WO2021223688A1 - 一种有机化合物和应用以及使用其的有机电致发光器件和电子装置 - Google Patents

一种有机化合物和应用以及使用其的有机电致发光器件和电子装置 Download PDF

Info

Publication number
WO2021223688A1
WO2021223688A1 PCT/CN2021/091703 CN2021091703W WO2021223688A1 WO 2021223688 A1 WO2021223688 A1 WO 2021223688A1 CN 2021091703 W CN2021091703 W CN 2021091703W WO 2021223688 A1 WO2021223688 A1 WO 2021223688A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
group
groups
ring
same
Prior art date
Application number
PCT/CN2021/091703
Other languages
English (en)
French (fr)
Inventor
聂齐齐
马天天
曹佳梅
Original Assignee
陕西莱特光电材料股份有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 陕西莱特光电材料股份有限公司 filed Critical 陕西莱特光电材料股份有限公司
Publication of WO2021223688A1 publication Critical patent/WO2021223688A1/zh

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—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
    • 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

  • This application belongs to the technical field of organic materials, and specifically provides an organic compound and application as well as electronic components and electronic devices using the same.
  • Such electronic components usually include 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 that are stacked in sequence.
  • the two electrodes When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the organic light-emitting layer, and the holes on the anode side also move to the light-emitting layer.
  • the electrons and holes combine in the organic light-emitting layer to form an excitation.
  • the exciton is in an excited state and releases energy to the outside, so that the organic light-emitting layer emits light to the outside.
  • organic light-emitting diodes have self-luminous characteristics, and the materials that dominate their luminescence are mainly electroluminescent materials.
  • current electroluminescent materials have low luminous efficiency and often lead to the failure of organic light-emitting diodes. Therefore, it is necessary An electroluminescent material and an electroluminescent device with high luminous efficiency are provided.
  • the purpose of this application is to provide an organic compound and electronic components and electronic devices using the same.
  • the organic compound can be used in organic electroluminescent devices to improve the use of organic electroluminescent devices. Longevity and luminous performance.
  • the first aspect of the present application provides an organic compound, which has a structure represented by the following formula (I):
  • a 1 , A 2 , A 3 and A 4 are the same or different from each other, and are each independently selected from a benzene ring, a condensed aromatic ring having 10 to 30 ring carbon atoms, and 10 to 30 ring carbon atoms. 30 fused heteroaromatic ring;
  • R 1 , R 2 , R 3 , R 4 and R 5 is the same or different from each other, and is independently selected from Hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms, substituted or unsubstituted carbon atom number 1-10 Alkyl group, substituted or unsubstituted cycloalkyl group having 3-10 carbon atoms, substituted or unsubstituted alkoxy group having 1-10 carbon atoms, substituted or unsubstituted carbon number 6-30 Arylamino group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R 1 , R 2 , R 3 , R 4 And at least one of R 5 is selected from Represents a chemical bond;
  • any two adjacent R 1 are connected to each other to form a ring, or any adjacent R 1 and R 2 are connected to each other to form a ring, or any adjacent R 2 and R 3 are connected to each other to form a ring, or any adjacent R 3 and R 4 are connected to each other to form a ring, or any adjacent R 4 and R 5 are connected to each other to form a ring, or any adjacent R 1 and R 5 are connected to each other to form a ring;
  • R 6 and R 7 is the same or different from each other, and is independently selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, and one having 18 to 24 carbon atoms. Triarylsilyl group, unsubstituted alkyl group having 1 to 10 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or Any two adjacent R 6 are connected to each other to form a ring, or any two adjacent R 7 are connected to each other to form a ring;
  • n 1 -n 7 are represented by n t
  • R 1 to R 7 are represented by R t
  • t is a variable, which represents any integer from 1 to 7
  • n t represents the number of substituents R t ; when t is 1 or 6 , N t is selected from 1, 2, 3; when t is 2, 3, 4 or 5, n t is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 ; When t is 7, n t is selected from 1, 2, 3, 4; when n t is greater than 1, any two R t are the same or different;
  • each of R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, and carbon atoms of 3-20 Heteroaryl groups, aryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, and those with 1 to 10 carbon atoms Alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, carbon atoms Heterocycloalkyl having 2 to 10, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms
  • the second aspect of the present application provides an electronic component, including an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer contains the organic compound described in the first aspect of the present application .
  • a third aspect of the present application provides an electronic device, and the electronic device includes the electronic component described in the second aspect of the present application.
  • the adamantane-fluorenyl group contained in the organic compound of the present application has a relatively large steric hindrance and a strong rigid structure, which can reduce the crystallinity of the molecule, improve the film-forming performance of the material, and thereby increase the life of the organic light-emitting device. And combining the adamantane-fluorene group with the solid ring centered on the boron element is conducive to improving the electronic stability, preventing the disappearance of excitons, and promoting the main energy transfer, which can significantly improve the stability of the carrier and improve the performance of the organic light-emitting device. Luminous performance.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural 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 structural diagram of a second electronic device according to an embodiment of the present application.
  • Anode; 200 cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light emitting layer 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • the first aspect of the present application provides an organic compound, which has a structure represented by the following formula (I):
  • a 1 , A 2 , A 3 and A 4 are the same or different from each other, and are each independently selected from a benzene ring, a condensed aromatic ring having 10 to 30 ring carbon atoms, and 10 to 30 ring carbon atoms.
  • 30 fused heteroaromatic ring in this application, the fused aromatic ring or the fused heteroaromatic ring is substituted or unsubstituted, and the substituent is selected from methyl and phenyl;
  • R 1 , R 2 , R 3 , R 4 and R 5 is the same or different from each other, and is independently selected from Hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms, substituted or unsubstituted carbon atom number 1-10 Alkyl group, substituted or unsubstituted cycloalkyl group having 3-10 carbon atoms, substituted or unsubstituted alkoxy group having 1-10 carbon atoms, substituted or unsubstituted carbon number 6-30 Arylamino group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R 1 , R 2 , R 3 , R 4 And at least one of R 5 is selected from Represents a chemical bond;
  • any two adjacent R 1 are connected to each other to form a ring, or any adjacent R 1 and R 2 are connected to each other to form a ring, or any adjacent R 2 and R 3 are connected to each other to form a ring, or any adjacent R 3 and R 4 are connected to each other to form a ring, or any adjacent R 4 and R 5 are connected to each other to form a ring, or any adjacent R 1 and R 5 are connected to each other to form a ring.
  • any Adjacent R 1 and R 2 both adjacent R 1 and R 2
  • any adjacent R 2 and R 3 adjacent R 2 and R 3
  • any adjacent R 3 and R 4 both adjacent R 4 and R 5
  • the number of carbon atoms of the formed ring may be 5-membered ring, for example, any adjacent R 1 and R 2 form Any adjacent R 2 and R 3 form Any adjacent R 3 and R 4 form Any adjacent R 4 and R 5 form It can also be a 6-membered ring, for example, any adjacent R 2 and R 3 form Any adjacent R 4 and R 5 form Any adjacent R 4 and R 5 form with any adjacent R 2 and R 3 It can also be a 13-membered ring, for example, adjacent R 4 and R 5 form adjacent R 2 and R 3
  • R 6 and R 7 is the same or different from each other, and is independently selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, and one having 18 to 24 carbon atoms.
  • Triarylsilyl group unsubstituted alkyl group with 1-10 carbon atoms, unsubstituted cycloalkyl group with 3-10 carbon atoms, unsubstituted alkoxy group with 1-10 carbon atoms, unsubstituted A substituted aryl group with 6 to 30 carbon atoms or an unsubstituted heteroaryl group with 2 to 30 carbon atoms, or any two adjacent R 6 connected to each other to form a ring, or any two adjacent Rs 7 are connected to each other to form a ring;
  • n 1 -n 7 are represented by n t
  • R 1 to R 7 are represented by R t
  • t is a variable, which represents any integer from 1 to 7
  • n t represents the number of substituents R t ; when t is 1 or 6 , N t is selected from 1, 2, 3; when t is 2, 3, 4 or 5, n t is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 ; When t is 7, n t is selected from 1, 2, 3, 4; when n t is greater than 1, any two R t are the same or different;
  • each of R 1 , R 2 , R 3 , R 4 , and R 5 are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, and carbon atoms of 3-20 Heteroaryl groups, aryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, and those with 1 to 10 carbon atoms Alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, carbon atoms Heterocycloalkyl having 2 to 10, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms
  • the adamantane-fluorenyl group contained in the organic compound of the present application has a relatively large steric hindrance and a strong rigid structure, which can reduce the crystallinity of the molecule, improve the film-forming performance of the material, and thereby increase the life of the organic light-emitting device. And combining the adamantane-fluorene group with the solid ring centered on the boron element is conducive to improving the electronic stability, preventing the disappearance of excitons, and promoting the main energy transfer, which can significantly improve the stability of the carrier and improve the performance of the organic light-emitting device. Luminous performance.
  • ring carbon number refers to the atoms of a compound (for example, monocyclic compound, fused ring compound, bridging compound, carbocyclic compound, heterocyclic compound) forming a cyclic structure by atom bonding, which constitutes the ring itself The number of carbon atoms in it.
  • a compound for example, monocyclic compound, fused ring compound, bridging compound, carbocyclic compound, heterocyclic compound
  • ring-forming carbon number mentioned below has the same meaning as long as it is not specifically noted.
  • the benzene ring has 6 carbon atoms
  • the naphthalene ring has 10 carbon atoms
  • the phenanthrene ring has 14 carbon atoms
  • the anthracene ring has 14 carbon atoms
  • the furan ring has 4 carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring carbon numbers.
  • the carbon number of the fluorene ring as the substituent is not included in the number of ring carbon atoms.
  • the number of ring-forming atoms means a compound (e.g., monocyclic compound, fused ring compound, bridging compound, carbocyclic compound, Heterocyclic compound) the number of atoms constituting the ring itself. Atoms that do not constitute a ring (for example, a hydrogen atom that terminates the bonding of atoms constituting the ring), and the atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms.
  • the "number of ring-forming atoms" mentioned below has the same meaning unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • the hydrogen atoms bonded to the ring-forming carbon atoms of the pyridine ring and the quinazoline ring, and the atoms constituting the substituent are not included in the number of ring-forming atoms.
  • a fluorene ring as a substituent is bonded to the fluorene ring (including a spirofluorene ring)
  • the number of atoms of the fluorene ring as a substituent is not included in the number of ring atoms.
  • adamantane is a three-dimensional structure, in the compound structure diagram, because of different drawing angles, it will show different planar shapes.
  • the ring structure formed on 9,9-dimethylfluorene is all adamantane.
  • the connection position is also the same. E.g: All have the same structure.
  • each... are independently” and “... are independently” and “... are independently selected from” are interchangeable, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that the specific options expressed between the same symbols do not affect each other in the same group.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is:
  • formula Q-1 represents 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 R on two benzene rings The number q of "substituents can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc).
  • the "substituted or unsubstituted aryl group” refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, and one having 3 to 12 carbon atoms.
