WO2021223650A1 - 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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WO2021223650A1
WO2021223650A1 PCT/CN2021/090725 CN2021090725W WO2021223650A1 WO 2021223650 A1 WO2021223650 A1 WO 2021223650A1 CN 2021090725 W CN2021090725 W CN 2021090725W WO 2021223650 A1 WO2021223650 A1 WO 2021223650A1
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carbon atoms
group
groups
nitrogen
containing compound
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WO2021223650A9 (zh
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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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Priority to US17/787,656 priority Critical patent/US11691952B2/en
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Definitions

  • This application belongs to the technical field of organic materials, and specifically provides a nitrogen-containing compound and an electronic component and an electronic device using the nitrogen-containing compound.
  • Organic light-emitting devices are representative examples of organic electronic devices.
  • the organic luminescence phenomenon refers to the phenomenon of using organic substances to convert electrical energy into light energy.
  • An organic light-emitting element that utilizes an organic light-emitting phenomenon generally has a structure including an anode and a cathode, and an organic layer between them.
  • the organic layer is often formed of a multilayer structure composed of different substances.
  • the organic layer may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, The electron injection layer is formed.
  • electron transport materials are compounds with electron-deficient nitrogen-containing heterocyclic groups. Most of them have higher electron affinity and therefore have a stronger ability to accept electrons.
  • hole transport materials For example, the electron mobility of common electron transport materials such as octahydroxyquinoline aluminum is much lower than that of hole transport materials. Therefore, in OLED devices, on the one hand, the injection and transport of carriers will be unbalanced. The recombination probability of holes and electrons is reduced, thereby reducing the luminous efficiency of the device.
  • electron transport materials with lower electron mobility will cause the operating voltage of the device to increase, thereby affecting power efficiency and detrimental to energy conservation.
  • the purpose of this application is to provide a nitrogen-containing compound and electronic components and electronic devices using the nitrogen-containing compound, which can be used as a hole blocking layer and/or an organic electroluminescent device Electron transport layer.
  • the first aspect of the application provides a nitrogen-containing compound, and the structural formula of the nitrogen-containing compound is shown in Formula 1:
  • ring A and ring B are the same or different, and are each independently selected from a benzene ring or a fused aromatic ring having 10 to 14 ring carbon atoms, and at least one of ring A and ring B is the ring-forming carbon Condensed aromatic ring with 10 to 14 atoms;
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • Each Q 1 and each Q 2 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, halogenated alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, carbon atom Cycloalkyl groups having 3 to 15 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having 1 to 4 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, and carbon atoms 18-24 triarylsilyl groups, 6-12 aryl groups, 7-13 aralkyl groups, 4-12 heteroaryl groups, carbon atoms 5 to 13 heteroaralkyl groups;
  • n represents the number of Q 1 and is selected from 0 or 1
  • m represents the number of Q 2 and is selected from 0 or 1;
  • Het is a substituted or unsubstituted nitrogen-containing heteroaryl group with 3-30 carbon atoms
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
  • the substituents in L, Het, Ar 1 and Ar 2 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, aryl group having 6 to 25 carbon atoms, and Heteroaryl groups having 3 to 25, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and those having 1 to 10 carbon atoms An alkoxy group, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms.
  • the second aspect of the present application provides an electronic component, including an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer includes the nitrogen-containing Compound; preferably, the functional layer includes an electron transport layer, the electron transport layer includes the nitrogen-containing compound; preferably, the functional layer includes a hole blocking layer, the hole 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 component described in the second aspect of the present application.
  • the nitrogen-containing compound provided in the present application has a molecular structure in which a heteroaryl group is combined with a fused ring adamantane fluorene.
  • the molecular structure can reduce the energy level injection barrier, thereby reducing the operating voltage of the organic electroluminescent device, and increasing the open circuit voltage of the photoelectric conversion device.
  • the molecular structure has a large molecular weight, and the fused ring structure can increase steric hindrance, thereby adjusting the structure, making the material difficult to crystallize or agglomerate, so that the material has a better life in electronic components.
  • the molecular structure has electron-rich characteristics, the polarity of the entire molecule is enhanced, which is more conducive to the directional arrangement of the material molecules, thereby enhancing the injection and transmission of electrons, enhancing the electronic conductivity of the electron transport material, and improving the application of the
  • the luminous efficiency of the organic light-emitting device of the nitrogen-containing compound, and the conversion efficiency of the photoelectric conversion device using the nitrogen-containing compound is improved.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • Anode; 200 cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, organic light emitting layer; 341, hole blocking layer, 340, electron transport Layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • the first aspect of the application provides a nitrogen-containing compound, and the structural formula of the nitrogen-containing compound is shown in Formula 1:
  • ring A and ring B are the same or different, and are each independently selected from a benzene ring or a fused aromatic ring having 10 to 14 ring carbon atoms, and at least one of ring A and ring B is the ring-forming carbon The fused aromatic ring having 10 to 14 atoms;
  • L is connected to ring A or ring B;
  • the nitrogen-containing compound represented by Formula 1 may be selected from compounds represented by Formula A or Formula B;
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
  • Each Q 1 and each Q 2 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, halogenated alkyl group having 1 to 10 carbon atoms, alkyl group having 1 to 10 carbon atoms, carbon Cycloalkyl groups having 3 to 15 atoms, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having 1 to 4 carbon atoms, trialkylsilyl groups having 3 to 12 carbon atoms, carbon A triarylsilyl group with 18 to 24 atoms, an aryl group with 6 to 12 carbon atoms, an aralkyl group with 7 to 13 carbon atoms, a heteroaryl group with 4 to 12 carbon atoms, and the number of carbon atoms Heteroaralkyl of 5-13;
  • n represents the number of Q 1 and is selected from 0 or 1
  • m represents the number of Q 2 and is selected from 0 or 1;
  • Het is a substituted or unsubstituted nitrogen-containing heteroaryl group with 3-30 carbon atoms
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from: hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms , Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
  • the substituents in L, Het, Ar 1 and Ar 2 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, aryl group having 6 to 25 carbon atoms, and Heteroaryl groups having 3 to 25, alkyl groups having 1 to 10 carbon atoms, haloalkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, and those having 1 to 10 carbon atoms An alkoxy group, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and a triarylsilyl group having 18 to 24 carbon atoms.
  • Het may be a substituted or unsubstituted nitrogen-containing heteroaryl group having 3 to 30 carbon atoms
  • Het may or may not include a substituent.
  • the substituent in Het refers to a substituent other than Ar 1 and Ar 2 .
  • ring A and ring B are the same or different, and are each independently selected from a benzene ring or a fused aromatic ring with 10 to 14 ring carbon atoms.
  • the fused aromatic ring may be a naphthalene ring, an anthracene ring, Philippine ring.
  • ring A or ring B is a phenyl group; L is connected to the phenyl group.
  • the nitrogen-containing compound provided in this application has a molecular structure in which a heteroaryl group is combined with a fused ring adamantane fluorene.
  • the molecular structure can reduce the energy level injection barrier, thereby lowering the operating voltage of the organic electroluminescence device, and increasing the open circuit voltage of the photoelectric conversion device.
  • the molecular structure has a large molecular weight, which increases molecular asymmetry, and can adjust the structure so that the material is not easy to crystallize or aggregate, so that the material has a better life in electronic components.
  • the molecular structure has electron-rich characteristics, and the polarity of the entire molecule is enhanced, which is more conducive to the directional arrangement of the material molecules, thereby enhancing the injection and transmission of electrons.
  • the fused ring structure can enhance the electronic conductivity of the electron transport material, and at the same time can increase the luminous efficiency of the organic light-emitting device using the nitrogen-containing compound, and increase the conversion efficiency of the photoelectric conversion device using the nitrogen-containing compound.
  • the structural formula of the nitrogen-containing compound shown in Formula 1 is selected from the group consisting of the following formulas 2 to 19:
  • the structural formula of the nitrogen-containing compound shown in Formula 1 is selected from the group consisting of the following formulas 20 to 28:
  • adamantane is a three-dimensional structure, in the compound structure diagram, because of the different drawing angles, it will show different planar shapes.
  • the ring structures formed on cyclopentane are all adamantanes, and the connection positions are also the same of. For example: the following structure All have the same structure.
  • each... are independently” and “... are independently” and “... are independently selected from” are interchangeable, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that the specific options expressed between the same symbols do not affect each other in the same group.
  • each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is:
  • formula Q-1 represents q substituents R" on the benzene ring , Each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 means that there are q substituents R" on each benzene ring of biphenyl, and R on two benzene rings The number q of "substituents can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc).
  • the "substituted or unsubstituted aryl group” refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • the above-mentioned substituent Rc can be, for example, deuterium, halogen group, cyano group, aryl group having 6 to 25 carbon atoms, heteroaryl group having 3 to 25 carbon atoms, or one having 1 to 10 carbon atoms.
  • the "substituted" functional group can be substituted by one or more than two substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc can exist independently Or they are connected to each other to form a ring with the atom; when there are two adjacent substituents Rc on the functional group, the two adjacent substituents Rc may exist independently or be condensed with the functional group to which they are connected to form a ring.
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms.
  • Ar 1 is selected from substituted aryl groups having 30 carbon atoms, all carbon atoms of the aryl group and the substituents thereon are 30.
  • the number of carbon atoms of L, Ar 1 , Ar 2 , and Het refers to the number of all carbon atoms.
  • L is a substituted arylene group with 12 carbon atoms, and all carbon atoms of the arylene group and the substituents thereon are 12.
  • Ar 1 is Then the number of carbon atoms is 7; L is The number of carbon atoms is 12.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more single Cyclic aryl groups, monocyclic aryl groups and fused ring aryl groups conjugated through carbon-carbon bonds, and two or more fused ring aryl groups conjugated through carbon-carbon bonds.
