WO2022206493A1 - 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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WO2022206493A1
WO2022206493A1 PCT/CN2022/082291 CN2022082291W WO2022206493A1 WO 2022206493 A1 WO2022206493 A1 WO 2022206493A1 CN 2022082291 W CN2022082291 W CN 2022082291W WO 2022206493 A1 WO2022206493 A1 WO 2022206493A1
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group
substituted
carbon atoms
unsubstituted
organic compound
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PCT/CN2022/082291
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French (fr)
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马林楠
南朋
金荣国
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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Priority to US18/003,141 priority Critical patent/US20230322656A1/en
Publication of WO2022206493A1 publication Critical patent/WO2022206493A1/zh

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    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present application relates to the technical field of organic electroluminescence, and in particular, to an organic compound and electronic components and electronic devices containing the same.
  • This type of electronic device usually includes a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence.
  • an electric field is generated between the two electrodes.
  • the electrons on the cathode side move to the organic light-emitting layer, and the holes on the anode side also move to the organic light-emitting layer.
  • the electrons and holes combine in the organic light-emitting layer to form Excitons, excitons are in an excited state to release energy to the outside, thereby causing the organic light-emitting layer to emit light to the outside.
  • the electron blocking layer is used to block the electrons transmitted from the organic light-emitting layer, thereby ensuring that the electrons and holes can be efficiently recombined in the organic light-emitting layer; at the same time, the electron blocking layer can also block the organic light-emitting layer.
  • Excitons can reduce the triplet quenching of excitons, thereby ensuring the luminous efficiency of organic electroluminescent devices.
  • the material of the electron blocking layer has a relatively high LUMO value, which can effectively block the transport and diffusion of electrons and excitons from the organic light-emitting layer to the anode direction.
  • the purpose of the present application is to provide an organic compound and an electronic component and electronic device containing the same, and the use of the organic compound in an organic electroluminescence device can improve the luminous efficiency of the device and prolong the life of the device.
  • a first aspect of the present application provides an organic compound whose structure is shown in formula 1:
  • Ar 1 is selected from any one of formula I, formula II and formula III:
  • X is selected from C(R 1 R 2 ), O, S, N(R 3 ) or Si(R 4 R 5 );
  • R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are represented by R i , n 6 , n 7 , n 8 , n 9 , n 10 , and n 11 are represented by ni , and ni is represented by R i Number, i is a variable, representing 6, 7, 8, 9, 10 and 11, when i is 6, 8, 10, n i is selected from 0, 1, 2, 3, 4, 5 or 6; When it is 7, 9, 11, n i is selected from 0, 1, 2 or 3, 4; and when n i is greater than 1, any two R i are the same or different;
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • 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 20 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 20 carbon atoms.
  • the substituents in L 1 , L 2 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, and alkyl group having 3-12 carbon atoms.
  • the organic compound of the present application is a core structure formed by combining a 1,8-diphenyl substituted naphthyl group with a condensed aromatic hydrocarbon and a triarylamine structure.
  • the 1,8-diphenyl-substituted naphthyl can make the hole transport layer to transfer holes more smoothly to the organic light-emitting layer, thus making the organic compound have good hole transport efficiency, effectively improving the electronic components using the organic compound.
  • voltage performance and efficiency performance at the same time, the introduction of 1,8-diphenyl-substituted naphthyl groups changes the conjugate plane of the compound, which may cause molecular crystallization, thereby reducing the lifetime of the device.
  • the triarylamine structure has good hole transport properties, and with 1,8-diphenyl substituted naphthyl, with fused aromatic hydrocarbons, the molecular rigidity is increased, the thermal stability is significantly improved, and the structure can be maintained at high temperatures for a long time. stable, thereby improving the luminous efficiency of organic electroluminescent devices and the power generation efficiency of photoelectric conversion devices.
  • the organic compound of the present application has better hole transport performance, lower intermolecular stacking effect and better film-forming performance, and can improve the efficiency performance and life performance of electronic components such as photoelectric conversion devices and electroluminescent devices.
  • a second aspect of the present application provides an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the above-mentioned organic compound.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • anode 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 330, electron blocking layer; 340, organic electroluminescence layer; 350, electron transport layer; 360, electron An injection layer; 400, an electronic device.
