WO2022233243A1 - 有机化合物及包含其的电子元件和电子装置 - Google Patents

有机化合物及包含其的电子元件和电子装置 Download PDF

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WO2022233243A1
WO2022233243A1 PCT/CN2022/088662 CN2022088662W WO2022233243A1 WO 2022233243 A1 WO2022233243 A1 WO 2022233243A1 CN 2022088662 W CN2022088662 W CN 2022088662W WO 2022233243 A1 WO2022233243 A1 WO 2022233243A1
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substituted
unsubstituted
carbon atoms
independently selected
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French (fr)
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岳娜
华正伸
李应文
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陕西莱特光电材料股份有限公司
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Definitions

  • the present application relates to the technical field of organic electroluminescence, and in particular, to an organic compound and electronic components and electronic devices containing the same.
  • OLEDs Organic electroluminescent devices
  • OLEDs are thin-film devices prepared from organic photoelectric functional materials, which emit light under the excitation of an electric field.
  • OLED has been widely used in mobile phones, computers, lighting and other fields due to its advantages of high brightness, fast response, and wide adaptability.
  • organic electroluminescent devices In addition to the electrode material film, organic electroluminescent devices also require different organic functional materials, and the semiconducting properties of organic functional materials are derived from the displaced ⁇ bonds in the material molecules.
  • the valence and conduction properties of whose overlap yields the highest occupied orbital (HOMO) and molecular lowest unoccupied orbital (LUMO), respectively, generate charge transport through intermolecular transitions.
  • a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer.
  • These organic layers have the function of improving the injection efficiency of carriers (holes and electrons) at the interface of each layer, balancing the ability of carrier transport between layers, thereby improving the brightness and efficiency of the device.
  • the continuous improvement of the performance of organic electroluminescent devices requires not only the innovation of the structure and fabrication process of organic electroluminescent devices, but also the continuous research and innovation of organic electro-optical functional materials.
  • the performance of organic electroluminescent devices is mainly improved by changing organic functional materials. It is still necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices, in order to obtain lower device driving voltage and higher Device luminous efficiency and lifetime.
  • the purpose of the present application is to overcome the above-mentioned deficiencies in the prior art, and to provide an organic compound and electronic components and electronic devices containing the same.
  • a first aspect of the present application provides an organic compound whose structure is shown in formula 1:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are the same or different, and are each independently selected from the structure shown in formula 2, hydrogen, deuterium, halogen groups , cyano group, alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms or trialkylsilicon with 3 to 12 carbon atoms base, and any one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 is selected from the structure shown in formula 2; optionally, R 5 and R 6 Connected to each other to form a substituted or unsubstituted benzene ring, the substituents on the benzene ring are selected from the structure shown in formula 2, deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, carbon atom
  • L, L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, carbon atom Aryl with 6 to 20, alkyl with 1 to 5 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 12 carbon atoms; optionally, any two of Ar 1
  • the adjacent substituents form a saturated or unsaturated 3-15-membered ring; optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 3-15-membered ring.
  • the present application adopts the fluorene derivative structure as the main structure of the organic compound.
  • the fluorene structure has a higher triplet state energy level and has the ability to transport holes.
  • the fluorene derivative is connected with a triarylamine compound, which is helpful for dispersing the material.
  • the charge, and the direct connection of adamantane on the five-membered ring of fluorene increases the degree of freedom between molecules, effectively reduces the coplanarity of molecules, and reduces the degree of stacking between molecules, which makes organic compounds difficult to crystallize during film formation. Or aggregated, can have a more stable amorphous state, making the material have the advantages of low driving voltage, high efficiency and long life in devices.
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer interposed between the anode and the cathode, wherein the functional layer contains the above-mentioned organic compound.
  • a third aspect of the present application provides an electronic device including the above electronic component.
  • 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 an electronic device according to an embodiment of the present application.
  • a first aspect of the present application provides an organic compound whose structure is shown in formula 1:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are the same or different, and are each independently selected from the structure shown in formula 2, hydrogen, deuterium, halogen groups , cyano group, alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms or trialkylsilicon with 3 to 12 carbon atoms base, and any one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 is selected from the structure shown in formula 2; optionally, R 5 and R 6 Connected to each other to form a substituted or unsubstituted benzene ring, the substituents on the benzene ring are selected from the structure shown in formula 2, deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, carbon atom
  • L, L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, carbon atom Aryl with 6 to 20, alkyl with 1 to 5 carbon atoms, trialkylsilyl or triphenylsilyl with 3 to 12 carbon atoms; optionally, any two of Ar 1
  • the adjacent substituents form a saturated or unsaturated 3-15-membered ring; optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 3-15-membered ring.
  • R 5 and R 6 are connected to each other to form a benzene ring
  • R 5 and R 6 may or may not form a benzene ring
  • each independently is and “are independently” and “are independently selected from each other” can be interchanged, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is: formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings The number q of "substituents" can be the same or different, 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 described 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 group having a substituent Rc or an unsubstituted aryl group.
  • substituent namely Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, alkyl group, trialkylsilyl group or triphenylsilyl group, optionally, any two of the The substituents are attached to each other to form, together with the atoms to which they are attached, a saturated or unsaturated ring of 3 to 15 members.
  • the "substituted" functional group may be substituted by one or more than two substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc may exist independently or Connected to each other to form a ring with the atoms; when there are two adjacent substituents Rc on a functional group, the adjacent two substituents Rc may exist independently or be condensed to form a ring with the functional group to which they are connected.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to all carbon atoms.
  • L is selected from a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12.
  • Ar 1 is Then the number of carbon atoms is 10; L is Its carbon number is 12.
  • hetero means that a functional group includes at least one heteroatom such as B, N, O, S, P, Si or Se and the remaining atoms are carbon and hydrogen.
  • alkyl may include straight-chain or branched-chain alkyl groups.
