WO2021135750A1 - 一种有机化合物、其应用以及有机电致发光器件 - Google Patents

一种有机化合物、其应用以及有机电致发光器件 Download PDF

Info

Publication number
WO2021135750A1
WO2021135750A1 PCT/CN2020/131873 CN2020131873W WO2021135750A1 WO 2021135750 A1 WO2021135750 A1 WO 2021135750A1 CN 2020131873 W CN2020131873 W CN 2020131873W WO 2021135750 A1 WO2021135750 A1 WO 2021135750A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
unsubstituted
group
ring
same
Prior art date
Application number
PCT/CN2020/131873
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
Priority to KR1020217043405A priority Critical patent/KR102631942B1/ko
Priority to US17/623,319 priority patent/US20220306655A1/en
Publication of WO2021135750A1 publication Critical patent/WO2021135750A1/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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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 relates to the technical field of organic light-emitting materials, in particular, to an organic compound, its application, and an organic electroluminescent device.
  • 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 film layers 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 electroluminescence device as an example, it generally includes an anode, a hole transport layer, an electroluminescence 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 electroluminescent layer, and the holes on the anode side also move to the light emitting layer. The electrons and holes are in the electroluminescent layer. Combining to form excitons, the excitons are in an excited state and release energy to the outside, so that the electroluminescent layer emits light to the outside.
  • the purpose of this application is to improve the luminous efficiency of the electroluminescent device and prolong its service life.
  • the first aspect of the present application provides a compound having a structure represented by the following formula (1):
  • At least one of Q 1 , Q 2 and Q 3 is Represents the connection key
  • n 1 and n 2 are the same or different, and are independently selected from 0, 1, 2, 3, 4;
  • n 3 and n 4 are the same or different, and are independently selected from 0, 1, 2, 3, 4, and 5;
  • n 5 is selected from 0, 1, 2, 3;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted Substituted aryl groups with 6-40 carbon atoms, substituted or unsubstituted heteroaryl groups with 2-40 carbon atoms, substituted or unsubstituted arylamino groups with 6-40 carbon atoms;
  • R 1 and R 2 are connected to each other to form a ring
  • two adjacent R 2 and R 3 are connected to each other to form a ring
  • two adjacent R 3 and R 4 are connected to each other to form a ring
  • Two adjacent R 4 and R 5 are connected to each other to form a ring
  • two adjacent R 1 and R 4 are connected to each other to form a ring
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, and unsubstituted alkyl with 1-30 carbon atoms , Unsubstituted cycloalkyl with 3-30 carbon atoms, unsubstituted heterocycloalkyl with 2-30 carbon atoms, and carbon atoms optionally substituted by alkyl with 1-5 carbon atoms
  • the arylamino group is an unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and an unsubstituted arylsilyl group having 6 to 30 carbon atoms.
  • the second aspect of the application provides an application of the organic compound provided in the first aspect of the application in an organic electroluminescent device.
  • the third aspect of the present application provides an organic electroluminescent device, including an anode, a cathode, and at least one functional layer between the anode and the cathode.
  • the functional layer includes a hole injection layer, a hole transport layer, and An electroluminescence layer, an electron transport layer and an electron injection layer, the organic electroluminescence layer contains the organic compound provided in the first aspect of the present application.
  • the organic compound of the present application has an adamantane-six-membered ring-based structure, which is combined with a solid ring centered on boron, which is beneficial to improve the electronic stability, prevent the disappearance of excitons, and promote the energy transfer of the main body. It can significantly improve the stability of carriers and improve the light-emitting performance of organic light-emitting devices.
  • the driving voltage of the organic electroluminescence device containing the organic compound of the present application can be reduced, and the open circuit voltage of the photoelectric conversion device can be increased.
  • 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 an 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 electro-induced Emitting layer; 340, electron transport layer; 350, electron injection layer; 400, electronic device.
  • the first aspect of the application provides an organic compound, which has a structure represented by the following formula (1):
  • At least one of Q 1 , Q 2 and Q 3 is Represents the connection key
  • n 1 and n 2 are the same or different, and are independently selected from 0, 1, 2, 3, 4;
  • n 3 and n 4 are the same or different, and are independently selected from 0, 1, 2, 3, 4, and 5;
  • n 5 is selected from 0, 1, 2, 3;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted Substituted aryl groups with 6-40 carbon atoms, substituted or unsubstituted heteroaryl groups with 2-40 carbon atoms, substituted or unsubstituted arylamino groups with 6-40 carbon atoms,
  • any two adjacent R 1 and R 2 are connected to each other to form The ring
  • the ring may exist in the form of a saturated or unsaturated ring, or may exist independently of each other. For example, when two adjacent R 1 and R 2 , two adjacent R 2 and R 3 , two adjacent R 3 and R 4 , and two adjacent R 4 and R 5 form a ring
  • the way of ring formation such as
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, and unsubstituted alkyl with 1-30 carbon atoms , Unsubstituted cycloalkyl with 3-30 carbon atoms, unsubstituted heterocycloalkyl with 2-30 carbon atoms, and carbon atoms optionally substituted by alkyl with 1-5 carbon atoms
  • At least one of Q 1 , Q 2 and Q 3 is "Means that one of Q 1 , Q 2 and Q 3 is Or two of Q 1 , Q 2 and Q 3 are Or three of Q 1 , Q 2 and Q 3 are
  • the dotted line "------" in formula (1) indicates that a connecting key may or may not be formed at the dotted line.
  • the dashed line at Q 3 indicates that Q 3 can form a bond at this dashed line to connect to the benzene ring to form a ring, or it may not form a bond, and is not connected to the benzene ring to form a ring;
  • the dashed line at Q 2 indicates Q 2 can form a bond at this dotted line to connect with the benzene ring to form a ring, or it may not form a bond, or connect with the benzene ring to form a ring;
  • the dotted line at Q 1 indicates that Q 1 can form a bond at this dotted line It is connected to the benzene ring to form a ring, or it may not form a bond, and it may not be connected to the benzene ring to form a ring.
  • n 1 , n 2 , n 3 , n 4 , and n 5 are selected from 0, the benzene ring is not substituted.
  • n 1 is the number of substituents R 1 , when n 1 is greater than or equal to 2, any two R 1 are the same or different;
  • n 2 is the number of substituents R 2 , when n 2 is greater than or equal to 2.
  • n 3 is the number of substituent R 3 , when n 3 is greater than or equal to 2, any two R 3 are the same or different;
  • n 4 is the number of substituent R 4, when When n 4 is greater than or equal to 2, any two R 4 are the same or different;
  • n 5 is the number of substituent R 5 , and when n 5 is greater than or equal to 2, any two R 5 are the same or different.
  • the boron element in the organic compound forms a solid ring structure with the central arylamine.
  • Combining boron-based amines with electron-rich spiroaryl amines can improve electronic stability, prevent excitons from disappearing, and facilitate the energy transfer of the host, thereby maximizing efficiency.
  • Linking adamantane-six-membered ring with a solid ring with boron as the core, due to the alkane structure of adamantane can greatly reduce the ⁇ - ⁇ stacking effect of the molecule, significantly improve the stability of the carrier, and then improve the organic light-emitting device The luminous performance.
  • the organic electroluminescence device containing the organic compound has higher luminous efficiency and longer service life.
  • the number of carbon atoms of R 1 , R 2 , R 3 , R 4 and R 5 refers to the number of all carbon atoms.
  • R 1 , R 2 , R 3 , R 4 and R 5 are selected from substituted aryl groups with 18 carbon atoms, all carbon atoms of the aryl group and the substituents thereon are 18; if R 1 , R 2 , R 3 , R 4 and R 5 are selected from substituted alkyl groups with 10 carbon atoms, then all carbon atoms of the alkyl group and the substituents thereon are 10; if R 1 , R 2 , R 3 , R 4 and R 5 are selected from substituted heteroaryl groups with 10 carbon atoms, then all carbon atoms of the heteroaryl group and its substituents are 10; if R 1 , R 2 , R 3 , R 4 and R 5 are selected from substituted arylamino groups with 10 carbon atoms, and all carbon atoms
  • 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” may be the same or different from each other, each R" may be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for 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 substituents, namely Rc can be, for example, deuterium, halogen groups, cyano groups, heteroaryl groups with 3-20 carbon atoms, aryl groups with 6-20 carbon atoms, and those with 3-12 carbon atoms.
  • Trialkylsilyl group triarylsilyl group with 18-30 carbon atoms, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, alkene with 2-6 carbon atoms Group, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, Heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylamino with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, carbon An aryloxy group with 6-18 atoms, an arylthio group with 6-18 carbon atoms, an alkylsulfonyl group with 6-18 carbon atoms, a trialkylphosphino group with 3-18 carbon atoms, A trialkylboron group having 3-18 carbon atoms.
  • any two adjacent substituents form a ring may include two substituents on the same atom, and may also include two adjacent atoms each having one Substituents; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom to which they are connected together (for example, a saturated or unsaturated ring with 3 to 18 members); When two adjacent atoms each have a substituent, the two substituents can be fused to form a ring, such as a naphthalene ring, a phenanthrene ring, and an anthracene ring.
  • a ring such as a naphthalene ring, a phenanthrene ring, and an anthracene ring.
  • hetero means that a functional group includes at least one heteroatom such as B, O, N, P, Si, Se, or S, and the remaining atoms are carbon and hydrogen.
  • the unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.
  • alkyl may include linear or branched alkyl.
  • Alkyl groups can have 1 to 20 carbon atoms.
  • a numerical range such as “1 to 20” refers to each integer in the given range; for example, “1 to 20 carbon atoms” means that it can contain 1 Carbon atoms, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 Carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms base.
  • the alkyl group may also be a medium-sized alkyl group having 1 to 10 carbon atoms.
  • the alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms.
  • the alkyl group may be substituted or unsubstituted.