  • two or more aromatic groups conjugated through carbon-carbon bonds may also be regarded as aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (for example, a naphthyl group), a tricyclic fused aryl group (for example, a phenanthryl group, a fluorenyl group, an anthryl group), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si.
  • phenyl and the like are aryl groups.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] Phenanthryl, pyrenyl, benzofluoranthene, Base and so on.
  • the involved arylene group refers to a divalent group formed by further losing one hydrogen atom of an aryl group.
  • fused aromatic rings refer to polyaromatic rings formed by two or more aromatic rings or heteroaromatic rings sharing ring edges, such as naphthalene, anthracene, phenanthrene, and pyrene.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, and the like.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group.
  • the total number of carbon atoms of the group is 18.
  • the involved arylene group refers to a divalent group formed by further losing one hydrogen atom of an aryl group.
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may be at least one of B, O, N, P, Si, Se, and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl , Pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, diphenyl And thienyl, thieno
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
  • Heteroaryl group of ring system type is heteroaryl group of ring system type.
  • nitrogen-containing heteroaryl refers to a monovalent aromatic ring or its derivatives containing at least one heteroatom in the ring.
  • the heteroatom can be at least one of B, O, N, P, Si, Se, and S , And have at least one N.
  • the involved heteroarylene group refers to a divalent group formed by the heteroaryl group further losing one hydrogen atom.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.
  • the alkyl group having 1 to 20 carbon atoms may be a straight-chain alkyl group or a branched-chain alkyl group.
  • the alkyl group having 1 to 20 carbon atoms may be a linear alkyl group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms.
  • the number of carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, for example.
  • alkyl groups having 1 to 20 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isoamyl Base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.
  • the halogen group can be fluorine, chlorine, bromine, or iodine.
  • the non-positioned connecting bond refers to the single bond protruding from the ring system It means that one end of the link can be connected to any position in the ring system that the bond penetrates, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).
  • the dibenzofuran group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of the benzene ring on one side, Its meaning includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • the ring A and the ring B are the same or different, and are each independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring, and the ring A and the ring B are not benzene at the same time. ring.
  • the Ar 1 and Ar 2 are the same or different, and are independently selected from hydrogen, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted A cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from aryl groups having 6 to 21 carbon atoms, substituted or unsubstituted carbon atoms having 5 to 20 Heteroaryl.
  • the Ar 1 and Ar 2 are the same or different, and are independently selected from aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 12 carbon atoms. Aryl.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, and aryl groups with 6 to 20 carbon atoms.
  • the substituents of Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl Group, dimethylfluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, pyridyl, pyrimidinyl, phenothiazinyl, phenoxazinyl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of hydrogen or the following groups i-1 to i-15:
  • M 1 is selected from a single bond or
  • G 1 ⁇ G 5 and G 1 ‘ ⁇ G 4 ’ are each independently selected from N, C or C(J 1 ), and at least one of G 1 ⁇ G 5 is selected from N; when two of G 1 ⁇ G 5 When more than one is selected from C(J 1 ), any two J 1 are the same or different;
  • G 6 to G 13 are each independently selected from N, C or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ), any two J 2 are the same or different;
  • G 14 to G 23 are each independently selected from N, C or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ), any two J 3 are the same or different;
  • G 24 to G 33 are each independently selected from N, C or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ), any two J 4 are the same or different;
  • Z 1 is selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and haloalkyl group having 1 to 10 carbon atoms , Cycloalkyl groups with 3-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, alkylthio groups with 1-10 carbon atoms, triarylsilyl groups with 18-24 carbon atoms;
  • Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, C1-C10 haloalkyl group, C3-C10 cycloalkyl group, C1-C10 alkoxy group, C1-C10 alkylthio group, C1-C10 It is an alkylthio group of 1 to 10, a heteroaryl group of 3 to 18 carbon atoms, and a triarylsilyl group of 18 to 24 carbon atoms;
  • Z 10 to Z 20 and J 1 to J 4 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, and one having 1 to 10 carbon atoms Alkyl group, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, alkoxy group having 1-10 carbon atoms, alkylthio group having 1-10 carbon atoms, An aryl group with 6 to 18 carbon atoms, a heteroaryl group with 3 to 18 carbon atoms, and a triaryl group with 18 to 24 carbon atoms optionally substituted by one or more deuterium, fluorine, chlorine, or cyano groups
  • an aryl group with 6 to 18 carbon atoms optionally substituted with one or more deuterium, fluorine, chlorine, and cyano groups means that the aryl group can be substituted by deuterium, fluorine, or chlorine.
  • h 1 ⁇ h 21 are represented by h k
  • Z 1 ⁇ Z 21 are represented by Z k
  • k is a variable, representing any integer from 1 to 21
  • h k is the number of substituents Z k ; wherein, when k is selected from 5 Or when 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected When from 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 Or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
  • K 1 is selected from O, S, N (Z 22 ), C (Z 23 Z 24 ), Si (Z 28 Z 29 ); wherein, Z 22 , Z 23 , Z 24 , Z 28 , and Z 29 are each independently selected From: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or the above Z 23 and Z 24 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms with the atoms connected to them, or the above-mentioned Z 28 and Z 29 are connected to each other to form a carbon atom number with their commonly connected atoms A saturated or unsaturated ring of 3-15;
  • K 2 is selected from a single bond, O, S, N (Z 25 ), C (Z 26 Z 27 ), Si (Z 30 Z 31 ); wherein, Z 25 , Z 26 , Z 27 , Z 30 , and Z 31 are each Independently selected from: aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms, alkyl groups having 1 to 10 carbon atoms, or cycloalkyl groups having 3 to 10 carbon atoms , Or the above-mentioned Z 26 and Z 27 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or the above-mentioned Z 30 and Z 31 are connected to each other to form a shared atom with them A saturated or unsaturated ring having 3 to 15 carbon atoms.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of hydrogen or the following groups:
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of hydrogen or the following groups:
  • the Het is an unsubstituted nitrogen-containing heteroaryl group with 3-25 carbon atoms.
  • the Het is an unsubstituted nitrogen-containing heteroaryl group with 3-20 carbon atoms.
  • the X 1 , X 2 and X 3 are each independently selected from CH or N, and at least one is N.
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms; more preferably, L is selected from From a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms.
  • L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted Or unsubstituted fluorenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridylene.
  • the substituents in L are selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 12 carbon atoms, and 3 to 10 carbon atoms. ⁇ cycloalkyl.
  • the substituent in L is selected from deuterium, fluorine, cyano, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, and terphenyl.
  • L is selected from the group consisting of single bonds or groups represented by j-1 to j-14:
  • M 2 is selected from a single bond or Represents a chemical bond
  • Q 1 ⁇ Q 5 and Q '1 ⁇ Q' 5 are each independently selected from N or C (J 5), and in Q 1 ⁇ Q 5 is selected from at least one N; when two or more of Q 1 ⁇ Q 5 when selected from C (J 5), any two J 5 same or different, when Q '1 ⁇ Q' is selected from two or more of C (J 5), any two J 5 identical or different ;
  • Q 6 to Q 13 are each independently selected from N, C or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ), any two J 6 are the same or different;
  • Q 14 to Q 23 are each independently selected from N, C or C (J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C (J 7 ), any two J 7s are the same or different;
  • Q 24 to Q 33 are each independently selected from N, C or C (J 8 ), and at least one of Q 24 to Q 32 is selected from N; when two or more of Q 24 to Q 32 are selected from C (J 8 ), any two J 8s are the same or different;
  • E 1 ⁇ E 14 , J 5 ⁇ J 8 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, heteroaryl group with 3 to 20 carbon atoms, optionally with deuterium, fluorine, chlorine, One or more cyano substituted aryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, arylsilyl groups with 8 to 12 carbon atoms, carbon atoms Alkyl group with 1-10, haloalkyl group with 1-10 carbon atoms, alkenyl group with 2-6 carbon atoms, alkynyl group with 2-6 carbon atoms, and 3-10 carbon atoms Cycloalkyl, heterocycloalkyl with 2 to 10 carbon atoms, cycloalkenyl with 5 to 10 carbon atoms, heterocycloalkenyl with 4 to 10 carbon atoms, and 1 to 10 carbon atoms Alkoxy group, alkylthio group having 1 to 10 carbon
  • E r represents any integer of 1 to 14, E r E r represents the number of substituents; when r is selected from 1,2, When 3, 4, 5, 6, 9, 13, or 14, e r is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e r is selected from 1, 2, 3, 4, 5 or 6; when r is 12, e r is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, e r is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when e r is greater than 1, any two E r are the same or different;
  • K 3 is selected from O, S, Se, N (E 15 ), C (E 16 E 17 ), Si (E 18 E 19 ); wherein, E 15 , E 16 , E 17 , E 18 and E 19 are each independent Is selected from: aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, carbon Alkynyl group with 2-6 atoms, cycloalkyl group with 3-10 carbon atoms, heterocycloalkyl group with 2-10 carbon atoms, cycloalkenyl group with 5-10 carbon atoms, carbon atom number Is a heterocycloalkenyl group of 4 to 10, or E 16 and E 17 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 18 and E 19 are connected to each other to form a saturated or unsaturated ring with carbon atoms
  • K 4 is selected from single bond, O, S, Se, N (E 20 ), C (E 21 E 22 ), Si (E 23 E 24 ); wherein, E 20 to E 24 are each independently selected from: carbon atoms An aryl group having 6 to 20, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and 2 to 6 carbon atoms The alkynyl group, the cycloalkyl group with 3 to 10 carbon atoms, the heterocycloalkyl group with 2 to 10 carbon atoms, the cycloalkenyl group with 5 to 10 carbon atoms, the heterocycloalkenyl group with 4 to 10 carbon atoms Cycloalkenyl, or E 21 and E 22 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 23 and E 24 are connected to each other to form a saturated or unsaturated ring with them
  • L is selected from a single bond or the group consisting of the following groups:
  • L is selected from a single bond or the group consisting of the following groups:
  • the nitrogen-containing compound is selected from the group consisting of the following compounds:
  • the 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 nitrogen-containing compound of the application in combination with the preparation method provided in the synthesis example section.