  • the application provides an organic compound whose structure is shown in formula 1:
  • Ar 1 is selected from any one of formula I, formula II and formula III:
  • X is selected from C(R 1 R 2 ), O, S, N(R 3 ) or Si(R 4 R 5 );
  • R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different, and are independently selected from alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aryl groups having 6 to 12 carbon atoms. 3-12 heteroaryl; alternatively, R 1 and R 2 form a saturated or unsaturated 5-13-membered ring; alternatively, R 4 and R 5 form a saturated or unsaturated 5-13-membered ring;
  • R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, and carbon atom number is a trialkylsilyl group of 3 to 12, an aryl group of 6 to 12 carbon atoms, and a heteroaryl group of 3 to 12 carbon atoms;
  • R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are represented by R i , n 6 , n 7 , n 8 , n 9 , n 10 , and n 11 are represented by ni , and ni is represented by R i Number, i is a variable, representing 6, 7, 8, 9, 10 and 11, when i is 6, 8, 10, n i is selected from 0, 1, 2, 3, 4, 5 or 6; When it is 7, 9, 11, n i is selected from 0, 1, 2 or 3, 4; and when n i is greater than 1, any two R i are the same or different;
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 6-40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • 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 20 carbon atoms, or a substituted or unsubstituted arylene group having 3 to 20 carbon atoms.
  • the substituents in L 1 , L 2 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, and alkyl group having 3-12 carbon atoms.
  • any two adjacent substituents in Ar 2 form a saturated or unsaturated 3-15-membered ring
  • any two adjacent substituents in Ar 1 and Ar 2 can be A saturated or unsaturated 3- to 15-membered ring may be formed, and a saturated or unsaturated 3- to 15-membered ring may not be formed.
  • each q is independently 0, 1, 2 or 3
  • each R is independently selected from hydrogen, deuterium, fluorine, chlorine
  • 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.
  • substituents namely Rc
  • Rc can be, for example, deuterium, halogen, cyano, heteroaryl, aryl, alkyl, haloalkyl, cycloalkyl, alkoxy, trialkylsilyl, optionally, any two
  • substituents are interconnected to form, together with the atoms to which they are attached, a 3- to 15-membered saturated or unsaturated ring.
  • the "substituted" functional group may be substituted by one or more of the above-mentioned Rc substituents; 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 the number of all carbon atoms. For example, if L 1 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. For example: Ar 1 is Then the number of carbon atoms is 10; L 1 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.
  • 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 include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10]phenanthrenyl base, pyrenyl, benzofluoranthene, Base et al.
  • biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • 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.
  • a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5, 6, 7 or more heteroatoms in the ring, and the heteroatoms may be B, O One or more of , N, P, 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.
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • 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 means that one or more than two hydrogen atoms in the heteroaryl group are 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 and other groups. It should be understood that 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, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxaline base, isoquinolinyl.
  • halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • haloalkyl examples include, but are not limited to, trifluoromethyl and the like.
  • 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.
  • 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):
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-12 carbon atoms.
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12 carbon atoms.
  • L 1 and L 2 are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.
  • the substituents in L 1 and L 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl.
  • 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, phenyl , naphthyl, pyridyl; when the number of substituents is greater than 1, the substituents are the same or different.
  • L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • L 1 and L 2 are each independently selected from the group consisting of a single bond or the following groups:
  • Ar 2 is selected from a substituted or unsubstituted aryl group with 6-25 carbon atoms, or a substituted or unsubstituted heteroaryl group with 3-20 carbon atoms.
  • Ar 2 is selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 substituted or unsubstituted aryl, or selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 substituted or unsubstituted heteroaryl.
  • the substituents in Ar 2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, carbon Heteroaryl having 3-12 atoms; optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 5-13-membered ring.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzofuranyl Benzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted carbazolyl.
  • the substituents in Ar 2 are each independently selected from deuterium, cyano, fluorine, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl , pyridyl; optionally, any two adjacent substituents in Ar 2 form a fluorene ring.
  • Ar is selected from substituted or unsubstituted group W, and unsubstituted group W is selected from the group consisting of:
  • the substituted group W has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group; when the number of substituent groups is greater than 1, each substituent group is the same or different.
  • Ar is selected from the group consisting of :
  • Ar 2 is selected from the group consisting of the following groups:
  • R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, bi phenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl ; alternatively, R and R form cyclopentane, cyclohexane or fluorene ring; alternatively, R 4 and R 5 form a cyclopentane, cyclohexane or fluorene ring.
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethyl Silicon, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
  • Ar 1 is selected from substituted or unsubstituted group Q, and unsubstituted group Q is selected from the group consisting of:
  • the substituted group Q has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, phenyl , naphthyl, biphenyl, pyridyl, cyclohexyl, carbazolyl, trimethylsilyl; when the number of substituents is greater than 1, the substituents are the same or different.
  • Ar 1 is selected from the group consisting of:
  • the organic compound is selected from the group consisting of:
  • the present application provides an electronic component.
  • the electronic component includes an anode and a cathode disposed oppositely, and a functional layer interposed between the anode and the cathode, the functional layer containing the organic compound of the present application.
  • the functional layer includes an electron blocking layer, and the electron blocking layer includes the organic compound.
  • the electronic element is an organic electroluminescence device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescence device.
