WO2022083598A1 - 一种含氮化合物以及使用其的电子元件和电子装置 - Google Patents

一种含氮化合物以及使用其的电子元件和电子装置 Download PDF

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WO2022083598A1
WO2022083598A1 PCT/CN2021/124790 CN2021124790W WO2022083598A1 WO 2022083598 A1 WO2022083598 A1 WO 2022083598A1 CN 2021124790 W CN2021124790 W CN 2021124790W WO 2022083598 A1 WO2022083598 A1 WO 2022083598A1
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carbon atoms
substituted
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nitrogen
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French (fr)
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马天天
杨敏
南朋
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陕西莱特光电材料股份有限公司
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
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Definitions

  • the present application belongs to the technical field of organic materials, and specifically provides a nitrogen-containing compound and electronic components and electronic devices using the same.
  • Such electronic components usually include oppositely disposed cathodes and anodes, and functional layers disposed between the cathodes and the anodes.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • an organic electroluminescence device as an example, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence.
  • an electric field is generated between the two electrodes.
  • the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer, and the electrons and holes combine in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state to release energy to the outside, thereby causing the electroluminescent layer to emit light to the outside.
  • the purpose of the present 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 organic electroluminescent devices to improve the performance of organic electroluminescent devices performance.
  • a first aspect of the present application provides a nitrogen-containing compound, the nitrogen-containing compound has a structure shown in formula F-1:
  • L, L 1 and L 2 are the same or different from each other, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted group having 3 to 30 carbon atoms. the heteroarylene;
  • Ar 1 and Ar 2 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
  • Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;
  • R 1 , R 2 , R 3 and R 4 are the same or different from each other, and are independently selected from hydrogen, or a group represented by formula F-2, and one of R 1 , R 2 , R 3 and R 4 which is a group represented by formula F-2;
  • R 5 is selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, 6-30 substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • n 1 represents the number of R 5 , n 1 is 0, 1, 2, 3, 4 or 5;
  • the substituents in L, L 1 , L 2 , Ar 1 , Ar 2 , R 5 are each independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally by Aryl having 6 to 20 carbon atoms and 3 carbon atoms substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl A trialkylsilyl group of ⁇ 12, a triarylsilyl group of 18 to 24 carbon atoms, an alkyl group of 1 to 10 carbon atoms, a haloalkyl group of 1 to 10 carbon atoms, and 2 to 10 carbon atoms Alkenyl group of 6, alkynyl group of carbon number of 2 to 6, cycloalkyl group of carbon number of 3 to 10, heterocycloalkyl group of carbon number of 2 to 10, ring of carbon number of 5 to 10 Alkenyl group, heterocyclic alkeny
  • Substituents in Ar 3 are selected from deuterium, halogen group, cyano group, phenyl group.
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the nitrogen-containing element described in the first aspect of the present application compound;
  • the functional layer includes an electron blocking layer, and the electron blocking layer includes the nitrogen-containing compound.
  • a third aspect of the present application provides an electronic device, and the electronic device includes the electronic element described in the second aspect of the present application.
  • the nitrogen-containing compound of the present application has a molecular structure with a carbazole derivative as a parent nucleus and an aromatic amine group combined.
  • the compounds improve the stability and hole transport properties of the whole molecule through the synergistic effect of the parent core and surrounding hole transport groups.
  • the aromatic amine structure in the nitrogen-containing compound can improve the transport efficiency of holes in the device, block electrons in the light-emitting layer, and greatly improve the carrier recombination rate; and the carbazole structure as the core has a large rigid plane , the group is relatively stable, and at the same time, by introducing aromatic substituents at the 4th position of carbazole, the overall steric hindrance of the compound can be improved, and the intermolecular stacking of the material can be further adjusted, and the glass transition temperature of the compound can be effectively increased. It is not easy to crystallize, thereby improving the thermal stability of the material.
  • the nitrogen-containing compound of the present application is used as an electron blocking layer to prepare an organic electroluminescent device, it can effectively prolong the lifespan of the organic electroluminescent device and improve the luminous efficiency or driving voltage to a certain extent.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • anode 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer 360, the photoelectric conversion layer; 400, the first electronic device; 500, the second electronic device.
  • the present application provides a nitrogen-containing compound, the nitrogen-containing compound has the structure shown in formula F-1:
  • L, L 1 and L 2 are the same or different from each other, and are independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted group having 3 to 30 carbon atoms. the heteroarylene;
  • Ar 1 and Ar 2 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
  • Ar 3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;
  • R 1 , R 2 , R 3 and R 4 are the same or different from each other, and are independently selected from hydrogen, or a group represented by formula F-2, and one of R 1 , R 2 , R 3 and R 4 which is a group represented by formula F-2;
  • R 5 is selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, 6-30 substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • n 1 represents the number of R 5 , n 1 is 0, 1, 2, 3, 4 or 5;
  • the substituents in L, L 1 , L 2 , Ar 1 , Ar 2 , Ar 3 and R 5 are each independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, any An aryl group having 6 to 20 carbon atoms, optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl groups, carbon atoms Trialkylsilyl group with 3 to 12 carbon atoms, triarylsilyl group with 18 to 24 carbon atoms, alkyl group with 1 to 10 carbon atoms, halogenated alkyl group with 1 to 10 carbon atoms, carbon number alkenyl with 2 to 6 carbon atoms, alkynyl group with 2 to 6 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, heterocycloalkyl group with 2 to 10 carbon atoms, and 5 to 5 carbon atoms 10
  • Substituents in Ar 3 are selected from deuterium, halogen group, cyano group, phenyl group.
  • Aryl means that an aryl group may be substituted by one or more of deuterium, fluorine, cyano, methyl, tert-butyl, or not by deuterium, fluorine, cyano, methyl, tert-butyl, and When the number of substituents in the aryl group is 2 or more, the substituents may be the same or different.
  • n 1 is 1.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between 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, chlorine", and its meaning is: formula Q-1 represents that there are q substituents R" on the benzene ring.
  • each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings The number q of "substituents" can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as R x ).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rx or an unsubstituted aryl group.