  • the synthesis example part 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 this application according to these exemplary preparation methods. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Those skilled in the art should not understand limit.
  • the second aspect of the present application provides an electronic component.
  • the electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer contains the first aspect of the present application Of nitrogen-containing compounds.
  • the functional layer includes an electron transport layer, and the electron transport layer contains the nitrogen-containing compound.
  • the electron transport layer can be composed of the nitrogen-containing compound provided in this application, or can be composed of the nitrogen-containing compound provided in this application and other materials.
  • the electron transport may be one layer or more than two layers.
  • the functional layer includes a hole blocking layer, and the hole blocking layer contains the nitrogen-containing compound.
  • the electronic component is an organic electroluminescence device or a photoelectric conversion device.
  • the electronic component is an organic electroluminescent device, such as a blue light device or a green light device.
  • the electronic component may be an organic electroluminescent device.
  • the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer 322, an organic light emitting layer 330 as an energy conversion layer, and a hole blocking layer which are sequentially stacked.
  • the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes into the functional layer.
  • anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ] (PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 321 and the electron blocking layer 322 respectively include one or more hole transport materials.
  • the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types. Compound, this application does not make any special limitation on this.
  • the hole transport layer 321 may be composed of the compound NPB or the compound HT-01
  • the electron blocking layer 322 may include the compound EB-01 or EB-02.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a dopant material.
  • the organic light-emitting layer 330 is composed of a host material and a doping material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, which transfer energy To the host material, the host material transfers energy to the doped material, which in turn enables the doped material to emit light.
  • the host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
  • the host material of the organic light-emitting layer 330 may be BH-01 or a mixed host material, for example, a mixed host material of GH-n1 and GH-n2.
  • the dopant material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not make special limits.
  • the dopant material of the organic light-emitting layer 330 may be BD-01 or Ir(ppy) 3 .
  • the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials.
  • the electron transport materials can be selected from, but not limited to, benzimidazole derivatives and oxadiazole derivatives. , Quinoxaline derivatives or other electron transport materials.
  • the electron transport layer material contains the nitrogen-containing compound of the present application.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates the injection of electrons into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; or multilayer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferable to include a metal electrode containing magnesium and silver as a cathode.
  • a hole injection layer 310 is provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject 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 particularly limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 is provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340.
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic substances.
  • the electron injection layer 350 may include Yb.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed oppositely, 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 photoelectric conversion device may include an anode 100, a hole transport layer 321, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200 which are sequentially stacked and arranged.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the photoelectric conversion layer includes the organic Compound.
  • a third aspect of the present application provides an electronic device, which includes the electronic component described in the second aspect of the present application.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc.
  • the electronic device is a second electronic device 500, and the second electronic device 500 includes the aforementioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • the compounds of the synthesis method not mentioned in this application are all raw material products obtained through commercial channels.
  • Y-2 (32.9g, 272.2mmol), Z-2 (100g, 272.2mmol), tetrakis (triphenylphosphine) palladium (9.4g, 8.2mmol), potassium carbonate (112.8g, 816.5mmol), tetrabutyl Ammonium chloride (0.75g, 2.72mmol), toluene (800mL), ethanol (400mL) and deionized water (200mL) were added to a three-necked flask, heated to 78°C under nitrogen protection, and stirred for 8 hours; the reaction solution was cooled to At room temperature, toluene (300mL) was added for extraction, the organic phases were combined, the organic phases were dried with anhydrous magnesium sulfate, filtered to obtain the filtrate, and the filtrate was concentrated under reduced pressure to obtain the crude product; 1:3) Purify by recrystallization to obtain SM-2 (64.8 g, yield 75%).
  • the magnesium bar (22.9, 944.5 mmol) and ether (250 mL) were placed in a round bottom flask dried under nitrogen protection, and iodine (250 mg) was added. Then, the ether (500mL) solution with SMA-1 (100g, 314.4mmol) dissolved in it was slowly dropped into the flask. After the addition, the temperature was raised to 35°C and stirred for 3 hours; the reaction solution was dropped to 0°C and slowly dropped into it. Add adamantanone (37.8g, 252mmol) in ether (500mL) solution.
  • the intermediate IM-AX was synthesized by the same method as the intermediate IM-A-1, except that SMA-X (50g) was used instead of SMA-1 to prepare the intermediate IM-AX, where X could be 2 ⁇ 12, the prepared intermediate IM-AX is shown in Table 1.
  • intermediate IM-A-1 40g, 102.8mmol
  • trifluoroacetic acid 400mL
  • step on the stirring then gradually raise the temperature to 80°C and reflux for 12h.
  • the intermediate IM-BX was synthesized using the same method as the intermediate IM-B-1, except that the intermediate IM-AX was used instead of the intermediate IM-A-1 to prepare the intermediate IM-BX and the intermediate IM -BX-0, where X can be 2-12, and the prepared intermediate IM-BX is shown in Table 2.
  • the intermediate IM-CX was synthesized using the same method as the intermediate IM-C-1, except that the intermediate IM-BX was used instead of the intermediate IM-B-1 to prepare the intermediate IM-CX and the intermediate IM -CX-0, where X can be 1-12, and the prepared intermediate IM-CX is shown in Table 3.
  • the compound AX was synthesized by the same method as the compound A-1, except that the intermediate IM-CX was used instead of the intermediate IM-C-1, and the raw material M was used instead of the raw material 1 (182918-13-4).
  • Compound AX or B-139 The prepared compounds A-X and B-139 are shown in Table 4.
  • the intermediate IM-DX was synthesized using the same method as the intermediate IM-D-1, except that the intermediate IM-CX was used instead of the intermediate IM-C-1, and SM-X was used instead of SM-b.
  • the compound BY was synthesized using the same method as the compound B-11, except that the intermediate IM-DX was used instead of the intermediate IM-D-1, and the raw material SMX was used instead of the raw material 2 (CAS.NO.:3842-55-5 ) To prepare compound BY.
  • the prepared compound Y is shown in Table 6.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathode, anode, and insulating layer, using ultraviolet ozone and O 2 :N 2 plasma. Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • F4-TCNQ was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and HT-01 is vapor-deposited on the hole injection layer to form a thickness of The hole transport layer.
  • HIL hole injection layer
  • BH-01 and BD-01 were vapor-deposited together at a ratio of 98%: 2% to form a thickness of Organic light emitting layer (EML).
  • EML Organic light emitting layer
  • the compound ET-01 is vapor-deposited to form Thick hole blocking layer (HBL).
  • HBL Thick hole blocking layer
  • Thick electron transport layer ETL
  • EIL electron injection layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1, forming an organic covering layer (CPL), thus completing the manufacture of an organic light-emitting device, the structure is shown in Figure 1.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when preparing the electron transport layer, the nitrogen-containing compound A-1 was replaced with the nitrogen-containing compound shown in Table 9, respectively.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound B-11 of the present application was used instead of the compound ET-01 to form the electron transport layer. At the time, the nitrogen-containing compound A-1 of the present application was replaced by the compound ET-01.
  • the organic electroluminescence device was prepared by the same method as in Example 27, except that when the hole blocking layer was formed, the nitrogen-containing compound B-11 was replaced with the nitrogen-containing compound shown in Table 9, respectively.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound A-1 of the present application was used instead of the compound ET-01 to form the electron transport layer. When the nitrogen-containing compound B-9 is used instead of the nitrogen-containing compound A-1.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound A-5 of the present application was used instead of the compound ET-01 to form the electron transport layer. When the nitrogen-containing compound B-13 is used instead of the nitrogen-containing compound A-1.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound A-14 of the present application was used instead of the compound ET-01 to form the electron transport layer.
  • the nitrogen-containing compound B-23 is used instead of the nitrogen-containing compound A-1.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound A-10 of the present application was used instead of the compound ET-01 to form the electron transport layer.
  • the nitrogen-containing compound B-56 is used instead of the nitrogen-containing compound A-1.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when the hole blocking layer was formed, the nitrogen-containing compound A-201 of the present application was used instead of the compound ET-01 to form the electron transport layer.
  • the nitrogen-containing compound B-102 is used instead of the nitrogen-containing compound A-1.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that the nitrogen-containing compound A-1 was replaced with compound A when preparing the electron transport layer.
  • the organic electroluminescence device was prepared by the same method as in Example 1, except that the nitrogen-containing compound A-1 was replaced with compound B when preparing the electron transport layer.
  • the organic electroluminescent device was prepared by the same method as in Example 1, except that when preparing the electron transport layer, the nitrogen-containing compound A-1 was replaced with Alq3.
  • the organic electroluminescence device was prepared by the same method as in Example 27, except that the nitrogen-containing compound B-11 was replaced with compound A when preparing the hole blocking layer.
  • the organic electroluminescence device was prepared by the same method as in Example 27, except that the nitrogen-containing compound B-11 was replaced with compound B when preparing the hole blocking layer.
  • the organic electroluminescent device was prepared by the same method as in Example 27, except that when preparing the hole blocking layer, the nitrogen-containing compound B-11 was replaced with Alq3.
  • Examples 27-48 when the compound of the present application is used as a hole blocking layer material, compared with Comparative Examples 4-6, the current efficiency and lifetime of the device are significantly improved, and the voltage is reduced by at least 0.21V, and the luminous efficiency is It is increased by at least 7.03%, the external quantum efficiency is increased by at least 7.09%, and the life span is increased by at least 22.4%. Compared with the devices in which L is not a single bond in Examples 27-43, the devices in which L is a single bond in Examples 44-48 have better performances.
  • Example 54 Green organic electroluminescent device
  • the anode is prepared by the following process: the thickness of ITO is 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 a pattern of cathode, anode, and insulating layer. The surface was surfaced with ultraviolet ozone and O 2 :N 2 plasma Treatment to increase the work function of the anode (experimental substrate) and remove dross.