  • the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer.
  • the functional layer 300 includes a hole transport layer 320, The electron blocking layer 330, the organic electroluminescent layer 340, and the electron transport layer 350; the hole transport layer 320, the electron blocking layer 330, the organic electroluminescent layer 340, the electron transport layer 350, and the electron injection layer 360 can be sequentially formed on the anode 100
  • the electron blocking layer 330 may contain the organic compound described in the first aspect of the present application, preferably at least one of the compounds 1-450.
  • 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-(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 includes one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, to which this application applies No special restrictions are made.
  • the hole transport layer 320 is NPB.
  • the electron blocking layer 330 is used to block the electrons transmitted from the organic light emitting layer 340 , thereby ensuring that electrons and holes can be recombined in the organic light emitting layer 340 efficiently; at the same time, the electron blocking layer 330 can also block the organic light emitting layer 340
  • the diffused excitons reduce the triplet quenching of the excitons, thereby ensuring the luminous efficiency of the organic electroluminescent device.
  • the compound of the electron blocking layer 340 has a relatively high LUMO value, which can effectively block the transmission and diffusion of electrons and excitons from the organic light-emitting layer 340 to the anode 110 .
  • the electron blocking layer 340 includes the organic compound of the present application.
  • the material of the organic electroluminescent 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 organic electroluminescent layer 340 is composed of BH-01 and BD-01.
  • 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 composed of F4-TCNQ.
  • the present application provides an electronic device including the electronic component provided in the second aspect of the present application.
  • the present application provides an electronic device 400 , and the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the electronic device 400 may be a display device, a lighting device, an optical communication device or other types of electronic equipment, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • Extract and separate the organic phase with toluene, wash with water until neutral, dry the organic phase with anhydrous magnesium sulfate, filter and concentrate the filtrate under reduced pressure; use ethyl acetate/n-heptane system to purify the crude product by silica gel chromatography, concentrate, and then use The toluene/n-heptane system was recrystallized to obtain compound 2 (17 g, yield 81.3%) as a white solid, mass spectrum (m/z) 670.31 [M+H] + .
  • Organic electroluminescent devices were prepared by the following procedure:
  • HIL The hole injection layer
  • HTL The hole transport layer
  • Compound 2 was vacuum evaporated on the hole transport layer (HTL) to form a thickness of The electron blocking layer (EBL).
  • EML organic electroluminescent layer
  • ET-06 and LiQ were evaporated at a weight ratio of 1:1 to form a thickness of The electron transport layer (ETL).
  • Yb was evaporated on the electron transport layer (ETL) to form a thickness of Then, on the electron injection layer (EIL), magnesium (Mg) and silver (Ag) were evaporated at a rate of 1:9 to form a thickness of the cathode.
  • ETL electron transport layer
  • EIL electron injection layer
  • Mg magnesium
  • Ag silver
  • a blue organic electroluminescent device was fabricated by the same method as in Example 1, except that the other compounds described in Table 6 were used instead of Compound 2 in the electron blocking layer (EBL).
  • EBL electron blocking layer
  • the driving voltage of the organic electroluminescent devices in Examples 1 to 40 using the organic compound of the present application as the electron blocking layer is higher than that of Comparative Examples 1 to 4 corresponding to the known compounds. At least 0.12V is reduced, the luminous efficiency (Cd/A) is increased by at least 13.4%, the external quantum efficiency is increased by at least 13.4%, and the lifetime is increased by at least 26.4%. Therefore, the organic compound of the present application has the characteristics of improving both the luminous efficiency and the lifetime. It can be seen from the above data that the luminous efficiency (Cd/A), external quantum efficiency (EQE) and lifetime (T95) of the electronic device are significantly improved by using the organic compound of the present application as the electron blocking layer of the electronic device. Therefore, using the organic compound of the present application in the electron blocking layer can prepare an organic electroluminescent device with high luminous efficiency and long lifetime.

