WO2024037073A1 - 含氮化合物、电子元件和电子装置 - Google Patents

含氮化合物、电子元件和电子装置 Download PDF

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WO2024037073A1
WO2024037073A1 PCT/CN2023/094373 CN2023094373W WO2024037073A1 WO 2024037073 A1 WO2024037073 A1 WO 2024037073A1 CN 2023094373 W CN2023094373 W CN 2023094373W WO 2024037073 A1 WO2024037073 A1 WO 2024037073A1
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group
substituted
unsubstituted
carbon atoms
independently selected
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French (fr)
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岳富民
李超超
许佳聪
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陕西莱特光电材料股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
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    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting 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
    • H10K85/60—Organic compounds having low molecular weight
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • This application belongs to the technical field of organic materials and specifically provides a nitrogen-containing compound, electronic components and electronic devices.
  • Organic electroluminescent devices also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials emit light when excited by current under the action of an electric field. It is a process of converting electrical energy into light energy.
  • organic electroluminescent diodes OLEDs have the advantages of active light emission, large optical path range, low driving voltage, high brightness, high efficiency, low energy consumption and simple manufacturing process. It is precisely because of these advantages that organic light-emitting materials and devices have become one of the most popular scientific research topics in the scientific community and industry.
  • Organic electroluminescent devices generally include an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode that are stacked in sequence.
  • a voltage is applied to the cathode and anode, the two electrodes generate an electric field.
  • the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the luminescent layer.
  • the electrons and holes combine in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state and release energy outwards, thereby causing the luminescent layer to emit light.
  • the purpose of this application is to provide a nitrogen-containing compound and electronic components and electronic devices using the same.
  • the nitrogen-containing compound can be used in electronic components to improve the performance of electronic components.
  • the first aspect of the present application provides a nitrogen-containing compound, which has a structure shown in the following formula 1:
  • R 2 to R 9 are the same or different, and each is independently hydrogen or deuterium;
  • R 1 and R 10 are the same or different, and are each independently selected from hydrogen, deuterium or group A, and one and only one of R 1 and R 10 is selected from group A, and the group A has a carbon number of Aryl groups with 6-12 carbon atoms or deuterated aryl groups with 6-12 carbon atoms;
  • Ar 1 and Ar 2 are the same or different, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms;
  • Each L is independently selected from a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 30 carbon atoms, n represents the number of L, and n Selected from 1 or 2, when n is 2, each L is the same or different;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted arylene group with 5 to 30 carbon atoms.
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, carbon number Aryl group with 6-18 carbon atoms, heteroaryl group with 5-18 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms or 3- Trialkylsilyl group of 12; in Ar 1 and Ar 2 , optionally, any two adjacent substituents form a saturated or unsaturated ring with a carbon number of 3-15.
  • a second aspect of the present application provides an electronic component, including an anode and a cathode arranged oppositely, and located between the anode and the cathode.
  • the functional layer wherein, the functional layer includes the nitrogen-containing compound described in the first aspect of this application.
  • a third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
  • the nitrogen-containing compound of the present application is based on specific benzocarbazole
  • As the mother core smaller aryl groups such as phenyl, biphenyl or naphthyl groups (hereinafter collectively referred to as small-structure aryl groups) are connected to the a or b-position of the mother core. These small-structure aryl groups are closely related to benzene.
  • the conjugation of the carbazole ring will make the electron cloud density distribution wider and increase the hole mobility of the molecule, thereby improving the efficiency of the resulting OLED device.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • Figure 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • the reference numbers are as follows: 100. Anode; 200. Cathode; 300. Functional layer; 310. Hole injection layer; 320. Hole transport layer; 321. First hole transport layer; 322. Second hole transport layer; 330. Organic light-emitting layer ; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • Example embodiments will now be described more fully with reference to the accompanying drawings.
  • Example embodiments may, however, be embodied in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concepts of the example embodiments. To those skilled in the art.
  • the described features, structures or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a thorough understanding of embodiments of the present application.
  • each...independently is and “...respectively and independently are” and “...independently selected from” are interchangeable, and should be understood in a broad sense. They can either be It means that in different groups, the specific options expressed by the same symbols do not affect each other. It can also mean that in the same group, the specific options expressed by the same symbols do not affect each other.
  • each q is independently 0, 1, 2 or 3
  • each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine.
  • Formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R can be the same or different, and the options of each R” do not affect each other;
  • Formula Q-2 indicates that there are q substituents R” on each benzene ring of biphenyl, and the R on the two benzene rings "The number of substituents q can be the same or different, each R" can be the same or different, and the options for each R" do not affect each other.
  • any two adjacent substituents form a ring means that any two substituents can form a ring but do not have to form a ring, which includes: the situation where two adjacent substituents form a ring and A situation in which two adjacent substituents do not form a ring.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituents are collectively referred to as Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc can be, for example, deuterium (D), halogen group, cyano group, alkyl group, aryl group, heteroaryl group, etc. base, deuterated alkyl group, haloalkyl group, trialkylsilyl group, etc.
  • the "substituted" functional group can be substituted by one or more of the above Rc; when two substituents Rc are connected to the same atom, the two substituents Rc can exist independently or Connected to each other to form a spiro ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc can exist independently or be fused to form a ring with the functional group to which they are connected.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L 1 is selected from a substituted arylene group having 20 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 20.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group.
  • the aryl group can be a single-ring aryl group, a fused-ring aryl group, or two or more single-ring aryl groups conjugated through a carbon-carbon bond.
  • Ring aryl groups monocyclic aryl groups conjugated through carbon-carbon bonds and fused-ring aryl groups, two or more fused-ring aryl groups conjugated through carbon-carbon bonds.
  • the condensed ring aryl group may include, for example, bicyclic condensed aryl group (such as naphthyl), tricyclic condensed aryl group (such as phenanthrenyl, fluorenyl, anthracenyl), etc.
  • Aryl groups do not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • naphthyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthrenyl, pyrenyl, benzofluoranthene, Key et al.
  • the arylene group refers to a bivalent group formed by the aryl group further losing one hydrogen atom.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group substituted by deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, etc. group substitution.
  • a deuterated aryl group can be one or two or more hydrogen atoms in the aryl group substituted by deuterium atoms.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuryl-substituted phenyl, dibenzothienyl-substituted phenyl, pyridyl-substituted phenyl, carbazolyl-substituted phenyl, etc. .
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with a carbon number of 30 refers to the aryl group and the substituted aryl group.
  • the total number of carbon atoms in the base is 30.
  • "Plural" means one, two or more.
  • the number of carbon atoms of the substituted or unsubstituted aryl group may be 6-30.
  • the number of carbon atoms of the substituted or unsubstituted aryl group is 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • a 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 single 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, pyrazinopyridyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thiophenyl
  • thienyl, furyl, phenanthrolinyl, etc. are heteroaryl groups with a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycyclic groups connected by conjugation of carbon-carbon bonds.