  • Trialkylsilyl group triarylsilyl group having 18 to 24 carbon atoms, arylsilyl group having 8 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and 1 to carbon atoms 10 haloalkyl, carbon 2-6 alkenyl, carbon 2-6 alkynyl, carbon 3-10 cycloalkyl, carbon 2-10 heterocycloalkane Group, cycloalkenyl group having 5-10 carbon atoms, heterocycloalkenyl group having 4-10 carbon atoms, alkoxy group having 1-10 carbon atoms, alkylamino group having 1-10 carbon atoms , C1-C10 alkylthio group, C6-C18 aryloxy group, C6-C18 arylthio group, C6-C18 alkylsulfonyl group, A trialkylphosphino group having 3 to 18 carbon atoms, a trialkylboron group having 3 to 18 carbon atoms, optionally, any
  • the "substituted" functional group can be substituted by one or more than two substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc can exist independently Or they are connected to each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc may exist independently or be condensed with the functional group to which they are connected to form a ring.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if R 1 is selected from substituted aryl groups having 30 carbon atoms, all carbon atoms of the aryl group and the substituents thereon are 30.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more single Cyclic aryl groups, monocyclic aryl groups and fused ring aryl groups conjugated through carbon-carbon bonds, and two or more fused ring aryl groups conjugated through carbon-carbon bonds.
  • two or more aromatic groups conjugated through carbon-carbon bonds may also be regarded as aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (for example, a naphthyl group), a tricyclic fused aryl group (for example, a phenanthryl group, a fluorenyl group, an anthryl group), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • phenyl and the like are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene, Base and so on.
  • the involved arylene group refers to a divalent group formed by further losing one hydrogen atom of an aryl group.
  • aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, Anthryl, phenanthryl, base.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, and the like.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group.
  • the total number of carbon atoms of the group is 18.
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may 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.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofur
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
  • the involved heteroarylene group refers to a divalent group formed by the heteroaryl group further losing one hydrogen atom.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl group as a substituent includes, but is not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxaline base.
  • the alkyl group having 1 to 10 carbon atoms may be a straight-chain alkyl group or a branched-chain alkyl group.
  • the alkyl group having 1 to 10 carbon atoms may be a linear alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 3 to 10 carbon atoms.
  • the number of carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, for example.
  • alkyl groups having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isoamyl Base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the alkyl group having 1 to 5 carbon atoms may be a straight-chain alkyl group or a branched-chain alkyl group.
  • the alkyl group having 1 to 10 carbon atoms may be a linear alkyl group having 1 to 5 carbon atoms, or a branched alkyl group having 3 to 5 carbon atoms.
  • the number of carbon atoms of the alkyl group may be 1, 2, 3, 4, or 5, for example.
  • alkyl groups having 1 to 5 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isoamyl Base, neopentyl, cyclopentyl, etc.
  • an arylamino group is a group formed by replacing at least one hydrogen in an amine group (-NH 2) with an aromatic hydrocarbon.
  • an arylamino group in which two hydrogens in an amino group (-NH 2 ) are replaced by benzene is a diphenylamino group.
  • the arylamino group may be selected from anilino, diphenylamino, benzylamino, p-nitroanilin, m-nitroanilin, o-nitroanilin, N-methylanilin, acetanilin, Azophenyl, xylene diamino, N-p-toluene diamino and N-m-toluene diamino, etc.
  • the arylamino group may be selected from diphenylamino and dinaphthylamino.
  • the non-positioned connecting bond refers to the 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 penetrates, 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-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
  • the dibenzofuran group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of the benzene ring on one side, Its meaning includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • the non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and its meaning includes the following formula (Y-1) to Any possible connection mode shown in formula (Y-7).
  • the halogen group can be fluorine, chlorine, bromine, or iodine.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • triarylsilyl examples include, but are not limited to, triphenylsilyl and the like.
  • haloalkyl examples include, but are not limited to, trifluoromethyl.
  • a 1 , A 2 , A 3 and A 4 are the same or different from each other, and are each independently selected from a benzene ring and a condensed aromatic ring with 10 to 20 ring carbon atoms Or a condensed heteroaromatic ring with 10 to 20 ring carbon atoms.
  • a 1 , A 2 , A 3 and A 4 are the same or different from each other, and are each independently selected from a benzene ring, a fused aromatic ring with 10-15 ring carbon atoms Or a condensed heteroaromatic ring with 12 to 20 ring carbon atoms.
  • a 1 , A 2 , A 3 and A 4 are the same or different from each other, and are each independently selected from benzene, naphthalene, 9,9-dimethylfluorene, phenanthrene, and diphenyl Difuran, dibenzothiophene or N-phenylcarbazole.
  • the organic compound is selected from formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5) ), formula (I-6), formula (I-7), formula (I-8) or formula (I-9):
  • the organic compound is selected from the structure represented by the following formula (II):
  • each of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are the same or different from each other, and each is independently selected from O, S, Si (R 8 R 9 ), C (R 10 R 11 ), N( R 12 ), Se or not present, wherein R 8 , R 9 , R 10 , R 11 and R 12 are the same or different from each other, and are each independently selected from: an aryl group having 6 to 18 carbon atoms, and the number of carbon atoms Is a heteroaryl group having 3 to 18, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or R 8 and R 9 are connected to each other to form 5 with the atoms to which they are connected together -15-membered saturated or unsaturated ring, or R 10 and R 11 are connected to each other to form a 5-15-membered saturated or unsaturated ring with the atoms they are connected to together;
  • q 1 ⁇ q 5 are represented by q r
  • R 1 ⁇ R 5 are represented by R r
  • r is a variable, which represents any integer from 1 to 5, q r represents the number of substituents R r ; when r is 1, q r is selected from 1; when r is 2 or 5, q r is selected from 1, 2, 3; when r is 3 or 4, q r is selected from 1, 2; when q r is greater than 1, any two q r is the same or not the same.
  • the dotted line "------" connected by Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 in formula (II) indicates that the dotted line may or may not form a connection key.
  • the dashed line at Y 1 indicates that Y 1 can form a bond at this dashed line to connect with the benzene ring to form a ring, or it may not form a ring, that is, there is no Y 1 ;
  • the dashed line at Y 2 indicates that Y 2 can be in
  • the dotted line forms a bond to connect with the benzene ring to form a ring, or it may not form a ring, that is, there is no Y 2 ;
  • the dotted line at Y 3 indicates that Y 3 can form a bond at this dotted line to connect with the benzene ring to form a ring.
  • the dashed line at Y 4 indicates that Y 4 can form a bond at this dashed line to connect with the benzene ring to form a ring, or it may not form a ring, that is, there is no Y 4 ;
  • Y 5 The dotted line at here indicates that Y 5 can form a bond at this dotted line to connect with the benzene ring to form a ring, or it does not need to form a ring, that is, Y 5 does not exist.
  • At least one of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 may form a link at the dotted line to connect with the benzene ring to form a ring.
  • the organic compound has a structure represented by formula (III):
  • each of X 1 , X 2 , X 3 , X 4 and X 5 are the same or different from each other, and each is independently selected from a single bond or does not exist,
  • p 1 to p 5 are represented by p v
  • R 1 to R 5 are represented by R v
  • v is a variable, which represents any integer from 1 to 5
  • p v represents the number of substituents R v ; when v is 1, p v is selected from 1; when v is 2 or 5, p v is selected from 1, 2, 3; when v is 3 or 4, p v is selected from 1, 2; when p v is greater than 1, any two p v is the same or not the same.
  • each of R 1 , R 2 , R 3 , R 4 and R 5 is the same or different from each other, and is independently selected from Hydrogen, deuterium, cyano, halogen group, trialkylsilyl group with 3-12 carbon atoms, triarylsilyl group with 18-24 carbon atoms, substituted or unsubstituted carbon atom number 1-10 Or the group consisting of the following groups, and at least one of R 1 , R 2 , R 3 , R 4 and R 5 is selected from
  • M 1 is selected from a single bond or
  • G 1 to G 5 are each independently selected from N or C(F 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(F 1 ) , Any two F 1 are the same or different;
  • G 6 to G 13 are each independently selected from N or C(F 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(F 2 ) , Any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(F 3 ) , Any two F 3 are the same or different;
  • G 24 to G 33 are each independently selected from N or C(F 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(F 4 ) , Any two F 4 are the same or different;
  • E 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, triarylsilyl groups having 18 to 24 carbon atoms, and carbon atoms of 1 to 10 alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, Heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, Alkylamino group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, aryloxy group with 6 to 18 carbon atoms, arylthio group with 6 to 18 carbon atoms, carbon
  • Each E 2 to E 9 and E 23 are the same or different from each other, and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3 to 20 carbon atoms, and the number of carbon atoms is 3-12 trialkylsilyl groups, triarylsilyl groups with 18-24 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, 2 carbon atoms ⁇ 6 alkenyl, carbon 2-6 alkynyl, carbon 3-10 cycloalkyl, carbon 2-10 heterocycloalkyl, carbon 5-10 Cycloalkenyl, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylamino having 1 to 10 carbon atoms, and alkane having 1 to 10 carbon atoms Thio group, aryloxy group with 6 to 18 carbon atoms, arylthio group with 6 to 18 carbon atom
  • E 10 to E 22 and F 1 to F 4 are the same or different from each other, and are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano group, aryl group with 6 to 20 carbon atoms, carbon atom Heteroaryl groups with 3 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, alkyl groups with 1 to 10 carbon atoms, and carbon atoms Haloalkyl groups having 1 to 10, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and 2 to 10 carbon atoms Heterocycloalkyl, C5-10 cycloalkenyl, C4-10 heterocycloalkenyl, C1-10 alkoxy, C1-10 The alkylamino group, the alkylthio group with 1 to 10 carbon carbon
  • e 1 ⁇ e 23 are represented by e k
  • E 1 ⁇ E 23 are represented by E k
  • k is a variable, which represents any integer from 1 to 23
  • e k is the number of substituent E k ; wherein, when k is selected from 8 , 17, E k is selected from 1, 2 or 3; when k is selected when 3,4,5,13,15,18,19,23, e k is selected from 2, 3 or 4; when k is selected from self-1,2,6,7,9,16,21,22, e k is selected from 1,2,3,4 or 5; when k is selected from 14, e k is selected from 1,2,3,4 , 5 or 6; when k is selected from 10, 20, e k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is selected from 12, e k is selected from 1, 2, 3, 4 , 5, 6, 7 or 8; when k is selected from 11, e k is selected from 1, 2, 3, 4 , 5, 6, 7, 8 or 9; and
  • K 1 is selected from O, S, Se, N (E 24 ), C (E 25 E 26 ), Si (E 27 E 28 ); among them, each of E 24 , E 25 , E 26 , E 27 , and E 28 is each other The same or different, and each independently selected from: aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and 2 carbon atoms ⁇ 6 alkenyl, carbon 2-6 alkynyl, carbon 3-10 cycloalkyl, carbon 2-10 heterocycloalkyl, carbon 5-10 Cycloalkenyl, heterocycloalkenyl having 4 to 10 carbon atoms, or the above-mentioned E 25 and E 26 are connected to each other to form a 5- to 13-membered saturated or unsaturated ring with the atoms to which they are connected together, or the above-mentioned E 27 And E 28 are connected to each other to form a 5- to 13-member
  • K 2 is selected from a single bond, O, S, Se, N (E 29 ), C (E 30 E 31 ), Si (E 32 E 33 ); wherein, each of E 29 , E 30 , E 31 , E 32 , E 33 are the same or different from each other, and are each independently selected from: aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and carbon atoms Alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, heterocycloalkyl groups having 2 to 10 carbon atoms, and 5 carbon atoms ⁇ 10 cycloalkenyl, carbon 4-10 heterocycloalkenyl, or the above-mentioned E 30 and E 31 are connected to each other to form a 5- to 13-membered saturated or unsaturated ring together with the atoms to which
  • Atoms forming a 5- to 13-membered saturated or unsaturated ring means: E 30 and E 31 can be connected to each other to form a ring, or they can exist independently of each other; when E 30 and E 31 form a ring, the carbon of the ring
