WO2024078287A1 - Organic compound, organic electroluminescent device, and electronic apparatus - Google Patents

Organic compound, organic electroluminescent device, and electronic apparatus 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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French (fr)
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/en

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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

The present application relates to the technical field of organic electroluminescence, and relates to an organic compound and an organic electroluminescent device and electronic apparatus using same. The organic compound has the structure shown in formula 1. When the organic compound is used in the organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

有机化合物、有机电致发光器件和电子装置Organic compound, organic electroluminescent device and electronic device
相关申请的交叉引用CROSS-REFERENCE TO RELATED APPLICATIONS
本申请要求于2022年10月9日递交的申请号为202211226723.4的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。This application claims priority to Chinese patent application No. 202211226723.4 filed on October 9, 2022. The entire text of the above Chinese patent application is hereby cited as part of this application.
技术领域Technical Field
本申请涉及有机电致发光技术领域，具体地，涉及一种有机化合物及使用其的有机电致发光器件和电子装置。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.
背景技术Background technique
有机电致发光材料(OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。As a new generation of display technology, organic electroluminescent materials (OLEDs) 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.
目前，对于有机电致发光器件而言，发光材料对OLED的器件效率起重要作用。对于发光层材料，可以为主体材料和客体材料。而有机电致发光器件的发光层，有机发光层为主体和掺杂剂的组合来使用，从而提高颜色纯度、发光效率和稳定性。然而，当使用此种掺杂剂/主体材料组合作为有机发光层时，主体材料对有机电致发光器件的效率和寿命的影响较大，因此，需要不断地开发高效率，长寿命，适于量产的用于有机电致发光器件的新型主体材料。At present, for organic electroluminescent devices, the luminescent material plays an important role in the device efficiency of OLED. For 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. However, when 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.
需要说明的是，在上述背景技术部分公开的信息仅用于加强对本申请的背景的理解，因此可以包括不构成对本领域普通技术人员已知的现有技术的信息。It should be noted that the information disclosed in the above background technology section is only used to enhance the understanding of the background of the present application, and therefore may include information that does not constitute the prior art known to ordinary technicians in the field.
发明内容Summary of the invention
本申请的目的是提供一种有机化合物以及使用其的具有较高的发光效率和使用寿命的有机电致发光器件和电子装置。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.
为了实现上述目的，本申请第一方面提供一种有机化合物，该有机化合物具有如式1所示的结构：
In order to achieve the above-mentioned object, the first aspect of the present application provides an organic compound having a structure as shown in Formula 1:
其中，Ar选自碳原子数为6～20的取代或未取代的芳基；wherein Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms;
X选自C(R1R2)、O、S或N(R3)；X is selected from C(R 1 R 2 ), O, S or N(R 3 );
R1和R2相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、 碳原子数为1～10的卤代烷基、碳原子数为6～12的芳基、碳原子数为6～12的卤代芳基或者碳原子数为6～12的氘代芳基； 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选自碳原子数为6～20的取代或未取代的芳基； R3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;
Ar和R3中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基或碳原子数为6～12的氘代芳基。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.
本申请的第二方面，提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的有机化合物。In a second aspect of the present application, an organic electroluminescent device is provided, 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.
优选地，所述功能层包括有机发光层，所述有机发光层包含所述有机化合物；Preferably, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound;
优选地，所述有机电致发光器件为绿色有机电致发光器件。Preferably, the organic electroluminescent device is a green organic electroluminescent device.
本申请的第三方面，提供一种电子装置，包括第二方面所述的有机电致发光器件。A third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect.
本申请的有机化合物为3,3-联咔唑结合二苯并五元环基团的一类化合物，且连接二苯并五元环的咔唑环上必须全氘代。本申请的有机化合物有着良好的空穴迁移率以及高的第一三重态能级；特别地，该结构中连接二苯并五元环的咔唑基团为自旋密度较高即激子能量较为集中之处，将此咔唑基团进行完全氘代，可以有效提升分子的光电稳定性；与此同时，保持另一咔唑基不被氘代，可以有效降低分子核心结构的对称性，降低分子结晶性，提升材料成膜能力。将本申请的有机化合物作为有机电致发光器件中发光层主体使用时，可以在保持低的驱动电压和高的发光效率的同时，显著提升器件寿命。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. Completely deuterating this carbazole group can effectively improve the photoelectric stability of the molecule; at the same time, keeping the other carbazole group undeuterated can effectively reduce the symmetry of the molecular core structure, reduce the molecular crystallinity, and improve the film-forming ability of the material. When the organic compound of the present application is used as the main body of the light-emitting layer in an organic electroluminescent device, the device life can be significantly improved while maintaining a low driving voltage and a high luminous efficiency.
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。Other features and advantages of the present application will be described in detail in the subsequent specific implementation section.
附图说明BRIEF DESCRIPTION OF THE DRAWINGS
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。在附图中：The accompanying drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application but do not constitute a limitation to the present application. In the accompanying drawings:
图1是本申请一种实施方式的有机电致发光器件的结构示意图。FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
图2是本申请一种实施方式的电子装置的结构示意图。FIG. 2 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
附图标记说明
100、阳极           200、阴极             300、功能层           310、空穴注入层
