CN116724685A - Organic electroluminescent device and organic compound for organic electroluminescent device - Google Patents

Organic electroluminescent device and organic compound for organic electroluminescent device Download PDF

Info

Publication number
CN116724685A
CN116724685A CN202280009412.4A CN202280009412A CN116724685A CN 116724685 A CN116724685 A CN 116724685A CN 202280009412 A CN202280009412 A CN 202280009412A CN 116724685 A CN116724685 A CN 116724685A
Authority
CN
China
Prior art keywords
chemical formula
group
compound
organic electroluminescent
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202280009412.4A
Other languages
Chinese (zh)
Inventor
金纹秀
韩甲钟
吴唯真
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Leputo Co ltd
Original Assignee
Leputo Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Leputo Co ltd filed Critical Leputo Co ltd
Publication of CN116724685A publication Critical patent/CN116724685A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups

Abstract

An organic electroluminescent device according to an embodiment of the present invention includes: a first electrode; a second electrode; and a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer including the compound represented by chemical formula 1 of the present invention, which can exhibit high light-emitting efficiency characteristics and life-improving characteristics.

Description

Organic electroluminescent device and organic compound for organic electroluminescent device
Technical Field
The present invention relates to an organic electroluminescent device and an organic compound used therefor, and more particularly, to an organic compound used as a light emitting layer material of an organic electroluminescent device and an organic electroluminescent device using the same.
Background
Recently, as an image display device, an organic electroluminescent display device (Organic Electroluminescence Display) has been actively developed. The organic electroluminescent display device is different from the liquid crystal display device, and as a self-luminous display device, a light-emitting material including an organic compound emits light in a light-emitting layer as holes and electrons injected from a first electrode and a second electrode are recombined in the light-emitting layer, thereby realizing display.
In the process of applying an organic electroluminescent device to a display apparatus, since low driving voltage, high luminous efficiency and long life are required for the organic electroluminescent device, there is a continuous need to develop materials for organic electroluminescent devices capable of stably realizing the same.
In particular, recently, in order to realize a high-efficiency organic electroluminescent device, a delayed fluorescence technique using phosphorescence emission of Triplet energy or using a Triplet-Triplet annihilation (TTA, triplet-Triplet annihilation) phenomenon in which singlet excitons are generated by collisions of Triplet excitons is being developed, and a thermally activated delayed fluorescence (TADF, thermally Activated Delayed Fluorescence) material using the delayed fluorescence phenomenon is being developed.
Disclosure of Invention
Technical problem
An object of the present invention is to provide an organic electroluminescent device which not only has excellent luminous efficiency but also exhibits a relatively long lifetime characteristic.
It is still another object of the present invention to provide an organic compound which is used as a material for an organic electroluminescent device and has characteristics such as high efficiency and long life.
Technical proposal
The organic compound for the organic electroluminescent device provided by the invention is represented by the following chemical formula 1:
chemical formula 1
In the above chemical formula 1, L is a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.
R 1 To R 5 Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a bond to an adjacent group to form a ring.
Ar is represented by the following chemical formula 2:
chemical formula 2
In the above chemical formula 2, Z is a direct bond (direct linkage) or O, S, NR or CR a R b R is phenyl, R a To R b Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a bond to an adjacent group to form a ring.
The above chemical formula 1 can be represented by the following chemical formula 1-1:
chemical formula 1-1
In the above chemical formula 1-1, L, Z and R 1 To R 5 The definition is the same as in chemical formula 1 and chemical formula 2.
In the above chemical formula 1, ar may be represented by one of the following Ar-1 to Ar-5:
in the above chemical formula 1, L may be represented by one of the following L-1 to L-6:
in the above L-1 to L-6, R 6 To R 10 Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl and isobutyl,
m, n, p, q and r are each independently an integer of 0 to 4.
The compound represented by the above chemical formula 1 may be a blue dopant, releasing blue light having a center wavelength of 450nm or more and less than 500 nm.
The compound represented by the above chemical formula 1 may be a green dopant that emits green light having a center wavelength of 500nm or more and 550nm or less.
The compound represented by the above chemical formula 1 may be a host material.
The absolute value (Est) of the difference between the lowest excited singlet energy level (S1) and the lowest excited triplet energy level (T1) of the compound represented by the above chemical formula 1 may be 0.2eV or less.
In still another embodiment of the present invention, an organic electroluminescent device includes: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode and containing the compound of the present invention.
The light-emitting layer includes a host and a dopant, and the host may include the compound.
The light-emitting layer emits delayed fluorescence, and the compound may be a delayed fluorescence dopant.
The light-emitting layer can emit light having a center wavelength of 500nm or more and 550nm or less or light having a center wavelength of 450nm or more and less than 500 nm.
ADVANTAGEOUS EFFECTS OF INVENTION
The organic electroluminescent device of the present invention may exhibit high efficiency and long lifetime device characteristics in a green wavelength region or a blue wavelength region.
The compound of the invention is contained in the light-emitting layer of the organic electroluminescent device, and can improve the service life characteristic of the organic electroluminescent device and realize high efficiency.
Drawings
Fig. 1 schematically illustrates a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
Fig. 2 is a cross-sectional view schematically showing an organic electroluminescent device according to still another embodiment of the present invention.
Fig. 3 is a cross-sectional view schematically showing an organic electroluminescent device according to another embodiment of the present invention.
Fig. 4 is a cross-sectional view schematically showing an organic electroluminescent device according to still another embodiment of the present invention.
Detailed Description
The present invention is susceptible to various modifications and alternative forms, and the invention will be described in detail below by way of example only with reference to the accompanying drawings. It should be understood, however, that there is no intention to limit the invention to the specific embodiments disclosed, but on the contrary, the intention is to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.
In this specification, when a certain component (or region, layer, portion, or the like) is "located on" another component, or when it is "connected" or "combined" with another component, it means that the component can be directly disposed/connected/combined with another component, or a third component is disposed between the two components.
Like reference numerals denote like structural elements. In the drawings, thicknesses, ratios, and dimensions of the constituent elements may be exaggerated to effectively explain the technical contents.
"and/or" includes all more than one combination capable of defining the relevant structure.
The terms "first", "second", and the like are used to describe various structural elements, and the above structural elements are not limited to the above terms. The above terms are used only to distinguish one structural element from other structural elements. For example, a first structural element could be termed a second structural element, and, similarly, a second structural element could be termed a first structural element, without departing from the scope of the present invention. The singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
Also, terms such as "lower", "upper", and the like are used only to describe the correlation between the structures shown in the drawings. The above terms are used as relative concepts, with reference to the orientation shown in the drawings.
In the present specification, unless defined otherwise, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Also, terms defined in a dictionary generally used should be interpreted as having the same meaning as the related art has on the text, and should not be interpreted as an idealized or excessively formalized meaning unless explicitly defined.
The terms "comprises" or "comprising" and the like are used solely to designate the presence of features, numbers, steps, operations, structural elements, components, or combinations thereof recited in the specification, and do not foreclose the presence or additional possibility of one or more other features, numbers, steps, operations, structural elements, components, or combinations thereof.
Hereinafter, an organic electroluminescent device and a compound included therein according to an embodiment of the present invention will be described with reference to the accompanying drawings.
Fig. 1 to 4 are cross-sectional views schematically showing an organic electroluminescent device according to an embodiment of the present invention. Referring to fig. 1 to 4, in an organic electroluminescent device according to an embodiment of the present invention, a first electrode EL1 and a second electrode EL2 are disposed opposite to each other, and a light emitting layer EML may be disposed between the first electrode EL1 and the second electrode EL 2.