  • Ring system type heteroaryl refers to a bivalent group formed by the heteroaryl group further losing one hydrogen atom.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group substituted by deuterium atoms, halogen groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, haloalkyl groups, etc. group, deuterated alkyl and other groups.
  • aryl-substituted heteroaryl include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of a substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 5-30.
  • the number of carbon atoms of a substituted or unsubstituted heteroaryl group is 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 ,23,24,25,26,27, 28, 29 or 30.
  • non-located connecting bonds refer to single bonds protruding from the ring system. It means that one end of the bond 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-positioned bonds that penetrate the bicyclic ring, and its meaning includes such as the formula (f) -1) ⁇ Any possible connection method shown in formula (f-10):
  • the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned bond extending from the middle of one side of the benzene ring,
  • the meaning it represents includes any possible connection method shown in formula (X'-1) to formula (X'-4):
  • a non-positioned substituent in this application refers to a substituent connected through a single bond extending from the center of the ring system, which means that the substituent can be connected at any possible position in the ring system.
  • the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioned bond, and its meaning includes formula (Y-1) ⁇ Any possible connection method shown in formula (Y-7):
  • the alkyl group with 1 to 10 carbon atoms may include a linear alkyl group with 1 to 10 carbon atoms and a branched alkyl group with 3 to 10 carbon atoms.
  • the number of carbon atoms may be, for example, 1 or 2. ,3,4,5,6,7,8,9,10.
  • alkyl groups with 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the halogen group may include fluorine, iodine, bromine, chlorine, etc.
  • the number of carbon atoms of the trialkylsilyl group as a substituent may be 3-12, for example, 3, 6, 7, 8, 9, 10, 11, 12.
  • Specific examples of the trialkylsilyl group Including but not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, etc.
  • the number of carbon atoms of the haloalkyl group as a substituent may be 1-10, and the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • the haloalkyl group may be a fluoroalkyl group having 1 to 5 carbon atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
  • the number of carbon atoms of the aryl group as a substituent may be 6-18, and the number of carbon atoms may be, for example, 6, 10, 12, 13, 14, 15, 18, etc.
  • Specific examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, fluorene, phenanthrenyl, and the like.
  • the number of carbon atoms of the heteroaryl group as a substituent may be 5-18, and the number of carbon atoms may be, for example, 5, 6, 8, 9, 10, 11, 12, 18, etc.
  • Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolyl, dibenzofuryl, dibenzothienyl, carbazolyl, and the like.
  • this application provides a nitrogen-containing compound, which has a structure shown in Formula 1 below:
  • R 2 to R 9 are the same or different, and each is independently hydrogen (H) or deuterium (D). ;
  • R 1 and R 10 are the same or different, and are each independently selected from hydrogen, deuterium or group A, and one and only one of R 1 and R 10 is selected from group A, and the group A has a carbon number of Aryl groups with 6-12 carbon atoms or deuterated aryl groups with 6-12 carbon atoms;
  • Ar 1 and Ar 2 are the same or different, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms;
  • Each L is independently selected from a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group with 5 to 30 carbon atoms, n represents the number of L, and n Selected from 1 or 2, when n is 2, each L is the same or different;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, a substituted or unsubstituted arylene group with 5 to 30 carbon atoms.
  • the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 10 carbon atoms, carbon number Aryl group with 6-18 carbon atoms, heteroaryl group with 5-18 carbon atoms, deuterated alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms or 3- Trialkylsilyl group of 12; in Ar 1 and Ar 2 , optionally, any two adjacent substituents form a saturated or unsaturated ring with a carbon number of 3-15.
  • R 1 is group A and R 2 through R 10 are each independently hydrogen or deuterium.
  • R 10 is group A and R 1 through R 9 are each independently hydrogen or deuterium.
  • group A is selected from deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted biphenyl.
  • group A is selected from the group consisting of:
  • Ar 1 and Ar 2 can each be independently selected from, for example: carbon atoms with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 , 21, 22, 23, 24 or 25 substituted or unsubstituted aryl groups with carbon atoms of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 , 19, 20, 21, 22, 23, 24 or 25 substituted or unsubstituted heteroaryl.
  • Ar 1 and Ar 2 are the same or different, and each is independently a substituted or unsubstituted aryl group with 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group with 12 to 25 carbon atoms. .
  • Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or substituted dibenzothienyl, substituted or unsubstituted carbazolyl.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, and aromatic groups with 6 to 12 carbon atoms. base, a heteroaryl group with 5 to 12 carbon atoms, a deuterated alkyl group with 1 to 5 carbon atoms, a haloalkyl group with 1 to 5 carbon atoms, or a trialkyl silicone with 3 to 7 carbon atoms. group; optionally, in Ar 1 and Ar 2 , any two adjacent substituents form a saturated or unsaturated ring with 5-15 carbon atoms.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl , biphenyl, pyridyl, dibenzothienyl, dibenzofuranyl, carbazolyl, trideuteratedmethyl, trifluoromethyl or trimethylsilyl; optionally, Ar 1 and Ar 2 In , any two adjacent substituents form a benzene ring, cyclopentane, cycloalkane or fluorene ring.
  • Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted group V, wherein unsubstituted group V is selected from the following groups:
  • the substituted group V has one or more substituents, and each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trimethylsilyl, Deuterated methyl, trifluoromethyl, phenyl, naphthyl or pyridyl.
  • Ar 1 and Ar 2 are each independently selected from the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • L can be selected from, for example: substituted or unsubstituted substituents with carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.
  • Aryl group is a heteroarylene group with 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
  • each L is independently a substituted or unsubstituted arylene group having 6-15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 10-18 carbon atoms.
  • L 1 and L 2 can be selected from, for example: single bonds with carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 Substituted or unsubstituted arylene group, heteroarylene group with carbon atoms of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 .
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-18 carbon atoms, a substituted or unsubstituted arylene group with 10-18 carbon atoms. Substituted heteroarylene.
  • L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenylene, substituted or unsubstituted fluorenylene group, substituted or unsubstituted pyridylene group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted dibenzofurylene group, substituted or unsubstituted carbazolylene group.
  • L 1 and L 2 are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted Substituted phenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofurylene, substituted or Unsubstituted carbazolylidene.
  • the substituents in L, L 1 and L 2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms or 6-10 carbon atoms. of aryl groups.
  • the substituents in L, L 1 and L 2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, methyl, ethyl, isopropyl, tert-butyl base, phenyl or naphthyl.
  • the structure is The two L's can be the same or different.
  • n 2
  • one of the two L is substituted or unsubstituted phenyl
  • the other is substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene.
  • each L is independently selected from a substituted or unsubstituted group W
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted group W, wherein an unsubstituted group W is selected from the following groups:
  • the substituted group W has one or more substituents, and each substituent is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, phenyl, trimethylsilyl, trimethylsilyl, Deuterated methyl or trifluoromethyl.
  • each L is independently selected from the group consisting of:
  • L 1 and L 2 are each independently selected from the group consisting of a single bond and the following groups:
  • L 1 and L 2 are each independently selected from the group consisting of a single bond and the following groups:
  • Each is independently selected from the group consisting of:
  • the nitrogen-containing compound is selected from the group consisting of:
  • the synthesis method of the nitrogen-containing compound provided in this application is not particularly limited. Those skilled in the art can determine the appropriate synthesis method based on the preparation method provided in the synthesis examples section of the nitrogen-containing compound in this application. In other words, the synthesis examples of the present invention exemplarily provide methods for synthesizing nitrogen-containing compounds, and the raw materials used can be obtained through commercial purchases or methods well known in the art. Those skilled in the art can obtain all nitrogen-containing compounds provided in this application based on these exemplary synthesis methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Those skilled in the art should not understand that this application is limit.
