WO2022262365A1 - 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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WO2022262365A1
WO2022262365A1 PCT/CN2022/084478 CN2022084478W WO2022262365A1 WO 2022262365 A1 WO2022262365 A1 WO 2022262365A1 CN 2022084478 W CN2022084478 W CN 2022084478W WO 2022262365 A1 WO2022262365 A1 WO 2022262365A1
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substituted
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carbon atoms
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贾志艳
刘云
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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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the application belongs to the technical field of organic materials, and in particular relates to an organic compound and electronic components and electronic devices containing the same.
  • Organic electroluminescent device technology is regarded as the next generation of display and lighting technology due to its advantages such as active light emission, high luminous efficiency, low power consumption, light weight, thinness, fast response speed, and large viewing angle.
  • An organic electroluminescent device consists of a substrate, an anode, a hole injection layer, a hole transport layer and an electron blocking layer, a light emitting layer, an electron transport layer and a hole blocking layer, an electron injection layer, and a cathode. Electrons and holes are injected from the cathode and anode respectively, and then recombine in the light-emitting layer through the electron transport layer and the hole transport layer to form excitons, and the excitons return to the ground state to emit light.
  • the materials forming the organic layer in the device such as hole injection layer material, hole transport layer material and electron blocking layer material, light-emitting layer material, Electron transport layer materials, hole blocking layer materials, electron injection layer materials, etc. are supported by stable and efficient materials.
  • the organic electroluminescent element when driven or stored in a high-temperature environment, the organic electroluminescent element has adverse effects such as a change in light color, a decrease in luminous efficiency, an increase in driving voltage, and a shortening of the luminous lifetime.
  • it is necessary to raise the glass transition temperature of the hole transport layer material.
  • the currently reported hole transport layer materials generally have a small molecular weight, and the glass transition temperature of the material is low; during the use of the material, repeated charge and discharge will make the material easy to crystallize and the uniformity of the film will be destroyed, thereby affecting the service life of the material.
  • the purpose of the present application is to provide an organic compound and electronic components and electronic devices containing it.
  • the organic compound can be used in organic electroluminescence devices to improve the performance of the components.
  • the first aspect of the present application provides an organic compound having a structure represented by Formula 1:
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium or methyl;
  • n is selected from 1 or 2;
  • Ar is selected from substituted or unsubstituted aryl groups with 9 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 9 to 30 carbon atoms;
  • Ar is selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
  • L, L1, and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted arylene group with 3 to 30 carbon atoms.
  • heteroarylene
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, trialkylsilyl group with 3 to 12 carbon atoms, Haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkyl groups with 1 to 10 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and 6 to 20 substituted or unsubstituted aryl groups, the substituents in the aryl group are selected from deuterium, halogen groups, cyano groups, and alkyl groups with 1 to 10 carbon atoms; optionally, any of Ar 2 Two adjacent substituents form a substituted or unsubstituted 3-15-membered ring, and the substituents of the 3-15-membered ring are selected from alkyl groups with 1-10 carbon atoms.
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and each is independently selected from deuterium, halogen group, cyano group, trialkyl with 3 to 12 carbon atoms Silicon group, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, carbon A heteroaryl group with 3 to 20 atoms;
  • any two adjacent substituents in Ar 2 form a substituted or unsubstituted 3 to 15 membered ring, and the substituents of the 3 to 15 membered ring are selected from An alkyl group having 1 to 10 carbon atoms.
  • the 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 disposed between the anode and the cathode; the functional layer includes the above-mentioned organic compound.
  • a third aspect of the present application provides an electronic device, including the above-mentioned electronic component.
  • a specific benzo five-membered/six-membered ring is combined into the triarylamine, and one of the substituents of the triarylamine is controlled to have a larger molecular structure.
  • the spatial configuration of the molecule is more three-dimensional, Thereby improving the T1 level can effectively block the diffusion of excitons and improve the life of the device (OLED); on the other hand, such a specific structure has better hole mobility and improves the gap between the hole transport layer and the organic layer. The matching between them can effectively improve the efficiency of the device (OLED).
  • Fig. 1 is a schematic structural view of an organic electroluminescence device according to an embodiment of the present application.
  • Fig. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
  • Fig. 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • Fig. 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.
  • Electron transport layer 350 Electron injection layer 360. Photoelectric conversion layer 400.
  • Example embodiments will now be described more fully with reference to the accompanying drawings.
  • Example embodiments may, however, be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be thorough and complete and will fully convey the concept of example embodiments communicated to those skilled in the art.
  • the described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided in order to give a thorough understanding of embodiments of the present application.
  • the present application provides an organic compound having a structure represented by Formula 1:
  • R 1 and R 2 are the same or different, and are each independently selected from hydrogen, deuterium or methyl;
  • n is selected from 1 or 2;
  • Ar is selected from substituted or unsubstituted aryl groups with 9 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 9 to 30 carbon atoms;
  • Ar is selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
  • L, L1, and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted arylene group with 3 to 30 carbon atoms.
  • heteroarylene
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, trialkylsilyl group with 3 to 12 carbon atoms, Haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, alkyl groups with 1 to 10 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms, and 6 to 20 substituted or unsubstituted aryl groups, the substituents in the aryl group are selected from deuterium, halogen groups, cyano groups, and alkyl groups with 1 to 10 carbon atoms; optionally, any of Ar 2 Two adjacent substituents form a substituted or unsubstituted 3-15-membered ring, and the substituents of the 3-15-membered ring are selected from alkyl groups with 1-10 carbon atoms.
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and each is independently selected from deuterium, halogen group, cyano group, trialkyl with 3 to 12 carbon atoms Silicon group, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 20 carbon atoms, carbon A heteroaryl group with 3 to 20 atoms;
  • any two adjacent substituents in Ar 2 form a substituted or unsubstituted 3 to 15 membered ring, and the substituents of the 3 to 15 membered ring are selected from An alkyl group having 1 to 10 carbon atoms.