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Abstract

本申请涉及一种有机化合物及包含其电子元件和电子装置，属于有机电致发光技术领域。本申请的有机化合物的结构如式1所示，将该有机化合物应用于电子元件中，可显著改善电子元件的性能。

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4月2日递交的申请号为202110362511.8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
本申请涉及有机电致发光技术领域，具体而言，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
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子器件的应用范围越来越广泛。该类电子器件通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
以有机电致发光器件为例，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的有机发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向有机发光层移动，阳极侧的空穴也向有机发光层移动，电子和空穴在有机发光层结合形成激子，激子处于激发态向外释放能量，进而使得有机发光层对外发光。
有机发光器件结构中，电子阻挡层用于阻挡有机发光层传输过来的电子，进而保证电子和空穴能够很高效地在有机发光层复合；同时，电子阻挡层还可以阻挡有机发光层扩散过来的激子，减少激子的三线态淬灭，进而保证有机电致发光器件的发光效率。电子阻挡层的材料具有比较高的LUMO值，其可以有效阻挡电子和激子从有机发光层向阳极方向的传输和扩散。随着市场的不断发展，对器件的发光效率、使用寿命等性能的要求越来越高，开发稳定高效的电子阻挡层材料，从而降低驱动电压，提高器件发光效率，延长器件寿命，具有很重要的实际应用价值。
发明内容
本申请的目的在于提供一种有机化合物及包含其的电子元件和电子装置，将所述有机化合物用于有机电致发光器件可提高器件的发光效率并延长器件的寿命。
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 PCTCN2022082291-appb-000001
其中，Ar 1选自式I、式II和式III中的任一个：
Figure PCTCN2022082291-appb-000002
其中，
Figure PCTCN2022082291-appb-000003
表示化学键；
X选自C(R 1R 2)、O、S、N(R 3)或Si(R 4R 5)；
R 1、R 2、R 3、R 4、R 5相同或不同，且各自独立地选自碳原子数为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；或者，R 1和R 2形成饱和或不饱和的5～13元环；或者，R 4和R 5形成饱和或不饱和的5～13元环；
R 6、R 7、R 8、R 9、R 10、R 11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1～5的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基；
R 6、R 7、R 8、R 9、R 10、R 11以R i表示，n 6、n 7、n 8、n 9、n 10、n 11以n i表示，n i表示R i的个数，i为变量，表示6、7、8、9、10和11，当i为6、8、10时，n i选自0、1、2、3、4、5或6；当i为7、9、11时，n i选自0、1、2或3、4；且当n i大于1时，任意两个R i相同或不同；
Ar 2选自碳原子数为6～40的取代或未取代的芳基、或者碳原子数为3～30的取代或未取代的杂芳基；
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6～20的取代或未取代的亚芳基、或者碳原子数为3～20的取代或未取代的亚杂芳基；
L 1、L 2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1～10的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷氧基；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。
本申请的有机化合物是1,8-二苯基取代的萘基与稠合芳烃及三芳胺结构结合形成的核心结构。1,8-二苯基取代的萘基可以使得空穴传输层向有机发光层传递空穴更为顺畅，因此使得有机化合物具有良好的空穴传输效率，有效改善使用该有机化合物的电子元件的电压性能与效率性能；同时，1,8-二苯基取代的萘基的引入，改变了化合物的共轭平面，有可能引起分子结晶，从而导致器件的寿命降低，因此为了克服1,8-二苯基取代的萘基所带来的不利影响，向有机化合物引入了大空间位阻，并且具有共轭效应的稠合芳烃，有效改善了有机化合物的结晶效应，提升了有机化合物的成膜效应。三芳胺结构具有良好的空穴传输特性，与1,8-二苯基取代的萘基，带有稠合芳烃键合，分子刚性增加，热稳定性显著提升，能够在长时间高温下保持结构稳定，进而提高有机电致发光器件的发光效率和光电转化器件的发电效率。本申请的有机化合物具有更好的空穴传输性能、更低的分子间堆叠效应和更佳的成膜性能，能够提升光电转化器件和电致发光器件等电子元件的效率性能和寿命性能。
本申请的第二方面提供一种电子元件，包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，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。
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、电子阻挡层；340、有机电致发光层；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个实施方式中。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。
第一方面，本申请提供一种有机化合物，其结构如式1所示：
Figure PCTCN2022082291-appb-000004
其中，Ar 1选自式I、式II和式III中的任一个：
Figure PCTCN2022082291-appb-000005
其中，
Figure PCTCN2022082291-appb-000006
表示化学键；
X选自C(R 1R 2)、O、S、N(R 3)或Si(R 4R 5)；
R 1、R 2、R 3、R 4、R 5相同或不同，且各自独立地选自碳原子数为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；或者，R 1和R 2形成饱和或不饱和的5～13元环；或者，R 4和R 5形成饱和或不饱和的5～13元环；
R 6、R 7、R 8、R 9、R 10、R 11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1～5的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基；
R 6、R 7、R 8、R 9、R 10、R 11以R i表示，n 6、n 7、n 8、n 9、n 10、n 11以n i表示，n i表示R i的个数，i为变量，表示6、7、8、9、10和11，当i为6、8、10时，n i选自0、1、2、3、4、5或6；当i为7、9、11时，n i选自0、1、2或3、4；且当n i大于1时，任意两个R i相同或不同；
Ar 2选自碳原子数为6～40的取代或未取代的芳基、或者碳原子数为3～30的取代或未取代的杂芳基；