Also, the organic electroluminescent device 10 according to an embodiment of the present invention includes a plurality of functional layers between the first electrode EL1 and the second electrode EL2 in addition to the light emitting layer EML. The plurality of functional layers may include a hole transport region HTR and an electron transport region ETR. That is, the organic electroluminescent device 10 according to an embodiment of the present invention may include a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked. Also, the organic electroluminescent device 10 according to an embodiment of the present invention may include a capping layer CPL disposed on the second electrode EL2.
In the organic electroluminescent device 10 according to an embodiment of the present invention, the light emitting layer EML disposed between the first electrode EL1 and the second electrode EL2 may include a compound according to an embodiment of the present invention described below. However, the embodiment is not limited thereto, and the organic electroluminescent device 10 according to an embodiment of the present invention may include the compound according to an embodiment of the present invention described below in the hole transport region HTR or the electron transport region ETR as a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2, in addition to the light emitting layer EML.
On the other hand, fig. 2 is a cross-sectional view of an organic electroluminescent device 10 as still another embodiment of the present invention, and compared with fig. 1, the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL.
Fig. 3 is a cross-sectional view of an organic electroluminescent device 10 according to another embodiment of the present invention, and compared to fig. 1, the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL.
Fig. 4 is a cross-sectional view of an organic electroluminescent device 10 as a further embodiment of the present invention, which includes a cover layer CPL disposed on a second electronic EL2, as compared with fig. 2.
The first electrode EL1 has conductivity. The first electrode EL1 may be made of a metal alloy or a conductive compound. The first electrode EL1 may be an anode (anode). Also, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide, for example, indium Tin Oxide (ITO), indium zinc oxide (IZO, indium zinc oxide), zinc oxide (ZnO, zinc oxide), indium tin zinc oxide (ITZO, indium tin zinc oxide), or the like. When the first electrode EL1 is a semi-transmissive electrode or a reflective electrode, the first electrode EL1 may include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride/calcium (LiF/Ca), lithium fluoride/aluminum (LiF/Al), molybdenum (Mo), titanium (Ti), or a compound or mixture thereof (e.g., a mixture of silver (Ag) and magnesium (Mg). Alternatively, a multilayer structure may be included, including a reflective film or a semi-transmissive film made of the above-described substances, and a transparent conductive film made of Indium Tin Oxide (ITO), indium zinc oxide (IZO, indium zinc oxide), zinc oxide (ZnO, zinc oxide), indium tin zinc oxide (ITZO, indium tin zinc oxide), or the like. For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. The thickness of the first electrode EL1 is about 1000 to 10000, for example, may be about 1000 to 3000.
The hole transport region HTR is formed on the first electrode EL 1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. For example, the thickness of the hole transport region HTR may be about 50 to 15000 a.
The hole transport region HTR may have a single-layer structure composed of a single substance, or a single-layer structure composed of a plurality of different substances or a multi-layer structure composed of a plurality of different substances.
For example, the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure composed of a hole injection substance and a hole transport substance. The hole transport region HTR may have a single-layer structure composed of a plurality of different substances, or may have a structure such as a hole injection layer HIL/hole transport layer HTL, a hole injection layer HIL/hole transport layer HTL/hole buffer layer (not shown), a hole injection layer HIL/hole buffer layer (not shown), a hole transport layer HTL/hole buffer layer, or a hole injection layer HIL/hole transport layer HTL/electron blocking layer EBL, which are sequentially stacked from the first electrode EL1, but the embodiment is not limited thereto.
The hole transport region HTR may be formed by various methods, for example, a vacuum evaporation method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, an inkjet printing method, a laser thermal transfer method (LITI, laser Induced Thermal Imaging), and the like.
The hole injection layer HIL may include a phthalocyanine (phthalocyanine) compound such as copper phthalocyanine (copaphthalocyanine), for example, N '- ([ 1,1' -biphenyl ] -4,4 '-diyl) bis (N-phenyl-N, N-di-m-tolylbenzene-1, 4-diamine) (DNTPD, N' - ([ 1,1'-biphenyl ] -4,4' -diyl) bis (N-phenyl-N, N-di-m-tolylzene-1, 4-diamine)), 4',4"- [ Tris (3-methylphenyl) phenylamino ] triphenylamine (m-MTDATA, 4',4" - [ 3-methylphenyl ] triphenylamine), 4',4 "-" (N, N-diphenylamino-triphenylamine (TDATA, 4'4"-Tris (N, N-diphenylamino) triphenylamine), 4',4" -Tris [ N- (2-naphthyl) -N-phenylamino ] -triphenylamine (2-TNATA, 4,4' -Tris [ N- (2-workbench) -N-phenylamino ] -triphenylamine), poly (3, 4-ethylenedioxythiophene)/Poly (4-styrenesulfonate) (PEDOT/PSS, poly (3, 4-ethylidenoxythiophene)/Poly (4-styrenesulfonate)), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphorsulfonic acid (PANI/CSA, polyaniline/Camphorsonic acid), polyaniline/Poly (4-styrenesulfonate) (PANI/PSS, polyaniline/Poly (4-styrenesulfonate)), N '-bis (naphthalen-1-yl) -N, N' -diphenyl-benzidine (NPB, -N, N '-di (naphthalen-l-yl) -N, N' -diphenyl-benzidine), polyetherketone containing Triphenylamine (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [ tetrakis (pentafluorophenyl) borate ] (4-Isopropyl-4' -methyldiphenyliodium [ Tetrakis (pentafluorophenyl) botate ]), bipyrazino [2,3-f:2',3' -h ] quinoxaline-2,3,6,7,10, 11-hexaazabenzophenanthrene (HAT-CN, dipyrazino [2,3-f:2',3' -h ] quinoxaline-2,3,6,7,10, 11-hexacarbonifile) and the like.
The hole transport layer HTL may include carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, and the like; fluorene (fluorne) derivatives; for example, N, N ' -Bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (TPD, N, N ' -Bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine), 4', triphenylamine derivatives such as 4' -tris (N-carbazolyl) triphenylamine (TCTA, 4' -tris (N-carbazolyl) triphenylamine), N, N ' -Bis (naphthalen-1-yl) -N, N ' -diphenyl-benzidine (NPB, N, N ' -di (naphthalen-1-yl) -N, N ' -diphenyl-benzodine), 4' -Cyclohexylidenebis [ N, N-Bis (4-methylphenyl) aniline ] (TAPC, 4' -cyclohexylidines [ N, N-Bis (4-methylphen) benzonamine ]), 4' -Bis [ N, N ' - (3-tolyl) amino ] -3,3' -dimethylbiphenyl (HMTPD, 4' -Bis [ N, N ' - (3-tolyl) amino ] -3,3' -dimethyllbiphenyl), 1,3-Bis (N-carbazolyl) benzene (mCP, 1,3-Bis (N-carbazolyl) benzozene), and the like.
The thickness of the hole transport region HTR may be about 50 to 10000 a, for example, may be about 100 to 5000 a. For example, the hole injection layer HIL may have a thickness of about 30 to 1000 a and the hole transport layer HTL may have a thickness of about 30 to about 1000 a. For example, the electron blocking layer EBL may have a thickness of about 10 to 1000 a. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above ranges, a satisfactory degree of hole transport characteristics can be obtained without substantially increasing the driving voltage.
In addition to the above-mentioned substances, the hole transport region HTR may further contain a charge generating substance for improving conductivity. The charge generating substance may be uniformly or non-uniformly dispersed in the hole transport region HTR. For example, the charge generating substance may be a p-dopant (dopant). The p-dopant may be one of quinone derivatives, metal oxides, and cyano (cyano) containing compounds, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7', 8' -Tetracyanoquinodimethane (F4-TCNQ, 2,3,5,6-tetrafluoro-7,7', 8' -Tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.
As described above, the hole transport region HTR may include at least one of a hole buffer layer (not shown) and an electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL. The hole buffer layer (not shown) may increase light emission efficiency by compensating for a resonance distance based on a wavelength of light emitted from the light emitting layer EML. As a substance contained in the hole buffer layer (not shown), a substance that can be contained in the hole transport region HTR can be used. The electron blocking layer EBL serves to prevent electrons from being injected from the electron transport region ETR to the hole transport region HTR.
The emission layer EML is formed on the hole transport region HTR. For example, the light emitting layer EML may have a thickness of 100 to 1000 a or 100 to 400 a. The light emitting layer EML may have a single layer structure composed of a single substance, or a single layer structure composed of a plurality of different substances or a multi-layer structure composed of a plurality of different substances.
In the organic electroluminescent device 10 according to an embodiment of the present invention, the emission layer EML may include the compound according to an embodiment of the present invention.
In the present specification, "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atom, halogen atom, cyano group, nitro group, amino group, hydroxyl group, silyl group, boron group, phosphine oxide group, phosphine sulfide group, alkyl group, halogenated alkyl group, alkoxy group, alkenyl group, aryl group, heteroaryl group and heterocyclic group. Also, each substituent exemplified above may be substituted or unsubstituted. For example, biphenyl may be interpreted as aryl, and also as phenyl substituted by phenyl.
In this specification, "bonding to an adjacent group to form a ring" may mean bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring includes aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The heterocyclic ring includes aliphatic heterocyclic ring and aromatic heterocyclic ring. The ring formed by bonding adjacent groups may be monocyclic or polycyclic. And, the ring formed by bonding can be bonded with another ring to form a screw structure.
In this specification, an "adjacent group" refers to a substituent substituted on an atom directly bonded to an atom substituted with a corresponding substituent, another substituent substituted on an atom substituted with a corresponding substituent, or a substituent most adjacent to a corresponding substituent in a steric structure. For example, in 1,2-dimethylbenzene (1, 2-dimethyllbenzene), two methyl groups may be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentene (1, 1-diethylcyclopentene), two ethyl groups may be interpreted as "adjacent groups" to each other.
