WO2024055658A1 - 含氮化合物和电子元件及电子装置 - Google Patents

含氮化合物和电子元件及电子装置 Download PDF

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WO2024055658A1
WO2024055658A1 PCT/CN2023/100810 CN2023100810W WO2024055658A1 WO 2024055658 A1 WO2024055658 A1 WO 2024055658A1 CN 2023100810 W CN2023100810 W CN 2023100810W WO 2024055658 A1 WO2024055658 A1 WO 2024055658A1
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carbon atoms
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nitrogen
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刘文强
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陕西莱特光电材料股份有限公司
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • 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
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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
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    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • 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
    • H10K85/50—Organic perovskites; Hybrid organic-inorganic perovskites [HOIP], e.g. CH3NH3PbI3
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present application belongs to the field of organic electroluminescent materials, and specifically relates to 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.
  • organic electroluminescent diodes Compared with inorganic luminescent materials, organic electroluminescent diodes 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. Due to these advantages, 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 organic light-emitting layer, an electron transport 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 organic light-emitting layer to emit light.
  • OLED display technology has been applied in smartphones, tablets and other fields, and will further expand to large-size applications such as TVs.
  • the current efficiency, service life and other properties of OLED devices Still needs further improvement.
  • Research on improving the performance of OLED light-emitting devices includes: reducing the operating voltage of the device, improving the current efficiency of the device, and increasing the service life of the device.
  • OLED optoelectronic functional materials to create higher-performance OLED functional materials.
  • the purpose of this application is to provide a nitrogen-containing compound and electronic components and electronic devices. Using the nitrogen-containing compound in an organic electroluminescent device can improve the performance of the device.
  • this application provides a nitrogen-containing compound having a structure shown in Formula 1 below:
  • Ar 1 and Ar 2 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group with 6 to 40 carbon atoms, and a substituted or unsubstituted heteroaryl group with 3 to 40 carbon atoms;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted arylene group with 3 to 30 carbon atoms.
  • the substituents in Ar 1 , Ar 2 , L 1 and L 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, 1 carbon atom ⁇ 10 haloalkyl groups, deuterated alkyl groups with 1 to 10 carbon atoms, aryl groups with 6 to 18 carbon atoms, Deuterated aryl group with 6 to 18 carbon atoms, heteroaryl group with 5 to 18 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms or trialkylsilyl group with 3 to 12 carbon atoms ;
  • any two adjacent substituents form a 3 to 15-membered saturated or unsaturated ring;
  • R 1 and R 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 4 carbon atoms, halogenated alkyl group with 1 to 4 carbon atoms, and Deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 7 carbon atoms, aryl group with 6 to 18 carbon atoms, deuterated aryl group with 6 to 18 carbon atoms, and A heteroaryl group with 5 to 18 carbon atoms or a cycloalkyl group with 3 to 10 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 1 is greater than 1, each R 1 is the same or different;
  • n 2 represents the number of R 2 , n 2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 2 is greater than 1, each R 2 is the same or different.
  • the present application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound described in the first aspect of the present application.
  • the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
  • the nitrogen-containing compound of the present application is a triarylamine compound with a benzene ring core.
  • the introduction of two naphthyl structures at adjacent positions can adjust the three-dimensional configuration of the entire molecule and increase the glass transition temperature of the compound.
  • the two adjacent naphthyl structures enable the compound to have a deeper HOMO energy level and a higher LUMO energy level.
  • the compound can be used as a light-emitting auxiliary layer (i.e., the second hole transport layer) of the OLED device in conjunction with the adjacent functional layer. It has better interface performance when paired with it, and can also maintain high hole migration efficiency.
  • the crystallinity of the ortho-bis-naphthyl-substituted compound is reduced, and the film-forming property is improved, making the device more stable.
  • Using the nitrogen-containing compound of the present application in an OLED device can further improve the current efficiency and service life of the device while maintaining a lower driving voltage of the 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 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 diagram of a second electronic device according to an embodiment of the present application.
  • a first aspect of the application provides a nitrogen-containing compound having a structure shown in Formula 1 below:
  • Ar 1 and Ar 2 are the same or different, and each is independently selected from a substituted or unsubstituted aryl group with 6 to 40 carbon atoms, a carbon Substituted or unsubstituted heteroaryl group with 3 to 40 atoms;
  • L 1 and L 2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted arylene group with 3 to 30 carbon atoms.