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6～20的取代或未取代的亚芳基、或者碳原子数为3～20的取代或未取代的亚杂芳基；
L 1、L 2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1～10的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、 碳原子数为1～10的卤代烷基、碳原子数为1～10的烷氧基；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，举例而言，任意两个相邻的取代基形成芴基等。
本申请中，“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”是指Ar 1和Ar 2中任意两个相邻的取代基可以形成饱和或不饱和的3～15元环，也可以不形成饱和或不饱和的3～15元环。
本申请中，
Figure PCTCN2022082291-appb-000007
是指与其他取代基或结合位置结合的连接键。
本申请中，所采用的描述方式“分别独立地选自”与“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 PCTCN2022082291-appb-000008
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、氰基、杂芳基、芳基、烷基、卤代烷基、环烷基、烷氧基、三烷基硅基，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中的一个或两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，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 1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 PCTCN2022082291-appb-000009
则其碳原子数为10；L 1为
Figure PCTCN2022082291-appb-000010
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。
例如，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 PCTCN2022082291-appb-000011
基等。本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
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、三氟甲基、杂芳基、芳基、三甲基硅基、烷基、环烷基、烷氧基等基团取代。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，杂芳基是指环中包含1、2、3、4、5、6、7个或更多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、苯并噻唑基、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-芳基咔唑基、N-杂芳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，取代的杂芳基是指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，作为取代基的芳基的具体实例包括但不限于，苯基、联苯基、萘基、蒽基、菲基、
Figure PCTCN2022082291-appb-000012
基。
本申请中，作为取代基的杂芳基的具体实例包括但不限于，吡啶基、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、异喹啉基。
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，卤代烷基的具体实例包括但不限于，三氟甲基等。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2022082291-appb-000013
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 PCTCN2022082291-appb-000014
Figure PCTCN2022082291-appb-000015
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 PCTCN2022082291-appb-000016
本申请中，式I、式II和式III中，
Figure PCTCN2022082291-appb-000017
表示化学键，表示该键的一端可以连接在各自所示的苯并二苯五元环的任意位置上，包括可连接在萘环的碳原子上、苯环的碳原子上，还可连接在X上。当
Figure PCTCN2022082291-appb-000018
的一端连接在X上，且X为C(R 1R 2)、N(R 3)或Si(R 4R 5)时，
Figure PCTCN2022082291-appb-000019
的该端具体可连接在R 1、R 2、R 3、R 4或R 5上。举例来讲，当Ar 1为式I所示的基团，且式I中的n 6和n 7均为0，X为N(Ph)时，Ar 1的结构包括以下类型：
Figure PCTCN2022082291-appb-000020
在本申请的一种实施方式中，L 1和L 2各自独立地选自单键、碳原子数为6～12取代或未取代的亚芳基。例如，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取代或未取代的亚芳基。
可选地，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 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、苯基、萘基、吡啶基。
可选地，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选自如下基团组成的组：
Figure PCTCN2022082291-appb-000021
其中，取代的基团V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、吡啶基；当取代基个数大于1时，各取代基相同或不同。
可选地，L 1和L 2各自独立地选自单键或者如下基团组成的组：
Figure PCTCN2022082291-appb-000022
进一步可选地，L 1和L 2各自独立地选自单键或者如下基团组成的组：
Figure PCTCN2022082291-appb-000023
在本申请的一种实施方式中，Ar 2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3～20的取代或未取代的杂芳基。例如，Ar 2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，或者选自碳原子数为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20的取代或未取代的杂芳基。
优选地，Ar 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、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；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 2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、取代或未取代的菲基、取代或未取代的咔唑基。
