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WO2022166889A1 - 一种化合物、发光层客体材料、有机电致发光器件和显示装置 - Google Patents

一种化合物、发光层客体材料、有机电致发光器件和显示装置 Download PDF

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WO2022166889A1
WO2022166889A1 PCT/CN2022/075003 CN2022075003W WO2022166889A1 WO 2022166889 A1 WO2022166889 A1 WO 2022166889A1 CN 2022075003 W CN2022075003 W CN 2022075003W WO 2022166889 A1 WO2022166889 A1 WO 2022166889A1
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substituted
unsubstituted
light
compound
emitting layer
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PCT/CN2022/075003
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English (en)
French (fr)
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陈雪波
王储
王娟娟
陈跃
方维海
丰佩川
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北京师范大学
烟台京师材料基因组工程研究院
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Priority to US18/276,166 priority Critical patent/US20240124770A1/en
Publication of WO2022166889A1 publication Critical patent/WO2022166889A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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

Definitions

  • the present application relates to the field of organic light-emitting displays, and in particular, to a compound, a guest material of a light-emitting layer, an organic electroluminescent device and a display device.
  • Organic electroluminescent display devices (hereinafter referred to as OLEDs) have a series of advantages such as self-luminous, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent displays It does not need a backlight, and has a large viewing angle and low power. Its response speed can reach 1,000 times that of an LCD, and its manufacturing cost is lower than that of an LCD with the same resolution. Therefore, organic electroluminescent devices have very broad application prospects. With the continuous advancement of OLED technology in the two fields of lighting and display, organic electroluminescent devices with high efficiency and long life are usually the result of optimized combination of device structure and materials.
  • the light-emitting layer includes a host material and a doped guest material, and the guest material is mainly used to improve the intersystem crossing efficiency between molecular singlet states and triplet states.
  • the light-emitting layer guest materials currently used in OLEDs have poor luminous efficiency and photostability, and the materials have high vapor deposition temperatures, which restrict the display function and development of OLED display devices.
  • the purpose of this application is to provide a compound, which can effectively regulate the emission wavelength of the compound, improve the luminous efficiency and photostability of organic electroluminescence devices, and reduce the evaporation temperature.
  • a first aspect of the present application provides a compound whose structure is shown in formula (I):
  • X-Y is a biaryl bidentate ligand, the coordinating atoms of X and Y are C or N, and X-Y is selected from the subunits of the following compounds or the subunits of the derivatives of the following compounds: 2-(1-naphthyl)benzo oxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, thienylpyridine, phenylpyridine, benzothiophenepyridine, phenylimine, vinylpyridine, arylquinoline, aryliso Quinoline, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, pyridylindazole, phenylimidazole, phenyltriazole, phenylindole, phenylpyrimidine, phenylpyridazine, bipyridine, biphenyl;
  • Z-W is a biaryl bidentate ligand containing a natural heterocycle
  • the coordination atom of Z is C or N
  • Z is selected from the subunits of the following compounds or the subunits of the derivatives of the following compounds: benzene, naphthalene, pyridine, imidazole , pyrrole, tetrahydropyrrole, piperidine, morpholine, quinoline, isoquinoline, pyrimidine, pyrazine, pyridazine, 1,3,4-triazole, tetrazole, oxazole, thiazole;
  • the coordination atom of W is N
  • W is selected from the subunits of the following compounds or the subunits of the derivatives of the following compounds: adenine, guanine, thymine, cytosine, uracil;
  • n is selected from 0, 1, 2.
  • the second aspect of the present application provides the use of the compound provided by the present application as a functional layer material of an organic electroluminescent device.
  • a third aspect of the present application provides a light-emitting layer guest material, which comprises at least one of the compounds provided by the present application.
  • a fourth aspect of the present application provides an organic electroluminescent device, comprising at least one of the light-emitting layer guest materials provided by the present application.
  • a fifth aspect of the present application provides a display device, including the organic electroluminescent device provided by the present application.
  • the compound provided in the present application comprises a structure in which a natural heterocycle is coordinated with iridium (Ir), which can effectively control the emission wavelength of the compound.
  • iridium Ir
  • Using it as the guest material of the light-emitting layer is beneficial to improve the light-emitting efficiency, photostability and service life of the organic electroluminescent device.
  • the display device provided by the present application has excellent display effect.
  • the compound provided by the present application has a small molecular weight, and when it is applied to the light-emitting layer, the evaporation temperature is low, which is favorable for processing.
  • FIG. 1 is a schematic structural diagram of a typical organic electroluminescent device.
  • a first aspect of the present application provides a compound whose structure is shown in formula (I):
  • X-Y is a biaryl bidentate ligand, the coordinating atoms of X and Y are C or N, and X-Y is selected from the subunits of the following compounds or the subunits of the derivatives of the following compounds: 2-(1-naphthyl)benzo oxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, thienylpyridine, phenylpyridine, benzothiophenepyridine, phenylimine, vinylpyridine, arylquinoline, aryliso Quinoline, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, pyridylindazole, phenylimidazole, phenyltriazole, phenylindole, phenylpyrimidine, phenylpyridazine, bipyridine, biphenyl;
  • Z-W is a biaryl bidentate ligand containing a natural heterocycle
  • the coordination atom of Z is C or N
  • Z is selected from the subunits of the following compounds or the subunits of the derivatives of the following compounds: benzene, naphthalene, pyridine, imidazole , pyrrole, tetrahydropyrrole, piperidine, morpholine, quinoline, isoquinoline, pyrimidine, pyrazine, pyridazine, 1,3,4-triazole, tetrazole, oxazole, thiazole;
  • the coordination atom of W is N
  • W is selected from the subunits of the following compounds or the subunits of the following compounds derivatives: adenine, guanine, thymine, cytosine, uracil;
  • n is selected from 0, 1, 2.
  • the compound provided in the present application comprises a structure in which a natural heterocycle is coordinated with iridium (Ir), which can effectively control the emission wavelength of the compound.
  • iridium Ir
  • Using it as the guest material of the light-emitting layer is beneficial to improve the light-emitting efficiency, photostability and service life of the organic electroluminescent device.
  • XY is selected from the subunits of derivatives of the following compounds: 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, thienylpyridine , phenylpyridine, benzothiophenepyridine, phenylimine, vinylpyridine, arylquinoline, arylisoquinoline, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, pyridylindazole, phenylimidazole , phenyltriazole, phenylindole, phenylpyrimidine, phenylpyridazine, bipyridine, biphenyl, the derivatives of the compounds are substituted compounds, and the substituents are independently selected from: halogen, halogenated substituted or unsubstituted C 1 -C 10 alkyl, hal
  • Z is selected from subunits of derivatives of benzene, naphthalene, pyridine, imidazole, pyrrole, tetrahydropyrrole, piperidine, morpholine, quinoline, isoquinoline, pyrimidine, pyrazine, pyridazine, 1 , 3,4-triazole, tetrazole, oxazole, thiazole, the derivatives of the compounds are substituted compounds, and the substituents are independently selected from: hydrogen, deuterium, halogen, unsubstituted or C substituted by Ra 1 -C 10 alkyl, unsubstituted or Ra substituted C 3 -C 10 cycloalkyl, unsubstituted or Ra substituted C 6 -C 14 aryl, unsubstituted or Ra substituted C 2 -C 14 Heteroaryl, unsubstituted or Ra-substituted C 1 -C 10 alkoxy, un
  • W is selected from the subunits of derivatives of the following compounds: adenine, guanine, thymine, cytosine, uracil
  • the derivatives of said compounds are substituted compounds, and the substituents are each independently selected from: hydrogen , deuterium, halogen, unsubstituted or Ra-substituted C 1 -C 10 alkyl, unsubstituted or Ra substituted C 3 -C 10 cycloalkyl, unsubstituted or Ra substituted C 6 -C 14 aryl , unsubstituted or R-substituted C 2 -C 14 heteroaryl, unsubstituted or R-substituted C 1 -C 10 alkoxy, unsubstituted or R-substituted amino;
  • the heteroatom is selected from O, S, N;
  • the substituent Ra of each group is independently selected from deuterium, halogen, nitro, cyano, C 1 -C
  • derivatives of the above-mentioned compounds refer to compounds in which one or more hydrogen atoms in the compounds are substituted by substituents.
  • X-Y is selected from the subunits of the following compounds: 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, thienylpyridine, phenylpyridine , benzothiophene pyridine, phenyl imine, vinyl pyridine, aryl quinoline, aryl isoquinoline, pyridyl naphthalene, pyridyl pyrrole, pyridyl imidazole, pyridyl indazole, phenyl imidazole, phenyl three azole, phenylindole, phenylpyrimidine, phenylpyridazine, bipyridine, biphenyl, 5-methyl-2-phenylpyridine, 5-methyl-2-(2,4-difluorophenyl) Pyridine, 2-(2,4-difluorophenyl)
  • the compound has one of the following general formulas:
  • n 1 -n 4 are each independently selected from 0, 1, and 2.
