CN115894462B - Organic compound, organic electroluminescent device and electronic apparatus - Google Patents

Organic compound, organic electroluminescent device and electronic apparatus Download PDF

Info

Publication number
CN115894462B
CN115894462B CN202211226723.4A CN202211226723A CN115894462B CN 115894462 B CN115894462 B CN 115894462B CN 202211226723 A CN202211226723 A CN 202211226723A CN 115894462 B CN115894462 B CN 115894462B
Authority
CN
China
Prior art keywords
present application
organic
compound
group
carbon atoms
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.)
Active
Application number
CN202211226723.4A
Other languages
Chinese (zh)
Other versions
CN115894462A (en
Inventor
马天天
杨雷
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.)
Beijing Laite Zhongcheng Photoelectric Material Technology Co ltd
Original Assignee
Beijing Laite Zhongcheng Photoelectric Material Technology 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 Beijing Laite Zhongcheng Photoelectric Material Technology Co ltd filed Critical Beijing Laite Zhongcheng Photoelectric Material Technology Co ltd
Priority to CN202211226723.4A priority Critical patent/CN115894462B/en
Publication of CN115894462A publication Critical patent/CN115894462A/en
Priority to PCT/CN2023/120210 priority patent/WO2024078287A1/en
Application granted granted Critical
Publication of CN115894462B publication Critical patent/CN115894462B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescence device using the same and an electronic device.