  • any two adjacent substituents XX form a ring means that these two substituents can form a ring but not necessarily form a ring, including: the situation where two adjacent substituents form a ring and two A situation where adjacent substituents do not form a ring.
  • any two adjacent substituents in Ar 2 form a substituted or unsubstituted 3-15 membered ring
  • any two adjacent substituents in Ar 2 can be connected to each other to form A 3- to 15-membered ring, or any two adjacent substituents in Ar 2 may also exist independently.
  • Any two adjacent substituents may include two substituents on the same atom, and may also include one substituent on two adjacent atoms; wherein, when there are two substituents on the same atom When , two substituents can form a saturated or unsaturated ring with the atom connected together; when two adjacent atoms respectively have a substituent, the two substituents can be fused to form a ring.
  • any two adjacent substituents in Ar 2 form a substituted or unsubstituted 3-15 membered ring includes any two adjacent substituents connected to each other to form a substituted or unsubstituted ring with their common connected atoms. 3-15 membered rings.
  • the fluorenyl group may be substituted by 1, 2, 3 or 4 substituents, wherein any two adjacent substituents may combine with each other to form a substituted or unsubstituted spiro ring structure.
  • Substituted fluorenyl groups can be: etc., but not limited to this.
  • 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 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings The number q of "substituents may be the same or different, each R" may 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 convenience of description, the substituent is collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent ie Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, trialkylsilyl group, alkyl group, haloalkyl group, cycloalkyl group and the like.
  • the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocycle.
  • the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a fluorenyl, anthracenyl) and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Base etc.
  • the arylene group referred to refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
  • the substituted aryl group can be that one or more than two hydrogen atoms in the aryl group are replaced by such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a ring Alkyl, haloalkyl and other groups are substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuryl-substituted phenyl groups, dibenzothienyl-substituted phenyl groups, pyridyl-substituted phenyl groups, and the like.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with 18 carbon atoms refers to the aryl group and the substituted The total number of carbon atoms in the group is 18.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se and S.
  • the 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 a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic
  • the ring system is an aromatic single ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phen
  • thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings linked by carbon-carbon bonds.
  • System type heteroaryl In the present application, the heteroarylene referred to refers to the divalent group formed by the further loss of a hydrogen atom from the heteroaryl group.
  • the substituted heteroaryl group can be one or more than two hydrogen atoms in the heteroaryl group replaced by such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, etc. , cycloalkyl, haloalkyl and other groups are substituted.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. 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.
  • the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,
  • Specific examples of aryl as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.
  • the substituent in the "substituted or unsubstituted aryl group having 6 to 20 carbon atoms", the substituent is selected from deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms
  • the substituent may be selected from deuterium, fluorine, cyano, and alkyl having 1 to 5 carbon atoms.
  • aryl include, but are not limited to, phenyl, biphenyl, naphthyl, and fluorenyl.
  • the number of carbon atoms of the aryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, specific examples of heteroaryl as substituents include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl Linyl, quinazolinyl, quinoxalinyl, isoquinolinyl.
  • the alkyl group having 1 to 10 carbon atoms may include straight chain alkyl groups having 1 to 10 carbon atoms and branched chain alkyl groups having 3 to 10 carbon atoms.
  • the number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
  • alkyl group examples include, but are not limited to, methyl, ethyl, n-propyl, iso Propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-Dimethyloctyl, etc.
  • the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
  • trialkylsilyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, and the like.
  • haloalkyl examples include, but are not limited to, trifluoromethyl.
  • the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be 3, 4, 5, 6, 7, 8, or 10, for example.
  • Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
  • a non-positioning linkage refers to a single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond runs through, 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 unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1) to any possible connection shown in formula (f-10):
  • the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned link extending from the middle of a benzene ring on one side,
  • the meaning it represents includes any possible connection mode shown in formula (X'-1) ⁇ formula (X'-4):
  • the organic compound has a structure shown in any one of formula 1-1 to formula 1-12:
  • both Ar 1 and Ar 2 are not phenanthrene.
  • phenanthrenyl is not included in the compounds of the present application.
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 9 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 9 to 25 carbon atoms.
  • Ar can be selected from substituted or unsubstituted carbon atoms of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 , 20, 21, 22, 23, 24, 25 aryl, substituted or unsubstituted heteroaryl with 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms .
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 10 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 25 carbon atoms.
  • the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cycloalkyl with 5 to 10 carbon atoms, and 1 carbon atom
  • Ar is selected from substituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene.
  • the substituents in Ar are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl.
  • Ar is selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of:
  • the substituted group V has one or more substituents independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl , ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl, and when the number of substituents is greater than 1, each substituent is the same or different.
  • Ar is selected from the group consisting of :
  • Ar is selected from the group consisting of the following groups:
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 6 to 33 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 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, 26, 27, 28, 29, 30, 31, 32, 33 substituted or unsubstituted aryl, substituted or unsubstituted hetero with 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms Aryl.
  • Ar 2 is selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.
  • the substituents in Ar are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cycloalkyl with 5 to 10 carbon atoms, and 1 carbon atom
  • the substituent on the ring is selected from an alkyl group with 1 to 5 carbon atoms.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carb Azolyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted triphenylene.
  • the substituents in Ar are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, Tert-butyl, phenyl, naphthyl or biphenyl;
  • any two adjacent substituents in Ar 2 form a substituted or unsubstituted fluorene ring, and the substituents on the fluorene ring are selected from methyl radical, ethyl, isopropyl or tert-butyl.
  • Ar is selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
  • the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl , ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl, and when the number of substituents is greater than 1, each substituent is the same or different.
  • Ar is selected from the group consisting of the following groups:
  • Ar is selected from the following groups :
  • L, L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 20 carbon atoms, a substituted or unsubstituted arylene group with 5 to 20 carbon atoms Substituted heteroarylene.