  • the compound has one of the following general formulas:
  • R a1 -R a4 , R b1 -R b6 , R c1 -R c6 , R d1 -R d4 , R e1 -R e6 , R f1 -R f6 are each independently selected from hydrogen, deuterium, halogen, unsubstituted or Ra substituted C 1 -C 10 alkyl, unsubstituted or Ra substituted C 3 -C 10 cycloalkyl, unsubstituted or Ra substituted C 6 -C 14 aryl, unsubstituted or Ra substituted C 2 -C 14 heteroaryl, unsubstituted or Ra substituted C 1 -C 10 alkoxy, unsubstituted or Ra substituted amino;
  • the heteroatom on the heteroaryl group is selected from O, S, N;
  • the substituents Ra of each group are independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 alkyl, phenyl, biphenyl, terphenyl, naphthyl;
  • n 5 -n 12 are each independently selected from 0, 1, and 2.
  • the compound is selected from the following structures G1-G30:
  • a second aspect of the present application provides a use of the compound provided by the present application as a functional layer material of an organic electroluminescent device.
  • the functional layer of the above organic electroluminescent device may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, etc.
  • the functional layer is a light-emitting layer, and the evaporation temperature of the light-emitting layer is 330°C to 370°C.
  • the compounds provided by the present application have small molecular weights, so the evaporation temperature is low, which is favorable for the processing of the light-emitting layer.
  • a third aspect of the present application provides a light-emitting layer guest material, comprising at least one of the compounds provided by the present application.
  • a fourth aspect of the present application provides an organic electroluminescent device, comprising at least one of the light-emitting layer guest materials provided by the present application.
  • organic electroluminescent device which can be organic electroluminescent devices of various types and structures known in the art, as long as the light-emitting layer guest materials provided in the present application can be used. At least one will do.
  • the organic electroluminescence device of the present application may be a light-emitting device with a top emission structure, and may include an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a transparent or translucent cathode.
  • the organic electroluminescent device of the present application may also be a light-emitting device with a bottom-emitting structure, which may include a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, Electron injection layer and cathode structure.
  • the organic electroluminescent device of the present application may also be a light-emitting device with a double-sided light-emitting structure, which may include a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the substrate in this order. , electron injection layer and transparent or semi-transparent cathode structure.
  • an electron blocking layer is provided between the hole transport layer and the light emitting layer.
  • a hole blocking layer is provided between the light emitting layer and the electron transport layer.
  • a light extraction layer is arranged on the transparent electrode on the light emitting side.
  • the structure of the organic electroluminescence device of the present application is not limited to the above-mentioned specific structure, and the above-mentioned layers may be omitted or simultaneously provided if necessary.
  • an organic electroluminescent device may include an anode made of metal, a hole injection layer (5 nm to 20 nm), a hole transport layer (80 nm to 140 nm), an electron blocking layer (5 nm to 20 nm), a light emitting layer on a substrate in this order layer (20 nm to 45 nm), hole blocking layer (5 nm to 20 nm), electron transport layer (30 nm to 40 nm), electron injection layer (0.3 nm to 1 nm), transparent or semitransparent cathode and light extraction layer structure.
  • Fig. 1 shows a schematic diagram of a typical organic electroluminescent device, wherein, from bottom to top, a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, and an electron blocking layer 5 are arranged in order. , light-emitting layer 6 , hole blocking layer 7 , electron transport layer 8 , cathode electrode 9 .
  • FIG. 1 only schematically shows the structure of a typical organic electroluminescence device, the present application is not limited to this structure, and the guest material of the light-emitting layer of the present application can be used for any type of organic electroluminescence device.
  • the organic electroluminescent device may further include an electron injection layer, a light extraction layer, etc. In practical applications, these layers may be added or omitted according to specific conditions.
  • organic electroluminescent device of the present application will be described below with reference to FIG. 1 , but this does not imply any limitation on the protection scope of the present application. It can be understood that all organic electroluminescent devices that can use the guest material of the light-emitting layer of the present application fall within the protection scope of the present application.
  • the material of the substrate 1 is not particularly limited, and conventional substrates used for organic electroluminescent devices in the prior art can be used, such as glass, polymer materials, glass with TFT components and polymer materials Wait.
  • the material of the reflective anode electrode 2 is not particularly limited, and can be selected from the known indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), oxide Transparent conductive materials such as zinc (ZnO) and low temperature polysilicon (LTPS), or metal materials such as silver and its alloys, aluminum and its alloys, or organic conductive materials such as poly-3,4-ethylenedioxythiophene (PEDOT) , or the reflective anode is a multi-layer structure formed of the above-mentioned materials.
  • the number of layers of the multi-layer structure is not particularly limited in this application, and can be selected according to actual needs, as long as it can meet the purpose of the application, for example, 1 layer, 2 layers layer, 3 or more layers.
  • the material of the hole injection layer 3 is not particularly limited, and a hole injection layer material known in the art can be used, for example, a hole transport material (HTM) is selected as the hole injection material.
  • HTM hole transport material
  • the hole injection layer 3 may further include p-type dopants, and the types of the p-type dopants are not particularly limited, and various p-type dopants known in the art can be used, such as The following p-type dopants can be used:
  • the amount of the p-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
  • the material of the hole transport layer 4 is not particularly limited, and can be made of hole transport material (HTM) known in the art.
  • HTM hole transport material
  • the number of the hole transport layer 4 is not particularly limited, and can be adjusted according to actual needs, as long as it can meet the purpose of the present application, for example, 1 layer, 2 layers, 3 layers, 4 layers or more.
  • the material for the hole injection layer and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-34 compounds:
  • the material of the electron blocking layer 5 is not particularly limited, and electron blocking layer materials known in the art can be used, for example, at least one of the compounds from EB-01 to EB-05 can be selected:
  • the materials of the light-emitting layer 6 include light-emitting layer host material and light-emitting layer guest material, wherein the amount of light-emitting layer host material and light-emitting layer guest material is not particularly limited, and can be the amount known to those skilled in the art.
  • the light-emitting layer host material may be selected from at least one of the following RH-1 to RH-11 compounds:
  • the light-emitting layer guest material may include at least one of the light-emitting layer guest materials of the present application, or at least one of the light-emitting layer guest materials of the present application and the following known light-emitting layer guest materials A combination of at least one of.
  • the known light-emitting layer guest material may be selected from at least one of the following RPD-1 to RPD-28 compounds:
  • the material of the hole blocking layer 7 is not particularly limited, and a hole blocking layer material known in the art can be used, for example, at least one of the following HB-01 to HB-05 compounds can be selected :
  • the material of the electron transport layer 8 is not particularly limited, and electron transport layer materials known in the art can be used, for example, at least one of the following ET-1 to ET-59 compounds can be selected:
  • the electron transport layer 8 may also include n-type dopants, and the types of the n-type dopants are not particularly limited, and various n-type dopants known in the art can be used, for example, The following n-type dopants were used:
  • the amount of the n-type dopant is not particularly limited, and may be the amount known to those skilled in the art.
  • the material of the cathode electrode 9 is not particularly limited, and can be selected from, but not limited to, magnesium-silver mixture, magnesium-aluminum mixture, LiF/Al, ITO, Al and other metals, metal mixtures, oxides, and the like.
  • a fifth aspect of the present application provides a display device, comprising the organic electroluminescent device provided by the present application, and having excellent display effects.
  • the display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
  • the method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art can be used.
  • the organic electroluminescent device can be prepared by the following preparation method:
  • a cathode material was vacuum-evaporated on the electron transport layer 8 as the cathode electrode 9 .
  • the light-emitting layer guest material of the present application can be used in an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any preparation method known in the art.
  • the synthesis method of the compounds of the present application is not particularly limited, and any method known to those skilled in the art can be used for synthesis.
  • the following examples illustrate the synthesis process of the compounds of the present application.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 16.7 g of 6-(pyridine) -2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 30%.
  • the aqueous phase was extracted with toluene, the organic phases were combined, washed with ice water until nearly neutral, and dried with anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 14.11 g of 3-oxo-3-(pyridin-2-yl)propionic acid. Ethyl ester, light brown transparent liquid, yield 73%.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 16.7 g of 6-(pyridine) -2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 30%.
  • the reaction was quenched with 300 mL of water, the aqueous and organic phases were separated, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 31.8 g of 2-phenylpyridine, which was a pale yellow transparent liquid with a yield of 81 %, the purity is 99.05%.
  • the reaction was quenched with 40 mL of glacial acetic acid and 120 mL of ice water, and the aqueous phase and the organic phase were separated.
  • the aqueous phase was extracted with toluene, the organic phases were combined, washed with ice water until nearly neutral, and dried with anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 14.11 g of 3-oxo-3-(pyridin-2-yl)propionic acid. Ethyl ester, light brown transparent liquid, yield 73%.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 16.7 g of 6-(pyridine) -2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 30%.