  • a second aspect of the present application provides an electronic component, including an anode and a cathode arranged oppositely, and a functional layer disposed between the anode and the cathode; the functional layer includes the nitrogen-containing compound described in the first aspect of the present application. compound.
  • the functional layer includes a hole transport layer, and the hole transport layer contains the nitrogen-containing compound provided by the present application.
  • the electronic components are selected from organic electroluminescent devices or photoelectric conversion devices.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device includes an anode 100, a hole transport layer 320, an organic light emitting layer 330, and an electron transport layer that are stacked in sequence. 340 and cathode 200.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto.
  • a transparent electrode including indium tin oxide (ITO) as an anode is included.
  • the hole transport layer 320 contains the nitrogen-containing compound of the present application.
  • the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 arranged in a stack, and relative to the second hole transport layer 322, the first hole transport layer Layer 321 is closer to the anode.
  • the second hole transport layer is also called an electron blocking layer.
  • the material of the first hole transport layer 321 can be selected from phthalocyanine derivatives, naphthocyanine derivatives, porphyrin derivatives, benzidine-type triarylamines, styrylamine-type triarylamines, and diamine-type triarylamines.
  • Amine or other types of materials can be selected by those skilled in the art with reference to existing technologies.
  • the material of the first hole transport layer 321 is selected from the group consisting of the following compounds:
  • the material of the first hole transport layer 321 is HT-1.
  • the second hole transport layer 322 includes the nitrogen-containing compound of the present application.
  • the organic light-emitting layer 330 includes a host material and a guest material.
  • the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy.
  • the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the organic light-emitting layer 330 may be metal chelate compounds, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, anthracene derivatives or other types of materials.
  • the host material is selected from one or more than two of the following compounds:
  • the host material of the organic light-emitting layer 330 is BH-1.
  • the guest material of the organic light-emitting 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, a bisarylamine derivative with a condensed aromatic subunit, or other materials.
  • the guest material is selected from at least one of the following compounds:
  • the guest material of the organic light-emitting layer 330 is BD-1.
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
  • the electron transport materials may generally include metal complexes and/or nitrogen-containing heterocyclic derivatives, where , the metal complex material can be selected from, for example, LiQ, Alq 3 , Bepq 2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or a five-membered ring skeleton, with a nitrogen-containing Condensed aromatic ring compounds with a six-membered ring or a five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as BCP, Bphen, NBphen, DBimiBphen, BimiBphen, etc., or at least one of the following compounds A sort of:
  • electron transport layer 340 is composed of ET-1 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.
  • a hole injection layer 310 may also be provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321 .
  • the hole injection layer 310 can be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • hole injection layer 310 is selected from the group consisting of:
  • the hole injection layer 310 is composed of F4-TCNQ.
  • an electron injection layer 350 may also be 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 an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic substance.
  • the electron injection layer 350 includes LiQ or Yb, or a combination of Mg and LiF.
  • the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a blue light device.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 arranged opposite each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 .
  • the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , an organic light-emitting layer 330 , an electron transport layer 340 and a cathode 200 that are stacked in sequence.
  • the hole transport layer 320 contains the nitrogen-containing compound provided by the present application.
  • the photoelectric conversion device is a solar cell, especially an organic thin film solar cell.
  • a third aspect of this application provides an electronic device, including the electronic component described in the second aspect of this application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 is, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices.
  • it may include but is not limited to a computer screen, a mobile phone screen, a television, electronic paper, emergency lighting, an optical module, etc.
  • the electronic device is a second electronic device 500
  • the second electronic device 500 includes the above-mentioned photoelectric conversion device.
  • the second electronic device 500 is, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all commercially available raw material products.
  • reaction solution was cooled to room temperature, toluene (200 mL) was added for extraction, the organic phases were combined, dried with anhydrous magnesium sulfate, the organic phase was passed through a silica gel chromatography column to remove the catalyst, and the solvent was distilled off under reduced pressure to obtain a yellow oil IM IA- 2 (32.8g, yield 65.8%).
  • IM I-g to IM I-i are synthesized.
  • the difference is that the raw material 3 is used instead of phenylboronic acid to react with IM I-f-2.
  • the other conditions remain unchanged.
  • the synthesized intermediates and their The yield is shown in 2.
  • reaction solution was cooled to room temperature, washed with water until neutral, the organic phases were combined and dried using anhydrous magnesium sulfate, the organic phase was passed through a silica gel column to remove the catalyst, and the solvent was distilled off under reduced pressure; a yellow oily substance IJ-1 (24.23g) was obtained , yield 48.0%).
  • IM I-k was synthesized using the same synthesis method as IM I-j, except that phenylboronic acid was used instead of (2-bromophenyl-3,4,5,6-d4)boronic acid. Keeping other conditions unchanged, IM I-k (13.17g, yield 62.1% in the last step) was obtained.
  • Example 1 Blue organic electroluminescent device
  • Preparing the device anode Coating three layers of ITO/Ag/ITO material (thickness respectively: )'s glass substrate was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and the photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns. Ultrapure water and isopropyl alcohol were first used to clean the surface. Clean the contaminants on the surface of the substrate; then use O2 : N2 plasma gas to treat the surface of the substrate.
  • the compound F4-TCNQ was evaporated on the experimental substrate (anode) to form a thickness of hole injection layer (HIL), and HT-1 is evaporated on the surface of the hole injection layer to form a thickness of The first hole transport layer (HTL-1).
  • HIL hole injection layer
  • HTL-1 The first hole transport layer
  • Compound 6 is vacuum evaporated on the first hole transport layer to form a thickness of The second hole transport layer (HTL-2).
  • the compound BD-1:BH-1 was evaporated at a weight ratio of 2%:98% to form a thickness of organic light-emitting layer (EML).
  • EML organic light-emitting layer
  • the compounds ET-1 and LiQ were co-evaporated at a weight ratio of 1:1 to form Thick electron transport layer (ETL).
  • ETTL Thick electron transport layer
  • Ytterbium (Yb) is evaporated on the electron transport layer to form a thickness of electron injection layer (EIL).
  • magnesium (Mg) and silver (Ag) were co-evaporated at a weight ratio of 1:9 to form a thickness of the cathode.
  • CPL Organic coating layer
  • An organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 6 (column "HTL-2”) was used to replace the compound 6 in Example 1 when preparing the second hole transport layer. .
  • An organic electroluminescent device was prepared using the same method as in Example 1, except that when preparing the second hole transport layer, Compound A, Compound B, Compound C and Compound D were used instead of Compound 6 in Example 1.
  • the organic electroluminescent devices prepared in Examples 1-35 and Comparative Examples 1-4 were tested for performance. Specifically, the IVL performance of the device was tested under the condition of 10mA/ cm2 . The T 95 device life was at 15mA/ cm2 . The test was carried out under the conditions, and the test results are shown in Table 6.
  • the organic electroluminescent device prepared in Examples 1-35 uses the nitrogen-containing compound of the present application as the second hole transport layer material.
  • the performance has been improved, mainly as the luminous efficiency of the device has been increased by at least 23.2%, and the T 95 lifespan has been increased by at least 25.8%.
  • the compound of the present invention when used as a second hole transport layer material to prepare an organic electroluminescent device, it can effectively extend the life of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.