  • alkyl groups having 1-10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl Base, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, etc.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, and A monocyclic aryl group and a condensed ring aryl group conjugated by carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application.
  • the aryl group does not contain heteroatoms such as B, O, N, P, Si, Se, or S.
  • phenyl, biphenyl, etc. are aryl groups.
  • aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10 ]Phenanthryl, pyrenyl, benzofluoranthene, Base, fluorenyl, etc., but not limited to this.
  • a substituted aryl group means that one or more hydrogen atoms in the aryl group are replaced by other groups.
  • at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylamino, aryl, heteroaryl Group or other groups.
  • the substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18.
  • the number of carbon atoms of 9,9-dimethylfluorenyl is 15.
  • aryl groups as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, phenanthryl, anthracenyl , 1,10-phenanthroline group, etc.
  • the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si, Se, and S as a heteroatom.
  • 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, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazole Group, benzothiazolyl, benzo, be
  • heteroaryl groups are not limited thereto.
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system
  • N-arylcarbazolyl, N-heteroarylcarbazolyl, phenyl-substituted dibenzofuranyl, Dibenzofuranyl-substituted phenyl groups and the like are heteroaryl groups of multiple aromatic ring systems conjugated through carbon-carbon bonds.
  • the heteroaryl group may be carbazolyl, dibenzofuranyl and the like.
  • the heteroaryl group as a substituent includes, but is not limited to, pyridyl, carbazolyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, pyrazine Group, dibenzothienyl, dibenzofuranyl, 9,9-dimethyl-9H-9-silicofluorene, 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 group, diphenylamino group, benzylamino group, N-methyl anilino group, dimethylanilino group, xylamino group, N-p-toluene diamino group and N-m-toluene diamino group, etc.
  • the arylamine group may be selected from diphenylamino group and dinaphthylamino group.
  • the compound has a structure represented by the following formula (1):
  • At least one of Q 1 , Q 2 and Q 3 is Represents the connection key
  • n 1 and n 2 are the same or different, and are independently 0, 1, 2, 3, 4;
  • n 3 and n 4 are the same or different, and are independently 0, 1, 2, 3, 4, 5;
  • n 5 is selected from 0, 1, 2, 3;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted An aryl group with 6-40 carbon atoms, a substituted or unsubstituted heteroaryl group with 2-40 carbon atoms, and a substituted or unsubstituted arylamino group with 6-40 carbon atoms;
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are each independently selected from deuterium, cyano, halogen, and unsubstituted alkyl with 1-30 carbon atoms , Unsubstituted cycloalkyl with 3-30 carbon atoms, unsubstituted heterocycloalkyl with 2-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, unsubstituted Heteroaryl groups with 1-30 carbon atoms, unsubstituted alkoxy groups with 1-30 carbon atoms, unsubstituted arylamino groups with 6-30 carbon atoms, and unsubstituted carbon atoms are An alkylsilyl group of 1-30, an unsubstituted arylsilyl group of 6-30 carbon atoms.
  • R 1 and R 2 can be connected to form a ring
  • R 2 and R 3 can be connected to form a ring
  • R 3 and R 5 can be connected to form a ring
  • R 1 and R 4 can be connected to form a ring.
  • R 4 and R 5 can be connected to form a ring, wherein said ring is independently fused aromatic rings, fused heteroaryl rings, e.g. xanthene ring, a fluorene ring, a 9,10-dihydro-10-phenyl Acridine ring etc., for example, in the compound Among them, R 3 and R 5 form a 10-phenyl-9,10-dihydroacridine ring.
  • a and B "capable of being connected to form a ring” includes that A and B are independent of each other and not connected; it also includes that A and B are connected to form a ring.
  • R 1 and R 2 can be connected to form a ring, including the way that R 1 and R 2 are independent of each other and not connected, and R 1 and R 2 can be connected to each other to form a ring;
  • R 2 and R 3 can be connected to form a ring, including R 2 and R 3 are independent of each other and not connected, including the way that R 2 and R 3 are connected to each other to form a ring;
  • R 3 and R 5 can be connected to form a ring, including the way that R 3 and R 5 are independent of each other and are not connected, also including R 3 and R 5 are connected to each other to form a ring;
  • R 1 and R 4 can be connected to form a ring, including the way that R 1 and R 4 are independent of each other and are not connected, and R 1 and R 4 are connected to form
  • the ring formed by the connection of R 1 and R 2 may be saturated, such as cyclopentane, cyclohexane; or unsaturated, the ring formed by the connection of R 2 and R 3 , and the ring formed by the connection of R 1 and R 4,
  • the ring formed by the connection of R 4 and R 5 and the ring formed by the connection of R 3 and R 5 have the same meaning as the ring formed by the connection of R 1 and R 2.
  • the ring is a saturated or unsaturated 3 to 7 membered ring.
  • the non-positioned link in this application refers to the single bond extending 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 phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which means The meaning of includes any possible connection mode as shown in formula (X'-1) ⁇ 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, for example, 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.
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from deuterium, cyano, fluorine, and the number of unsubstituted carbon atoms is 1. -5 alkyl group, substituted or unsubstituted aryl group having 6-20 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, substituted or unsubstituted carbon number 10- 20 arylamine group.
  • the substituents on R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from deuterium, cyano, fluorine, and the number of carbon atoms is 1-5 alkyl groups, substituted or unsubstituted aryl groups with 6-20 carbon atoms, unsubstituted heteroaryl groups with 3-20 carbon atoms, unsubstituted aryl groups with 12-20 carbon atoms Amine group.
  • R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from deuterium, cyano, fluorine, and carbon atoms.
  • the substituents on R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from deuterium, cyano, fluorine, and methyl.
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from deuterium, cyano, halogen, and the number of carbon atoms is 1-
  • M 1 is selected from a single bond or
  • b 1 , b 6 , b 7 , b 13 and b 16 are the same or different, and are independently 1, 2, 3, 4, 5;
  • b 2 , b 3 , b 4 , b 5 , b 8 , b 9 , b 11 , b 12 , b 14 , b 17 , b 18 and b 19 are the same or different, and are independently 1, 2, 3, 4;
  • b 10 is 1, 2, 3;
  • b 15 is 1, 2, 3, 4, 5, 6, 7;
  • X is selected from O, S, Si (E 20 E 21 ), C (E 22 E 23 ), N (E 24 ), Se;
  • Z 1 to Z 6 are the same or different, and are each independently selected from C(E') or N, and at least one of Z 1 to Z 6 is N, wherein E'in Z 1 to Z 6 is the same or Different and independently selected from hydrogen, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, heteroaryl with 3-18 carbon atoms, and rings with 3-10 carbon atoms Alkyl group, or adjacent E'can be connected to form a ring;
  • E 1 to E 25 are the same or different, and are independently selected from hydrogen, deuterium, halogen, cyano, alkyl with 1-10 carbon atoms, aryl with 6-18 carbon atoms, and the number of carbon atoms is 3-18 heteroaryl, 3-10 cycloalkyl, alkyl substituted aryl with 6-18 carbon atoms; or E 20 and E 21 can be connected to form a ring, or E 22 and E 23 can be connected to form a ring, or any two E 6 can be condensed with the phenyl connected to form an aromatic ring, or any two E 7 can be condensed with the phenyl connected to form an aromatic ring, wherein E 1 , E 13 , E 14 and E 19 are not aryl groups.
  • b 1 is the number of substituent E 1 , when b 1 is greater than or equal to 2, any two E 1 are the same or different;
  • b 2 is the number of substituent E 2 , when b 2 is greater than or equal to 2.
  • b 3 is the number of substituent E 3 , when b 3 is greater than or equal to 2, any two E 3 are the same or different;
  • b 4 is the number of substituent E 4, when When b 4 is greater than or equal to 2, any two E 4 are the same or different;
  • b 5 is the number of substituent E 5 , when b 5 is greater than or equal to 2, any two E 5 are the same or different;
  • b 6 is a substituent The number of E 6 , when b 6 is greater than or equal to 2, any two E 6 are the same or different;
  • b 7 is the number of substituent E 7 , when b 7 is greater than or equal to 2, any two E 7 are the same or different ;
  • B 8 is the number of substituent E
  • E 6 and E 7 can be condensed with the phenyl group connected to them to form an aromatic ring, for example , the benzene ring connected to E 6 and E 7 can be condensed to form a naphthyl group.
  • a and B "capable of being connected to form a ring" includes that A and B are independent of each other and not connected; it also includes that A and B are connected to form a ring.
  • E 20 and E 21 can be connected to form a ring, including E 20 and E 21 are independent of each other and not connected, and E 20 and E 21 can be connected to each other to form a ring;
  • E 22 and E 23 can be connected to form a ring, including E 22 and E 23 are independent of each other and not connected, including E 22 and E 23 are connected to each other to form a ring.
  • Z 3 and Z 4 can be connected to form a ring, including the way that E'of Z 3 and E'of Z 4 are independent of each other and not connected, and it also includes the connection of E'of Z 3 and E'and E'of Z 4
  • the atoms of are connected to form a ring, and the ring refers to a saturated or unsaturated ring.
  • the number of carbon atoms of the ring can be 5, for example It can also be 6, for example It can also be 13, for example
  • the number of carbon atoms in the ring can also be other values, which will not be listed here, and the application does not specifically limit the number of carbon atoms in the ring.
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from the group consisting of the following groups: deuterium, cyano, Fluorine, alkyl groups with 1-5 carbon atoms, substituted or unsubstituted aryl groups with 6-25 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-20 carbon atoms, substituted or unsubstituted
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from the group consisting of the following groups: deuterium, cyano, Fluorine, an alkyl group with 1-5 carbon atoms or substituted or unsubstituted W, the unsubstituted W is selected from the group consisting of the following groups:
  • the substituent of W is selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, dibenzofuran Group, dibenzothienyl, biphenyl, pyridyl, 9,9-dimethylfluorenyl, 9,9-dimethyl-9H-9-silylfluorenyl; when there are multiple substituents of W, Multiple substituents are the same or different.
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from the group consisting of the following groups: deuterium, cyano, Fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or the group consisting of the following groups:
  • the R 1 , R 2 , R 3 , R 4 and R 5 are the same or different, and are independently selected from the group consisting of the following groups: deuterium, cyano, Fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or the group consisting of the following groups:
  • the organic compound is selected from one or more of the following compounds P1-P200:
  • the second aspect of the application provides an application of the organic compound provided in the first aspect of the application in an organic electroluminescent device.
  • an organic compound can be used as an organic electroluminescent layer material of an organic electroluminescent device.
  • the third aspect of the present application provides an organic electroluminescent device, including an anode, a cathode, and at least one functional layer between the anode and the cathode.
  • the functional layer includes a hole injection layer, a hole transport layer, and The electroluminescence layer, the electron transport layer and the electron injection layer.
  • the organic electroluminescence layer contains the organic compound provided in the first aspect of the present application, and optionally, contains at least one of the compounds P1-P184.
  • the compound provided in the present application can be used to form at least one organic film layer in the functional layer 300 to improve the lifetime characteristics and efficiency characteristics of the organic electroluminescent device and reduce the driving voltage; in some embodiments, It can also improve the mass production stability of organic electroluminescent devices.
  • the functional layer 300 includes an organic electroluminescent layer 330
  • the organic electroluminescent layer 330 includes a compound provided in the present application.
  • the organic electroluminescent layer 330 may be composed of the compound provided in the present application, or may be composed of the compound provided in the present application and other materials.
  • an organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, an organic electroluminescence layer 330, and an electron The transport layer 340, the electron injection layer 350, and the cathode 200.
  • the compound provided in this application can be applied to the organic electroluminescent layer 330 of an organic electroluminescent device, and can effectively improve the electron transport characteristics of the organic electroluminescent device.
  • the hole characteristic means that the holes formed in the anode 100 are easily injected into the organic electroluminescent layer 330 and are transported in the organic electroluminescent layer 330 according to the conductivity characteristics of the HOMO level.
  • 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. It is preferable to include a transparent electrode containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the organic electroluminescent layer 330 may be composed of a single luminescent material, or may include a host material and a guest material.
  • the organic electroluminescent layer 330 is composed of a host material and a guest material. The holes injected into the organic electroluminescent layer 330 and the electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form an excitation. The exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
  • the guest material of the organic electroluminescent layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not described in this application. Special restrictions.
  • the guest material of the organic electroluminescent layer 330 may be Ir(piq) 2 (acac).
  • the guest material of the organic electroluminescent layer 330 may be BD-1, or may be a compound provided in the present disclosure.
  • the electron transport layer 340 may be a single-layer structure or a multilayer structure, and it may include one or more electron-transporting materials.
  • the electron-transporting materials may be selected from benzimidazole derivatives, oxadiazole derivatives, and quinoxalines. Derivatives or other electronic transmission materials, this application does not impose special restrictions on this.
  • the electron transport layer 340 may be composed of DBimiBphen and LiQ.
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode containing aluminum as a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of m-MTDATA.
  • the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer 321 is provided on the surface of the second hole transport layer 322 close to the anode 100;
  • a hole transport layer 321 or a second hole transport layer 322 includes the organic compound provided in the present disclosure.
  • either the first hole transport layer 321 or the second hole transport layer 322 may contain the organic compound provided in the present disclosure, or the first hole transport layer 321 and the second hole transport layer 322 may be both Contains the organic compounds provided in the present disclosure. It is understandable that the first hole transport layer 321 or the second hole transport layer 322 may also contain other materials, or may not contain other materials. It can be understood that, in another embodiment of the present disclosure, the second hole transport layer 322 may serve as an electron blocking layer of the organic electroluminescent device.
  • 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.
  • the organic electroluminescent device of the present application is based on the excellent performance of the organic compound of the present application, has good carrier conduction efficiency and lifetime, reduces the driving voltage of the organic electroluminescent device, and improves the light-emitting performance.
  • the compounds of the synthesis method not mentioned in this application are all raw material products obtained through commercial channels.
  • nBuLi(2.5M)(96.7mL, 241.8mmol) dropwise, keep the temperature constant during the dropping process, stir for 1h, add adamantanone (30g, 199.7mmol) in tetrahydrofuran THF (100mL) solution dropwise After the addition of the system, the temperature was naturally raised to room temperature, and methanesulfonic acid (46.5 g, 483.6 mmol) was added, and then heated and stirred to reflux for 1 h.
  • reaction solution was cooled to room temperature, deionized water was added to it and stirred for 0.5h, then ethyl acetate (200mL) was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the resulting crude product was used Ethyl acetate/ethanol (1:2) was recrystallized and purified to obtain a white solid intermediate IA-1 (43 g, yield 71%).
  • the Intermediate IA-3 (2.3g, 3.25mmol) was dissolved in a round-bottomed flask containing tert-butylbenzene (50mL), and then n-butyllithium (2.5M, 1.13mL) was added dropwise.
  • the mixture was heated to 200°C for 6h, the system was cooled to room temperature, the liquid nitrogen was cooled to -78°C, and boron tribromide (1M, 1.6mL) was slowly added dropwise.
  • the organic compound was prepared by the same method as in Synthesis Example 1, except that the raw material 1 in Table 1 was used instead of the diphenylamine in step (3) in Example 1.
  • the structure and characterization data of the final prepared organic compound are shown in Table 1.
  • the organic compound was prepared by the same method as in Example 9, except that the raw material 2 in Table 2 was used to replace the p-methylaniline in step (1) in Example 9, and the raw material 3 was used to replace 9-(4-bromo (Phenyl)-9H-carbazole was synthesized as an intermediate in Table 2.
  • the intermediates in Table 2 are used to replace the intermediates I-B in step (2) in Example 9, and the structure and characterization data of the organic compounds finally prepared are shown in Table 3.
  • the organics were prepared by the same method as in Example 18, except that the raw material 4 in Table 4 was used to replace the 9-fluorenone in step (1) in Example 18, and the raw material 5 was used to replace 2-bromo-N-benzene.
  • the intermediates in Table 4 were synthesized by aniline.
  • the intermediates in Table 4 were used to replace the intermediates I-K in step (1) in Example 18.
  • the structure and characterization data of the final compound are shown in Table 5.
  • the thickness of ITO is The TOP substrate (manufactured by Corning) was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness), and the photolithography process was used to prepare it into an experimental substrate with cathode lap area, anode and insulating layer patterns , using ultraviolet ozone and O 2 :N 2 plasma for surface treatment to increase the work function of the anode (experimental substrate) and 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 Hole injection layer (HIL), and vacuum evaporation of NPB on the hole injection layer to form a thickness of The first hole transport layer (HTL1).
  • HIL Hole injection layer
  • HTL1 The first hole transport layer
  • TCTA 4,4',4"-tris(carbazol-9-yl)triphenylamine
  • ⁇ , ⁇ -ADN is used as the main body, and the organic compound P1 prepared in Synthesis Example 1 is simultaneously doped.
  • the main body and the dopant are formed with a thickness of 30:3 according to the film thickness ratio of 30:3.
  • DBimiBphen(4,7-Diphenyl-2,9-bis(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-1,10-phenanthroline) and LiQ(8-hydroxyquinoline) -Lithium) is mixed and evaporated in a weight ratio of 1:1 to form Thick electron transport layer (ETL), the metal Yb is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9, and then vacuum evaporated on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • 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 organic electroluminescent device was prepared by the same method as the device example 1, except that the compound listed in Table 8 except for the compound AE was used in turn to replace the organic compound P1 in the device example 1 to prepare the organic electroluminescent device.
  • Light emitting device
  • the organic electroluminescent device was prepared by the same method as the device embodiment 1, except that the compounds A-E listed below replace the organic compound 1 in the device embodiment 1 to prepare the organic electroluminescent device.
  • the organic electroluminescent devices prepared by the device examples and the preparation comparative examples were tested for the IVL (current-voltage-brightness) performance of the device under the condition of 10 mA/cm 2 and the lifetime of the T95 device under the condition of 15 mA/cm 2.
  • the test structure of the above test is shown in Table 8.
  • the performance of the organic electroluminescent devices of device examples 1-21 is greatly improved, which is mainly manifested in that the working voltage of the device is reduced by at least 8.0% , The luminous efficiency is increased by at least 8.8%, and the life span is increased by at least 11.03%.
  • the organic compound of the present application has an adamantane-six-membered ring structure, which can increase the electron density of the conjugated system of the entire organic compound and increase the hole conduction efficiency of the organic compound, thereby increasing the organic electrophoresis Carrier conduction efficiency and lifetime of light-emitting devices and photoelectric conversion devices.
  • the combination of a compound formed by an adamantane-six-membered ring and a solid ring centered on the boron element can greatly increase the stability of the carriers and improve the light-emitting performance of the organic light-emitting device.