320、空穴传输层      330、空穴辅助层       340、有机发光层       350、电子传输层
360、电子注入层      400、第一电子装置Description of Reference Numerals
100, anode 200, cathode 300, functional layer 310, 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. first electronic device
具体实施方式Detailed ways
针对现有技术存在的上述问题，本申请的目的在于提供一种有机化合物及包含该有机化合物的有机电致发光器件和电子装置，所述有机化合物可以改善有机电致发光器件和电子装置的性能，例如降低器件的驱动电压，提升器件效率和寿命。In view of the above-mentioned problems existing in the prior art, 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.
本申请的第一方面，提供一种有机化合物，该有机化合物具有如式1所示的结构：
In a first aspect of the present application, an organic compound is provided, wherein the organic compound has a structure as shown in Formula 1:
其中，Ar选自碳原子数为6～20的取代或未取代的芳基；wherein Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms;
X选自C(R1R2)、O、S或N(R3)；X is selected from C(R 1 R 2 ), O, S or N(R 3 );
R1和R2相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的卤代烷基、碳原子数为6～12的芳基、碳原子数为6～12的卤代芳基或者碳原子数为6～12的氘代芳基； 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选自碳原子数为6～20的取代或未取代的芳基； R3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;
Ar和R3中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基或碳原子数为6～12的氘代芳基。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.
本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……各自独立地为”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。In this application, the descriptions "each... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, 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.
本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。举例来讲，“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即Rc例如可以为氘、氰基、卤素基团、烷基、卤代烷基、氘代烷基、苯基、氘代芳基、卤代芳基、环烷基等。取代的个数可以是1个或多个。In the present application, the term "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). For example, "substituted or unsubstituted aryl" refers to an aryl having a substituent Rc or an unsubstituted aryl. The above-mentioned substituent, i.e., 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.
本申请中，“多个”是指2个以上，例如2个、3个、4个、5个、6个，等。In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.
本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L1为碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if 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.
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或 者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、三亚苯基、苝基、苯并[9,10]菲基、芘基、苯并荧蒽基、基、螺二芴基等。本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。In the present application, 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. In other words, 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. or more condensed ring aromatic groups. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon conjugation can also be regarded as aromatic groups of the present application. Among them, 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. Examples of aromatic groups can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
本申请中，三联苯基包括 In the present application, terphenyl includes
本申请中，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。In the present application, 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. For example, 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.
本申请中，取代或未取代的芳基的碳原子数可以为6、10、12、13、14、15、16、17、18或20。在一些实施方案中，取代或未取代的芳基是碳原子数为6～20的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～18的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～15的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～12的取代或未取代的芳基。In the present application, the carbon number 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 6 to 20 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
本申请中，芴基可以被1个或2个取代基取代，其中，在上述芴基被取代的情况下，可以为：等，但并不限定于此。In the present application, 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.
本申请中，作为Ar的取代基的芳基例如但不限于，苯基等等。In the present application, the aryl group as a substituent of Ar is exemplified but not limited to phenyl and the like.
本申请中，碳原子数为1～10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5、6、7、8、9、10个，烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基等。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 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.
本申请中，卤素基团例如可以为氟、氯、溴、碘。In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
本申请中，卤代烷基的具体实例包括但不限于，三氟甲基。In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
本申请中，氘代烷基的具体实例包括但不限于，三氘代甲基。In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
本申请中，氘代芳基的具体实例包括但不限于，五氘代苯基。In the present application, specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl groups.
本申请中，碳原子数为3～10的环烷基的碳原子数例如可以为3、4、5、6、7、8或10。环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。In the present application, 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.
本申请中，不定位连接键涉及的从环体系中伸出的单键其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式。
In this application, 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. For example, as shown in the following formula (f), 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).
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一 可能的连接方式。
For example, as shown in the following formula (X'), 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.
在本申请一些实施方式中，所述有机化合物选自式1-1、式1-2、式1-3或者式1-4所示的化合物：
In some embodiments of the present application, the organic compound is selected from the compounds shown in Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:
在本申请一些具体的实施方式中，所述有机化合物选自式2-1-A、式2-1-B、式2-1-C、式2-1-D、式2-1-E、式2-1-F、式2-1-G、式2-1-H、式2-1-L、式2-1-M、式2-1-N、式2-1-P、式2-1-R、式2-1-U或者式2-1-V所示的化合物：