  • the number of atoms can be a 5-membered ring, for example It can also be a 6-membered ring, for example It can also be a 13-membered ring, for example
  • the number of carbon atoms forming the ring of E 30 and E 31 can also be other values, which will not be listed one by one here, and this application does not specifically limit the number of carbon atoms of this ring.
  • each of R 1 , R 2 , R 3 , R 4 and R 5 is the same or different, and is independently selected from Hydrogen, deuterium, cyano, fluorine, trimethylsilyl, triphenylsilyl, alkyl having 1 to 5 carbon atoms, substituted or unsubstituted group W, the unsubstituted group W selected From the group consisting of:
  • the substituent of the group W is selected from deuterium, fluorine, chlorine, cyano, trimethylsilyl, triphenylsilyl, methyl, ethyl, isopropyl, tert-butyl Group, phenyl, naphthyl, biphenyl, phenanthryl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, quinoxalinyl, quinazolinyl, 9,9-dimethylfluorenyl, two Benzofuranyl, dibenzothienyl, and carbazolyl; when there are multiple substituents in the group W, the multiple substituents are the same or different.
  • each of R 1 , R 2 , R 3 , R 4 and R 5 is the same or different, and is independently selected from Hydrogen, deuterium, cyano, fluorine, trimethylsilyl, triphenylsilyl, methyl, ethyl, isopropyl, tert-butyl, substituted or unsubstituted aryl groups with 6-15 carbon atoms , A substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 12 carbon atoms.
  • each of R 1 , R 2 , R 3 , R 4 and R 5 is the same or different, and is independently selected from Hydrogen, deuterium, cyano, fluorine, trimethylsilyl, triphenylsilyl, methyl, ethyl, isopropyl, tert-butyl or the following groups:
  • each of R 1 , R 2 , R 3 , R 4 and R 5 are the same or different from each other, and are each independently selected from: deuterium, fluorine, chlorine, Bromine, cyano, phenyl, naphthyl, biphenyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, pyridyl.
  • the organic compound is selected from the group consisting of the following compounds:
  • the application does not specifically limit the synthesis method of the organic compound provided, and those skilled in the art can determine a suitable synthesis method according to the organic compound of the application in combination with the preparation method provided in the synthesis example section.
  • the synthesis example part of the present invention exemplarily provides a method for preparing organic compounds, and the raw materials used can be obtained commercially or by methods well known in the art. Those skilled in the art can obtain all the organic compounds provided in this application according to these exemplary preparation methods. All specific preparation methods for preparing the organic compounds will not be described in detail here, and those skilled in the art should not be construed as limiting the application.
  • the second aspect of the present application provides an electronic component.
  • the electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer contains the first aspect of the present application Of organic compounds.
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.
  • the organic light-emitting layer can be composed of the organic compound provided in this application, or can be composed of the organic compound provided in this application and other materials together.
  • the organic light-emitting layer may be one layer or two or more layers.
  • the electronic component is an organic electroluminescence device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device, for example, a red light device or a blue light device.
  • the electronic component may be an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, and an electron transport layer 340 stacked in sequence. And cathode 200.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes 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 conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto.
  • a transparent electrode containing indium tin oxide (ITO) as an anode is preferable.
  • the first hole transport layer 321 and the second hole transport layer 322 respectively include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers and carbazole-linked triarylamines. Compounds or other types of compounds are not specifically limited in this application.
  • the first hole transport layer 321 may be composed of the compound NPB.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a dopant material.
  • the organic light-emitting layer 330 is composed of a host material and a doping 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, which transfer energy To the host material, the host material transfers energy to the doped material, which in turn enables the doped material to emit light.
  • the host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
  • the dopant material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative or other materials, and this application does not make special limits.
  • the dopant material of the organic light-emitting layer 330 contains the organic compound of the present application.
  • the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials.
  • the electron transport materials can be selected from, but not limited to, benzimidazole derivatives and oxadiazole derivatives. , Quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of TPBi and LiQ, or composed of DBimiBphen and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates the injection of electrons 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 their alloys; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferable to include a metal electrode containing magnesium and silver as a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first 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 may be composed of HAT-CN, or composed of m-MTDATA.
  • an electron injection layer 350 may be further 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 substances.
  • the electron injection layer 350 may include LiQ, or Mg and LiF.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include 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 includes the organic compound provided in the present application.
  • the photoelectric conversion device may include 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 and arranged.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the photoelectric conversion layer includes the organic Compound.
  • the functional layer 300 includes a photoelectric conversion layer 360, and the photoelectric conversion layer 360 includes an organic compound provided in the present application.
  • the photoelectric conversion layer 360 may be composed of the organic compound provided in the present application; in another embodiment, the photoelectric conversion layer 360 may be composed of the compound provided in the present application and other materials.
  • a third aspect of the present application provides an electronic device including the electronic component described 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 electroluminescent 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 lighting, light modules, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the aforementioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the compounds of the synthesis method not mentioned in this application are all raw material products obtained through commercial channels.
  • the organic compound of the present invention is synthesized by the following method:
  • the intermediate S in Table 1 was prepared by the same method as the synthesis of Intermediate B-1, except that the raw material G in the first column of Table 1 was used instead of the diphenylamine in Synthesis Example 1.
  • the magnesium bar (13.54 g, 564 mmol) and ether (100 mL) were placed in a round bottom flask dried under nitrogen protection, and iodine (100 mg) was added. Then, the ether (200mL) solution containing intermediate C-1 (64.00g, 187.0mmol) was slowly dropped into the flask. After the addition, the temperature was raised to 35°C and stirred for 3 hours; the reaction solution was reduced to 0°C, A solution of adamantanone (22.45g, 149mmol) in ether (200mL) was slowly dropped into it.
  • the magnesium bar (13.54 g, 564 mmol) and ether (100 mL) were placed in a round bottom flask dried under nitrogen protection, and iodine (100 mg) was added. Then, a solution of 2'-bromo-2-chlorobiphenyl (50.00g, 187.0mmol) in ether (200mL) was slowly dropped into the flask. After the addition, the temperature was raised to 35°C and stirred for 3 hours; the reaction solution was reduced At 0°C, slowly drop a solution of adamantanone (22.45g, 149mmol) in ether (200mL) into it.
  • the intermediate NA in Table 3 was prepared by the same method as in Synthesis Example 1, except that the material 1 in the first column of Table 3 was used instead of Intermediate A-4 in Synthesis Example 1, and the material 2 was used instead.
  • the aniline in Example 1 was synthesized to synthesize the intermediate NA in the third column of Table 3.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathode, anode, and insulating layer, using ultraviolet ozone and O 2 :N 2 plasma. Surface treatment to increase the work function of the anode (experimental substrate), and then to remove scum.
  • M-MTDATA (4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine) was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL).
  • HIL hole injection layer
  • NPB hole injection layer
  • HTL first hole transport layer
  • TCTA 4,4',4"-tris(carbazol-9-yl)triphenylamine
  • the host material (Host) of the ⁇ , ⁇ -ADN organic light-emitting layer, compound 10 is used as the dopant material (Dopant) of the organic light-emitting layer, and the host material and the dopant material are vapor-deposited at a film thickness ratio of 30:3 to form The thickness is Organic light emitting layer (EML).
  • EML Organic light emitting layer
  • Mg and LiF are vapor-deposited on the electron transport layer (ETL) in a weight ratio of 1:1 to form a thickness of The mixed film layer is used as the electron injection layer (EIL).
  • Magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1:9, and vacuum evaporated on the electron injection layer to form a thickness of The cathode.
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL), thereby completing the manufacture of organic electroluminescent devices.
  • the device performance is shown in Table 6.
  • the evaporation rate of organic materials is The evaporation rate of metal materials is The structural formulas of m-MTDATA, NPB, TCTA, ⁇ , ⁇ -ADN, DBimiBphen and LiQ are as follows:
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when preparing the organic light-emitting layer (EML), compound 10 (the dopant material for the light-emitting layer, Dopant) was replaced with those shown in Table 6. Of organic compounds.
  • EML organic light-emitting layer
  • the organic electroluminescence device was fabricated by the same method as in Example 1, except that when preparing the organic light-emitting layer (EML), the compound 10 (the dopant material for the light-emitting layer Dopant) was replaced with the compound BD-1.
  • EML organic light-emitting layer
  • the structure of BD-1 is shown in Table 5.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when preparing the organic light-emitting layer (EML), compound 10 (the dopant material for the light-emitting layer Dopant) was replaced with compound BD-2.
  • EML organic light-emitting layer
  • compound 10 the dopant material for the light-emitting layer Dopant
  • the structure of BD-2 is shown in Table 5.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when preparing the organic light-emitting layer (EML), compound 10 (the dopant material for the light-emitting layer Dopant) was replaced with compound BD-3.
  • EML organic light-emitting layer
  • compound 10 the dopant material for the light-emitting layer Dopant
  • the structure of BD-3 is shown in Table 5.
  • test methods and conditions include: testing at a constant current density of 10 mA/cm 2 and testing the lifetime of the T95 device at a constant current density of 20 mA/cm 2 , The test results are shown in Table 6.
  • the organic electroluminescent devices of Examples 1-24 have the characteristics of high luminous efficiency and long life. Specifically, compared with the comparative example, the luminous efficiency of the organic electroluminescent devices of Examples 1-24 is increased by at least 10.7%, and the lifetime is increased by at least 13.1%. This is because the organic compound of the present invention has an adamantane-fluorenyl structure, and the adamantane-fluorenyl group is connected to the end of the core instead of directly connected to the core, which can reduce the symmetry of the compound, thereby improving the material composition. Membranous.
  • the introduction of the group can increase the electron density of the entire conjugated system of the nitrogen-containing compound, and improve the hole conduction efficiency of the nitrogen-containing compound, thereby improving the carrier conduction efficiency and lifetime of the organic electroluminescent device and the photoelectric conversion device.
  • Combining a compound formed by adamantane-fluorene with a solid ring centered on boron can greatly increase the stability of carriers and improve the light-emitting performance of organic light-emitting devices.
  • the compound disclosed in this patent is used in an organic electroluminescent device, so that the organic electroluminescent device containing the compound has higher efficiency and better life.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本公开涉及一种有机化合物以及使用其的电子元件和电子装置，该有机化合物具有如下式(I)所示的结构，其中，A1、A2、A3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～30的稠合芳环、成环碳原子数为10～30的稠合杂芳环。本申请的有机化合物用作有机电致发光器件的有机发光层材料时，可以改善器件的发光性能和使用寿命。

