WO2024078287A1 - Composé organique, dispositif électroluminescent organique et appareil électronique - Google Patents

Composé organique, dispositif électroluminescent organique et appareil électronique Download PDF

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WO2024078287A1
WO2024078287A1 PCT/CN2023/120210 CN2023120210W WO2024078287A1 WO 2024078287 A1 WO2024078287 A1 WO 2024078287A1 CN 2023120210 W CN2023120210 W CN 2023120210W WO 2024078287 A1 WO2024078287 A1 WO 2024078287A1
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carbon atoms
group
organic compound
present application
organic
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PCT/CN2023/120210
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Chinese (zh)
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马天天
杨雷
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北京莱特众成光电材料科技有限公司
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Publication of WO2024078287A1 publication Critical patent/WO2024078287A1/fr

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    • 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

Definitions

  • 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.
  • organic electroluminescent materials have the advantages of ultra-thinness, self-luminescence, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage and low energy consumption. They have been widely used in industries such as flat panel displays, flexible displays, solid-state lighting and automotive displays.
  • the luminescent material plays an important role in the device efficiency of OLED.
  • the luminescent layer material it can be a host material and a guest material.
  • the luminescent layer of the organic electroluminescent device is used as a combination of a host and a dopant to improve color purity, luminous efficiency and stability.
  • this dopant/host material combination is used as an organic luminescent layer, the host material has a greater impact on the efficiency and life of the organic electroluminescent device. Therefore, it is necessary to continuously develop new host materials for organic electroluminescent devices with high efficiency, long life, and suitable for mass production.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device using the same having higher luminous efficiency and service life.
  • the first aspect of the present application provides an organic compound having a structure as shown in Formula 1:
  • Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms
  • X is selected from C(R 1 R 2 ), O, S or N(R 3 );
  • R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, A halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a halogenated aryl group having 6 to 12 carbon atoms, or a deuterated aryl group having 6 to 12 carbon atoms;
  • R3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms
  • the substituents in Ar and R3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a deuterated aryl group having 6 to 12 carbon atoms.
  • an organic electroluminescent device comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described in the first aspect of the present application.
  • the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound;
  • the organic electroluminescent device is a green organic electroluminescent device.
  • a third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect.
  • the organic compound of the present application is a class of compounds in which 3,3-dicarbazole is combined with a dibenzo pentacyclic ring group, and the carbazole ring connected to the dibenzo pentacyclic ring must be fully deuterated.
  • the organic compound of the present application has good hole mobility and a high first triplet energy level; in particular, the carbazole group connected to the dibenzo pentacyclic ring in the structure is a place where the spin density is relatively high, that is, the exciton energy is relatively concentrated.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
  • the purpose of the present application is to provide an organic compound and an organic electroluminescent device and an electronic device comprising the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and the electronic device, such as reducing the driving voltage of the device and improving the efficiency and life of the device.
  • an organic compound wherein the organic compound has a structure as shown in Formula 1:
  • Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms
  • X is selected from C(R 1 R 2 ), O, S or N(R 3 );
  • R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a halogenated aryl group having 6 to 12 carbon atoms or a deuterated aryl group having 6 to 12 carbon atoms;
  • R3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms
  • the substituents in Ar and R3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a deuterated aryl group having 6 to 12 carbon atoms.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means:
  • Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other;
  • Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl having a substituent Rc or an unsubstituted aryl.
  • Rc can be, for example, deuterium, cyano, halogen group, alkyl, haloalkyl, deuterated alkyl, phenyl, deuterated aryl, haloaryl, cycloalkyl, etc.
  • the number of substitutions can be 1 or more.
  • plural means more than 2, for example, 2, 3, 4, 5, 6, etc.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms.
  • L1 is a substituted arylene group having 12 carbon atoms
  • the total number of carbon atoms of the arylene group and the substituents thereon is 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, a monocyclic aryl group and a condensed aryl group conjugated by a carbon-carbon bond, two or more aryl groups conjugated by a carbon-carbon bond, or a condensed aryl group conjugated by a carbon-carbon bond.
  • condensed ring aromatic groups can include, for example, bicyclic condensed aromatic groups (such as naphthyl), tricyclic condensed aromatic groups (such as phenanthrenyl, fluorenyl, anthracenyl), etc.
  • the aromatic group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • aromatic groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl,