In some specific embodiments of the present application, 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:

在本申请一些实施方式中，Ar选自碳原子数为6～12的取代或未取代的芳基。In some embodiments of the present application, Ar is selected from substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms.
可选地，Ar中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、苯基或五氘代苯基。Optionally, 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.
在本申请另一些实施方式中，Ar选自取代或未取代的苯基、取代或未取代的萘基或未取代的联苯基。In other embodiments of the present application, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted biphenyl.
可选地，Ar中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基或五氘代苯基。Optionally, 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.
在本申请一些实施方式中，Ar选自取代或未取代的基团V，其中，未取代的基团V选自以下基团组成的组：
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 following groups:
取代的基团V中具有一个或两个以上取代基，取代基分别独立地选自由氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、五氘代苯基所组成的组，且当基团V上的取代基个数大于1时，各取代基相同或不同。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. When the number of substituents on the group V is greater than 1, the substituents are the same or different.
可选地，Ar选自以下基团组成的组：
Optionally, Ar is selected from the group consisting of:
具体地，Ar选自以下基团组成的组：
Specifically, Ar is selected from the group consisting of:
在本申请一些实施方式中，R3选自碳原子数为6～12取代或未取代的芳基。In some embodiments of the present application, R 3 is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.
可选地，R3中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、苯基或五氘代苯基。Optionally, 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.
在本申请一些实施方式中，R3选自取代或未取代的苯基、取代或未取代的萘基或未取代的联 苯基。In some embodiments of the present application, R3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted cyclopentyl. Phenyl.
可选地，R3中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、苯基或五氘代苯基。Optionally, 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.
在本申请一些实施方式中，R3选自以下基团组成的组：
In some embodiments of the present application, R3 is selected from the group consisting of the following groups:
具体地，R3选自以下基团组成的组：
Specifically, R3 is selected from the group consisting of:
进一步可选地，R3为苯基。Further optionally, R 3 is phenyl.
在本申请一些实施方式中，R1和R2均为甲基。In some embodiments of the present application, R 1 and R 2 are both methyl.
在本申请一些实施方式中，所述有机化合物选自以下化合物组成的组：





In some embodiments of the present application, the organic compound is selected from the group consisting of the following compounds:





本申请的第二方面，本申请提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于阳极和阴极之间的功能层；所述功能层包含本申请的有机化合物。In a second aspect of the present application, 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.
可选地，所述功能层包含有机发光层。Optionally, the functional layer comprises an organic light-emitting layer.
进一步可选地，所述有机发光层包含本申请的有机化合物。Further optionally, the organic light-emitting layer comprises the organic compound of the present application.
在本申请一些实施方式中，所述有机电致发光器件为磷光器件。In some embodiments of the present application, the organic electroluminescent device is a phosphorescent device.
在本申请的一些具体实施方式中，所述有机电致发光器件为绿色有机电致发光器件。In some specific embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.
在本申请一些实施方式中，有机电致发光器件依次包括阳极(ITO基板)、空穴传输层、空穴辅助层、有机发光层、电子传输层、电子注入层、阴极(Mg-Ag混合物)和有机覆盖层。In some embodiments of the present application, 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.
在本申请的一种具体实施方式中，如图1所示，本申请的有机电致发光器件包括阳极100、与阳极100相对设置的阴极200、以及介于阳极层与阴极层之间的至少一层功能层300，该功能层300包括依次层叠设置的空穴注入层310、空穴传输层320、空穴辅助层330、有机发光层340、电子传输层350以及电子注入层360。In a specific embodiment of the present application, as shown in Figure 1, 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.
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至有机层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。在本申请一种具体的实施方式中，阳极选用ITO基板。Optionally, 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. Specific examples of 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. In a specific embodiment of the present application, the anode uses an ITO substrate.
可选地，空穴传输层320可以包括一种或者多种空穴传输材料，空穴传输材料可以选自咔 唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。举例而言，在本申请的一些实施方式中，空穴传输层320由HT-24组成。
Optionally, the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbide The present application does not specifically limit the above-mentioned compounds. For example, in some embodiments of the present application, the hole transport layer 320 is composed of HT-24.
可选地，空穴辅助层330可以包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。举例而言，在本申请的一些实施方式中，空穴辅助层330由HT-20组成。Optionally, 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. For example, in some embodiments of the present application, the hole auxiliary layer 330 is composed of HT-20.
可选地，在阳极100和空穴传输层320之间还可以设置有空穴注入层310，以增强向空穴传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。所述空穴注入层310的材料例如可以选自如下化合物或者其任意组合；
Optionally, 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;
在本申请的一种实施方式中，空穴注入层310由PD和HT-24组成。In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-24.
可选地，有机发光层340可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机发光层340由主体材料和客体材料组成，注入有机发光层340的空穴和注入有机发光层340的电子可以在有机发光层340复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。Optionally, 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. Optionally, 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.
有机发光层340的主体材料可以为混合型主体材料，其中，混合型主体材料中包含空穴型主体材料和电子型主体材料。电子型主体材料可以为三嗪类材料、喹啉类材料等等，本申请对此不做特殊的限制。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.
在本申请一种具体的实施方式中，有机发光层的电子型主体材料(N型)为H45 In a specific embodiment of the present application, the electronic host material (N type) of the organic light-emitting layer is H45
在本申请一种具体的实施方式中，有机发光层的空穴型主体材料(P型)为本申请有机化合物。In a specific embodiment of the present application, the hole-type host material (P-type) of the organic light-emitting layer is the organic compound of the present application.
有机发光层340的客体材料(DOPANT)可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。客体材料又称为掺杂材料或掺杂剂。按发光类型可以分为荧光掺杂剂和磷光掺杂剂。。例如，所述绿光磷光掺杂剂的具体实例包括但不限于，