  • substituent namely R x
  • R x can be, for example, deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally selected from 0, 1, 2, 3, 4 or 5 by 0, 1, 2, 3, 4 or 5
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12. For example: Ar 1 is Then the number of carbon atoms is 7; L is Its carbon number is 12.
  • aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
  • the "aryl group" of the present application may contain 6-40 carbon atoms.
  • the number of carbon atoms in the aryl group may be 6-25, and in other embodiments, the number of carbon atoms in the aryl group may be is 6-18, and in other embodiments the number of carbon atoms in the aryl group may be 6-13.
  • the number of carbon atoms of an aryl group can be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, 31, 32 33, 34, 35, 36 or 40, of course, the number of carbon atoms may also be other numbers, which will not be listed here.
  • biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted pheny
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents.
  • the total number of carbon atoms of the substituents is 18.
  • aryl groups as substituents include but are not limited to: phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorene base and so on.
  • the fluorenyl group can be substituted, and the two substituent groups can be combined with each other to form a spiro structure.
  • Specific examples include but are not limited to the following structures:
  • a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and 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, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic The ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
  • heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • the "heteroaryl group" of the present application may contain 3-30 carbon atoms, in some embodiments, the number of carbon atoms in the heteroaryl group may be 3-30, and in other embodiments, the carbon atoms in the aryl group The number may be 3-20, and in other embodiments the number of carbon atoms in the aryl group may be 12-20.
  • the number of carbon atoms can be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30.
  • the number of carbon atoms can also be are other quantities, which will not be listed here.
  • the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, N-phenylcarbazolyl, and the like. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • heteroaryl groups as substituents include but are not limited to: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthroline, etc. .
  • any two adjacent R j form a ring may include two R j on the same atom, and may also include one R j on each of the two adjacent atoms ; Wherein, when there are two R j on the same atom, the two R j can form a saturated or unsaturated ring with the atom to which they are connected together; when two adjacent atoms have one R j respectively, the two R j can be fused to form a ring.
  • any two adjacent substituents forming a ring also have the same explanation, which will not be repeated in this application.
  • a non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (X) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring, and the meaning it represents includes such as formula (X) -1) to any possible connection method shown in formula (X-10).
  • the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, which represents The meaning of , includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
  • the substituent R group represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings it represents include such as formula (Y-1) ⁇ Any possible connection mode shown by formula (Y-7).
  • the alkyl group with 1-10 carbon atoms may include straight-chain alkyl groups with 1-10 carbon atoms and branched-chain alkyl groups with 3-10 carbon atoms, for example, the number of carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
  • alkyl group having 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 and the like.
  • halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
  • trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • triarylsilyl group having 18 to 24 carbon atoms include, but are not limited to, triphenylsilyl and the like.
  • cycloalkyl groups having 3 to 20 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • the nitrogen-containing compound is selected from compounds represented by any one of the following chemical formulas:
  • the L, L 1 and L 2 are the same or different from each other, and are independently selected from a single bond, a substituted or unsubstituted arylene group with 6 to 25 carbon atoms, a carbon A substituted or unsubstituted heteroarylene group having 3 to 25 atoms.
  • the L, L 1 and L 2 are the same or different from each other, and are independently selected from single bonds, substituted or unsubstituted arylene groups with 6 to 20 carbon atoms, and 12 to 12 carbon atoms. 20 of substituted or unsubstituted heteroarylene.
  • the substituents in L, L 1 and L 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, carbon atom number It is an aryl group of 6 to 18 and a heteroaryl group of 12 to 18 carbon atoms.
  • the substituents in the L, L 1 and L 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl , phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, etc.
  • the L, L 1 and L 2 are the same or different from each other, and are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthalene base, substituted or unsubstituted biphenylene, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolylylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted N-phenylcarbazolylidene.
  • the substituents in L, L 1 and L 2 are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, Phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.
  • the Ar 3 is selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, preferably, the substituent in Ar 3 is a phenyl group.
  • the Ar 3 is selected from unsubstituted phenyl, unsubstituted naphthyl, and unsubstituted biphenyl.
  • Ar 3 is selected from the group consisting of the following groups:
  • the L, L 1 and L 2 are each independently selected from a single bond or a substituted or unsubstituted group W, and the unsubstituted group W is selected from the following groups: Group:
  • the substituted group W has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen group, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, anthracenyl; when the number of substituents in the group W is greater than 1, the substituents are the same or different.
  • the L, 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 the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 36 carbon atoms, and substituted or unsubstituted aryl groups having 3 to 25 carbon atoms. or unsubstituted heteroaryl.
  • Ar 1 and Ar 2 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 33 carbon atoms, and substituted or unsubstituted hetero groups having 3 to 25 carbon atoms.
  • Aryl is independently selected from substituted or unsubstituted aryl groups having 6 to 33 carbon atoms, and substituted or unsubstituted hetero groups having 3 to 25 carbon atoms.
  • Ar 1 and Ar 2 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups having 6 to 33 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms. base.
  • the substituents in Ar 1 and Ar 2 are the same or different from each other, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and carbon atoms with An aryl group of 6 to 20, and a heteroaryl group of 12 to 20 carbon atoms.
  • the substituents in Ar 1 and Ar 2 are the same or different from each other, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1 to 5 carbon atoms, and An aryl group of 6 to 18 and a heteroaryl group of 12 to 18 carbon atoms.
  • the substituents in Ar 1 and Ar 2 include but are not limited to deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, bi- Phenyl, terphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl and the like.
  • the Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups:
  • the substituted group V has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, anthracenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl; when group V When the number of substituents is greater than 1, each substituent is the same or different.
  • Ar 1 and Ar 2 are independently selected from the group consisting of the following groups:
  • the nitrogen-containing compound is selected from the group consisting of the following compounds:
  • the present application does not specifically limit the synthesis method of the nitrogen-containing compound provided, and those skilled in the art can determine a suitable synthesis method according to the preparation method provided in the synthesis example section of the present application for the nitrogen-containing compound.