  • the substituents in L, L and L are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, carbon A trialkylsilyl group with 3 to 7 atoms, a fluoroalkyl group with 1 to 5 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, an aryl group with 6 to 15 carbon atoms or a carbon A heteroaryl group having 5 to 12 atoms.
  • L, L and L are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted Substituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted quinolinylene , a substituted or unsubstituted carbazolyl group.
  • the substituents in L, L and L are each independently selected from deuterium , fluorine, cyano, methyl, ethyl, isopropyl, tert - butyl, phenyl, naphthyl, biphenyl , pyridyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, dibenzofuryl, dibenzothienyl or carbazolyl.
  • L is selected from a single bond, a substituted or unsubstituted arylene group with 6-21 carbon atoms, and a substituted or unsubstituted heteroarylene group with 5-12 carbon atoms.
  • L is selected from single bonds, substituted or unsubstituted subunits with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 carbon atoms Aryl, a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
  • the substituents in L are each independently selected from deuterium, fluorine, cyano, and an alkyl group with 1 to 5 carbon atoms, optionally replaced by deuterium, fluorine, cyano, or an alkyl group with 1 to 5 carbon atoms.
  • L is selected from a single bond, a substituted or unsubstituted arylene group with 6-18 carbon atoms, and a substituted or unsubstituted heteroarylene group with 5-15 carbon atoms.
  • L is selected from single bonds, substituted or unsubstituted arylene groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms, and the number of carbon atoms is 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 substituted or unsubstituted heteroarylene.
  • the substituents in L are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, and aryl with 6 to 12 carbon atoms.
  • L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, Substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofurylene.
  • the substituents in L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl or phenyl.
  • L is selected from a single bond, or a substituted or unsubstituted group Q, wherein the unsubstituted group Q is selected from the group consisting of:
  • the substituted group Q has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, and when substituted When the number of groups is greater than 1, each substituent is the same or different.
  • L is selected from single bond, substituted or unsubstituted phenylene.
  • the substituents in L are each independently selected from 9,9-dimethylfluorenyl, dibenzofuryl, dibenzothienyl, biphenyl, benzene substituted by deuterium, fluorine, or cyano base.
  • L is selected from a single bond or the group consisting of:
  • L is selected from a single bond or the group consisting of the following groups:
  • L 1 and L 2 are each independently selected from single bonds, substituted or unsubstituted arylene groups with 6-12 carbon atoms.
  • L1 and L2 are each independently selected from single bonds, substituted or unsubstituted arylene groups having 6 , 7, 8, 9, 10, 11 , or 12 carbon atoms.
  • the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms or phenyl.
  • L and L are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene.
  • the substituents in L and L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert - butyl or phenyl.
  • L and L are each independently selected from a single bond or the group consisting of the following groups:
  • the total number of carbon atoms of Ar 1 and Ar 2 is 18-50, preferably 18-40.
  • the structure of the organic compound is shown in formula I:
  • L 2 is a single bond
  • X is selected from O, S, C(Me) 2 , and C(Ph) 2
  • Ar 2 is as defined above.
  • Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, the molecular spatial configuration of such organic compounds More three-dimensional, thereby increasing the T 1 level, effectively blocking the diffusion of excitons, increasing the molecular rigidity and thermal stability as a whole, and improving the service life of the device.
  • the organic compound is selected from the group consisting of the following compounds:
  • the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer includes the organic compound of the present application.
  • the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.
  • the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer , wherein the second hole transport layer comprises the organic compound of the present application.
  • an organic electroluminescent device includes an anode 100 , a first hole transport layer 321 , a second hole transport layer 322 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 stacked in sequence.
  • the anode 100 includes an anode material, which is preferably a material with a large work function (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 their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It preferably includes a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the first hole transport layer 321 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. There is no particular limitation on this.
  • the first hole transport layer 321 is composed of compound NPB.
  • the second hole transport layer 322 contains the compound of the present application.
  • the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a dopant material.
  • the organic light-emitting layer 330 is composed of a host material and a dopant material.
  • the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy To the host material, the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.
  • the host material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not particularly limited in this application.
  • the host material of the organic light emitting layer 330 is CDBP.
  • the dopant material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials, and this application does not make a special statement about it. limits.
  • the dopant material of the organic light emitting layer 330 is Ir(piq) 2 (acac).
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials.
  • the electron transport material can be selected from, but not limited to, ET-1, TPBi, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials.
  • the materials of the electron transport layer 340 are ET-1 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 is also provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 is composed of F4-TCNQ.
  • an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds.
  • the electron injection layer 350 includes Yb.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 ; the functional layer 300 contains the organic compound of the present application.
  • the photoelectric conversion device includes an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 which are sequentially stacked.
  • the hole transport layer 320 includes the organic compound of the present application.
  • the photoelectric conversion device is a solar cell, preferably an organic thin film solar cell.
  • a solar cell includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer and a cathode which are sequentially stacked, wherein the hole transport layer contains the organic compound of the present application.
  • the present application provides an electronic device, including the electronic component provided in the second aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the first electronic device 400 may be, for example, 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 lights, optical modules, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the photoelectric conversion device described above.
  • the second electronic device 500 may be a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all raw material products obtained through commercial channels.
  • 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (20 g, 74.8 mmol), 4-chlorophenylboronic acid (14.0 g, 89.8mmol), tetrakis(triphenylphosphine)palladium (0.43g, 0.37mmol), potassium carbonate (25.8g, 187mmol), 160mL of toluene, 80mL of ethanol and 40mL of water; under nitrogen protection, heated to reflux overnight .
  • Synthesize IMA-X listed in Table 1 with reference to the method of IMA-1, the difference is that starting material 1 is used instead of 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetra Hydronaphthalene, using raw material 2 instead of 4-chlorophenylboronic acid, wherein, the main raw material used, the synthesized IMA-X and its yield are shown in Table 1.