Description

一种有机化合物和应用以及使用其的有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2020年5月8日递交的申请号为202010383434.X的中国专利申请以及2020年10月22日递交的申请号为202011140241.8的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请属于有机材料技术领域，具体地提供一种有机化合物和应用以及使用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元器件的应用范围越来越广泛。该类电子元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。
在现有技术中，有机发光二极管具有自发光特性，主导其发光的材料主要为电致发光材料，但是，当前的电致发光材料发光效率低，往往导致有机发光二极管的失效，因此，有必要提供一种发光效率高的电致发光材料和电致发光器件。
发明内容
针对现有技术存在的上述问题，本申请的目的是提供一种有机化合物以及使用其的电子元件和电子装置，该有机化合物可以用于有机电致发光器件中，提高有机电致发光器件的使用寿命和发光性能。
为了实现上述目的，本申请第一方面提供一种有机化合物，该有机化合物具有如下式(I)所示的结构：
Figure PCTCN2021091703-appb-000001
其中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～30的稠合芳环、成环碳原子数为10～30的稠合杂芳环；
各R 1、R 2、R 3、R 4和R 5彼此相同或不同，且分别独立地选自
Figure PCTCN2021091703-appb-000002
氢、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18～24的三芳基硅基、取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未取代的碳原子数为6～30的芳胺基、取代或未取代的碳原子数为6～30的芳基或者取代或未取代的碳原子数为2～30的杂芳基，且R 1、R 2、R 3、R 4和R 5中至少一者选自
Figure PCTCN2021091703-appb-000003
表示化学键；
或者任意两个相邻的R 1相互连接形成环，或者任意相邻的R 1与R 2相互连接形成环，或者任意相邻的R 2与R 3相互连接形成环，或者任意相邻的R 3与R 4相互连接形成环，或者任意相邻的R 4与R 5相互连接形成环，或者任意相邻的R 1与R 5相互连接形成环；
各R 6和R 7彼此相同或不同，且分别独立地选自氢、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18～24的三芳基硅基、未取代的碳原子数为1～10的烷基、未取代的碳原子数为6～30的芳基、或者未取代的碳原子数为2～30的杂芳基，或者任意两个相邻的R 6相互连接形成环，或者任意两个相邻的R 7相互连接形成环；
n 1-n 7以n t表示，R 1～R 7以R t表示，t为变量，表示1～7的任意整数，n t表示取代基R t的个数；当t为1或6时，n t选自1、2、3；当t为2、3、4或5时，n t选自1、2、3、4、5、6、7、8、9、10、11、12；当t为7时，n t选自1、2、3、4；当n t大于1时，任意两个R t相同或者不相同；
各R 1、R 2、R 3、R 4、R 5中的取代基彼此相同或不同，且各自独立地选自：氘、氟、氯、溴、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基。
本申请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；所述功能层含有本申请第一方面所述的有机化合物。
本申请第三方面提供一种电子装置，所述电子装置包括本申请第二方面所述的电子元件。
本申请的有机化合物含有的金刚烷-芴基具有较大的空间位阻和坚固的刚性结构，能够降低分子的结晶性，提高材料的成膜性能，进而提高有机发光器件的寿命。且将金刚烷-芴基与以硼元素为中心的实心环结合，有利于提高电子稳定性，防止激子消失，促进主体能量转移，可以显著提高载流子的稳定性，改善有机发光器件的发光性能。
本公开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公开的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一 起用于解释本公开，但并不构成对本公开的限制。在附图中：
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的结构示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的结构示意图。
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；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
以下结合附图对本公开的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本公开，并不用于限制本公开。
本申请第一方面提供一种有机化合物，该有机化合物具有如下式(I)所示的结构：
Figure PCTCN2021091703-appb-000004
其中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～30的稠合芳环、成环碳原子数为10～30的稠合杂芳环；在本申请中，所述稠合芳环或所述稠合杂芳环是取代或未取代的，所述取代基选自甲基、苯基；
各R 1、R 2、R 3、R 4和R 5彼此相同或不同，且分别独立地选自
Figure PCTCN2021091703-appb-000005
氢、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18～24的三芳基硅基、取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未取代的碳原子数为6～30的芳胺基、取代或未取代的碳原子数为6～30的芳基或者取代或未取代的碳原子数为2～30的杂芳基，且R 1、R 2、R 3、R 4和R 5中至少一者选自
Figure PCTCN2021091703-appb-000006
表示化学键；
或者任意两个相邻的R 1相互连接形成环，或者任意相邻的R 1与R 2相互连接形成环，或者任意相邻的R 2与R 3相互连接形成环，或者任意相邻的R 3与R 4相互连接形成环，或者任意相邻的R 4与R 5相互连接形成环，或者任意相邻的R 1与R 5相互连接形成环，需要说明的是，举例而言，当任意相邻的R 1与R 2(相邻的R 1与R 2两者)、任意相邻的R 2与R 3(相邻的R 2与R 3两者)、任意 相邻的R 3与R 4(相邻的R 3与R 4两者)、任意相邻的R 4与R 5(相邻的R 4与R 5两者)成环时，所形成的环的碳原子数可以是5元环，例如任意相邻的R 1和R 2形成
Figure PCTCN2021091703-appb-000007
任意相邻的R 2和R 3形成
Figure PCTCN2021091703-appb-000008
任意相邻的R 3和R 4形成
Figure PCTCN2021091703-appb-000009
任意相邻的R 4和R 5形成
Figure PCTCN2021091703-appb-000010
还可以是6元环，例如任意相邻的R 2和R 3形成
Figure PCTCN2021091703-appb-000011
Figure PCTCN2021091703-appb-000012
任意相邻的R 4和R 5形成
Figure PCTCN2021091703-appb-000013
Figure PCTCN2021091703-appb-000014
任意相邻的R 4和R 5与任意相邻相邻的R 2和R 3形成
Figure PCTCN2021091703-appb-000015
还可以是13元环，例如相邻的R 4和R 5与相邻的R 2和R 3形成
Figure PCTCN2021091703-appb-000016
可选地，相邻的两个R 1与R 2、相邻的两个R 2与R 3、相邻的两个R 3与R 4、相邻的两个R 4与R 5形成的环为饱和或不饱和的5至13元环，所述5至13元环是取代或未取代的，所述取代基选自甲基、乙基、异丙基、叔丁基、苯基，或者所述取代基任意两者形成芴环；
各R 6和R 7彼此相同或不同，且分别独立地选自氢、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18～24的三芳基硅基、未取代的碳原子数为1～10的烷基、未取代的碳原子数为3～10的环烷基、未取代的碳原子数为1～10的烷氧基、未取代的碳原子数为6～30的芳基或者未取代的碳原子数为2～30的杂芳基，或者任意两个相邻的R 6相互连接形成环，或者任意两个相邻的R 7相互连接形成环；
n 1-n 7以n t表示，R 1～R 7以R t表示，t为变量，表示1～7的任意整数，n t表示取代基R t的个数；当t为1或6时，n t选自1、2、3；当t为2、3、4或5时，n t选自1、2、3、4、5、6、7、8、9、10、11、12；当t为7时，n t选自1、2、3、4；当n t大于1时，任意两个R t相同或者不相同；
各R 1、R 2、R 3、R 4、R 5中的取代基彼此相同或不同，且各自独立地选自：氘、氟、氯、溴、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为 6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基。
在本申请中，“R 1、R 2、R 3、R 4和R 5中的1个、2个或者3个选自
Figure PCTCN2021091703-appb-000017
本申请的有机化合物含有的金刚烷-芴基具有较大的空间位阻和坚固的刚性结构，能够降低分子的结晶性，提高材料的成膜性能，进而提高有机发光器件的寿命。且将金刚烷-芴基与以硼元素为中心的实心环结合，有利于提高电子稳定性，防止激子消失，促进主体能量转移，可以显著提高载流子的稳定性，改善有机发光器件的发光性能。
本申请中，“成环碳数”表示，原子键合成环状的结构的化合物(例如，单环化合物、稠环化合物、桥接化合物、碳环化合物、杂环化合物)的构成该环自身的原子之中的碳原子的数量。在该环被取代基取代的情况下，取代基中含有的碳不包含在成环碳中。下文中所述的“成环碳数”只要没有特别注明就是相同含义。例如苯环的成环碳数为6，萘环的成环碳数为10，菲环的成环碳数为14，蒽环的成环碳数为14，呋喃环的成环碳数为4。另外，在苯环、萘环上作为取代基取代有例如烷基的情况下，该烷基的碳数不包含在成环碳数的数量中。另外，在芴环上作为取代基键合有例如芴环的情况下(包括螺芴环)，作为取代基的芴环的碳数不包括在成环碳数的数量中。
本申请中，“成环原子数”表示原子键合成环状的结构(例如，单环、稠环、集合环)的化合物(例如，单环化合物、稠环化合物、桥接化合物、碳环化合物、杂环化合物)的构成该环自身的原子的数量。不构成环的原子(例如，将构成环的原子的连接键封端的氢原子)、该环被取代基取代时的取代基中所含原子不包括在成环原子数中。下文中所述的“成环原子数”只要没有特别注明就是相同含义。例如，吡啶环的成环原子数为6，喹唑啉环的成环原子数为10，呋喃环的成环原子数为5。分别键合于吡啶环、喹唑啉环的成环碳原子上的氢原子、构成取代基的原子不包括在成环原子数的数量中。另外，在芴环上键合有作为取代基的例如芴环的情况下(包括螺芴环)，作为取代基的芴环的原子数不包括在成环原子数的数量中。
在本申请中，由于金刚烷是立体结构，在化合物结构图中，因为绘图角度不同，会呈现不同的平面形状，9,9-二甲基芴上所形成的环状结构均为金刚烷，并且连接位置也是相同的。例如：
Figure PCTCN2021091703-appb-000018
均为同一种结构。
在本申请中，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 PCTCN2021091703-appb-000019
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。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具 有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为8～12的芳基甲硅烷基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基，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5～18元的饱和或不饱和环。在本申请中，“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，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R 1选自取代的碳原子数为30的芳基，则芳基及其上的取代基的所有碳原子数为30。
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，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、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 PCTCN2021091703-appb-000020
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。
在本申请中，作为取代基的芳基例如但不限于苯基、联苯基、萘基、9,9-二甲基芴基、9,9-二苯基芴基、螺二芴基、蒽基、菲基、
Figure PCTCN2021091703-appb-000021
基。
在本申请中，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、烷氧基、烷硫基等基团取代。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、二苯并噻吩取代的苯基、吡啶取代的苯基等。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。
在本申请中，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、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如 N-吡啶基咔唑基)、N-烷基咔唑基(如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。
在本申请中，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、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。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。
在本申请中，作为取代基的杂芳基例如但不限于吡啶基、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。
在本申请中，碳原子数为1～10的烷基可以为直链烷基或支链烷基。具体而言，碳原子数为1～10的烷基可以为碳原子数1至10的直链烷基，或碳原子数3至10的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1～10的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、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
在本申请中，碳原子数为1～5的烷基可以为直链烷基或支链烷基。具体而言，碳原子数为1～10的烷基可以为碳原子数1至5的直链烷基，或碳原子数3至5的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5。碳原子数为1～5的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、环戊基等。
在本申请中，芳胺基是胺基(-NH 2)中的至少一个氢被芳香烃取代所形成的基团。例如，胺基(-NH 2)中的两个氢被苯取代的芳胺基为二苯胺基。示例性地，芳胺基可以选自苯胺基、二苯胺基、苄胺基、对硝基苯胺基、间硝基苯胺基、邻硝基苯胺基、N-甲基苯胺基、乙酰苯胺基、偶氮苯基、二甲苯胺基、N-对甲苯二胺基和N-间甲苯二胺基等。在本发明中，芳胺基可以选自二苯胺基、二萘基胺基。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021091703-appb-000022
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 PCTCN2021091703-appb-000023
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 PCTCN2021091703-appb-000024
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，下式(Y)中所示的，式(Y)所表示的取代基R基通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2021091703-appb-000025
在本申请中，卤素基团可以为氟、氯、溴、碘。
在本申请中，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。
在本申请中，三芳基硅基的具体实例包括但不限于，三苯基硅基等。
在本申请中，卤代烷基的具体实例包括但不限于三氟甲基。
下文中对于不定位连接或不定位取代的含义与此处相同，后续将不再进行赘述。
在本申请的一种具体实施方式中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～20的稠合芳环或者成环碳原子数为10～20的稠合杂芳环。
在本申请的一种具体实施方式中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～15的稠合芳环或者成环碳原子数为12～20的稠合杂芳环。
在本申请的一种具体实施方式中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯、萘、9,9-二甲基芴、菲、二苯并呋喃、二苯并噻吩或者N-苯基咔唑。