  • the reaction was quenched with 300 mL of water, the aqueous and organic phases were separated, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1) to obtain 34.5 g of 5-methyl-2-phenylpyridine, which was a pale yellow transparent liquid , the yield is 80.5%.
  • the aqueous phase was extracted with toluene, the organic phases were combined, washed with ice water until nearly neutral, and dried with anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 14.11 g of 3-oxo-3-(pyridin-2-yl)propionic acid. Ethyl ester, light brown transparent liquid, yield 73%.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 16.7 g of 6-(pyridine) -2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 30%.
  • silica gel column chromatography was used for separation (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 6:1) to obtain 12.38g of 2-methyl-3-oxo -3-(pyridin-2-yl)propionic acid ethyl ester, light brown transparent liquid, yield 60%.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether in turn, and dried in vacuo to obtain 18 g of 5-methyl- 6-(Pyridin-2-yl)-2-thio-4(1H,3H)-pyrimidinone, white powdery solid, yield 30%.
  • the reaction was quenched with 300 mL of water, the aqueous and organic phases were separated, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 31.8 g of 2-phenylpyridine, which was a pale yellow transparent liquid with a yield of 81 %, the purity is 99.05%.
  • the aqueous phase was extracted with toluene, the organic phases were combined, washed with ice water until nearly neutral, and dried with anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 20:1) to obtain 15.75 g of 3-oxo-3-(quinolin-2-yl)propane Ethyl acid as a white solid in 65% yield.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 24.5g of 6-(quinoline) Lin-2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 35%.
  • the reaction was quenched with 300 mL of water, the aqueous and organic phases were separated, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 31.8 g of 2-phenylpyridine, which was a pale yellow transparent liquid with a yield of 81 %, the purity is 99.05%.
  • the aqueous phase was extracted with toluene, the organic phases were combined, washed with ice water until nearly neutral, and dried with anhydrous sodium sulfate.
  • the solvent was evaporated under reduced pressure and separated by silica gel column chromatography (using a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1) to obtain 14.11 g of 3-oxo-3-(pyridin-2-yl)propionic acid. Ethyl ester, light brown transparent liquid, yield 73%.
  • reaction solvent was evaporated under reduced pressure, water was added until the residue was completely dissolved, the pH was adjusted to 6-8 with 2M hydrochloric acid until the precipitation was complete, filtered under reduced pressure, the filter residue was washed with water and petroleum ether successively, and dried in vacuo to obtain 16.7 g of 6-(pyridine) -2-yl)-2-thio-4(1H,3H)-pyrimidinone as a white powdery solid with a yield of 30%.
  • the glass plate coated with a transparent conductive layer of indium tin oxide (ITO) with a thickness of 130 nm was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreasing in an acetone-ethanol mixed solvent, and baked in a clean environment. Bake until moisture is completely removed, rinse with UV light and ozone, and bombard the surface with a low-energy cation beam;
  • ITO indium tin oxide
  • the above-mentioned glass substrate with anode is placed in a vacuum chamber, and the vacuum is evacuated to less than 10 -5 torr, and a hole injection layer is vacuum-evaporated on the above-mentioned anode layer film.
  • the material of the hole injection layer includes hole injection Layer material HT-34 and p-type dopant p-1 are evaporated by multi-source co-evaporation, and the evaporation rate of hole injection layer material HT-34 is adjusted to 0.1nm/s, p-type dopant
  • the vapor deposition rate of p-1 is 3% of the vapor deposition rate of the hole injection layer material HT-34, and the total vapor deposition film thickness is 10 nm;
  • the hole transport layer material HT-34 was vacuum evaporated on the hole injection layer as the hole transport layer, the evaporation rate was 0.1nm/s, and the evaporation film thickness was 112nm;
  • the electron blocking layer material EB-05 was vacuum evaporated on the hole transport layer as the electron blocking layer, the evaporation rate was 0.1 nm/s, and the evaporation film thickness was 10 nm;
  • the light-emitting layer includes the host material RH-11 and the guest material G1 provided in this application.
  • the mass ratio of the host material RH-11 and the guest material G1 is 97:3.
  • the method of source co-evaporation is used for evaporation, and the evaporation rate of the host material is adjusted to be 0.1 nm/s, the evaporation rate of the guest material is 3% of the evaporation rate of the host material RH-11, and the total film thickness of the evaporation is 20 nm;
  • the hole blocking layer material HB-05 was vacuum evaporated on the light-emitting layer as the hole blocking layer, the evaporation rate was 0.1 nm/s, and the evaporation film thickness was 5 nm;
  • an electron transport layer is vacuum-evaporated on the hole blocking layer, and the materials of the electron transport layer include electron transport material ET-43 and n-type dopant n-1, electron transport material ET-43 and n-type dopant
  • the mass ratio of n-1 is 1:1, the multi-source co-evaporation method is used for evaporation, the evaporation rate of electron transport material ET-43 is adjusted to 0.1 nm/s, and the evaporation of n-type dopant n-1 The rate is 3% of the evaporation rate of electron transport material ET-43, and the total film thickness of evaporation is 35nm;
  • the cathode material was a mixture of magnesium and aluminum, and the mass ratio of magnesium and aluminum was 1:9.
  • the voltage is increased at a rate of 0.1V per second.
  • Measure the voltage when the brightness of the organic electroluminescent device reaches 6000nit, that is, the driving voltage, and measure the current density at this time; the ratio of brightness to current density is the current efficiency; the life test of LT95 is as follows: use a brightness meter at 6000nit Under the brightness, maintaining a constant current, measure the time for the brightness of the organic electroluminescent device to drop to 5700cd/ m2 , in hours.
  • the organic electroluminescence devices prepared in Examples 1 to 13 are the compounds G1, G2, G3, G8, G9, G10, G12, G14, G19, G21, G22, G23 and G27 are used in the light-emitting layer as guest materials in the light-emitting layer.
  • the driving of the device Lower voltage, higher current efficiency and longer LT95 life.
  • the compound of the present application as a guest material of the light-emitting layer of an organic electroluminescent device can effectively regulate the light-emitting wavelength, improve the light-emitting efficiency, and prolong the life of the device.
  • the compound provided in the present application as a guest material of the light-emitting layer to prepare the light-emitting layer, the evaporation temperature of the light-emitting layer is lower, which is beneficial to the processing of the organic electroluminescent device.