  • Alkyl groups may have 1 to 10 carbon atoms, and herein, a numerical range such as “1 to 10" refers to each integer in the given range; for example, "an alkyl group of 1 to 10 carbon atoms” means an 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms alkyl.
  • the alkyl group is selected from alkyl groups with 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and pentyl.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • the substituted aryl group may be one or more than two hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethyl silicon group group, alkyl, cycloalkyl, alkoxy, alkylthio and other groups.
  • a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethyl silicon group group, alkyl, cycloalkyl, alkoxy, alkylthio and other groups.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents.
  • the total number of carbon atoms of the substituents is 18.
  • aryl groups as substituents include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, and biphenyl.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms can be B, O, N, P One or more of , Si, Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
  • thienyl, furanyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic groups connected by carbon-carbon bond conjugation System type of heteroaryl.
  • the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trimethylsilyl group, an alkyl group , cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trimethylsilyl group, an alkyl group , cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl groups as substituents include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoline oxalinyl.
  • halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • Ring in this application includes saturated ring, unsaturated ring; saturated ring, namely cycloalkyl, heterocycloalkyl; unsaturated ring, namely cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • a non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. Any possible connection method shown by -1) to formula (f-10):
  • the dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of one side of the benzene ring,
  • the meaning it represents includes any possible connection mode shown by formula (X'-1) to formula (X'-4):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are the same or different, and are each independently selected from those shown in formula 2
  • the organic compound has one and only one structure represented by formula 2.
  • the structure of the organic compound is as follows:
  • L, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted aryl group having 6-12 carbon atoms, and a substituted or unsubstituted aryl group having 5-18 carbon atoms. or unsubstituted heteroaryl.
  • L, L 1 and L 2 are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12 carbon atoms, 5, 6 carbon atoms , 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 substituted or unsubstituted heteroaryl.
  • L, L 1 and L 2 are each independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.
  • the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert - butyl, trimethylsilyl, phenyl or naphthalene base.
  • L, L 1 and L 2 are each independently selected from a single bond or a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of:
  • the substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl , phenyl or naphthyl; when the number of substituents is greater than 1, the substituents are the same or different.
  • L, L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • L, L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms or substituted or unsubstituted hetero groups with 12-20 carbon atoms Aryl.
  • Ar 1 and Ar 2 are independently selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, A substituted or unsubstituted aryl group of 23, 24, 25, or a substituted or unsubstituted heteroaryl group of 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
  • the substituents in Ar 1 and Ar 2 are independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, and 3-12 heteroaryl, trimethylsilyl or triphenylsilyl; optionally, any two adjacent substituents in Ar 1 form a saturated or unsaturated 5-13-membered ring; any Optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 5-13 membered ring.
  • Ar and Ar are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted substituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, trimethyl Silyl or triphenylsilyl; optionally, any two adjacent substituents in Ar 1 form a fluorene ring; optionally, any two adjacent substituents in Ar 2 form fluorene ring.
  • Ar 1 and Ar 2 are independently selected from substituted or unsubstituted group W, and unsubstituted group W is selected from the group consisting of the following groups:
  • the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthalene group, carbazolyl group, trimethylsilyl group or triphenylsilyl group; when the number of substituent groups is greater than 1, each substituent group is the same or different.
  • Ar 1 and Ar 2 are independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are independently selected from the group consisting of the following groups:
  • the organic compound is selected from the group formed by the following compounds:
  • a second aspect of the present application provides an electronic component for realizing photoelectric conversion or electro-optical conversion.
  • the electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound of the present application.
  • the functional layer includes a hole adjustment layer
  • the hole adjustment layer includes the organic compound of the present application.
  • the electronic component is an organic electroluminescence device or a photoelectric conversion device, preferably an organic electroluminescence device.
  • the organic electroluminescent device is a red organic electroluminescent device.
  • the organic electroluminescent device of the present application includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 interposed between the anode layer and the cathode layer.
  • the layer 300 includes a hole injection layer 310, a hole transport layer 320, a hole adjustment layer 330, an organic light-emitting layer 340, an electron transport layer 350 and an electron injection layer 360; the hole injection layer 310, the hole transport layer 320, the hole
  • the adjustment layer 330 , the organic light emitting layer 340 , the electron transport layer 350 and the electron injection layer 360 are sequentially formed on the anode 100 .
  • the hole adjustment layer 330 may contain the organic compounds described in this application.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; 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 SnO2: Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-9(ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 320 is selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, which are not specifically limited in this application. In one embodiment of the present application, the hole transport layer 320 is NPB.
  • the hole adjustment layer 330 is composed of the organic compound provided in the present application.
  • This application uses fluorene derivatives as the main structure of organic compounds.
  • the fluorene structure has a higher triplet energy level and has the ability to transport holes and electrons.
  • the fused ring on the fluorene structure can form a large rigidity.
  • the plane is beneficial to improve the stability of the material.
  • the triarylamine compound is connected to the fluorene derivative, which helps to disperse the charge of the material, reduce the coplanarity of the molecule, make the product easier to form a film, and increase the product's stability.
  • 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. The holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons, and the excitons transfer energy to the host material, and the host material will The energy is transferred to the guest material, which in turn enables the guest material to emit light.
  • the host material of the organic light-emitting layer 340 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this application.
  • the host material of the organic light-emitting layer 340 is CBP.
  • the guest material of the organic light-emitting layer 340 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not specially made in this application. limit.
  • the guest material of the organic light-emitting layer 340 is Ir(piq) 2 (acac).
  • the electron transport layer 350 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials.
  • the electron transport layer 350 consists of ET-06 and LiQ.
  • the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca, but not limited thereto.
  • a metal electrode comprising silver and magnesium is preferably included as the cathode.
  • a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 320 to enhance the capability of injecting holes into the hole transport layer 320 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 is F4-TCNQ.
  • an electron injection layer 360 is further disposed between the cathode 200 and the electron transport layer 350 to enhance the capability of injecting electrons into the electron transport layer 350 .
  • the electron injection layer 360 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 360 includes ytterbium (Yb).