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Abstract

本申请属于有机材料技术领域，涉及一种含氮化合物、电子元件和电子装置，该化合物具有如下式(1)所示的结构。本申请的含氮化合物能改善电子元件的性能。

Description

含氮化合物、电子元件和电子装置
相关申请的交叉引用
本申请要求于2022年8月17日递交的申请号为202210988201.1的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请属于有机材料技术领域，具体提供一种含氮化合物、电子元件和电子装置。
背景技术
有机电致发光器件又称为有机发光二极管，是指有机发光材料在电场作用下，受到电流的激发而发光的现象。它是一种将电能转换为光能的过程。相比于无机发光材料，有机电致发光二极管OLED具有主动发光、光程范围大、驱动电压低、亮度大、效率高、耗能少以及制作工艺简单等优点。正是由于这些优点，有机发光材料与器件已经成为科学界和产业界十分热门的科研课题之一。
有机电致发光器件一般包括依次层叠设置的阳极、空穴传输层、电子阻挡层、发光层、电子传输层、电子注入层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，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，进而使得发光层对外发光。
目前，有机电致发光器件的使用过程中存在发光效率降低和寿命缩短等问题，导致有机电致发光器件的性能下降。
发明内容
针对现有技术存在的上述问题，本申请的目的在于提供一种含氮化合物以及使用其的电子元件和电子装置，该含氮化合物可用于电子元件中，提高电子元件的性能。
为了实现上述目的，本申请第一方面提供一种含氮化合物，所述含氮化合物具有如下式1所示的结构：
其中，R2至R9相同或不同，且各自独立地为氢或氘；
R1和R10相同或不同，各自独立地选自氢、氘或基团A，且R1和R10中有且仅有一个选自基团A，所述基团A为碳原子数为6-12的芳基或碳原子数为6-12的氘代芳基；
Ar1和Ar2相同或不同，且各自独立地为碳原子数为6-30的取代或未取代的芳基、碳原子数为5-30的取代或未取代的杂芳基；
各L独立地选自碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基，n表示L的个数，且n选自1或2，当n为2时，各L相同或不同；
L1和L2相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基；
L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-18的芳基、碳原子数为5-18的杂芳基、碳原子数为1-10的氘代烷基、碳原子数为1-10的卤代烷基或碳原子数为3-12的三烷基硅基；在Ar1和Ar2中，任选地，任意两个相邻的取代基形成碳原子数为3-15的饱和或不饱和环。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间 的功能层；其中，所述功能层包含本申请第一方面所述的含氮化合物。
本申请第三方面提供一种电子装置，包含本申请第二方面所述的电子元件。
本申请的含氮化合物以特定的苯并咔唑作为母核，并在该母核的a或b号位连接有苯基、联苯基或萘基等体积较小的芳基(下文统称为小结构芳基)，这些小结构芳基与苯并咔唑环的共轭作用会使电子云密度分布范围更大，提升分子的空穴迁移率，从而使所得OLED器件的效率有所提升。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的结构示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的结构示意图。
附图标记如下：
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、有机发光层；340、电子传输层；350、电子注入层；360、光电转化层；400、第一电子装置；500、第二电子装置。
具体实施方式
以下结合附图对本发明的具体实施方式进行详细说明。应当理解地是，此处所描述的具体实施方式仅用于说明和解释本发明，并不用于限制本发明。
现在将参考附图更全面地描述示例实施方式。然而，示例实施方式能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施方式使得本申请将更加全面和完整，并将示例实施方式的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施方式中。在下面的描述中，提供许多具体细节从而给出对本申请的实施方式的充分理解。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，任意两个相邻的取代基形成环”意味着任意的两个取代基可以形成环但不是必须形成环，其包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
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Rc例如可以为氘(D)、卤素基团、氰基、烷基、芳基、杂芳 基、氘代烷基、卤代烷基、三烷基硅基等。在本申请中，“取代的”官能团可以被上述Rc中的1个或2个以上所取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成螺环；当官能团上存在两个相邻的取代基Rc时，两个相邻的取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L1选自碳原子数为20的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为20。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言，在本申请中，萘基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、基等。本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基等基团取代。氘代芳基可以是芳基中的一个或者两个以上氢原子被氘原子取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩基取代的苯基、吡啶基取代的苯基、咔唑基取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为30的取代的芳基，指的是芳基和取代基的总碳原子数为30。“多个”是指一个、两个或更多个。
在本申请中，取代或未取代的芳基的碳原子数可以为6-30。例如，取代或未取代的芳基的碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29或30。
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、芳基、杂芳基、三烷基硅基、烷基、卤代烷基、氘代烷基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，取代或未取代的杂芳基的碳原子数可以为5-30。例如，取代或未取代的杂芳基的碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、 28、29或30。
本申请中，不定位连接键是指从环体系中伸出的单键其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式：
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式：
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，如下式(Y)中所示地，式(Y)所表示的取代基R'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：
本申请中，碳原子数为1-10的烷基可以包括碳原子数1-10的直链烷基和碳原子数为3-10的支链烷基，碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1-10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
本申请中，卤素基团可以包括氟、碘、溴、氯等。
在本申请中，作为取代基的三烷基硅基的碳原子数可以为3-12，例如为3、6、7、8、9、10、11、12，三烷基硅基的具体实例包括但不限于，三甲基硅基、乙基二甲基硅基、三乙基硅基等。
在本申请中，作为取代基的卤代烷基的碳原子数可以为1-10，碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。例如卤代烷基可以为碳原子数为1-5的氟代烷基。卤代烷基的具体实例包括但不限于，三氟甲基。
在本申请中，作为取代基的芳基的碳原子数可以为6-18，碳原子数例如可以为6、10、12、13、14、15、18等。作为取代基的芳基的具体实例包括但不限于，苯基、萘基、联苯基、芴、菲基等。
在本申请中，作为取代基的杂芳基的碳原子数可以为5-18，碳原子数例如可以为5、6、8、9、10、11、12、18等。作为取代基的杂芳基的具体实例包括但不限于，吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、咔唑基等。
第一方面，本申请提供一种含氮化合物，所述含氮化合物具有如下式1所示的结构：
其中，R2至R9(R2、R3、R4、R5、R6、R7、R8和R9)相同或不同，且各自独立地为氢(H)或氘(D)；
R1和R10相同或不同，各自独立地选自氢、氘或基团A，且R1和R10中有且仅有一个选自基团A，所述基团A为碳原子数为6-12的芳基或碳原子数为6-12的氘代芳基；
Ar1和Ar2相同或不同，且各自独立地为碳原子数为6-30的取代或未取代的芳基、碳原子数为5-30的取代或未取代的杂芳基；
各L独立地选自碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基，n表示L的个数，且n选自1或2，当n为2时，各L相同或不同；
L1和L2相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基，碳原子数为5-30的取代或未取代的亚杂芳基；
L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-18的芳基、碳原子数为5-18的杂芳基、碳原子数为1-10的氘代烷基、碳原子数为1-10的卤代烷基或碳原子数为3-12的三烷基硅基；在Ar1和Ar2中，任选地，任意两个相邻的取代基形成碳原子数为3-15的饱和或不饱和环。
在一些实施方式中，R1为基团A，R2至R10各自独立地为氢或氘。
在另一些实施方式中，R10为基团A，R1至R9各自独立地为氢或氘。
可选地，基团A选自氘取代或未取代的苯基、氘取代或未取代的萘基、氘取代或未取代的联苯基。
进一步可选地，基团A选自以下基团所组成的组：
本申请中，Ar1和Ar2例如可以各自独立地选自：碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25的取代或未取代的芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25的取代或未取代的杂芳基。
可选地，Ar1和Ar2相同或不同，且各自独立地为碳原子数为6-25的取代或未取代的芳基、碳原子数为12-25的取代或未取代的杂芳基。
在一些实施方式中，Ar1和Ar2各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的 芴基、取代或未取代的三亚苯基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或取代的二苯并噻吩基、取代或未取代的咔唑基。
可选地，Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的氘代烷基、碳原子数为1-5的卤代烷基或碳原子数为3-7的三烷基硅基；任选地，在Ar1和Ar2中，任意两个相邻的取代基形成碳原子数为5-15的饱和或不饱和环。
在一些实施方式中，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并噻吩基、二苯并呋喃基、咔唑基、三氘代甲基、三氟甲基或三甲基硅基；任选地，Ar1和Ar2中，任意两个相邻的取代基形成苯环、环戊烷、环基烷或芴环。
在一些实施方式中，Ar1和Ar2各自独立地选自取代或未取代的基团V，其中，未取代的基团V选自以下基团：
取代的基团V中具有一个或两个以上取代基，各取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、三氘代甲基、三氟甲基、苯基、萘基或吡啶基。
可选地，Ar1和Ar2各自独立地选自以下基团：
进一步可选地，Ar1和Ar2各自独立地选自如下基团所组成的组：