In this specification, examples of the halogen atom are a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
In the present specification, the alkyl group may be a linear, branched or cyclic type. The carbon number of the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-eicosyl, N-docosanyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like, but are not limited thereto.
In the present specification, the hydrocarbon ring means an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring having 5 to 60, 5 to 30 or 5 to 20 ring-forming carbon atoms. The hydrocarbon ring group means any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of ring-forming carbon atoms of the hydrocarbon ring group may be 5 to 60, 5 to 30, or 5 to 20.
In the present specification, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms of the aryl group is 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group include phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, pentacenyl, hexabiphenyl, triphenylene, pyrenyl, perylene, benzonaphthyl, benzophenanthryl, benzofluoranthryl, and droyl, but are not limited thereto.
In the present specification, heteroaryl means any functional group or substituent derived from a ring including one or more of B, O, N, P, se, si and S as a heteroatom. The heterocyclic group includes aliphatic heterocyclic groups and aromatic heterocyclic groups. The aromatic heterocyclic group may be a heteroaryl group. Aliphatic and aromatic heterocyclic groups may be monocyclic or polycyclic.
In the present specification, a heterocyclic group means that one or more of B, O, N, P, se, si and S are included as a hetero atom. When the heterocyclic group includes two or more hetero atoms, the two or more hetero atoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including heteroaryl groups. The number of ring-forming carbon atoms of the heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.
In the present specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, se, si and S as a hetero atom. The number of ring-forming carbon atoms of the aliphatic heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include, but are not limited to, an oxirane group, an ethylthiirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a thiocyclopentanyl group, a tetrahydropyranyl group, and a 1, 4-dioxanyl group.
In the present specification, the heteroaryl group may be a heteroaryl group including at least one of O, N, P, si and S as a hetero element. According to circumstances, the N and S atoms may be oxidized and the N atom may be quaternized. The number of ring-forming carbon atoms of the heteroaryl group is 2 or more and 30 or less or 2 or more and 20 or less. Heteroaryl groups may be monocyclic heteroaryl groups or polycyclic heteroaryl groups. For example, a polycyclic heteroaryl group may have a 2-ring structure or a 3-ring structure.
Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyrazinopyrazinyl, isoquinolinyl, cinnolazinyl, indolyl, isoindolyl, indazolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, benzisothiazolyl, benzisoxazolyl, dibenzothiophenyl, benzofuranyl, pyrrolinyl, phenanthridinyl, thiazolyl, isoxazolyl, oxadiazolyl, isothiazolyl, isoxazolyl, benzothiophenyl, and dibenzofuranyl, and the like, but are not limited thereto. Examples of the N-alkylaryl group corresponding to the monocyclic heteroaryl group or the polycyclic heteroaryl group include quaternary salts such as pyridine N-alkyl groups and quinoline N-alkyl groups, but are not limited thereto.
In the present specification, the number of carbon atoms of the amine group is not particularly limited, and may be 1 to 30. Amino groups may include alkylamino groups and arylamino groups. Examples of the amine group include, but are not limited to, methylamino, dimethylamino, anilino, diphenylamino, naphthylamino, 9-methyl-anthracenamino, triphenylamino, and the like. For example, the alkyl group in the alkylamino group is the same as the above-mentioned examples of the alkyl group, and the aryl group in the arylamino group is the same as the above-mentioned examples of the aryl group.
In the present specification, a direct link (direct link) may mean a single bond.
In the present specification, "-" means a bonding position.
The light emitting layer EML of the organic electroluminescent device 10 of an embodiment of the present invention may include a compound represented by the following chemical formula 1.
Chemical formula 1
In the above chemical formula 1, L is a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.
R 1 To R 5 Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a bond to an adjacent group to form a ring.
Ar is represented by the following chemical formula 2:
chemical formula 2
In the above chemical formula 2, Z is a direct bond (direct linkage) or O, S, NR or CRaRb, R is phenyl, R a To R b Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstitutedA silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a group adjacent thereto is bonded to form a ring.
The above chemical formula 1 can be represented by the following chemical formula 1-1:
chemical formula 1-1
In the above chemical formula 1-1, L, Z and R 1 To R 5 The definition is the same as in chemical formula 1 and chemical formula 2.
In the above chemical formula 1, ar may be represented by one of the following Ar-1 to Ar-5:
in the above chemical formula 1, L may be represented by one of the following L-1 to L-6:
R 6 to R 10 Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl and isobutyl,
m, n, p, q and r are each independently an integer of 0 to 4.
The compound of an embodiment of the present invention may be one of compounds represented by the following chemical formula 3. In the organic electroluminescent device 10 according to an embodiment of the present invention, the emission layer EML may include at least one compound among the compounds represented by chemical formula 3.
Chemical formula 3
/>
/>
/>
/>
/>
/>
The compound of one embodiment of the invention can have a luminescence center wavelength (lambda) in a wavelength region of 450nm or more max ) Is a light-emitting material of (a) and (b). For example, the compound represented by chemical formula 1 in one embodiment of the present invention may be a light emitting material having a light emitting center wavelength in a wavelength region of 500nm or more and 550nm or less, or may be a light emitting material having a light emitting center wavelength in a wavelength region of 450nm or more and less than 500 nm. The compound represented by chemical formula 1 according to an embodiment of the present invention may be a green dopant or a blue dopant.
In the organic electroluminescent device 10 according to an embodiment of the present invention, the emission layer EML includes a host and a dopant, and may include the compound according to an embodiment of the present invention as a dopant. For example, in the organic electroluminescent device 10 according to an embodiment of the present invention, the emission layer EML may include a host for delayed fluorescence emission and a dopant for delayed fluorescence emission, and the compound according to an embodiment of the present invention may be included as the dopant for delayed fluorescence emission. In particular, the light emitting layer EML may include at least one of the above compounds as a thermally activated delayed fluorescence (TADF, thermally Activated Delayed Fluorescence) dopant.
The compound represented by chemical formula 1 according to an embodiment of the present invention may be a donor-acceptor (D) type delayed fluorescence dopant material. In the compound represented by chemical formula 1 according to an embodiment of the present invention, an azaborinine type (azaborinine-type) moiety corresponds to an electron acceptor, and a heterocyclic moiety represented by "Ar" may correspond to an electron donor. That is, the compound represented by chemical formula 1 according to an embodiment of the present invention may be a donor-acceptor type delayed fluorescence dopant.
The compound represented by chemical formula 1 according to an embodiment of the present invention may be used as a thermally activated delayed fluorescence dopant, and the absolute value (Est) of the difference between the lowest excited singlet energy level (S1) and the lowest excited triplet energy level (T1) is 0.2eV or less.
That is, the organic electroluminescent device 10 according to an embodiment of the present invention includes the compound according to an embodiment of the present invention as a material of the emission layer EML, which can release delayed fluorescence. For example, the light emitting layer EML may emit light to thermally activate delayed fluorescence.
The compound of the embodiment of the invention has a novel compound structure, comprises an azaborinine type part as an electron containing part, and uses a thermally activated delayed fluorescence luminescent material as a luminescent layer material of an organic electroluminescent device, so that the luminescent efficiency of the organic electroluminescent device can be improved and the service life of the organic electroluminescent device can be prolonged. In particular, the compound of an embodiment of the present invention may exhibit excellent light emitting efficiency when used as a light emitting material to emit light in a green or blue wavelength region.