在本申请的一种具体实施方式中，所述有机化合物选自式(I-1)、式(I-2)、式(I-3)、式(I-4)、式(I-5)、式(I-6)、式(I-7)、式(I-8)或者式(I-9)：
Figure PCTCN2021091703-appb-000026
Figure PCTCN2021091703-appb-000027
在本申请的一种具体实施方式中，所述有机化合物选自以下式(II)所示的结构：
Figure PCTCN2021091703-appb-000028
其中，各Y 1、Y 2、Y 3、Y 4和Y 5彼此相同或不同，且各自独立地选自O、S、Si(R 8R 9)、C(R 10R 11)、N(R 12)、Se或者不存在，其中R 8、R 9、R 10、R 11和R 12彼此相同或不同，且各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者R 8和R 9相互连接以与它们共同连接的原子一起形成5～15元的饱和或不饱和环，或者R 10和R 11相互连接以与它们共同连接的原子一起形成5～15元的饱和或不饱和环；
q 1～q 5以q r表示，R 1～R 5以R r表示，r为变量，表示1～5的任意整数，q r表示取代基R r的个数；当r为1时，q r选自1；当r为2或5时，q r选自1、2、3；当r为3或4时，q r选自1、2；当q r大于1时，任意两个q r相同或者不相同。
在本申请中，式(II)中Y 1、Y 2、Y 3、Y 4、Y 5所连接的虚线“------”表示该虚线处可以形成连接键，也可以不形成连接键。具体来说，Y 1处的虚线表示Y 1可以在此虚线处形成连接键与苯环连接而成环，也可以不形成环，即不存在Y 1；Y 2处的虚线表示Y 2可以在此虚线处形成连接键与苯环连接而成环，也可以不形成环，即不存在Y 2；Y 3处的虚线表示Y 3可以在此虚线处形成连接键与苯环连接而成环，也可以不形成环，即不存在Y 3；Y 4处的虚线表示Y 4可以在此虚线处形成连接键与苯环连接而成环，也可以不形成环，即不存在Y 4；Y 5处的虚线表示Y 5可以在此虚线处形成连接键与苯环连接而成环，也可以不形成环，即不存在Y 5。Y 1、Y 2、Y 3、Y 4和Y 5中至少一者可以在虚线处形成连接键与苯环连接而形成环。
在本申请的一种具体实施方式中，所述有机化合物具有式(III)所示的结构：
Figure PCTCN2021091703-appb-000029
其中，各X 1、X 2、X 3、X 4和X 5彼此相同或不同，且各自独立地选自单键或者不存在，
p 1～p 5以p v表示，R 1～R 5以R v表示，v为变量，表示1～5的任意整数，p v表示取代基R v的个数；当v为1时，p v选自1；当v为2或5时，p v选自1、2、3；当v为3或4时，p v选自1、2；当p v大于1时，任意两个p v相同或者不相同。
在本申请的一种具体实施方式中，所述各R 1、R 2、R 3、R 4和R 5彼此相同或者不同，且分别独立地选自
Figure PCTCN2021091703-appb-000030
氢、氘、氰基、卤素基团、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、取代或未取代的碳原子数为1～10的烷基或者如下基团所组成的组，且各R 1、R 2、R 3、R 4和R 5中至少一者选自
Figure PCTCN2021091703-appb-000031
Figure PCTCN2021091703-appb-000032
其中，M 1选自单键或者
Figure PCTCN2021091703-appb-000033
G 1～G 5各自独立地选自N或者C(F 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(F 1)时，任意两个F 1相同或者不相同；
G 6～G 13各自独立地选自N或者C(F 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上 选自C(F 2)时，任意两个F 2相同或者不相同；
G 14～G 23各自独立地选自N或者C(F 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(F 3)时，任意两个F 3相同或者不相同；
G 24～G 33各自独立地选自N或者C(F 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(F 4)时，任意两个F 4相同或者不相同；
E 1选自氢、氘、氟、氯、溴、氰基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基；
各E 2～E 9、E 23彼此相同或不同，且各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～20的杂芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基；
各E 10～E 22、F 1～F 4彼此相同或不同，且各自独立地选自：氢、氘、氟、氯、溴、氰基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基，或者任意两个相邻的E 21相互连接形成环，或者任意两个相邻的E 22相互连接形成环；
e 1～e 23以e k表示，E 1～E 23以E k表示，k为变量，表示1～23的任意整数，e k表示取代基E k的个数；其中，当k选自8、17时，e k选自1、2或者3；当k选自3、4、5、13、15、18、19、23时，e k选自1、2、3或者4；当k选自1、2、6、7、9、16、21、22时，e k选自1、2、3、4或者5；当k选自14时，e k选自1、2、3、4、5或者6；当k选自10、20时，e k选自1、2、3、4、5、6或者7；当k选自12时，e k选自1、2、3、4、5、6、7或者8；当k选自11时，e k选自1、2、3、4、5、6、7、8或9；且当e k大于1时，任意两个E k相同或者不相同；
K 1选自O、S、Se、N(E 24)、C(E 25E 26)、Si(E 27E 28)；其中，各E 24、E 25、E 26、E 27、E 28彼此相同或不同，且各自独立地选自：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的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者上述E 25和E 26相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环，或者上述E 27和E 28相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
K 2选自单键、O、S、Se、N(E 29)、C(E 30E 31)、Si(E 32E 33)；其中，各E 29、E 30、E 31、E 32、E 33彼此相同或不同，且各自独立地选自：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的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者上述E 30和E 31相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环，或者上述E 32和E 33相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环，举例而言，在式i-15
Figure PCTCN2021091703-appb-000034
中，当M 1为单键时，E 20均为氢，K 2为单键，K 1为C(E 30E 31)时，任选地E 30和E 31相互连接以与它们共同连接的原子形成5～13元的饱和或不饱和环指的是：E 30和E 31可以相互连接形成一个环，也可以是相互独立地存在；当E 30和E 31成环时，该环的碳原子数可以是5元环，例如
Figure PCTCN2021091703-appb-000035
也可以是6元环，例如
Figure PCTCN2021091703-appb-000036
还可以是13元环，例如
Figure PCTCN2021091703-appb-000037
当然，E 30和E 31成环的碳原子数还可以为其他数值，此处不再一一列举，本申请不对此该环的碳原子数进行特殊限定。
在本申请的一种具体实施方式中，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
Figure PCTCN2021091703-appb-000038
氢、氘、氰基、氟、三甲基硅基、三苯基硅基、碳原子数为1～5的烷基、取代或未取代的基团W，所述未取代的基团W选自如下基团组成的组：
Figure PCTCN2021091703-appb-000039
所述基团W被取代时，基团W的取代基选自氘、氟、氯、氰基、三甲基硅基、三苯基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、吡啶基、嘧啶基、三嗪基、喹啉基、喹喔啉基、喹唑啉基、9,9-二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基；基团W中的取代基有多个时，多个取代基相同或不同。
在本申请的一种具体实施方式中，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
Figure PCTCN2021091703-appb-000040
氢、氘、氰基、氟、三甲基硅基、三苯基硅基、甲基、乙基、异丙基、 叔丁基、取代或未取代的碳原子数为6～15的芳基、取代或未取代的碳原子数为3～12的杂芳基、取代或未取代的碳原子数为6～12的芳胺基。
在本申请的一种具体实施方式中，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
Figure PCTCN2021091703-appb-000041
氢、氘、氰基、氟、三甲基硅基、三苯基硅基、甲基、乙基、异丙基、叔丁基或如下基团：
Figure PCTCN2021091703-appb-000042
在本申请的一种具体实施方式中，所述各R 1、R 2、R 3、R 4和R 5中的取代基彼此相同或不同，且各自独立地选自：氘、氟、氯、溴、氰基、苯基、萘基、联苯基、三甲基硅基、甲基、乙基、异丙基、叔丁基、吡啶基。
在本申请的一种具体实施方式中，所述有机化合物选自如下化合物所组成的组：
Figure PCTCN2021091703-appb-000043
Figure PCTCN2021091703-appb-000044
Figure PCTCN2021091703-appb-000045
Figure PCTCN2021091703-appb-000046
Figure PCTCN2021091703-appb-000047
Figure PCTCN2021091703-appb-000048
本申请对提供的有机化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的有机化合物结合合成实施例部分提供的制备方法确定合适的合成方法。换言之，本发明的合成实施例部分示例性地提供了有机化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有有机化合物，在此不再详述制备该有机化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
本申请第二方面提供一种电子元件，该电子元件包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层含有本申请第一方面所述的有机化合物。
在一种具体的实施方式中，所述功能层包括有机发光层，所述有机发光层含有所述有机化合物。有机发光层既可以由本申请所提供的有机化合物组成，也可以由本申请所提供的有机化合物和其他材料共同组成。所述有机发光层可以为一层或两层以上。
在本申请的一种具体实施方式中，所述电子元件为有机电致发光器件或光电转化器件。
在本申请的一种具体实施方式中，所述电子元件为有机电致发光器件，例如为红光器件或蓝光器件。
在本申请的一种具体实施方式中，电子元件可以为有机电致发光器件。如图1所示，有机电致发光器件可以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、作为能量转化层的有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至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，第一空穴传输层321和第二空穴传输层322分别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可以由化合物NPB组成。
可选地，有机发光层330可以由单一发光材料组成，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。
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。在本申请的一种实施方式中，有机发光层330的掺杂材料含有本申请的有机化合物。
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，苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种实施方式中，电子传输层340可以由TPBi和LiQ组成，或者由DBimiBphen和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，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和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层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可以由HAT-CN组成，或者由m-MTDATA组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层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可以包括LiQ，或者Mg和LiF。
按照另一种实施方式，电子元件可以为光电转化器件。如图3所示，该光电转化器件可以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包含本申请所提供的有机化合物。
按照一种具体的实施方式，如图3所示，光电转化器件可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，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、光电转化层、电子传输层和阴极，其中，光电转化层包含有本申请的有机化合物。
可选地，功能层300包括光电转化层360，光电转化层360包含本申请所提供的有机化合物。一种实施方式中，光电转化层360可以由本申请所提供的有机化合物组成；另一种实施方式中，光电转化层360可以由本申请所提供的化合物和其他材料共同组成。
本申请第三方面提供一种电子装置包含本申请第二方面所述的电子元件。
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包括上述光电转化器件。第二电子装置500例如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。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法，但是本公开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。
本申请中的中间体和化合物的分析检测使用ICP-7700质谱仪和M5000元素分析仪。
合成实施例
采用以下方法合成本发明的有机化合物：
合成实施例1～2：有机化合物10和有机化合物26的合成
Figure PCTCN2021091703-appb-000049
将镁条(13.54g，564mmol)和乙醚(100mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(100mg)，而后将溶有2’-溴-4-氯联苯(50.00g，187.0mmol)的乙醚(200mL)溶液缓慢滴入烧瓶中，滴加完毕后升温至35℃，搅拌3小时；将反应液降至0℃，向其中缓慢滴入溶有金刚烷酮(22.4g，149mmol)的乙醚(200mL)溶液，滴加完毕后升温至35℃，搅拌6小时，将反应液冷却至室温，向其中加入5％盐酸至pH<7，搅拌1小时，加入乙醚(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用乙酸乙酯/正庚烷(1:2)为流动相进行硅胶柱色谱提纯，得到白色固体的中间体A-1(34g，收率68％)。
Figure PCTCN2021091703-appb-000050
将中间体A-1(43g，126.9mmol)、三氟乙酸(36.93g，380.6mmol)和二氯甲烷(300mL)加入圆底烧瓶中，氮气保护下搅拌2小时；而后向反应液中加入氢氧化钠水溶液至pH＝8，分液，有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1:2)进行重结晶提纯，得到白色固体的中间体A-2(39.2g，收率96.3％)。
Figure PCTCN2021091703-appb-000051
将中间体A-2(20.4g，63.7mmol)、联硼酸频那醇酯(19.4g，76.5mmol)、三(二亚苄基丙酮)二钯(0.6g，0.6mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.6g，1.3mmol)、醋酸钾(12.5g，127.4mmol)和1,4-二氧六环(150mL)加入烧瓶中，氮气保护条件下于100℃回流搅拌16小时；降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体A-3(13.4g，收率51％)。
Figure PCTCN2021091703-appb-000052
将中间体A-3(13.3g，32.3mmol)、4-氯溴苯(6.7g，35.5mmol)、四(三苯基膦)钯(0.7g，
0.6mmol)、碳酸钾(11.1g，80.7mmol)、四丁基溴化铵(2.1g，6.5mmol)加入烧瓶中，并加入甲苯(80mL)、乙醇(20mL)和水(20mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌24小时，冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除 去溶剂，得到粗品，使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体A-4(8.85g，收率69％)。