  • IM B-Y listed in Table 2 was synthesized according to the method of IM B-1, the difference was that starting material 3 was used instead of 4-bromo-1,1'-biphenyl, and starting material 4 was used instead of 4-amino-1,1'- Biphenyl, wherein the main raw material used, the synthetic IMB-Y and its yield are shown in Table 2.
  • Embodiment 1 Preparation of red organic electroluminescent device
  • Organic electroluminescent devices were prepared by the following process: A thick ITO substrate (manufactured by Corning) was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (height), and it was prepared into an experimental substrate with an anode and an insulating layer pattern using a photolithography process. And O 2 : N 2 plasma for surface treatment to increase the work function of the anode, and use organic solvents to clean the surface of the ITO substrate to remove impurities and oil on the surface of the ITO substrate.
  • CDBP and Ir(piq) 2 (acac) were evaporated with a weight ratio of 98%:2% to form a thickness of organic light-emitting layer.
  • the compound ET-1 and LiQ were vapor-deposited at a weight ratio of 1:1 to form a thickness of electron transport layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that the other compounds listed in Table 6 were used instead of Compound 1 when forming the second hole transport layer.
  • An organic electroluminescent device was produced in the same manner as in Example 1, except that Compound A, Compound B, Compound C, Compound D, and Compound E were used instead of Compound 4 when forming the second hole transport layer.
  • the driving voltage of the organic compound used in Examples 1-44 is at least 7% lower than that of the device formed by the organic compound used in Comparative Examples 1-4.
  • the luminous efficiency is increased by at least 15.7%
  • the external quantum efficiency is increased by at least 14.3%
  • the lifetime is increased by at least 25%.
  • the luminous efficiency is increased by at least 1.2%
  • the external quantum efficiency is increased by at least 9.9%
  • the lifetime is increased by at least 11.4%.
  • Ar 1 and Ar 2 are selected from the organic compound of the application of substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl and dibenzo five-membered ring structure can guarantee that device has higher hole Mobility, and can effectively block electrons and excitons from entering the hole transport layer, thereby improving the efficiency of the device.
  • the molecular stability is high, which can further improve the luminous efficiency and service life of the device.

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Abstract

本申请涉及一种有机化合物及包含其的电子元件和电子装置。本申请的有机化合物结构式如式1表示，将该有机化合物应用于有机电致发光器件中，可显著改善器件的性能。

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6月18日递交的申请号为202110680141.2以及于2021年8月25日递交的申请号为202110983941.1的中国专利申请的优先权，其全部内容通过引用并入本申请。
技术领域
本申请属于有机材料技术领域，尤其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
有机电致发光器件技术由于具有主动发光、发光效率较高、功耗低、轻、薄、响应速度快、可视角度大等优点被视为下一代显示和照明技术。有机电致发光器件由基板、阳极、空穴注入层、空穴传输层及电子阻挡层、发光层、电子传输层及空穴阻挡层、电子注入层以及阴极等组成。电子和空穴分别从阴极和阳极注入，然后通过电子传输层和空穴传输层在发光层复合形成激子，激子回到基态而发光。为了使有机发光器件表现出低驱动电压、高效率和长寿命的特性，在器件中形成有机层的材料，如空穴注入层材料、空穴传输层材料及电子阻挡层材料、发光层材料、电子传输层材料及空穴阻挡层材料、电子注入层材料材料等，由稳定且高效的材料支撑。
通常，在高温环境下驱动或保管有机电致发光元件时，有机电致发光元件会产生光颜色的变化、发光效率的降低、驱动电压的升高、发光寿命的缩短等不良影响。为了防止该影响，必须升高空穴传输层材料的玻璃化转变温度。目前报道的空穴传输层材料由于分子量普遍较小，材料的玻璃化温度较低；在材料使用过程中，反复充电放电会使材料容易结晶、薄膜的均一性被破坏，从而影响材料使用寿命。
因此，开发稳定、高效的空穴传输层材料，以改善电荷迁移率、降低驱动电压、提高器件发光效率、延长器件寿命具有非常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，该有机化合物用于有机电致发光器件中，可以改善元件的性能。
本申请的第一方面提供一种有机化合物，其具有如式1表示的结构：
Figure PCTCN2022084478-appb-000001
其中，R 1和R 2相同或不同，且各自独立地选自氢、氘或甲基；
n选自1或2；
Ar 1选自碳原子数为9～40的取代或未取代的芳基、碳原子数为9～30的取代或未取代的杂芳基；
Ar 2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、碳原子数为3～30的取代或未取代的亚杂芳基；
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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷基、碳原子数为3～20的杂芳基、碳原子数为6～20的取代或未取代的芳基，该芳基中的取代基选自氘、卤素基团、氰基、碳原子数为1～10的烷基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
可选地，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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为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；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
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，以及设于所述阳极和所述阴极之间的功能层；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。
本申请的有机化合物中，特定的苯并五元/六元环结合到三芳胺中，且控制三芳胺其中一个取代基具有较大的分子结构，一方面，使得分子的空间构型更立体，从而提高T 1水平，可以有效阻挡激子的扩散，提高器件(OLED)的寿命；另一方面，这样的特定结构具有更好的空穴的迁移率，提高了空穴传输层与有机层之间的匹配性，能有效提高器件(OLED)的效率。