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,

在本申请的一种实施方式中，所述有机电致发光器件为绿色有机电致发光器件，有机电致发光层340的主体材料为本申请有机化合物和H45，客体材料(DOPANT)为PD-11。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 of the present application and H45, and the guest material (DOPANT) is PD-11.
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，在本申请的一些实施方式中，电子传输层350可以由ET-01和LiQ组成。所述电子传输层350的材料包含但不限于以下化合物：
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. For example, in some embodiments of the present application, 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:
在本申请的一种实施方式中，电子传输层350可以由ET-01和LiQ组成。In one embodiment of the present application, the electron transport layer 350 may be composed of ET-01 and LiQ.
可选地，阴极200包括以下阴极材料，其是有助于电子注入至有机层中的具有小逸出功的材料。阴极材料的具体实例包括：金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al，Liq/Al，LiO2/Al，LiF/Ca，LiF/Al和BaF2/Ca，但不限于此。优选包括银和镁的金属电极作为阴极。Optionally, 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. 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 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.
可选地，在阴极200和电子传输层350之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。在本申请的一些实施方式中，电子注入层360可以包括LiQ。Optionally, 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. In some embodiments of the present application, the electron injection layer 360 may include LiQ.
本申请还提供一种电子装置，该电子装置包括本申请所述的有机电致发光器件。The present application also provides an electronic device, which includes the organic electroluminescent device described in the present application.
举例而言，如图2所示，本申请提供的电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。该电子装置可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于第一电子装置400具有上述有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。For example, as shown in FIG2 , the electronic device provided in the present application is a first electronic device 400, and 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.
下面将结合实施例详细描述本申请，但是，以下描述是用于解释本申请，而不是以任意方式 限制本申请的范围。The present application will be described in detail below in conjunction with the embodiments. However, the following description is intended to explain the present application and is not intended to be construed in any way. Limit the scope of this application.
中间体a1的合成：
Synthesis of intermediate a1:
将N-苯基-3-咔唑硼酸(10.0g；34.8mmol)，3-溴咔唑-D7(8.8g；34.8mmol)，四(三苯基膦)钯(0.8g；0.7mmol)，碳酸钾(9.6g；69.7mmol)，四丁基溴化铵(2.2g；7.0mmol)，甲苯(80mL)，乙醇(20mL)和去离子水(20mL)加入氮气保护的圆底烧瓶中，升温至75℃～80℃，搅拌反应24小时；将反应液降至室温，过滤，所得固体使用水和乙醇淋洗后干燥，得到粗品；粗品使用甲苯进行重结晶提纯，得到浅灰色固体中间体a1(10.6g；收率：73％)。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; yield: 73%).
参照中间体a1的合成方法，以反应物A替代N-苯基-3-咔唑硼酸，合成下表1所示的中间体：Referring to the synthesis method of intermediate a1, reactant A was used to replace N-phenyl-3-carbazole boronic acid to synthesize the intermediates shown in Table 1 below:
表1

Table 1

化合物A1的合成：
Synthesis of compound A1:
将中间体a1(5.0g；12.0mmol)，3-溴二苯并呋喃(3.1g；12.6mmol)，三(二亚苄基丙酮)二钯(0.1g；0.1mmol)，三叔丁基膦(0.05g；0.2mmol)，叔丁醇钠(1.7g；18.0mmol)和二甲苯(50mL)加入圆底烧瓶中，氮气保护下，于135℃～140℃搅拌反应12小时；停止反应降至室温，反应液使用去离子水洗后分液，有机相使用无水硫酸镁干燥，减压除去溶剂，得到粗品；所得粗品以甲苯作为洗脱剂进行硅胶柱色谱提纯，而后以甲苯/正庚烷作为溶剂进行重结晶提纯，得到白色固体化合物A1(5.1g；收率：73％)。Intermediate a1 (5.0 g; 12.0 mmol), 3-bromodibenzofuran (3.1 g; 12.6 mmol), tri(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-bottom flask, and stirred at 135°C to 140°C for 12 hours under nitrogen protection; the reaction was stopped and cooled to room temperature, the reaction solution was washed with deionized water and then separated, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using toluene as an eluent, and then purified by recrystallization using toluene/n-heptane as a solvent to obtain a white solid compound A1 (5.1 g; yield: 73%).
参照化合物A1的合成方法，以反应物C替代中间体a1，反应物B替代3-溴二苯并呋喃，合成下表2中化合物：Referring to the synthesis method of compound A1, the intermediate a1 is replaced by reactant C, and 3-bromodibenzofuran is replaced by reactant B to synthesize the compounds in Table 2 below:
表2