  • the substituents in Ar 1 , Ar 2 , L 1 and L 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, 1 carbon atom ⁇ 10 haloalkyl group, deuterated alkyl group with 1 to 10 carbon atoms, aryl group with 6 to 18 carbon atoms, deuterated aryl group with 6 to 18 carbon atoms, 5 to 18 carbon atoms A heteroaryl group, a cycloalkyl group with 3 to 10 carbon atoms, or a trialkylsilyl group with 3 to 12 carbon atoms; optionally, any two adjacent substituents form a saturated 3-15-membered or unsaturated ring;
  • R 1 and R 2 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 4 carbon atoms, halogenated alkyl group with 1 to 4 carbon atoms, and Deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 7 carbon atoms, aryl group with 6 to 18 carbon atoms, deuterated aryl group with 6 to 18 carbon atoms, and A heteroaryl group with 5 to 18 carbon atoms or a cycloalkyl group with 3 to 10 carbon atoms;
  • n 1 represents the number of R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 1 is greater than 1, each R 1 is the same or different;
  • n 2 represents the number of R 2 , n 2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 2 is greater than 1, each R 2 is the same or different.
  • each... is independently selected from and “... each is independently selected from” are interchangeable and should be understood in a broad sense. They can refer to the same in different groups.
  • the specific options expressed by the symbols do not affect each other. It can also be expressed that in the same group, the specific options expressed by the same symbols do not affect each other.
  • each q is independently selected from 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 adjacent substituents can form a ring but do not have to form a ring, including: the scenario where two adjacent substituents form a ring. 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, halogen group, cyano group, heteroaryl group, aryl group, alkyl group, haloalkyl group, deuterated alkyl group, cycloalkyl group, trialkylsilyl group, deuterated aromatic group Key et al.
  • the "substituted" functional group can be substituted by 1 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 together with the atoms; 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.
  • Ring in this application includes saturated rings and unsaturated rings; saturated rings include cycloalkyl and heterocycloalkyl, and unsaturated rings include cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.
  • a ring system formed by n atoms is an n-membered ring.
  • phenyl is a 6-membered aryl group
  • fluorene ring is a 13-membered ring
  • cyclohexane is a 6-membered ring
  • adamantane is a 10-membered ring.
  • any two adjacent substituents form a 3-15 membered saturated or unsaturated ring
  • the ring formed is a saturated ring or an unsaturated ring, where the saturated ring is, for example, cyclopentane cyclohexane
  • Unsaturated rings such as benzene ring, naphthalene ring or fluorene ring
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group may be a monocyclic aryl group (e.g. phenyl) or polycyclic aryl, in other words, the aryl group can be a single-ring aryl group, a fused-ring aryl group, two or more single-ring aryl groups conjugated through a carbon-carbon bond, a conjugated through a carbon-carbon bond Connected single-ring aryl groups 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. It should be noted that both biphenyl and fluorenyl groups are regarded as aryl groups in this application.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthene base, 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 than two hydrogen atoms in the aryl group substituted by deuterium, halogen group, cyano group, aryl group, heteroaryl group, alkyl group, cycloalkyl group, deuterated group, etc.
  • Alkyl, deuterated aryl, trialkylsilyl and other groups are substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuryl-substituted phenyl, dibenzothienyl-substituted phenyl, and the like.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with a carbon number of 18 refers to the aryl group and the substituted aryl group.
  • the total number of carbon atoms in the base is 18.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1 or more, such as 1, 2, 3, 4, 5, 6 or more heteroatoms in the ring.
  • the heteroatom may 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 include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine Aldyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine base, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thieno Thienyl, benzofuranyl,
  • 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 than two hydrogen atoms in the heteroaryl group substituted by, for example, deuterium, fluorine, cyano, aryl, heteroaryl, alkyl, cycloalkyl, deuterated Alkyl, deuterated aryl, trialkylsilyl and other groups are substituted.
  • 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.
  • 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') passes through a benzene ring from one side to the middle
  • the extended non-positioned bond is connected to other positions of the molecule, and its meaning includes any possible connection method as 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 halogen group includes bromine, fluorine, chlorine, iodine, etc., with fluorine being preferred.
  • the number of carbon atoms of the alkyl group having 1 to 10 carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • Specific examples of 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 number of carbon atoms of the aryl group as a substituent may be 6 to 18, and the number of carbon atoms is, for example, 6, 10, 12, 14, 18, etc.
  • Specific examples of the aryl group as a substituent include but are not limited to , phenyl, naphthyl, biphenyl.
  • the carbon number of the heteroaryl group as a substituent can be 5 to 18, for example, the carbon number is 5, 8, 9, 10, 12, 18, etc.
  • Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, etc.