Figure PCTCN2021091703-appb-000053
将中间体A-4(7.0g，17.46mmol)、苯胺(1.63g，17.46mmol)、三(二亚苄基丙酮)二钯(0.16g，0.17mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.14g，0.35mmol)以及叔丁醇钠(2.52g，26.18mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌3h，而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂，使用甲苯体系对粗品进行重结晶提纯，得到中间体A(5.6g，收率71％)。
Figure PCTCN2021091703-appb-000054
将二苯胺(2.9g，16.9mmol)加入盛有二甲苯(50mL)的圆底烧瓶中，之后加入叔丁醇钠(2.3g，23.8mmol)，加热体系温度至180℃，然后添加2,3-二氯溴苯(3.8g，16.9mmol)和四正丁基钛酸酯BTP(0.13g，0.238mmol)搅拌12h后将体系降温至室温，用氯化铵的水溶液淬灭反应，乙酸乙酯萃取有机相，使用无水硫酸镁进行干燥、过滤、减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1：2)进行硅胶柱色谱提纯，得到中间体B-1(3g，收率57％)。
Figure PCTCN2021091703-appb-000055
氮气保护下，将中间体A(2.56g，5.64mmol)溶于盛有50mL甲苯的圆底烧瓶中，加入叔丁醇钠(1.07g，12.3mmol)，开启搅拌，升高体系温度至110℃，然后依次加入中间体B-1(1.9g，6.11mmol)和四正丁基钛酸酯BTP(0.1g，0.18mmol)，搅拌12小时后，降至室温。加入氯化铵的水溶液淬灭反应，乙酸乙酯萃取有机相，使用无水硫酸镁进行干燥、过滤、减压除去溶剂。使用二氯甲烷/正庚烷(1：2)进行硅胶柱色谱提纯，得到白色固体状的中间体B-2(1.98g，收率48％)。
Figure PCTCN2021091703-appb-000056
氮气保护下，将中间体B-2(2.57g，3.52mmol)溶于盛有叔丁基苯(20mL)的圆底烧瓶中，滴加正丁基锂(2.5M，0.83mL)之后，将混合物加热至200℃保温6h，体系降至室温，液氮降温至-78℃，缓慢滴加三溴化硼(1M，1.6mL)，滴加完毕后，将反应重新加热至180℃，2h后用硫代硫酸钠的水溶液淬灭反应混合物，使用甲苯萃取有机相，无水硫酸镁进行干燥，过滤，减 压除去溶剂。使用甲苯进行重结晶提纯，得到有机化合物10(1.14g，产率46％)质谱：m/z＝705.3[M+H] +和有机化合物26(1.04g，产率42％)质谱：m/z＝705.3[M+H] +。
有机化合物26的核磁数据：
1H-NMR(400MHz,CD 2Cl 2):8.15(d,2H),8.09(d,2H),7.86-7.70(m,13H),7.60(t,1H),7.24-7.36(m,4H),7.09-6.94(m,3H),6.85(dd,1H),6.76(d,1H),1.89-2.15(m,10H),1.73(d,2H),1.57(s,2H)。
有机化合物10的核磁数据：
1H-NMR(400MHz,CD 2Cl 2):8.21(m,2H),8.03(d,1H),7.86-7.73(m,12H),7.62(t,1H),7.48(d,1H),7.21-7.11(m,2H),6.97-6.84(m,6H),6.76(d,2H),1.91-2.15(m,10H),1.71(d,2H),1.57(s,2H)。
Figure PCTCN2021091703-appb-000057
将中间体A(5g，11.02mmol)加入盛有二甲苯(50mL)的圆底烧瓶中，之后加入叔丁醇钠(3.3g，23.8mmol)，加热体系温度至180℃，然后添加2,3-二氯溴苯(2.5g，11.02mmol)和四正丁基钛酸酯BTP(0.13g，0.238mmol)搅拌12h后将体系降温至室温，用氯化铵的水溶液淬灭反应，乙酸乙酯萃取有机相，使用无水硫酸镁进行干燥、过滤、减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1：2)进行硅胶柱色谱提纯，得到中间体AA(4.1g，收率62.1％)。
Figure PCTCN2021091703-appb-000058
氮气保护下，将中间体A(2.05g，4.5mmol)溶于盛有50mL甲苯的圆底烧瓶中，加入叔丁醇钠(1.07g，12.3mmol)，开启搅拌，升高体系温度至110℃，然后依次加入中间体AA(3g，5.01mmol)和四正丁基钛酸酯BTP(0.1g，0.18mmol)，搅拌12小时后，降至室温。加入氯化铵的水溶液淬灭反应，乙酸乙酯萃取有机相，使用无水硫酸镁进行干燥、过滤、减压除去溶剂。使用二氯甲烷/正庚烷(1：2)进行硅胶柱色谱提纯，得到白色固体状的中间体3A(1.8g，收率35.4％)。
Figure PCTCN2021091703-appb-000059
氮气保护下，将中间体3A(1.8g，1.78mmol)溶于盛有叔丁基苯(20mL)的圆底烧瓶中，滴加正丁基锂(2.5M，0.53mL)之后，将混合物加热至200℃保温6h，体系降至室温，液氮降温至-78℃，缓慢滴加三溴化硼(1M，0.9mL)，滴加完毕后，将反应重新加热至180℃，2h后用硫代硫酸钠的水溶液淬灭反应混合物，使用甲苯萃取有机相，无水硫酸镁进行干燥，过滤，减压除去溶剂。使用甲苯进行重结晶提纯，得到有机化合物120(1.24g，产率66％)，质谱： m/z＝1057.3[M+H] +。
采用与合成中间体B-1相同的方法制备表1中的中间体S，不同之处仅在于，用表1中第1列的原料G代替合成实施例1中的二苯胺。
表1
Figure PCTCN2021091703-appb-000060
合成实施例3～10：有机化合物101～108的合成
Figure PCTCN2021091703-appb-000061
将2-溴苯硼酸(100.0g，500.0mmol)、1-氯-3碘苯(142.6g，597.6mmol)、四(三苯基膦)钯(11.5g，9.97mmol)、碳酸钾(102g，746mmol)、四丁基溴化铵(32.1g，99.6mmol)、甲苯(800mL)、乙醇(200mL)和去离子水(200mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌2小时；将反应液冷却至室温，加入甲苯(500mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯之后使用二氯甲烷/乙醇体系进行重结晶提纯，得到浅黄色固体中间体C-1(64.0g，收率为48％)。
Figure PCTCN2021091703-appb-000062
将镁条(13.54g，564mmol)和乙醚(100mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(100mg)。而后将溶有中间体C-1(64.00g，187.0mmol)的乙醚(200mL)溶液缓慢滴入烧瓶中，滴加完毕后升温至35℃，搅拌3小时；将反应液降至0℃，向其中缓慢滴入溶有金刚烷酮(22.45g，149mmol)的乙醚(200mL)溶液，滴加完毕后升温至35℃，搅拌6小时；将反应液冷却至室温，向其中加入5％盐酸至pH<7，搅拌1小时，加入乙醚(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到固体中间体C-2(24g，收率29％)。
Figure PCTCN2021091703-appb-000063
将中间体C-2(24g，71.0mmol)、三氟乙酸(40.48g，355.0mmol)和二氯甲烷(200mL)加入圆底烧瓶中，氮气保护下搅拌2小时；而后向反应液中加入氢氧化钠水溶液至pH＝8，分液，有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1:2)进行重结晶提纯，得到白色固体状中间体C-3(21g，收率92.5％)。
中间体C-3核磁数据为： 1H-NMR(400MHz,CDCl 2):8.11(d,1H),8.03(d,1H),7.41-7.63(m,2H),7.37-7.39(m,1H),7.30-7.33(m,1H),7.23-7.24(m,1H),2.88-2.93(m,2H),2.81-2.85(m,2H),2.19(s,2H),1.99(s,2H),1.77-1.83(m,4H),1.54(s,2H)
Figure PCTCN2021091703-appb-000064
将中间体C-3(10g，31.17mmol)、对氯苯硼酸(3.89g，24.93mmol)、四(三苯基膦)钯(0.72g，0.62mmol)、碳酸钾(6.45g，46.75mmol)、四丁基氯化铵(1.73g，6.23mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进 行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体C-4(7.5g，收率40.6％)。
Figure PCTCN2021091703-appb-000065
将镁条(13.54g，564mmol)和乙醚(100mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(100mg)。而后将溶有2’-溴-2-氯联苯(50.00g，187.0mmol)的乙醚(200mL)溶液缓慢滴入烧瓶中，滴加完毕后升温至35℃，搅拌3小时；将反应液降至0℃，向其中缓慢滴入溶有金刚烷酮(22.45g，149mmol)的乙醚(200mL)溶液，滴加完毕后升温至35℃，搅拌6小时；将反应液冷却至室温，向其中加入5％盐酸至pH<7，搅拌1小时，加入乙醚(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用乙酸乙酯/正庚烷(1:2)为流动相进行硅胶柱色谱提纯，得到白色固体中间体D-1(43g，68％)。
Figure PCTCN2021091703-appb-000066
将中间体D-1(43g，126.9mmol)、三氟乙酸(TFA)(36.93g，380.6mmol)和二氯甲烷(MC)(300mL)加入圆底烧瓶中，氮气保护下搅拌2小时；而后向反应液中加入氢氧化钠水溶液至pH＝8，分液，有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1:2)进行硅胶柱色谱提纯，得到白色固体状中间体D-2(39.2g，96.3％)。
Figure PCTCN2021091703-appb-000067
将中间体D-2(10g，31.17mmol)、对氯苯硼酸(3.89g，24.93mmol)、四(三苯基膦)钯(0.72g，0.62mmol)、碳酸钾(6.45g，46.75mmol)、四丁基氯化铵(1.73g，6.23mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体D-3(7.8g，收率61.6％)。
除了使用下表2中第一列原料M代替4-氯溴苯，第二列中间体L代替中间体A-3外，采用与中间体A-4相同的合成方法合成以下中间体LM。
表2
Figure PCTCN2021091703-appb-000068
Figure PCTCN2021091703-appb-000069
采用与合成实施例1相同的方法制备表3的中间体NA，不同之处仅在于，用表3中第1列的原料1代替合成实施例1中的中间体A-4，用原料2代替合成实施例1中的苯胺，来合成表3中第3列的中间体NA。
表3
Figure PCTCN2021091703-appb-000070
Figure PCTCN2021091703-appb-000071
Figure PCTCN2021091703-appb-000072
采用与合成实施例1相同的合成方法合成表4中的有机化合物，不同之处在于，用表4中第2列的中间体NA代替合成实施例1中的中间体A，用表4中第3列的中间体S代替中间体B-1，最终合成以下有机化合物。最终制备得到的化合物的结构及表征数据见表4。
表4
Figure PCTCN2021091703-appb-000073
Figure PCTCN2021091703-appb-000074
Figure PCTCN2021091703-appb-000075
Figure PCTCN2021091703-appb-000076
采用以下方法进行蓝色有机电致发光器件的制作：
实施例1：蓝色有机电致发光器件的制作
通过以下过程制备阳极：将厚度为
Figure PCTCN2021091703-appb-000077
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2：N 2等离子进行表面处理，以增加阳极(实验基板)的功函数，接着清除浮渣。
在实验基板(阳极)上真空蒸镀m-MTDATA(4,4',4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺)以形成厚度为
Figure PCTCN2021091703-appb-000078
的空穴注入层(HIL)。
在空穴注入层(HIL)上真空蒸镀NPB(CAS：495416-60-9)，以形成厚度为
Figure PCTCN2021091703-appb-000079
的第一空穴传输层(HTL-1)。
在第一空穴传输层上蒸镀TCTA(4,4',4”-三(咔唑-9-基)三苯胺)，形成厚度为
Figure PCTCN2021091703-appb-000080
的第二空穴传输层(HTL-2)。
将α,β-ADN有机发光层的主体材料(Host)，将化合物10作为有机发光层的掺杂材料(Dopant)，主体材料和掺杂材料按照30：3的膜厚比进行蒸镀，形成了厚度为
Figure PCTCN2021091703-appb-000081
的有机发光层(EML)。
将DBimiBphen(4,7-Diphenyl-2,9-bis(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-1,10-phenanthroline)和LiQ(8-羟基喹啉-锂)以1：1的重量比共同蒸镀形成
Figure PCTCN2021091703-appb-000082
厚的电子传输层(ETL)。
将Mg和LiF按照1：1的重量比共同蒸镀在电子传输层上(ETL)，以形成厚度为
Figure PCTCN2021091703-appb-000083
的混合膜层作为电子注入层(EIL)。
将镁(Mg)和银(Ag)以1：9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021091703-appb-000084
的阴极。
在上述阴极上蒸镀厚度为
Figure PCTCN2021091703-appb-000085
的CP-1，形成有机覆盖层(CPL)，从而完成有机电致发光器件的制造。器件性能见表6。
其中，有机材料的蒸镀速率为
Figure PCTCN2021091703-appb-000086
金属材料的蒸镀速率为
Figure PCTCN2021091703-appb-000087
m-MTDATA、NPB、TCTA、α,β-ADN、DBimiBphen和LiQ的结构式如下：
Figure PCTCN2021091703-appb-000088
Figure PCTCN2021091703-appb-000089
实施例2～24
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备有机发光层(EML)时，将化合物10(发光层掺杂材料Dopant)分别更换为表6中所示的有机化合物。
对比例1
采用与实施例1相同的方法制作有机电致发光器件，不同之处仅在于，在制备有机发光层(EML)时，将化合物10(发光层掺杂材料Dopant)更换为化合物BD-1，化合物BD-1的结构见表5。
对比例2
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备有机发光层(EML)时，将化合物10(发光层掺杂材料Dopant)更换为化合物BD-2，化合物BD-2的结构见表5。
对比例3
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备有机发光层(EML)时，将化合物10(发光层掺杂材料Dopant)更换为化合物BD-3，化合物BD-3的结构见表5。
表5 对比例使用的材料结构
Figure PCTCN2021091703-appb-000090
对实施例和对比例制备的有机电致发光器件进行性能测试，测试的方法和条件包括：在恒定电流密度10mA/cm 2下进行测试，T95器件寿命在恒定电流密度20mA/cm 2下进行测试，测试结果见表6。
表6
Figure PCTCN2021091703-appb-000091
Figure PCTCN2021091703-appb-000092
由表6可知，由本发明化合物制备的实施例1～24与对比例1～3相比，实施例1～24的有机电致发光器件具有高发光效率、长寿命的特性。具体来说，实施例1～24的有机电致发光器件与比较例相比发光效率至少提升了10.7％，寿命至少提升了13.1％。这是由于本发明的有机化合物中具有金刚烷-芴基结构，将金刚烷-芴基连接在母核的末端而非直接连在母核上，能够降低化合物的对称性，进而提高材料的成膜性。且引入该基团能够提升整个含氮化合物的共轭体系的电子密度，并提高含氮化合物的空穴传导效率，进而提高有机电致发光器件和光电转化器件的载流子传导效率以及寿命。将金刚烷-芴形成的化合物与以硼元素为中心的实心环结合，可以大大的提高载流子的稳定性，改善有机发光器件的发光性能。
综上所述，本专利公开的化合物用于有机电致发光器件中，使得包含该化合物的有机电致发光器件具有更高的效率以及更好的寿命。
本领域技术人员在考虑说明书及实践后，将容易想到本公开的其它实施方案。本申请旨在涵盖本公开的任何变型、用途或者适应性变化，这些变型、用途或者适应性变化遵循本公开的一般性原理并包括本技术领域中的公知常识或惯用技术手段。说明书和实施例仅被视为示例性的，本公开的真正范围和精神由所附的权利要求指出.
以上结合附图详细描述了本公开的优选实施方式，但是，本公开并不限于上述实施方式中的具体细节，在本公开的技术构思范围内，可以对本公开的技术方案进行多种简单变型，这些简单变型均属于本公开的保护范围。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下， 可以通过任何合适的方式进行组合，为了避免不必要的重复，本公开对各种可能的组合方式不再另行说明。
此外，本公开的各种不同的实施方式之间也可以进行任意组合，只要其不违背本公开的思想，其同样应当视为本公开所公开的内容。