优选地，Ar 2中的取代基各自独立地选自氘、氰基、氟、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基；任选地，在Ar 2中的任意两个相邻的取代基形成芴环。
可选地，Ar 2选自取代或未取代的基团W，未取代的基团W选自如下基团组成的组：
Figure PCTCN2022082291-appb-000024
其中，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、氰基、氟、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基；当取代基个数大于1时，各取代基相同或不同。
可选地，Ar 2选自如下基团所组成的组：
Figure PCTCN2022082291-appb-000025
进一步可选地，Ar 2选自如下基团组成的组：
Figure PCTCN2022082291-appb-000026
Figure PCTCN2022082291-appb-000027
在本申请的一种实施方式中，R 1、R 2、R 3、R 4和R 5各自独立地选自甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基；或者，R 1和R 2形成环戊烷、环己烷或芴环；或者，R 4和R 5形成环戊烷、环己烷或芴环。
可选地，R 6、R 7、R 8、R 9、R 10、R 11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、萘基、联苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基。
在本申请的一种实施方式中，Ar 1选自取代或未取代的基团Q，未取代的基团Q选自如下基团组成的组：
Figure PCTCN2022082291-appb-000028
其中，取代的基团Q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、氰基、氟、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、环己基、咔唑基、三甲基硅基；当取代基个数大于1时，各取代基相同或不同。
还可选地，Ar 1选自如下基团组成的组：
Figure PCTCN2022082291-appb-000029
可选地，所述有机化合物选自如下化合物组成的组：
Figure PCTCN2022082291-appb-000030
Figure PCTCN2022082291-appb-000031
Figure PCTCN2022082291-appb-000032
Figure PCTCN2022082291-appb-000033
Figure PCTCN2022082291-appb-000034
Figure PCTCN2022082291-appb-000035
Figure PCTCN2022082291-appb-000036
Figure PCTCN2022082291-appb-000037
Figure PCTCN2022082291-appb-000038
Figure PCTCN2022082291-appb-000039
Figure PCTCN2022082291-appb-000040
Figure PCTCN2022082291-appb-000041
Figure PCTCN2022082291-appb-000042
第二方面，本申请提供一种电子元件。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，该功能层包含本申请的有机化合物。
所述功能层包括电子阻挡层，所述电子阻挡层包括所述有机化合物。
可选地，所述电子元件为有机电致发光器件或光电转换器件。
在本申请的一种实施方式中，所述电子元件为有机电致发光器件。如图1所示，本申请的有机电致发光器件包括阳极100、阴极200、以及介于阳极层与阴极层之间的至少一层功能层300，该功能层300包括空穴传输层320、电子阻挡层330、有机电致发光层340、电子传输层350；空穴传输层320、电子阻挡层330、有机电致发光层340、电子传输层350以及电子注入层360可以依次形成在阳极100上，电子阻挡层330可以含有本申请第一方面所述的有机化合物，优选含有化合物1～450中的至少一种。
可选地，阳极100包括以下阳极材料，其优选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-(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。
可选地，空穴传输层320包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。在本申请的一种实施方式中，空穴传输层320为NPB。
可选地，电子阻挡层330用于阻挡有机发光层340传输过来的电子，进而保证电子和空穴能够很高效地在有机发光层340复合；同时，电子阻挡层330还可以阻挡有机发光层340扩散过来的激子，减少激子的三线态淬灭，进而保证有机电致发光器件的发光效率。电子阻挡层340的化合物具有比较高的LUMO值，其可以有效阻挡电子和激子从有机发光层340向阳极110方向的传输和扩散。优选地，电子阻挡层340包含本申请的有机化合物。
有机电致发光层340的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，有机电致发光层340由BH-01和BD-01组成。
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，电子传输层350由ET-06和LiQ组成。
可选地，阴极200包括以下阴极材料，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。举例而言，空穴注入层310由F4-TCNQ组成。
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为Yb。
第三方面，本申请提供一种电子装置，包括本申请第二方面提供的电子元件。
如图2所示，本申请提供一种电子装置400，该电子装置400包括上述有机电致发光器件。该电子装置400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设备，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化合物，且用于制备本申请的化合物的其它方法都被认为是在本申请的范围之内。例如，根据本申请那些非例证的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。另外，本申请所公开的反应或已知的反应条件也公认地适用于本申请其他化合物的制备。
化合物2的合成
1、IM A-1的合成
Figure PCTCN2022082291-appb-000043
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8-苯基-1萘硼酸(100g，0.403mol)、对溴碘苯(103.7g，0.366mol)、K 2CO 3(101.3g，0.733mol)、四丁基溴化铵(2.3g，0.007mol)、Pd(PPh 3) 4(4.2g，0.004mol)、甲苯(600mL)、乙醇(200mL)和水(100mL)，开启搅拌，回流反应12h，反应结束后，冷却至室温。用甲苯萃取分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩；使用二氯甲烷/正庚烷体系对粗品进行硅胶色谱提纯，得到白色固体IMA-1(117.9g，收率90％)。
参照IM A-1的方法合成下表1中所列的IMA-X，不同之处在于，使用原料1代替对溴碘苯，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 PCTCN2022082291-appb-000044