Table 2



部分化合物质谱数据如下表3所示The mass spectrometry data of some compounds are shown in Table 3 below
表3

table 3

部分化合物核磁数据如下表4所示The NMR data of some compounds are shown in Table 4 below
表4
Table 4
有机电致发光器件制备及评估：Preparation and evaluation of organic electroluminescent devices:
本申请实施方式还提供了一种有机电致发光器件，包括阳极、阴极以及介于阳极和阴极之间的功能层，功能层包括本申请的上述有机化合物。下面，通过实施例对本申请的有机电致发光器件进行详细说明。但是，下述实施例仅是本申请的示例，而非限定本申请。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. The organic electroluminescent device of the present application is described in detail below by way of examples. However, the following examples are merely examples of the present application, and do not limit the present application.
实施例1：绿色有机电致发光器件的制备Example 1: Preparation of green organic electroluminescent device
先通过以下过程进行阳极预处理：在厚度依次为的ITO/Ag/ITO基板上，利用紫外臭氧以及O2:N2等离子进行表面处理，以增加阳极的功函数，也可采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。First, 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.
在实验基板(阳极)上，将PD和化合物HT-24以2％﹕98％的蒸镀速率比例进行共同蒸镀，形成厚度为的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-24，形成厚度为的空穴传输层。On the experimental substrate (anode), PD and compound HT-24 were co-evaporated at an evaporation rate ratio of 2%:98% to form a layer with a thickness of A hole injection layer (HIL) is formed by evaporating HT-24 on the hole injection layer to form a thickness of hole transport layer.
在空穴传输层上真空蒸镀HT-20，形成厚度为的空穴辅助层。HT-20 was vacuum-deposited on the hole transport layer to form a layer with a thickness of of the hole-assisting layer.
在空穴辅助层上，将化合物A1﹕H45﹕PD-1(P型：N型：DOAPNT)以50％﹕40％﹕10％的膜厚比进行共同蒸镀，形成厚度为的有机发光层(EML)。On 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).
将ET-01和LiQ以1:1的重量比进行混合并蒸镀形成了厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1﹕9的蒸镀速率，真空蒸镀在电子注入层上，形成厚度为的阴极。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.
此外，在上述阴极上蒸镀厚度为的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。In addition, 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.
实施例2～20Embodiments 2 to 20
参照实施例1的方法制作有机电致发光器件，区别在于，在形成有机发光层时，以下表5中所示的化合物替代化合物A1。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.
比较例1～4Comparative Examples 1 to 4
参照实施例1的方法制作有机电致发光器件，区别在于，在形成有机发光层时，分别以化合物I、化合物II、化合物III和化合物Ⅳ替代化合物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.
对如上制得的有机电致发光器件，在10mA/cm2的条件下分析了器件的IVL性能，T95器件寿命在20mA/cm2的条件下进行测试，测试结果见表5：For the organic electroluminescent device prepared as above, the IVL performance of the device was analyzed under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 5:
表5

table 5

根据上表5可知，本申请的有机化合物用作有机电致发光器件与比较例1～4相比，电流效率至少提高了10.5％，T95寿命至少提高了18.6％。According to Table 5 above, when the organic compound of the present application is used as an organic electroluminescent device, the current efficiency is at least increased by 10.5%, and the T95 life is at least increased by 18.6% compared with Comparative Examples 1 to 4.
本申请的有机化合物为3,3-联咔唑结合二苯并五元环基团的一类化合物，且连接二苯并五元环的咔唑环上必须全氘代。本申请的有机化合物有着良好的空穴迁移率以及高的第一三重态能级；特别地，该结构中连接二苯并五元环的咔唑基团为自旋密度较高即激子能量较为集中之处，将此咔唑基团进行完全氘代，可以有效提升分子的光电稳定性；与此同时，保持另一咔唑基不被氘代，可以有效降低分子核心结构的对称性，降低分子结晶性，提升材料成膜能力。将本申请的有机化合物作为有机电致发光器件中发光层主体使用时，可以在保持低的驱动电压和高的发光效率的同时，显著提升器件寿命。特别地，当二苯并五元环为二苯并呋喃基/二苯并噻吩基时，器件性能更优。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. Completely deuterating this carbazole group can effectively improve the photoelectric stability of the molecule; at the same time, keeping the other carbazole group undeuterated can effectively reduce the symmetry of the molecular core structure, reduce the molecular crystallinity, and improve the film-forming ability of the material. When the organic compound of the present application is used as the main body of the light-emitting layer in an organic electroluminescent device, the device life can be significantly improved while maintaining a low driving voltage and a high luminous efficiency. In particular, when the dibenzo pentacyclic ring is a dibenzofuranyl/dibenzothiophene group, the device performance is better.
应当理解的是，本申请并不局限于上面已经描述并在附图中示出的精确结构，并且可以在不脱离其范围进行各种修改和改变。本申请的范围仅由所附的权利要求书来限制。 It should be understood that the present application is not limited to the precise structures that have been described above and shown in the drawings, and that various modifications and changes may be made without departing from the scope thereof. The scope of the present application is limited only by the appended claims.