  • a third aspect of the present application provides an electronic device including the electronic component of the second aspect of the present application.
  • the electronic device provided by the present application is an electronic device 400
  • the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • 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 computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • the intermediate shown in Table 1 is synthesized with reference to the synthetic method of IM 2-1, the difference is that the raw material 1 is used to replace the 9-fluorenone, wherein the main raw material used, the synthetic intermediate and the yield thereof are as shown in Table 1 Show.
  • the IM 4-X shown in table 2 is synthesized, and the difference is that raw material 2 is used to replace IM 2-1, wherein, the main raw material used, the synthetic intermediate and the yield thereof are as shown in the table 2 shown.
  • the filtrate was then distilled under reduced pressure to remove the solvent to obtain the crude product; the crude product was purified by silica gel column, and then recrystallized and purified with a dichloromethane/n-heptane system to obtain a white solid IM A1-2 (19.46 g, yield 66%) .
  • IM A1-3 shown in Table 3 is synthesized with reference to the synthetic method of IM A1-2, the difference is that IM 4-3 is used to replace IM 4-2, and the main raw material used, the synthetic intermediate and the yield thereof are such as shown in Table 3.
  • IM A2-X shown in Table 4 is synthesized with reference to the synthetic method of IM A2-1, and the difference is that IM 4-X is used to replace IM 4-1, and raw material 3 is used to replace phenylboronic acid.
  • the intermediates and their yields are shown in Table 4.
  • Extract the reaction solution collect the organic phase, use anhydrous magnesium sulfate to dry the organic phase, filter the filtrate to remove the solvent under reduced pressure to obtain a crude product; use a toluene system to recrystallize and purify the crude product to obtain IMA3-1 (12.5 g, yield 78.2%).
  • the IMA3-X shown in Table 5 is synthesized, and the difference is that the raw material 4 is used to replace IMA2-1, and the main raw material used, the synthetic intermediate and the yield thereof are as shown in Table 5 shown.
  • the IMA4-X shown in table 6 is synthesized with reference to the synthetic method of IMA4-1, and the difference is that IMA3-X is used to replace IMA3-1, and raw material 5 is used to replace p-chloroiodobenzene, and the main raw materials used, synthetic
  • Table 6 The intermediates and their yields are shown in Table 6.
  • the IM A5-X shown in Table 7 is synthesized with reference to the synthetic method of IM A5-1, the difference is that the raw material 6 is used to replace the IM A2-1, the raw material 7 is used to replace the 4-aminobiphenyl, and the main raw materials used, synthetic
  • Table 7 The intermediates and their yields are shown in Table 7.
  • the compound X listed in Table 8 is synthesized with reference to the synthetic method of compound 262, and the difference is that IM A5-X is used to replace IM A5-1, and raw material 8 is used to replace 4-bromobiphenyl, and the main raw material used therein, the synthesized compound Its yield and mass spectrum are shown in Table 8.
  • Organic electroluminescent devices were prepared by the following process: the thickness of The anode 100ITO substrate was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns, using ultraviolet ozone and O 2 : N 2 plasma was used for surface treatment to increase the work function of the anode (experimental substrate), and organic solvent was used to clean the surface of the ITO substrate to remove scum and oil stains on the surface of the ITO substrate.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL); and vacuum evaporation of NPB on the hole injection layer to form a thickness of The hole transport layer (HTL).
  • HIL hole injection layer
  • NPB hole transport layer
  • Compound 262 was vacuum evaporated on the hole transport layer to form a thickness of the hole adjusting layer.
  • CBP and Ir(piq) 2 (acac) were co-evaporated at a film thickness ratio of 97%:3% to form a thickness of The organic light-emitting layer (EML).
  • ET-06 and LiQ were vapor-deposited at a film thickness ratio of 1:1 to form a thickness of of electron transport layer (ETL), then Yb was evaporated on the electron transport layer to form a thickness of the electron injection layer (EIL).
  • ETL electron transport layer
  • EIL electron injection layer
  • Magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer at a film thickness ratio of 1:9 to form a thickness of the cathode 200.
  • CP-05 was vapor-deposited on the cathode to form a thickness of the organic capping layer (CPL), thereby completing the fabrication of organic electroluminescent devices.
  • CPL organic capping layer
  • An organic electroluminescence device was fabricated in the same manner as in Example 1, except that the other compounds described in Table 11 were used instead of Compound 262 when forming the hole adjusting layer.
  • the organic electroluminescent devices prepared in Examples 1 to 33 have improved performances.
  • the driving voltage of the organic electroluminescent device is at least 9.7% lower, current efficiency (Cd/A) at least 13.4% higher, power efficiency (lm/W) at least 12.1% higher, external quantum efficiency at least 14% higher, lifetime at least 9% higher, highest lifetime Can be increased by 68h. From the above data, it can be seen that the luminous efficiency (Cd/A) and the lifetime (T95) of the electronic device are significantly improved by using the organic compound of the present application as the hole adjusting layer of the electronic device.