2、IM B-1的合成
Figure PCTCN2022082291-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IMA-1(20g，0.056mol)、4-氨基联苯(9.5g，0.056mol)、甲苯(160mL)，回流搅拌30min，降温至70～80℃；加入叔丁醇钠(10.76g，0.112mol)、X-phos(0.53g，0.001mol)和三(二亚苄基丙酮)二钯(0.4576g，0.0005mol)，待体系温度稳定后，回流反应4h后停止反应，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硅胶色谱提纯，得到白色固体IM B-1(21.3g，收率85％)。
参照IM B-1的方法合成下表2中所列的IM B-X，不同之处在于，使用IM A-X代替IM A-1，使用原料2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2所示。
表2
Figure PCTCN2022082291-appb-000046
Figure PCTCN2022082291-appb-000047
Figure PCTCN2022082291-appb-000048
3、化合物2的合成
Figure PCTCN2022082291-appb-000049
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 B-1(13.6g，30.4mmol)、8-溴-7,7-二甲基-7H-苯并芴(9.8g，30.4mmol)和甲苯溶剂(100mL)，回流搅拌，溶液至澄清，降温至70～80℃；加入叔丁醇钠(4.4g，45.7mmol)、s-Phos(0.25g，0.61mmol)和三(二亚苄基丙酮)二钯(0.28g，0.330mmol)，待体系温度稳定后，回流反应6h后停止反应，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；使用乙酸乙酯/正庚烷体系对粗品进行硅胶色谱提纯，浓缩，再用甲苯/正庚烷体系进行重结晶，得到白色固体化合物2(17g，收率81.3％)，质谱(m/z)＝670.31[M+H] +。
参照化合物2的方法合成下表3所列的化合物，不同之处在于，使用原料3代替8-溴-7,7-二甲基-7H-苯并芴，使用IM B-X代替B-1，其中，使用的主要原料、合成的化合物及其收率和质谱示于表3中。
表3
Figure PCTCN2022082291-appb-000050
Figure PCTCN2022082291-appb-000051
Figure PCTCN2022082291-appb-000052
Figure PCTCN2022082291-appb-000053
Figure PCTCN2022082291-appb-000054
Figure PCTCN2022082291-appb-000055
部分化合物核磁数据如下表4所示。
表4
Figure PCTCN2022082291-appb-000056
有机电致发光器件的制备和性能评估
实施例1
蓝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 PCTCN2022082291-appb-000057
的阳极ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，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)上真空蒸镀化合物F4-TCNQ以形成厚度为
Figure PCTCN2022082291-appb-000058
的空穴注入层(HIL)；并在空穴注入层(HIL)上真空蒸镀化合物NPB，以形成厚度为
Figure PCTCN2022082291-appb-000059
的空穴传输层(HTL)。
在空穴传输层(HTL)上真空蒸镀化合物2形成厚度为
Figure PCTCN2022082291-appb-000060
的电子阻挡层(EBL)。
在电子阻挡层(EBL)上，将BH-01∶BD-01以98％∶2％的蒸镀比进行蒸镀形成厚度为
Figure PCTCN2022082291-appb-000061
的有机电致发光层(EML)。
在有机电致发光层(EML)上，将ET-06和LiQ以1∶1的重量比进行蒸镀形成厚度为
Figure PCTCN2022082291-appb-000062
的电子传输层(ETL)。
在电子传输层(ETL)上蒸镀Yb形成厚度为
Figure PCTCN2022082291-appb-000063
的电子注入层(EIL)，然后在电子注入层(EIL) 上，将镁(Mg)和银(Ag)以1∶9的蒸镀速率进行蒸镀形成厚度为
Figure PCTCN2022082291-appb-000064
的阴极。
在阴极上蒸镀化合物CP-05，形成厚度为
Figure PCTCN2022082291-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2～40
除了在电子阻挡层(EBL)时，采用表6记载的其余化合物替代化合物2以外，采用与实施例1相同的方法制作蓝色有机电致发光器件。
对比例1～4
在对比例1～4中，除了分别使用化合物A、化合物B、化合物C、化合物D替代化合物2形成电子阻挡层(EBL)之外，采用与实施例1相同的方法制作蓝色有机电致发光器件。
以上实施例和对比例中，所采用的主要材料的结构如表5所示：
表5
Figure PCTCN2022082291-appb-000066
实施例和对比例所制备的有机电致发光器件的性能见表6，其中，IVL(电压、效率、色坐标)数据、T95寿命在15mA/cm 2的电流密度下进行测试。
表6
Figure PCTCN2022082291-appb-000067
Figure PCTCN2022082291-appb-000068
Figure PCTCN2022082291-appb-000069
根据上述表6的结果可知，以本申请的有机化合物作为电子阻挡层的的实施例1～40与已公知的化合物所对应的器件对比例1～4相比，有机电致发光器件的驱动电压至少降低了0.12V，发光效率(Cd/A)至少提高了13.4％，外量子效率至少提高了13.4％，寿命最少提高了26.4％。因此本申请的有机化合物具有兼顾提高发光效率及提高寿命的特点。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电子阻挡层，该电子元件的发光效率(Cd/A)、外量子效率(EQE)以及寿命(T95)都有显著的提高。因此，在电子阻挡层中使用本申请的有机化合物可制备得到高发光效率、长寿命的有机电致发光器件。
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 (17)

  1. 有机化合物，所述有机化合物的结构如式1所示：
    Figure PCTCN2022082291-appb-100001
    其中，Ar 1选自式I、式II和式III中的任一个：
    Figure PCTCN2022082291-appb-100002
    其中，
    Figure PCTCN2022082291-appb-100003
    表示化学键；
    X选自C(R 1R 2)、O、S、N(R 3)或Si(R 4R 5)；
    R 1、R 2、R 3、R 4、R 5相同或不同，且各自独立地选自碳原子数为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；或者，R 1和R 2形成饱和或不饱和的5～13元环；或者，R 4和R 5形成饱和或不饱和的5～13元环；