In an embodiment of the present invention, the light emitting layer EML is a delayed fluorescence light emitting layer, and the light emitting layer EML may include a known host material and a compound according to an embodiment of the present invention. For example, according to an embodiment of the present invention, the light emitting layer EML includes the compound of an embodiment of the present invention as a dopant material, and may include tris (8-hydroxyquinoline) aluminum (Alq) 3 Tris (8-hydroxyquinoline) aluminum), 4'-bis (N-carbazolyl) -1,1' -biphenyl (CBP, 4'-bis (N-carbazolyl) -1,1' -biphenyl), poly (N-vinylcarbazole), 9,10-bis (naphthalen-2-yl) anthracene (ADN, 9,10-di (naphthalen-2-yl) triphenylamine, 4 '-Tris (carbazol-9-yl) -triphenylamine (TCTA, 4,4' -Tris (carbazol-9-yl) -triphenylamine), 1,3,5-Tris (1-phenyl-1H-benzo [ d ]]Imidazol-2-yl) benzene (TPBi, 1,3,5-tris (1-phenyl-1H-benzol [ d ]]imidozole-2-yl) benzene), 2-tert-butyl-9, 10-bis (naphthalen-2-yl) anthracene (TBADN, 2-tert-butyl-9,10-di (napth2-yl) anthracene), biphenylene (DSA, distyrylaryl), 4'-bis (9-carbazolyl) -2, 4' -dimethyl-biphenyl (CDBP, 4'-bis (9-carbazolyl) -2,2' -dimethyl-biphen yl), 2-Methyl-9,10-bis (naphthalen-2-yl) anthracene (MADN, 2-Methyl-9,10-bis (napthhen-2 yl) anthracene), bis [2- (diphenylphosphinyl) phenyl ] ]Ether oxide (DPEPO, bis [2- (dipheny phosphino) phenyl)]Etheroxide), hexaphenyl cyclotriphosphazene (CP 1, hexaphenyl cyclotriphosphazene), 1,4-bis (triphenylsilyl) benzene (UGH 2,1,4-Bis (triphenylsilyl) benzene), hexaphenyl cyclotrisiloxane (DPSiO) 3 Hexaphenyl cyclotriosiloxane), octaphenyl cyclotetrasiloxane (DPSiO) 4 Octaphlycyloalclotetrasiloxane), 2,8-Bis (diphenylphosphoryl) dibenzofuran (PPF, 2,8-Bis (diphenylphosphoryl) dibenzofurans), 3'-Bis (N-carbazolyl) -1,1' -biphenyl (mCBP, 3'-Bis (N-carbazolyl) -1,1' -biphen yl), 1,3-Bis (N-carbazolyl) benzene (mCP, 1,3-Bis (N-carbazolyl) benzene), and the like. However, the embodiment is not limited thereto, and may include a known delayed fluorescence light emitting host material in addition to the host material.
However, the embodiment is not limited thereto, and the compound of an embodiment of the present invention may be used as a host material of the emission layer EML. When the compound of an embodiment of the present invention is used as a host material, the light emitting layer EML may include a known dopant material in addition to the compound of an embodiment of the present invention.
In the organic electroluminescent device 10 according to an embodiment of the present invention, as a well-known dopant material, the emission layer EML may include styrene derivatives (e.g., 1,4-bis [2- (3-N-ethylcarbazolyl) vinyl ] benzene (BCzVB, 1,4-bis [2- (3-N-ethylcarbazolyl) vinyl ] benzene), 4- (di-p-tolylamino) -4'- [ (di-p-tolylamino) styryl ] stilbene (DPAVB, 4- (di-p-tolylamino) -4' - [ (di-p-tolylamino) styryl ] stillenzene), N- [4- [ (E) -2- [6- [ (E) -4- (diphenylamino) styryl ] naphthalen-2-yl ] vinyl ] phenyl ] -N-phenylaniline (N-BDAVBi, N- (4- ((E) -2- (6- ((E) -4- (diphenylamino) styryl) nanophenyl-2-yl) vinyl) phenyl) -N-phenylbenzenzenamine), perylene and derivatives thereof (e.g., 2,5,8,11-Tetra-t-butylperylene (TBP, 2,5,8, 11-Tetra-t-butylperene)), pyrene and derivatives thereof (e.g., 1-dipyrene), 1, 4-dipyrene (1, 4-dipyrene), 1,4-bis (N-dipyrene), N-Diphenylamino) pyrene (1, 4-Bis (N, N-diphenoamino) pyrene), and the like.
For example, when the light emitting layer EML emits green light, the light emitting layer EML may further include a light emitting layer containing tris (8-hydroxyquinoline) aluminum (Alq 3 Tris (8-hydroxyquinoline) aluminum). For example, when the light emitting layer EML emits green light, the light emitting layer EML includes the compound of an embodiment of the present invention as a host material, and may include fac-tris (2-phenylpyridine) iridium (Ir (ppy) as a well-known dopant material 3 A metal complex (metal complex) such as fac-tris (2-phenylpyridine) iridium, an organometallic complex (organometallic complex), oxatea ortho-ketone (coumarin), and a diffraction product thereof.
For example, when the light emitting layer EML emits blue light, the light emitting layer EML may further include a fluorescent material containing one selected from the group consisting of spiro-DPVBi (spira-DPVBi), spiro-6p (spira-6 p), distyryl-benzene (DSB), distyrylarylene (DSA), polyfluorene (PFO, polyfluorene) type polymer, and poly (p-phenylene vinylene) type polymer. For example, when the light emitting layer EML emits blue light, the light emitting layer EML includes the compound according to an embodiment of the present invention as a host material, and may include a metal complex (metal complex) such as bis (4, 6-F2 ppy) 2Irpic or an organic metal complex (organometallic complex), brilan (perlene), a diffraction thereof, and the like as a well-known dopant material.
On the other hand, although not shown, the organic electroluminescent device 10 according to an embodiment of the present invention may include a plurality of light emitting layers. The plurality of light emitting layers may be sequentially stacked, and for example, the organic electroluminescent device 10 including the plurality of light emitting layers may emit white light. The organic electroluminescent device including a plurality of light emitting layers may be a Tandem (Tandem) structure organic electroluminescent device. When the organic electroluminescent device 10 includes a plurality of light emitting layers, at least one of the light emitting layers EML may include the compound according to an embodiment of the present invention.
As shown in fig. 1 to 4, in an organic electroluminescent device 10 according to an embodiment of the present invention, an electron transport region ETR is formed on a light emitting layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiment is not limited thereto.
The electron transport region ETR may be a single layer structure composed of a single substance, or a single layer structure composed of a plurality of different substances or a multi-layer structure composed of a plurality of different substances.
For example, the electron transport region ETR may have a single-layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single-layer structure composed of an electron injection material and an electron transport material. The electron transport region ETR may have a single-layer structure composed of a plurality of different substances, or may have a structure in which an electron transport layer ETL/an electron injection layer EIL, a hole blocking layer HBL/an electron transport layer ETL/an electron injection layer EIL are stacked in this order from the light emitting layer EML, but is not limited thereto. For example, the thickness of the electron transport region ETR may be 300 to 1500 a.
The electron transport region ETR may be formed by various methods, for example, a vacuum evaporation method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, an inkjet printing method, a laser thermal transfer method (LITI, laser Induced Thermal Imaging), and the like.
When the electron transport region ETR includes the electron transport layer ETL, the electron transport region 230 may include an anthracene compound. But is not limited thereto, for example, the electron transport region may include tris (8-hydroxyquinoline) aluminum (Alq 3 Tris (8-hydroxyquinoline) aluminum), 1,3, 5-Tris [ (3-pyridyl) -benzene-3-yl]Benzene (1, 3,5-tri [ (3-pyridil) -phen-3-yl)]benzene)、2,46-tris (3 '- (pyridin-3-yl) biphenyl-3-yl) -1,3,5-triazine (2, 4,6-tris (3' - (pyridin-3-yl) biphen yl-3-yl) -1,3, 5-triazine), 2- (4- (N-phenylbenzimidazolyl-1-ylphenyl) -9,10-dinaphthyl anthracene (2- (4- (N-phenylbenzoimidazolyl-1-ylphenyl) -9,10-dinaphthyl lanthacene), 1,3, 5-tris (1-phenyl-1H-benzo [ d.)]Imidazol-2-yl) benzene (TPBi, 1,3,5-Tri (1-phenyl-1H-benzol [ d ]]imidozol-2-yl) phenyl), 2,9-Dimethyl-4, 7-Biphenyl-1, 10-phenanthroline (BCP, 2,9-Dimethyl-4,7-Diphenyl-1, 10-phenanthroline), 4,7-Diphenyl-1,10-phenanthroline (Bphen, 4,7-Diphenyl-1, 10-phenanthroline), 3- (4-Diphenyl) -4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ, 3- (4-Biphenyl) -4-phenyl-5-tert-butylphenyl-1,2, 4-triazole), 4- (Naphthalen-1-yl) -3,5-Diphenyl-4H-1,2,4-triazole, 4- (Naphtalien-1-yl) -3,5-Diphenyl-4H-1,2, 4-triazole), 2- (4-Biphenyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (tBu-PBD, 2- (4-biphen-yl) -5- (4-tert-butyl-phenyl) -1,3, 4-oxadiazole), bis (2-methyl-8-hydroxyquinoline-NI, 08) - (1, 1 '-Biphenyl-4-hydroxy) aluminum (BAlq, bis (2-methyl-8-quinolato-N1, O8) - (1, 1' -biphen-4-olato) aluminum), bis (benzoquinolin-10-hydroxy) beryllium (Bebq 2, berylium bis (benzoquinolin-10-olate), 9, 10-bis (naphthalen-2-yl) anthracene (ADN, 9,10-di (naphthalen-2-yl) anthracene), 1, 3-bis [3, 5-bis (pyridin-3-yl) phenyl ]Benzene (BmPyPhB, 1,3-Bis [3,5-di (pyridin-3-yl) phenyl)]benzene) and mixtures thereof. The electron transport layer ETL may have a thickness of about 100 to 1000 a, for example, about 150 to 500 a. When the thickness of the electron transport layer ETL satisfies the above range, a satisfactory degree of electron transport characteristics can be obtained without substantially increasing the driving voltage.
When the electron transport region ETR includes the electron injection layer EIL, the electron transport region ETR may use a halogenated metal such as LiF, naCl, csF, rbCl, rbI, a lanthanide metal such as Yb, or Li 2 O, baO, or lithium quinolinate (Liq, lithium quinolate), but is not limited thereto. The electron injection layer EIL may be composed of a material in which an electron transport material and an insulating organic metal salt (organic salt) are mixed. The organometallic salt may be one having an energy band gap (energy band gap) of about 4eV or more. As a specific example, the organometallic salt mayIncluding metal acetate, metal benzoate, metal acetoacetate (metal acetoacetate), metal acetylacetonate (metal acetylacetonate) or metal stearate. The thickness of the electron injection layer 235 is about 1 to 100 a and may be about 3 to 90 a. When the thickness of the electron injection layer EIL satisfies the above range, a satisfactory degree of electron injection characteristics can be obtained without substantially increasing the driving voltage.
As described above, the electron transport region ETR may include the hole blocking layer HBL. For example, the hole blocking layer may include at least one of 2,9-Dimethyl-4,7-Diphenyl-1,10-phenanthroline (BCP, 2,9-Dimethyl-4,7-Diphenyl-1, 10-phenanthroline) and 4,7-Diphenyl-1,10-phenanthroline (Bphen, 4,7-Diphenyl-1, 10-phenanthroline), but is not limited thereto.
The second electrode EL2 is formed on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode (cathode). The second electrode EL2 may be a transmissive electrode or a semi-transmissive electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be made of a transparent metal oxide, for example, indium Tin Oxide (ITO), indium zinc oxide (IZO, indium zinc oxide), zinc oxide (ZnO, zinc oxide), indium tin zinc oxide (ITZO, indium tin zinc oxide), or the like.
When the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 may include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride/calcium (LiF/Ca), lithium fluoride/aluminum (LiF/Al), molybdenum (Mo), titanium (Ti), or a compound or mixture thereof (e.g., a mixture of silver (Ag) and magnesium (Mg). Alternatively, a multilayer structure including a reflective film or a semi-transmissive film made of the above-described substances and a transparent conductive film made of Indium Tin Oxide (ITO), indium zinc oxide (IZO, indium zinc oxide), zinc oxide (ZnO), indium tin zinc oxide (ITZO, indium tin zinc oxide), or the like may be used.