Landscapes

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

Abstract

本申请提供了一种有机化合物，该化合物具有如下式(1)所示的结构。其中，Q 1、Q 2和Q 3中的至少一者为（aa），（bb）表示连接键；n 1和n 2相同或者不同，且分别独立地选自0、1、2、3、4；n 3和n 4相同或者不同，且分别独立地选自0、1、2、3、4、5；n 5选自0、1、2、3；R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基。本申请的有机化合物用于有机电致发光器件，可以显著提升发光效率并延长有机电致发光器件的寿命。

Description

一种有机化合物、其应用以及有机电致发光器件
相关申请的交叉引用
本申请要求于2019年12月31日递交的申请号为CN201911416572.7的中国专利申请的优先权，以及于2020年10月21日递交的申请号为CN202011133615.3的中国专利申请的优先权，在此引用上述中国专利申请公开的内容全文以作为本申请的一部分。
技术领域
本申请涉及有机发光材料技术领域，具体地，涉及一种有机化合物、其应用以及有机电致发光器件。
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膜层或者无机膜层组成，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、作为能量转化层的电致发光层、电子传输层和阴极。当在阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。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。
发明内容
本申请的目的是提高电致发光器件的发光效率延长其使用寿命。
为了实现上述目的，本申请第一方面提供一种该化合物具有如下式(1)所示的结构：
Figure PCTCN2020131873-appb-000001
其中，Q 1、Q 2和Q 3中的至少一者为
Figure PCTCN2020131873-appb-000002
表示连接键；
n 1和n 2相同或者不同，且分别独立地选自0、1、2、3、4；
n 3和n 4相同或者不同，且分别独立地选自0、1、2、3、4、5；
n 5选自0、1、2、3；
R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基；
或者相邻的两个R 1与R 2相互连接形成环，或者相邻的两个R 2与R 3相互连接形成环，或者相邻的两个R 3与R 4相互连接形成环，或者相邻的两个R 4与R 5相互连接形成环，或者相邻的两个R 1与R 4相互连接形成环；
所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘，氰基，卤素，未取代的碳原子数为1-30的烷基，未取代的碳原子数为3-30的环烷基，未取代的碳原子数为2-30的杂环烷基，任选地被碳原子数为1-5的烷基取代的碳原子数为6-30的芳基，未取代的碳原子数为1-30的杂芳基，未取代的碳原子数为1-30的烷氧基，未取代的碳原子数为6-30的芳胺基，未取代的碳原子数为1-30的烷基甲硅烷基，未取代的碳原子数为6-30的芳基甲硅烷基。
本申请第二方面提供一种本申请第一方面提供的有机化合物在有机电致发光器件中的应用。
本申请第三方面提供一种有机电致发光器件，包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，所述功能层包括空穴注入层、空穴传输层、有机电致发光层、电子传输层以及电子注入层，所述有机电致发光层含有本申请第一方面提供的有机化合物。
通过上述技术方案，本申请的有机化合物具有金刚烷-六元环基结构，将其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。且可以降低含有本申请的有机化合物的有机电致发光器件的驱动电压，提高光电转化器件开路电压。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
通过参照附图详细描述其示例实施方式，本申请的上述和其它特征及优点将变得更加明显。
图1是本申请实施方式的一种有机电致发光器件的结构示意图。
图2是本申请实施方式的一种电子装置的结构示意图。
图中主要元件附图标记说明如下：
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、有机电致发光层；340、电子传输层；350、电子注入层；400、电子装置。
具体实施方式
现在将参考附图更全面地描述示例实施例。然而，示例实施例能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施例使得本申请将更加全面和完整，并将示例实施例的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。
在图中，为了清晰，可能夸大了区域和层的厚度。在图中相同的附图标记表示相同或类似的结构，因而将省略它们的详细描述。
所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多个实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。然而，本领域技术人员将意识到，可 以实践本申请的技术方案而没有所述特定细节中的一个或更多个，或者可以采用其它的方法、组元、材料等。在其它情况下，不详细示出或描述公知结构、材料或者操作以避免模糊本申请的主要技术创意。
用语“该”和“所述”用以表示存在一个或多个要素/组成部分/等；用语“包括”和“具有”用以表示开放式的包括在内的意思并且是指除了列出的要素/组成部分/等之外还可存在另外的要素/组成部分/等。
本申请第一方面提供一种有机化合物，该化合物具有如下式(1)所示的结构：
Figure PCTCN2020131873-appb-000003
其中，Q 1、Q 2和Q 3中的至少一者为
Figure PCTCN2020131873-appb-000004
表示连接键；
n 1和n 2相同或者不同，且分别独立地选自0、1、2、3、4；
n 3和n 4相同或者不同，且分别独立地选自0、1、2、3、4、5；
n 5选自0、1、2、3；
R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基，
或者相邻的两个R 1与R 2相互连接形成环，或者相邻的两个R 2与R 3相互连接形成环，或者相邻的两个R 3与R 4相互连接形成环，或者相邻的两个R 4与R 5相互连接形成环，或者相邻的两个R 1与R 4相互连接形成环，需要说明的是，“任意两个相邻的R 1与R 2相互连接形成环”可以以形成饱和或不饱和的环状形式存在，也可以是相互独立地存在。举例而言，当相邻的两个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成环时，成环方式例如
Figure PCTCN2020131873-appb-000005
Figure PCTCN2020131873-appb-000006
所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘，氰基，卤素，未取代的碳原子数为1-30的烷基，未取代的碳原子数为3-30的环烷基，未取代的碳原子数为2-30的杂环烷基，任选地被碳原子数为1-5的烷基取代的碳原子数为6-30的芳基，未取代的碳原子数为1-30的杂芳基，未取代的碳原子数为1-30的烷氧基，未取代的碳原子数为6-30的芳胺基，未取代的碳原子 数为1-30的烷基甲硅烷基，未取代的碳原子数为6-30的芳基甲硅烷基，本申请中“任选地被碳原子数为1-5的烷基取代的碳原子数为6-30的芳基”是指芳基可以被碳原子数为1-5的烷基取代，也可以不被碳原子数为1-5的烷基取代。
在本申请中，“Q 1、Q 2和Q 3中的至少一者为
Figure PCTCN2020131873-appb-000007
”是指Q 1、Q 2和Q 3中的一个为
Figure PCTCN2020131873-appb-000008
或者Q 1、Q 2和Q 3中的两个为
Figure PCTCN2020131873-appb-000009
或者Q 1、Q 2和Q 3中的三个为
Figure PCTCN2020131873-appb-000010
在本申请中，式(1)中的虚线“------”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，Q 3处的虚线表示Q 3可以在此虚线处形成连接键与苯环连接而成环，也可以不形成连接键，不与苯环连接而成环；Q 2处的虚线表示Q 2可以在此虚线处形成连接键与苯环连接而成环，也可以不形成连接键，不与苯环连接而成环；Q 1处的虚线表示Q 1可以在此虚线处形成连接键与苯环连接而成环，也可以不形成连接键，不与苯环连接而成环。
在本申请中，n 1、n 2、n 3、n 4、n 5选自0时，苯环没有被取代。
在本申请中，n 1为取代基R 1的数量，当n 1大于或等于2时，任意两个R 1相同或不同；n 2为取代基R 2的数量，当n 2大于或等于2时，任意两个R 2相同或不同；n 3为取代基R 3的数量，当n 3大于或等于2时，任意两个R 3相同或不同；n 4为取代基R 4的数量，当n 4大于或等于2时，任意两个R 4相同或不同；n 5为取代基R 5的数量，当n 5大于或等于2时，任意两个R 5相同或不同。
本申请的有机化合物的分子结构中，有机化合物中硼元素与中心芳基胺形成实心环结构。将硼基胺与富电子的螺芳基胺结合后，可以提高电子稳定性，防止激子消失，有利于主体的能量转移，从而使效率最大化。将金刚烷-六元环与以硼元素为核心的实心环链接，由于金刚烷的烷烃结构，可以大大降低分子的Π-Π堆叠效应，显著提高载流子的稳定性，进而改善有机发光器件的发光性能。含有该有机化合物的有机电致发光器件具有较高的发光效率和较长的使用寿命。
在本申请中，R 1、R 2、R 3、R 4和R 5的碳原子数，指的是所有碳原子数。举例而言，若R 1、R 2、R 3、R 4和R 5选自取代的碳原子数为18的芳基，则芳基及其上的取代基的所有碳原子数为18；若R 1、R 2、R 3、R 4和R 5选自取代的碳原子数为10的烷基，则烷基及其上的取代基的所有碳原子数为10；若R 1、R 2、R 3、R 4和R 5选自取代的碳原子数为10的杂芳基，则杂芳基及其上的取代基的所有碳原子数为10；若R 1、R 2、R 3、R 4和R 5选自取代的碳原子数为10的芳胺基，则芳胺基及其上的取代基的所有碳原子数为10。
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 PCTCN2020131873-appb-000011
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可以彼此相同或不同，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18～30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，表述“任意两个相邻的取代基形成环”中，“任意相邻”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环(例如，3～18元的饱和或不饱和环)；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环，例如萘环、菲环、蒽环。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、O、N、P、Si、Se或S等杂原子且其余原子为碳和氢。未取代的烷基可以是没有任何双键或三键的“饱和烷基基团”。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至20个碳原子，在本申请中，诸如“1至20”的数值范围是指给定范围中的各个整数；例如，“1至20个碳原子”是指可包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的烷基。烷基还可为具有1至10个碳原子的中等大小烷基。烷基还可为具有1至6个碳原子的低级烷基。此外，烷基可为取代的或未取代的。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、正己基、正庚基、正辛基、2-乙基己基、壬基、癸基等。
在本申请中，芳基指的是衍生自芳香烃环的任选官能团或取代基。芳基可以是单环芳基或多环芳基，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多个稠环芳基。即，通过碳碳键共轭连接的两个或者多个芳香基团也可以视为本申请的芳基。其中，芳基中不含有B、O、N、P、Si、Se或S等杂原子。举例而言，在本申请中，苯基、联苯基等为芳基。芳基的示例可以包括苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、六联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2020131873-appb-000012
基、芴基等，而不限于此。
在本申请中，取代的芳基，指的是芳基中的一个或者多个氢原子被其它基团所取代。例如至少一个氢原子被氘原子、F、Cl、Br、I、CN、羟基、氨基、支链烷基、直链烷基、环烷基、烷氧基、烷胺基、芳基、杂芳基或者其他基团取代。可以理解的是，取代的碳原子数为18的芳基，指的是芳基和芳基上的取代基的碳原子总数为18个。举例而言，9,9-二甲基芴基的碳原子数为15。
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、菲基、蒽基、1,10-菲罗啉基等。
在本申请中，杂芳基可以是包括B、O、N、P、Si、Se和S中的至少一个作为杂原子的杂芳基。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、N-芳基咔唑基、N-杂芳基咔唑基、N-烷基咔唑基、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、二苯并甲硅烷基、二苯并呋喃基、苯基取代的二苯并呋喃基、二苯并呋喃基取代的苯基等，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的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基、苯基取代的二苯并呋喃基、二苯并呋喃基取代的苯基等为通过碳碳键共轭连接的多个芳香环体系的杂芳基。在本申请中，杂芳基可以为咔唑基、二苯并呋喃基等。
在本申请中，作为取代基的杂芳基例如但不限于吡啶基、咔唑基、嘧啶基、哒嗪基、三嗪基、喹啉基、异喹啉基、喹唑啉基、吡嗪基、二苯并噻吩基、二苯并呋喃基、9,9-二甲基-9H-9-硅芴等。
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、N-甲基苯胺基、、二甲苯胺基、N-对甲苯二胺基和N-间甲苯二胺基等。在本申请中，芳胺基可以选自二苯胺基、二萘基胺基。
在本申请的一种具体实施方式中，该化合物具有如下式(1)所示的结构：
Figure PCTCN2020131873-appb-000013
其中，Q 1、Q 2和Q 3中的至少一者为
Figure PCTCN2020131873-appb-000014
表示连接键；
n 1和n 2相同或者不同，且分别独立地为0、1、2、3、4；
n 3和n 4相同或者不同，且分别独立地为0、1、2、3、4、5；
n 5选自0、1、2、3；
R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基；
所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘、氰基、卤素、未取代的碳原子数为1-30的烷基、未取代的碳原子数为3-30的环烷基、未取代的碳原子数为2-30的杂环 烷基、取代或未取代的碳原子数为6-30的芳基、未取代的碳原子数为1-30的杂芳基、未取代的碳原子数为1-30的烷氧基、未取代的碳原子数为6-30的芳胺基、未取代的碳原子数为1-30的烷基甲硅烷基、未取代的碳原子数为6-30的芳基甲硅烷基。
在本申请的一种具体实施方式中，R 1与R 2能够连接成环，R 2与R 3能够连接成环，R 3与R 5能够连接成环，R 1与R 4能够连接成环，R 4与R 5能够连接成环，其中，所述环独立地为稠合芳环、稠合杂芳环，例如 氧杂蒽环、芴环、10-苯基-9,10-二氢吖啶环等，举例而言，在化合物
Figure PCTCN2020131873-appb-000015
中，R 3与R 5形成10-苯基-9,10-二氢吖啶环。