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Abstract

本申请提供一种有机化合物及其电子元件和电子装置，属于有机电致发光技术领域。该有机化合物的结构如式1所示，该有机化合物具有优异的光电性能，可以提高器件的发光效率和使用寿命，并能够降低驱动电压。

Description

有机化合物及包含其的电子元件和电子装置
相关申请的交叉引用
本申请要求于2021年5月7日递交的申请号为202110497252.X的中国专利申请的优先权，其全部内容通过引用并入在本申请中。
技术领域
本申请涉及有机电致发光技术领域，具体涉及一种有机化合物及包含其的电子元件和电子装置。
背景技术
有机电致发光器件(OLED)是通过有机光电功能材料制备的薄膜器件，在电场的激发下进行发光。目前，OLED由于其亮度高、响应快、适应性广等优点已广泛应用于手机、电脑、照明等领域。
有机电致发光器件除了电极材料膜层，还需要不同有机功能材料，而有机功能材料的半导性质则是源于材料分子内移位的π键，π键或反π键轨道形成了移位的原子价和传导性能，其交迭分别产生了最高占据轨道(HOMO)和分子最低空轨道(LUMO)，通过分子间跃迁产生电荷传输。
为了提高有机电致发光器件的亮度、效率和寿命，一般采用多层结构，包括：空穴注入层、空穴传输层、发光层和电子传输层等。这些有机层具有提高载流子(空穴和电子)在各层界面间的注入效率，平衡载流子在各层之间传输的能力，从而提高器件的亮度和效率的功能。
有机电致发光器件性能的不断提升，不仅需要有机电致发光器件的结构和制作工艺的创新，也需要对有机电致光电功能材料的不断研究和创新。目前，主要通过改变有机功能材料来提高有机电致发光器件性能，仍有必要继续研发新型的材料，以进一步提高有机电致发光器件的性能，以期获得更低的器件的驱动电压，更高的器件发光效率和使用寿命。
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。
发明内容
本申请的目的在于克服上述现有技术中的不足，提供一种有机化合物及包含其的电子元件和电子装置。
本申请的第一方面提供一种有机化合物，其结构如式1所示：
Figure PCTCN2022088662-appb-000001
其中，
Figure PCTCN2022088662-appb-000002
表示化学键，
R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9相同或不同，且各自独立地选自式2所示的结构、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基，且R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9中任一者选自式2所示结构；任选地，R 5和R 6相互连接形成取代或未取代的苯环，所述苯环上的取代基选自式2所示 的结构、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基；
L、L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基或者碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为1～5的烷基、碳原子数为3～12的三烷基硅基或三苯基硅基；任选地，Ar 1中的任意两个相邻的取代基形成饱和或不饱和的3～15元环；任选地，Ar 2中的任意两个相邻的取代基形成饱和或不饱和的3～15元环。
本申请采用芴类衍生物结构作为有机化合物的主体结构，芴类结构具有较高的三线态能级，具备空穴传输能力，芴类衍生物上连接三芳胺类化合物，有助于分散材料的电荷，而在芴的五元环上直接连接金刚烷，增加了分子间的自由度，有效地降低分子的共平面性，减小分子间的堆叠程度，进而使得有机化合物在成膜时不易结晶或聚集，能够具有更为稳定的无定形态，使得材料在器件中具有低驱动电压、高效率和长寿命的优势。
本申请的第二方面提供一种电子元件，包括相对设置的阳极和阴极、以及介于所述阳极与阴极之间的功能层，其中，所述功能层包含上述有机化合物。
本申请的第三方面提供一种电子装置，包括上述电子元件。
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。
附图说明
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：
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。
图2是本申请一种实施方式的电子装置的示意图。
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、空穴调整层；340、有机发光层；350、电子传输层；360、电子注入层；400、电子装置。
具体实施方式
现在将参考附图更全面地描述示例性实施方式。然而，示例性实施方式能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施方式使得本申请将更加全面和完整，并将示例性实施方式的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施方式中。在下面的描述中，提供许多具体细节从而给出对本申请的实施方式的充分理解。
本申请的第一方面提供一种有机化合物，其结构如式1所示：
Figure PCTCN2022088662-appb-000003
其中，
Figure PCTCN2022088662-appb-000004
表示化学键，
R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9相同或不同，且各自独立地选自式2所示的结构、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基，且R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9中任一者选自式2所示结构；任选地，R 5和R 6相互连接形成取代或未取代的苯环，所述苯环上的取代基选自式2所示的结构、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基；
L、L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基或者碳原子数为3～30的取代或未取代的亚杂芳基；
Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为1～5的烷基、碳原子数为3～12的三烷基硅基或三苯基硅基；任选地，Ar 1中的任意两个相邻的取代基形成饱和或不饱和的3～15元环；任选地，Ar 2中的任意两个相邻的取代基形成饱和或不饱和的3～15元环。
本申请中，“任选地，R 5和R 6相互连接形成苯环”是指R 5和R 6可以形成苯环，也可以不形成苯环。
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“……各自独立地选自”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，
Figure PCTCN2022088662-appb-000005
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。
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)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、杂芳基、芳基、烷基、三烷基硅基或三苯基硅基，任选地，任意两个所述取代基相互连接以与它们所连接的原子一起形成3～15元的饱和或不饱和环。本申请中，“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存 在或者与其所连接的官能团稠合成环。
本申请中，除非另有说明，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L选自取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar 1为
Figure PCTCN2022088662-appb-000006
则其碳原子数为10；L为
Figure PCTCN2022088662-appb-000007
其碳原子数为12。
本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、N、O、S、P、Si或Se等杂原子且其余原子为碳和氢。
本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至10个碳原子，本申请中，诸如“1至10”的数值范围是指给定范围中的各个整数；例如，“1至10个碳原子的烷基”是指包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子的烷基。