本申请中，L例如可以选自：碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的取代或未取代的亚芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的亚杂芳基。
在一些实施方式中，各L独立地为碳原子数为6-15的取代或未取代的亚芳基、碳原子数为10-18的取代或未取代的亚杂芳基。
本申请中，L1和L2例如可以选自：单键，碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的取代或未取代的亚芳基，碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的亚杂芳基。
可选地，L1和L2相同或不同，且各自独立地选自单键、碳原子数为6-18的取代或未取代的亚芳基、碳原子数为10-18的取代或未取代的亚杂芳基。
在一些实施方式中，L选自取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基。
在一些实施方式中，L1和L2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基。
可选地，L、L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、碳原子数为1-4的烷基或碳原子数为6-10的芳基。
可选地，L、L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、甲基、乙基、异丙基、叔丁基、苯基或萘基。
在本申请中，当n＝2时，的结构为这两个L可以相同或不同。
在一些实施方式中，n＝2，两个L中的一个为取代或未取代的苯基，另一个为取代或未取代的亚苯基、取代或未取代的亚萘基。
在一些实施方式中，各L独立地选自取代或未取代的基团W，L1和L2各自独立地选自单键、取代或未取代的基团W，其中，未取代的基团W选自以下基团：
取代的基团W中具有一个或两个以上取代基，各取代基独立地选自氘、氟、氰基、碳原子数为1-4的烷基、苯基、三甲基硅基、三氘代甲基或三氟甲基。
可选地，各L独立地选自以下基团所组成的组：
可选地，选自以下基团所组成的组：
可选地，选自以下基团所组成的组：
可选地，L1和L2各自独立地选自单键和以下基团所组成的组：
进一步可选地，L1、L2各自独立地选自单键和以下基团所组成的组：
在一些实施方式中，各自独立地选自以下基团组成的组：