Description

Organic compound, organic electroluminescent device and electronic apparatus
Technical Field
The present application relates to the technical field of organic electroluminescence, and in particular, to an organic compound, and an organic electroluminescent device and an electronic device using the same.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
Currently, for organic electroluminescent devices, the luminescent material plays an important role in the device efficiency of the OLED. The light-emitting layer material may be a host material or a guest material. And the organic luminescent layer of the organic electroluminescent device is used as a combination of a main body and a doping agent, thereby improving color purity, luminous efficiency and stability. However, when such a dopant/host material combination is used as an organic light emitting layer, the host material has a great influence on the efficiency and lifetime of the organic electroluminescent device, and thus, there is a continuous need to develop a novel host material for an organic electroluminescent device, which has high efficiency and long lifetime, and is suitable for mass production.
It should be noted that the information disclosed in the foregoing background section is only for enhancing understanding of the background of the present application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The object of the present application is to provide an organic compound, and an organic electroluminescent device and an electronic apparatus using the same, which have high luminous efficiency and service life.
In order to achieve the above object, a first aspect of the present application provides an organic compound having a structure represented by the following formula 1:
wherein Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
x is selected from C (R) 1 R 2 ) O, S or N (R) 3 )；
R 1 And R is 2 The two groups are the same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, aryl with 6-12 carbon atoms, halogenated aryl with 6-12 carbon atoms and deuterated aryl with 6-12 carbon atoms;
R 3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
the Ar and R are 3 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-12 carbon atoms or deuterated aryl group with 6-12 carbon atoms.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
Preferably, the functional layer includes an organic light emitting layer including the organic compound;
preferably, the organic electroluminescent device is a green organic electroluminescent device
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
The organic compound is a compound of which 3, 3-bicarbazole is combined with a dibenzofive-membered ring group, and the carbazole ring connected with the dibenzofive-membered ring is required to be subjected to total deuteration. The organic compound has good hole mobility and high first triplet state energy level; particularly, the carbazole group connected with the dibenzo five-membered ring in the structure is the part with higher spin density, namely more concentrated exciton energy, and the carbazole group is completely deuterated, so that the photoelectric stability of molecules can be effectively improved; meanwhile, the other carbazole is kept from deuteration, so that the symmetry of a molecular core structure can be effectively reduced, the molecular crystallinity is reduced, and the film forming capability of the material is improved. When the organic compound is used as a light-emitting layer main body in the organic electroluminescent device, the service life of the device can be remarkably prolonged while the low driving voltage and the high light-emitting efficiency are maintained.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
320. Hole transport layer 330, hole auxiliary layer 340, organic light emitting layer 350, electron transport layer
360. Electron injection layer 400 and electronic device
Detailed Description
In view of the foregoing problems of the prior art, it is an object of the present invention to provide an organic compound, which can improve the performance of an organic electroluminescent device and an electronic apparatus, for example, reduce the driving voltage of the device, and increase the efficiency and lifetime of the device, and an organic electroluminescent device and an electronic apparatus including the same.
According to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
wherein Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
x is selected from C (R) 1 R 2 ) O, S or N (R) 3 )；
R 1 And R is 2 The two groups are the same or different and are respectively and independently selected from alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, aryl with 6-12 carbon atoms, halogenated aryl with 6-12 carbon atoms and deuterated aryl with 6-12 carbon atoms;
R 3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
the Ar and R are 3 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, halogenated alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-12 carbon atoms or deuterated aryl group with 6-12 carbon atoms.
In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently" are interchangeable, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. Example(s)As an example of the presence of a metal such as,wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, cyano, halogen, alkyl, haloalkyl, deuterated alkyl, phenyl, deuterated aryl, halogenated aryl, cycloalkyl, etc. The number of substitutions may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3,4, 5, 6, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, spirobifluorenyl radicals, and the like. As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, terphenyl includes
In the present application, the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, for example, a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, or 20. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 20 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms.
In the present application, the fluorenyl group may be substituted with 1 or 2 substituents, wherein, in the case where the above fluorenyl group is substituted, it may be:and the like, but is not limited thereto.
In the present application, aryl groups as substituents for Ar are, for example, but not limited to, phenyl and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
Specific examples of deuterated alkyl groups herein include, but are not limited to, tridentate methyl.
In the present application, specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl groups.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3,4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
In some embodiments of the present application, the organic compound is selected from the group consisting of compounds represented by formulas 1-1, 1-2, 1-3, and 1-4:
in some embodiments of the present application, the organic compound is selected from the group consisting of compounds represented by formula 2-1-A, formula 2-1-B, formula 2-1-C, formula 2-1-D, formula 2-1-E, formula 2-1-F, formula 2-1-G, formula 2-1-H, formula 2-1-L, formula 2-1-M, formula 2-1-N, formula 2-1-P, formula 2-1-R, formula 2-1-U, formula 2-1-V:
in some embodiments of the present application, ar is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.
Optionally, the substituents in Ar are the same or different and are respectively and independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.
In other embodiments of the present application, ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or unsubstituted biphenyl.
Alternatively, the substituents in Ar are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
In some embodiments of the present application, ar is selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more than two substituents, each substituent is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and pentadeuterated phenyl, and when the number of substituents on the group V is more than 1, the substituents are the same or different.
Optionally, ar is selected from the group consisting of:
specifically, ar is selected from the group consisting of:
in some embodiments of the present application, R 3 Is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
Optionally, the R 3 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, phenyl group or pentadeuterated phenyl group.
In some embodiments of the present application, R 3 Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted biphenyl.
Alternatively, R 3 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, phenyl or pentadeuterated phenyl.
In some embodiments of the present application, R 3 Selected from the group consisting of:
specifically, R 3 Selected from the group consisting of:
further alternatively, R 3 Is phenyl.
In some embodiments of the present application, R 1 And R is 2 Are all methyl groups.
In some embodiments of the present application, the organic compound is selected from the group consisting of:
/>
/>
according to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound of the present application.
Optionally, the functional layer comprises an organic light emitting layer.
Further alternatively, the organic light emitting layer comprises an organic compound of the present application.
In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.
In some embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.
In some embodiments of the present application, the organic electroluminescent device comprises an anode (ITO substrate), a hole transport layer, a hole assist layer, an organic light emitting layer, an electron transport layer, an electron injection layer, a cathode (mg—ag mixture), and an organic capping layer in that order.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200 disposed opposite to the anode 100, and at least one organic layer 300 interposed between the anode layer and the cathode layer, the organic layer 300 including a hole injection layer 310, a hole transport layer 320, a hole auxiliary layer 330, an organic light emitting layer 340, an electron transport layer 350, and an electron injection layer 360, which are sequentially stacked.
Alternatively, the anode 100 includes an anode material, which is preferably a material having a large work function that facilitates hole injection into the organic layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. In one specific embodiment of the present application, the anode is an ITO substrate.
Alternatively, the hole transport layer 320 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in some embodiments of the present application, hole transport layer 320 is comprised of HT-24.
Alternatively, the hole auxiliary layer 330 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in some embodiments of the present application, hole assist layer 330 is comprised of HT-20.
Optionally, a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in one embodiment of the present application, hole injection layer 310 is comprised of PD and HT-24.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 340 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 340 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 340 may be a hybrid host material, wherein the hybrid host material includes a hole type host material and an electron type host material. The electron-type host material may be a triazine-based material, a quinoline-based material, or the like, which is not particularly limited in this application.
In one embodiment of the present application, the electron-type host material (N-type) of the organic light-emitting layer is H45
In one specific embodiment of the present application, the hole-type host material (P-type) of the organic light-emitting layer is an organic compound of the present application.
The guest material (DOPANT) of the organic light emitting layer 340 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. For example, specific examples of the green phosphorescent dopant include, but are not limited to,
in one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device, the host material of the organic electroluminescent layer 340 is the organic compound and H45 of the present application, and the guest material (DOPANT) is PD-1.
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application. For example, in some embodiments of the present application, electron transport layer 350 may be composed of ET-01 and LiQ. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:
in one embodiment of the present application, electron transport layer 350 may be composed of ET-01 and LiQ.
Alternatively, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. A metal electrode including silver and magnesium is preferable as the cathode.
Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In some embodiments of the present application, the electron injection layer 360 may include LiQ.
The application also provides an electronic device comprising the organic electroluminescent device.
For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, where the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, the first electronic device has the same beneficial effects, and the description thereof is omitted herein.
The present application will be described in detail below in connection with examples, but the following description is intended to explain the present application and is not intended to limit the scope of the present application in any way.
Synthesis of intermediate a 1:
n-phenyl-3-carbazoleboronic acid (10.0 g;34.8 mmol), 3-bromocarbazole-D7 (8.8 g;34.8 mmol), tetrakis triphenylphosphine palladium (0.8 g; 0.7 mmol), potassium carbonate (9.6 g;69.7 mmol), tetrabutylammonium bromide (2.2 g;7.0 mmol), toluene (80 mL), ethanol (20 mL) and deionized water (20 mL) were added to a nitrogen-protected round-bottomed flask, and the mixture was heated to 75℃to 80℃and reacted with stirring for 24 hours; cooling the reaction solution to room temperature, filtering, leaching the obtained solid by using water and ethanol, and drying to obtain a crude product; the crude product was purified by recrystallization from toluene to give intermediate a1 (10.6 g; yield: 73%) as a pale gray solid.
Referring to the synthesis of intermediate a1, the following intermediate shown in table 1 was synthesized with reactant a instead of N-phenyl-3-carbazoleboronic acid:
TABLE 1
Synthesis of compound A1:
/>
intermediate a1 (5.0 g;12.0 mmol), 3-bromodibenzofuran (3.1 g;12.6 mmol), tris (dibenzylideneacetone) dipalladium (0.1 g; 0.1 mmol), tri-tert-butylphosphine (0.05 g;0.2 mmol), sodium tert-butoxide (1.7 g;18.0 mmol) and xylene (50 mL) were added to a round-bottomed flask and reacted under nitrogen at 135℃to 140℃for 12 hours with stirring; stopping the reaction, cooling to room temperature, separating the reaction liquid after deionized water washing, drying the organic phase by anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using toluene as an eluent, followed by recrystallization purification using toluene/n-heptane as a solvent to give Compound A1 (5.1 g; yield: 73%) as a white solid.
Referring to the synthesis of compound A1, the following compounds in table 2 were synthesized with reactant C instead of intermediate A1 and reactant B instead of 3-bromodibenzofuran:
TABLE 2
/>
/>
/>
/>
The partial compound spectrum data is shown in Table 3 below
TABLE 3 Table 3
Compound A1 m/z＝582.3(M+H) + Compound C1 m/z＝598.3(M+H) +
Compound A3 m/z＝658.3(M+H) + Compound C4 m/z＝674.3(M+H) +
Compound A7 m/z＝582.3(M+H) + Compound C7 m/z＝598.3(M+H) +
Compound A8 m/z＝658.3(M+H) + Compound C9 m/z＝674.3(M+H) +
Compound A13 m/z＝582.3(M+H) + Compound C13 m/z＝598.3(M+H) +
Compound A16 m/z＝658.3(M+H) + Compound C14 m/z＝674.3(M+H) +
Compound B1 m/z＝657.3(M+H) + Compound D1 m/z＝608.3(M+H) +
Compound B5 m/z＝707.3(M+H) + Compound D5 m/z＝658.3(M+H) +
Compound B7 m/z＝657.3(M+H) + Compound D7 m/z＝608.3(M+H) +
Compound B12 m/z＝707.3(M+H) + Compound D12 m/z＝658.3(M+H) +
The nuclear magnetic data of a part of the compounds are shown in Table 4 below
TABLE 4 Table 4
Organic electroluminescent device preparation and evaluation:
the embodiment also provides an organic electroluminescent device, which comprises an anode, a cathode and a functional layer between the anode and the cathode, wherein the functional layer comprises the organic compound. Hereinafter, the organic electroluminescent device of the present application will be described in detail by way of examples. However, the following examples are merely examples of the present application, and are not limiting of the present application.
Example 1: preparation of green organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnOn the ITO/Ag/ITO substrate, ultraviolet ozone and O are used 2 :N 2 Plasma surface treatment to increase work function of anode, or cleaning ITO substrate surface with organic solventAnd (3) removing impurities and greasy dirt on the surface of the ITO substrate.
PD and compound HT-24 were co-evaporated on an experimental substrate (anode) at a deposition rate ratio of 2% to 98% to form a film having a thickness ofAnd evaporating HT-24 on the hole injection layer to form a layer having a thickness ofIs provided.
Vacuum evaporating HT-20 on the hole transport layer to form a film with a thickness ofIs provided.
On the hole-assist layer, a compound A1:H245:PD-1 (P type: N type: DOAPNT) was co-deposited at a film thickness ratio of 50:40:10% to form a film having a thickness ofAn organic light emitting layer (EML). />
Mixing ET-01 and LiQ in a weight ratio of 1:1 and evaporating to formA thick Electron Transport Layer (ETL), liQ is evaporated on the electron transport layer to form a thickness +.>Then, magnesium (Mg) and silver (Ag) are vacuum evaporated on the electron injection layer at an evaporation rate of 1:9 to form a film having a thickness +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAnd forming an organic capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Examples 2 to 20
An organic electroluminescent device was fabricated by referring to the method of example 1, except that the compound shown in table 5 below was substituted for the compound A1 in forming the organic light emitting layer.
Comparative examples 1 to 4
An organic electroluminescent device was fabricated by the method of reference example 1, except that compound I, compound II, compound III and compound iv were used instead of compound A1, respectively, in forming the organic light emitting layer.
For the organic electroluminescent device prepared as above, the temperature was 10mA/cm 2 The IVL performance of the device was analyzed under the conditions of T95 device lifetime at 20mA/cm 2 The test was performed under the conditions of (2) and the test results are shown in Table 5:
TABLE 5
As can be seen from Table 5 above, the use of the organic compound as an organic electroluminescent device of the present application has an improvement in current efficiency of at least 10.5% and an improvement in T95 life of at least 18.6% as compared with comparative examples 1 to 4.
The organic compound is a compound of which 3, 3-bicarbazole is combined with a dibenzofive-membered ring group, and the carbazole ring connected with the dibenzofive-membered ring is required to be subjected to total deuteration. The organic compound has good hole mobility and high first triplet state energy level; particularly, the carbazole group connected with the dibenzo five-membered ring in the structure is the part with higher spin density, namely more concentrated exciton energy, and the carbazole group is completely deuterated, so that the photoelectric stability of molecules can be effectively improved; meanwhile, the other carbazole is kept from deuteration, so that the symmetry of a molecular core structure can be effectively reduced, the molecular crystallinity is reduced, and the film forming capability of the material is improved. When the organic compound is used as a light-emitting layer main body in the organic electroluminescent device, the service life of the device can be remarkably prolonged while the low driving voltage and the high light-emitting efficiency are maintained. In particular, when the dibenzofive-membered ring is dibenzofuran/dibenzothiophene, the device performance is more excellent.
It is to be understood that the present application is not limited to the precise arrangements and instrumentalities shown in the drawings, which have been described above, and that various modifications and changes may be effected without departing from the scope thereof. The scope of the application is limited only by the appended claims.