在本申请中，A与B“能够连接成环”的含义包括A与B相互独立，不连接；也包括A与B相互连接成环。例如，R 1与R 2能够连接成环，包括R 1与R 2相互独立，不连接的方式，也包括R 1与R 2相互连接成环；R 2与R 3能够连接成环，包括R 2与R 3相互独立，不连接的方式，也包括R 2与R 3相互连接成环；R 3与R 5能够连接成环，包括R 3与R 5相互独立，不连接的方式，也包括R 3与R 5相互连接成环；R 1与R 4能够连接成环，包括R 1与R 4相互独立，不连接的方式，也包括R 1与R 4相互连接成环；R 4与R 5能够连接成环，包括R 4与R 5相互独立，不连接的方式，也包括R 4与R 5相互连接成环。
进一步地，R 1与R 2连接形成的环可以是饱和的，例如环戊烷，环己烷；也可以是不饱和的，R 2与R 3连接形成的环、R 1与R 4连接形成的环、R 4与R 5连接形成的环和R 3与R 5连接形成的环与R 1与R 2连接形成的环的意义相类似。
可选地，该环为饱和或不饱和的3至7元环。
本申请中的不定位连接键，是指从环体系中伸出的单键
Figure PCTCN2020131873-appb-000016
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，下式(f)中所示的，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 PCTCN2020131873-appb-000017
再举例而言，下式(X＇)中所示的，式(X＇)所表示的菲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 PCTCN2020131873-appb-000018
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 PCTCN2020131873-appb-000019
在本申请中，卤素基团例如可以为氟、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，R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、氟、未取代的碳原子数为1-5的烷基、取代或未取代的碳原子数为6-20的芳基、取代或未取代的碳原子数为3-30的杂芳基、取代或未取代的碳原子数为10-20的芳胺基。
在本申请的一种具体实施方式中，R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘、氰基、氟、碳原子数为1-5的烷基、取代或未取代的碳原子数为6-20的芳基、未取代的碳原子数为3-20的杂芳基、未取代的碳原子数为12-20的芳胺基。
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘，氰基，氟，碳原子数为1-5的烷基，任选地被甲基、乙基、异丙基、叔丁基取代的碳原子数为6-15的芳基，碳原子数为5-12的杂芳基。
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘、氰基、氟、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并噻吩基、9,9-二甲基-9H-9-硅芴基、二苯并呋喃基、9,9-二甲基芴基、咔唑基、叔丁基取代的苯基。
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、碳原子数为1-10的烷基或者如下基团所组成的组：
Figure PCTCN2020131873-appb-000020
Figure PCTCN2020131873-appb-000021
其中，
Figure PCTCN2020131873-appb-000022
表示化学键，
M 1选自单键或者
Figure PCTCN2020131873-appb-000023
b 1、b 6、b 7、b 13和b 16相同或不同，且分别独立地为1、2、3、4、5；
b 2、b 3、b 4、b 5、b 8、b 9、b 11、b 12、b 14、b 17、b 18和b 19相同或不同，且分别独立地为1、2、3、4；
b 10为1、2、3；
b 15为1、2、3、4、5、6、7；
X选自O、S、Si(E 20E 21)、C(E 22E 23)、N(E 24)、Se；
Y选自O、S、N(E 25)；
Z 1至Z 6相同或不同，且各自独立地选自C(E’)或N，且Z 1至Z 6中至少一个为N，其中，所述Z 1至Z 6中的E’相同或不同，且分别独立地选自氢、碳原子数为1-10烷基、碳原子数为6-18芳基、碳原子数为3-18的杂芳基、碳原子数3-10的环烷基，或者相邻的E’能够连接成环；
E 1至E 25相同或不同，且分别独立地选自氢、氘、卤素、氰基、碳原子数为1-10的烷基、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3-10的环烷基、烷基取代的碳原子数为6-18的芳基；或者E 20和E 21能够连接成环，或者E 22和E 23能够连接成环，或者任意两个E 6能够和与之连接的苯基稠合形成芳环，或者任意两个E 7能够和与之连接的苯基稠合形成芳环，其中E 1、E 13、E 14和E 19不为芳基。
在本申请中，b 1为取代基E 1的数量，当b 1大于或等于2时，任意两个E 1相同或不同；b 2为取代基E 2的数量，当b 2大于或等于2时，任意两个E 2相同或不同；b 3为取代基E 3的数量，当b 3大于或等于2时，任意两个E 3相同或不同；b 4为取代基E 4的数量，当b 4大于或等于2时，任意两个E 4相同或不同；b 5为取代基E 5的数量，当b 5大于或等于2时，任意两个E 5相同或不同；b 6为取代基E 6的数量，当b 6大于或等于2时，任意两个E 6相同或不同；b 7为取代基E 7的数量，当b 7大于或等于2时，任意两个E 7相同或不同；b 8为取代基E 8的数量，当b 8大于或等于2时，任意两个E 8相同或不同；b 9为取代基E 9的数量，当b 9大于或等于2时，任意两个E 9相同或不同；b 10为取代基E 10的数量，当b 10大于或等于2时，任意两个E 10相同或不同；b 11为取代基E 11的数量，当b 11大于或等于2时，任意两个E 11相同或不同；b 12为取代基E 12的数量，当b 12大于或等于2时，任意两个E 12相同或不同；b 13为取代基E 13的数量，当b 13大于或等于2时，任意两个E 13相同或不同；b 14为取代基E 14的数量， 当b 14大于或等于2时，任意两个E 14相同或不同；b 15为取代基E 15的数量，当b 15大于或等于2时，任意两个E 15相同或不同；b 16为取代基E 16的数量，当b 16大于或等于2时，任意两个E 16相同或不同；b 17为取代基E 17的数量，当b 17大于或等于2时，任意两个E 17相同或不同；b 18为取代基E 18的数量，当b 18大于或等于2时，任意两个E 18相同或不同；b 19为取代基E 19的数量，当b 19大于或等于2时，任意两个E 19相同或不同。
在本申请中，b 1至b 19选自0时，苯环没有被取代。
可选地，E 6和E 7能够和与之连接的苯基稠合形成芳环，例如E 6和E 7与之连接的苯环稠合形成萘基。
相邻的E’能够连接成环，是指Z 1和Z 2成环，或Z 2和Z 3成环，或Z 3和Z 4成环，或Z 4和Z 5成环，或Z 5和Z 6成环，Z 6和Z 1成环，当然也包括Z 2和Z 3成环且Z 5和Z 6成环等情况。
在本申请中，A与B“能够连接成环”的含义包括A与B相互独立，不连接；也包括A与B相互连接成环。例如，E 20和E 21能够连接成环，包括E 20和E 21相互独立，不连接的方式，也包括E 20和E 21相互连接成环；E 22和E 23能够连接成环，包括E 22和E 23相互独立，不连接的方式，也包括E 22和E 23相互连接成环。
例如，Z 3和Z 4能够连接成环，包括Z 3的E’与Z 4的E’相互独立，不连接的方式，也包括Z 3的E’与Z 4的E’以及E’所连接的原子连接成环，所述的环指的是饱和或不饱和的环，可选地，该环的碳原子数可以是5，例如
Figure PCTCN2020131873-appb-000024
也可以是6，例如
Figure PCTCN2020131873-appb-000025
还可以是13，例如
Figure PCTCN2020131873-appb-000026
当然，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，且分别独立地选自如下基团所组成的组：氘、氰基、氟、碳原子数为1-5的烷基、取代或未取代的碳原子数为6-25的芳基、取代或未取代的碳原子数为3-20的杂芳基、取代或未取代的碳原子数为12-20的芳胺基，其中碳原子数为6-25的芳基中芳基的碳原子数可以是选自6、8、10、12、14、16、18、20、25，碳原子数为3-20的杂芳基中杂芳基的碳原子数可以选自3、4、5、9、12、18、20。
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、碳原子数为1-5的烷基、取代或未取代的碳原子数为6-10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12-15的芳胺基。
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、碳原子数为1-5的烷基或者取代或未取代的W，所述未取代的W选自如下基团组成的组：
Figure PCTCN2020131873-appb-000027
Figure PCTCN2020131873-appb-000028
所述W基团被取代时，W的取代基选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、二苯并呋喃基、二苯并噻吩基、联苯基、吡啶基、9,9-二甲基芴基、9,9-二甲基-9H-9-硅芴基；W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，且分别独立地选自如下基团所组成的组：氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或如下基团所组成的组：
Figure PCTCN2020131873-appb-000029
在本申请的一种具体实施方式中，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或如下基团所组成的组：
Figure PCTCN2020131873-appb-000030
Figure PCTCN2020131873-appb-000031
在本申请的一种具体实施方式中，该有机化合物选自以下化合物P1-P200中的一种或几种：
Figure PCTCN2020131873-appb-000032
Figure PCTCN2020131873-appb-000033
Figure PCTCN2020131873-appb-000034
Figure PCTCN2020131873-appb-000035
Figure PCTCN2020131873-appb-000036
Figure PCTCN2020131873-appb-000037
Figure PCTCN2020131873-appb-000038
Figure PCTCN2020131873-appb-000039
Figure PCTCN2020131873-appb-000040
本申请第二方面提供一种本申请第一方面提供的有机化合物在有机电致发光器件中的应用。根据本申请，有机化合物可以用作有机电致发光器件的有机电致发光层材料。
本申请第三方面提供一种有机电致发光器件，包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，所述功能层包括空穴注入层、空穴传输层、有机电致发光层、电子传输层以及电子注入 层，有机电致发光层含有本申请第一方面提供的有机化合物，可选地，含有化合物P1-P184中的至少一种。
举例而言，如图1所示，有机电致发光器件包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的化合物。
可选地，本申请所提供的化合物可以用于形成功能层300中的至少一个有机膜层，以改善有机电致发光器件的寿命特性、效率特性并且降低驱动电压；在某些实施例中，还可以提高有机电致发光器件的量产稳定性。
可选地，功能层300包括有机电致发光层330，有机电致发光层330包含本申请所提供的化合物。其中，有机电致发光层330既可以为本申请所提供的化合物组成，也可以由本申请所提供的化合物和其他材料共同组成。
在本申请的一种实施方式中，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、空穴注入层310、空穴传输层320、有机电致发光层330、电子传输层340、电子注入层350和阴极200。本申请提供的化合物可以应用于有机电致发光器件的有机电致发光层330，可以有效改善有机电致发光器件的电子传输特性。其中，空穴特性是指在阳极100中形成的空穴容易地被注入有机电致发光层330、并且根据HOMO水平的传导特性而在有机电致发光层330中传输。
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。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，有机电致发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机电致发光层330由主体材料和客体材料组成，注入有机电致发光层330的空穴和注入有机电致发光层330的电子可以在有机电致发光层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客体材料，进而使得客体材料能够发光。
有机电致发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机电致发光层330的客体材料可以为Ir(piq) 2(acac)。在本申请的另一种实施方式中，有机电致发光层330的客体材料可以为BD-1，也可以由本公开所提供的化合物。
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苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，电子传输层340可以由DBimiBphen和LiQ组成。
可选地，阴极200包括以下阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括：金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca，但不限于此。优选包括包含铝的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层320之间还可以设置有空穴注入层310，以增强 向空穴传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，空穴注入层310可以由m-MTDATA组成。
可选的，空穴传输层320包括第一空穴传输层321和第二空穴传输层322，且第一空穴传输层321设于第二空穴传输层322靠近阳极100的表面；第一空穴传输层321或第二空穴传输层322包含本公开所提供的有机化合物。其中，既可以第一空穴传输层321或第二空穴传输层322中的一层包含本公开所提供的有机化合物，也可以第一空穴传输层321和第二空穴传输层322均含有本公开所提供的有机化合物。可以理解的是，第一空穴传输层321或第二空穴传输层322还可以含有其他材料，也可以不含有其他材料。可以理解的是，在本公开的另一种实施方式中，第二空穴传输层322可以作为有机电致发光器件的电子阻挡层。
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。在本申请的一种实施方式中，电子注入层350可以包括LiQ。
本申请的有机电致发光器件基于本申请有机化合物的优异性能，具有良好的载流子传导效率以及寿命，降低有机电致发光器件的驱动电压，改善发光性能。
下面通过实施例来进一步说明本申请，但是本申请并不因此而受到任何限制。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
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1(有机化合物P1)
中间体I-A-1的合成
Figure PCTCN2020131873-appb-000041
(1)将2-溴-N-苯基苯胺(50g，199.7mmol)在四氢呋喃THF(300mL)中溶清后置于氮气保护下干燥的圆底烧瓶中，液氮降温至体系-78℃，开始滴加nBuLi(2.5M)(96.7mL，241.8mmol)，滴加过程中保持温度不变，搅拌1h后将溶有金刚烷酮(30g，199.7mmol)的四氢呋喃THF(100mL)溶液滴加进体系，滴加完毕后自然升温至室温，加入甲磺酸(46.5g，483.6mmol)后加热搅拌回流1h。将反应液冷却至室温，向其中加入去离子水搅拌0.5h，之后加入乙酸乙酯(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/乙醇(1：2)进行重结晶提纯，得到白色固体中间体I-A-1(43g，收率71％)。