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Abstract

本申请提供了一种通式(I)的化合物，其可以用于有机电致发光器件，作为发光层客体材料。该化合物包含天然杂环与铱(Ir)配位的结构，能够有效调控化合物的发光波长。将其用作发光层的客体材料，则有利于提高有机电致发光器件的发光效率和光稳定性。此外，本申请提供的化合物，分子量小，将其应用于发光层，蒸镀温度较低，有利于加工。本申请还提供了一种包含通式(I)化合物的发光层客体材料、有机电致发光器件和显示装置。

Description

一种化合物、发光层客体材料、有机电致发光器件和显示装置
本申请要求于2021年2月8日提交中国专利局、申请号为202110183618.6发明名称为“一种化合物、发光层客体材料、有机电致发光器件和显示装置”的中国专利申请的优先权，其全部内容通过引用结合在本申请中。
技术领域
本申请涉及有机发光显示领域，特别是涉及一种化合物、发光层客体材料、有机电致发光器件和显示装置。
背景技术
有机电致发光显示器件(以下简称OLED)具有自主发光、低电压直流驱动、全固化、视角宽、重量轻、组成和工艺简单等一系列的优点，与液晶显示器相比，有机电致发光显示器不需要背光源，且视角大、功率低，其响应速度可达液晶显示器的1000倍，制造成本却低于同等分辨率的液晶显示器。因此，有机电致发光器件具有十分广阔的应用前景。随着OLED技术在照明和显示两大领域的不断推进，效率高且寿命长的有机电致发光器件通常是器件结构和材料优化搭配的结果。其中，发光层中包含主体材料和掺杂的客体材料，客体材料主要用于提高分子单重态、三重态之间的系间窜越效率。但目前应用于OLED中的发光层客体材料的发光效率和光稳定性较差，且材料的蒸镀温度高，制约了OLED显示装置的显示功能和发展。
发明内容
本申请的目的在于提供一种化合物，能够有效调控化合物的发光波长，提高有机电致发光器件的发光效率和光稳定性，降低蒸镀温度。
本申请的第一个方面提供一种化合物，其结构如式(Ⅰ)所示：
Figure PCTCN2022075003-appb-000001
其中，
X-Y为双芳基双齿配体，X和Y的配位原子为C或N，X-Y选自以下化合物的亚基或以下化合物的衍生物的亚基：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、 噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯；
Z-W为含有天然杂环的双芳基双齿配体，Z的配位原子为C或N，Z选自以下化合物的亚基或以下化合物的衍生物的亚基：苯、萘、吡啶、咪唑、吡咯、四氢吡咯、哌啶、吗啉、喹啉、异喹啉、嘧啶、吡嗪、哒嗪、1,3,4-三唑、四唑、噁唑、噻唑；W的配位原子为N，W选自以下化合物的亚基或以下化合物的衍生物的亚基：腺嘌呤、鸟嘌呤、胸腺嘧啶、胞嘧啶、尿嘧啶；
n选自0、1、2。
本申请第二个方面提供本申请提供的化合物用作有机电致发光器件的功能层材料的用途。
本申请第三个方面提供一种发光层客体材料，其包含本申请提供的化合物中的至少一种。
本申请第四个方面提供了一种有机电致发光器件，包含本申请提供的发光层客体材料中的至少一种。
本申请第五个方面提供了一种显示装置，包含本申请提供的有机电致发光器件。
本申请提供的化合物，包含天然杂环与铱(Ir)配位的结构，能够有效调控化合物的发光波长。将其用作发光层的客体材料，则有利于提高有机电致发光器件的发光效率、光稳定性和使用寿命。本申请提供的显示装置具有优良的显示效果。此外，本申请提供的化合物，分子量小，将其应用于发光层，蒸镀温度较低，有利于加工。
当然，实施本申请的任一产品或方法并不一定需要同时达到以上所述的所有优点。
附图说明
为了更清楚地说明本申请的技术方案，下面对实施例中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本申请的一些实施例。
图1为一种典型的有机电致发光器件的结构示意图。
具体实施方式
为使本申请的目的、技术方案、及优点更加清楚明白，以下参照附图和实施例，对本申请进一步详细说明。显然，所描述的实施例仅仅是本申请一部分实施例，而不是全部的实施例。基于本申请中的实施例，本领域普通技术人员所获得的所有其他技术方案，都属 于本申请保护的范围。
本申请的第一个方面提供一种化合物，其结构如式(I)所示：
Figure PCTCN2022075003-appb-000002
其中，
X-Y为双芳基双齿配体，X和Y的配位原子为C或N，X-Y选自以下化合物的亚基或以下化合物的衍生物的亚基：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯；
Z-W为含有天然杂环的双芳基双齿配体，Z的配位原子为C或N，Z选自以下化合物的亚基或以下化合物的衍生物的亚基：苯、萘、吡啶、咪唑、吡咯、四氢吡咯、哌啶、吗啉、喹啉、异喹啉、嘧啶、吡嗪、哒嗪、1,3,4-三唑、四唑、噁唑、噻唑；W的配位原子为N，W选自以下化合物的亚基或以下化合物衍生物的的亚基：腺嘌呤、鸟嘌呤、胸腺嘧啶、胞嘧啶、尿嘧啶；
n选自0、1、2。
本申请提供的化合物，包含天然杂环与铱(Ir)配位的结构，能够有效调控化合物的发光波长。将其用作发光层的客体材料，则有利于提高有机电致发光器件的发光效率、光稳定性和使用寿命。
优选地，当X-Y选自以下化合物的衍生物的亚基时：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯，所述化合物的衍生物为被取代的化合物，取代基各自独立地选自：卤素、被卤素取代或未取代的C 1-C 10烷基、被卤素取代或未取代的C 6-C 14芳基、被卤素取代或未取代的C 6-C 14芳基烷氧基；
当Z选自以下化合物的衍生物的亚基时：苯、萘、吡啶、咪唑、吡咯、四氢吡咯、哌啶、吗啉、喹啉、异喹啉、嘧啶、吡嗪、哒嗪、1,3,4-三唑、四唑、噁唑、噻唑，所述化合 物的衍生物为被取代的化合物，取代基各自独立地选自：氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；所述杂芳基上的杂原子选自O、S、N；各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基；
当W选自以下化合物的衍生物的亚基时：腺嘌呤、鸟嘌呤、胸腺嘧啶、胞嘧啶、尿嘧啶，所述化合物的衍生物为被取代的化合物，取代基各自独立地选自：氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；所述杂芳基上的杂原子选自O、S、N；各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基。
在本申请中，上述化合物的衍生物是指化合物中的一个或多个氢原子被取代基取代的化合物。
进一步优选地，X-Y选自以下化合物的亚基：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯、5-甲基-2-苯基吡啶、5-甲基-2-(2,4-二氟苯基)吡啶、2-(2,4-二氟苯基)-5-三氟甲基吡啶、2-(2,4-二氟苯基)嘧啶、2-(3,4-二氟苯基)-1-(2,4,6-三甲基苯基)咪唑、1,3-二甲基-5-(3-氟苯基)三唑、1-(3,5-二甲基苯基)异喹啉、6-异丙基-1-(3,5-二甲基苯基)异喹啉、2-(3,5-二甲基苯基)喹啉、4-甲基-2-(3,5-二甲基苯基)喹啉、2’,4’-二氟-2,3’-联吡啶、1-甲基-3-(4-甲基苯基)-2,3-二氢咪唑、6-苯基-3-(2,4,6-三甲基苯氧基)哒嗪、1-(4-仲丁基苯基)异喹啉、3-异丙基-2-(3-甲基苯基)喹啉、5-甲基-2-(3,5-二甲基苯基)吡啶。
优选地，所述化合物具有以下通式中的一种：
Figure PCTCN2022075003-appb-000003
其中，n 1-n 4各自独立地选自0、1、2。
更优选地，所述化合物具有以下通式中的一种：
Figure PCTCN2022075003-appb-000004
其中，
R a1-R a4、R b1-R b6、R c1-R c6、R d1-R d4、R e1-R e6、R f1-R f6各自独立地选自氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；
所述杂芳基上的杂原子选自O、S、N；
各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基；
n 5-n 12各自独立地选自0、1、2。
例如，所述化合物选自下述结构G1-G30：
Figure PCTCN2022075003-appb-000005
Figure PCTCN2022075003-appb-000006
本申请第二个方面提供一种将本申请提供的化合物用作有机电致发光器件的功能层材料的用途。
在本申请中，上述有机电致发光器件的功能层可以包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层和电子注入层等，优选地，所述功能层为发光层，所述发光层的蒸镀温度为330℃至370℃。本申请提供的化合物，分子量小，因此蒸镀温度低，有利于发光层的加工。
本申请第三个方面提供一种发光层客体材料，包含本申请提供的化合物中的至少一种。
本申请第四个方面提供一种有机电致发光器件，包含本申请提供的发光层客体材料中的至少一种。
在本申请中，对于有机电致发光器件的种类和结构没有特别限制，可以为本领域公知的各种类型和结构的有机电致发光器件，只要可以使用本申请提供的发光层客体材料中的至少一种即可。
本申请的有机电致发光器件，可以是顶部发光结构的发光器件，可以举出在基板上依次包含阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、透明或半透明阴极。
本申请的有机电致发光器件，还可以是底部发光结构的发光器件，可以举出在基板上依次包含透明或半透明阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层及阴极结构。
本申请的有机电致发光器件，还可以是双侧发光结构的发光器件，可以举出在基板上依次包含透明或半透明阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入 层及透明或半透明阴极结构。
另外，在空穴传输层与发光层之间具有电子阻挡层。在发光层与电子传输层之间具有空穴阻挡层。在出光侧的透明电极上设置光提取层。然而本申请的有机电致发光器件的结构并不限于上述具体结构，如果需要，可以省略或同时具有上述的层。例如，有机电致发光器件可以在基板上依次包含由金属制成的阳极、空穴注入层(5nm至20nm)、空穴传输层(80nm至140nm)、电子阻挡层(5nm至20nm)、发光层(20nm至45nm)、空穴阻挡层(5nm至20nm)、电子传输层(30nm至40nm)、电子注入层(0.3nm至1nm)、透明或半透明阴极以及光提取层结构。
图1示出了一种典型的有机电致发光器件的示意图，其中，从下到上，依次设置基板1、反射阳极电极2、空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子传输层8、阴极电极9。
可以理解，图1仅示意性地示出了一种典型的有机电致发光器件的结构，本申请并不限于这种结构，本申请的发光层客体材料可以用于任何类型的有机电致发光器件。例如，有机电致发光器件还可以包括电子注入层、光提取层等，实际应用时，可以根据具体情况增加或省略这些层。
为了方便起见，以下参照图1对本申请的有机电致发光器件进行说明，但这不意味着对本申请的保护范围的任何限定。可以理解，所有能够使用本申请的发光层客体材料的有机电致发光器件都在本申请的保护范围内。
在本申请中，所述基板1的材料没有特别限制，可以使用现有技术中有机电致发光器件所用的常规基板，例如，玻璃、聚合物材料、带有TFT元器件的玻璃和聚合物材料等。
在本申请中，所述反射阳极电极2的材料没有特别限制，可以选自现有技术中已知的铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO 2)、氧化锌(ZnO)、低温多晶硅(LTPS)等透明导电材料，也可以是银及其合金、铝及其合金等金属材料，或者使用聚3,4-乙撑二氧噻吩(PEDOT)等有机导电材料，或者反射阳电极是由上述材料形成的多层结构，本申请对多层结构的层数没有特别限制，可以根据实际需要进行选择，只要能满足本申请目的即可，例如，1层、2层、3层或更多层。
在本申请中，所述空穴注入层3的材料没有特别限制，可以使用本领域已知的空穴注入层材料，例如选用空穴传输材料(HTM)作为空穴注入材料。