  • the Synthesis Examples section of the present application exemplarily provides a method for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art.
  • Those skilled in the art can obtain all nitrogen-containing compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not interpret it as a limit.
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the functional layer described in the first aspect of the present application Nitrogenous compounds.
  • the nitrogen-containing compound provided in the present application has good hole transport performance and stability, and can be used as an electron blocking layer material for the organic electroluminescence device, and can be used in electronic components to form a material in a functional layer. At least one organic film layer to improve the efficiency characteristics and lifetime characteristics of electronic components.
  • the functional layer includes an electron blocking layer, and the electron blocking layer includes the nitrogen-containing compound provided in the present application.
  • the electron blocking layer may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.
  • the hole transport layer is adjacent to the electron blocking layer and is closer to the anode relative to the electron blocking layer.
  • the electron blocking layer comprises the nitrogen-containing compound of the present application, and the organic electroluminescence device is a green light device.
  • the electronic component may be an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100 , a hole transport layer 321 , an electron blocking layer 322 , an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340 and a cathode 200 , which are sequentially stacked.
  • 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, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; 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 conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-di] oxy)thiophene] (PEDT), polypyrrole and polyaniline. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,
  • the hole transport layer 321 may include an inorganic dopant material to improve the hole transport capability of the hole transport layer 321 .
  • the hole transport layer 321 includes one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, to which this application applies No special restrictions are made.
  • the hole transport layer 321 may be composed of the compound NPB.
  • the organic electroluminescent device is a green light device
  • the electron blocking layer 322 contains 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.
  • 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. The energy is transferred to the host material, and the host material transfers the 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 carbazole derivatives, metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. No special restrictions are made.
  • the host materials of the organic light-emitting layer 330 may be GH-n1 and GH-n2.
  • the guest material of the organic light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, a metal complex or other materials, and this application will No special restrictions are made.
  • the guest material of the organic light-emitting layer 330 may be Ir(ppy) 3 .
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of ET-06 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 multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the capability of injecting holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 may include LiQ.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200 ; the functional layer 300 includes the nitrogen-containing compound provided in the present application.
  • the functional layer 300 includes an electron blocking layer 322 , and the electron blocking layer 322 includes the nitrogen-containing compound of the present application.
  • the electron blocking layer 322 may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.
  • the photoelectric conversion device may include an anode 100 , an electron blocking layer 322 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode that are stacked in sequence.
  • 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 electroluminescence device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • 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 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the compounds of the synthetic methods not mentioned in this application are all raw materials obtained through commercial channels.
  • SM-D 35.8 g, 133.8 mmol
  • tetrahydrofuran 400 mL
  • n-butyllithium 12.8 g, 200.7 mmol
  • trimethyl borate 41.7 g, 401.4 mmol
  • the temperature was raised to room temperature and stirred for 12 h, and then an aqueous hydrochloric acid solution was added to adjust the pH to neutral.
  • the obtained reaction solution was filtered to obtain a crude product, which was recrystallized from n-heptane (600 mL) to obtain an intermediate SM-D-1 (19.6 g, 63% yield).
  • intermediate A-1 Into a round-bottomed flask that was dried and replaced with nitrogen, intermediate A-1 (56.5 g, 182.4 mmol), triphenylphosphine (119.6 g, 456.0 mmol), o-dichlorobenzene (400 mL) were added, and the temperature was raised under stirring conditions. To 160 ° C, the reaction was carried out for 6 h; then silica gel was added to it to volatilize the liquid therein, and then dichloromethane/n-heptane (volume ratio 1:3) was used as the mobile phase for purification by silica gel column chromatography to obtain intermediate B-1 ( 30.4 g, 60% yield).
  • reaction solution was cooled to room temperature, the reaction solution was extracted and washed three times with dichloromethane (50 mL) and water (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered. After filtration, the filtrate was passed through a short silica gel column and removed under reduced pressure. Solvent, the crude product was purified by recrystallization using dichloromethane/n-heptane system (1:3) to obtain compound 1 (4.8 g, yield 70%).
  • Anodes were prepared by the following process: ITO thickness was The substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers, and UV ozone and O 2 : N 2 plasma were used for surface treatment. Treatment to increase the work function of the anode (experimental substrate) and to remove scum.
  • Compound 1 was vacuum evaporated on the hole transport layer to form a thickness of electron blocking layer.
  • GH-n1:GH-n2:Ir(ppy) 3 was co-evaporated in the ratio of 50%:45%:5% (evaporation rate) to form a thickness of green organic light-emitting layer (EML).
  • ET-06 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above cathode is The CP-05 is formed to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
  • CPL organic capping layer
  • Example 12 In forming the electron blocking layer, the compound shown in Table 12 was substituted for Compound 1 in Example 1, and an organic electroluminescence device was fabricated by the same method as in Example 1.
  • Example 11 In forming the electron blocking layer, the compound A shown in Table 11 was substituted for Compound 1 in Example 1, and an organic electroluminescence device was fabricated by the same method as in Example 1.
  • Example 11 In forming the electron blocking layer, the compound B shown in Table 11 was substituted for the compound 1 in Example 1, and an organic electroluminescence device was produced by the same method as that of Example 1.
  • Example 11 In forming the electron blocking layer, the compound C shown in Table 11 was substituted for Compound 1 in Example 1, and an organic electroluminescent device was fabricated by the same method as in Example 1.
  • Example 11 In forming the electron blocking layer, the compound D shown in Table 11 was substituted for Compound 1 in Example 1, and an organic electroluminescence device was fabricated by the same method as in Example 1.