  • F4-TCNQ was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and HT-01 is vapor-deposited on the hole injection layer to form a thickness of The hole transport layer.
  • HIL hole injection layer
  • GH-n1: GH-n2: Ir(ppy) 3 is co-evaporated at a ratio of 50%: 45%: 5% (evaporation rate) to form a thickness of The green organic light-emitting layer (EML).
  • EML green organic light-emitting layer
  • the compound ET-01 is vapor-deposited to form Thick hole blocking layer (HBL).
  • HBL Thick hole blocking layer
  • Thick electron transport layer ETL
  • EIL electron injection layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1, forming an organic covering layer (CPL), thus completing the manufacture of an organic light-emitting device, the structure is shown in Figure 1.
  • the organic electroluminescence device was prepared by the same method as in Example 54, except that when preparing the electron transport layer, the nitrogen-containing compound A-1 was replaced with the nitrogen-containing compound shown in Table 11, respectively.
  • the organic electroluminescent device was prepared by the same method as in Example 54, except that when the hole blocking layer was formed, the nitrogen-containing compound B-9 of the present application was used instead of the compound ET-01 to form the electron transport layer. At the time, the nitrogen-containing compound A-1 of the present application was replaced by the compound ET-01.
  • the organic electroluminescence device was prepared by the same method as in Example 63, except that when the hole blocking layer was formed, the nitrogen-containing compound B-9 was replaced with the nitrogen-containing compound shown in Table 11, respectively.
  • the organic electroluminescence device was prepared by the same method as in Example 54, except that the nitrogen-containing compound A-1 was replaced with compound A when preparing the electron transport layer.
  • the organic electroluminescence device was prepared by the same method as in Example 54, except that the nitrogen-containing compound A-1 was replaced with compound B when preparing the electron transport layer.
  • the organic electroluminescence device was prepared by the same method as in Example 54, except that when preparing the electron transport layer, the nitrogen-containing compound A-1 was replaced with Alq3.
  • the organic electroluminescence device was prepared by the same method as in Example 63, except that the nitrogen-containing compound B-9 was replaced with compound A when preparing the hole blocking layer.
  • the organic electroluminescence device was prepared by the same method as in Example 63, except that the nitrogen-containing compound B-9 was replaced with compound B when preparing the hole blocking layer.
  • the organic electroluminescence device was prepared by the same method as in Example 63, except that when preparing the hole blocking layer, the nitrogen-containing compound B-9 was replaced with Alq3.
  • Examples 63-71 when the compound of the present application is used as a hole blocking layer material, compared with Comparative Examples 10-12, the current efficiency and lifetime of the device are significantly improved, in which the voltage is reduced by at least 0.07V, and the luminous efficiency It is increased by at least 13.4%, the external quantum efficiency is increased by at least 13.4%, and the life span is increased by at least 32.0%.
  • the novel compound of the present application when used to prepare an organic electroluminescent device, the driving voltage of the device can be effectively reduced, and at the same time, the life span of the device can be improved.

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Abstract

本申请涉及一种含氮化合物，所述含氮化合物的结构式如下式 I 所示：其中，环A和环B各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中至少一个选自所述成环碳原子数为10～14的稠合芳环；L选自单键、取代或者未取代的碳原子数为6～30的亚芳基、取代或者未取代的碳原子数为3～30的亚杂芳基；Het为取代或未取代的碳原子数为3～30的含氮杂芳基。本申请的含氮化合物可以提高有机致电发光器件的发光效率，以及提高应用该含氮化合物的光电转化器件的转化效率。

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5月8日递交的申请号为202010383441.X的中国专利申请以及2020年7月27日递交的申请号为202010732484.4的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请属于有机材料技术领域，具体地提供一种含氮化合物以及使用其的电子元件和电子装置。
背景技术
有机发光元件是有机电子元件的代表例。一般而言，有机发光现象是指，利用有机物质使电能转变为光能的现象。利用有机发光现象的有机发光元件通常具有包含阳极和阴极以及位于它们之间的有机物层的结构。其中，为了提高有机发光元件的效率和稳定性，往往由各自不同的物质构成多层结构形成有机物层，例如，有机物层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。对于这样的有机发光元件的结构而言，如果在两级之间施加电压，则空穴从阳极注入至有机物层，电子从阴极注入至有机物层，当所注入的空穴和电子相遇时，形成激子，该激子再次跃迁至基态时，就会发出光。
一般来说，电子传输材料是具有缺电子的含氮杂环基团的化合物，它们大多具有较高的电子亲和势，因而具有较强的接受电子的能力，但是相对于空穴传输材料，例如八羟基喹啉铝等常见的电子传输材料的电子迁移率要远低于空穴传输材料的空穴迁移率，因而在OLED器件中一方面会使载流子的注入和传输不均衡而导致的空穴与电子的复合几率降低，从而降低器件的发光效率，另一方面具有较低电子迁移率的电子传输材料会导致器件的工作电压升高，从而影响功率效率，对能源的节约不利。
发明内容
针对现有技术存在的上述问题，本申请的目的是提供一种含氮化合物以及使用其的电子元件和电子装置，该含氮化合物可用作有机电致发光器件的空穴阻挡层和/或电子传输层。
本申请第一方面提供一种含氮化合物，所述含氮化合物的结构式如式1所示：
Figure PCTCN2021090725-appb-000001
其中，环A和环B相同或不同，且各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中至少一个为所述成环碳原子数为10～14的稠合芳环；
L选自单键、取代或者未取代的碳原子数为6～30的亚芳基、取代或者未取代的碳原子数为 3～30的亚杂芳基；
各Q 1和各Q 2相同或不同，各自独立地选自：氘、卤素基团、氰基、碳原子数为1～10的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、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6～12的芳基、碳原子数为7～13的芳烷基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
n表示Q 1的个数，选自0或1；m表示Q 2的个数，选自0或1；
Het为取代或未取代的碳原子数为3～30的含氮杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自氢、取代或未取代的碳原子数为1～20的烷基、取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～30的芳基、取代或未取代的碳原子数为3～30的杂芳基；
所述L、Het、Ar 1和Ar 2中的取代基相同或者不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6～25的芳基、碳原子数为3～25的杂芳基、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3～10的环烷基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基。
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传输层，所述电子传输层包括所述含氮化合物；优选地，所述功能层包括空穴阻挡层，所述空穴阻挡层包括所述含氮化合物。
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。
通过上述技术方案，本申请提供的含氮化合物具有杂芳基与稠环并金刚烷芴结合的分子结构。该分子结构一方面可减小能级注入壁垒，进而降低有机电致发光器件的工作电压，提高光电转化器件的开路电压。另一方面该分子结构具有大的分子量，且稠环结构可以增加空间位阻，从而调整结构，使材料不易结晶或聚集，使得材料在电子元件中具有更好的寿命。不仅如此，该分子结构具有富电子特性，整个分子的极性增强，更有利于材料分子的方向性排列，从而增强电子的注入和传输，增强电子传输材料的电子传导率，同时可以提高应用该含氮化合物的有机致电发光器件的发光效率，以及提高应用该含氮化合物的光电转化器件的转化效率。
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。在附图中：
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的结构示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；330、有机发光层；341、空穴阻挡层、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。
本申请第一方面提供一种含氮化合物，所述含氮化合物的结构式如式1所示：
Figure PCTCN2021090725-appb-000002
其中，环A和环B相同或不同，且各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中至少一个为所述成环碳原子数为10～14的所述稠合芳环；
L连接环A或环B；
具体地，在本申请中，式1所示的含氮化合物可以选自式A或式B所示的化合物；
Figure PCTCN2021090725-appb-000003
当环A或环B上带有取代基Q 1或Q 2时，L只与环A和环B本身连接。
L选自单键、取代或者未取代的碳原子数为6～30的亚芳基、取代或者未取代的碳原子数为3～30的亚杂芳基；
各Q 1和各Q 2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的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、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6～12的芳基、碳原子数为7～13的芳烷基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
n表示Q 1的个数，选自0或1；m表示Q 2的个数，选自0或1；
Het为取代或未取代的碳原子数为3～30的含氮杂芳基；
Ar 1和Ar 2相同或不同，且各自独立地选自：氢、取代或未取代的碳原子数为1～20的烷基、取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～30的芳基、取代或未取代的碳原子数为3～30的杂芳基；
所述L、Het、Ar 1和Ar 2中的取代基相同或者不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6～25的芳基、碳原子数为3～25的杂芳基、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3～10的环烷基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基。在本申请中，“Het可以为取代或未取代的碳原子数为3～30的含氮杂芳基”，指的是Het可以包含取代基，也可以不包含取代基。当Het包含取代基时，Het中的取代基指的是除Ar 1和Ar 2之外的取代基。
在本申请中，环A和环B相同或不同，各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，该稠和芳环可以为萘环、蒽环、菲环。
优选地，在本申请中，环A或环B为苯基；L与苯基相连接。