  • the number of carbon atoms of the cycloalkyl group as a substituent may be 3 to 10, and the number of carbon atoms is, for example, 3, 5, 6, 8, 10, etc.
  • Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
  • the number of carbon atoms of the trialkylsilyl group as a substituent may be 3 to 12, and the number of carbon atoms may be, for example, 3, 5, 6, 8, 10, etc.
  • Specific examples of trialkylsilyl include, but are not limited to: trimethylsilyl.
  • the number of carbon atoms of the deuterated alkyl group as a substituent may be 1 to 10, and is preferably 1 to 4.
  • Specific examples of deuterated alkyl groups include, but are not limited to: trideuterated methyl.
  • the number of carbon atoms of the haloalkyl group as a substituent may be 1 to 10, preferably 1 to 4.
  • Specific examples of haloalkyl groups include, but are not limited to: trifluoromethyl.
  • the number of carbon atoms of the deuterated aryl group as a substituent may be 6 to 18, preferably 6 to 12.
  • deuterated aryl include, but are not limited to, pentadeuterated phenyl
  • the structure of the nitrogen-containing compound can be selected from the group consisting of Formula 1-1, Formula 1-2, Formula 2-1 or Formula 2-2:
  • R 1 and R 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trideuterated methyl, Methylsilyl, phenyl, naphthyl, biphenyl, pentadeuterophenyl, dibenzofuryl, dibenzothienyl, cyclopentyl or cyclohexyl.
  • R 1 and R 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteratedmethyl or phenyl.
  • Each is independently selected from the group consisting of:
  • L 1 and L 2 are each independently selected from single bonds, and the number of carbon atoms 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, 30 substituted or unsubstituted arylene groups, with carbon atoms of 3, 4, 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, 30 substituted or unsubstituted heteroarylene groups.
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms. base.
  • L 1 and L 2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
  • 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 phenanthrene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted dibenzofurylene group, substituted or unsubstituted dibenzothienylene group, substituted or unsubstituted carbazolylene group.
  • the substituents in L 1 and L 2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and Haloalkyl group with 1 to 4 carbon atoms, deuterated alkyl group with 1 to 4 carbon atoms, aryl group with 6 to 12 carbon atoms, deuterated aryl group with 6 to 12 carbon atoms, deuterated aryl group with 5 to 12 carbon atoms. 12 heteroaryl groups or trialkylsilyl groups with 3 to 7 carbon atoms.
  • the substituents in L 1 and L 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl , phenyl or naphthyl.
  • 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 or the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of carbon atoms with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 substituted or unsubstituted aryl groups, number of carbon atoms for 3, 4, 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, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 substituted or unsubstituted heteroaryl groups.
  • Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted aryl group with 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group with 12 to 24 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 phenanthrenyl, Substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or Unsubstituted carbazolyl.
  • Ar 1 is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl.
  • Ar 1 is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, the nitrogen-containing compound of the present application
  • the molecular spatial configuration is more three-dimensional, which can increase the T1 energy level and effectively block the diffusion of excitons.
  • the service life of the device can be significantly improved.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, and Deuterated alkyl group with 1 to 4 carbon atoms, aryl group with 6 to 12 carbon atoms, heteroaryl group with 5 to 12 carbon atoms, cycloalkyl group with 5 to 10 carbon atoms or 3 carbon atoms ⁇ 7 trialkylsilyl groups; optionally, any two adjacent substituents form a 5-15 membered saturated or unsaturated ring.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl base, trifluoromethyl, trideuteratedmethyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or trimethylsilyl; optionally, any two adjacent substituents form Benzene ring, cyclopentane cyclohexane or fluorene ring
  • Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of:
  • the substituents in the substituted group W are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteratedmethyl, trimethylsilyl group, phenyl or naphthyl, when the number of substituents is greater than 1, each substituent may be the same or different.
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 is selected from the following groups:
  • the organic electroluminescent device when used as the second hole transport layer of the organic electroluminescent device, the organic electroluminescent device has higher life.
  • the nitrogen-containing compound is selected from the group consisting of:
  • a second aspect of the application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer includes the nitrogen-containing compound described in the first aspect of the application.
  • the functional layer includes a hole transport layer containing the nitrogen-containing compound of the present application.
  • the electronic component may be an organic electroluminescent device or a photoelectric conversion device.
  • 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 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
  • the hole transport layer 320 contains the nitrogen-containing compound of the present application.
  • the hole transport layer 320 includes a stacked first hole transport layer 321 and a second hole transport layer 322, and the first hole transport layer 321 is closer to the second hole transport layer 322. the anode.