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第一电子装置的示意图。
图3是本申请一种实施方式的光电转换器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的示意图。
附图标记
100、阳极            200、阴极             300、功能层           310、空穴注入层
320、空穴传输层      321、第一空穴传输层   322、第二空穴传输层   330、有机发光层
340、电子传输层      350、电子注入层       360、光电转化层       400、第一电子装置
500、第二电子装置
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。
第一方面，本申请提供一种有机化合物，其具有如式1表示的结构：
Figure PCTCN2022084478-appb-000002
其中，R 1和R 2相同或不同，且各自独立地选自氢、氘或甲基；
n选自1或2；
Ar 1选自碳原子数为9～40的取代或未取代的芳基、碳原子数为9～30的取代或未取代的杂芳基；
Ar 2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、碳原子数为3～30的取代或未取代的亚杂芳基；
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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷基、碳原子数为3～20的杂芳基、碳原子数为6～20的取代或未取代的芳基，该芳基中的取代基选自氘、卤素基团、氰基、碳原子数为1～10的烷基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
可选地，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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为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；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
本申请中，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，任意两个相邻取代基××形成环”意味着这两个取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。再比如，“任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环”是指Ar 2中的任意两个相邻的取代基可以相互连接形成3～15元环，或者Ar 2中的任意两个相邻的取代基也可以各自独立的存在。“任意两个相邻的取代基”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环。例如“Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环”包括任意两个相邻的取代基相互连接以与它们共同连接的原子形成取代或未取代的3～15元环。
本申请中，芴基可以被1个、2个、3个或4个取代基取代，其中，任意相邻的2个取代基可以彼此结合而形成取代或未取代的螺环结构。取代的芴基可以为：
Figure PCTCN2022084478-appb-000003
Figure PCTCN2022084478-appb-000004
等，但并不限定于此。
本申请中，
Figure PCTCN2022084478-appb-000005
是指与其他取代基或结合位置结合的化学键。
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“……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 PCTCN2022084478-appb-000006
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)。举例来讲，“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、杂芳基、芳基、三烷基硅基、烷基、卤代烷基、环烷基等。
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为碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言，在本申请中，联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、联苯基、三联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2022084478-appb-000007
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、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩基取代的苯基、吡啶基取代的苯基等。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，指的是芳基和取代基的总碳原子数为18。
本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。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、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。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碳原子数可以为6～20，例如碳原子数可以为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20，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、
Figure PCTCN2022084478-appb-000008
基。
本申请中，作为取代基，“碳原子数为6～20的取代或未取代的芳基”中，取代基选自氘、卤素基团、氰基、碳原子数为1～10的烷基，例如，取代基可以选自氘、氟、氰基、碳原子数为1～5的烷基，芳基的具体实例包括但不限于，苯基、联苯基、萘基、芴基。
本申请中，作为取代基的芳基的碳原子数可以为3～20，例如碳原子数可以为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20，作为取代基的杂芳基的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、异喹啉基。
本申请中，碳原子数为1～10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5、6、7、8、9、10，烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
本申请中，卤素基团例如可以为氟、氯、溴、碘。
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。
本申请中，碳原子数为3～10的环烷基的碳原子数例如可以为3、4、5、6、7、8、10。环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2022084478-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 PCTCN2022084478-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 PCTCN2022084478-appb-000011
在本申请的一些实施方式中，所述有机化合物具有式1-1至式1-12中任一项所示的结构：
Figure PCTCN2022084478-appb-000012
本申请中，Ar 1和Ar 2均不为菲基。可选地，本申请的化合物中不包括菲基。
可选地，Ar 1选自碳原子数为9～25的取代或未取代的芳基、碳原子数为9～25的取代或未取代的杂芳基。具体地，Ar 1可以选自碳原子数为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，碳原子数为9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25的取代或未取代的杂芳基。
可选地，Ar 1选自碳原子数为10～25的取代或未取代的芳基、碳原子数为12～25的取代或未取代的杂芳基。
可选地，Ar 1中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、碳原子数为5～10的环烷基、碳原子数为1～5的烷基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
可选地，Ar 1选自取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、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、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的三亚苯基。
可选地，Ar 1中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基。
可选地，Ar 1选自取代或未取代的基团V，其中，未取代的基团V选自如下基团组成的组：
Figure PCTCN2022084478-appb-000013
取代的基团V中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基，且取代基个数大于1时，各取代基相同或不同。