在本申请中，所述空穴注入层3还可以包括p型掺杂剂，所述p型掺杂剂的种类没有特别限制，可以使用本领域已知的各种p型掺杂剂，例如可以采用以下p型掺杂剂：
Figure PCTCN2022075003-appb-000007
在本申请中，所述p型掺杂剂用量没有特别限制，可以为本领域技术人员公知的用量。
在本申请中，所述空穴传输层4的材料没有特别限制，可以使用本领域已知的空穴传输材料(HTM)制成。所述空穴传输层4的层数没有特别限定，可以根据实际需要进行调节，只要能满足本申请目的即可，例如，1层、2层、3层、4层或更多层。例如用于空穴注入层的材料和用于空穴传输层的材料可以选自以下HT-1至HT-34化合物中的至少一种：
Figure PCTCN2022075003-appb-000008
Figure PCTCN2022075003-appb-000009
在本申请中，所述电子阻挡层5的材料没有特别限制，可以使用本领域已知的电子阻挡层材料，例如可以选自EB-01至EB-05化合物中的至少一种：
Figure PCTCN2022075003-appb-000010
在本申请中，所述发光层6的材料包含发光层主体材料和发光层客体材料，其中，发光层主体材料与发光层客体材料的用量没有特别限制，可以为本领域技术人员公知的用量。
例如，发光层主体材料可以选自以下RH-1至RH-11化合物中的至少一种：
Figure PCTCN2022075003-appb-000011
在本申请中，所述发光层客体材料可以包含本申请的发光层客体材料中的至少一种，也可以包含本申请的发光层客体材料中的至少一种与以下已知的发光层客体材料中的至少一种的组合。
例如，已知的发光层客体材料可以选自以下RPD-1至RPD-28化合物中的至少一种：
Figure PCTCN2022075003-appb-000012
在本申请中，所述空穴阻挡层7的材料没有特别限制，可以使用本领域已知的空穴阻挡层材料，例如，可以选自以下HB-01至HB-05化合物中的至少一种：
Figure PCTCN2022075003-appb-000013
在本申请中，所述电子传输层8的材料没有特别限制，可以使用本领域已知的电子传输层材料，例如，可以选自以下ET-1至ET-59化合物中的至少一种：
Figure PCTCN2022075003-appb-000014
Figure PCTCN2022075003-appb-000015
Figure PCTCN2022075003-appb-000016
在本申请中，所述电子传输层8还可以包括n型掺杂剂，所述n型掺杂剂的种类没有特别限制，可以采用本领域已知的各种n型掺杂剂，例如可以采用以下n型掺杂剂：
Figure PCTCN2022075003-appb-000017
在本申请中，所述n型掺杂剂用量没有特别限制，可以为本领域技术人员公知的用量。
在本申请中，所述阴极电极9的材料没有特别限制，可以选自但不限于镁银混合物、镁铝混合物、LiF/Al、ITO、Al等金属、金属混合物、氧化物等。
本申请第五个方面提供一种显示装置，包含本申请提供的有机电致发光器件，具有优良的显示效果。所述显示装置包括但不限于显示器、电视、移动通信终端、平板电脑等。
制备本申请的有机电致发光器件的方法没有特别限制，可以采用本领域公知的任何方法，例如，有机电致发光器件可以采用如下制备方法制备：
(1)清洗顶发光用OLED器件基板1上的反射阳极电极2，在清洗机中分别通过药洗、水洗、毛刷、高压水洗、风刀等步骤，然后再加热处理；
(2)在反射阳极电极2上真空蒸镀空穴注入材料作为空穴注入层3；
(3)在空穴注入层3上真空蒸镀空穴传输材料作为空穴传输层4；
(4)在空穴传输层4上真空蒸镀电子阻挡层材料作为电子阻挡层5；
(5)在电子阻挡层5上真空蒸镀发光层6，发光层6中包含主体材料和客体材料；
(6)在发光层6上真空蒸镀空穴阻挡层材料作为空穴阻挡层7；
(7)在空穴阻挡层7上真空蒸镀电子传输材料作为电子传输层8；
(8)在电子传输层8上真空蒸镀阴极材料作为阴极电极9。
以上仅描述一种典型的有机电致发光器件的结构及其制备方法，应当理解，本申请并不限于这种结构。本申请的发光层客体材料可以用于任何结构的有机电致发光器件，并且可以采用本领域公知的任何制备方法制备所述有机电致发光器件。
本申请化合物的合成方法没有特别限制，可以采用本领域技术人员公知的任何方法进行合成。以下举例说明本申请化合物的合成过程。
合成实施例
合成实施例1：化合物G1的合成
Figure PCTCN2022075003-appb-000018
(1)配体6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至115℃回流。将12.064g的2-乙酰吡啶(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应5h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到14.11g的3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为73％。其中，结构式中的Et代表乙基。
1H NMR(600MHz,CDCl 3)δ7.58(d,J＝0.9Hz,1H),7.24(d,J＝3.6Hz,1H),6.54(dd,J 1＝3.6Hz,J 2＝1.6Hz,1H),4.17(q,J＝7.2Hz,2H),3.81(s,2H),1.22(s,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入53g的3-氧代-3-(吡啶-2-基)丙酸乙酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到16.7g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.70(s,1H),11.34(s,1H),8.75(s,1H),8.17(s,1H),8.01(s,1H),7.62(s,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加 入15g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到6.13g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为44.4％，纯度为98.21％。
1H NMR(400MHz,DMSO-d 6)δ11.23(s,1H),10.60(s,1H),8.72(s,1H),8.11(s,1H),7.99(s,1H),7.57(s,1H),6.33(s,1H).
(2)化合物G1的合成
a)在250mL三口瓶中加入60mL乙二醇单甲醚和20mL水，通入氮气鼓泡30min，氮气保护下依次加入2.15g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(11.36mmol)和1g三水合三氯化铱(2.84mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到1.4g的铱复合物二聚体，为暗红色固体，产率为82％。
b)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入362.4mg的铱复合物二聚体(0.3mmol)、227mg的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应12h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到317.8mg的复合物G1，为亮红色固体，收率70％。
1H NMR(600MHz,CDCl 3)δ9.97(s,3H),8.63(m,3H),7.42(m,6H),7.24(m,3H),6.60(m,3H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 27H 19O 6N 9 758.109,found 758.138.
合成实施例2：化合物G2的合成
Figure PCTCN2022075003-appb-000019
(1)配体6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至115℃回流。将12.064g的2-乙酰吡啶(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应5h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到14.11g的3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为73％。
1H NMR(600MHz,CDCl 3)δ7.58(d,J＝0.9Hz,1H),7.24(d,J＝3.6Hz,1H),6.54(dd,J 1＝3.6Hz,J 2＝1.6Hz,1H),4.17(q,J＝7.2Hz,2H),3.81(s,2H),1.22(s,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入53g的3-氧代-3-(吡啶-2-基)丙酸乙酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到16.7g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.70(s,1H),11.34(s,1H),8.75(s,1H),8.17(s,1H),8.01(s,1H),7.62(s,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入15g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到6.13g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为44.4％，纯度为98.21％。
1H NMR(400MHz,DMSO-d 6)δ11.23(s,1H),10.60(s,1H),8.72(s,1H),8.11(s,1H),7.99(s,1H),7.57(s,1H),6.33(s,1H).
(2)化合物G2的合成
a)在2000mL三口瓶中加入630mL甲苯、473mL水和126mL乙醇，通入氮气鼓泡30min，氮气保护下依次加入105g碳酸钾(759mmol)，8.5g的四三苯基膦钯(7.34mmol)，40g的2-溴吡啶(253mmol)，37.1g苯硼酸(304mmol)，加热至105℃回流，反应12h。用300mL水淬灭反应，分离水相和有机相，水相用乙酸乙酯萃取，合并有机相，并用无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合 液)，得到31.8g的2-苯基吡啶，为淡黄色透明液体，收率为81％，纯度为99.05％。
1H NMR(400MHz,CDCl 3)δ8.70(m,1H),8.00(m,2H),7.75(m,2H),7.45(m,3H),7.25(m,1H).
b)在250mL三口瓶中加入60mL乙二醇单甲醚和20mL水，通入氮气鼓泡30min，氮气保护下依次加入1.76g的2-苯基吡啶(11.36mmol)和1g三水合三氯化铱(2.84mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到1.28g的铱复合物二聚体，为黄色固体，产率为84％。
c)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入321.6mg的铱复合物二聚体(0.3mmol)、227mg的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应12h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到300mg的复合物G2，为橙黄色固体，收率73％。
1H NMR(600MHz,CDCl 3)δ8.46(d,J＝6.4Hz,1H),8.02(d,J＝7.8Hz,1H),7.86(m,6H),7.69(m,2H),7.62(m,2H),7.35(d,J＝6.1Hz,1H),7.07(t,J＝6.6Hz,1H),6.96(t,J＝8.0Hz,1H),6.83(m,4H),6.28(m,2H),6.22(d,J＝7.6Hz,1H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 31H 23O 2N 5 690.148,found 690.215.