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or 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 SnO2 :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 material of the first hole transport layer 321 can be selected from various existing hole transport layer materials, which is not particularly limited in this application.
  • the hole transport layer material can be selected from carbazole polymers, carbazole-linked aromatic amine compounds, dibenzofuran-linked aromatic amine compounds, substituted fluorenyl-linked triarylamine compounds, or other types of compounds, specifically Examples include, but are not limited to, at least one 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 may be composed of a single light-emitting material, or may include a host material and a guest material (also called a "dopant").
  • the organic light-emitting layer 330 is composed of 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 main 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. This application does not Make special restrictions.
  • the host material is selected from one or more than two of the following compounds:
  • the host material is CPB.
  • 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 is Ir(piq) 2 (acac).
  • the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include the nitrogen-containing compound of the present application and optionally one or more other electron transport materials.
  • the other electron transport materials can usually include metal complexes. and/or nitrogen-containing heterocyclic derivatives, wherein the metal complex material can be selected from LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative can be a nitrogen-containing six-membered ring or An aromatic ring with a five-membered ring skeleton, a condensed aromatic ring compound with a nitrogen-containing six-membered ring or a five-membered ring skeleton, for example, DBimiBphen.
  • electron transport layer 340 is composed of LiQ and DBimiBphen.
  • the cathode 200 includes a cathode material, which is a material with a small work function that facilitates the injection of electrons into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or 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 is also provided between the anode 100 and the hole transport layer 320 to enhance the hole injection layer 310 .
  • 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 m-MTDATA.
  • an electron injection layer 350 is also provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include 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.
  • electron injection layer 350 contains LiQ.
  • the organic electroluminescent device may be a blue light device, a red light device or a green light device, preferably a red light device.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 that are stacked in sequence.
  • the hole transport layer 320 contains the nitrogen-containing compound of the present application.
  • the photoelectric conversion device is a solar cell, such as an organic thin film solar cell.
  • a third aspect of the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 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.
  • the organic phase was dried using anhydrous magnesium sulfate. After filtration, the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product.
  • the crude product was purified by silica gel column chromatography using a methylene chloride/n-heptane system to obtain a white solid IM. -e-1-1 (49.04g, yield 49%).
  • the organic phase was dried using anhydrous magnesium sulfate. After filtration, the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product.
  • the crude product was purified by silica gel column chromatography using a methylene chloride/n-heptane system to obtain a white solid IM. -g-1 (35.15g, yield 68%).
  • the thickness is The ITO/Ag/ITO glass substrate is cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and the photolithography process is used to prepare it into an experimental substrate with anode and insulating layer patterns. First, use ultrapure water and isopropyl alcohol to clean the surface. Clean, clean the contaminants on the surface of the substrate; then use O2 : N2 plasma gas to treat the surface of the substrate.
  • m-MTDATA was vacuum evaporated on the experimental substrate (anode) to form a thickness of hole injection layer, and vacuum evaporate NPB (i.e. HT-1) on the hole injection layer to form a thickness of the first hole transport layer.
  • NPB i.e. HT-1
  • Compound A-1-3 is vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • CBP and Ir(piq) 2 (acac) were co-evaporated with a film thickness ratio of 100:3 to form a layer with a thickness of organic light-emitting layer.
  • DBimiBphen and LiQ were co-evaporated at a weight ratio of 1:1 to form a layer with a thickness of electron transport layer;
  • LiQ is evaporated to form a layer with a thickness of electron injection layer.
  • magnesium (Mg) and silver (Ag) were mixed at an evaporation rate ratio of 1:9, and vacuum evaporated on the electron injection layer to form a thickness of the cathode.
  • CPL organic covering layer
  • the second hole transport layer was prepared using the same method as in Example 1, except that the compounds in Table 6 (column "HTL-2") were used instead of the compounds A-1-3 in Example 1. Organic electroluminescent devices.
  • An organic electroluminescent device was manufactured using the same method as in Example 1, except that when preparing the second hole transport layer, Compound A, Compound B and Compound C were used instead of Compound A-1-3 in Example 1. .
  • Performance tests were performed on the organic electroluminescent devices prepared in Examples 1-44 and Comparative Examples 1-3, and the results are shown in Table 6. Among them, the IVL (working voltage, current efficiency) performance is the test result under the current density of 10mA/ cm2 , and the T95 life is the test result under the current density of 20mA/ cm2 .