Claims (10)

  1. 一种有机化合物，其特征在于，该有机化合物具有如式1所示的结构：
    An organic compound, characterized in that the organic compound has a structure as shown in Formula 1:
    其中，Ar选自碳原子数为6～20的取代或未取代的芳基；wherein Ar is selected from substituted or unsubstituted aromatic groups having 6 to 20 carbon atoms;
    X选自C(R1R2)、O、S或N(R3)；X is selected from C(R 1 R 2 ), O, S or N(R 3 );
    R1和R2相同或不同，分别独立地选自碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的卤代烷基、碳原子数为6～12的芳基、碳原子数为6～12的卤代芳基或者碳原子数为6～12的氘代芳基； 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选自碳原子数为6～20的取代或未取代的芳基； R3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;
    Ar和R3中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为1～10的氘代烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为6～12的芳基或碳原子数为6～12的氘代芳基。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.
  2. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自式1-1、式1-2、式1-3或者式1-4所示的化合物：
    The organic compound according to claim 1, characterized in that the organic compound is selected from the compounds represented by Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:
  3. 根据权利要求1所述的有机化合物，其特征在于，Ar和R3相同或不同，分别独立地选自碳原子数为6～12的取代或未取代的芳基；The organic compound according to claim 1, characterized in that Ar and R 3 are the same or different and are independently selected from substituted or unsubstituted aromatic groups having 6 to 12 carbon atoms;
    优选地，Ar和R3中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、苯基或五氘代苯基。Preferably, the substituents in Ar and 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.
  4. 根据权利要求1所述的有机化合物，其特征在于，Ar选自取代或未取代的苯基、取代或未取代的萘基或未取代的联苯基；The organic compound according to claim 1, characterized in that Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted biphenyl;
    优选地，Ar中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基或五氘代苯基。Preferably, 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.
  5. 根据权利要求1所述的有机化合物，其特征在于，Ar选自以下基团组成的组：
    The organic compound according to claim 1, characterized in that Ar is selected from the group consisting of the following groups:
  6. 根据权利要求1所述的有机化合物，其特征在于，R3选自取代或未取代的苯基、取代或未取代的萘基或未取代的联苯基；The organic compound according to claim 1, characterized in that R 3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or unsubstituted biphenyl;
    优选地，R3中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、苯基或五氘代苯基。Preferably, 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.
  7. 根据权利要求1所述的有机化合物，其特征在于，R1和R2均为甲基。The organic compound according to claim 1, characterized in that R 1 and R 2 are both methyl groups.
  8. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自以下化合物组成的组：





    The organic compound according to claim 1, characterized in that the organic compound is selected from the group consisting of the following compounds:





  9. 有机电致发光器件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含权利要求1～8中任一项所述的有机化合物；An organic electroluminescent device, characterized in that it comprises 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 according to any one of claims 1 to 8;
    优选地，所述功能层包含有机发光层，所述有机发光层包含所述有机化合物；Preferably, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound;
    优选地，所述有机电致发光器件为绿色有机电致发光器件。Preferably, the organic electroluminescent device is a green organic electroluminescent device.
  10. 电子装置，其特征在于，包括权利要求9所述的有机电致发光器件。 An electronic device, characterized by comprising the organic electroluminescent device according to claim 9.
PCT/CN2023/120210 2022-10-09 2023-09-20 Organic compound, organic electroluminescent device, and electronic apparatus WO2024078287A1 (en)

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