在一些更具体的实施方式中，所述含氮化合物选自以下化合物所组成的组：








本申请对提供的含氮化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的含氮化合物结合合成例部分提供的制备方法确定合适的合成方法。换言之，本发明的合成例部分示例性地提供了含氮化合物的合成方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的合成方法得到本申请提供的所有含氮化合物，在此不再详述制备该含氮化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的含氮化合物。
可选地，所述功能层包括空穴传输层，所述空穴传输层包含本申请所提供的含氮化合物。
可选地，所述电子元件选自有机电致发光器件或光电转换器件。
可选地，所述电子元件为有机电致发光器件，如图1所示，所述有机电致发光器件包括依次层叠设置的阳极100、空穴传输层320、有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO2: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，所述空穴传输层320包含本申请的含氮化合物。
可选地，所述空穴传输层320包括层叠设置的第一空穴传输层321和第二空穴传输层322，且相对所述第二空穴传输层322，所述第一空穴传输层321更靠近所述阳极。所述第二空穴传输层也称为电子阻挡层。
本申请中，所述第一空穴传输层321的材料可以选自酞菁衍生物、萘菁衍生物、卟啉衍生物、联苯胺型三芳胺、苯乙烯胺型三芳胺、二胺型三芳胺或者其他类型的材料，本领域技术人员可参照现有技术选择。例如，所述第一空穴传输层321的材料选自以下化合物所组成的组：
在一种具体的实施方式中，所述第一空穴传输层321的材料为HT-1。
可选地，所述第二空穴传输层322包含本申请的含氮化合物。
可选地，所述有机发光层330包含主体材料和客体材料，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物、蒽类衍生物或者其他类型的材料。例如，所述主体材料选自以下化合物中的一种或两种以上：
在一种具体的实施方式中，有机发光层330的主体材料为BH-1。
有机发光层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、具有稠合芳香亚基的双芳胺衍生物或者其他材料，本申请对此不做特殊的限制。例如，所述客体材料选自以下化合物中的至少一种：
在一种具体的实施方式中，有机发光层330的客体材料为BD-1。
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，电子传输材料通常可以包含金属络合物和/或含氮杂环衍生物，其中，所述金属络合物材料例如可以选自LiQ、Alq3、Bepq2等；所述含氮杂环衍生物可以为具有含氮六元环或五元环骨架的芳香族环、具有含氮六元环或五元环骨架的稠合芳香族环化合物等，具体实例包括但不限于，BCP、Bphen、NBphen、DBimiBphen、BimiBphen等1,10-菲咯啉类化合物，或者以下化合物中的至少一种：
在一种具体的实施方式中，电子传输层340由ET-1和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO2/Al、LiF/Ca、LiF/Al和BaF2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310选自以下化合物所组成的组：
在一种具体的实施方式中，空穴注入层310由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350包括LiQ或Yb，或者包括Mg和LiF的组合物。
本申请中，所述有机电致发光器件可以为蓝光器件、红光器件或绿光器件，优选为蓝光器件。
按照另一种实施方式，电子元件为光电转化器件。如图3所示，该光电转化器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300。
按照一种具体的实施方式，如图3所示，光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、有机发光层330、电子传输层340和阴极200。可选地，所述空穴传输层320包含本申请提供的含氮化合物。
可选地，光电转化器件为太阳能电池，尤其是可以为有机薄膜太阳能电池。
本申请第三方面提供一种电子装置，包括本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
以下，通过实施例对本申请进一步详细说明。但是，下述实施例仅是本申请的例示，而并非限定本申请。
本申请中未提到的合成方法的化合物的都可通过商业途径获得的原料产品。
一、中间体IM I-X合成
1、以IM I-A为例来说明IM I-X的合成
(1)N2保护下，向三口烧瓶中加入1,8-萘二硼酸(40.00g，185.36mmol)，溴苯(29.1g，185.36mmol)、碳酸钾(56.1g，405.93mmol)、四丁基溴化铵(11.9g，37.06mmol)、甲苯(300mL)、乙醇(120mL)和去离子水(80mL)加入三口烧瓶中，搅拌15min后加入四三苯基膦钯(4.3g，3.71mmol)并升温至75℃-80℃，搅拌8小时。将反应液冷却至室温，加入甲苯(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相过硅胶色谱柱除去催化剂，再用乙酸乙酯/无水乙醇重结晶两次；得到白色固体，即为中间体IM I-A-1(38.2g，收率83.1％)。
(2)N2保护下，将IM I-A-1(38.0g，153.17mmol)、邻溴硝基苯(30.9g，153.17mmol)、碳酸钾(46.4g，335.75mmol)、四丁基溴化铵(10.0g，31.09mmol)、甲苯(300mL)、乙醇(120mL)和去离子水(80mL)加入三口烧瓶中，搅拌15min后加入四三苯基膦钯(3.5g，3.05mmol)并升温至75℃-80℃，搅拌40h。将反应液冷却至室温，加入甲苯(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相过硅胶色谱柱除去催化剂，减压蒸馏除去溶剂；得到黄色油状物IM I-A-2(32.8g，收率65.8％)。
(3)N2保护下，将IM I-A-2(32.0g，98.35mmol)、三苯基膦(59.3g，226.10mmol)和300mL邻二氯苯加入三口烧瓶中，于搅拌下升温至150℃反应18h。减压蒸馏除去邻二氯苯，所得黑色残渣用正己烷萃取3次，收集萃取液过硅胶色谱柱，然后减压蒸馏除去溶剂，得到银灰色鳞片状固体，即为IM I-A(17.1g，收率59.3％)。
2、参照合成IM I-A的方法合成其他IM I-X，不同的是，以原料1代替溴苯，以原料2代替邻溴硝基苯，各步骤合成的中间体及最后一步收率如表1所示。
表1
二、中间体IM I-f至IM I-i的合成
1、IM I-f的合成
(1)采用与IM I-A-2相同的方法制备IM I-f-1，不同之处在于：分别用1-萘硼酸代替IM I-A-1，用2,3-二溴硝基苯代替邻溴硝基苯，其他条件不变，得到IM I-f-1(28.5g，收率72.4％)。
(2)采用与IM I-A相同的方法制备IM I-f-2，不同之处在于：用IM I-f-1代替IM I-A-2，其他条件不变，得到IM I-f-2(15.7g，收率62.2％)。
(3)N2保护下，将IM I-f-2(15g，50.65mmol)、苯硼酸(6.48g，53.18mmol)、碳酸钾(16.09g，116.49mmol)、四丁基溴化铵(3.26g，10.13mmol)、甲苯(90mL)、乙醇(45mL)和去离子水(30mL)加入三口烧瓶中，搅拌15min后加入四三苯基膦钯(2.93g，2.53mmol)并升温至75℃-80℃，搅拌16小时；将反应液冷却至室温，加入甲苯(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，将有机相过硅胶色谱柱除去催化剂，减压蒸馏除去溶剂；得到黄色油状物IM I-f(10.8g，收率72.7％)。
2、IM I-g至IM I-i的合成
按照IM I-f的合成方法(步骤(3))合成IM I-g至IM I-i，不同之处在于：用原料3代替苯硼酸以与IM I-f-2反应，其他条件不变，所合成的中间体及其收率如2所示。
表2
三、中间体IM I-j和IM I-k的合成
1、IM I-j的合成
(1)N2保护下，将(2-溴苯基-3,4,5,6-d4)硼酸(50g，244.02mmol)、氘代苯硼酸(46.49g，366.02mmol)、碳酸钾(77.56g，561.25mmol)、四丁基溴化铵(15.73g，48.80mmol)、甲苯(400mL)、乙醇(150mL)和去离子水(100mL)加入三口烧瓶中，搅拌15min后加入四三苯基膦钯(14.10g，12.20mmol)并升温至75℃-80℃，搅拌8小时。随后将反应液冷却至室温，水洗至中性，合并有机相并使用无水硫酸镁进行干燥，将有机相过硅胶柱除去催化剂，减压蒸馏除去溶剂；得到黄色油状物I-J-1(24.23g，收率48.0％)。
(2)N2保护下，将I-J-1(24g，115.87mmol)、1-溴-2-硝基萘(43.82g，173.83mmol)、碳酸钾(36.83g，266.54mmol)、四丁基溴化铵(7.47g，23.18mmol)、甲苯(280mL)、乙醇(80mL)和去离子水(60mL)加入三口烧瓶中，搅拌30min后加入四三苯基膦钯(6.7g，5.79mmol)并升温至75℃-80℃，搅拌36小时。随后将反应液冷却至室温，水洗至中性，合并有机相并使用无水硫酸镁进行干燥，将有机相过硅胶柱(石油醚：二氯甲烷＝2:1，v/v)，收集产物点，减压蒸馏除去溶剂，得到白色粉末状固体I-J-2(22.15g，收率57.2％)。
(3)采用与IM I-A相同的方法制备IM I-j，不同之处在于：用I-J-2代替IM I-A-2，其他条件不变，得到IM I-j(12.31g，收率56.9％)。
2、IM I-k的合成
采用与IM I-j相同的合成方法合成IM I-k，不同之处在于：用苯硼酸代替(2-溴苯基-3,4,5,6-d4)硼酸。其他条件不变，得到IM I-k(13.17g，最后一步收率62.1％)。
四、中间体IM I-X-Y合成
1、IM I-A-L1的合成
N2保护下，向1L的三口烧瓶中依次加入IM I-A(15g，51.13mmol)、对氯溴苯(9.79g，51.13mmol)、 碘化亚铜(0.19g，1.02mmol)、碳酸钾(14.12g，102.26mmol)、1,10-菲啰啉(5.07g，25.56mmol)和18-冠醚-6(0.13g,0.51mmol)，然后加入150mL的DMF，继续通氮气20min，缓慢加热升温至回流并搅拌24h。降温至室温，将反应液加入1L水中除去DMF，并用二氯甲烷萃取后用无水硫酸镁干燥30min，然后减压蒸馏除去溶剂，用二氯甲烷/石油醚(体积比1∶2)过硅胶色谱柱得到为灰白色固体的IM I-A-L1(15.18g，收率73.5％)。
2、参照合成IM I-A-L1的方法合成其他IM I-X-Y，不同的是，以原料4代替IM I-A，以原料5代替对氯溴苯，所采用的主要原料、合成的中间体及其收率如表3所示。
表3