中间体I-A-3的合成
Figure PCTCN2020131873-appb-000042
(2)将中间体I-A-1(5.1g，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(0.08g，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，得到白色固体状中间体I-A-2(3.18g，收率42％)及黄色中间体I-A-3(2.3g，收率19％)。
中间体I-A-4的合成
Figure PCTCN2020131873-appb-000043
(3)氮气保护下，将中间体I-A-2(2.5g，5.64mmol)溶于盛有50mL甲苯的圆底烧瓶中，加入叔丁醇钠(1.18g，12.3mmol)，开启搅拌，升高体系温度至110℃，然后依次加入二苯胺(1.0g，6.11mmol)和四正丁基钛酸酯BTP(0.06g，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将，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，得到白色固体状中间体I-A-4(2.56g，产率78％)。
有机化合物P1的合成
Figure PCTCN2020131873-appb-000044
(4)氮气保护下，将中间体I-A-4(2.03g，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，得到固体状的有机化合物P1(0.87g，产率44.7％)，质谱：m/z＝553.3[M+H] +。
有机化合物P1的核磁数据
1H NMR(400MHz,CD 2Cl 2)：8.24(d,1H),7.98(dd,1H),7.72-7.56(m,6H),7.31(t,1H),7.11-6.97(m,5H),6.88-6.74(m,4H),6.68(dd,1H),2.35-2.13(m,8H),1.91(s,2H),1.73(d,2H),1.56(s,2H).
合成实施例2(有机化合物P12)
有机化合物P12的合成
Figure PCTCN2020131873-appb-000045
氮气保护下，将中间体I-A-3(2.3g，3.25mmol)溶于盛有叔丁基苯(50mL)的圆底烧瓶中，滴加正丁基锂(2.5M，1.13mL)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，得到固体状的有机化合物P12(1.37g，产率61.6％)质谱：m/z＝685.4[M+H] +。
合成实施例3-8
采用与合成实施例1相同的方法制备有机化合物，不同之处仅在于，用表1中的原料1代替实施例1中步骤(3)的二苯胺。最终制备得到的有机化合物的结构及表征数据见表1。
表1
Figure PCTCN2020131873-appb-000046
Figure PCTCN2020131873-appb-000047
合成实施例9(有机化合物P122)
中间体I-B的合成
Figure PCTCN2020131873-appb-000048
(1)将对甲基苯胺(4.1g，38.0mmol)、9-(4-溴苯基)-9H-咔唑(11.54g，35.8mmol)、三(二亚苄基丙酮)二钯(0.35g，0.38mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.36g，0.76mmol)以及叔丁醇钠(5.48g，57.0mmol)加入甲苯(80mL)中，氮气保护下加热至108℃，搅拌2h；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；使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯，得到淡黄色固体中间体I-B(11.5g，92％)。
中间体I-A-5的合成
Figure PCTCN2020131873-appb-000049
(2)氮气保护下，将中间体I-A-2(1.5g，3.33mmol，合成实施例1中制备的)溶于盛有100mL甲苯的圆底烧瓶中，加入叔丁醇钠(1.2g，12.7mmol)，开启搅拌，升高体系温度至150℃，然后依次加入中间体I-B(3.25g，9.33mmol)和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将，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，得到白色固体状中间体I-A-5(1.13g，产率44.7％)。
有机化合物P112的合成
Figure PCTCN2020131873-appb-000050
(3)氮气保护下，将中间体I-A-5(6.67g，8.8mmol)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，得到固体状的有机化合物P112(0.97g，产率15％)，质谱：m/z＝732.4[M+H] +。
合成实施例10-17
采用与实施例9相同的方法制备有机化合物，不同之处仅在于，用表2中的原料2代替实施例9中步骤(1)的对甲基苯胺，用原料3代替9-(4-溴苯基)-9H-咔唑合成表2中的中间体。用表2中的中间体代替实施例9中步骤(2)的中间体I-B，最终制备得到的有机化合物的结构及表征数据见表3。
表2
Figure PCTCN2020131873-appb-000051
Figure PCTCN2020131873-appb-000052
表3
Figure PCTCN2020131873-appb-000053
Figure PCTCN2020131873-appb-000054
合成实施例18(有机化合物P170)
中间体I-K的合成
Figure PCTCN2020131873-appb-000055
(1)在氮气下将2-溴-N-苯基苯胺(30g，120.9mmol)溶解在300mL的THF中后，液氮将体系降温至-78℃后向其中加入nBuLi(241.8mmol，96.7mL)。保温搅拌1h，将9-芴酮(21.8g，120.9mmol)缓慢滴加进体系，保温搅拌12小时后，将反应升至室温，加入甲磺酸(46.5g，483.6mmol)回流并 搅拌。反应1h后，将混合物用水淬灭，用乙酸乙酯萃取，用无水硫酸镁干燥，过滤并在减压下浓缩。试用乙酸乙酯和乙醇体系(1：3)对其进行重结晶提纯，得到固体中间体I-K(28.05g，产率70％)。
中间体I-K-1的合成
Figure PCTCN2020131873-appb-000056
(2)氮气保护下，将中间体I-A-2(8.2g，18.33mmol)溶于盛有100mL甲苯的圆底烧瓶中，加入叔丁醇钠(3.5g，36.7mmol)，开启搅拌，升高体系温度至150℃，然后依次加入中间体I-K(6.1g，18.33mmol)和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将，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，得到白色固体状中间体I-K-1(7.13g，产率52.5％)。
有机化合物P170的合成
Figure PCTCN2020131873-appb-000057
(3)氮气保护下，将中间体I-K-1(6.5g，8.8mmol)溶于盛有叔丁基苯(50mL)的圆底烧瓶中，滴加正丁基锂(2.5M，3.83mL)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，9.6mL)，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，得到固体状的有机化合物P170(2.08g，产率33％)。质谱：m/z＝715.72[M+H] +。
合成实施例19-20
采用与实施例18相同的方法制备有机物，不同之处仅在于，用表4中的原料4代替实施例18中步骤(1)的9-芴酮，用原料5代替2-溴-N-苯基苯胺合成表4中的中间体。用表4中的中间体代替实施例18中步骤(1)的中间体I-K。最终制备得到的化合物的结构及表征数据见表5。
表4
Figure PCTCN2020131873-appb-000058
Figure PCTCN2020131873-appb-000059
表5
Figure PCTCN2020131873-appb-000060
合成实施例21(有机化合物P182)
中间体II-1的合成
Figure PCTCN2020131873-appb-000061
(1)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)。而后将溶有间氯溴苯(36g，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；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到固体中间体II-1(24g，收率61％)。
中间体II-2的合成
Figure PCTCN2020131873-appb-000062
(2)将中间体II-1(10.74g，40.9mmol)、吡啶(6.2g，78mmol)和二氯甲烷(150mL)加入圆底烧瓶中，氮气保护下降温至-10℃，在-10℃～-5℃下缓慢滴加三氟甲磺酸酐(11.0g，39mmol)，保温搅拌3小时；而后向反应液中稀盐酸水洗至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II-2(14.6g，收率90.4％)。
中间体II-3的合成
Figure PCTCN2020131873-appb-000063
(3)将中间体II-2(12.3g，31.17mmol)、间氯苯硼酸(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II-3(7.5g，收率84.2％)。
中间体II-4的合成
Figure PCTCN2020131873-appb-000064
(4)将2,6-二溴-1-氯苯(6.9g，25.5mmol)、苯胺(2.4g，25.9mmol)、三(二亚苄基丙酮)二钯(0.23g，0.25mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.24g，0.50mmol)以及叔丁醇钠(3.67g，38.22mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌2h；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；使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯，得到淡黄色固体中间体II-4(3.2g，收率为42.6％)。
中间体II-5的合成
Figure PCTCN2020131873-appb-000065
(5)将中间体II-3(4.6g，12.77mmol)、中间体II-4(3.8g，12.77mmol)、三(二亚苄基丙酮)二钯(0.12g，0.13mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.10g，0.25mmol)以及叔丁醇钠(1.84g，19.17mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌1h；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，得到白色固体中间体II-5(4.35g，收率58.8％)。
化合物P182的合成
Figure PCTCN2020131873-appb-000066
(6)氮气保护下，将中间体II-5(5.1g，8.8mmol)溶于盛有叔丁基苯(50mL)的圆底烧瓶中，滴加正丁基锂(2.5M，3.83mL)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，9.6mL)，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，得到固体状的有机化合物P182(2.07g，产率42.6％)。质谱：m/z＝553.3[M+H] +。
器件实施例1
制备阳极：将ITO厚度为
Figure PCTCN2020131873-appb-000067
的TOP基板(康宁制造)切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极搭接区、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)的功函数的和清除浮渣。
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 PCTCN2020131873-appb-000068
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀NPB，以形成厚度为
Figure PCTCN2020131873-appb-000069
的第一空穴传输层(HTL1)。
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 PCTCN2020131873-appb-000070
的第二空穴传输层(HTL2)。
α,β-ADN作为主体，同时掺杂合成实施例1制备的有机化合物P1，主体和掺杂剂按照30：3的膜厚比形成了厚度为
Figure PCTCN2020131873-appb-000071
的有机电致发光层(EML)。
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的重量比进行混合并蒸镀形成了
Figure PCTCN2020131873-appb-000072
厚的电子传输层(ETL)，将金属Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2020131873-appb-000073
的电子注入层(EIL)，然后将镁(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 PCTCN2020131873-appb-000074
的阴极。
在上述阴极上蒸镀厚度为
Figure PCTCN2020131873-appb-000075
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。
其中，m-MTDATA、NPB、TCTA、α,β-ADN、DBimiBphen、CP-1和LiQ的结构式如下所示。
Figure PCTCN2020131873-appb-000076
Figure PCTCN2020131873-appb-000077
器件实施例2-21
采用与器件实施例1相同的方法制备有机电致发光器件，不同之处仅在于，依次用表8中列举的除化合物A-E以外的化合物替代器件实施例1中的有机化合物P1来制备有机电致发光器件。
器件对比例1-5
采用与器件实施例1相同的方法制备有机电致发光器件，不同之处仅在于，下面列举的化合物A-E替代器件实施例1中的有机化合物1来制备有机电致发光器件。
Figure PCTCN2020131873-appb-000078
测试例
将器件实施例和制备对比例制备得到的有机电致发光器件在10mA/cm 2的条件下测试器件的IVL(电流-电压-亮度)性能，在15mA/cm 2下测试T95器件寿命。上述测试的测试结构见表8。
表8
Figure PCTCN2020131873-appb-000079
Figure PCTCN2020131873-appb-000080
根据表8可知，相较于器件对比例1-5的有机电致发光器件，器件实施例1-21的有机电致发光器件性能得到大幅度改善，主要表现为器件工作电压至少降低了8.0％，发光效率至少提高了8.8％，寿命至少提高了11.03％。这是由于本申请的有机化合物中具有金刚烷-六元环基结构，该结构可以通过提升整个有机化合物的共轭体系的电子密度，并提高有机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。并且将金刚烷-六元环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。
以上详细描述了本发明的优选实施方式，但是，本发明并不限于上述实施方式中的具体细节，在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，这些简单变型均属于本发明的保护范围。
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，本发明对各种可能的组合方式不再另行说明。
此外，本发明的各种不同的实施方式之间也可以进行任意组合，只要其不违背本发明的思想，其同样应当视为本发明所公开的内容。