可选地，Ar 1选自以下基团所组成组：
Figure PCTCN2022084478-appb-000014
在一种具体的实施方式中，Ar 1选自以下基团所组成组：
Figure PCTCN2022084478-appb-000015
可选地，Ar 2选自碳原子数为6～33的取代或未取代的芳基、碳原子数为12～20的取代或未取代的杂芳基。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、26、27、28、29、30、31、32、33的取代或未取代的芳基，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。
可选地，Ar 2选自碳原子数为6～25的取代或未取代的芳基、碳原子数为12～20的取代或未取代的杂芳基。
可选地，Ar 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、碳原子数为5～10的环烷基、碳原子数为1～5的烷基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的5～13元环，该环上的取代基选自碳原子数为1～5的烷基。
在一种实施方式中，Ar 2选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、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、取代或未取代的三亚苯基。
可选地，Ar 2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的芴环，所述芴环上的取代基选自甲基、乙基、异丙基或叔丁基。
在一种实施方式中，Ar 2选自取代或未取代的基团W，其中，未取代的基团W选自如下基团组成的组：
Figure PCTCN2022084478-appb-000016
取代的基团W中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基，且当取代基个数大于1时，各取代基相同或不同。
在一种具体的实施方式中，Ar 2选自以下基团所组成的组：
Figure PCTCN2022084478-appb-000017
可选地，Ar 2选自以下基团：
Figure PCTCN2022084478-appb-000018
Figure PCTCN2022084478-appb-000019
在一种实施方式中，L、L 1和L 2各自独立地选自单键、碳原子数为6～20的取代或未取代的亚芳基、碳原子数为5～20的取代或未取代的亚杂芳基。
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、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3～7的三烷基硅基、碳原子数为1～5的氟代烷基、碳原子数为5～10的环烷基、碳原子数为6～15的芳基或碳原子数为5～12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、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代基的亚二苯并噻吩基、取代或未取代基的亚二苯并呋喃基、取代或未取代的亚喹啉基、取代或未取代的亚咔唑基。
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、苯基、萘基、联苯基、吡啶基、三甲基硅基、三氟甲基、环戊基、环己基、二苯并呋喃基、二苯并噻吩基或咔唑基。
在一种实施方式中，L选自单键、碳原子数为6～21的取代或未取代的亚芳基、碳原子数为5～12的取代或未取代的亚杂芳基。例如，L选自单键，碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21的取代或未取代的亚芳基，碳原子数为5、6、7、8、9、10、11、12的取代或未取代的亚杂芳基。
可选地，L中的取代基各自独立地选自氘，氟，氰基，碳原子数为1～5的烷基，任选地被氘、氟、氰基、碳原子数为1～5的烷基取代或未取代的碳原子数为6～15的芳基，碳原子数为5～12的杂芳基；所述芳基中的取代基选自氘、氟、氰基、碳原子数为1～5的烷基。
在另一种实施方式中，L选自单键、碳原子数为6～18的取代或未取代的亚芳基、碳原子数为5～15的取代或未取代的亚杂芳基。例如，L选自单键，碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18的取代或未取代的亚芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15的取代或未取代的亚杂芳基。
可选地，L中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基。
在一种实施方式中，L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、取代或未取代的亚芴基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基。
可选地，L中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
可选地，L选自单键、或者取代或未取代的基团Q，其中，未取代的基团Q选自如下基团组成的组：
Figure PCTCN2022084478-appb-000020
取代的基团Q中具有一个或两个以上取代基，所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基，且当取代基个数大于1时，各取代基相同或不同。
在一种具体的实施方式中，L选自单键、取代或未取代的亚苯基。
可选地，L中的取代基各自独立地选自9,9-二甲基芴基，二苯并呋喃基，二苯并噻吩基，联苯基，被氘、氟、氰基取代的苯基。
在一种实施方式中，L选自单键或者如下基团组成的组：
Figure PCTCN2022084478-appb-000021
在一种具体的实施方式中，L选自单键或者如下基团组成的组：
Figure PCTCN2022084478-appb-000022
在一种实施方式中，L 1和L 2各自独立地选自单键、碳原子数为6～12的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的取代或未取代的亚芳基。
可选地，L 1和L 2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～5的烷基或苯基。
在一种实施方式中，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。
可选地，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、叔丁基或苯基。
在一种具体的实施方式中，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 PCTCN2022084478-appb-000023
在一种实施方式中，式1中，Ar 1和Ar 2的总碳原子数为18～50，优选为18～40。
按照一种实施方式，所述有机化合物的结构如式I所示：
Figure PCTCN2022084478-appb-000024
其中，L 2为单键，X选自O、S、C(Me) 2、C(Ph) 2，Ar 2如上文定义。优选地，Ar 2选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基，取代或未取代的三联苯基，这样的有机化合物的分子空间构型更立体，从而提高T 1水平，有效地阻挡激子的扩散，整体上增加了分子刚性和热稳定性，提高器件的使用寿命。
可选地，所述有机化合物选自以下化合物所组成的组：
Figure PCTCN2022084478-appb-000025
Figure PCTCN2022084478-appb-000026
Figure PCTCN2022084478-appb-000027
Figure PCTCN2022084478-appb-000028
Figure PCTCN2022084478-appb-000029
Figure PCTCN2022084478-appb-000030
Figure PCTCN2022084478-appb-000031
Figure PCTCN2022084478-appb-000032
Figure PCTCN2022084478-appb-000033
第二方面，本申请提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请的有机化合物。
可选地，所述功能层包括空穴传输层，所述空穴传输层包含所述有机化合物。
进一步可选地，所述空穴传输层包括第一空穴传输层和第二空穴传输层，相对于所述第二空穴传输层，所述第一空穴传输层更靠近所述阳极，其中，所述第二空穴传输层包含本申请的有机化合物。
在一种实施方式中，电子元件为有机电致发光器件。如图1所示，有机电致发光器件包括依次层叠设置的阳极100、第一空穴传输层321、第二空穴传输层322、有机发光层330、电子传输层340和阴极200。
本申请中，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-(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，indiumtin oxide)(ITO)作为阳极的透明电极。
本申请中，第一空穴传输层321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。例如，第一空穴传输层321由化合物NPB组成。
可选地，第二空穴传输层322含有本申请的化合物。
本申请中，有机发光层330可以由单一发光层材料组成，也可以包括主体材料和掺杂材料。可选地，有机发光层330由主体材料和掺杂材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330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掺杂材料，进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、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。例如，有机发光层330的主体材料为CDBP。