本申请提供的含氮化合物，以杂芳基与稠环并金刚烷芴结合的分子结构。该分子结构一方面可 减小能级注入壁垒，进而降低有机电致发光器件的工作电压，提高光电转化器件的开路电压。另一方面该分子结构具有大的分子量，增加分子不对称性，可以调整结构，使材料不易结晶或聚集，使得材料在电子元件中具有更好的寿命。不仅如此，该分子结构其具有富电子特性，整个分子的极性增强，更有利于材料分子的方向性排列，从而增强电子的注入和传输。此外，稠环结构能够增强电子传输材料的电子传导率，同时可以提高应用该含氮化合物的有机致电发光器件的发光效率，以及提高应用该含氮化合物的光电转化器件的转化效率。
在本申请一种实施方式中，所述式1所示的含氮化合物的结构式选自如下式2至19组成的组：
Figure PCTCN2021090725-appb-000004
Figure PCTCN2021090725-appb-000005
在本申请一种实施方式中，所述式1所示的含氮化合物的结构式选自如下式20至28组成的组：
Figure PCTCN2021090725-appb-000006
Figure PCTCN2021090725-appb-000007
在本申请中，由于金刚烷是立体结构，在化合物结构图中，因为绘图角度不同，会呈现不同的平面形状，环戊烷上所形成的环状结构均为金刚烷，并且连接位置也是相同的。例如：以下结构
Figure PCTCN2021090725-appb-000008
均为同一种结构。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2021090725-appb-000009
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、碳原子数为6～25的芳基、碳原子数为3～25的杂芳基、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3～10的环烷基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基。在本申请中，“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若Ar 1选自取代的碳原子数为30的芳基，则芳基及其上的取代基的所有碳原子数为30。
在本申请中，L、Ar 1、Ar 2、Het的碳原子数，指的是所有碳原子数。举例而言：L为取代的碳 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 PCTCN2021090725-appb-000010
则其碳原子数为7；L为
Figure PCTCN2021090725-appb-000011
其碳原子数为12。
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言，在本申请中，苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021090725-appb-000012
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，稠合芳环是指两个或两个以上芳环或杂芳环以共有环边而形成的多芳环，例如萘、蒽、菲、芘。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。
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，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、吩噻嗪基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
在本申请中，含氮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，且至少具有一个N。
本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代 的吡啶基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，碳原子数为1～20的烷基可以为直链烷基或支链烷基。具体而言，碳原子数为1～20的烷基可以为碳原子数1至20的直链烷基，或碳原子数3至20的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20。碳原子数为1～20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，卤素基团可以为氟、氯、溴、碘。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021090725-appb-000013
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。
举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式。
Figure PCTCN2021090725-appb-000014
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2021090725-appb-000015
在本申请的一种具体实施方式中，所述环A和环B相同或者不同，且各自独立地选自苯环、萘环、菲环和蒽环，且环A和环B不同时为苯环。
在本申请一种具体实施方式中，
Figure PCTCN2021090725-appb-000016
选自如下所示的结构所组成的组：
Figure PCTCN2021090725-appb-000017
其中，
Figure PCTCN2021090725-appb-000018
表示上述结构用于与
Figure PCTCN2021090725-appb-000019
连接的化学键，
Figure PCTCN2021090725-appb-000020
表示上述结构用于与
Figure PCTCN2021090725-appb-000021
连接的化学键。
在本申请一种具体实施方式中，
Figure PCTCN2021090725-appb-000022
中，n＝1且
Figure PCTCN2021090725-appb-000023
选自如下所示的结构所组成的组：
Figure PCTCN2021090725-appb-000024
其中，
Figure PCTCN2021090725-appb-000025
表示上述结构中用于与
Figure PCTCN2021090725-appb-000026
连接的化学键，
Figure PCTCN2021090725-appb-000027
表示上述结构中用于与
Figure PCTCN2021090725-appb-000028
连接的化学键。
在本申请一种具体实施方式中，
Figure PCTCN2021090725-appb-000029
选自如下所示的结构所组成的组：
Figure PCTCN2021090725-appb-000030
其中，
Figure PCTCN2021090725-appb-000031
表示上述结构中用于与
Figure PCTCN2021090725-appb-000032
连接的化学键，
Figure PCTCN2021090725-appb-000033
表示上述结构中用于与
Figure PCTCN2021090725-appb-000034
连接的化学键。
在本申请一种具体实施方式中，
Figure PCTCN2021090725-appb-000035
中，m＝1且
Figure PCTCN2021090725-appb-000036
选自如下所示的结构所组成的组：
Figure PCTCN2021090725-appb-000037
其中，
Figure PCTCN2021090725-appb-000038
表示上述结构中用于与
Figure PCTCN2021090725-appb-000039
连接的化学键，
Figure PCTCN2021090725-appb-000040
表示上述结构中用于与
Figure PCTCN2021090725-appb-000041
连接的化学键。
在本申请一种具体实施方式中，所述Ar 1和Ar 2相同或不同，且分别独立地选自氢、取代或未 取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为6～24的芳基、取代或未取代的碳原子数为5～24的杂芳基。
可选地，在本申请中，所述Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6～21的芳基、取代或未取代的碳原子数为5～20的杂芳基。
优选地，在本申请中，所述Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6～20的芳基、取代或未取代的碳原子数为5～12的杂芳基。
在本申请一种具体实施方式中，所述Ar 1和Ar 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6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～5的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、碳原子数为3～7的三烷基硅基、碳原子数为18～24的三芳基硅基。具体地，Ar 1和Ar 2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、叔丁基、苯基、萘基、联苯基、三联苯基、二甲基芴基、N-苯基咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、吡啶基、嘧啶基、吩噻嗪基、吩噁嗪基。
在本申请一种具体实施方式中，Ar 1和Ar 2相同或者不同，且分别独立地选自氢或如下i-1至i-15所示的基团所组成的组：
Figure PCTCN2021090725-appb-000042
其中，M 1选自单键或者
Figure PCTCN2021090725-appb-000043
G 1～G 5和G 1’～G 4’各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、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18～24的三芳基硅基；
Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、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1～10的烷硫基、碳原子数为3～18的杂芳基、碳原子数为18～24的三芳基硅基；
Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被一个或多个氘、氟、氯、氰基取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18～24的三芳基硅基；在本申请中，“任选地被一个或多个氘、氟、氯、氰基取代的碳原子数为6～18的芳基”是指芳基可以被氘、氟、氯、氰基取代，也可以不被氘、氟、氯、氰基取代。
h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
在本申请一种具体实施方式中，Ar 1和Ar 2相同或者不同，且分别独立地选自氢或以下基团组成的组：
Figure PCTCN2021090725-appb-000044
Figure PCTCN2021090725-appb-000045
在本申请一种具体实施方式中，Ar 1和Ar 2相同或者不同，且分别独立地选自氢或以下基团组成的组：
Figure PCTCN2021090725-appb-000046
Figure PCTCN2021090725-appb-000047
Figure PCTCN2021090725-appb-000048
Figure PCTCN2021090725-appb-000049
在本申请一种具体实施方式中，所述Het为未取代的碳原子数为3～25的含氮杂芳基。
优选地，在本申请中，所述Het为未取代的碳原子数为3～20的含氮杂芳基。
在本申请的一种具体实施方式中，式1中，
Figure PCTCN2021090725-appb-000050
选自以下基团：
Figure PCTCN2021090725-appb-000051
Figure PCTCN2021090725-appb-000052
其中，
Figure PCTCN2021090725-appb-000053
表示化学键。
在本申请一种具体实施方式中，
Figure PCTCN2021090725-appb-000054
选自以下基团所组成的组：
Figure PCTCN2021090725-appb-000055
Figure PCTCN2021090725-appb-000056
Figure PCTCN2021090725-appb-000057
其中，以上含有X 1，X 2，X 3的基团中，所述X 1、X 2和X 3分别独立地选自CH或N，且至少一个为N。
在本申请中，L选自单键、取代或未取代的碳原子数为6～20的亚芳基、取代或未取代的碳原子数为3～20的亚杂芳基。
优选地，L选自单键、取代或未取代的碳原子数为6～18的亚芳基、取代或未取代的碳原子数为3～18的亚杂芳基；更优选地，L选自单键、取代或未取代的碳原子数为6～15的亚芳基、取代或未取代的碳原子数为5～12的亚杂芳基。
在本申请中，L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、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚吡啶基。
在本申请中，L中的取代基选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～10的环烷基。具体地，在本申请中，L中的取代基选自氘、氟、氰基、甲基、乙基、叔丁基、苯基、萘基、联苯基、三联苯基。
在本申请中，L选自单键或j-1至j-14所示基团所组成的组：
Figure PCTCN2021090725-appb-000058
Figure PCTCN2021090725-appb-000059
其中，M 2选自单键或者
Figure PCTCN2021090725-appb-000060
Figure PCTCN2021090725-appb-000061
表示化学键；
Q 1～Q 5和Q’ 1～Q’ 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 32中至少一个选自N；当Q 24～Q 32中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
E 1～E 14、J 5～J 8各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被氘、氟、氯、氰基取代的一个或多个的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为8～12的芳基甲硅烷基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基，碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基，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的磷氧基，碳原子数为18～24的三芳基硅基；在本申请中，“任选地被氘、氟、氯、氰基取代的一个或多个的碳原子数为6～20的芳基”是指指芳基可以被氘、氟、氯、氰基取代，也可以不被氘、氟、氯、氰基取代。
e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
在本申请一种具体实施方式中，L选自单键或者如下基团所组成的组：
Figure PCTCN2021090725-appb-000062
在本申请一种具体实施方式中，L选自单键或者如下基团所组成的组：
Figure PCTCN2021090725-appb-000063
Figure PCTCN2021090725-appb-000064
在本申请一种具体实施方式中，所述含氮化合物选自以下化合物所组成的组：
Figure PCTCN2021090725-appb-000065
Figure PCTCN2021090725-appb-000066
Figure PCTCN2021090725-appb-000067
Figure PCTCN2021090725-appb-000068
Figure PCTCN2021090725-appb-000069
Figure PCTCN2021090725-appb-000070
Figure PCTCN2021090725-appb-000071
Figure PCTCN2021090725-appb-000072
Figure PCTCN2021090725-appb-000073
Figure PCTCN2021090725-appb-000074
Figure PCTCN2021090725-appb-000075
Figure PCTCN2021090725-appb-000076