合成实施例3：化合物G3的合成
Figure PCTCN2022075003-appb-000020
(1)配体6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1 g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至115℃回流。将12.064g的2-乙酰吡啶(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应5h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到14.11g的3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为73％。
1H NMR(600MHz,CDCl 3)δ7.58(d,J＝0.9Hz,1H),7.24(d,J＝3.6Hz,1H),6.54(dd,J 1＝3.6Hz,J 2＝1.6Hz,1H),4.17(q,J＝7.2Hz,2H),3.81(s,2H),1.22(s,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入53g的3-氧代-3-(吡啶-2-基)丙酸乙酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到16.7g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.70(s,1H),11.34(s,1H),8.75(s,1H),8.17(s,1H),8.01(s,1H),7.62(s,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入15g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到6.13g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为44.4％，纯度为98.21％。
1H NMR(400MHz,DMSO-d 6)δ11.23(s,1H),10.60(s,1H),8.72(s,1H),8.11(s,1H),7.99(s,1H),7.57(s,1H),6.33(s,1H).
(2)化合物G3的合成
a)在2000mL三口瓶中加入630mL甲苯、473mL水和126mL乙醇，通入氮气鼓泡30min，氮气保护下依次加入105g碳酸钾(759mmol)，8.5g的四三苯基膦钯(7.34mmol)，43.5g的5-甲基-2-溴吡啶(253mmol)，37.1g苯硼酸(304mmol)，加热至105℃回流，反应12h。用300mL水淬灭反应，分离水相和有机相，水相用乙酸乙酯萃取，合并有机相，并用无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到34.5g的5-甲基-2-苯基吡啶，为淡黄色透明液体，收率为80.5％。
1H NMR(400MHz,CDCl 3)δ8.70(m,1H),8.00(m,2H),7.75(m,2H),7.45(m,3H),7.25 (m,1H).
b)在100mL三口瓶中加入30mL乙二醇单甲醚和10mL水，通入氮气鼓泡30min，氮气保护下依次加入959.5mg的5-甲基-2-苯基吡啶(5.67mmol)和0.5g三水合三氯化铱(1.42mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到0.66g的铱复合物二聚体，为黄色固体，产率为82.4％。
c)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入338.5mg的铱复合物二聚体(0.3mmol)、227mg的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应12h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为30:1的混合液)，得到300mg的复合物G3，为黄色固体，收率69.8％。
1H NMR(600MHz,CDCl 3)δ8.21(s,1H),8.03(d,J＝8.7Hz,1H),7.88(m,2H),7.78(d,J＝8.3Hz,1H),7.74(m,2H),7.57(d,J＝7.9Hz,2H),7.50(t,J＝10.4Hz,2H),7.24(m,1H),7.12(s,1H),6.94(t,J＝7.7Hz,1H),6.81(m,3H),6.29(m,1H),6.23(m,2H),2.28(s,3H),2.15(s,3H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 33H 27O 2N 5 718.179,found 717.939.
合成实施例4：化合物G12的合成
Figure PCTCN2022075003-appb-000021
(1)配体6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至 115℃回流。将12.064g的2-乙酰吡啶(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应5h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到14.11g的3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为73％。
1H NMR(600MHz,CDCl 3)δ7.58(d,J＝0.9Hz,1H),7.24(d,J＝3.6Hz,1H),6.54(dd,J 1＝3.6Hz,J 2＝1.6Hz,1H),4.17(q,J＝7.2Hz,2H),3.81(s,2H),1.22(s,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入53g的3-氧代-3-(吡啶-2-基)丙酸乙酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到16.7g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.70(s,1H),11.34(s,1H),8.75(s,1H),8.17(s,1H),8.01(s,1H),7.62(s,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入15g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到6.13g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为44.4％，纯度为98.21％。
1H NMR(400MHz,DMSO-d 6)δ11.23(s,1H),10.60(s,1H),8.72(s,1H),8.11(s,1H),7.99(s,1H),7.57(s,1H),6.33(s,1H).
(2)化合物G12的合成
a)在100mL三口瓶中加入30mL乙二醇单甲醚和10mL水，通入氮气鼓泡30min，氮气保护下依次加入1.4g的4-甲基-2-(3,5-二甲基苯基)喹啉(5.67mmol)和0.5g三水合三氯化铱(1.42mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水、乙醇、石油醚洗涤，真空干燥，得到0.74g的铱复合物二聚体，为红色固体，产率为73％。
b)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入360.2mg的铱复合物二聚体(0.25mmol)、189.2mg的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(1.0mmol)和345.5mg碳酸钾(2.5mmol)，油浴30℃保温反应18h。冷却至室温， 用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到330mg的复合物G12，为亮红色固体，收率75.6％。
1H NMR(600MHz,CDCl 3)δ8.50(s,1H),8.39(s,1H),8.14(m,6H),7.65(m,4H),7.39(d,J＝7.9Hz,1H),7.35(d,J＝7.5Hz,1H),7.24(m,1H),7.17(s,1H),7.14(s,1H),6.72(s,1H),6.70(s,1H),6.23(s,1H),2.64(s,3H),2.55(s,3H),2.36(s,3H),2.28(s,3H),2.25(s,3H),2.19(s,3H).MS(MALDI-TOF)m/z[M+Na] +calcd.for IrC 45H 38O 2N 5Na 896.255,found 896.000.
合成实施例5：化合物G14的合成
Figure PCTCN2022075003-appb-000022
(1)配体5-甲基-6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL干燥的四氢呋喃，通入氮气鼓泡30min，氮气保护下依次加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和28.6g的2-甲基-3-氧代丁酸乙酯(198.4mmol)，室温搅拌40min。将22.3g的1-(吡啶-2-基羰基)苯并三唑(99.6mmol)溶于60mL四氢呋喃，采用滴加的方式加入反应体系，室温反应12h。加入20g硅胶淬灭反应，减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为6:1的混合液)，得到12.38g的2-甲基-3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为60％。
1H NMR(600MHz,CDCl 3)δ8.66(d,J＝4.8Hz,1H),8.08(d,J＝7.8Hz,1H),7.85(td,J 1＝7.7Hz,J 2＝1.6Hz,1H),7.48(m,1H),4.71(q,J＝7.1Hz,1H),4.13(q,J＝7.1Hz,2H),1.5(d,J＝7.1Hz,3H),1.14(t,J＝7.1Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入56.8g的2-甲基-3-氧代-3-(吡啶-2-基)丙酸乙 酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到18g的5-甲基-6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.39(s,1H),11.47(s,1H),8.51(s,1H),7.43(s,1H),7.41(s,1H),7.39(s,1H),2.39(s,3H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入16g的5-甲基-6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到7.43g的5-甲基-6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为50％。
1H NMR(400MHz,DMSO-d 6)δ11.35(s,1H),10.98(s,1H),8.71(s,1H),8.09(s,1H),7.97(s,1H),7.58(s,1H),2.33(s,3H).
(2)化合物G14的合成
a)在2000mL三口瓶中加入630mL甲苯、473mL水和126mL乙醇，通入氮气鼓泡30min，氮气保护下依次加入105g碳酸钾(759mmol)，8.5g的四三苯基膦钯(7.34mmol)，40g的2-溴吡啶(253mmol)，37.1g苯硼酸(304mmol)，加热至105℃回流，反应12h。用300mL水淬灭反应，分离水相和有机相，水相用乙酸乙酯萃取，合并有机相，并用无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到31.8g的2-苯基吡啶，为淡黄色透明液体，收率为81％，纯度为99.05％。
1H NMR(400MHz,CDCl 3)δ8.70(m,1H),8.00(m,2H),7.75(m,2H),7.45(m,3H),7.25(m,1H).
b)在250mL三口瓶中加入60mL乙二醇单甲醚和20mL水，通入氮气鼓泡30min，氮气保护下依次加入1.76g的2-苯基吡啶(11.36mmol)和1g三水合三氯化铱(2.84mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到1.28g的铱复合物二聚体，为黄色固体，产率为84％。
c)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入321.6mg的铱复合物二聚体(0.3mmol)、244mg的5-甲基-6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应12h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水 硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到310mg的复合物G14，为橙黄色固体，收率73.5％。
1H NMR(600MHz,CDCl 3)δ8.51(d,J＝6.4Hz,1H),8.06(d,J＝7.8Hz,1H),7.86(m,6H),7.68(m,2H),7.65(m,2H),7.33(d,J＝6.1Hz,1H),7.07(t,J＝6.6Hz,1H),6.96(t,J＝8.0Hz,1H),6.83(m,4H),6.28(m,2H),2.21(s,3H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 32H 25O 2N 5 704.164,found 704.055.