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Abstract

本申请属于有机材料技术领域，具体公开了一种含氮化合物以及使用其的电子元件和电子装置，该含氮化合物具有式（I）所示的结构。将本申请的化合物作为电子阻挡层用于制备有机电致发光器件时，能够有效地延长有机电致发光器件的寿命，并一定程度上改善发光效率或驱动电压。

Description

一种含氮化合物以及使用其的电子元件和电子装置
相关申请的交叉引用
本申请要求于2020年10月21日递交的申请号为202011135326.7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以及使用其的电子元件和电子装置。
背景技术
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。该类电子元器件通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
以有机电致发光器件为例，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、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，进而使得电致发光层对外发光。
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有机电致发光器件中，提高有机电致发光器件的性能。
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式F-1所示的结构：
Figure PCTCN2021124790-appb-000001
其中，
Figure PCTCN2021124790-appb-000002
表示化学键；
L、L 1和L 2彼此相同或不同，且分别独立地选自单键、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；
Ar 1和Ar 2彼此相同或不同，且分别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3～30的取代或未取代的杂芳基；
Ar 3选自碳原子数为6～20的取代或未取代的芳基；
R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自氢、或式F-2所示的基团，且R 1、R 2、R 3和R 4中的一者为式F-2所示的基团；
R 5选自氘、氰基、卤素基团、碳原子数为1～10的取代或未取代的烷基、碳原子数为3～20的取代或未取代的环烷基、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
n 1表示R 5的个数，n 1为0、1、2、3、4或5；
L、L 1、L 2、Ar 1、Ar 2、R 5中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基；
Ar 3中的取代基选自氘、卤素基团、氰基、苯基。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的含氮化合物；
优选地，所述功能层包括电子阻挡层，所述电子阻挡层包含所述含氮化合物。
本申请第三方面提供一种电子装置，所述电子装置包括本申请第二方面所述的电子元件。
本申请的含氮化合物具有以咔唑衍生物为母核并结合芳香胺基团的分子结构。化合物通过母核与周围空穴传输基团的协同作用，改善整个分子的稳定性和空穴传输性能。该含氮化合物中的芳胺结构能提高空穴在器件中的传输效率，并将电子阻挡在发光层内，大幅提高载流子复合率；而作为母核的咔唑结构具有大的刚性平面，基团比较稳固，同时，通过在咔唑的4号位引入芳香类取代基，提高化合物整体的立体位阻，进一步可以调节材料分子间的堆叠，有效提高化合物的玻璃化转变温度，使其不易结晶化，从而提高材料的热稳定性。本申请的含氮化合物作为电子阻挡层用于制备有机电致发光器件时，能够有效地延长有机电致发光器件的寿命，并在一定程度上改善发光效率或驱动电压。
附图说明
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的结构示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；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。应当理解的是，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。
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式F-1所示的结构：
Figure PCTCN2021124790-appb-000003
其中，
Figure PCTCN2021124790-appb-000004
表示化学键；
L、L 1和L 2彼此相同或不同，且分别独立地选自单键、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；
Ar 1和Ar 2彼此相同或不同，且分别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3～30的取代或未取代的杂芳基；
Ar 3选自碳原子数为6～20的取代或未取代的芳基；
R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自氢、或式F-2所示的基团，且R 1、R 2、R 3和R 4中的一者为式F-2所示的基团；
R 5选自氘、氰基、卤素基团、碳原子数为1～10的取代或未取代的烷基、碳原子数为3～20的取代或未取代的环烷基、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
n 1表示R 5的个数，n 1为0、1、2、3、4或5；
L、L 1、L 2、Ar 1、Ar 2、Ar 3、R 5中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基；
Ar 3中的取代基选自氘、卤素基团、氰基、苯基。
在本申请中，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基”是指芳基可以被氘、氟、氰基、甲基、叔丁基中的一个或多个取代，也可以不被氘、氟、氰基、甲基、叔丁基取代，且当芳基中的取代基的个数大于等于2时，取代基可以相同或不同。
优选地，n 1为1。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2021124790-appb-000005
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为R x)。例如，“取代或未取代的芳基”是指具有取代基R x的芳基或者非取代的芳基。其中上述的取代基即R x例如可以为氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原 子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基；当同一个原子上连接有两个取代基R x时，这两个取代基R x可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基R x时，相邻的两个取代基R x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L选自取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar 1为
Figure PCTCN2021124790-appb-000006
则其碳原子数为7；L为
Figure PCTCN2021124790-appb-000007
其碳原子数为12。
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，联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021124790-appb-000008
基等。本申请的“芳基”可含有6-40个碳原子，在一些实施例中，芳基中的碳原子数可以是6-25个，在另一些实施例中芳基中的碳原子数可以是6-18个，在另一些实施例中芳基中的碳原子数可以是6-13个。举例而言，本申请中，芳基的碳原子数量可以是6个、12个、13个、14个、15个、18个、20个、24个、25个、30个、31个、32个、33个、34个、35个、36个或40个，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
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、环烷基、烷氧基、烷硫基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基及其取代基的总碳原子数为18。
在本申请中，作为取代基的芳基，具体实例包括但不限于：苯基、萘基、蒽基、菲基、二甲基芴基、联苯基、二苯基芴基、螺二芴基等等。
在本申请中，芴基可以是取代的，两个取代基可以彼此结合形成螺结构，具体施例包括但不限于以下结构：