Figure PCTCN2021090725-appb-000077
Figure PCTCN2021090725-appb-000078
Figure PCTCN2021090725-appb-000079
Figure PCTCN2021090725-appb-000080
Figure PCTCN2021090725-appb-000081
Figure PCTCN2021090725-appb-000082
Figure PCTCN2021090725-appb-000083
Figure PCTCN2021090725-appb-000084
Figure PCTCN2021090725-appb-000085
Figure PCTCN2021090725-appb-000086
Figure PCTCN2021090725-appb-000087
Figure PCTCN2021090725-appb-000088
Figure PCTCN2021090725-appb-000089
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实施例部分提供的制备方法确定合适的合成方法。换言之，本申请的合成实施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，该电子元件包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层含有本申请第一方面所述的含氮化合物。
在一种具体的实施方式中，所述功能层包括电子传输层，所述电子传输层含有所述含氮化合物。电子传输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。所述电子传输可以为一层或两层以上。
在一种具体的实施方式中，所述功能层包括空穴阻挡层，所述空穴阻挡层含有所述含氮化合物。
在一种具体实施方式中，所述电子元件为有机电致发光器件或光电转化器件。
在一种具体实施方式中，所述电子元件为有机电致发光器件，例如为蓝光器件或绿光器件。
在一种具体实施方式中，电子元件可以为有机电致发光器件。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴注入层310、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、空穴阻挡层341、电子传输层340、电子注入层350、和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层321和电子阻挡层322分别包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。例如，空穴传输层321可以由化合物NPB或化合物HT-01组成，电子阻挡层322可以包含化合物EB-01或EB-02。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和掺杂材料。可选地，有机发光层330由主体材料和掺杂材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给掺杂材料，进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。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BH-01或混合型主体材料，例如：GH-n1与GH-n2混合主体材料。
有机发光层330的掺杂材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的掺杂材料可以为BD-01或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，电子传输层材料含有本申请的含氮化合物。
本申请中，EB-01、EB-02、BH-01、BD-01、GH-n1、GH-n2和ET-01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Yb。
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。
按照一种具体的实施方式，如图3所示，光电转化器件可包括依次层叠设置的阳极100、空穴传输层321、光电转化层360、电子传输层340和阴极200。
可选地，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、光电转化层、电子传输层和阴极，其中，光电转化层包含有本申请的有机化合物。
本申请第三方面提供一种电子装置，该电子装置包含本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
下面结合合成实施例来具体说明本申请的有机化合物的合成方法，但是本申请并不因此而受到任何限制。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
本申请中的中间体和化合物的分析检测使用ICP-7700质谱仪和M5000元素分析仪。
合成实施例
Figure PCTCN2021090725-appb-000090
将Y-1(100g,398.5mmol)、Z-1(96.3g,398.5mmol)、四(三苯基膦)钯(2.3g,1.9mmol)、碳酸钾(110.2g,797.1mmol)、四丁基氯化铵(0.55g,1.9mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷体系(体积比1：3)进行重结晶提纯，得到SM-1(112.8g，收率77％)。
Figure PCTCN2021090725-appb-000091
将Y-2(32.9g,272.2mmol)、Z-2(100g,272.2mmol)、四(三苯基膦)钯(9.4g,8.2mmol)、碳酸钾(112.8g,816.5mmol)、四丁基氯化铵(0.75g,2.72mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用二氯甲烷/正庚烷体系(体积比1:3)进行重结晶提纯，得到SM-2(64.8g，收率75％)。
Figure PCTCN2021090725-appb-000092
将Y-3(100g,350.5mmol)、Z-3(71.5g,350.5mmol)、四(三苯基膦)钯(12.1g,10.5mmol)、碳酸钾(145.3g,1051.5mmol)、四丁基氯化铵(0.97g,3.5mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(300mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷体系(体积比1：3)进行重结晶提纯，得到SM-3(82.4g，收率74％)。
Figure PCTCN2021090725-appb-000093
将镁条(22.9,944.5mmol)和乙醚(250mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(250mg)。而后将溶有SMA-1(100g,314.4mmol)的乙醚(500mL)溶液缓慢滴入烧瓶中，滴加完毕后升温 至35℃，搅拌3小时；将反应液降至0℃，向其中缓慢滴入溶有金刚烷酮(37.8g，252mmol)的乙醚(500mL)溶液，滴加完毕后升温至35℃，搅拌6小时；将反应液冷却至室温，向其中加入5％盐酸至pH<7，搅拌1小时，加入乙醚(500mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到固体中间体IM-A-1(97.8g,收率80％)。
采用合成与中间体IM-A-1相同的方法合成中间体IM-A-X，不同之处在于，使用SMA-X(50g)代替SMA-1来制备中间体IM-A-X，其中，X可为2～12，制得的中间体IM-A-X如表1所示。
表1
Figure PCTCN2021090725-appb-000094
Figure PCTCN2021090725-appb-000095
Figure PCTCN2021090725-appb-000096
向反应瓶中，加入中间体IM-A-1(40g,102.8mmol)，三氟乙酸(400mL)，开启搅拌，然后逐渐升温至80℃回流反应12h，反应完成后，将反应液倒入水中(体积比1：20)，搅拌30min后过滤，用水(体积比1：2)淋洗，用乙醇淋洗(体积比1：2)，后得到粗品用体积比二氯甲烷：正庚烷＝1：2重结晶，得到中间体IM-B-1(30.5g，收率：80％)。
采用与合成中间体IM-B-1相同的方法合成中间体IM-B-X，不同之处在于，使用中间体IM-A-X代替中间体IM-A-1来制备中间体IM-B-X和中间体IM-B-X-0，其中，X可为2～12，制得的中间体IM-B-X如表2所示。
表2
Figure PCTCN2021090725-appb-000097
Figure PCTCN2021090725-appb-000098
Figure PCTCN2021090725-appb-000099
Figure PCTCN2021090725-appb-000100
向反应瓶中投入中间体IM-B-1(15g，40.4mmol)、联硼酸频哪醇酯(10.3g，40.4mmol)、三(二亚苄基丙酮)二钯(0.74g，0.81mmol)、2-二环己基磷-2,4,6-三异丙基联苯(0.19g，0.40mmol)、醋酸钾(7.9g，80.8mmol)和1,4-二氧六环(150mL)，氮气保护下升温至110℃，加热回流搅拌5h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，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(体积比1:3)体系对粗品进行重结晶提纯，得到中间体IM-C-1(14.0g，收率为：75％)。
采用与合成中间体IM-C-1相同的方法合成中间体IM-C-X，不同之处在于，使用中间体IM-B-X代替中间体IM-B-1来制备中间体IM-C-X和中间体IM-C-X-0，其中，X可为1～12，制得的中间体IM-C-X如表3所示。
表3
Figure PCTCN2021090725-appb-000101
Figure PCTCN2021090725-appb-000102
Figure PCTCN2021090725-appb-000103
Figure PCTCN2021090725-appb-000104
Figure PCTCN2021090725-appb-000105
向反应瓶中投入中间体IM-C-1(5.00g，10.8mmol)、原料1(CAS.NO.:182918-13-4)(5.46g，13.0mmol)、醋酸钯(0.12g，0.54mmol)、2-二环己基磷-2,4,6-三异丙基联苯(0.26g，0.54mmol)、碳酸钾(3.29g，23.8mmol)和甲苯(40mL)、乙醇(20mL)和水(10mL)，氮气保护下升温至78℃，加热回流搅拌5h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，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(体积比1:3)体系对粗品进行重结晶提纯，得到化合物A-1(6.24g，收率为：80％)。质谱为：m/z＝720.3[M+H] +。
采用与合成化合物A-1的相同的方法合成化合物A-X，不同之处在于，使用中间体IM-C-X代替中间体IM-C-1、使用原料M代替原料1(182918-13-4)来制备化合物A-X或B-139。制得的化合物A-X和B-139如表4所示。
表4
Figure PCTCN2021090725-appb-000106
Figure PCTCN2021090725-appb-000107
Figure PCTCN2021090725-appb-000108
Figure PCTCN2021090725-appb-000109
Figure PCTCN2021090725-appb-000110
Figure PCTCN2021090725-appb-000111
向反应瓶中投入中间体IM-C-1(5.00g，10.8mmol)、SM-b(182918-13-4)(4.66g，13.0mmol)、醋酸钯(0.12g，0.54mmol)、2-二环己基磷-2,4,6-三异丙基联苯(0.26g，0.54mmol)、碳酸钾(3.29g，23.8mmol)和甲苯(40mL)、乙醇(20mL)和水(10mL)，氮气保护下升温至78℃，加热回流搅拌5h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，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(体积比1:3)体系对粗品进行重结晶提纯，得到中间体IM-D-1(4.91g，收率为：80％)。
采用与中间体IM-D-1的合成方法相同的方法合成中间体IM-D-X，不同之处在于，使用中间体IM-C-X代替中间体IM-C-1、SM-X代替SM-b来制备中间体IM-D-X。其中，X可为2～19，制得的中间体IM-D-X如表5所示。
表5
Figure PCTCN2021090725-appb-000112
Figure PCTCN2021090725-appb-000113
Figure PCTCN2021090725-appb-000114
Figure PCTCN2021090725-appb-000115
Figure PCTCN2021090725-appb-000116
Figure PCTCN2021090725-appb-000117
向反应瓶中投入中间体IM-D-1(4.00g，7.05mmol)、四氢呋喃(40mL),氮气环境下降温至-78℃，滴加正丁基锂(0.52g，8.10mmol)，滴加完毕后在该温度下保温1h后滴加原料2(1.88g，7.05mmol)，后继续保温1h，自然升温至室温反应12h。反应液中有固体析出，用布氏漏斗过滤后得到粗品，使用甲苯(150mL)体系对粗品进行重结晶提纯，得到化合物B-11(3.24，收率为：64％)。质谱为：m/z＝720.3[M+H] +。
采用与合成化合物B-11相同的方法合成化合物B-Y，不同之处在于，使用中间体IM-D-X代替中间体IM-D-1、原料SMX代替原料2(CAS.NO.:3842-55-5)来制备化合物B-Y。制得的化合物Y如表6所示。
表6
Figure PCTCN2021090725-appb-000118
Figure PCTCN2021090725-appb-000119
Figure PCTCN2021090725-appb-000120
Figure PCTCN2021090725-appb-000121
Figure PCTCN2021090725-appb-000122
部分化合物核磁数据如下表7所示
表7
Figure PCTCN2021090725-appb-000123
采用以下方法进行有机电致发光器件的制作：
实施例1 蓝色有机电致发光器件
通过以下过程制备阳极：将厚度为
Figure PCTCN2021090725-appb-000124
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2：N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
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 PCTCN2021090725-appb-000125
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021090725-appb-000126
的空穴传输层。
在空穴传输层上真空蒸镀EB-01，形成厚度为
Figure PCTCN2021090725-appb-000127
的电子阻挡层。
在电子阻挡层上，将BH-01和BD-01以98％：2％的比例进行共同蒸镀，形成厚度为
Figure PCTCN2021090725-appb-000128
的有机发光层(EML)。
在有机发光层上，将化合物ET-01蒸镀形成了
Figure PCTCN2021090725-appb-000129
厚的空穴阻挡层(HBL)。
在空穴阻挡层上，将化合物A-1和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021090725-appb-000130
厚的电子传输层(ETL)。
将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021090725-appb-000131
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以 1：10的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021090725-appb-000132
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021090725-appb-000133
的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造，结构如图1所示。