  • the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
  • terphenyl includes
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.
  • the carbon number of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18 or 20.
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms
  • the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • the fluorenyl group may be substituted by 1 or 2 substituents, wherein, when the fluorenyl group is substituted, it may be: etc., but not limited thereto.
  • aryl group as a substituent of Ar is exemplified but not limited to phenyl and the like.
  • 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 in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 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.
  • the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
  • haloalkyl group examples include, but are not limited to, trifluoromethyl.
  • deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
  • deuterated aryl groups include, but are not limited to, pentadeuterated phenyl groups.
  • the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10.
  • Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
  • no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.
  • the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring, and the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10).
  • the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positioned connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any one of the formulas (X'-1) to (X'-4) Possible connection methods.
  • the organic compound is selected from the compounds shown in Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:
  • the organic compound is selected from the compounds shown in 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 or Formula 2-1-V:
  • Ar is selected from substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms.
  • the substituents in Ar are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a pentadeuterated phenyl group.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted biphenyl.
  • the substituents in Ar are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.
  • Ar is selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of the following groups:
  • the substituted group V has one or more substituents, and the substituents are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and pentadeuterated phenyl.
  • substituents are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, and pentadeuterated phenyl.
  • the number of substituents on the group V is greater than 1, the substituents are the same or different.
  • Ar is selected from the group consisting of:
  • Ar is selected from the group consisting of:
  • R 3 is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.
  • the substituents in R 3 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a pentadeuterated phenyl group.
  • R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted cyclopentyl. Phenyl.
  • the substituents in R 3 are the same or different and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, phenyl or pentadeuterated phenyl.
  • R3 is selected from the group consisting of the following groups:
  • R3 is selected from the group consisting of:
  • R 3 is phenyl
  • R 1 and R 2 are both methyl.
  • the organic compound is selected from the group consisting of the following compounds:
  • the present application provides an organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.
  • the functional layer comprises an organic light-emitting layer.
  • the organic light-emitting layer comprises the organic compound of the present application.
  • the organic electroluminescent device is a phosphorescent device.
  • the organic electroluminescent device is a green organic electroluminescent device.
  • the organic electroluminescent device includes an anode (ITO substrate), a hole transport layer, a hole auxiliary layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture) and an organic covering layer in sequence.
  • ITO substrate anode
  • hole transport layer a hole transport layer
  • hole auxiliary layer an organic light-emitting layer
  • electron transport layer an electron injection layer
  • Mg-Ag mixture cathode
  • the organic electroluminescent device of the present application includes an anode 100, a cathode 200 arranged opposite to the anode 100, and at least one functional layer 300 between the anode layer and the cathode layer, and the functional layer 300 includes 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 stacked in sequence.
  • the anode 100 includes the following anode materials, which are preferably materials with a large work function that facilitate hole injection into the organic layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
  • the anode uses an ITO substrate.
  • the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbide
  • the hole transport material may be selected from carbide
  • the present application does not specifically limit the above-mentioned compounds.
  • the hole transport layer 320 is composed of HT-24.
  • the hole auxiliary layer 330 may include one or more hole transport materials, and the hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in this application.
  • the hole auxiliary layer 330 is composed of HT-20.
  • a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320.
  • the hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation on this.
  • the material of the hole injection layer 310 may be selected from the following compounds or any combination thereof;
  • the hole injection layer 310 is composed of PD and HT-24.
  • the organic light-emitting layer 340 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • 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 340 may be recombined in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the host material, and the host material 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 mixed host material, wherein the mixed host material includes a hole-type host material and an electron-type host material.