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Abstract

本申请属于有机材料技术领域，提供一种含氮化合物和电子元件及电子装置。该含氮化合物的结构如式1所示，所述含氮化合物能够提高电子元件的性能。

Description

含氮化合物和电子元件及电子装置
相关申请的交叉引用
本申请要求于2022年9月14日递交的申请号为CN202211119275.8的中国专利申请和2022年11月03日递交的申请号为CN202211370565.X的中国专利申请的优先权，上述中国专利申请的全部内容通过引用并入本申请中。
技术领域
本申请属于有机电致发光材料领域，具体地涉及一种含氮化合物和电子元件及电子装置。
背景技术
有机电致发光器件(OLED)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。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。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、有机发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，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，进而使得有机发光层对外发光。
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展，但是，和实际的产品应用要求相比，OLED器件的电流效率、使用寿命等性能还需要进一步提升。对于OLED发光器件提高性能的研究包括：降低器件的工作电压，提高器件的电流效率，提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能OLED的功能材料。
发明内容
本申请的目的在于提供一种含氮化合物和电子元件及电子装置，将该含氮化合物用于有机电致发光器件能够改善器件的性能。
第一方面，本申请提供一种含氮化合物，其具有如下式1所示的结构：
其中，Ar1和Ar2相同或不同，且各自独立地选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；
L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar1、Ar2、L1和L2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1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为6～18的芳基、 碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基、碳原子数为3～10的环烷基或碳原子数为3～12的三烷基硅基；任选地，任意两个相邻的取代基形成3～15元的饱和或不饱和环；
R1和R2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1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～18的芳基、碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基或碳原子数为3～10的环烷基；
n1表示R1的个数，n1选自0、1、2、3、4、5、6或7，且当n1大于1时，各R1相同或不同；
n2表示R2的个数，n2选自0、1、2、3、4、5、6或7，且当n2大于1时，各R2相同或不同。
第二方面，本申请提供一种电子元件，包括阳极、阴极以及设置在所述阳极和阴极之间的功能层，其中，所述功能层包含本申请第一方面所述的含氮化合物。
第三方面，本申请提供一种电子装置，包括本申请第二方面所述的电子元件。
本申请的含氮化合物为一种具有苯环核心的三芳胺类化合物，在该苯环的相邻位置(即1,2号位)引入两个萘基类结构，可调整整个分子的立体构型，提升化合物的玻璃化温度。另外，相邻的两个萘基类结构使化合物具有更深的HOMO能级和较高的LUMO能级，将化合物作为OLED器件的发光辅助层(即第二空穴传输层)与相邻功能层搭配时有更好的界面性能，并且还能保持较高的空穴迁移效率。此外，邻位双萘基取代的化合物结晶性降低，成膜性得到提升，使器件具有较高的稳定性。将本申请的含氮化合物用于OLED器件在维持器件具有较低驱动电压的情况下，能进一步提高器件的电流效率和使用寿命。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的示意图。
图3是本申请一种实施方式的光电转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示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；320、空穴传输层；321、第一空穴传输层；322、第二空穴传输层；330、有机发光层；340、电子传输层；350、电子注入层；360、光电转化层；400、第一电子装置；500、第二电子装置。
具体实施方式
以下结合附图对本申请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申请，并不用于限制本申请。
本申请的第一方面提供一种含氮化合物，其具有如下式1所示的结构：
式1中，Ar1和Ar2相同或不同，且各自独立地选自碳原子数为6～40的取代或未取代的芳基、碳 原子数为3～40的取代或未取代的杂芳基；
L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
Ar1、Ar2、L1和L2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1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为6～18的芳基、碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基、碳原子数为3～10的环烷基或碳原子数为3～12的三烷基硅基；任选地，任意两个相邻的取代基形成3～15元的饱和或不饱和环；
R1和R2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1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～18的芳基、碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基或碳原子数为3～10的环烷基；
n1表示R1的个数，n1选自0、1、2、3、4、5、6或7，且当n1大于1时，各R1相同或不同；
n2表示R2的个数，n2选自0、1、2、3、4、5、6或7，且当n2大于1时，各R2相同或不同。
本申请中，所采用的描述方式“各……独立地选自”和“……各自独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。举例来讲，其中，各q独立地选自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”可以相同或不同，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情况。例如，“任选地，任意两个相邻的取代基形成环”意味着任意两个相邻的取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
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、杂芳基、芳基、烷基、卤代烷基、氘代烷基、环烷基、三烷基硅基、氘代芳基等。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一起形成螺环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
本申请中的“环”包含饱和环、不饱和环；饱和环即环烷基、杂环烷基，不饱和环包括环烯基、杂环烯基、芳基和杂芳基。在本申请中，n个原子形成的环体系，即为n元环。例如，苯基为6元芳基；芴环属于13元环，环己烷属于6元环，金刚烷属于10元环。
