R is if a to d is an integer of 2 or more 2 To each R 4 And each R 6 May be the same or different from each other;
in the formula (2) of the present invention,
X 2 represents-O-or-S-;
R 21 and R is 22 Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group;
Ar 21 represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted terphenyl group;
Ar 22 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group; and is also provided with
a 'represents an integer of 1 to 3, and b' represents an integer of 1 to 4, wherein each R if a 'and b' represent integers of 2 or more 21 And each R 22 May be the same as or different from each other,
in formula 2, one or more substituents of the substituted aryl, the substituted phenyl, the substituted biphenyl, the substituted terphenyl, the substituted naphthyl, the substituted dibenzofuranyl, and the substituted dibenzothienyl are each independently at least one of deuterium and (C6-C30) aryl.
2. The plurality of host materials of claim 1, wherein in formula 1, the substituted alkyl, the substituted alkenyl, 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, and one or more substituents of the substituted fused ring groups of one or more aliphatic and one or more aromatic rings 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; (3-to 30-membered) heteroaryl; (C6-C30) aryl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl; one or more tri (C1-C30) alkylsilyl groups; one or more tri (C6-C30) arylsilyl groups; 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 the following formula 1-1:
in the case of the formula 1-1,
d represents an integer of 1 to 3, wherein if d is an integer of 2 or more, each R 4 May be the same or different from each other; and is also provided with
X 1 、Y 1 、R 1 To R 6 、L 1 N, and a to c are as defined in claim 1.
4. The plurality of host materials of claim 1, wherein formula 1 is represented by at least one of the following formulas 1-1-1 to 1-1-4:
in the formulae 1-1-1 to 1-1-4,
d represents an integer of 1 to 3, wherein if d is an integer of 2 or more, each R 4 May be the same or different from each other; and is also provided with
X 1 、Y 1 、R 1 To R 6 、L 1 N, and a to c are as defined in claim 1.
5. The plurality of host materials of claim 1, wherein R 5 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 phenanthryl group, a substituted or unsubstituted anthryl 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 carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted benzofuranyl group.
6. The plurality of host materials of claim 1, wherein formula 2 is represented by at least one of the following formulas 2-1 to 2-4:
in the formulae 2-1 to 2-4, X 2 、Ar 21 、Ar 22 、R 21 、R 22 A ', and b' are as defined in claim 1.
7. 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:
8. 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:
9. 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 of claim 1.
10. An organic electroluminescent compound represented by the following formula 21:
in the formula (21) of the present invention,
Ar 21 represents unsubstituted or deuterium-substituted naphthyl, unsubstituted or deuterium-substituted phenylnaphthyl, unsubstituted or deuterium-substituted naphthylphenyl, or unsubstituted or deuterium-substituted terphenyl;
Ar 22 represents a binaphthyl group which is unsubstituted or substituted by deuterium;
R 21 and R is 22 Each independently represents hydrogen or deuterium; and is also provided with
a 'represents an integer of 1 to 3, and b' represents an integer of 1 to 4, wherein each R if a 'and b' represent integers of 2 or more 21 And each R 22 May be the same or different from each other.
11. The organic electroluminescent compound according to claim 10, wherein the formula 21 is represented by the following formula 21-1:
in formula 21-1, ar 21 、Ar 22 、R 21 、R 22 A ', and b' are as defined in claim 10.
12. The organic electroluminescent compound according to claim 10, wherein Ar 22 Represented by one of the following formulas A-1 and A-2:
in formulas A-1 and A-2, the hydrogen of the naphthalene may be substituted with deuterium.
13. The organic electroluminescent compound according to claim 10, wherein the organic electroluminescent compound represented by formula 21 is selected from the group consisting of:
/>
14. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 10.
15. An organic electroluminescent compound selected from the group consisting of:
16. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 15.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2022-0029217 | 2022-03-08 | ||
| KR1020230016598A KR20230132367A (en) | 2022-03-08 | 2023-02-08 | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same |
| KR10-2023-0016598 | 2023-02-08 |
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| CN116731002A true CN116731002A (en) | 2023-09-12 |
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| CN202310203076.3A Pending CN116731002A (en) | 2022-03-08 | 2023-03-06 | Organic electroluminescent compound, various host materials, and organic electroluminescent device comprising the same |
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| CN (1) | CN116731002A (en) |
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