    R 6、R 7、R 8、R 9、R 10、R 11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1～5的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～12的芳基、碳原子数为3～12的杂芳基；
    R 6、R 7、R 8、R 9、R 10、R 11以R i表示，n 6、n 7、n 8、n 9、n 10、n 11以n i表示，n i表示R i的个数，i为变量，表示6、7、8、9、10和11，当i为6、8、10时，n i选自0、1、2、3、4、5或6；当i为7、9、11时，n i选自0、1、2或3、4；且当n i大于1时，任意两个R i相同或不同；
    Ar 2选自碳原子数为6～40的取代或未取代的芳基、或者碳原子数为3～30的取代或未取代的杂芳基；
    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6～20的取代或未取代的亚芳基、或者碳原子数为3～20的取代或未取代的亚杂芳基；
    L 1、L 2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1～10的烷基、碳原子数为3～12的三烷基硅基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷氧基；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，L 1和L 2各自独立地选自单键、碳原子数为6～12取代或未取代的亚芳基。
  3. 根据权利要求1所述的有机化合物，其中，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 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、苯基、萘基、吡啶基。
  4. 根据权利要求1所述的有机化合物，其中，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 PCTCN2022082291-appb-100004
    其中，取代的基团V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、吡啶基；当取代基个数大于1时，各取代基相同或不同。
  5. 根据权利要求1所述的有机化合物，其中，L 1和L 2各自独立地选自单键或者如下基团组成的组：
    Figure PCTCN2022082291-appb-100005
  6. 根据权利要求1所述的有机化合物，其中，Ar 2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3～20的取代或未取代的杂芳基；
    优选地，Ar 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、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；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。
  7. 根据权利要求1所述的有机化合物，其中，Ar 2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、取代或未取代的菲基、取代或未取代的咔唑基；
    优选地，Ar 2中的取代基各自独立地选自氘、氰基、氟、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基；任选地，在Ar 2中的任意两个相邻的取代基形成芴环。
  8. 根据权利要求1所述的有机化合物，其中，Ar 2选自取代或未取代的基团W，未取代的基团W选自如下基团组成的组：
    Figure PCTCN2022082291-appb-100006
    其中，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、氰基、氟、三甲基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基；当取代基个数大于1时，各取代基相同或不同。
  9. 根据权利要求1所述的有机化合物，其中，Ar 2选自如下基团组成的组：
    Figure PCTCN2022082291-appb-100007
    Figure PCTCN2022082291-appb-100008
  10. 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和R 5各自独立地选自甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基；或者，R 1和R 2形成环戊烷、环己烷或芴环；或者，R 4和R 5形成环戊烷、环己烷或芴环。
  11. 根据权利要求1所述的有机化合物，其中，R 6、R 7、R 8、R 9、R 10、R 11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、萘基、联苯基、吡啶基、嘧啶基、喹啉基、异喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基。
  12. 根据权利要求1所述的有机化合物，其中，Ar 1选自取代或未取代的基团Q，未取代的基团Q选自如下基团组成的组：
    Figure PCTCN2022082291-appb-100009
    其中，取代的基团Q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、氰基、氟、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、环己基、咔唑基、三甲基硅基；当取代基个数大于1时，各取代基相同或不同。
  13. 根据权利要求1所述的有机化合物，其中，Ar 1选自如下基团组成的组：
    Figure PCTCN2022082291-appb-100010
  14. 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组成的组：
    Figure PCTCN2022082291-appb-100011
    Figure PCTCN2022082291-appb-100012
    Figure PCTCN2022082291-appb-100013
    Figure PCTCN2022082291-appb-100014
    Figure PCTCN2022082291-appb-100015
    Figure PCTCN2022082291-appb-100016
    Figure PCTCN2022082291-appb-100017
    Figure PCTCN2022082291-appb-100018
    Figure PCTCN2022082291-appb-100019
    Figure PCTCN2022082291-appb-100020
    Figure PCTCN2022082291-appb-100021
    Figure PCTCN2022082291-appb-100022
    Figure PCTCN2022082291-appb-100023
  15. 电子元件，包括阳极、阴极、以及介于阳极与阴极之间的功能层，所述功能层包含权利要求1～14中任一项所述的有机化合物；
    优选地，所述功能层包括电子阻挡层，所述电子阻挡层包括所述有机化合物。
  16. 根据权利要求15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换器件。
  17. 电子装置，包括权利要求15或16所述的电子元件。
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