实施例2～26
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1分别更换为表9中所示的含氮化合物。
实施例27
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物B-11代替化合物ET-01，在形成电子传输层时，以化合物ET-01代替本申请的含氮化合物A-1。
实施例28～实施例48
采用与实施例27相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，将含氮化合物B-11分别更换为表9中所示的含氮化合物。
实施例49
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物A-1代替化合物ET-01，在形成电子传输层时，以含氮化合物B-9代替含氮化合物A-1。
实施例50
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物A-5代替化合物ET-01，在形成电子传输层时，以含氮化合物B-13代替含氮化合物A-1。
实施例51
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物A-14代替化合物ET-01，在形成电子传输层时，以含氮化合物B-23代替含氮化合物A-1。
实施例52
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物A-10代替化合物ET-01，在形成电子传输层时，以含氮化合物B-56代替含氮化合物A-1。
实施例53
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物A-201代替化合物ET-01，在形成电子传输层时，以含氮化合物B-102代替含氮化合物A-1。
比较例1
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为化合物A。
比较例2
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为化合物B。
比较例3
采用与实施例1相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为Alq3。
比较例4
采用与实施例27相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-11更换为化合物A。
比较例5
采用与实施例27相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-11更换为化合物B。
比较例6
采用与实施例27相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-11更换为Alq3。
对比例中所采用的化合物及化合物ET-01的结构见表8。
表8
Figure PCTCN2021090725-appb-000134
对如上制得的有机电致发光器件，分析了在10A/cm 2的条件下器件的光电性能，和20mA/cm 2的条件下器件的光电性能，其结果示于下表9：
表9
Figure PCTCN2021090725-appb-000135
Figure PCTCN2021090725-appb-000136
Figure PCTCN2021090725-appb-000137
由上表9可知，实施例1-26将本申请化合物用作电子传输层材料时，与比较例1-3相比，对于器件的电流效率和寿命有着较为明显的改善，其中电压至少降低了0.15V，发光效率至少提高了6.72％，外量子效率至少提高了6.73％，寿命至少提高了26.39％。其中，实施例1-17中L为单键的化合物的器件与实施18-22中L不为单键的化合物的器件相比较，各项性能更优异。
实施例27-48将本申请化合物用作空穴阻挡层材料时，与比较例4-6相比，对于器件的电流效率和寿命有着较为明显的改善，其中电压至少降低了0.21V，发光效率至少提高了7.03％，外量子效率至少提高了7.09％，寿命至少提高了22.4％。其中实施例27-43中L不为单键的化合物的器件与实施例44-48中L为单键的化合物的器件相比较，各项性能更优异。
实施例49-53将本申请化合物同时组合作为空穴阻挡层和电子传输层时与比较例1-6相比，电压降低较为明显，至少降低了0.35V，发光效率至少提高了10.94％，外量子效率至少提高了10.97％，寿命至少提高了29.86％。
实施例54：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 PCTCN2021090725-appb-000138
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 PCTCN2021090725-appb-000139
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021090725-appb-000140
的空穴传输层。
在空穴传输层上真空蒸镀EB-02，形成厚度为
Figure PCTCN2021090725-appb-000141
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 PCTCN2021090725-appb-000142
的绿色有机发光层(EML)。
在有机发光层上，将化合物ET-01蒸镀形成了
Figure PCTCN2021090725-appb-000143
厚的空穴阻挡层(HBL)。
在空穴阻挡层上，将化合物A-1和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021090725-appb-000144
厚的电子传输层(ETL)。
将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021090725-appb-000145
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1：10的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2021090725-appb-000146
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021090725-appb-000147
的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造，结构如图1所示。
实施例55～62
采用与实施例54相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1分别更换为表11中所示的含氮化合物。
实施例63
采用与实施例54相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，以本申请的含氮化合物B-9代替化合物ET-01，在形成电子传输层时，以化合物ET-01代替本申请的含氮化合物A-1。
实施例64～实施例71
采用与实施例63相同的方法制备有机电致发光器件，不同之处仅在于，在形成空穴阻挡层时，将含氮化合物B-9分别更换为表11中所示的含氮化合物。
比较例7
采用与实施例54相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为化合物A。
比较例8
采用与实施例54相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为化合物B。
比较例9
采用与实施例54相同的方法制备有机电致发光器件，不同之处仅在于，在制备电子传输层时，将含氮化合物A-1更换为Alq3。
比较例10
采用与实施例63相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-9更换为化合物A。
比较例11
采用与实施例63相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-9更换为化合物B。
比较例12
采用与实施例63相同的方法制备有机电致发光器件，不同之处仅在于，在制备空穴阻挡层时，将含氮化合物B-9更换为Alq3。
所使用的各个材料的结构式如下表10所示：
表10
Figure PCTCN2021090725-appb-000148
Figure PCTCN2021090725-appb-000149
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11：
表11 有机电致发光器件的性能测试结果
Figure PCTCN2021090725-appb-000150
Figure PCTCN2021090725-appb-000151
根据上表11可知，实施例54-62将本申请化合物用作电子传输层材料时，与比较例7-9相比，对于器件的电流效率和寿命有着较为明显的改善，其中电压至少降低了0.10V，发光效率至少提高了14.5％，外量子效率至少提高了14.5％，寿命至少提高了30.3％。
实施例63-71将本申请化合物用作空穴阻挡层材料时，与比较例10-12相比，对于器件的电流效率和寿命有着较为明显的改善，其中电压至少降低了0.07V，发光效率至少提高了13.4％，外量子效率至少提高了13.4％，寿命至少提高了32.0％。
因此，本申请的新型化合物用于制备有机电致发光器件时，可以有效地降低器件的驱动电压，同时对器件寿命也有提升效果。
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。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合，为了避免不必要的重复，本申请对各种可能的组合方式不再另行说明。
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 (22)

  1. 一种含氮化合物，其特征在于，所述含氮化合物的结构式如式1所示：
    Figure PCTCN2021090725-appb-100001
    其中，环A和环B相同或不同，且各自独立地选自苯环或者成环碳原子数为10～14的稠合芳环，且环A和环B中至少一个为所述成环碳原子数为10～14的稠合芳环；
    L选自单键、取代或者未取代的碳原子数为6～30的亚芳基、取代或者未取代的碳原子数为3～30的亚杂芳基；
    各Q 1和各Q 2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的卤代烷基、碳原子数为1～10的烷基、碳原子数为3～15的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、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6～12的芳基、碳原子数为7～13的芳烷基、碳原子数为4～12的杂芳基、碳原子数为5～13的杂芳烷基；
    n表示Q 1的个数，选自0或1；m表示Q 2的个数，选自0或1；
    Het为取代或未取代的碳原子数为3～30的含氮杂芳基；
    Ar 1和Ar 2相同或不同，且各自独立地选自：氢、取代或未取代的碳原子数为1～20的烷基、取代或未取代的碳原子数为3～20的环烷基、取代或未取代的碳原子数为6～30的芳基、取代或未取代的碳原子数为3～30的杂芳基；
    所述L、Het、Ar 1和Ar 2中的取代基相同或者不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6～25的芳基、碳原子数为3～25的杂芳基、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3～10的环烷基、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3～12的三烷基硅基、碳原子数为18～24的三芳基硅基。
  2. 根据权利要求1所述的含氮化合物，其特征在于，所述环A和环B相同或不同，且各自独立地选自苯环、萘环、菲环和蒽环，且环A和环B不同时为苯环。
  3. 根据权利要求1所述的含氮化合物，其特征在于，所述式1所示的含氮化合物的结构式选自如下式2至19组成的组：
    Figure PCTCN2021090725-appb-100002
    Figure PCTCN2021090725-appb-100003
  4. 根据权利要求1所述的含氮化合物，其特征在于，所述式1所示的含氮化合物的结构式选自如下式20至28组成的组：
    Figure PCTCN2021090725-appb-100004
  5. 根据权利要求1所述的含氮化合物，其特征在于，式1中，
    Figure PCTCN2021090725-appb-100005
    选自以下基团：
    Figure PCTCN2021090725-appb-100006
    其中，
    Figure PCTCN2021090725-appb-100007
    表示化学键。
  6. 根据权利要求1所述的含氮化合物，其特征在于，
    Figure PCTCN2021090725-appb-100008
    选自如下所示的结构所组成的组：
    Figure PCTCN2021090725-appb-100009
    其中，
    Figure PCTCN2021090725-appb-100010
    表示上述结构用于与
    Figure PCTCN2021090725-appb-100011
    连接的化学键，
    Figure PCTCN2021090725-appb-100012
    表示上述结构用于与
    Figure PCTCN2021090725-appb-100013
    连接的化学键。
  7. 根据权利要求1所述的含氮化合物，其特征在于，
    Figure PCTCN2021090725-appb-100014
    中，n＝1且
    Figure PCTCN2021090725-appb-100015
    选自如下所示的结构所组成的组：
    Figure PCTCN2021090725-appb-100016
    其中，
    Figure PCTCN2021090725-appb-100017
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100018
    连接的化学键，
    Figure PCTCN2021090725-appb-100019
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100020
    连接的化学键。
  8. 根据权利要求1所述的含氮化合物，其特征在于，
    Figure PCTCN2021090725-appb-100021
    选自如下所示的结构所组成的组：
    Figure PCTCN2021090725-appb-100022
    其中，
    Figure PCTCN2021090725-appb-100023
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100024
    连接的化学键，
    Figure PCTCN2021090725-appb-100025
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100026
    连接的化学键。
  9. 根据权利要求1所述的含氮化合物，其特征在于，
    Figure PCTCN2021090725-appb-100027
    中，m＝1且
    Figure PCTCN2021090725-appb-100028
    选自如下所示的结构所组成的组：
    Figure PCTCN2021090725-appb-100029
    Figure PCTCN2021090725-appb-100030
    其中，
    Figure PCTCN2021090725-appb-100031
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100032
    连接的化学键，
    Figure PCTCN2021090725-appb-100033
    表示上述结构中用于与
    Figure PCTCN2021090725-appb-100034
    连接的化学键。
  10. 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相同或不同，且分别独立地选自氢、取代或未取代的碳原子数为1～10的烷基、取代或未取代的碳原子数为3～10的环烷基、取代或未取代的碳原子数为6～24的芳基、取代或未取代的碳原子数为5～24的杂芳基。
  11. 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6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～5的烷基、碳原子数为1～4的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～4的烷氧基、碳原子数为1～4的烷硫基、碳原子数为3～7的三烷基硅基、碳原子数为18～24的三芳基硅基；