The second electrode EL2 may be connected to an auxiliary electrode, though not shown. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.
On the other hand, the organic electroluminescent device 10 of an embodiment of the present invention further includes a capping layer CPL disposed on the second electrode EL 2. For example, the coating CPL may comprise α NPD, NPB, TPD, mMTDATA, alq 3 CuPc, N4' tetra (biphenyl 4 yl) biphenyl 4,4' diamine (TPD 15, N4', N4' -tetra (biphenyl 4 yl) biphenyl 4,4' -diamine), 4',4 "Tris (carbazolyl 9) triphenylamine (TCTA, 4',4" Tris (carbazol 9 yl) triphenylamine) and the like.
In the organic electroluminescent device 10 according to an embodiment of the present invention, the light emitting layer EML disposed between the first electrode EL1 and the second electrode EL2 includes the compound according to an embodiment of the present invention, and thus, light emitting efficiency can be improved. The compound of an embodiment of the present invention may be a thermally activated delayed fluorescence dopant, and the light emitting layer EML including the compound of an embodiment of the present invention may exhibit excellent light emitting efficiency characteristics by thermally activated delayed fluorescence light emission. In addition, the compound of the embodiment of the invention is used as a main material of the light emitting layer EML, and is used together with a known fluorescent dopant material or a known phosphorescent dopant material, so that the light emitting efficiency and the service life of the organic electroluminescent device can be improved. In particular, the compound of an embodiment of the present invention may be used as a dopant material of the emission layer EML, which may enable the organic electroluminescent device to achieve excellent emission efficiency and long lifetime characteristics in a green emission region or a blue emission region.
On the other hand, the compound of an embodiment of the present invention may be used as a material for the organic electroluminescent device 10 in an organic layer, in addition to the light emitting layer EML. For example, in the organic electroluminescent device 10 according to an embodiment of the present invention, the above-mentioned compound may also be present in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2 or the capping layer CPL disposed on the second electrode EL 2.
The compound of an embodiment of the present invention has a novel compound structure including an azaborinine type moiety as an electron acceptor, and improves the high efficiency characteristics of an organic electroluminescent device by being used as a light emitting layer material. Also, the organic electroluminescent device of an embodiment including the compound of an embodiment in the light emitting layer may exhibit high efficiency characteristics in a green light emitting wavelength region or a blue light emitting wavelength region.
Hereinafter, an organic electroluminescent device according to an embodiment of the present invention and an organic compound according to an embodiment of the present invention will be described in detail with reference to examples and comparative examples. Also, the embodiments shown below are only examples for understanding the present invention, and the scope of the present invention is not limited thereto.
Preparation example
Intermediate synthesis example 1: synthesis of intermediate (4)
(Synthesis of intermediate (1))
In a single-neck 3L flask, 105g (591.0 mmol) of N-Bromosuccinimide (N-Bromosuccinimide) was dissolved in 1.5L of acetone, 25g (148.0 mmol) of diphenylamine (diphenylamine) dissolved in 150mL of acetone was slowly added dropwise thereto, and the mixture was stirred at room temperature. After adding 1.5L of ice water and stirring for 1 hour, the resultant solid was filtered. The dried solid was refluxed in a small amount of toluene (tolue) for 1 hour. After cooling to room temperature, the resultant solid was filtered to obtain 29.0g (yield: 40.0%) of a white solid compound (intermediate (1)).
(Synthesis of intermediate (2))
29.0g (59.8 mmol) of intermediate (1), 1.9g (5.9 mmol) of tetrabutylammonium bromide (Tetrabutylammonium bromide), 18.4g (328 mmol) of potassium hydroxide (Potassium hydroxide) and 397mL of THF were added to a single-neck 1L flask and stirred under reflux. After 4 hours, the mixture was cooled to room temperature, and 7.3g (89.7 mmol) of chloromethyl methyl ether (MOM-Cl, chloromethyl methyl ether) was added dropwise thereto, followed by stirring at room temperature. After the reaction was completed, it was extracted with distilled water and Dichloromethane (DCM). With anhydrous sodium sulfate (Na 2 SO 4 ) After the separated organic layer was dried, the solvent was removed by reduced pressure. The reaction was solidified with methanol (MeOH) to obtain 30.2g (yield: 95.5%) of a white solid compound (intermediate (2)) 。
(Synthesis of intermediate (3))
In a three-necked 2L flask, 34.1g (64.5 mmol) of the intermediate (2) was dissolved in 645mL of diethyl ether (diethyl ether), and then cooled to-78 ℃. 57mL (142 mmol) of n-butyllithium (n-BuLi, 2.5M in Hexanes) were slowly added dropwise. After stirring at the same temperature for 1 hour, 13.6g (70.9 mmol) of dimethyl borate (dimethyl mesitylboronate) was slowly added dropwise. Gradually raising the temperature to normal temperature and stirring. After completion of the reaction with distilled water, anhydrous sodium sulfate (Na 2 SO 4 ) After the separated organic layer was dried, the solvent was removed by reduced pressure. The reaction was solidified with methanol (MeOH) to obtain 22.0g (yield: 68.8%) of a pale yellow solid compound (intermediate (3)).
(Synthesis of intermediate (4))
22.0g (44.1 mmol) of intermediate (3) was dissolved in 645mL of THF in a three-necked 2L flask, and cooled to-78 ℃. 38.8mL (96.9 mmol) of n-butyllithium (n-BuLi, 2.5M in hexane (2.5M in Hexanes)) was slowly added dropwise. After stirring for 1 hour at the same temperature, ammonium chloride (NH) saturated at-78℃was used 4 Cl) aqueous solution ended the reaction. With distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the separated organic layer was dried, the solvent was removed by reduced pressure. After the reaction was dissolved in 220mL of diethyl ether (diethyl ether), 7.4mL of Conc.HCl was slowly added dropwise and stirred at room temperature. After the reaction was completed, the mixture was treated with saturated sodium carbonate (Na 2 CO 3 ) The aqueous solution is neutralized. With distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 3.0g (yield: 23.1%) of the compound (intermediate (4)) as a yellow solid.
Intermediate synthesis example 2: synthesis of intermediate (5)
In a single-neck 1L flask, 20.0g (109 mmol) of 10H-phenoxazine (10H-phenoxazine), 37.1g (131 mmol) of 1-bromo-4-iodobenzene (1-bromoo-4-iodobenzene), 0.45g (2.2 mmol) of CuI, 1.2g (10.9 mmol) of 1,2-diaminocyclohexane (1, 2-diaminocyclohexane), 21.0g (218 mmol) of NaOtBu and 545mL of Dioxane (Dioxane) were mixed and refluxed. After the reaction was completed, it was cooled to room temperature and extracted with distilled water and DCM. With anhydrous sodium sulfate (Na 2 SO 4 ) After the separated organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 10.8g (yield: 29.2%) of the compound as a white solid (intermediate (5)).
Intermediate synthesis example 3: synthesis of intermediate (6)
In a single port 100mL flask, 10.0g (17.8 mmol) of 9,9-dimethyl-9,10-dihydroacridine (9, 9-dimethyl-9, 10-dihydroacridine), 14.9g (52.6 mmol) of 1-bromo-4-iodobenzene (1-bromoo-4-iodobenzene), 0.46g (2.3 mmol) of CuI, 0.5g (4.780 mmol) of 1,2-diaminocyclohexane (1, 2-diaminocyclohexane), 9.2g (95.6 mmol) of NaOtBu and 240mL of Dioxane were mixed and refluxed. After the completion of the reaction, distilled water and DCM were added thereto at room temperature to extract, followed by extraction with anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 11.2g (yield: 63.0%) of the compound as a white solid (intermediate (6)).
Intermediate synthesis example 4: synthesis of intermediate (7)
In a single port 100mL flask, 10.0g (33.6 mmol) of intermediate (4), 8.0g (33.6 mmol) of 2,5-Dibromopyridine (2, 5-Dibronoperidine), 1.9g (3.4 mmol) of P were mixedd(dba) 2 2.7g (6.7 mmol) of 50% P (tBu) 3 After 6.5g (67.3 mmol) of NaOtBu and 100mL of Dioxane (Dioxane) were refluxed. After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 5.1g (yield: 33.5%) of the compound as a white solid (intermediate (7)).
Intermediate synthesis example 5: synthesis of intermediate (8)
In a single-neck 500mL flask, 10.0g (59.8 mmol) of Carbazole, 34.2g (119.6 mmol) of 2,6-Dibromonaphthalene (2, 6-Dibromonaphthalene), 1.1g (6.0 mmol) of CuI, 1.4g (12.0 mmol) of 1, 2-diaminocyclohexane (1, 2-diaminocyclohexane), 5.7g (119.6 mmol) of NaOtBu and 300mL of Dioxane (Dioxane) were mixed and refluxed. After the completion of the reaction, distilled water and DCM were added thereto at room temperature to extract the mixture, followed by extraction with anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 11.2g (yield: 50.3%) of the compound (intermediate (8)) as a white solid.
Intermediate synthesis example 6: synthesis of intermediate (11)
(Synthesis of intermediate (9))
In a single port 500mL flask, 10.0g (31.0 mmol) of 9- (4-bromophenyl) -9H-carbazole (9- (4-bromobenzyl) -9H-carbazole), 9.5g (37.2 mmol) of bis (pinacolato) diboron (Bis (pinacolato) diboron), 1.3g (1.6 mmol) of Pd (dppf) Cl were mixed 2 -CH 2 Cl 2 After 6.1g (62.1 mmol) of KOAc and 150mL of 1, 4-dioxane, the mixture was stirred at a temperature of 100℃for 12 hoursWhen (1). After the reaction was completed, it was cooled to room temperature and concentrated under reduced pressure through a celite pad. By column chromatography on silica gel (CHCl) 3 ) The reaction mixture was purified to obtain 9.2g (yield: 80.3%) of a white solid compound (intermediate (9)).
(Synthesis of intermediate (10))
9.2g (24.9 mmol) of 6-bromonaphthalen-2-ol (6-bromonapthalen-2-ol), 5.6g (24.9 mmol) of intermediate (9), 1.4g (1.3 mmol) of Pd (PPh) are mixed 3 ) 4 10.6g (49.8 mmol) of K 3 PO 4 100mL of toluene, 30mL of ethanol and 30mL of water were refluxed and stirred for 12 hours. After the completion of the reaction, the mixture was cooled to room temperature, water was added thereto, and after extraction with ethyl acetate, the solvent was removed under reduced pressure. By column chromatography on silica gel (CHCl) 3 ) The obtained reaction mixture was purified and solidified with a mixed solution (DCM/Hex) to obtain 7.2g (yield: 74.9%) of a white solid compound (intermediate (10)).