优选地，烷基选自碳原子数为1～5的烷基，具体实例包括但不限于，甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基。
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、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2022088662-appb-000008
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。
本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、叔丁基、三氟甲基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，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，指的是芳基及其取代基的总碳原子数为18。
本申请中，作为取代基的芳基，具体实例包括但不限于苯基、萘基、蒽基、菲基、二甲基芴基、联苯基。
本申请中，杂芳基是指环中包含1、2、3、4、5、6或7个杂原子的一价芳香环或其衍生物，所述杂原子可以是B、O、N、P、Si、Se和S中的一种或更多种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-苯基咔唑基、N-吡啶基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三甲基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
本申请中，作为取代基的杂芳基，具体实例包括但不限于吡啶基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、喹唑啉基、喹喔啉基。
本申请中，卤素基团可以包括氟、碘、溴、氯等。
本申请中，三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。
本申请中的“环”包含饱和环、不饱和环；饱和环即环烷基、杂环烷基；不饱和环，即环烯基、杂环烯基、芳基和杂芳基。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2022088662-appb-000009
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：
Figure PCTCN2022088662-appb-000010
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：
Figure PCTCN2022088662-appb-000011
在本申请的一种实施方式中，R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9相同或不同，且各自独立地选自式2所示的结构、氢、氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基或三甲基硅基，且R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9中任一者选自式2所示结构；任选地，R 5和R 6相互连接形成取代或未取代的苯环，所述苯环上的取代基选自式2所示的结构、氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基或三甲基硅基。
可选地，所述有机化合物中有且只有一个式2所示的结构。
可选地，所述有机化合物的结构如下所示：
Figure PCTCN2022088662-appb-000012
在本申请的一种实施方式中，L、L 1和L 2各自独立地选自单键、碳原子数为6～12的取代或未取代的芳基、碳原子数为5～18的取代或未取代的杂芳基。例如，L、L 1和L 2各自独立地选自单键，碳原子数为6、7、8、9、10、11、12的取代或未取代的芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18的取代或未取代的杂芳基。
可选地，L、L 1和L 2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基。
优选地，L、L 1和L 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基或萘基。
在本申请的一种实施方式中，L、L 1和L 2各自独立地选自单键或者取代或未取代的基团V，未取代的基团V选自如下基团所组成的组：
Figure PCTCN2022088662-appb-000013
取代的基团V上具有一个或两个以上取代基，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基或萘基；当取代基个数大于1时，各取代基相同或不同。
可选地，L、L 1和L 2各自独立地选自单键或者如下基团所组成的组：
Figure PCTCN2022088662-appb-000014
进一步可选地，L、L 1和L 2各自独立地选自单键或者如下基团所组成的组：
Figure PCTCN2022088662-appb-000015
在本申请的一种实施方式中，Ar 1和Ar 2分别独立地选自碳原子数为6～25的取代或未取代的芳基或者碳原子数为12～20的取代或未取代的杂芳基。例如，Ar 1和Ar 2分别独立地选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25的取代或未取代的芳基，或者碳原子数为12、13、14、15、16、17、18、19、20的取代或未取代的杂芳基。
优选地，Ar 1和Ar 2中的取代基分别独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基、三甲基硅基或三苯基硅基；任选地，在Ar 1中的任意两个相邻的取代基形成饱和或不饱和的5～13元环；任选地，在Ar 2中的任意两个相邻的取代基形成饱和或不饱和的5～13元环。
可选地，Ar 1和Ar 2分别独立地选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的螺二芴基；
优选地，Ar 1和Ar 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、三甲基硅基或三苯基硅基；任选地，在Ar 1中的任意两个相邻的取代基形成芴环；任选地，在Ar 2中的任意两个相邻的取代基形成芴环。
在本申请的一种实施方式中，Ar 1和Ar 2分别独立地选自取代或未取代的基团W，未取代的基团W选自如下基团所组成的组：
Figure PCTCN2022088662-appb-000016
取代的基团W上具有一个或两个以上的取代基，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、三甲基硅基或三苯基硅基；当取代基个数大于1时，各取代基相同或不同。
可选地，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
Figure PCTCN2022088662-appb-000017
进一步可选地，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
Figure PCTCN2022088662-appb-000018
可选地，所述有机化合物选自如下化合物所形成的组：
Figure PCTCN2022088662-appb-000019
Figure PCTCN2022088662-appb-000020
Figure PCTCN2022088662-appb-000021
Figure PCTCN2022088662-appb-000022
Figure PCTCN2022088662-appb-000023
Figure PCTCN2022088662-appb-000024
Figure PCTCN2022088662-appb-000025
Figure PCTCN2022088662-appb-000026
Figure PCTCN2022088662-appb-000027
Figure PCTCN2022088662-appb-000028
Figure PCTCN2022088662-appb-000029
本申请的第二方面提供一种电子元件，用于实现光电转换或者电光转化。该电子元件包括相对设置的阳极和阴极，以及介于阳极与阴极之间的功能层，所述功能层包含本申请的有机化合物。
可选地，所述功能层包括空穴调整层，所述空穴调整层包括本申请的有机化合物。
本申请中，所述电子元件为有机电致发光器件或光电转化器件，优选为有机电致发光器件。