Figure PCTCN2021124790-appb-000009
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-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-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。本申请的“杂芳基”可含有3-30个碳原子，在一些实施例中，杂芳基中的碳原子数可以是3-30个，在另一些实施例中芳基中的碳原子数可以是3-20个，在另一些实施例中芳基中的碳原子数可以是12-20个。举例而言，其碳原子数量可以是3个、4个、5个、7个、12个、13个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
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、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、N-苯基咔唑基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基，具体实例包括但不限于：二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、菲咯啉基等等。
在本申请中，“任意两个相邻的R j形成环中，“任意相邻”可以包括同一个原子上具有两个R j，还可以包括两个相邻的原子上分别具有一个R j；其中，当同一个原子上具有两个R j时，两个R j可以与其共同连接的该原子形成饱和或不饱和的环；当两个相邻的原子上分别具有一个R j，这两个R j可以稠合成环。同理，任意两个相邻的取代基形成环也具有相同的解释，本申请不再赘述。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021124790-appb-000010
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(X)中所示的，式(X)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(X-1)～式(X-10)所示出的任一可能的连接方式。
Figure PCTCN2021124790-appb-000011
再举例而言，如下式(X')中所示地，式(X')所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2021124790-appb-000012
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，下式(Y)中所示的，式(Y)所表示的取代基R基通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2021124790-appb-000013
在本申请中，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。
在本申请中，卤素基团可以包括氟、碘、溴、氯等。
在本申请中，碳原子数为3～12的三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。
在本申请中，碳原子数为18～24的三芳基硅基的具体实例包括但不限于：三苯基硅基等。
在本申请中，碳原子数为3～20的环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基等。
可选地，所述含氮化合物选自如下化学式中任意一项所示的化合物：
Figure PCTCN2021124790-appb-000014
在本申请一种实施方式中，所述L、L 1和L 2彼此相同或不同，且分别独立地选自单键、碳原子数为6～25的取代或未取代的亚芳基、碳原子数为3～25的取代或未取代的亚杂芳基。
可选地，所述L、L 1和L 2彼此相同或不同，且分别独立地选自单键、碳原子数为6～20的取代或未取代的亚芳基、碳原子数为12～20的取代或未取代的亚杂芳基。
可选地，所述L、L 1和L 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～18的芳基、碳原子数为12～18的杂芳基。
具体地，所述L、L 1和L 2中的取代基相同或不同，且分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基等。
在本申请另一种实施方式中，所述L、L 1和L 2彼此相同或不同，且分别独立地选自单键、取代或未取代的亚苯基、取代或未取待的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚二甲基芴基、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、取代或未取代的亚二苯并噻吩基、取代或未取代的N-苯基咔唑亚基。
优选地，所述L、L 1和L 2中的取代基相同或不同，分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三联苯基、菲基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基。
在本申请一种实施方式中，所述Ar 3选自碳原子数为6～12的取代或未取代的芳基，优选地，Ar 3中的取代基为苯基。
进一步优选地，所述Ar 3选自未取代的苯基、未取代的萘基、未取代的联苯基。
在本申请一种实施方式中，Ar 3选自如下基团组成的组：
Figure PCTCN2021124790-appb-000015
在本申请一种实施方式中，所述L、L 1和L 2各自独立地选自单键或者取代或未取代的基团W，所述未取代的基团W选自如下基团组成的组：
Figure PCTCN2021124790-appb-000016
其中，
Figure PCTCN2021124790-appb-000017
表示化学键；取代的基团W上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基；当基团W中的取代基个数大于1时，各取代基相同或不同。
可选地，所述L、L 1和L 2各自独立地选自单键或如下基团组成的组：
Figure PCTCN2021124790-appb-000018
Figure PCTCN2021124790-appb-000019
在本申请一种实施方式中，Ar 1和Ar 2彼此相同或不同，且分别独立地选自碳原子数为6～36的取代或未取代的芳基、碳原子数为3～25的取代或未取代的杂芳基。
可选地，Ar 1和Ar 2彼此相同或不同，且分别独立地选自碳原子数为6～33的取代或未取代的芳基、碳原子数为3～25的取代或未取代的杂芳基。
优选地，Ar 1和Ar 2彼此相同或不同，且分别独立地选自碳原子数为6～33的取代或未取代的芳基、碳原子数为3～20的取代或未取代的杂芳基。
可选地，所述Ar 1和Ar 2中的取代基彼此相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6～20的芳基、碳原子数为12～20的杂芳基。
进一步可选地，所述Ar 1和Ar 2中的取代基彼此相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～18的芳基、碳原子数为12～18的杂芳基。
具体地，所述Ar 1和Ar 2中的取代基包括但不限于氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基等。
在本申请一种实施方式中，所述Ar 1和Ar 2各自独立地选自取代或未取代的基团V，所述未取代的基团V选自如下基团组成的组：
Figure PCTCN2021124790-appb-000020
其中，
Figure PCTCN2021124790-appb-000021
表示化学键；取代的基团V上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基；当基团V中的取代基个数大于1时，各取代基相同或不同。
可选地，所述Ar 1和Ar 2分别独立地选自以下基团所组成的组：
Figure PCTCN2021124790-appb-000022
在本申请中，可选地，所述含氮化合物选自如下化合物组成的组：
Figure PCTCN2021124790-appb-000023
Figure PCTCN2021124790-appb-000024
Figure PCTCN2021124790-appb-000025
Figure PCTCN2021124790-appb-000026
Figure PCTCN2021124790-appb-000027
Figure PCTCN2021124790-appb-000028
Figure PCTCN2021124790-appb-000029
Figure PCTCN2021124790-appb-000030
Figure PCTCN2021124790-appb-000031
Figure PCTCN2021124790-appb-000032
Figure PCTCN2021124790-appb-000033
Figure PCTCN2021124790-appb-000034
Figure PCTCN2021124790-appb-000035