在本申请中，“任意两个相邻的取代基形成3～15元的饱和或不饱和环”中，所形成的环是饱和环或不饱和环，其中，饱和环例如为环戊烷环己烷不饱和环例如为苯环、萘环或芴环
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。需要说明地是，联苯基、芴基在本申请中均视为芳基。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、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的氢原子被诸如氘、卤素基团、氰基、芳基、杂芳基、烷基、环烷基、氘代烷基、氘代芳基、三烷基硅基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩基取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
在本申请中，杂芳基是指环中包含1个或多个，例如1个、2个、3个、4个、5个、6个或更多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，杂芳基包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-苯基咔唑基、N-吡啶基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的氢原子被诸如氘、氟、氰基、芳基、杂芳基、烷基、环烷基、氘代烷基、氘代芳基、三烷基硅基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
本申请中，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：
在本申请中，卤素基团包括溴、氟、氯、碘等，优选为氟。
在本申请中，碳原子数为1～10的烷基的碳原子数可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1～10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
在本申请中，作为取代基的芳基的碳原子数可以为6～18，碳原子数例如为6、10、12、14、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。
在本申请中，作为取代基的杂芳基的碳原子数可以为5～18，碳原子数例如为5、8、9、10、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。
在本申请中，作为取代基的环烷基的碳原子数可以为3～10，碳原子数例如为3、5、6、8、10等。环烷基的具体实例包括但不限于，环戊基、环己基等。
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，碳原子数例如为3、5、6、8、10等。三烷基硅基的具体实例包括但不限于：三甲基硅基。
本申请中，作为取代基的氘代烷基的碳原子数可以为1～10，优选为1～4。氘代烷基的具体实例包括但不限于：三氘代甲基。
本申请中，作为取代基的卤代烷基的碳原子数可以为1～10，优选为1～4。卤代烷基的具体实例包括但不限于：三氟甲基。
本申请中，作为取代基的氘代芳基的碳原子数可以为6～18，优选为6～12。氘代芳基的具体实例包括但不限于五氘代苯基
本申请中，所述含氮化合物的结构可以选自式1-1、式1-2、式2-1或式2-2所组成的组：
在一种实施方式中，R1和R2各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基、萘基、联苯基、五氘代苯基、二苯并呋喃基、二苯并噻吩基、环戊烷基或环己烷基。
进一步可选地，R1和R2各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基或苯基。
在一种实施方式中，式1中的分别独立地选自以下基团所组成的组：
可选地，分别独立地选自以下基团所组成的组：
本申请中，L1和L2各自独立地选自单键，碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30的取代或未取代的亚芳基，碳原子数为3、4、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、30的取代或未取代的亚杂芳基。
可选地，L1和L2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12～18的取代或未取代的亚杂芳基。
进一步可选地，L1和L2各自独立地选自单键、碳原子数为6～12的取代或未取代的亚芳基。
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、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚咔唑基。
可选地，L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为 1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为6～12的芳基、碳原子数为6～12的氘代芳基、碳原子数为5～12的杂芳基或碳原子数为3～7的三烷基硅基。
进一步可选地，L1和L2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、苯基或萘基。
在一种实施方式中，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和L2各自独立地选自单键或以下基团所组成的组：
在本申请中，Ar1和Ar2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、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40的取代或未取代的芳基，碳原子数为3、4、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、30、31、32、33、34、35、36、37、38、39、40的取代或未取代的杂芳基。
在一种实施方式中，Ar1和Ar2各自独立地选自碳原子数为6～25的取代或未取代的芳基、碳原子数为12～24的取代或未取代的杂芳基。
在一种实施方式中，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、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三联苯基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基。
在一种实施方式中，Ar1选自取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基。
当Ar1选自取代或未取代的芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基时，本申请含氮化合物分子空间构型更立体，从而可以提高T1能级，有效阻挡激子的扩散，用作有机电致发光器件的第二空穴传输层时，显著提高器件的使用寿命。
可选地，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、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5～10的环烷基或碳原子数为3～7的三烷基硅基；任选地，任意两个相邻的取代基形成5～15元的饱和或不饱和环。
进一步可选地，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁 基、三氟甲基、三氘代甲基、苯基、萘基、二苯并呋喃基、二苯并噻吩基或三甲基硅基；任选地，任意两个相邻的取代基形成苯环、环戊烷环己烷或芴环
在一种实施方式中，Ar1和Ar2各自独立地选自取代或未取代的基团W，未取代的基团W选自以下基团所组成的组：
取代的基团W中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基或萘基，当取代基的个数大于1时，各取代基相同或不同。
可选地，Ar1和Ar2各自独立地选自以下基团所组成的组：
进一步可选地，Ar1和Ar2各自独立地选自以下基团所组成的组：