可选地，所述有机电致发光器件为红色有机电致发光器件。
在本申请一种实施方式中，如图1所示，本申请的有机电致发光器件包括相对设置的阳极100和阴极200、以及介于阳极层与阴极层之间的功能层300，该功能层300包括空穴注入层310、空穴传输层320、空穴调整层330、有机发光层340、电子传输层350以及电子注入层360；空穴注入层310、空穴传输层320、空穴调整层330、有机发光层340、电子传输层350以及电子注入层360依次形成在阳极100上。其中，空穴调整层330可以含有本申请所述的有机化合物。
阳极100包括阳极材料，其优选地是有助于空穴注入至功能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SnO 2∶Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-9(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
空穴传输层320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。在本申请的一种实施方式中，空穴传输层320为NPB。
可选地，空穴调整层330由本申请所提供的有机化合物组成。本申请采用芴类衍生物作为有机化合物的主体结构，芴类结构具有较高的三线态能级，具备空穴传输和电子传输的能力，其中在芴结构上进行稠环，可形成大的刚性平面，有利于提高材料的稳定性，同时在芴类衍生物上连接三芳胺类化合物，有助于分散材料的电荷，降低分子的共平面性，使产品更易于成膜，增大了产品的分子量，提高产品的玻璃化转变温度，使产品不易结晶，同时在芳香胺上引入二苯并呋喃、螺二芴、二苯并噻吩等官能团，可有效增强材料的导电性，更加有利于空穴的产生和传输。
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。
有机发光层340的主体材料可以为金属螯类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层340的主体材料为CBP。
有机发光层340的客体材料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。在本申请的一种实施方式中，有机发光层340的客体材料为Ir(piq) 2(acac)。
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。在本申请的一种实施方式中，电子传输层350由ET-06和LiQ组成。
阴极200包括阴极材料，其是有助于电子注入至功能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，LiO 2/Al，LiF/Ca，LiF/Al和BaF 2/Ca，但不限于此。优选包括包含银和镁的金属电极作为阴极。
可选地，在阳极100和空穴传输层320之间还设置有空穴注入层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。在本申请的一种实施方式中，空穴注入层310为F4-TCNQ。
可选地，在阴极200和电子传输层350之间还设置有电子注入层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。在本申请的一种实施方式中，电子注入层360包括镱(Yb)。
本申请的第三方面提供一种电子装置，该电子装置包括本申请第二方面的电子元件。
举例而言，如图2所示，本申请提供的电子装置为电子装置400，该电子装置400包括上述有机电致发光器件。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。
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。
合成实施例
所属领域的专业人员应该认识到，本申请所描述的化学反应可以用来合适地制备许多本申请的其他有机化合物。例如，根据本申请那些非例证的有机化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成，如适当的保护干扰基团，通过利用其他已知的试剂除了本申请所描述的，或将反应条件做一些常规的修改。
制备例1：化合物1的合成
1.IM 2-1的合成
Figure PCTCN2022088662-appb-000030
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入9-芴酮(16.0g，88.79mmol)、十四烷基三甲基溴化铵(TTAB)(3.89g，13.32mmol)和溴化铵(NH 4Br)水溶液(30wt％,21.75g，221.9mmol)。搅拌并加热至75℃，加入溴酸钾(KBrO 3)(16.31g，97.67mmol)，保温反应3h，反应结束后，冷却至室温。加入20％亚硫酸钠水溶液，经过滤、滤饼水洗并干燥后得到黄色固体IM 2-1(20.0g，收率87％)。
参照IM 2-1的合成方法合成表1所示的中间体，不同之处在于，使用原料1代替9-芴酮，其中，使用的主要原料、合成的中间体及其收率如表1所示。
表1
Figure PCTCN2022088662-appb-000031
2.IM 4-1的合成
Figure PCTCN2022088662-appb-000032
向装有机械搅拌、温度计、滴液漏斗的三口瓶中通氮气(0.100L/min)置换15min，加入IM 2-1(19.7g，76.03mmol)和四氢呋喃(125mL)，开启搅拌，搅拌均匀后采用液氮将体系温度降至-78℃，待温度稳定后开始滴加正丁基锂(7.30g，114.05mmol)，滴加完毕后在-78℃下保温1h，然后将1-溴金刚烷(16.40g，76.03mmol)用四氢呋喃(33mL)稀释后滴加至体系中，滴加完毕后在-78℃下保温1h，然后自然升温至25℃搅拌12h。之后将反应液倒入水中(200mL)搅拌10min，然后加入二氯甲烷(250mL)进行萃取操作2次，合并有机相，用无水硫酸镁干燥后过硅胶漏斗，然后将滤液蒸干，得到IM 4-1(19.2g，收率63.8％)。
参照IM 4-1的合成方法合成表2所示的IM 4-X，不同之处在于，使用原料2代替IM 2-1，其中，使用的主要原料、合成的中间体及其收率如表2所示。
表2
Figure PCTCN2022088662-appb-000033
3.IM A1-2的合成
Figure PCTCN2022088662-appb-000034
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IM 4-2(24.6g，77.74mmol)、溴单质(13.68g，85.51mmol)、四(三苯基膦)钯(0.90g，0.78mmol)、碳酸钾(16.09g，116.61mmol)、2,2-二氯-1,3-环己基-4,5-咪唑烷二酮(28.47g，85.51mmol)和四氢呋喃(123mL)，升温至回流，搅拌反应6h；反应结束后，冷却至室温，加入二氯甲烷(1000mL)萃取，收集有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，得到粗品；粗品采用硅胶过柱纯化，之后用二氯甲烷/正庚烷体系进行重结晶提纯，得到白色固体IM A1-2(19.46g，收率66％)。
参照IM A1-2的合成方法合成表3所示的IM A1-3，不同之处在于，使用IM 4-3代替IM 4-2，其中使用的主要原料、合成的中间体及其收率如表3所示。
表3
Figure PCTCN2022088662-appb-000035
4.IM A2-1的合成
Figure PCTCN2022088662-appb-000036
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IM 4-1(19.0g，48.06mmol)、苯硼酸(6.44g，52.87mmol)、四(三苯基膦)钯(0.55g，0.48mmol)、碳酸钾(9.95g，72.09mmol)、二氯咪唑烷二酮(16.02g，48.06mmol)和四氢呋喃(95mL)，升温至回流，搅拌反应6h；反应结束后，冷却至室温，加入二氯甲烷(1000mL)萃取，收集有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，得到粗品；粗品采用硅胶过柱纯化，之后用二氯甲烷/正庚烷体系进行重结晶提纯，得到白色固体IM A2-1(14.67g，收率67％)。
参照IM A2-1的合成方法合成表4所示的IM A2-X，不同之处在于，使用IM 4-X代替IM 4-1，使用原料3代替苯硼酸，其中使用的主要原料、合成的中间体及其收率如表4所示。
表4
Figure PCTCN2022088662-appb-000037
Figure PCTCN2022088662-appb-000038