合成实施例6：化合物G21的合成
Figure PCTCN2022075003-appb-000023
(1)配体6-(喹啉-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至115℃回流。将17.05g的2-乙酰喹啉(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应12h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为20:1的混合液)，得到15.75g的3-氧代-3-(喹啉-2-基)丙酸乙酯，为白色固体，收率为65％。
1H NMR(600MHz,CDCl 3)δ8.27(d,J＝8.3Hz,1H),8.16(t,J＝7.2Hz,2H),7.88(d,J＝8.2Hz,1H),7.79(t,J＝7.2Hz,1H),7.64(t,J＝7.5Hz,1H),4.36(s,2H),4.22(q,J＝7.2Hz,2H),1.26(t,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入66.7g的3-氧代-3-(喹啉-2-基)丙酸乙酯(274 mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到24.5g的6-(喹啉-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为35％。
1H NMR(400MHz,DMSO-d 6)δ12.39(s,1H),12.05(s,1H),8.75(m,1H),7.93(m,2H),7.50(m,2H),7.26(m,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入18.7g的6-(喹啉-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到7.52g的6-(喹啉-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为43％。
1H NMR(400MHz,DMSO-d 6)δ10.84(s,1H),9.98(s,1H),8.65(m,1H),7.87(m,2H),7.38(m,2H),7.31(m,1H),6.55(s,1H).
(2)化合物G21的合成
a)在2000mL三口瓶中加入630mL甲苯、473mL水和126mL乙醇，通入氮气鼓泡30min，氮气保护下依次加入105g碳酸钾(759mmol)，8.5g的四三苯基膦钯(7.34mmol)，40g的2-溴吡啶(253mmol)，37.1g苯硼酸(304mmol)，加热至105℃回流，反应12h。用300mL水淬灭反应，分离水相和有机相，水相用乙酸乙酯萃取，合并有机相，并用无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到31.8g的2-苯基吡啶，为淡黄色透明液体，收率为81％，纯度为99.05％。
1H NMR(400MHz,CDCl 3)δ8.70(m,1H),8.00(m,2H),7.75(m,2H),7.45(m,3H),7.25(m,1H).
b)在250mL三口瓶中加入60mL乙二醇单甲醚和20mL水，通入氮气鼓泡30min，氮气保护下依次加入1.76g的2-苯基吡啶(11.36mmol)和1g三水合三氯化铱(2.84mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到1.28g的铱复合物二聚体，为黄色固体，产率为84％。
c)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入321.6mg的铱复合物二聚体(0.3mmol)、287mg的6-(喹啉-2-基)-2,4(1H,3H)-嘧啶二酮(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应12h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸 除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到284mg的复合物G21，为橙红色固体，收率64％。
1H NMR(600MHz,CDCl 3)δ8.78(d,J＝6.3Hz,1H),8.21(d,J＝7.8Hz,1H),7.80(m,8H),7.71(m,2H),7.61(m,2H),7.33(d,J＝6.2Hz,1H),7.07(t,J＝6.5Hz,1H),6.96(t,J＝8.3Hz,1H),6.79(m,4H),6.26(m,2H),6.16(d,J＝7.5Hz,1H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 35H 25O 2N 5 740.164,found 740.021.
合成实施例7：化合物G27的合成
Figure PCTCN2022075003-appb-000024
(1)配体6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮的合成
a)在1000mL三口瓶中加入240mL甲苯，通入氮气鼓泡30min，氮气保护下加入11.1g氢化钠(氢化钠质量分数为60％，277.5mmol)和23.4g碳酸二乙酯(198.4mmol)，加热至115℃回流。将12.064g的2-乙酰吡啶(99.6mmol)溶解于60mL甲苯，采用滴加的方式加入反应体系，反应5h。采用40mL冰醋酸和120mL冰水混合均匀后淬灭反应，分离水相和有机相，甲苯萃取水相，合并有机相，冰水洗至近中性，用无水硫酸钠进行干燥。减压蒸除溶剂，硅胶柱层析分离(采用石油醚和乙酸乙酯体积比为10:1的混合液)，得到14.11g的3-氧代-3-(吡啶-2-基)丙酸乙酯，为浅棕色透明液体，收率为73％。
1H NMR(600MHz,CDCl 3)δ7.58(d,J＝0.9Hz,1H),7.24(d,J＝3.6Hz,1H),6.54(dd,J 1＝3.6Hz,J 2＝1.6Hz,1H),4.17(q,J＝7.2Hz,2H),3.81(s,2H),1.22(s,J＝7.2Hz,3H).
b)在2000mL三口瓶中加入1500mL乙醇，通入氮气鼓泡30min，氮气保护下加入8.2g金属钠(356mmol)至完全溶解，然后加入53g的3-氧代-3-(吡啶-2-基)丙酸乙酯(274mmol)和27.1g硫脲(356mmol)，加热至95℃回流，反应24h。减压蒸除反应溶剂，加水 至残余物完全溶解，用2M盐酸调节pH为6-8至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到16.7g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮，为白色粉末状固体，收率为30％。
1H NMR(400MHz,DMSO-d 6)δ12.70(s,1H),11.34(s,1H),8.75(s,1H),8.17(s,1H),8.01(s,1H),7.62(s,1H),6.69(s,1H).
c)在1000mL三口瓶中加入375mL水，将31.8g氯乙酸(336.5mmol)溶于水中，加入15g的6-(吡啶-2-基)-2-硫代-4(1H,3H)-嘧啶酮(73.1mmol)，加热至105℃回流，反应24h。冷却至室温，用2M氢氧化钠溶液调节pH为6-7至沉淀完全，减压过滤，滤渣依次用水、石油醚洗涤，真空干燥，得到6.13g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮，为白色粉末状固体，收率为44.4％，纯度为98.21％。
1H NMR(400MHz,DMSO-d 6)δ11.23(s,1H),10.60(s,1H),8.72(s,1H),8.11(s,1H),7.99(s,1H),7.57(s,1H),6.33(s,1H).
(2)化合物G27的合成
a)在250mL三口瓶中加入60mL乙二醇单甲醚和20mL水，通入氮气鼓泡30min，氮气保护下依次加入2.15g的6-(吡啶-2-基)-2,4(1H,3H)-嘧啶二酮(11.36mmol)和1g三水合三氯化铱(2.84mmol)，加热至110℃回流，反应24h。冷却至室温，减压过滤，滤渣依次用水和丙酮混合液(水和丙酮的体积比为1:1)、石油醚洗涤，真空干燥，得到1.4g的铱复合物二聚体，为暗红色固体，产率为82％。
b)在100mL三口瓶中加入22mL乙二醇单甲醚，通入氮气鼓泡30min，氮气保护下依次加入362.4mg的铱复合物二聚体(0.3mmol)、186mg的2-苯基吡啶(1.2mmol)和414.6mg碳酸钾(3mmol)，加热至125℃回流，反应24h。冷却至室温，用15mL水淬灭反应，二氯甲烷萃取，饱和食盐水洗涤有机相，无水硫酸钠干燥。减压蒸除溶剂，硅胶柱层析分离(采用二氯甲烷和甲醇体积比为20:1的混合液)，得到295mg的复合物G27，为橙黄色固体，收率68％。
1H NMR(600MHz,CDCl 3)δ8.25(s,1H),8.23(s,1H),8.03(m,2H),7.91(m,1H),7.73(m,2H),7.50(m,4H),7.38(m,4H),7.05(m,2H),6.95(m,1H),6.31(s,1H),6.30(s,1H).MS(MALDI-TOF)m/z[M+H] +calcd.for IrC 27H 19O 6N 9 724.128,found 724.363.