Claims (2)

1. The organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;
the functional layer comprises an organic light emitting layer;
the organic light emitting layer includes a host material and a guest material; the host material comprises a compoundThe organic compound is shown, the guest material is +.>
The organic compound represented by formula 1 is selected from the group consisting of:
the organic electroluminescent device is a green organic electroluminescent device.
2. An electronic device comprising the organic electroluminescent device as claimed in claim 1.
CN202211226723.4A 2022-10-09 2022-10-09 Organic compound, organic electroluminescent device and electronic apparatus Active CN115894462B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN202211226723.4A CN115894462B (en) 2022-10-09 2022-10-09 Organic compound, organic electroluminescent device and electronic apparatus
PCT/CN2023/120210 WO2024078287A1 (en) 2022-10-09 2023-09-20 Organic compound, organic electroluminescent device, and electronic apparatus

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211226723.4A CN115894462B (en) 2022-10-09 2022-10-09 Organic compound, organic electroluminescent device and electronic apparatus

Publications (2)

Publication Number Publication Date
CN115894462A CN115894462A (en) 2023-04-04
CN115894462B true CN115894462B (en) 2024-04-09

Family

ID=86471633

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211226723.4A Active CN115894462B (en) 2022-10-09 2022-10-09 Organic compound, organic electroluminescent device and electronic apparatus

Country Status (2)

Country Link
CN (1) CN115894462B (en)
WO (1) WO2024078287A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115894462B (en) * 2022-10-09 2024-04-09 北京莱特众成光电材料科技有限公司 Organic compound, organic electroluminescent device and electronic apparatus

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111574995A (en) * 2019-02-15 2020-08-25 三星Sdi株式会社 Composition for photoelectric device, organic photoelectric device and display device
CN111584721A (en) * 2019-02-15 2020-08-25 三星Sdi株式会社 Composition for photoelectric device, organic photoelectric device and display device
CN114195700A (en) * 2021-10-28 2022-03-18 陕西莱特光电材料股份有限公司 Organic compound, and organic electroluminescent device and electronic device comprising the same
WO2022092625A1 (en) * 2020-10-30 2022-05-05 엘티소재주식회사 Heterocyclic compound, organic light-emitting device comprising same, composition for organic layer of organic light-emitting device, and method for manufacturing organic light-emitting device
CN114599647A (en) * 2020-09-28 2022-06-07 Lt素材株式会社 Heterocyclic compound, organic light-emitting device including the same, and composition of organic material layer for organic light-emitting device
WO2022211594A1 (en) * 2021-04-01 2022-10-06 삼성에스디아이 주식회사 Composition for organic optoelectronic device, organic optoelectronic device, and display device