Figure PCTCN2021124790-appb-000036
Figure PCTCN2021124790-appb-000037
Figure PCTCN2021124790-appb-000038
Figure PCTCN2021124790-appb-000039
Figure PCTCN2021124790-appb-000040
Figure PCTCN2021124790-appb-000041
Figure PCTCN2021124790-appb-000042
Figure PCTCN2021124790-appb-000043
Figure PCTCN2021124790-appb-000044
Figure PCTCN2021124790-appb-000045
Figure PCTCN2021124790-appb-000046
Figure PCTCN2021124790-appb-000047
Figure PCTCN2021124790-appb-000048
Figure PCTCN2021124790-appb-000049
Figure PCTCN2021124790-appb-000050
Figure PCTCN2021124790-appb-000051
Figure PCTCN2021124790-appb-000052
Figure PCTCN2021124790-appb-000053
Figure PCTCN2021124790-appb-000054
Figure PCTCN2021124790-appb-000055
Figure PCTCN2021124790-appb-000056
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，本申请的合成例部分示例性地提供了含氮化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有含氮化合物，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、以及设置在所述阳极与所述阴极之间的功能层，其中，所述功能层含有本申请第一方面所述的含氮化合物。
本申请所提供的含氮化合物具有较好的空穴传输性能和稳定性，可以用作所述有机电致发光器件的电子阻挡层材料，将其用于电子元件可以用于形成功能层中的至少一个有机膜层，以改善电子元件的效率特性和寿命特性。
可选地，功能层包括电子阻挡层，电子阻挡层包含本申请所提供的含氮化合物。其中，电子阻挡层既可以由本申请所提供的含氮化合物组成，也可以由本申请所提供的含氮化合物和其他材料共同组成。
按照一种实施方式，空穴传输层邻接于电子阻挡层，且相对于所述电子阻挡层更靠近阳极。
优选地，所述电子阻挡层包含本申请的含氮化合物，所述有机电致发光器件为绿光器件。
按照一种实施方式，电子元件可以为有机电致发光器件。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、作为能量转化层的有机发光层330、电子传输层340和阴极200。
本申请中，阳极100包括阳极材料，其优选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。阳极材料的具体实例包括但不限于：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺。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。
按照一种实施方式，空穴传输层321可以包括无机掺杂材料，以提高空穴传输层321的空穴传输性能力。
可选地，空穴传输层321包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，空穴传输层321可以由化合物NPB组成。
按照一种更具体的实施方式，所述有机电致发光器件为绿光器件，所述电子阻挡层322含有本申请的所述含氮化合物。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。一种具体的实施方式中，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的主体材料可以为咔唑类衍生物、金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的主体材料可以为GH-n1和GH-n2。
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、芳香族胺衍生物、金属配合物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的客体材料可以为Ir(ppy) 3。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，苯并咪唑衍生物、恶二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种实施方式中，电子传输层340可以由ET-06和LiQ组成。
本申请中，GH-n1和GH-n2和ET-06等化合物的具体结构如下文的实施例所示，在此不再赘述。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由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可以包括LiQ。
按照另一种实施方式，电子元件可以为光电转化器件。如图3所示，该光电转化器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的含氮化合物。
按照一种示例性实施方式，如图3所示，所述功能层300包括电子阻挡层322，所述电子阻挡层322包含本申请的含氮化合物。其中，电子阻挡层322既可以为本申请所提供的含氮化合物组成，也可以由本申请所提供的含氮化合物和其他材料共同组成。
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、电子阻挡层322、光电转化层360、电子传输层340和阴极200。
可选地，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、光电转化层、电子传输层和阴极。
本申请第三方面提供一种电子装置包含本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
下面，示例性地提供数个具体实施例，以进一步解释和说明本申请。但是，下述实施例仅是本申请的例示，而并非限定本申请。
合成例
中间体的合成
Figure PCTCN2021124790-appb-000057
向干燥并经过氮气置换的圆底烧瓶中，加入1-溴-2-碘-3-氯苯(50.0g,157.5mmol)，苯硼酸(19.2g,157.5mmol)，四(三苯基膦)钯(9.1g,7.8mmol)，四丁基溴化铵(2.5g,7.8mmol)，碳酸钾(65.2g,472.6mmol)，甲苯(400mL)，乙醇(200mL)，去离子水(100mL)，搅拌条件下升温至75℃，保持8h；而后将反应混合物降至室温，加入去离子水(200mL)，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷(体积比1:3)作为流动相进行硅胶柱色谱提纯，得到中间体SM-D(35.8g,收率为85％)。
向干燥并经过氮气置换的圆底烧瓶中，加入SM-D(35.8g,133.8mmol)，四氢呋喃(400mL)，降温至零下78℃后滴加正丁基锂(12.8g,200.7mmol)，滴加完毕在零下78℃保温30min,后滴加硼酸三甲酯(41.7g,401.4mmol)，滴加完毕在零下78℃保温30min。升温至室温搅拌12h后加入盐酸水溶液调节pH至中性。将所得反应液过滤得到粗品，将粗品用正庚烷(600mL)重结晶得到 中间体SM-D-1(19.6g,收率为63％)。
参照中间体SM-D的合成方法，以下表中反应物Q替代苯硼酸，合成下表1所示的中间体：
表1
Figure PCTCN2021124790-appb-000058
参照中间体SM-D合成方法，以下表中反应物N替代1-溴-2-碘-3-氯苯，反应物M替代苯硼酸，合成下表2所示的中间体：
表2
Figure PCTCN2021124790-appb-000059
Figure PCTCN2021124790-appb-000060
参照中间体SM-D-1合成方法，以下表中(反应物)中间体替代SM-D，合成下表3所示的中间体：
表3
Figure PCTCN2021124790-appb-000061
Figure PCTCN2021124790-appb-000062
向干燥并经过氮气置换的圆底烧瓶中，加入联苯-2-硼酸(51.6g,260.4mmol)，2,4-二氯硝基苯(50.0g,260.4mmol)，四(三苯基膦)钯(15.0g,13.0mmol)，四丁基溴化铵(4.2g,13.0mmol)，碳酸钾 (107.9g,781.3mmol)，甲苯(400mL)，乙醇(200mL)，去离子水(100mL)，搅拌条件下升温至75℃，保持8h；而后将反应混合物降至室温，加入去离子水(200mL)，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷(体积比1：3)作为流动相进行硅胶柱色谱提纯，得到中间体A-1(56.5g；收率为70％)。