(Synthesis of intermediate (11))
7.2g (18.7 mmol) of intermediate (10) was dissolved in 95mL of Dichloromethane (DCM), and after dropwise addition of 4.4g (56.0 mmol) of Pyridine (Pyridine), the temperature was lowered to 0 ℃. 6.3g (22.4 mmol) of Tf were slowly added dropwise 2 After O, the temperature was raised to room temperature and reacted for 12 hours. After washing the reaction with water (100 mL), the separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, followed by column chromatography (CHCl 3 ) Purification was performed to obtain 8.2g (yield: 84.8%) of a yellow solid compound (intermediate (11)).
The intermediate compounds synthesized as described above were used to synthesize a variety of organic compounds as follows.
Synthesis example 1: synthesis of Compound 3-11 (LT 18-30-529)
In a single port 100mL flask, 1.5g (5.0 mmol) of intermediate (4), 1.5g (4.6 mmol) of intermediate (5), 0.3g (0.5 mmol) of Pd (dba) were mixed 2 0.4g (0.9 mmol) of 50% P (tBu) 3 1.3g (13.8 mmol) NaOtBu and 23mL Toluene (tolene). After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to give 0.9g (yield: 33.0%) of compound 3-11 (LT 18-30-529) as a white solid.
Synthesis example 2: synthesis of Compound 3-13 (LT 18-30-541)
In a single port 100mL flask, 1.5g (5.0 mmol) of intermediate (4), 2.7g (7.6 mmol) of intermediate (6), 0.3g (0.5 mmol) of Pd (dba) were mixed 2 0.4g (1.0 mmol) of 50% P (tBu) 3 1.4g (15.2 mmol) NaOtBu and 26mL Toluene (tolene). After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to obtain 0.7g (yield: 25.0%) of compound 3-13 (LT 18-30-541) as a white solid.
Synthesis example 3: synthesis of Compound 3-15 (LT 18-30-543)
In a single port 100mL flask, 1.5g (5.0 mmol) of intermediate (4), 2.4g (7.6 mmol) of 9- (4-bromophenyl) -9H-carbazole, 0.3g (0.5 mmol) of Pd (dba) were mixed 2 0.4g (1.0 mmol) of 50% P (tBu) 3 1.4g (15.2 mmol) NaOtBu and 26mL Toluene (tolene). After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. By passing throughThe reaction was purified by silica gel column chromatography (Hex: DCM) to give 0.7g (yield: 26.1%) of compound 3-15 (LT 18-30-543) as a white solid.
Synthesis example 4: synthesis of Compound 3-80 (LT 19-35-205)
In a single port 100mL flask, 2.0g (6.7 mmol) of intermediate (4), 3.5g (6.7 mmol) of intermediate (11), 0.4g (0.7 mmol) of Pd (dba) were mixed 2 0.5g (1.4 mmol) of 50% P (tBu) 3 1.3g (13.5 mmol) NaOtBu and 23mL Toluene (tolene). After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to give 1.5g (yield: 33.5%) of compound 3-80 (LT 19-35-205) as a white solid.
Synthesis example 5: synthesis of Compound 3-87 (LT 19-35-209)
1.0g (5.0 mmol) of 10H-phenothiazine (10H-phenothiazine), 2.3g (5.0 mmol) of intermediate (7), 0.1g (0.5 mmol) of CuI, 0.1g (1.0 mmol) of 1,2-diaminocyclohexane (1, 2-diaminocyclohexane), 1.0g (10.0 mmol) of NaOtBu and 25mL of Dioxane were mixed and refluxed. After the reaction was completed, cooled to room temperature and extracted with distilled water and DCM. With anhydrous sodium sulfate (Na 2 SO 4 ) After the separated organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to give 1.2g (yield: 41.8%) of compound 3-87 (LT 19-35-209) as a white solid.
Synthesis example 6: synthesis of Compound 3-100 (LT 19-35-213)
In a single port 100mL flask, 2.0g (6.7 mmol) of intermediate (4), 2.5g (6.7 mmol) of intermediate (11), 0.4g (0.7 mmol) of Pd (dba) were mixed 2 0.5g (1.4 mmol) of 50% P (tBu) 3 1.3g (13.5 mmol) NaOtBu and 23mL Toluene (tolene). After the reaction was completed, distilled water and chloroform (CHCl) 3 ) And (5) extracting. With anhydrous sodium sulfate (Na 2 SO 4 ) After the organic layer was dried, the solvent was removed by reduced pressure. The reaction was purified by silica gel column chromatography (Hex: DCM) to give 1.1g (yield: 27.8%) of compound 3-100 (LT 19-35-213) as a white solid.
Test examples
1. Evaluation of Compounds
Fluorescence emission characteristics were evaluated for the compounds of one embodiment of the present invention. The compound of one embodiment of the present invention was evaluated together with the light-emitting characteristics of the compound of the comparative example. The compounds used for the evaluation are shown below.
(Compound for evaluation of luminescence characteristics)
(comparative example Compound for evaluation of luminescence Properties)
Table 1 shows the ΔE of the compound of one example of the present invention and the compound of the comparative example ST Value and emission wavelength. E (E) ST Corresponds to the difference between the lowest excited singlet energy level (S1 level) and the lowest excited triplet energy level (T1 level), calculated by Gaussian (Gaussian) calculation. The emission wavelengths of the example compounds and the comparative example compounds were confirmed by the emission spectrum.
TABLE 1
/>
Referring to the results of table 1, the compound of an embodiment of the present invention may be used as a light emitting material that emits blue light or green light. Also, the compounds of one embodiment of the invention have a ΔE of less than 0.20eV ST The value can be used as a delayed fluorescence luminescent material.
Examples
Preparation and evaluation of organic electroluminescent device
(preparation example of organic electroluminescent device comprising the Compound according to an embodiment of the invention)
The organic electroluminescent device according to an embodiment of the present invention, using the compound according to an embodiment of the present invention as a dopant material for a light emitting layer, is prepared by the following method.
(preparation of organic electroluminescent device)
After the glass substrate with the ITO pattern was washed with ultrapure water and cleaned by ultrasonic waves, ultraviolet rays were irradiated for 30 minutes and ozone treatment was performed. Next, a hole transport region was formed by vapor deposition of HT1 at a thickness of 1200 a and vapor deposition of HT2 at a thickness of 100 a.
Subsequently, in the process of forming the light emitting layer, at 20:80 or a compound of one embodiment of the present invention or a compound of a comparative example and mCBP were co-evaporated to form a layer with a thickness of 400 a. That is, the light-emitting layer formed by co-evaporation was formed by mixed evaporation of the compound of each example and mCBP in examples, and by mixed evaporation of the compound of the comparative example and mCBP in comparative examples.
Then, ET and Liq were combined at 5:5 to form a layer having a thickness of 300 a on the light-emitting layer, and forming a layer having a thickness of 10 a with Liq to form an electron transport region. Then, mg: ag (10:1) forms a second electrode with a thickness of 100 a.
In an embodiment, the hole transport region, the light emitting layer, the electron transport region, and the second electrode may be formed using a vacuum evaporation device.
The hole transport region material, the electron transport region material, and the dopant material used for preparing the organic electroluminescent device are shown below.
Also, the compounds used in examples 1 to 1 are shown below.
(evaluation of characteristics of organic electroluminescent device)
Table 2 shows the efficiency, lifetime and emission color of the prepared organic electroluminescent device by comparison. In the results of evaluating the characteristics of the examples and comparative examples shown in Table 2, the efficiency indicates that the current density was 10mA/cm 2 Is provided. In the characteristic evaluation of the organic electroluminescent device, the efficiency and lifetime of the comparative example were set to 100% with respect to those of the examples.
TABLE 2
Referring to the results of table 2, examples are organic electroluminescent devices that emit blue light, and the compounds of the present invention may be used as blue dopants that emit blue light.
Also, referring to the results of table 2, the devices of examples 1 to 6 may exhibit more excellent efficiency characteristics and lifetime characteristics than the devices of the comparative examples.
Thus, referring to the evaluation results of table 2, it was confirmed that the compound of the present invention was used as a light emitting layer dopant material of an organic electroluminescent device to release blue light. Also, the compound of the present invention contains an aza-type benzoxazole moiety as compared to the compound of the comparative example, and thus, when used as a dopant material for a light emitting layer, can effectively improve the efficiency and lifetime characteristics of an organic electroluminescent device.
The compound of the present invention has a novel compound structure including an azaborinine type moiety as an electron acceptor, and is used as a light emitting layer material to improve the high efficiency and long life characteristics of an organic electroluminescent device. Also, an organic electroluminescent device including the compound of the present invention in a light emitting layer may exhibit high efficiency characteristics and improved lifetime characteristics in a green light emitting wavelength region or a blue light emitting wavelength region.
While the invention has been described above with reference to the preferred embodiments, it should be understood that various modifications and changes can be made by one of ordinary skill in the art to which the invention pertains or by one of ordinary skill in the art without departing from the spirit and scope of the invention as set forth in the claims below.
Therefore, the technical scope of the present invention is not limited to the details described in the specification, and should be defined based on the scope of the invention claimed.
Industrial applicability
The organic compound of the present invention is used for a functional layer disposed between a first electrode and a second electrode of an organic electroluminescent device, and in particular, can improve the quality of the organic electroluminescent device by being used for a light emitting layer.
When the above organic compound is used for a light emitting layer of an organic electroluminescent device, the organic electroluminescent device can express not only original characteristics but also high efficiency characteristics and improved lifetime characteristics in a green light emitting wavelength region or a blue light emitting wavelength region based on the characteristics of the above organic compound.