  • the electron-type host material may be a triazine material, a quinoline material, etc., and the present application does not impose any special restrictions on this.
  • the electronic host material (N type) of the organic light-emitting layer is H45
  • the hole-type host material (P-type) of the organic light-emitting layer is the organic compound of the present application.
  • the guest material (DOPANT) of the organic light-emitting layer 340 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this.
  • the guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. For example, specific examples of the green phosphorescent dopant include, but are not limited to,
  • the organic electroluminescent device is a green organic electroluminescent device
  • the host material of the organic electroluminescent layer 340 is the organic compound of the present application and H45
  • the guest material (DOPANT) is PD-11.
  • the electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not make any special restrictions on this.
  • the 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:
  • the electron transport layer 350 may be composed of ET-01 and LiQ.
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates electron injection into the organic layer.
  • 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 multilayer materials such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca, but are not limited thereto.
  • a metal electrode including silver and magnesium is preferably used as the cathode.
  • an electron injection layer 360 may 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 inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance.
  • the electron injection layer 360 may include LiQ.
  • the present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.
  • the electronic device provided in the present application is a first electronic device 400
  • the first electronic device 400 includes any one of the organic electroluminescent devices described in the above-mentioned organic electroluminescent device embodiments.
  • the electronic device may be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and the present application will not repeat them here.
  • N-phenyl-3-carbazole boronic 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 round-bottom flask protected by nitrogen, the temperature was raised to 75°C to 80°C, and the reaction was stirred for 24 hours; the reaction solution was cooled to room temperature and filtered, and the obtained solid was rinsed with water and ethanol and then dried to obtain a crude product; the crude product was purified by recrystallization using toluene to obtain a light gray solid intermediate a1 (10.6 g
  • reactant A was used to replace N-phenyl-3-carbazole boronic acid to synthesize the intermediates shown in Table 1 below:
  • the present application also provides an organic electroluminescent device, including an anode, a cathode, and a functional layer between the anode and the cathode, wherein the functional layer includes the organic compound of the present application.
  • an organic electroluminescent device including an anode, a cathode, and a functional layer between the anode and the cathode, wherein the functional layer includes the organic compound of the present application.
  • the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode.
  • the surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
  • HIL hole injection layer
  • HT-20 was vacuum-deposited on the hole transport layer to form a layer with a thickness of of the hole-assisting layer.
  • compound A1:H45:PD-1 (P-type: N-type: DOAPNT) was co-evaporated at a film thickness ratio of 50%:40%:10% to form a film with a thickness of of an organic light-emitting layer (EML).
  • EML organic light-emitting layer
  • ET-01 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating LiQ on the electron transport layer to form a Then, magnesium (Mg) and silver (Ag) are vacuum-deposited on the electron injection layer at a deposition rate of 1:9 to form a layer with a thickness of cathode.
  • ETL electron transport layer
  • Mg magnesium
  • Ag silver
  • a layer with a thickness of The CP-1 is formed to form an organic cover layer (CPL), thereby completing the manufacture of the organic light-emitting device.
  • CPL organic cover layer
  • An organic electroluminescent device was prepared by referring to the method of Example 1, except that, when forming the organic light-emitting layer, the compound shown in the following Table 5 was used instead of Compound A1.
  • An organic electroluminescent device was prepared by referring to the method of Example 1, except that when forming the organic light-emitting layer, Compound I, Compound II, Compound III and Compound IV were used to replace Compound A1 respectively.
  • the organic compound of the present application is a class of compounds in which 3,3-dicarbazole is combined with a dibenzo pentacyclic ring group, and the carbazole ring connected to the dibenzo pentacyclic ring must be fully deuterated.
  • the organic compound of the present application has good hole mobility and a high first triplet energy level; in particular, the carbazole group connected to the dibenzo pentacyclic ring in the structure is a place where the spin density is high, that is, the exciton energy is more concentrated.

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Abstract

La présente invention se rapporte au domaine technique de l'électroluminescence organique, et concerne un composé organique, ainsi qu'un dispositif électroluminescent organique et un appareil électronique utilisant celui-ci. Le composé organique a la structure représentée dans la formule 1. Lorsque le composé organique est utilisé dans le dispositif électroluminescent organique, les performances du dispositif électroluminescent organique peuvent être considérablement améliorées.
PCT/CN2023/120210 2022-10-09 2023-09-20 Composé organique, dispositif électroluminescent organique et appareil électronique WO2024078287A1 (fr)

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CN202211226723.4A CN115894462B (zh) 2022-10-09 2022-10-09 有机化合物、有机电致发光器件和电子装置
CN202211226723.4 2022-10-09

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