向干燥并经过氮气置换的圆底烧瓶中，加入中间体A-1(56.5g,182.4mmol)，三苯基膦(119.6g,456.0mmol)，邻二氯苯(400mL)，搅拌条件下升温至160℃，反应6h；而后向其中加入硅胶以挥发其中的液体，后使用二氯甲烷/正庚烷(体积比1:3)作为流动相进行硅胶柱色谱提纯，得到中间体B-1(30.4g，收率为60％)。
向干燥并经过氮气置换的圆底烧瓶中，加入中间体B-1(30.4g,109.5mmol)，碘苯(22.7.0g,111.6mmol)，碘化亚铜(4.2g,21.8mmol)，碳酸钾(33.3g,240.8mmol)，1,10-菲啰啉(7.9g,43.8mmol)，18-冠醚-6(2.9g,10.9mmol)，N,N,-二甲基甲酰胺(300mL)，搅拌条件下升温至160℃，保持8h；而后将反应混合物降至室温，加入去离子水(200mL)，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷(体积比1:3)作为流动相进行硅胶柱色谱提纯，得到中间体C-1(30.9g，收率为80％)。
参照合成中间体A-1相同的方法，以下表中反应物A替代2,4-二氯硝基苯，SM-D-X代替联苯-2-硼酸合成下表4中的中间体：
表4
Figure PCTCN2021124790-appb-000063
Figure PCTCN2021124790-appb-000064
参照中间体B-1的合成方法，以下表中反应物B替代中间体A-1，合成下表5中的中间体：
表5
Figure PCTCN2021124790-appb-000065
Figure PCTCN2021124790-appb-000066
参照合成中间体C-1相同的方法，以下表中反应物C替代中间体B-1，合成下表6中的中间体：
表6
Figure PCTCN2021124790-appb-000067
Figure PCTCN2021124790-appb-000068
向干燥并经过氮气置换的圆底烧瓶中，加入对氯苯硼酸(2.19g,14.13mmol)，中间体C-1(5.0g,14.13mmol)，四(三苯基膦)钯(0.82g,0.70mmol)，四丁基溴化铵(0.23g,0.71mmol)，碳酸钾(3.90g,28.26mmol)，甲苯(40mL)，乙醇(20mL)，去离子水(10mL)，搅拌条件下升温至75℃，保持8h；而后将反应混合物降至室温，加入去离子水(100mL)，搅拌15分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用二氯甲烷/正庚烷(体积比1：3)作为流动相进行硅胶柱色谱提纯，得到中间体D-1(4.6g，收率为75％)。
使用与合成中间体D-1相同的方法，以下表中反应物D替代中间体C-1，SM-D替代对氯苯硼酸，合成下表7中的中间体：
表7
Figure PCTCN2021124790-appb-000069
Figure PCTCN2021124790-appb-000070
向反应瓶中投入中间体C-2(10g，14.1mmol)、SM-1(二苯胺)(2.4g，14.1mmol)、三(二亚苄基丙酮)二钯(0.1g，0.1mmol)、2-二环己基膦-2’,6’-二甲氧基-联苯(0.1g，0.3mmol)、叔丁醇钠(2.0g，21.2mmol)和甲苯溶剂(100mL)，氮气保护下升温至110℃，加热回流搅拌8h。反应液冷却至室温后，利用二氯甲烷(50mL)和水(50mL)萃取和水洗反应溶液3次，有机层经无水硫酸镁干燥并过滤，过滤后将滤液通过短硅胶柱，减压除去溶剂，使用二氯甲烷/正庚烷体系(1:3)对粗品进行重结晶提纯，得到化合物1(4.8g，收率为70％)。
参照化合物1的合成方法，以下表中SM-Y替代SM-1(二苯胺)，用中间体C-X/D-X代替中间体C-1。合成下表8中的化合物：
表8
Figure PCTCN2021124790-appb-000071
Figure PCTCN2021124790-appb-000072
Figure PCTCN2021124790-appb-000073
Figure PCTCN2021124790-appb-000074
Figure PCTCN2021124790-appb-000075
Figure PCTCN2021124790-appb-000076
化合物表征
对以上合成化合物进行质谱分析，得到数据如下表9。
表9
化合物编号 质谱[M+H] + 化合物编号 质谱[M+H] + 化合物编号 质谱[M+H] +
1 487.3 2 537.3 4 563.3
7 577.3 11 593.3 74 537.3
76 563.3 186 639.3 190 653.3
191 669.3 197 689.3 245 639.3
246 653.3 314 653.3 378 613.3
386 669.3 443 679.3 488 639.3
491 653.3 734 603.3 1007 719.3
1028 613.3 1161 639.3 1187 729.3
1235 689.3 1242 715.3 1243 745.3
1244 765.3 1249 765.3 1250 714.3
1251 837.4 1252 573.3 1253 555.2
1254 703.3 1255 729.3 1256 728.3
1257 727.3 1258 663.3 1259 704.3
1260 667.3        
部分化合物及中间体的核磁数据如下表10：
表10
Figure PCTCN2021124790-appb-000077
器件实施例
实施例1：绿色有机电致发光器件
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021124790-appb-000078
的基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为的厚度为
Figure PCTCN2021124790-appb-000079
的空穴注入层(HIL)，并且在空穴注入层蒸镀NPB，形成厚度为
Figure PCTCN2021124790-appb-000080
的空穴传输层。
在空穴传输层上真空蒸镀化合物1，形成厚度为
Figure PCTCN2021124790-appb-000081
的电子阻挡层。
在电子阻挡层上，将GH-n1：GH-n2：Ir(ppy) 3以50％：45％：5％(蒸镀速率)的比例进行共同蒸镀，形成厚度为
Figure PCTCN2021124790-appb-000082
的绿色有机发光层(EML)。
将ET-06和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021124790-appb-000083
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021124790-appb-000084
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021124790-appb-000085
的阴极。
在上述阴极上蒸镀厚度为
Figure PCTCN2021124790-appb-000086
的CP-05，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2-实施例40
在形成电子阻挡层时，以表12中所示的化合物替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
比较例1
在形成电子阻挡层时，以表11中所示的化合物A替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
比较例2
在形成电子阻挡层时，以表11中所示的化合物B替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
比较例3
在形成电子阻挡层时，以表11中所示的化合物C替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
比较例4
在形成电子阻挡层时，以表11中所示的化合物D替代实施例1中的化合物1，利用与实施例1相同的方法制作有机电致发光器件。
在实施例1-40和比较例1-4中，所使用的各个材料的结构式如下表11所示：
表11
Figure PCTCN2021124790-appb-000087
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果示于下表12：
表12：
Figure PCTCN2021124790-appb-000088
Figure PCTCN2021124790-appb-000089
根据表12的结果可知，作为电子阻挡层的化合物的实施例1-40与使用已公知的化合物A、化合物B、化合物C及化合物D的比较例1-4相比，本申请中使用的化合物作电子阻挡层制备的上述有机电致发光器件的驱动电压至少降低了0.18V，电流效率至少提高了22.8％，外量子效率至少提高了22.6％，寿命至少提高了9.69％。
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。
此外，本申请的各种不同的实施方式之间也可以进行任意组合，只要其不违背本申请的思想，其同样应当视为本申请所公开的内容。