有机发光层330的掺杂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。例如，有机发光层330的掺杂材料为Ir(piq) 2(acac)。
本申请中，电子传输层340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但不限于，ET-1、TPBi、LiQ、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。例如，电子传输层340的材料为ET-1和LiQ。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入材料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但不限于，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。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还设置有空穴注入层310，以增强向空穴传输层321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。例如，空穴注入层310由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350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。例如，电子注入层350包括Yb。
按照另一种实施方式，电子元件为光电转换器件。如图3所示，该光电转换器件包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请的有机化合物。
如图3所示，光电转换器件包括依次层叠设置的阳极100、空穴传输层320、光电转化层360、电子传输层340和阴极200。可选地，空穴传输层320包括本申请的有机化合物。
可选地，光电转换器件为太阳能电池，优选为有机薄膜太阳能电池。举例而言，太阳能电池包括依次层叠设置的阳极、空穴传输层、有机发光层、电子传输层和阴极，其中，空穴传输层包含有本申请的有机化合物。
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。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、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。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转换器件。例如，第二电子装置500可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
下面结合合成例来说明本申请的有机化合物的合成方法，但是本申请并不因此而受到任何限制。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
合成例
(1)IMA-1的合成：
Figure PCTCN2022084478-appb-000034
向500mL的三口烧瓶中投入6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘(20g，74.8mmol)、4-氯苯硼酸(14.0g，89.8mmol)、四(三苯基膦)钯(0.43g，0.37mmol)、碳酸钾(25.8g，187mmol)、160mL的甲苯、80mL的乙醇和40mL的水；在氮气保护下，加热至回流过夜。停止反应，冷却至室温，水洗三遍，最后用饱和氯化铵水溶液萃取一遍，合并有机相，用无水硫酸镁干燥后，旋蒸浓缩；将获得的固体用乙醇重结晶，得到IMA-1(17.6g，收率78.9％)。
参照IMA-1的方法合成表1所列的IMA-X，不同之处在于，使用原料1代替6-溴-1,1,4,4-四甲基-1,2,3,4-四氢化萘，使用原料2代替4-氯苯硼酸，其中，使用的主要原料、合成的IMA-X及其收率如表1所示。
表1
Figure PCTCN2022084478-appb-000035
Figure PCTCN2022084478-appb-000036
(2)IM B-1的合成：
Figure PCTCN2022084478-appb-000037
将4-溴-1,1’-联苯(17.6g，75.5mmol)、4-氨基-1,1’-联苯(12.8g，75.5mmol)和无水甲苯(PhMe)(140mL)投入250mL三口烧瓶中；在氮气保护下，升温至70℃，依次加入叔丁醇钠(10.9g，113.3mmol)、2-双环己基膦-2',4',6'-三异丙基联苯(X-Phos)(0.63g，1.51mmol)和三(二亚苄基丙酮)二钯(Pd 2(dba) 3)(0.70g，0.76mmol)，升温至回流反应1h；然后降至室温，水洗三次，用10g无水硫酸镁干燥，静置30min，抽滤，高压浓缩。过柱层析色谱柱纯化，得到IM B-1(21.4g，收率88.2％)。
参照IM B-1的方法合成表2所列的IM B-Y，不同之处在于，使用原料3代替4-溴-1,1’-联苯，使 用原料4代替4-氨基-1,1’-联苯，其中使用的主要原料、合成的IM B-Y及其收率如表2所示。
表2
Figure PCTCN2022084478-appb-000038
Figure PCTCN2022084478-appb-000039
Figure PCTCN2022084478-appb-000040
Figure PCTCN2022084478-appb-000041
(3)化合物4的合成：
Figure PCTCN2022084478-appb-000042
在氮气保护下，将IMA-1(5.31g，17.7mmol)、IM B-1(5.71g，17.7mmol)和甲苯(50mL)投入100mL的三口烧瓶中；升温至70℃，依次加入叔丁醇钠(2.56g，26.65mmol)、2-双环己基膦-2',6'-二甲氧基联苯(S-Phos)(0.15g，0.36mmol)、Pd 2(dba) 3(0.16g，0.18mmol)，升温回流反应2h；降至室温，水洗三次，无水硫酸镁干燥静置30min，抽滤，浓缩。过柱层析色谱柱，正庚烷重结晶得到化合物4(6g，收率57.9％)。质谱(m/z)＝584.32[M+H] +。
参照化合物4的方法合成表3所列的化合物Z，不同之处在于，使用原料5代替中间体IMA-1，使用原料6代替中间体IM B-1，其中，所使用的主要原料、合成的化合物及其收率、质谱如表3所示。
表3
Figure PCTCN2022084478-appb-000043
Figure PCTCN2022084478-appb-000044
Figure PCTCN2022084478-appb-000045
Figure PCTCN2022084478-appb-000046
Figure PCTCN2022084478-appb-000047
Figure PCTCN2022084478-appb-000048
Figure PCTCN2022084478-appb-000049
化合物核磁数据如下表4所示：
表4
Figure PCTCN2022084478-appb-000050
有机电致发光器件制备及评估：
实施例1：红色有机电致发光器件的制备
通过以下过程制备有机电致发光器件：将
Figure PCTCN2022084478-appb-000051
厚的ITO基板(康宁制造)切割成40mm(长)×40mm(宽)×0.7mm(高)的尺寸，采用光刻工序，将其制备成具有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基板表面的杂质及油污。
首先，在实验基板阳极上蒸镀F4-TCNQ形成厚度为
Figure PCTCN2022084478-appb-000052
的空穴注入层，再在空穴注入层上蒸镀NPB，形成厚度为
Figure PCTCN2022084478-appb-000053
的第一空穴传输层。然后，在第一空穴传输层上蒸镀化合物4，形成厚度为
Figure PCTCN2022084478-appb-000054
的第二空穴传输层。
在第二空穴传输层上，将CDBP和Ir(piq) 2(acac)以98％∶2％的重量比进行蒸镀形成厚度为
Figure PCTCN2022084478-appb-000055
的有机发光层。
在有机发光层上，将化合物ET-1和LiQ以1∶1的重量比进行蒸镀形成厚度为
Figure PCTCN2022084478-appb-000056
的电子传输层。
在电子传输层上蒸镀Yb以形成厚度为
Figure PCTCN2022084478-appb-000057
的电子注入层，然后在电子注入层上，将镁(Mg)和银(Ag)以1∶9的重量比进行蒸镀形成厚度为
Figure PCTCN2022084478-appb-000058
的阴极。
最后，在阴极上蒸镀化合物CP-1，形成厚度为
Figure PCTCN2022084478-appb-000059
的有机覆盖层，从而完成有机电致发光器件的制造。
实施例2～44
除了在形成第二空穴传输层时，以表6所列的其余化合物替代化合物1之外，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1～5
除了在形成第二空穴传输层时，分别使用化合物A、化合物B、化合物C、化合物D、化合物E替代化合物4之外，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下表5所示。
表5
Figure PCTCN2022084478-appb-000060
Figure PCTCN2022084478-appb-000061
对如上制得的有机电致发光器件，在15mA/cm 2的电流密度条件下分析器件性能，其结果如下表6所示。
表6
Figure PCTCN2022084478-appb-000062
Figure PCTCN2022084478-appb-000063