五、中间体IM I-k-L1合成
N2保护下，将IM I-k-L(20g，48.04mmol)、1-溴-2-硝基萘(13.79g，57.65mmol)、碳酸钾(15.27g，110.50mmol)、四丁基溴化铵(3.1g，9.61mmol)、甲苯(160mL)、乙醇(60mL)和去离子水(40mL)加入三口烧瓶中，搅拌30min后加入四三苯基膦钯(2.78g，2.40mmol)并升温至75℃-80℃，搅拌36小时；随后将反应液冷却至室温，水洗至中性，合并有机相并使用无水硫酸镁进行干燥，将有机相过硅胶柱(石油醚：二氯甲烷＝2:1，v/v)，收集产物点，减压蒸馏除去溶剂；得到白色粉末状固体IM I-k-L1(15.23g，收率59.6％)。
合成例1：化合物6的合成
(1)将IM I-A-L1(15g,37.14mmol)，4-氨基联苯(6.16g,36.3mmol)，三(二亚苄基丙酮)二钯(0.34g,0.37mmol)，2-二环己基膦-2',4',6'-三异丙基联苯(0.35g,0.74mmol)以及叔丁醇钠(5.35g,55.71mmol)加入甲苯(150mL)中，氮气保护下加热至108℃，搅拌4h；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得到黄色固体粗品；再使用甲苯体系对粗品进行重结晶提纯，得到IM I-A-N(12.69g，收率64.6％)。
(2)将IM I-A-N(10g,18.63mmol)，4-溴联苯(4.56g,19.56mmol)，三(二亚苄基丙酮)二钯(0.17g,0.19mmol)，2-二环己基膦-2’,6’-二甲氧基联苯(0.15g,0.38mmol)以及叔丁醇钠(2.69g,27.95mmol)加入甲苯(100mL)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，得到白色固体化合物6(6.96g,收率54.2％),质谱：m/z＝689.3[M+H]+。
合成例2-35
参照合成化合物6的方法合成其他化合物，不同的是，以原料6代替IM I-A-L1，以原料7代替4-氨基联苯，以原料8代替4-溴联苯，所采用的主要原料、合成的化合物及最后一步收率、质谱表征结果如表4所示。
表4




部分化合物的核磁数据如表5所示。
表5
有机电致发光器件的制作及评估实施例
实施例1：蓝色有机电致发光器件
制备器件阳极：将镀有ITO/Ag/ITO三层材料(厚度分别为)的玻璃基板切割成40mm×40mm×0.7mm的尺寸，采用光刻工艺，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，先使用超纯水和异丙醇对其表面清洗，清洗基板表面的污染物；然后采用O2:N2等离子气体对基板表面进行处理。
在实验基板(阳极)上蒸镀化合物F4-TCNQ，形成厚度为的空穴注入层(HIL)，并且在空穴注入层表面蒸镀HT-1，形成厚度为的第一空穴传输层(HTL-1)。
在第一空穴传输层上真空蒸镀化合物6，形成厚度为的第二空穴传输层(HTL-2)。
在第二空穴传输层上将化合物BD-1：BH-1以2％：98％的重量比进行蒸镀，形成厚度为的有机发光层(EML)。
在有机发光层上，将化合物ET-1和LiQ以1:1的重量比进行共同蒸镀，形成厚的电子传输层(ETL)。
在电子传输层上蒸镀镱(Yb)，形成厚度为的电子注入层(EIL)。
在电子注入层上，将镁(Mg)和银(Ag)以1：9的重量比共同蒸镀，形成厚度为的阴极。
最后，在上述阴极上蒸镀CP-05，形成厚度为有机覆盖层(CPL)，从而完成有机发光器件的制备。
实施例2-35
除了在制备第二空穴传输层时，以表6中的化合物(“HTL-2”列)替代实施例1中的化合物6之外，利用与实施例1相同的方法制备有机电致发光器件。
比较例1-4
除了在制备第二空穴传输层时，分别以化合物A、化合物B、化合物C和化合物D替代实施例1中的化合物6之外，利用与实施例1相同的方法制备有机电致发光器件。
以上实施例和比较例中，在制备有机电致发光器件时，所使用的各个材料的结构如下所示。