Claims (14)

  1. 一种含氮化合物，其特征在于，所述含氮化合物具有式F-1所示的结构：
    Figure PCTCN2021124790-appb-100001
    其中，
    Figure PCTCN2021124790-appb-100002
    表示化学键；
    L、L 1和L 2彼此相同或不同，且分别独立地选自单键、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；
    Ar 1和Ar 2彼此相同或不同，且分别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3～30的取代或未取代的杂芳基；
    Ar 3选自碳原子数为6～20的取代或未取代的芳基；
    R 1、R 2、R 3和R 4彼此相同或不同，且分别独立地选自氢、或式F-2所示的基团，且R 1、R 2、R 3和R 4中的一者为式F-2所示的基团；
    R 5选自氘、氰基、卤素基团、碳原子数为1～10的取代或未取代的烷基、碳原子数为3～20的取代或未取代的环烷基、碳原子数为6～30的取代或未取代的芳基、碳原子数为3～30的取代或未取代的杂芳基；
    n 1表示R 5的个数，n 1为0、1、2、3、4或5；
    L、L 1、L 2、Ar 1、Ar 2、R 5中的取代基各自独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基；
    Ar 3中的取代基选自氘、卤素基团、氰基、苯基。
  2. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下化学式中任意一项所示的化合物：
    Figure PCTCN2021124790-appb-100003
  3. 根据权利要求1所述的含氮化合物，其特征在于，所述L、L 1和L 2彼此相同或不同，且分别独立地选自单键、碳原子数为6～20的取代或未取代的亚芳基、碳原子数为12～20的取代或未取代的亚杂芳基；
    优选地，所述L、L 1和L 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～18的芳基、碳原子数为12～18的杂芳基。
  4. 根据权利要求1所述的含氮化合物，其特征在于，所述L、L 1和L 2彼此相同或不同，且分别独立地选自单键、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、 取代或未取代的亚二甲基芴基、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、取代或未取代的亚二苯并噻吩基、取代或未取代的N-苯基咔唑亚基；
    优选地，所述L、L 1和L 2中的取代基相同或不同，且分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、三联苯基、菲基、二甲基芴基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基。
  5. 根据权利要求1所述的含氮化合物，其特征在于，所述L、L 1和L 2各自独立地选自单键或者取代或未取代的基团W，所述未取代的基团W选自如下基团组成的组：
    Figure PCTCN2021124790-appb-100004
    其中，
    Figure PCTCN2021124790-appb-100005
    表示化学键；取代的基团W上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基；当基团W中的取代基个数大于1时，各取代基相同或不同。
  6. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1和Ar 2彼此相同或不同，且分别独立地选自碳原子数为6～33的取代或未取代的芳基、碳原子数为3～25的取代或未取代的杂芳基；
    优选地，所述Ar 1和Ar 2中的取代基彼此相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6～20的芳基、碳原子数为12～20的杂芳基。
  7. 根据权利要求1的所述的含氮化合物，其特征在于，所述Ar 3选自碳原子数为6-12的取代或未取代的芳基；
    优选地，所述Ar 3中的取代基为苯基。
  8. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1和Ar 2各自独立地选自取代或未取代的基团V，所述未取代的基团V选自如下基团组成的组：
    Figure PCTCN2021124790-appb-100006
    其中，
    Figure PCTCN2021124790-appb-100007
    表示化学键；取代的基团V上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、蒽基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基；当基团V中的取代基个数大于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，其特征在于，所述含氮化合物选自如下化合物所组成的组：
    Figure PCTCN2021124790-appb-100008
    Figure PCTCN2021124790-appb-100009
    Figure PCTCN2021124790-appb-100010
    Figure PCTCN2021124790-appb-100011
    Figure PCTCN2021124790-appb-100012
    Figure PCTCN2021124790-appb-100013
    Figure PCTCN2021124790-appb-100014
    Figure PCTCN2021124790-appb-100015
    Figure PCTCN2021124790-appb-100016
    Figure PCTCN2021124790-appb-100017
    Figure PCTCN2021124790-appb-100018
    Figure PCTCN2021124790-appb-100019
    Figure PCTCN2021124790-appb-100020
    Figure PCTCN2021124790-appb-100021
    Figure PCTCN2021124790-appb-100022
    Figure PCTCN2021124790-appb-100023
    Figure PCTCN2021124790-appb-100024
    Figure PCTCN2021124790-appb-100025
    Figure PCTCN2021124790-appb-100026
    Figure PCTCN2021124790-appb-100027
    Figure PCTCN2021124790-appb-100028
    Figure PCTCN2021124790-appb-100029
    Figure PCTCN2021124790-appb-100030
    Figure PCTCN2021124790-appb-100031
    Figure PCTCN2021124790-appb-100032
    Figure PCTCN2021124790-appb-100033
    Figure PCTCN2021124790-appb-100034
    Figure PCTCN2021124790-appb-100035
    Figure PCTCN2021124790-appb-100036
    Figure PCTCN2021124790-appb-100037
    Figure PCTCN2021124790-appb-100038
    Figure PCTCN2021124790-appb-100039
    Figure PCTCN2021124790-appb-100040
    Figure PCTCN2021124790-appb-100041
  10. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下化合物：
    Figure PCTCN2021124790-appb-100042
  11. 一种电子元件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含权利要求1至10中任意一项所述的含氮化合物；
    优选地，所述功能层包括电子阻挡层，所述电子阻挡层包含所述含氮化合物。
  12. 根据权利要求11所述的电子元件，其特征在于，所述电子元件为有机电致发光器件或光电转化器件。
  13. 根据权利要求12所述的电子元件，其特征在于，所述电子元件为有机电致发光器件；所述有机电致发光器件为绿色器件。
  14. 一种电子装置，其特征在于，包含权利要求11至13中任意一项所述的电子元件。
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