5.IM A3-1的合成
Figure PCTCN2022088662-appb-000039
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IMA2-1(14.5g，31.84mmol)、联硼酸频那醇酯(8.09g，31.84mmol)、三(二亚苄基丙酮)二钯(0.29g，0.32mmol)、2-二环己基膦-2',4',6'-三异丙基联苯(0.3g，0.67mmol)、醋酸钾(4.69g，47.76mmol)和1,4-二氧六环(87mL)，升温至80℃，搅拌反应3.5h，反应结束后，冷却至室温。萃取反应液，收集有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，得到粗品；使用甲苯体系对粗品进行重结晶提纯，得到IMA3-1(12.5g，收率78.2％)。
参照IM A3-1的合成方法合成表5所示的IM A3-X，不同之处在于，使用原料4代替IM A2-1，其中使用的主要原料、合成的中间体及其收率如表5所示。
表5
Figure PCTCN2022088662-appb-000040
Figure PCTCN2022088662-appb-000041
6.IM A4-1的合成
Figure PCTCN2022088662-appb-000042
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IMA3-1(11.90g，23.68mmol)、对氯碘苯(5.66g，23.68mmol)、碳酸钾(4.90g，35.52mmol)、四(三苯基膦)钯(0.27g，0.24mmol)和四丁基溴化铵(0.13g，0.47mmol)，并加入四氢呋喃(72mL)和水(24mL)的混合溶剂。开启搅拌，回流反应7h，反应结束后，冷却至室温。用二氯甲烷(800mL)萃取分离有机相，合并有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，使用正庚烷作为流动相对粗品进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷体系进行重结晶提纯，得到白色固体IM A4-1(7.5g，收率65％)。
参照IM A4-1的合成方法合成表6所示的IMA4-X，不同之处在于，使用IMA3-X代替IMA3-1，使用原料5代替对氯碘苯，其中使用的主要的原料、合成的中间体及其收率如表6所示。
表6
Figure PCTCN2022088662-appb-000043
Figure PCTCN2022088662-appb-000044
7.IM A5-1的合成
Figure PCTCN2022088662-appb-000045
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IMA2-1(7.50g，16.47mmol)、4-氨基联苯(2.79g，16.47mmol)、甲苯(75mL)、叔丁醇钠(2.37g，24.70mmol)、2-二环己基膦-2’,4’,6’-三异丙基联苯(0.16g，0.3293mmol)和三(二亚苄基丙酮)二钯(0.16g，0.1647mmol)，加热至108℃，搅拌反应1h，停止反应，反应液冷却至室温。用甲苯萃取分离有机相，水洗至中性，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到白色固体IM A5-1(7.08g，产率82％)。
参照IM A5-1的合成方法合成表7所示的IM A5-X，不同之处在于，使用原料6代替IM A2-1，使用原料7代替4-氨基联苯，其中使用的主要原料、合成的中间体及其收率如表7所示。 表7
Figure PCTCN2022088662-appb-000046
Figure PCTCN2022088662-appb-000047
Figure PCTCN2022088662-appb-000048
Figure PCTCN2022088662-appb-000049
8.化合物262的合成
Figure PCTCN2022088662-appb-000050
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入IMA5-1(6.7g，12.32mmol)、4-溴联苯(2.87g，12.32mmol)、甲苯(67mL)、叔丁醇钠(1.78g，18.48mmol)、2-二环己基膦-2',4',6'-三异丙基联苯(0.10g，0.2464mmol)和三(二亚苄基丙酮)二钯(0.11g，0.1232mmol)，加热至108℃，搅拌反应2h，停止反应，反应液冷却至室温。用甲苯萃取分离有机相，水洗至中性，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂；使用 甲苯体系对粗品进行重结晶提纯，得到白色固体化合物262(5.24g，产率61.1％)，质谱(m/z)＝696.4[M+H] +。
参照化合物262的合成方法合成表8所列的化合物X，不同之处在于，使用IM A5-X代替IM A5-1，使用原料8代替4-溴联苯，其中使用的主要原料、合成的化合物及其收率和质谱如表8所示。
表8
Figure PCTCN2022088662-appb-000051
Figure PCTCN2022088662-appb-000052
Figure PCTCN2022088662-appb-000053
Figure PCTCN2022088662-appb-000054
Figure PCTCN2022088662-appb-000055
部分化合物核磁数据如表9所示：
表9
Figure PCTCN2022088662-appb-000056
有机电致发光器件的制备和性能评估
实施例1
红色有机电致发光器件
通过以下过程制备有机电致发光器件：将厚度为
Figure PCTCN2022088662-appb-000057
的阳极100ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2∶N 2等离子进行表面处理，以增加阳极(实验基板)的功函数，并采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的浮渣及油污。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2022088662-appb-000058
的空穴注入层(HIL)；并在空穴注入层上真空蒸镀NPB，以形成厚度为
Figure PCTCN2022088662-appb-000059
的空穴传输层(HTL)。
在空穴传输层上真空蒸镀化合物262，形成厚度为
Figure PCTCN2022088662-appb-000060
的空穴调整层。
在空穴调整层上，将CBP和Ir(piq) 2(acac)以97％∶3％的膜厚比进行共同蒸镀，形成厚度为
Figure PCTCN2022088662-appb-000061
的有机发光层(EML)。
在有机发光层上，将ET-06和LiQ以1∶1的膜厚比进行蒸镀形成厚度为
Figure PCTCN2022088662-appb-000062
的电子传输层(ETL)，接着将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2022088662-appb-000063
的电子注入层(EIL)。
将镁(Mg)和银(Ag)以1∶9的膜厚比真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2022088662-appb-000064
的阴极200。
此外，在上述阴极上蒸镀CP-05形成厚度为
Figure PCTCN2022088662-appb-000065
的有机覆盖层(CPL)，从而完成有机电致发光器件的制造。
实施例2～33
除了在形成空穴调整层时，采用表11记载的其余化合物替代化合物262以外，采用与实施例1相同的方法制作有机电致发光器件。
比较例1～2
在比较例1～2中，除了在形成空穴调整层时，分别采用化合物A、化合物B替代化合物262以外，采用与实施例1相同的方法制作有机电致发光器件。
以上实施例和比较例中，所使用的主要材料的结构如表10所示。
表10
Figure PCTCN2022088662-appb-000066
实施例和比较例所制得的有机电致发光器件的性能见表11，其中，IVL数据是在电流密度为10mA/cm 2的条件下进行测试，T95寿命是在电流密度为20mA/cm 2的条件下进行测试。
表11
Figure PCTCN2022088662-appb-000067
Figure PCTCN2022088662-appb-000068