在一种优选的实施方式中，Ar1选自以下基团：
本申请含氮化合物中Ar1基团选自氘取代芳基或氘取代的杂芳基时，用作有机电致发光器件的第二空穴传输层时，有机电致发光器件具有更高的寿命。
在一种实施方式中，相同或不同，且各自独立地选自以下基团所组成的组：
在一种实施方式中，相同或不同，且各自独立地选自以下基团所组成的组：
在一种优选的实施方式中，选自以下基团组成的组：

选自以下基团组成的组：
可选地，所述含氮化合物选自以下化合物所组成的组：








本申请第二方面提供一种电子元件，包括阳极、阴极，以及设置在所述阳极与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。
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的含氮化合物。
本申请中，所述电子元件可以为有机电致发光器件或光电转化器件。
按照一种具体的实施方式，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，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，且相对第二空穴传输层322，第一空穴传输层321更靠近所述阳极。
本申请中，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，第一空穴传输层321的材料可以选自现有的各种空穴传输层材料，本申请对此没有特别限定。所述穴传输层材料、可以选自咔唑多聚体、咔唑连接芳胺类化合物、二苯并呋喃连接芳胺类化合物、取代的芴基连接三芳胺类化合物或者其他类型的化合物，具体实例包括但不限于以下化合物中的至少一种：
在一种具体的实施方式中，第一空穴传输层321的材料为HT-1。
可选地，第二空穴传输层322包含本申请的含氮化合物。
有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料(也称“掺杂剂”)。可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330内复合而形成激子，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，本申请对此不做特殊的限制。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，所述主体材料为CPB。
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，所述客体材料为Ir(piq)2(acac)。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括本申请的含氮化合物和可选的一种或者多种其他电子传输材料，其他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，例如为DBimiBphen。
在一种具体的实施方式中，电子传输层340由LiQ和DBimiBphen组成。
本申请中，阴极200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和空穴传输层320之间还设置有空穴注入层310，以增强向空穴 传输层320注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。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为m-MTDATA。
可选地，如图1所示，在阴极200和电子传输层340之间还设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。
在一种具体的实施方式中，电子注入层350包含LiQ。
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，优选为红光器件。
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，光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、光电转化层360、电子传输层340和阴极200。其中，所述空穴传输层320包含本申请的含氮化合物。
可选地，光电转化器件为太阳能电池，例如为有机薄膜太阳能电池。
本申请的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，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。
1、IM-a-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入Sub 1(3-氯2-溴1-碘苯，100.0g，315.1mmol)、Sub 2(2-萘硼酸，113.81g，661.7mmol)、双三苯基膦二氯化钯(Pd(PPh3)2Cl2，2.2g，3.15mmol)、碳酸钾(K2CO3，174.21g，1260.44mmol)，并加入乙二醇二甲醚(DME，1600mL)和水(400mL)的混合溶剂。开启搅拌，升温至78℃-80℃反应48h。反应结束后，冷却至室温。反应液水洗后分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体IM-a-1(74.73g，收率65％)。
参照IM-a-1的方法合成表1所列的中间体，不同之处在于，使用原料A替代原料Sub 2，其中所使用的主要原料、制备的中间体及其收率如表1所示。
表1
2、IM-e-1-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入Sub 1(100.0g，315.1mmol)、Sub 2(54.20g，315.1mmol)、双三苯基膦二氯化钯(1.11g，1.58mmol)、碳酸钾(108.88g，787.78mmol)，并加入乙二醇二甲醚(800mL)和水(200mL)的混合溶剂。开启搅拌，升温至70℃-75℃反应48h。反应结束后，冷却至室温。反应液水洗后分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体IM-e-1-1(49.04g，收率49％)。
参照IM-e-1-1的方法合成表2所列的中间体，不同之处在于，使用原料B替代Sub 2，其中所使用的主要原料、制备的中间体及其收率如表2所示。
表2
3、IM-g-1的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入IM-e-1-1(45.00g，141.68mmol)、Sub 3(24.37g，141.68mmol)、双三苯基膦二氯化钯(0.99g，1.42mmol)、碳酸钾(48.95g，354.21mmol)，并加入乙二醇二甲醚(360mL)和水(90mL)的混合溶剂。开启搅拌，升温至75℃-78℃反应12h。反应结束后，冷却至室温。反应液水洗后分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体IM-g-1(35.15g，收率68％)。
参照IM-g-1的方法合成表3所列的中间体，不同之处在于，使用原料C替代IM-e-1-1，使用原料D替代Sub 3，其中所使用的主要原料、制备的中间体及其收率如表3所示。
表3

4、化合物A-1-3的合成
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.200L/min)置换15min，依次加入IM-a-1(15g，41.11mmol)、4-氨基联苯(6.96g，41.11mmol)、三(二亚苄基丙酮)二钯(Pd2(dba)3，0.37g，0.41mmol)、2-二环己基膦-2’,4’,6’-三异丙基联苯(XPhos，0.39g，0.82mmol)、叔丁醇钠 (tBuONa，5.93g，61.66mmol)和甲苯(PhMe，150mL)，升温至回流反应4h。反应结束后，冷却至室温。有机相使用水洗，分出有机相，加入无水硫酸镁干燥，过滤后将滤液减压蒸馏除去溶剂得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体IMA(14.93g，收率73％)。
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入IM A(10g，20.09mmol)、4-溴联苯(4.68g，20.09mmol)、三(二亚苄基丙酮)二钯(0.184g，0.20mmol)、2-二环己基膦-2,6-二甲氧基联苯(S-Phos，0.165g，0.40mmol)、叔丁醇钠(2.90g，30.14mmol)和甲苯(100mL)，升温至回流反应30h。反应结束后，冷却至室温。有机相水洗后，分液，分出的有机相加入无水硫酸镁干燥，过滤后将滤液减压蒸馏除去溶剂得到粗品；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到为白色固体的化合物A-1-3(6.65g，收率51％)，质谱(m/z)＝650.3[M+H]+。
参照化合物A-1-3的方法合成下表4所列的化合物，不同之处在于，使用原料E代替IM-a-1，使用原料F代替4-氨基联苯，使用原料G代替4-溴联苯，其中所采用的主要原料、制备的化合物及其最终收率和质谱如表4所示。
表4