Claims (15)

  1. 一种有机化合物，该有机化合物具有如下式(I)所示的结构：
    Figure PCTCN2021091703-appb-100001
    其中，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～30的稠合芳环、成环碳原子数为10～30的稠合杂芳环；
    各R 1、R 2、R 3、R 4和R 5彼此相同或不同，且分别独立地选自
    Figure PCTCN2021091703-appb-100002
    氢、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18～24的三芳基硅基、取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为1～10的烷氧基、取代或未取代的碳原子数为6～30的芳胺基、取代或未取代的碳原子数为6～30的芳基或者取代或未取代的碳原子数为2～30的杂芳基，且R 1、R 2、R 3、R 4和R 5中至少一者选自
    Figure PCTCN2021091703-appb-100003
    表示化学键；
    或者任意两个相邻的R 1相互连接形成环，或者任意相邻的R 1与R 2相互连接形成环，或者任意相邻的R 2与R 3相互连接形成环，或者任意相邻的R 3与R 4相互连接形成环，或者任意相邻的R 4与R 5相互连接形成环，或者任意相邻的R 1与R 5相互连接形成环；
    各R 6和R 7彼此相同或不同，且分别独立地选自氢、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18～24的三芳基硅基、未取代的碳原子数为1～10的烷基、未取代的碳原子数为3～10的环烷基、未取代的碳原子数为1～10的烷氧基、未取代的碳原子数为6～30的芳基或者未取代的碳原子数为2～30的杂芳基，或者任意两个相邻的R 6相互连接形成环，或者任意两个相邻的R 7相互连接形成环；
    n 1-n 7以n t表示，R 1～R 7以R t表示，t为变量，表示1～7的任意整数，n t表示取代基R t的个数；当t为1或6时，n t选自1、2、3；当t为2、3、4或5时，n t选自1、2、3、4、5、6、7、8、9、10、11、12；当t为7时，n t选自1、2、3、4；当n t大于1时，任意两个R t相同或者不相同；
    各R 1、R 2、R 3、R 4和R 5中的取代基彼此相同或不同，且各自独立地选自：氘、氟、氯、溴、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基。
  2. 根据权利要求1所述的有机化合物，其特征在于，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯环、成环碳原子数为10～15的稠合芳环或者成环碳原子数为12～20的稠合杂芳环。
  3. 根据权利要求1或2所述的有机化合物，其特征在于，A 1、A 2、A 3和A 4彼此相同或不同，且各自独立地选自苯、萘、9,9-二甲基芴、菲、二苯并呋喃、二苯并噻吩或者N-苯基咔唑。
  4. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自式(I-1)、式(I-2)、式(I-3)、式(I-4)、式(I-5)、式(I-6)、式(I-7)、式(I-8)或者式(I-9)所示的化合物：
    Figure PCTCN2021091703-appb-100004
  5. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物具有式(II)所示的结构：
    Figure PCTCN2021091703-appb-100005
    其中，各Y 1、Y 2、Y 3、Y 4和Y 5彼此相同或不同，且各自独立地选自O、S、Si(R 8R 9)、C(R 10R 11)、N(R 12)、Se或者不存在，其中R 8、R 9、R 10、R 11和R 12彼此相同或不同，且各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者R 8和R 9相互连接以与它们共同连接的原子一起形成5～15元的饱和或不饱和环，或者R 10和R 11相互连接以与它们共同连接的原子一起形成5～15元的饱和或不饱和环；
    q 1～q 5以q r表示，R 1～R 5以R r表示，r为变量，表示1～5的任意整数，q r表示取代基R r的个数；当r为1时，q r选自1；当r为2或5时，q r选自1、2、3；当r为3或4时，q r选自1、2；当q r大于1时，任意两个q r相同或者不相同。
  6. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物具有式(III)所示的结构：
    Figure PCTCN2021091703-appb-100006
    其中，各X 1、X 2、X 3、X 4和X 5彼此相同或不同，且各自独立地选自单键或者不存在，
    p 1～p 5以p v表示，R 1～R 5以R v表示，v为变量，表示1～5的任意整数，p v表示取代基R v的个数；当v为1时，p v为1；当v为2或5时，p v选自1、2、3；当v为3或4时，p v选自1、2；当p v大于1时，任意两个p v相同或者不相同。
  7. 根据权利要求1所述的有机化合物，其中，所述各R 1、R 2、R 3、R 4和R 5彼此相同或者不同，且分别独立地选自
    Figure PCTCN2021091703-appb-100007
    氢、氘、氰基、卤素基团、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、取代或未取代的碳原子数为1～10的烷基或者如下基团所组成的组：
    Figure PCTCN2021091703-appb-100008
    Figure PCTCN2021091703-appb-100009
    其中，M 1选自单键或者
    Figure PCTCN2021091703-appb-100010
    G 1～G 5各自独立地选自N或者C(F 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(F 1)时，任意两个F 1相同或者不相同；
    G 6～G 13各自独立地选自N或者C(F 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(F 2)时，任意两个F 2相同或者不相同；
    G 14～G 23各自独立地选自N或者C(F 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(F 3)时，任意两个F 3相同或者不相同；
    G 24～G 33各自独立地选自N或者C(F 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(F 4)时，任意两个F 4相同或者不相同；
    E 1选自氢、氘、氟、氯、溴、氰基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基；
    各E 2～E 9、E 23彼此相同或不同，且各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～20的杂芳基、碳原子数为3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基；
    各E 10～E 22、F 1～F 4彼此相同或不同，且各自独立地选自：氢、氘、氟、氯、溴、氰基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷胺基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的烷基磺酰基、碳原子数为3～18的三烷基膦基、碳原子数为3～18的三烷基硼基，或者任意两个相邻的E 21相互连接形成环，或者任意两个相邻的E 22相互连接形成环；
    e 1～e 23以e k表示，E 1～E 23以E k表示，k为变量，表示1～23的任意整数，e k表示取代基E k的个数；其中，当k选自8、17时，e k选自1、2或者3；当k选自3、4、5、13、15、18、19、23时，e k选自1、2、3或者4；当k选自1、2、6、7、9、16、21、22时，e k选自1、2、3、4或者5；当k 选自14时，e k选自1、2、3、4、5或者6；当k选自10、20时，e k选自1、2、3、4、5、6或者7；当k选自12时，e k选自1、2、3、4、5、6、7或者8；当k选自11时，e k选自1、2、3、4、5、6、7、8或9；且当e k大于1时，任意两个E k相同或者不相同；
    K 1选自O、S、Se、N(E 24)、C(E 25E 26)、Si(E 27E 28)；其中，各E 24、E 25、E 26、E 27、E 28彼此相同或不同，且各自独立地选自：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的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者上述E 25和E 26相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环，或者上述E 27和E 28相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
    K 2选自单键、O、S、Se、N(E 29)、C(E 30E 31)、Si(E 32E 33)；其中，各E 29、E 30、E 31、E 32、E 33彼此相同或不同，且各自独立地选自：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的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者上述E 30和E 31相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环，或者上述E 32和E 33相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环。
  8. 根据权利要求1所述的有机化合物，其特征在于，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
    Figure PCTCN2021091703-appb-100011
    氢、氘、氰基、氟、三甲基硅基、三苯基硅基、碳原子数为1～5的烷基、取代或未取代的基团W，所述未取代的基团W选自如下基团组成的组：
    Figure PCTCN2021091703-appb-100012
    所述基团W被取代时，基团W中的取代基选自氘、氟、氯、氰基、三甲基硅基、三苯基硅基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、吡啶基、嘧啶基、三嗪基、喹啉基、喹喔啉基、喹唑啉基、9,9-二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基；基团W中的取代基有多个时，多个取代基相同或不同。
  9. 根据权利要求1所述的有机化合物，其特征在于，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
    Figure PCTCN2021091703-appb-100013
    氢、氘、氰基、氟、三甲基硅基、三苯基硅基、甲基、 乙基、异丙基、叔丁基、取代或未取代的碳原子数为6～15的芳基、取代或未取代的碳原子数为3～12的杂芳基、取代或未取代的碳原子数为6～12的芳胺基。
  10. 根据权利要求1所述的有机化合物，其特征在于，所述各R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自
    Figure PCTCN2021091703-appb-100014
    氢、氘、氰基、氟、三甲基硅基、三苯基硅基、甲基、乙基、异丙基、叔丁基或如下基团：
    Figure PCTCN2021091703-appb-100015
  11. 根据权利要求1所述的有机化合物，其特征在于，所述各R 1、R 2、R 3、R 4和R 5中的取代基彼此相同或不同，且各自独立地选自：氘、氟、氯、溴、氰基、苯基、萘基、联苯基、三甲基硅基、甲基、乙基、异丙基、叔丁基、吡啶基。
  12. 根据权利要求1所述的有机化合物，其特征在于，所述有机化合物选自如下化合物所组成的组：
    Figure PCTCN2021091703-appb-100016
    Figure PCTCN2021091703-appb-100017
    Figure PCTCN2021091703-appb-100018
    Figure PCTCN2021091703-appb-100019
    Figure PCTCN2021091703-appb-100020
    Figure PCTCN2021091703-appb-100021
  13. 一种电子元件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层含有权利要求1～12任一项所述的有机化合物。
  14. 根据权利要求13所述的电子元件，其中，所述功能层包括有机发光层，所述有机发光层含有权利要求1～12任一项所述的有机化合物。
  15. 一种电子装置，包括权利要求13或14所述的电子元件。
PCT/CN2021/091703 2020-05-08 2021-04-30 一种有机化合物和应用以及使用其的有机电致发光器件和电子装置 WO2021223688A1 (zh)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN202010383434.X 2020-05-08
CN202010383434 2020-05-08
CN202011140241.8 2020-10-22
CN202011140241.8A CN112250701B (zh) 2020-05-08 2020-10-22 一种有机化合物以及使用其的电子元件和电子装置