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220177492A1 (en) * 2019-10-25 2022-06-09 Universal Display Corporation Organic electroluminescent materials and devices
KR20220013910A (en) * 2020-07-27 2022-02-04 엘티소재주식회사 Heterocyclic compound, and organic light emitting device comprising same
US20220109109A1 (en) * 2020-08-21 2022-04-07 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same
CN116396280A (en) * 2022-05-12 2023-07-07 陕西莱特光电材料股份有限公司 Organic compound, organic electroluminescent device and electronic apparatus
CN115894462B (en) * 2022-10-09 2024-04-09 北京莱特众成光电材料科技有限公司 Organic compound, organic electroluminescent device and electronic apparatus

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111574995A (en) * 2019-02-15 2020-08-25 三星Sdi株式会社 Composition for photoelectric device, organic photoelectric device and display device
CN111584721A (en) * 2019-02-15 2020-08-25 三星Sdi株式会社 Composition for photoelectric device, organic photoelectric device and display device
CN114599647A (en) * 2020-09-28 2022-06-07 Lt素材株式会社 Heterocyclic compound, organic light-emitting device including the same, and composition of organic material layer for organic light-emitting device
WO2022092625A1 (en) * 2020-10-30 2022-05-05 엘티소재주식회사 Heterocyclic compound, organic light-emitting device comprising same, composition for organic layer of organic light-emitting device, and method for manufacturing organic light-emitting device
CN116615419A (en) * 2020-10-30 2023-08-18 Lt素材株式会社 Heterocyclic compound, organic light-emitting element comprising same, composition for organic layer of organic light-emitting element, and method for manufacturing organic light-emitting element
WO2022211594A1 (en) * 2021-04-01 2022-10-06 삼성에스디아이 주식회사 Composition for organic optoelectronic device, organic optoelectronic device, and display device
CN114195700A (en) * 2021-10-28 2022-03-18 陕西莱特光电材料股份有限公司 Organic compound, and organic electroluminescent device and electronic device comprising the same

Also Published As

Publication number Publication date
WO2024078287A1 (en) 2024-04-18
CN115894462A (en) 2023-04-04

Similar Documents

Publication Publication Date Title
CN114133332B (en) Organic compound, electronic component, and electronic device
CN114989069B (en) Nitrogen-containing compound, electronic component and electronic device
CN114805179B (en) Nitrogen-containing compound, organic electroluminescent device and electronic device
WO2024078287A1 (en) Organic compound, organic electroluminescent device, and electronic apparatus
CN115385898B (en) Nitrogen-containing compound, organic electroluminescent device and electronic device
CN115109051B (en) Aromatic amine compound, organic electroluminescent device and electronic device
CN115521212B (en) Organic material, electronic element and electronic device
CN115490602B (en) Organic compound, electronic element using same and electronic device
CN113121565B (en) Organic compound, electronic element using same and electronic device
CN116396280A (en) Organic compound, organic electroluminescent device and electronic apparatus
CN114426539B (en) Organic compound, organic electroluminescent device and electronic device comprising the same
CN114497424B (en) Organic electroluminescent device and electronic device including the same
CN114335399B (en) Organic electroluminescent device and electronic device including the same
CN114075166B (en) Organic compound, and electronic element and electronic device using same
CN115521214B (en) Organic compound, and electronic component and electronic device including the same
CN113735893B (en) Organic compound, and electronic element and electronic device using same
CN114989179B (en) Organic compound, organic electroluminescent device using the same, and electronic device
CN114075214B (en) Organic compound, organic electroluminescent device and electronic device comprising the same
CN117417260A (en) Organic material, organic electroluminescent device and electronic device
CN118108658A (en) Nitrogen-containing compound, organic electroluminescent device and electronic device
CN117603192A (en) Organic compound, composition, organic electroluminescent device, and electronic device
CN117777137A (en) Organic compound, organic electroluminescent device and electronic device
CN117720545A (en) Nitrogen-containing compound, organic electroluminescent device and electronic device
CN117720539A (en) Organic compound, organic electroluminescent device and electronic device
CN116478115A (en) Organic compound, organic electroluminescent device and electronic apparatus

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
GR01 Patent grant
GR01 Patent grant