Claims (14)

  1. 一种有机化合物，其特征在于，所述有机化合物具有如下式(1)所示的结构：
    Figure PCTCN2020131873-appb-100001
    其中，Q 1、Q 2和Q 3中的至少一者为
    Figure PCTCN2020131873-appb-100002
    表示连接键；
    n 1和n 2相同或者不同，且分别独立地为0、1、2、3、4；
    n 3和n 4相同或者不同，且分别独立地为0、1、2、3、4、5；
    n 5选自0、1、2、3；
    R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基，
    或者相邻的两个R 1与R 2相互连接形成环，或者相邻的两个R 2与R 3相互连接形成环，或者相邻的两个R 3与R 4相互连接形成环，或者相邻的两个R 4与R 5相互连接形成环，或者相邻的两个R 1与R 4相互连接形成环；
    所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘，氰基，卤素，未取代的碳原子数为1-30的烷基，未取代的碳原子数为3-30的环烷基，未取代的碳原子数为2-30的杂环烷基，任选地被碳原子数为1-5的烷基取代的碳原子数为6-30的芳基，未取代的碳原子数为1-30的杂芳基，未取代的碳原子数为1-30的烷氧基，未取代的碳原子数为6-30的芳胺基，未取代的碳原子数为1-30的烷基甲硅烷基，未取代的碳原子数为6-30的芳基甲硅烷基。
  2. 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如下式(1)所示的结构：
    Figure PCTCN2020131873-appb-100003
    其中，Q 1、Q 2和Q 3中的至少一者为
    Figure PCTCN2020131873-appb-100004
    表示连接键；
    n 1和n 2相同或者不同，且分别独立地为0、1、2、3、4；
    n 3和n 4相同或者不同，且分别独立地为0、1、2、3、4、5；
    n 5选自0、1、2、3；
    R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、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6-40的芳基、取代或未取代的碳原子数为2-40的杂芳基、取代或未取代的碳原子数为6-40的芳胺基；
    所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘、氰基、卤素、未取代的碳原子数为1-30的烷基、未取代的碳原子数为3-30的环烷基、未取代的碳原子数为2-30的杂环烷基、取代或未取代的碳原子数为6-30的芳基、未取代的碳原子数为1-30的杂芳基、未取代的碳原子数为1-30的烷氧基、未取代的碳原子数为6-30的芳胺基、未取代的碳原子数为1-30的烷基甲硅烷基、未取代的碳原子数为6-30的芳基甲硅烷基。
  3. 根据权利要求1或2所述的有机化合物，其特征在于，R 1与R 2能够连接成环，R 2与R 3能够连接成环，R 3与R 5能够连接成环，R 1与R 4能够连接成环，R 4与R 5能够连接成环。
  4. 根据权利要求1～3中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘、氰基、氟、碳原子数为1-5的烷基、取代或未取代的碳原子数为6-20的芳基、未取代的碳原子数为3-20的杂芳基、未取代的碳原子数为12-20的芳胺基。
  5. 根据权利要求1～4中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5上的取代基相同或者不同，且分别独立地选自氘，氰基，氟，碳原子数为1-5的烷基，任选地被甲基、乙基、异丙基、叔丁基取代的碳原子数为6-15的芳基，碳原子数为5-12的杂芳基。
  6. 根据权利要求1～5中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自氘、氰基、卤素、碳原子数为1-10的烷基或者如下基团所组成的组：
    Figure PCTCN2020131873-appb-100005
    其中，
    Figure PCTCN2020131873-appb-100006
    表示化学键，
    M 1选自单键或者
    Figure PCTCN2020131873-appb-100007
    b 1、b 6、b 7、b 13和b 16相同或不同，且分别独立地为1、2、3、4、5；
    b 2、b 3、b 4、b 5、b 8、b 9、b 11、b 12、b 14、b 17、b 18和b 19相同或不同，且分别独立地为1、2、3、4；
    b 10为1、2、3；
    b 15为1、2、3、4、5、6、7；
    X选自O、S、Si(E 20E 21)、C(E 22E 23)、N(E 24)、Se；
    Y选自O、S、N(E 25)；
    Z 1至Z 6相同或不同，且各自独立地选自C(E’)或N，且Z 1至Z 6中至少一个为N，其中，所述Z 1至Z 6中的E’相同或不同，且分别独立地选自氢、碳原子数为1-10烷基、碳原子数为6-18芳基、碳原子数为3-18的杂芳基、碳原子数3-10的环烷基，或者相邻的E’能够连接成环；
    E 1至E 25相同或不同，且分别独立地选自氢、氘、卤素、氰基、碳原子数为1-10的烷基、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3-10的环烷基、烷基取代的碳原子数为6-18的芳基；或者E 20和E 21能够连接成环，或者E 22和E 23能够连接成环，或者任意两个E 6能够和与之连接的苯基稠合形成芳环，或者任意两个E 7能够和与之连接的苯基稠合形成芳环。
  7. 根据权利要求1～6中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、碳原子数为1-5的烷基、取代或未取代的碳原子数为6-25的芳基、取代或未取代的碳原子数为3-20的杂芳基、取代或未取代的碳原子数为12-20的芳胺基。
  8. 根据权利要求1～7中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、碳原子数为1-5的烷基，或者，取代或未取代的W，所述未取代的W选自如下基团组成的组：
    Figure PCTCN2020131873-appb-100008
    所述W基团被取代时，W的取代基选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基、萘基、咔唑基、二苯并呋喃基、二苯并噻吩基、联苯基、吡啶基、9,9-二甲基芴基、9,9-二甲基-9H-9-硅芴基；W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1～8中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或如下基团所组成的组：
    Figure PCTCN2020131873-appb-100009
  10. 根据权利要求1～9中任意一项所述的有机化合物，其特征在于，所述R 1、R 2、R 3、R 4和R 5相同或者不同，且分别独立地选自如下基团所组成的组：氘、氰基、氟、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或如下基团所组成的组：
    Figure PCTCN2020131873-appb-100010
    Figure PCTCN2020131873-appb-100011
  11. 根据权利要求1～10中任意一项所述的有机化合物，其特征在于，所述有机化合物选自以下化合物P1-P200中的一种或几种：
    Figure PCTCN2020131873-appb-100012
    Figure PCTCN2020131873-appb-100013
    Figure PCTCN2020131873-appb-100014
    Figure PCTCN2020131873-appb-100015
    Figure PCTCN2020131873-appb-100016
    Figure PCTCN2020131873-appb-100017
    Figure PCTCN2020131873-appb-100018
    Figure PCTCN2020131873-appb-100019
    Figure PCTCN2020131873-appb-100020
  12. 权利要求1～11中任一项所述的有机化合物在有机电致发光器件中的应用。
  13. 根据权利要求12所述的应用，其特征在于，所述有机化合物用作所述有机电致发光器件的有机电致发光层材料。
  14. 一种有机电致发光器件，包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，所述功能层包括空穴注入层、空穴传输层、有机电致发光层、电子传输层以及电子注入层，其特征在于，所述有机电致发光层的掺杂剂含有权利要求1～11中任一项所述的有机化合物。
PCT/CN2020/131873 2019-12-31 2020-11-26 一种有机化合物、其应用以及有机电致发光器件 WO2021135750A1 (zh)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1020217043405A KR102631942B1 (ko) 2019-12-31 2020-11-26 유기 화합물과 그 용도 및 유기 전계 발광 소자
US17/623,319 US20220306655A1 (en) 2019-12-31 2020-11-26 Organic compound, application thereof, and organic electroluminescent device