部分化合物核磁数据如表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：红色有机电致发光器件的制作
将厚度依次为的ITO/Ag/ITO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)上真空蒸镀m-MTDATA以形成厚度为的空穴注入层，并且在空穴注入层上真空蒸镀NPB(即HT-1)，以形成厚度为的第一空穴传输层。
在第一空穴传输层上真空蒸镀化合物A-1-3，形成厚度为的第二空穴传输层。
第二空穴传输层上，将CBP和Ir(piq)2(acac)以100∶3的膜厚比共同蒸镀，形成厚度为的有机发光层。
在有机发光层上，将DBimiBphen和LiQ以1∶1的重量比进行共同蒸镀，形成厚度为的电子传输层；
在电子传输层上，蒸镀LiQ以形成厚度为的电子注入层。然后，将镁(Mg)和银(Ag)以1:9的蒸镀速率比进行混合，真空蒸镀在电子注入层上，形成厚度为的阴极。
最后，在上述阴极上蒸镀CP-1，形成厚度为的有机覆盖层(CPL)，从而完成有机电致发光器件的制造。
实施例2-44
除了在制备第二空穴传输层时，分别以表6中的化合物(“HTL-2”列)替代实施例1中的化合物A-1-3之外，采用与实施例1相同的方法制作有机电致发光器件。
比较例1-3
除了在制备第二空穴传输层时，分别使用化合物A、化合物B和化合物C替代实施例1中的化合物A-1-3之外，采用与实施例1相同的方法制造有机电致发光器件。
以上实施例和比较例中，制备有机电致发光器件时所使用的主要化合物的结构如下：
对实施例1-44和比较例1-3制备所得的有机电致发光器件进行性能测试，结果如表6所示。其中，IVL(工作电压、电流效率)性能是在10mA/cm2电流密度下的测试结果，T95寿命是20mA/cm2电流密度下的测试结果。
表6

根据上述表6的结果可知，相较于比较例1-3所制备的有机电致发光器件，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的实施例1-44的电流效率至少提高了12.5％，使用寿命至少提高了17.3％，并使器件兼具较低的工作电压。
以上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，可以对本申请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。

Claims (14)

  1. 含氮化合物，其特征在于，所述含氮化合物具有如下式1所示的结构：
    其中，Ar1和Ar2相同或不同，且各自独立地选自碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；
    L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；
    Ar1、Ar2、L1和L2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1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为6～18的芳基、碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基、碳原子数为3～10的环烷基或碳原子数为3～12的三烷基硅基；任选地，任意两个相邻的取代基形成3～15元的饱和或不饱和环；
    R1和R2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1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为3～7的三烷基硅基、碳原子数为6～18的芳基、碳原子数为6～18的氘代芳基、碳原子数为5～18的杂芳基或碳原子数为3～10的环烷基；
    n1表示R1的个数，n1选自0、1、2、3、4、5、6或7，且当n1大于1时，各R1相同或不同；
    n2表示R2的个数，n2选自0、1、2、3、4、5、6或7，且当n2大于1时，各R2相同或不同。
  2. 根据权利要求1所述的含氮化合物，其中，所述含氮化合物的结构选自式1-1、式1-2、式2-1或式2-2所组成的组：
    优选地，R1和R2各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基、萘基、联苯基、五氘代苯基、二苯并呋喃基、二苯并噻吩基、环戊烷基或环己烷基。
  3. 根据权利要求1所述的含氮化合物，其中，L1和L2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12～18的取代或未取代的亚杂芳基；
    优选地，L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为 1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为6～12的芳基、碳原子数为6～12的氘代芳基、碳原子数为5～12的杂芳基或碳原子数为3～7的三烷基硅基。
  4. 根据要求要求1所述的含氮化合物，其中，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、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚咔唑基；
    优选地，L1和L2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、苯基或萘基。
  5. 根据权利要求1所述的含氮化合物，其中，L1和L2各自独立地选自单键和以下基团所组成的组：
  6. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2各自独立地选自碳原子数为6～25的取代或未取代的芳基、碳原子数为12～24的取代或未取代的杂芳基；
    优选地，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、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5～10的环烷基或碳原子数为3～7的三烷基硅基；任选地，任意两个相邻的取代基形成5～15元的饱和或不饱和环。
  7. 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、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的三联苯基、取代或未取代的三亚苯基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基；
    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、异丙基、叔丁基、三氟甲基、三氘代甲基、苯基、萘基、二苯并呋喃基、二苯并噻吩基或三甲基硅基；任选地，任意两个相邻的取代基形成苯环、环戊烷、环己烷或芴环。
  8. 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W，未取代的基团W选自以下基团所组成的组：
    取代的基团W中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基、苯基或萘基，当取代基的个数大于1时，各取代基相同或不同。
  9. 根据权利要求1所述的含氮化合物，其中，Ar1和Ar2各自独立地选自以下基团所组成的组：

  10. 根据权利要求1所述的含氮化合物，其中，各自独立地选自以下基团所组成的组：
  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以下化合物所组成的组：








  12. 电子元件，包括阳极、阴极，以及设置在所述阳极和阴极之间的功能层，其特征在于，所述功能层包含权利要求1-11中任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；
    优选地，所述电子元件为有机电致发光器件或光电转化器件；
    更优选地，所述电子元件为有机电致发光器件，所述空穴传输层包括第一空穴传输层和第二空穴传输层，所述第一空穴传输层相对所述第二空穴传输层更靠近所述阳极，其中，所述第二空穴传输层包含所述含氮化合物。
  14. 电子装置，包括权利要求12或13所述的电子元件。
PCT/CN2023/100810 2022-09-14 2023-06-16 含氮化合物和电子元件及电子装置 WO2024055658A1 (zh)

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