根据表11的结果可知，在本申请的有机化合物作为空穴调整层的OLED器件中，与比较例相比，实施例1～33制备的有机电致发光器件的各项性能均有所提高。其中，采用本申请的有机化合物作为空穴调整层所对应的器件实施例1～33与现有技术中的化合物所对应的器件比较例1～2相比，有机电致发光器件的驱动电压至少降低了9.7％，电流效率(Cd/A)至少提高了13.4％，功率效率(lm/W)至少提高了12.1％，外量子效率至少提高了14％，寿命最少提高了9％，最高的寿命可提高68h。由上述数据可知，采用本申请的有机化合物作为电子元件的空穴调整层，该电子元件的发光效率(Cd/A)和寿命(T95)都有显著的提高。
前述变形形式和修改形式落在本申请的范围内。应可理解的是，本说明书公开和限定的本申请延伸到文中和/或附图中提到或明显的两个或两个以上单独特征的所有可替代组合。所有这些不同的组合构成本申请的多个可替代方面。本说明书所述的实施方式说明了己知用于实现本申请的最佳方式，并且将使本领域技术人员能够利用本申请。
以上实施例仅用以说明本申请的技术方案，而非对其限制。尽管参照前述实施例对本申请进行了详细的说明，本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本申请各实施例技术方案的精神和范围。

Claims (14)

  1. 有机化合物，其特征在于，所述有机化合物的结构如式1所示：
    Figure PCTCN2022088662-appb-100001
    其中，
    Figure PCTCN2022088662-appb-100002
    表示化学键，
    R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9相同或不同，且各自独立地选自式2所示的结构、氢、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基，且R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9中任一者选自式2所示结构；任选地，R 5和R 6相互连接形成取代或未取代的苯环，所述苯环上的取代基选自式2所示的结构、氘、卤素基团、氰基、碳原子数为1～10的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基或碳原子数为3～12的三烷基硅基；
    L、L 1和L 2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、或者碳原子数为3～30的取代或未取代的亚杂芳基；
    Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
    L、L 1、L 2、Ar 1和Ar 2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为1～5的烷基、碳原子数为3～12的三烷基硅基或三苯基硅基；任选地，Ar 1中的任意两个相邻的取代基形成饱和或不饱和的3～15元环；任选地，Ar 2中的任意两个相邻的取代基形成饱和或不饱和的3～15元环。
  2. 根据权利要求1所述的有机化合物，其中，R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9各自独立地选自式2所示的结构、氢、氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基或三甲基硅基，且R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8和R 9中任一者选自式2所示结构；任选地，R 5和R 6相互连接形成取代或未取代的苯环，所述苯环上的取代基选自式2所示的结构、氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、二苯并噻吩基或三甲基硅基。
  3. 根据权利要求1所述的有机化合物，其中，L、L 1和L 2各自独立地选自单键、碳原子数为6～12的取代或未取代的芳基、碳原子数为5～18的取代或未取代的杂芳基。
  4. 根据权利要求1所述的有机化合物，其中，L、L 1和L 2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基；
    可选地，L、L 1和L 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基或萘基。
  5. 根据权利要求1所述的有机化合物，其中，L、L 1和L 2各自独立地选自单键或者取代或未取代的基团V，未取代的基团V选自如下基团所组成的组：
    Figure PCTCN2022088662-appb-100003
    取代的基团V上具有一个或两个以上取代基，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、苯基或萘基；当取代基个数大于1时，各取代基相同或不同。
  6. 根据权利要求1所述的有机化合物，其中，L、L 1和L 2各自独立地选自单键或者如下基团所组成的组：
    Figure PCTCN2022088662-appb-100004
  7. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自碳原子数为6～25的取代或未取代的芳基或者碳原子数为12～20的取代或未取代的杂芳基；
    优选地，Ar 1和Ar 2中的取代基分别独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基、三甲基硅基或三苯基硅基；任选地，在Ar 1中的任意两个相邻的取代基形成饱和或不饱和的5～13元环；任选地，在Ar 2中的任意两个相邻的取代基形成饱和或不饱和的5～13元环。
  8. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的螺二芴基；
    优选地，Ar 1和Ar 2中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、三甲基硅基或三苯基硅基；任选地，在Ar 1中的任意两个相邻的取代基形成芴环；任选地，在Ar 2中的任意两个相邻的取代基形成芴环。
  9. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自取代或未取代的基团W，未取代的基团W选自如下基团所组成的组：
    Figure PCTCN2022088662-appb-100005
    取代的基团W上具有一个或两个以上的取代基，所述取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、三甲基硅基或三苯基硅基；当取代基个数大于1时，各取代基相同或不同。
  10. 根据权利要求1所述的有机化合物，其中，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
    Figure PCTCN2022088662-appb-100006
    Figure PCTCN2022088662-appb-100007
  11. 根据权利要求1所述的有机化合物，其中，所述有机化合物选自如下化合物所形成的组：
    Figure PCTCN2022088662-appb-100008
    Figure PCTCN2022088662-appb-100009
    Figure PCTCN2022088662-appb-100010
    Figure PCTCN2022088662-appb-100011
    Figure PCTCN2022088662-appb-100012
    Figure PCTCN2022088662-appb-100013
    Figure PCTCN2022088662-appb-100014
    Figure PCTCN2022088662-appb-100015
    Figure PCTCN2022088662-appb-100016
    Figure PCTCN2022088662-appb-100017
    Figure PCTCN2022088662-appb-100018
  12. 电子元件，其特征在于，所述电子元件包括相对设置的阳极和阴极、以及介于所述阳极与阴极之间的功能层，所述功能层包含权利要求1～11中任一项所述的有机化合物；
    优选地，所述功能层包括空穴调整层，所述空穴调整层包括所述有机化合物。
  13. 根据权利要求12所述的电子元件，其中，所述电子元件为有机电致发光器件或光电转化器件；
    优选地，所述有机电致发光器件为红色有机电致发光器件。
  14. 电子装置，其特征在于，包括权利要求12或13所述的电子元件。
PCT/CN2022/088662 2021-05-07 2022-04-24 有机化合物及包含其的电子元件和电子装置 WO2022233243A1 (zh)

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