根据表6的结果可知，作第二空穴传输层时，实施例1～44所使用的有机化合物与比较例1～4中使用的有机化合物形成的器件相比，驱动电压至少降低了7％，发光效率至少提高了15.7％，外量子效率至少提高了14.3％，寿命最少提高了25％。
另外，实施例1～44所使用的有机化合物与比较例5使用的有机化合物形成的器件相比，发光效率至少提高了1.2％，外量子效率至少提高了9.9％，寿命至少提高了11.4％。可见，Ar 1和Ar 2选自取代或未取代的苯基、萘基、联苯基、三联苯基和二苯并五元环结构的本申请的有机化合物可以保证器件具有较高的空穴迁移率，并且能够有效的阻挡电子、激子进入到空穴传输层中，进而提高器件的效率，同时分子的稳定性高，能进一步提高器件的发光效率和使用寿命。
本领域的普通技术人员可以理解，上述各实施方式是实现本申请的具体实施例，而在实际应用中，可以在形式上和细节上对其作各种改变，而不偏离本申请的精神和范围。

Claims (17)

  1. 有机化合物，其特征在于，所述有机化合物具有如式1表示的结构：
    Figure PCTCN2022084478-appb-100001
    其中，R 1和R 2相同或不同，且各自独立地选自氢、氘或甲基；
    n选自1或2；
    Ar 1选自碳原子数为9～40的取代或未取代的芳基、碳原子数为9～30的取代或未取代的杂芳基；
    Ar 2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、碳原子数为3～30的取代或未取代的亚杂芳基；
    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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷基、碳原子数为3～20的杂芳基、碳原子数为6～20的取代或未取代的芳基，该芳基中的取代基选自氘、卤素基团、氰基、碳原子数为1～10的烷基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
  2. 根据权利要求1所述的有机化合物，其中，所述有机化合物具有如式1表示的结构：
    Figure PCTCN2022084478-appb-100002
    其中，R 1和R 2相同或不同，且各自独立地选自氢、氘或甲基；
    n选自1或2；
    Ar 1选自碳原子数为9～40的取代或未取代的芳基、碳原子数为9～30的取代或未取代的杂芳基；
    Ar 2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、碳原子数为3～30的取代或未取代的亚杂芳基；
    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3～12的三烷基硅基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为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；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的3～15元环，所述3～15元环的取代基选自碳原子数为1～10的烷基。
  3. 根据权利要求1或2所述的有机化合物，其中，所述有机化合物具有式1-1至式1-12中任一项所示的结构：
    Figure PCTCN2022084478-appb-100003
    Figure PCTCN2022084478-appb-100004
  4. 根据权利要求1或2所述的有机化合物，其中，Ar 1选自碳原子数为10～25的取代或未取代的芳基、碳原子数为12～25的取代或未取代的杂芳基；
    优选地，Ar 1中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、碳原子数为5～10的环烷基、碳原子数为1～5的烷基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基。
  5. 根据权利要求1或2所述的有机化合物，其中，Ar 1选自取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、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、取代或未取代的咔唑基、取代或未取代的芴基、取代或未取代的三亚苯基；
    优选地，Ar 1中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基。
  6. 根据权利要求1或2所述的有机化合物，其中，Ar 2选自碳原子数为6～33的取代或未取代的芳基、碳原子数为12～20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、三氟甲基、碳原子数为5～10的环烷基、碳原子数为1～5的烷基、碳原子数为6～12的芳基或碳原子数为5～12的杂芳基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的5～13元环，该环上的取代基选自碳原子数为1～5的烷基。
  7. 根据权利要求1或2所述的有机化合物，其中，Ar 2选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、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、取代或未取代的三亚苯基；
    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、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基或联苯基；任选地，Ar 2中的任意两个相邻的取代基形成取代或未取代的芴环，所述芴环上的取代基选自甲基、乙基、异丙基或叔丁基。
  8. 根据权利要求1或2所述的有机化合物，其中，Ar 2选自以下基团所组成的组：
    Figure PCTCN2022084478-appb-100005
    Figure PCTCN2022084478-appb-100006
  9. 根据权利要求1或2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6～20的取代或未取代的亚芳基、碳原子数为5～20的取代或未取代的亚杂芳基；
    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、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3～7的三烷基硅基、碳原子数为1～5的氟代烷基、碳原子数为5～10的环烷基、碳原子数为6～15的芳基或碳原子数为5～12的杂芳基。
  10. 根据权利要求1或2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、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代基的亚二苯并噻吩基、取代或未取代基的亚二苯并呋喃基、取代或未取代的亚喹啉基、取代或未取代的亚咔唑基；
    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、苯基、萘基、联苯基、吡啶基、三甲基硅基、三氟甲基、环戊基、环己基、二苯并呋喃基、二苯并噻吩基或咔唑基。
  11. 根据权利要求1或2所述的有机化合物，其中，L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、取代或未取代的亚芴基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基；
    优选地，L中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或苯基。
  12. 根据权利要求1所述的有机化合物，其中，L选自单键或者如下基团组成的组：
    Figure PCTCN2022084478-appb-100007
  13. 根据权利要求1或2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；
    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、叔丁基或苯基。
  14. 根据权利要求1或2所述的有机化合物，其中，所述有机化合物选自以下化合物所组成的组：
    Figure PCTCN2022084478-appb-100008
    Figure PCTCN2022084478-appb-100009
    Figure PCTCN2022084478-appb-100010
    Figure PCTCN2022084478-appb-100011
    Figure PCTCN2022084478-appb-100012
    Figure PCTCN2022084478-appb-100013
    Figure PCTCN2022084478-appb-100014
    Figure PCTCN2022084478-appb-100015
  15. 电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；其中，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。
  16. 根据权利要求15所述的电子元件，其中，所述功能层包括空穴传输层，所述空穴传输层包 含所述有机化合物；
    优选地，所述电子元件为有机电致发光器件或光电转换器件；
    更优选地，所述电子元件为有机电致发光器件，所述空穴传输层包括第一空穴传输层和第二空穴传输层，所述第一空穴传输层相对所述第二空穴传输层更靠近所述阳极，其中，所述第二空穴传输层包含所述的有机化合物。
  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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