本申请的其它化合物均可通过与合成实施例1-7类似的方法进行合成。
实施例1
将涂布了厚度为130nm的氧化铟锡(ITO)透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮-乙醇混合溶剂中超声除油，在洁净环境下烘烤至完全除 去水份，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；
然后，把上述带有阳极的玻璃基片置于真空腔内，抽真空至小于10 -5torr，在上述阳极层膜上真空蒸镀空穴注入层，空穴注入层的材料包括空穴注入层材料HT-34和p型掺杂剂p-1，利用多源共蒸的方法进行蒸镀，调节空穴注入层材料HT-34的蒸镀速率为0.1nm/s，p型掺杂剂p-1的蒸镀速率为空穴注入层材料HT-34蒸镀速率的3％，蒸镀总膜厚为10nm；
然后，在空穴注入层之上真空蒸镀空穴传输层材料HT-34作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为112nm；
然后，在空穴传输层之上真空蒸镀电子阻挡层材料EB-05作为电子阻挡层，蒸镀速率为0.1nm/s，蒸镀膜厚为10nm；
然后，在电子阻挡层之上真空蒸镀发光层，发光层包括主体材料RH-11和本申请提供的客体材料G1，主体材料RH-11和客体材料G1的质量比为97:3，利用多源共蒸的方法进行蒸镀，调节主体材料的蒸镀速率为0.1nm/s，客体材料的蒸镀速率为主体材料RH-11蒸镀速率的3％，蒸镀总膜厚为20nm；
然后，在发光层之上真空蒸镀空穴阻挡层材料HB-05作为空穴阻挡层，蒸镀速率为0.1nm/s，蒸镀膜厚为5nm；
然后，在空穴阻挡层之上真空蒸镀电子传输层，电子传输层的材料包括电子传输材料ET-43和n型掺杂剂n-1，电子传输材料ET-43和n型掺杂剂n-1的质量比为1:1，利用多源共蒸的方法进行蒸镀，调节电子传输材料ET-43的蒸镀速率为0.1nm/s，n型掺杂剂n-1的蒸镀速率为电子传输材料ET-43蒸镀速率的3％，蒸镀总膜厚为35nm；
最后，在电子传输层上蒸镀厚度为18nm的阴极，蒸镀速率为0.1nm/s，阴极材料为镁铝混合物，镁和铝的质量比为1：9。
实施例2-13
除了分别用化合物G2、G3、G8、G9、G10、G12、G14、G19、G21、G22、G23、G27代替G1以外，其余与实施例1相同。
对比例1
除了用化合物RPD-8代替G1以外，其余与实施例1相同。
对比例2
除了用化合物RPD-15代替G1以外，其余与实施例1相同。
有机电致发光器件性能测试方法
在同样亮度下，使用数字源表及亮度计测定实施例以及对比例制备得到的有机电致发光器件的驱动电压和电流效率以及器件的寿命，具体而言，以每秒0.1V的速率提升电压， 测定当有机电致发光器件的亮度达到6000nit时的电压即驱动电压，同时测出此时的电流密度；亮度与电流密度的比值即为电流效率；LT95的寿命测试如下：使用亮度计在6000nit亮度下，保持恒定的电流，测量有机电致发光器件的亮度降为5700cd/m 2的时间，单位为小时。
表1.实施例和对比例中器件性能对比
Figure PCTCN2022075003-appb-000025
从上表数据可知，实施例1至实施例13中制备有机电致发光的器件是采用本申请提供的化合物G1、G2、G3、G8、G9、G10、G12、G14、G19、G21、G22、G23、G27用于发光层，作为发光层中的客体材料，相比于对比例1和对比例2中采用现有技术中已知材料作为有机电致发光器件的发光层客体材料，器件的驱动电压更低，电流效率更高，LT95寿命更长。从而说明将本申请的化合物作为有机电致发光器件的发光层客体材料，可以有效调控发光波长，提高发光效率，延长器件的寿命。此外，采用本申请提供的化合物作为发光层客体材料制备发光层，发光层的蒸镀温度更低，有利于有机电致发光器件的加工。
以上所述仅为本申请的较佳实施例，并非用于限定本申请的保护范围。凡在本申请的精神和原则之内所作的任何修改、等同替换、改进等，均包含在本申请的保护范围内。

Claims (12)

  1. 一种化合物，其结构如式(I)所示：
    Figure PCTCN2022075003-appb-100001
    其中，
    X-Y为双芳基双齿配体，X和Y的配位原子为C或N，X-Y选自以下化合物的亚基或以下化合物的衍生物的亚基：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯；
    Z-W为含有天然杂环的双芳基双齿配体，Z的配位原子为C或N，Z选自以下化合物的亚基或以下化合物的衍生物的亚基：苯、萘、吡啶、咪唑、吡咯、四氢吡咯、哌啶、吗啉、喹啉、异喹啉、嘧啶、吡嗪、哒嗪、1,3,4-三唑、四唑、噁唑、噻唑；W的配位原子为N，W选自以下化合物的亚基或以下化合物的衍生物的亚基：腺嘌呤、鸟嘌呤、胸腺嘧啶、胞嘧啶、尿嘧啶；
    n选自0、1、2。
  2. 根据权利要求1所述的化合物，其中，
    当X-Y选自以下化合物的衍生物的亚基时：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯，所述化合物的衍生物为被取代的化合物，取代基各自独立地选自：卤素、被卤素取代或未取代的C 1-C 10烷基、被卤素取代或未取代的C 6-C 14芳基、被卤素取代或未取代的C 6-C 14芳基烷氧基；
    当Z选自以下化合物的衍生物的亚基时：苯、萘、吡啶、咪唑、吡咯、四氢吡咯、哌啶、吗啉、喹啉、异喹啉、嘧啶、吡嗪、哒嗪、1,3,4-三唑、四唑、噁唑、噻唑，所述化合物的衍生物为被取代的化合物，取代基各自独立地选自：氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14 芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；所述杂芳基上的杂原子选自O、S、N；各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基；
    当W选自以下化合物的衍生物的亚基时：腺嘌呤、鸟嘌呤、胸腺嘧啶、胞嘧啶、尿嘧啶，所述化合物的衍生物为被取代的化合物，取代基各自独立地选自：氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；所述杂芳基上的杂原子选自O、S、N；各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基。
  3. 根据权利要求1所述的化合物，其中，X-Y选自以下化合物的亚基：2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯基吡啶、苯并噻吩吡啶、苯基亚胺、乙烯基吡啶、芳基喹啉、芳基异喹啉、吡啶基萘、吡啶基吡咯、吡啶基咪唑、吡啶基吲唑、苯基咪唑、苯基三唑、苯基吲哚、苯基嘧啶、苯基哒嗪、联吡啶、联苯、5-甲基-2-苯基吡啶、5-甲基-2-(2,4-二氟苯基)吡啶、2-(2,4-二氟苯基)-5-三氟甲基吡啶、2-(2,4-二氟苯基)嘧啶、2-(3,4-二氟苯基)-1-(2,4,6-三甲基苯基)咪唑、1,3-二甲基-5-(3-氟苯基)三唑、1-(3,5-二甲基苯基)异喹啉、6-异丙基-1-(3,5-二甲基苯基)异喹啉、2-(3,5-二甲基苯基)喹啉、4-甲基-2-(3,5-二甲基苯基)喹啉、2’,4’-二氟-2,3’-联吡啶、1-甲基-3-(4-甲基苯基)-2,3-二氢咪唑、6-苯基-3-(2,4,6-三甲基苯氧基)哒嗪、1-(4-仲丁基苯基)异喹啉、3-异丙基-2-(3-甲基苯基)喹啉、5-甲基-2-(3,5-二甲基苯基)吡啶。
  4. 根据权利要求1所述的化合物，其具有以下通式中的一种：
    Figure PCTCN2022075003-appb-100002
    其中，
    n 1-n 4各自独立地选自0、1、2。
  5. 根据权利要求1所述的化合物，其具有以下通式中的一种：
    Figure PCTCN2022075003-appb-100003
    其中，
    R a1-R a4、R b1-R b6、R c1-R c6、R d1-R d4、R e1-R e6、R f1-R f6各自独立地选自氢、氘、卤素、未取代或被Ra取代的C 1-C 10烷基、未取代或被Ra取代的C 3-C 10环烷基、未取代或被Ra取代的C 6-C 14芳基、未取代或被Ra取代的C 2-C 14杂芳基、未取代或被Ra取代的C 1-C 10烷氧基、未取代或被Ra取代的胺基；
    所述杂芳基上的杂原子选自O、S、N；
    各个基团的取代基Ra各自独立地选自氘、卤素、硝基、氰基、C 1-C 4的烷基、苯基、联苯基、三联苯基、萘基；
    n 5-n 12各自独立地选自0、1、2。
  6. 根据权利要求1-5中任意一项所述的化合物，其选自下述结构G1-G30中的任意一个：
    Figure PCTCN2022075003-appb-100004
    Figure PCTCN2022075003-appb-100005
  7. 一种根据权利要求1-6中任意一项所述的化合物用作有机电致发光器件的功能层材料的用途。
  8. 根据权利要求7所述的用途，其中，所述功能层为发光层。
  9. 根据权利要求8所述的用途，其中，所述发光层的蒸镀温度为330℃至370℃。
  10. 一种发光层客体材料，包含如权利要求1-6中任意一项所述化合物中的至少一种。
  11. 一种有机电致发光器件，包含如权利10所述的发光层客体材料中的至少一种。
  12. 一种显示装置，包含如权利要求11所述的有机电致发光器件。
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