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201911416572 2019-12-31
CN201911416572.7 2019-12-31
CN202011133615.3 2020-10-21
CN202011133615.3A CN112028918B (zh) 2019-12-31 2020-10-21 一种有机化合物、其应用以及有机电致发光器件

Publications (1)

Publication Number Publication Date
WO2021135750A1 true WO2021135750A1 (zh) 2021-07-08

Family

ID=73573326

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2020/131873 WO2021135750A1 (zh) 2019-12-31 2020-11-26 一种有机化合物、其应用以及有机电致发光器件

Country Status (4)

Country Link
US (1) US20220306655A1 (zh)
KR (1) KR102631942B1 (zh)
CN (1) CN112028918B (zh)
WO (1) WO2021135750A1 (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102213030B1 (ko) * 2018-11-19 2021-02-08 에스에프씨주식회사 신규한 보론 화합물 및 이를 포함하는 유기발광소자
CN115298188A (zh) * 2020-03-18 2022-11-04 九州有机光材股份有限公司 化合物、发光材料及有机发光装置
KR20210137594A (ko) * 2020-05-07 2021-11-18 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 발광 소자
CN113045595A (zh) * 2021-02-05 2021-06-29 吉林奥来德光电材料股份有限公司 多环芳族系化合物、其制备方法、发光材料、发光层和有机电致发光器件
WO2024012365A1 (zh) * 2022-07-14 2024-01-18 清华大学 一种有机化合物及其应用
KR20240049743A (ko) * 2022-10-07 2024-04-17 삼성디스플레이 주식회사 축합환 화합물을 포함한 발광 소자, 상기 발광 소자를 포함한 전자 장치, 전자 기기, 및 상기 축합환 화합물

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105308026A (zh) * 2013-07-09 2016-02-03 东曹株式会社 具有金刚烷基的环状吖嗪化合物、制造方法、以及以该化合物作为构成成分的有机电致发光元件
CN106467553A (zh) * 2016-07-29 2017-03-01 江苏三月光电科技有限公司 一种含硼有机电致发光化合物及其在oled器件上的应用
WO2017195669A1 (ja) * 2016-05-13 2017-11-16 コニカミノルタ株式会社 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、表示装置及び照明装置
WO2018150832A1 (ja) * 2017-02-16 2018-08-23 学校法人関西学院 有機電界発光素子
WO2018186396A1 (ja) * 2017-04-03 2018-10-11 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
WO2019004247A1 (ja) * 2017-06-30 2019-01-03 住友化学株式会社 発光素子及びその製造に有用な高分子化合物
CN109575059A (zh) * 2018-12-19 2019-04-05 武汉华星光电半导体显示技术有限公司 热活化延迟荧光材料、其制备方法和电致发光器件
CN110028459A (zh) * 2019-05-24 2019-07-19 上海天马有机发光显示技术有限公司 化合物、显示面板以及显示装置
WO2019162332A1 (en) * 2018-02-20 2019-08-29 Cynora Gmbh Organic molecules for optoelectronic devices
US20190280209A1 (en) * 2018-03-08 2019-09-12 Jnc Corporation Organic electroluminescent element
WO2019194298A1 (ja) * 2018-04-05 2019-10-10 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101876763B1 (ko) * 2017-05-22 2018-07-11 머티어리얼사이언스 주식회사 유기화합물 및 이를 포함하는 유기전계발광소자
JP7276750B2 (ja) * 2017-10-13 2023-05-18 学校法人関西学院 多環芳香族系二量体化合物
WO2019198699A1 (ja) * 2018-04-12 2019-10-17 学校法人関西学院 シクロアルキル置換多環芳香族化合物
CN109438350B (zh) * 2018-11-19 2020-08-04 深圳市华星光电技术有限公司 有机小分子发光材料及有机电致发光器件
CN109593042B (zh) * 2018-12-24 2021-12-07 陕西莱特迈思光电材料有限公司 一种有机电致发光材料及包含其的有机电致发光器件
CN110156756A (zh) * 2019-05-27 2019-08-23 上海天马有机发光显示技术有限公司 化合物、显示面板以及显示装置
CN110128279A (zh) * 2019-06-14 2019-08-16 陕西莱特光电材料股份有限公司 有机电致发光材料及包含该材料的有机电致发光器件
CN110183333B (zh) * 2019-06-19 2020-06-30 陕西莱特光电材料股份有限公司 一种有机电致发光材料及包含该材料的有机电致发光器件
CN110563647B (zh) * 2019-08-27 2021-02-12 陕西莱特光电材料股份有限公司 含氮化合物、有机电致发光器件以及光电转化器件

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105308026A (zh) * 2013-07-09 2016-02-03 东曹株式会社 具有金刚烷基的环状吖嗪化合物、制造方法、以及以该化合物作为构成成分的有机电致发光元件
WO2017195669A1 (ja) * 2016-05-13 2017-11-16 コニカミノルタ株式会社 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、表示装置及び照明装置
CN106467553A (zh) * 2016-07-29 2017-03-01 江苏三月光电科技有限公司 一种含硼有机电致发光化合物及其在oled器件上的应用
WO2018150832A1 (ja) * 2017-02-16 2018-08-23 学校法人関西学院 有機電界発光素子
WO2018186396A1 (ja) * 2017-04-03 2018-10-11 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
WO2019004247A1 (ja) * 2017-06-30 2019-01-03 住友化学株式会社 発光素子及びその製造に有用な高分子化合物
WO2019162332A1 (en) * 2018-02-20 2019-08-29 Cynora Gmbh Organic molecules for optoelectronic devices
US20190280209A1 (en) * 2018-03-08 2019-09-12 Jnc Corporation Organic electroluminescent element
WO2019194298A1 (ja) * 2018-04-05 2019-10-10 出光興産株式会社 有機エレクトロルミネッセンス素子及び電子機器
CN109575059A (zh) * 2018-12-19 2019-04-05 武汉华星光电半导体显示技术有限公司 热活化延迟荧光材料、其制备方法和电致发光器件
CN110028459A (zh) * 2019-05-24 2019-07-19 上海天马有机发光显示技术有限公司 化合物、显示面板以及显示装置

Also Published As

Publication number Publication date
CN112028918B (zh) 2023-04-28
KR20220007702A (ko) 2022-01-18
KR102631942B1 (ko) 2024-02-01
CN112028918A (zh) 2020-12-04
US20220306655A1 (en) 2022-09-29

Similar Documents

Publication Publication Date Title
WO2021135750A1 (zh) 一种有机化合物、其应用以及有机电致发光器件
JP7410599B2 (ja) 有機エレクトロルミネッセンス材料、電子素子及び電子装置
WO2021135182A1 (zh) 含氮化合物、有机电致发光器件和电子装置
WO2022206493A1 (zh) 有机化合物及包含其的电子元件和电子装置
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
WO2021135183A1 (zh) 有机化合物、有机电致发光器件和电子装置
WO2022188514A1 (zh) 一种有机化合物及包含其的电子元件和电子装置
CN114133332B (zh) 有机化合物、电子元件及电子装置
JP7105388B1 (ja) 窒素含有化合物、電子部品及び電子装置
CN113906582A (zh) 有机发光器件
CN114989069B (zh) 含氮化合物和电子元件及电子装置
WO2023273416A1 (zh) 有机化合物、有机电致发光器件和电子装置
WO2022100194A1 (zh) 含氮化合物、有机电致发光器件和电子装置
WO2021120838A1 (zh) 有机化合物、电子器件及电子装置
CN115650899B (zh) 含氮化合物、电子元件和电子装置
CN111004207A (zh) 有机化合物、电子器件及电子装置
WO2022206389A1 (zh) 含氮化合物及包含其的电子元件和电子装置
CN113651703B (zh) 有机化合物、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
CN115521212A (zh) 有机材料、电子元件和电子装置
CN113493455B (zh) 有机化合物、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
CN114335399B (zh) 有机电致发光器件及包括其的电子装置
CN113735893B (zh) 一种有机化合物以及使用其的电子元件和电子装置
WO2023241137A1 (zh) 含氮化合物及有机电致发光器件和电子装置

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: 20909408

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20217043405

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 20909408

Country of ref document: EP

Kind code of ref document: A1