对实施例1-35和比较例1-4制备所得的有机电致发光器件进行性能测试，具体在10mA/cm2的条件下测试了器件的IVL性能，T95器件寿命在15mA/cm2的条件下进行测试，测试结果展示在表6中。
表6

参照表6可知，相较于比较例1-4所制备的有机电致发光器件，实施例1-35以本申请的含氮化合物作为第二空穴传输层材料所制备的有机电致发光器件性能得到改善，主要表现为器件的发光效率至少提高了23.2％，T95寿命至少提高了25.8％。
根据比较例4的测试结果，可以看出相较于具有大共轭平面的三亚苯基类芳基，小结构芳基连接在a或b号位，在空间结构上增加了分子的扭曲度，从而使材料在器件制作过程中保持较高的非晶性，进而改善OLED器件的寿命。
综上，将本发明的化合物作为第二空穴传输层材料用于制备有机电致发光器件时，可以有效的延长有机电致发光器件的寿命，并且提升有机电致发光器件的发光效率。
以上结合附图详细描述了本申请的优选实施方式，但是，本申请并不限于上述实施方式中的具体细节，在本申请的技术构思范围内，可以对本公开的技术方案进行多种简单变型，这些简单变型均属于本申请的保护范围。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，本申请对各种可能的组合方式不再另行说明。

Claims (15)

  1. 一种含氮化合物，其具有如下式1所示的结构：
    其中，R2至R9相同或不同，且各自独立地为氢或氘；
    R1和R10相同或不同，且各自独立地选自氢、氘或基团A，且R1和R10中有且仅有一个选自基团A，所述基团A为碳原子数为6-12的芳基或碳原子数为6-12的氘代芳基；
    Ar1和Ar2相同或不同，且各自独立地为碳原子数为6-30的取代或未取代的芳基、碳原子数为5-30的取代或未取代的杂芳基；
    各L独立地选自碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基，n表示L的个数，且n选自1或2，当n为2时，各L相同或不同；
    L1和L2相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为5-30的取代或未取代的亚杂芳基；
    L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、卤素基团、氰基、碳原子数为1-10的烷基、碳原子数为6-18的芳基、碳原子数为5-18的杂芳基、碳原子数为1-10的氘代烷基、碳原子数为1-10的卤代烷基或碳原子数为3-12的三烷基硅基；在Ar1和Ar2中，任选地，任意两个相邻的取代基形成碳原子数为3-15的饱和或不饱和环。
  2. 根据权利要求1所述的含氮化合物，其中，基团A选自氘取代或未取代的苯基、氘取代或未取代的萘基、氘取代或未取代的联苯基。
  3. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2相同或不同，且各自独立地为碳原子数为6-25的取代或未取代的芳基、碳原子数为12-25的取代或未取代的杂芳基；
    可选地，Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的氘代烷基、碳原子数为1-5的卤代烷基或碳原子数为3-7的三烷基硅基；任选地，在Ar1和Ar2中，任意两个相邻的取代基形成碳原子数为5-15的饱和或不饱和环。
  4. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芴基、取代或未取代的三亚苯基、取代或未取代的吡啶基、取代或未取代的二苯并呋喃基、取代或取代的二苯并噻吩基、取代或未取代的咔唑基；
    可选地，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、二苯并噻吩基、二苯并呋喃基、咔唑基、三氘代甲基、三氟甲基或三甲基硅基；任选地，Ar1和Ar2中，任意两个相邻的取代基形成苯环、环戊烷、环己烷或芴环。
  5. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2各自独立地选自取代或未取代的基团V，未取代的基团V选自以下基团：

    取代的基团V中具有一个或两个以上取代基，各取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、三氘代甲基、三氟甲基、苯基、萘基或吡啶基。
  6. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2各自独立地选自以下基团所组成的组：
  7. 根据权利要求1所述的含氮化合物，其中，各L独立地为碳原子数为6-15的取代或未取代的亚芳基，碳原子数为10-18的取代或未取代的亚杂芳基；
    L1和L2相同或不同，且各自独立地选自单键、碳原子数为6-18的取代或未取代的亚芳基、碳原子数为10-18的取代或未取代的亚杂芳基；
    可选地，L、L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、碳原子数为1-4的烷基或碳原子数为6-10的芳基。
  8. 根据权利要求1所述的含氮化合物，其中，各L独立地选自取代或未取代的基团W，L1和L2各自独立地选自单键、取代或未取代的基团W，未取代的基团W选自以下基团：
    取代的基团W中具有一个或两个以上取代基，各取代基独立地选自氘、氟、氰基、碳原子数为1-4的烷基、苯基、三甲基硅基、三氘代甲基或三氟甲基。
  9. 根据权利要求1所述的含氮化合物，其中，各L独立地选自以下基团所组成的组：
    可选地，L1和L2各自独立地选自单键和以下基团所组成的组：
  10. 根据权利要求1所述的含氮化合物，
    各自独立地选自以下基团组成的组：
  11. 根据权利要求1所述的含氮化合物，其中，所述含氮化合物选自如下化合物组成的组：








  12. 一种电子元件，其包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含权利要求1-11中任意一项所述的含氮化合物。
  13. 根据权利要求12所述的电子元件，其中，所述功能层包括空穴传输层，所述空穴传输层包含所述含氮化合物；
    可选地，所述电子元件选自有机电致发光器件或光电转换器件。
  14. 根据权利要求12所述的电子元件，其中，所述电子元件为有机电致发光器件，所述空穴传输层包括层叠设置的第一空穴传输层和第二空穴传输层，且相对所述第二空穴传输层，所述第一空穴传输层更靠近所述阳极；所述第二空穴传输层包含所述含氮化合物。
  15. 一种电子装置，包括权利要求12-14中任意一项所述的电子元件。
PCT/CN2023/094373 2022-08-17 2023-05-15 含氮化合物、电子元件和电子装置 WO2024037073A1 (zh)

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