Claims (12)

1. An organic compound for an organic electroluminescent device, characterized by being represented by the following chemical formula 1:
Chemical formula 1
In the above-mentioned chemical formula 1,
l is a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms,
R 1 to R 5 Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a bond to an adjacent group to form a ring,
ar is represented by the following chemical formula 2:
chemical formula 2
In the above-mentioned chemical formula 2,
z is a direct bond or O, S, NR or CR a R b ，
R is a phenyl group, and is a phenyl group,
R a to R b Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or a bond to an adjacent group to form a ring.
2. The organic compound for an organic electroluminescent device according to claim 1, wherein the chemical formula 2 is represented by one of the following chemical formulas 2-1:
chemical formula 2-1
。
3. The organic compound for an organic electroluminescent element as claimed in claim 1, wherein the above L is represented by one of the following L-1 to L-6:
R 6 to R 10 Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl and isobutyl,
m, n, p, q and r are each independently an integer of 0 to 4.
4. The organic compound for an organic electroluminescent element according to claim 1, wherein the compound represented by chemical formula 1 is a blue dopant, and emits blue light having a center wavelength of 450nm or more and less than 500 nm.
5. The organic compound for an organic electroluminescent element according to claim 1, wherein the compound represented by chemical formula 1 is a green dopant, and emits green light having a center wavelength of 500nm or more and 550nm or less.
6. The organic compound for an organic electroluminescent element according to claim 1, wherein the compound represented by chemical formula 1 is a host material.
7. The organic compound for an organic electroluminescent element according to claim 1, wherein an absolute value Δest of a difference between a lowest excited singlet energy level S1 and a lowest excited triplet energy level T1 of the compound represented by chemical formula 1 is 0.2eV or less.
8. The organic compound for an organic electroluminescent element according to claim 1, wherein the compound represented by chemical formula 1 is one of compounds represented by chemical formula 3:
chemical formula 3
9. An organic electroluminescent device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
and a light-emitting layer disposed between the first electrode and the second electrode and containing a compound represented by chemical formula 1.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host and a dopant, and the host comprises the compound.
11. The device of claim 9, wherein the light-emitting layer emits delayed fluorescence and the compound is a delayed fluorescence dopant.
12. The organic electroluminescent device according to claim 9, wherein the light-emitting layer emits light having a center wavelength of 500nm or more and 550nm or less or light having a center wavelength of 450nm or more and less than 500 nm.
CN202280009412.4A 2021-01-22 2022-01-06 Organic electroluminescent device and organic compound for organic electroluminescent device Pending CN116724685A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2021-0009037 2021-01-22
KR1020210009037A KR102279134B1 (en) 2021-01-22 2021-01-22 Organic electroluminescence device and organic compound for organic electroluminescence device
PCT/KR2022/000200 WO2022158762A1 (en) 2021-01-22 2022-01-06 Organic electroluminescent device and organic compound for organic electroluminescent device