Publications (1)

Publication Number Publication Date
WO2021223688A1 true WO2021223688A1 (zh) 2021-11-11

Family

ID=74264023

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2021/091703 WO2021223688A1 (zh) 2020-05-08 2021-04-30 一种有机化合物和应用以及使用其的有机电致发光器件和电子装置

Country Status (2)

Country Link
CN (1) CN112250701B (zh)
WO (1) WO2021223688A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024013709A1 (en) 2022-07-14 2024-01-18 Idemitsu Kosan Co., Ltd. Compound and an organic electroluminescence device comprising the compound
WO2024169626A1 (zh) * 2023-02-16 2024-08-22 广东阿格蕾雅光电材料有限公司 一种金属络合物及电致发光器件

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117186130A (zh) * 2021-07-01 2023-12-08 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的有机电致发光器件和电子装置
CN113527345A (zh) * 2021-07-02 2021-10-22 常州大学 螺手性硼氮类cpmr-tadf发光材料及其应用
CN113651703B (zh) * 2021-07-20 2024-03-19 陕西莱特迈思光电材料有限公司 有机化合物、电子元件和电子装置
EP4151697A1 (en) 2021-09-17 2023-03-22 Idemitsu Kosan Co., Ltd. Compound and an organic electroluminescence device comprising the compound
CN114230594B (zh) * 2021-11-15 2024-02-27 深圳大学 一种含重原子的硼氮杂化合物及其制备方法、有机电致发光器件
CN114230597B (zh) * 2021-12-29 2023-12-26 武汉天马微电子有限公司 一种有机化合物及其应用
WO2024185711A1 (ja) * 2023-03-03 2024-09-12 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019102936A1 (ja) * 2017-11-24 2019-05-31 学校法人関西学院 有機デバイス用材料およびそれを用いた有機電界発光素子
CN110662750A (zh) * 2017-05-22 2020-01-07 材料科学有限公司 有机化合物及包含该有机化合物的有机电致发光元件
WO2020080872A1 (ko) * 2018-10-18 2020-04-23 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107406759B (zh) * 2015-03-09 2020-10-30 学校法人关西学院 多环芳香族化合物及发光层形成用组合物与其用途
US20190312207A1 (en) * 2017-02-16 2019-10-10 Kwansei Gakuin Educational Foundation Organic electroluminescent element
KR101990818B1 (ko) * 2018-05-04 2019-06-19 머티어리얼사이언스 주식회사 유기전계발광소자

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110662750A (zh) * 2017-05-22 2020-01-07 材料科学有限公司 有机化合物及包含该有机化合物的有机电致发光元件
WO2019102936A1 (ja) * 2017-11-24 2019-05-31 学校法人関西学院 有機デバイス用材料およびそれを用いた有機電界発光素子
WO2020080872A1 (ko) * 2018-10-18 2020-04-23 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024013709A1 (en) 2022-07-14 2024-01-18 Idemitsu Kosan Co., Ltd. Compound and an organic electroluminescence device comprising the compound
WO2024169626A1 (zh) * 2023-02-16 2024-08-22 广东阿格蕾雅光电材料有限公司 一种金属络合物及电致发光器件

Also Published As

Publication number Publication date
CN112250701A (zh) 2021-01-22
CN112250701B (zh) 2023-02-24

Similar Documents

Publication Publication Date Title
WO2021223688A1 (zh) 一种有机化合物和应用以及使用其的有机电致发光器件和电子装置
CN113501800B (zh) 有机电致发光材料、电子元件及电子装置
WO2021213109A1 (zh) 一种芳胺化合物、使用其的电子元件及电子装置
CN111777517B (zh) 一种含氮化合物以及使用其的电子元件和电子装置
WO2021135750A1 (zh) 一种有机化合物、其应用以及有机电致发光器件
CN113717059B (zh) 一种有机化合物及包含其的电子元件和电子装置
JP7105388B1 (ja) 窒素含有化合物、電子部品及び電子装置
CN113285038B (zh) 一种有机电致发光器件及电子装置
WO2021135516A1 (zh) 有机化合物、电子元件和电子装置
CN113121408A (zh) 含氮化合物、电子元件和电子装置
WO2022206389A1 (zh) 含氮化合物及包含其的电子元件和电子装置
CN115521214B (zh) 有机化合物及包含其的电子元件和电子装置
WO2023273416A1 (zh) 有机化合物、有机电致发光器件和电子装置
CN115784904A (zh) 含氮化合物和电子元件及电子装置
CN114989069A (zh) 含氮化合物和电子元件及电子装置
WO2024007511A1 (zh) 芳胺化合物及有机电致发光器件和电子装置
CN115650899B (zh) 含氮化合物、电子元件和电子装置
CN114181166B (zh) 有机化合物及包含其的电子元件和电子装置
CN113896720B (zh) 有机化合物、电子元件及电子装置
CN113651703B (zh) 有机化合物、电子元件和电子装置
CN115521212A (zh) 有机材料、电子元件和电子装置
CN113782689A (zh) 用于有机光电装置的组合物、有机光电装置及显示装置
CN114621253B (zh) 含氮化合物以及使用其的电子元件和电子装置
CN114716443B (zh) 有机化合物以及使用其的有机电致发光器件和电子装置
CN114539262B (zh) 有机化合物及包含其的电子元件和电子装置

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21800704

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21800704

Country of ref document: EP

Kind code of ref document: A1