    优选地，所述Ar 1和Ar 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、叔丁基、苯基、萘基、联苯基、三联苯基、二甲基芴基、N-苯基咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、吡啶基、嘧啶基、吩噻嗪基、吩噁嗪基。
  12. 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相同或者不同，且分别独立地选自氢或如下i-1至i-15所示的基团：
    Figure PCTCN2021090725-appb-100035
    Figure PCTCN2021090725-appb-100036
    其中，M 1选自单键或者
    Figure PCTCN2021090725-appb-100037
    G 1～G 5和G 1’～G 4’各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
    G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
    G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
    G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
    Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、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18～24的三芳基硅基；
    Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、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1～10的烷硫基、碳原子数为3～18的杂芳基、碳原子数为18～24的三芳基硅基；
    Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被一个或多个氘、氟、氯、氰基取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18～24的三芳基硅基；
    h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
    K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不 饱和的环；
    K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
  13. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1或Ar 2相同或者不同，且分别独立地选自氢或以下基团组成的组：
    Figure PCTCN2021090725-appb-100038
    Figure PCTCN2021090725-appb-100039
  14. 根据权利要求1所述的含氮化合物，其特征在于，所述Het为碳原子数为3～25的含氮杂芳基。
  15. 根据权利要求1所述的含氮化合物，其特征在于，L选自单键、取代或未取代的碳原子数为6～20的亚芳基、取代或未取代的碳原子数为3～20的亚杂芳基；
    优选地，L中的取代基选自氘、卤素基团、氰基、碳原子数为1～5的烷基、碳原子数为6～12的芳基、碳原子数为3～10的环烷基。
  16. 根据权利要求1所述的含氮化合物，其特征在于，L选自单键或j-1至j-14所示基团所组成的组：
    Figure PCTCN2021090725-appb-100040
    其中，M 2选自单键或者
    Figure PCTCN2021090725-appb-100041
    Figure PCTCN2021090725-appb-100042
    表示化学键；
    Q 1～Q 5和Q’ 1～Q’ 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
    Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
    Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
    Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 32中至少一个选自N；当Q 24～Q 32中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
    E 1～E 14、J 5～J 8各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被一个或多个氘、氟、氯、氰基取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为8～12的芳基甲硅烷基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基、碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基，碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，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的磷氧基，碳原子数为18～24的三芳基硅基；
    e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
    K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
    K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
  17. 根据权利要求1所述的含氮化合物，其特征在于，L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、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚吡啶基。
  18. 根据权利要求1所述的含氮化合物，其特征在于，L选自单键或者如下基团所组成的组：
    Figure PCTCN2021090725-appb-100043
    Figure PCTCN2021090725-appb-100044
  19. 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以下化合物所组成的组：
    Figure PCTCN2021090725-appb-100045
    Figure PCTCN2021090725-appb-100046
    Figure PCTCN2021090725-appb-100047
    Figure PCTCN2021090725-appb-100048
    Figure PCTCN2021090725-appb-100049
    Figure PCTCN2021090725-appb-100050
    Figure PCTCN2021090725-appb-100051
    Figure PCTCN2021090725-appb-100052
    Figure PCTCN2021090725-appb-100053
    Figure PCTCN2021090725-appb-100054
    Figure PCTCN2021090725-appb-100055
    Figure PCTCN2021090725-appb-100056
    Figure PCTCN2021090725-appb-100057
    Figure PCTCN2021090725-appb-100058
    Figure PCTCN2021090725-appb-100059
    Figure PCTCN2021090725-appb-100060
    Figure PCTCN2021090725-appb-100061
    Figure PCTCN2021090725-appb-100062
    Figure PCTCN2021090725-appb-100063
    Figure PCTCN2021090725-appb-100064
    Figure PCTCN2021090725-appb-100065
    Figure PCTCN2021090725-appb-100066
    Figure PCTCN2021090725-appb-100067
    Figure PCTCN2021090725-appb-100068
  20. 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1～19任一项所述的含氮化合物；
    优选地，所述功能层包括电子传输层，所述电子传输层包括所述含氮化合物；
    优选地，所述功能层包括空穴阻挡层，所述空穴阻挡层包括所述含氮化合物。
  21. 根据权利要求20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；
    优选地，所述有机电致发光器件为蓝光器件或绿光器件。
  22. 一种电子装置，其特征在于，包括权利要求20或21所述的电子元件。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024014303A1 (ja) * 2022-07-13 2024-01-18 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102603291B1 (ko) * 2020-01-30 2023-11-15 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
CN111848501B (zh) 2020-05-08 2021-06-01 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN114478269B (zh) * 2020-11-13 2024-02-02 广州华睿光电材料有限公司 有机化合物、混合物、组合物及有机电子器件
CN112661706B (zh) * 2020-12-22 2023-01-20 陕西莱特光电材料股份有限公司 一种螺环化合物以及使用其的电子元件和电子装置
CN113620899B (zh) * 2021-08-20 2023-05-02 上海钥熠电子科技有限公司 芳香胺化合物及其在有机电致发光显示器件中的应用
CN115109001B (zh) * 2022-07-26 2024-07-30 京东方科技集团股份有限公司 含氮化合物及其有机电致发光器件

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110128279A (zh) * 2019-06-14 2019-08-16 陕西莱特光电材料股份有限公司 有机电致发光材料及包含该材料的有机电致发光器件
CN110615759A (zh) * 2019-09-25 2019-12-27 陕西莱特光电材料股份有限公司 化合物、光电转化器件及电子装置
WO2020045924A1 (ko) * 2018-08-29 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020046049A1 (ko) * 2018-08-31 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN111018797A (zh) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 有机化合物、包含该有机化合物的电子元件及电子装置
CN111039881A (zh) * 2019-09-25 2020-04-21 陕西莱特光电材料股份有限公司 有机化合物和电子装置
WO2020080872A1 (ko) * 2018-10-18 2020-04-23 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN111848501A (zh) * 2020-05-08 2020-10-30 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置
CN111925315A (zh) * 2020-04-07 2020-11-13 陕西莱特光电材料股份有限公司 含氮化合物、使用其的有机致电发光器件及电子装置

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4157245B2 (ja) * 2000-02-21 2008-10-01 株式会社トクヤマ クロメン化合物
CN107189436B (zh) * 2017-07-20 2019-12-27 中国科学院长春应用化学研究所 一种聚酰亚胺纳米泡沫及其制备方法
KR102230983B1 (ko) * 2018-04-10 2021-03-23 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR102163070B1 (ko) * 2018-08-31 2020-10-07 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102289383B1 (ko) * 2018-09-04 2021-08-12 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102227044B1 (ko) * 2018-10-17 2021-03-12 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN112209840B (zh) 2020-03-13 2022-01-28 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
CN111961038B (zh) 2020-07-20 2021-10-08 陕西莱特光电材料股份有限公司 化合物、有机致电发光器件及电子装置
CN112142548B (zh) 2020-09-30 2021-09-24 陕西莱特光电材料股份有限公司 一种有机化合物以及使用其的电子元件和电子装置

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020045924A1 (ko) * 2018-08-29 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020046049A1 (ko) * 2018-08-31 2020-03-05 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
WO2020080872A1 (ko) * 2018-10-18 2020-04-23 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN110128279A (zh) * 2019-06-14 2019-08-16 陕西莱特光电材料股份有限公司 有机电致发光材料及包含该材料的有机电致发光器件
CN110615759A (zh) * 2019-09-25 2019-12-27 陕西莱特光电材料股份有限公司 化合物、光电转化器件及电子装置
CN111039881A (zh) * 2019-09-25 2020-04-21 陕西莱特光电材料股份有限公司 有机化合物和电子装置
CN111018797A (zh) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 有机化合物、包含该有机化合物的电子元件及电子装置
CN111925315A (zh) * 2020-04-07 2020-11-13 陕西莱特光电材料股份有限公司 含氮化合物、使用其的有机致电发光器件及电子装置
CN111848501A (zh) * 2020-05-08 2020-10-30 陕西莱特光电材料股份有限公司 一种含氮化合物以及使用其的电子元件和电子装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024014303A1 (ja) * 2022-07-13 2024-01-18 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器

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