Publications (1)

Publication Number Publication Date
CN116724685A true CN116724685A (en) 2023-09-08

Family

ID=77125766

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202280009412.4A Pending CN116724685A (en) 2021-01-22 2022-01-06 Organic electroluminescent device and organic compound for organic electroluminescent device

Country Status (3)

Country Link
KR (1) KR102279134B1 (en)
CN (1) CN116724685A (en)
WO (1) WO2022158762A1 (en)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5935199B2 (en) 1976-03-23 1984-08-27 富士産業株式会社 Mounting device for electronic components with leads on printed wiring boards
JP4428772B2 (en) * 1999-09-28 2010-03-10 コニカミノルタホールディングス株式会社 Organic electroluminescence device
US9073948B2 (en) * 2010-05-14 2015-07-07 Universal Display Corporation Azaborine compounds as host materials and dopants for PHOLEDs
KR20180007727A (en) 2016-07-13 2018-01-24 삼성디스플레이 주식회사 Polycyclic compound and organic electroluminescence device including the same
CN109134520B (en) * 2018-09-30 2021-08-03 上海天马有机发光显示技术有限公司 Thermal activation delay material and organic photoelectric device comprising same
KR20200094262A (en) * 2019-01-29 2020-08-07 삼성디스플레이 주식회사 Organic electroluminescence device and polycyclic compound for organic electroluminescence device
CN111574543A (en) * 2019-02-18 2020-08-25 江苏三月科技股份有限公司 Organic compound containing boron and application thereof in organic electroluminescent device

Also Published As

Publication number Publication date
WO2022158762A1 (en) 2022-07-28
KR102279134B1 (en) 2021-07-19

Similar Documents

Publication Publication Date Title
TWI753961B (en) Monoamine compound
JP7390105B2 (en) Organic electroluminescent devices and monoamine compounds for organic electroluminescent devices
JP7479134B2 (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN109305950B (en) Light absorber and organic electroluminescent device including the same
US11980091B2 (en) Organic electroluminescence device and compound for organic electroluminescence device
CN113690395A (en) Organic electroluminescent device
CN112574241A (en) Light emitting device and polycyclic compound for light emitting device
JP2021057582A (en) Organic electroluminescent element and polycyclic compound for organic electroluminescent element
CN113196511A (en) Organic electroluminescent device and spiro compound for organic electroluminescent device
JP2023100702A (en) Organic electroluminescent element, and amine compound for organic electroluminescent element
JP2021054811A (en) Organic electroluminescence device and compound for organic electroluminescence device
CN112652724A (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
JP2023123511A (en) Nitrogen-containing compound and organic el device including the same
CN110551131A (en) Organic electroluminescent device and condensed cyclic compound for organic electroluminescent device
CN111269188B (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN112038504A (en) Organic electroluminescent device
CN112151684A (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN109553634B (en) Silicon-containing compound and organic electroluminescent device comprising the same
CN111196780A (en) Organic electroluminescent device and compound for organic electroluminescent device
JP7446793B2 (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN110016055B (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN112786818A (en) Organic electroluminescent device and polycyclic compound for organic electroluminescent device
CN113161505A (en) Organic electroluminescent device and nitrogen-containing compound for organic electroluminescent device
CN112117385A (en) Organic electroluminescent device and compound for organic electroluminescent device
CN112397662A (en) Organic electroluminescent device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination