WO2021135207A1 - 含氮化合物、电子元件和电子装置 - Google Patents

含氮化合物、电子元件和电子装置 Download PDF

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WO2021135207A1
WO2021135207A1 PCT/CN2020/105862 CN2020105862W WO2021135207A1 WO 2021135207 A1 WO2021135207 A1 WO 2021135207A1 CN 2020105862 W CN2020105862 W CN 2020105862W WO 2021135207 A1 WO2021135207 A1 WO 2021135207A1
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carbon atoms
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groups
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unsubstituted
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French (fr)
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聂齐齐
曹佳梅
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陕西莱特光电材料股份有限公司
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Priority to JP2022527951A priority Critical patent/JP7286210B2/ja
Priority to KR1020217043404A priority patent/KR20220121174A/ko
Publication of WO2021135207A1 publication Critical patent/WO2021135207A1/zh

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Definitions

  • This application relates to the technical field of organic materials, in particular to a nitrogen-containing compound, an electronic component using the nitrogen-containing compound, and an electronic device using the electronic component.
  • Such electronic components usually include a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • the electronic element when it is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence.
  • anode When voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the electroluminescent layer, the holes on the anode side also move to the light emitting layer, and the electrons and holes are combined in the electroluminescent layer. Excitons are formed, and the excitons are in an excited state to release energy to the outside, so that the electroluminescent layer emits light to the outside.
  • an electron blocking layer may also be provided between the energy conversion layer and the hole transport layer.
  • the hole transport performance of the film layer located between the anode and the energy conversion layer has an important influence on the performance of the electronic components.
  • compounds containing fluorene groups can be used in the hole transport layer.
  • the performance of existing hole transport layer materials containing fluorene groups needs to be further improved.
  • the purpose of this application is to provide a nitrogen-containing compound, an electronic component and an electronic device to improve the performance of the electronic component and the electronic device.
  • a nitrogen-containing compound is provided, and the structure of the nitrogen-containing compound is shown in Chemical Formula 1:
  • R 1 and R 2 are independently selected from hydrogen and the group shown in Chemical Formula 1-1, and R 1 and R 2 have and only one of the group shown in Chemical Formula 1-1, when R 1 or R 2 is selected In the case of hydrogen, the R 1 or R 2 selected from hydrogen can be substituted by R 4;
  • R 3 and R 4 are each independently selected from deuterium, halogen, cyano, heteroaryl with 3 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, and trioxane with 3 to 12 carbon atoms Cyclosilyl group, arylsilyl group having 8 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, and alkenyl group having 2 to 6 carbon atoms , C 2-6 alkynyl, C 3-20 cycloalkyl, C 2-10 heterocycloalkyl, C 5-10 cycloalkenyl, carbon Heterocyclenyl group with 4 to 10 atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, aryloxy group with 6 to 18 carbon atoms, carbon atom An arylthio group having 6 to 18, a phosphoroxy group having 6 to 18 carbon atom
  • a is selected from 0, 1, 2, 3 or 4. When a is greater than or equal to 2, any two R 3 are the same or different;
  • b is selected from 0, 1, 2 or 3, when b is greater than or equal to 2, any two R 4 are the same or different;
  • 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;
  • Ar 1 and Ar 2 are independently selected from the following substituted or unsubstituted groups: alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 carbon atoms, and those having 6-30 carbon atoms An aryl group and a heteroaryl group having 3-30 carbon atoms, and neither of the Ar 1 and Ar 2 are 9,9-diphenylfluorenyl groups.
  • an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer provided between the anode and the cathode; the functional layer includes the above-mentioned nitrogen-containing compound.
  • the electronic component is an organic electroluminescence device.
  • the electronic component is a solar cell.
  • an electronic device including the above-mentioned electronic component.
  • the nitrogen-containing compound of the present application introduces an adamantane structure at the lateral position of the fluorene to increase the electron density of the fluorene ring and the entire conjugated system of the nitrogen-containing compound through the hyperconjugation effect, which can enhance the hole conductivity and electron resistance of the nitrogen-containing compound. At the same time, it can improve the luminous efficiency and lifespan of the electroluminescent device using the nitrogen-containing compound, and increase the conversion efficiency and lifespan of the photoelectric conversion device using the nitrogen-containing compound.
  • the adamantyl group is introduced between the branches of the triarylamine, which is a nearly planar structure, but not at the end.
  • the large volume steric hindrance of the adamantyl group can finely adjust the bonding angle and the degree of conjugation between the amine and each aryl group, thereby obtaining It is more suitable for the material HOMO value of the adjacent layer, reduces the operating voltage of the organic electroluminescence device, and increases the open circuit voltage of the photoelectric conversion device.
  • the introduced adamantyl group can also increase the molecular weight of nitrogen-containing compounds and reduce molecular symmetry, can increase the glass transition temperature and vapor deposition temperature of the compounds of this application, and control the crystallinity of nitrogen-containing compounds so that nitrogen compounds can be used for It has better physical and thermal stability during mass production, thereby facilitating the mass production stability of electronic components, such as organic electroluminescence devices and photoelectric conversion devices.
  • 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 photoelectric conversion device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a first electronic 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.
  • Electron transport layer 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • R 1 or R 2 when R 1 or R 2 is selected from hydrogen, said R 1 or R 2 selected from hydrogen can be substituted by R 4. It is when R 1 and R 2, when one has one selected from hydrogen, wherein R 4 is selected from hydrogen, can be substituted or may not be substituted with R 4.
  • R 1 and R 2 when one has one selected from hydrogen, wherein R 4 is selected from hydrogen, can be substituted or may not be substituted with R 4.
  • R 2 when R 2 is selected from chemical formula 1-1 and R 1 is selected from hydrogen, R 1 may be substituted by R 4 or not by R 4 , and the specific chemical formula 1 may include:
  • any two R 4 are the same or different.
  • adamantane is a three-dimensional structure, in the compound structure diagram, because of the different drawing angles, it will present different planar shapes.
  • the ring structure formed on 9,9-dimethylfluorene is all adamantane.
  • the connection position is also the same. E.g: All have the same structure.
  • the present application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Chemical Formula 1:
  • R 1 and R 2 are independently selected from hydrogen and the group shown in Chemical Formula 1-1, and R 1 and R 2 have and only one of the group shown in Chemical Formula 1-1, when R 1 or R 2 is selected In the case of hydrogen, the R 1 or R 2 selected from hydrogen can be substituted by R 4;
  • R 3 and R 4 are each independently selected from deuterium, halogen, cyano, heteroaryl with 3 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, and trioxane with 3 to 12 carbon atoms Cyclosilyl group, arylsilyl group having 8 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, and alkenyl group having 2 to 6 carbon atoms , C 2-6 alkynyl, C 3-20 cycloalkyl, C 2-10 heterocycloalkyl, C 5-10 cycloalkenyl, carbon Heterocyclenyl group with 4 to 10 atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, aryloxy group with 6 to 18 carbon atoms, carbon atom An arylthio group having 6 to 18, a phosphoroxy group having 6 to 18 carbon atom
  • a is selected from 0, 1, 2, 3 or 4, when a is greater than or equal to 2, any two R 3 are the same or different;
  • b is selected from 0, 1, 2 or 3, when b is greater than or equal to 2, any two R 4 is the same or different;
  • 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;
  • Ar 1 and Ar 2 are independently selected from the following substituted or unsubstituted groups: alkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 carbon atoms, and those having 6-30 carbon atoms An aryl group and a heteroaryl group having 3-30 carbon atoms, and neither of the Ar 1 and Ar 2 are 9,9-diphenylfluorenyl groups.
  • neither of the Ar 1 and Ar 2 is a spirobifluorenyl group.
  • the substituents of L, Ar 1 and Ar 2 are independently selected from deuterium, halogen, cyano, heteroaryl with 3 to 18 carbon atoms, and aryl with 6 to 18 carbon atoms.
  • Alkyl groups halogenated alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, carbon atoms Heterocycloalkyl having 2 to 10, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, and carbon atoms
  • the substituent of Ar 1 and/or Ar 2 may also be a triphenylsilyl group.
  • the number of carbon atoms of L, Ar 1 and Ar 2 refers to the number of all carbon atoms.
  • L is selected from a substituted arylene group having 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12.
  • 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 it has no substituents or is substituted by one or more substituents.
  • the substituents include, but are not limited to, deuterium (D), halogen (e.g. F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, Arylthio, cycloalkyl, heterocycloalkyl, etc.
  • hetero means that a functional group includes at least one heteroatom such as B, N, O, S, or P, and the remaining atoms are carbon and hydrogen.
  • the unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.
  • alkyl may include linear or branched alkyl.
  • the alkyl group may have 1 to 20 carbon atoms, and in this application, a numerical range such as “1 to 20” refers to each integer in the given range.
  • “1 to 20 carbon atoms” means that it can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms , 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms , 18 carbon atoms, 19 carbon atoms or 20 carbon atoms alkyl group.
  • the alkyl group may also be an alkyl group having 1 to 10 carbon atoms.
  • the alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms.
  • the alkyl group may be substituted or unsubstituted.
  • the alkyl group is selected from alkyl groups having 1-10 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, Tert-butyl, pentyl and hexyl.
  • alkenyl refers to a hydrocarbon group containing one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups can be unsubstituted or substituted. Alkenyl groups may have 1 to 20 carbon atoms, and whenever appearing herein, a numerical range such as “1 to 20" refers to each integer in the given range.
  • “1 to 20 carbon atoms” means that it can contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms , 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms , 18 carbon atoms, 19 carbon atoms or 20 carbon atoms alkenyl.
  • the alkenyl group may be vinyl, butadiene, or 1,3,5-hexatriene.
  • cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and condensed ring structures.
  • Cycloalkyl groups may have 3-20 carbon atoms, and numerical ranges such as "3 to 20" refer to individual integers in the given range.
  • “3 to 20 carbon atoms” means that it can contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms , 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms Or a cycloalkyl group of 20 carbon atoms.
  • the cycloalkyl group may be a small ring, an ordinary ring, or a large ring having 3 to 20 carbon atoms.
  • Cycloalkyl groups can also be classified as monocyclic-only one ring, bicyclic-two rings, polycyclic-three or more rings. Cycloalkyl groups can also be divided into two rings sharing one carbon atom-a spiro ring, two rings sharing two carbon atoms-a fused ring, and two rings sharing two or more carbon atoms-a bridged ring. In addition, cycloalkyl groups may be substituted or unsubstituted.
  • the cycloalkyl group is selected from cycloalkyl groups having 3-10 carbon atoms, and specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, and A monocyclic aryl group and a condensed ring aryl group conjugated by carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application.
  • the aryl group does not contain heteroatoms such as B, N, O, S, or P.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10 ]Phenanthryl, pyrenyl, benzofluoranthene, Base, fluorenyl, etc., but not limited to this.
  • the "aryl group” in this application can contain 6-30 carbon atoms.
  • the number of carbon atoms in the aryl group can be 6-25. In other embodiments, the number of carbon atoms in the aryl group can be It is 6-18. In other embodiments, the number of carbon atoms in the aryl group may be 6-13. For example, the number of carbon atoms in an aryl group can be 6, 12, 13, 18, 20, 25, or 30. Of course, the number of carbon atoms can also be other numbers, which will not be one by one here. Enumerate.
  • the number of ring-forming carbon atoms refers to the number of carbon atoms located on the aromatic ring in a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group. It should be noted that as a substituent The number of ring-forming carbon atoms of the aryl and heteroaryl groups are also taken into account, and the number of carbon atoms of other substituents on the aromatic ring is not counted.
  • the number of ring-forming carbon atoms of the fluorenyl group is 13
  • the number of ring-forming carbon atoms of 9,9-dimethylfluorenyl is 13
  • the number of ring-forming carbon atoms of the diphenylfluorenyl group is 25.
  • the number of ring-forming carbon atoms of the aryl group having 6-20 ring-forming carbon atoms may be, for example, 6-20, 6-18, 6-14, or 6-10, but it is not limited thereto.
  • a substituted aryl group means that one or more hydrogen atoms in the aryl group are replaced by other groups.
  • at least one hydrogen atom is replaced by a deuterium atom, F, Cl, I, CN, hydroxyl, amino, branched alkyl, linear alkyl, cycloalkyl, alkoxy, alkylamino or other groups.
  • the substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18.
  • the number of carbon atoms of 9,9-dimethylfluorenyl is 15, and the number of carbon atoms of 9,9-diphenylfluorenyl and spirobifluorenyl are both 25.
  • the biphenyl group can be interpreted as an aryl group or a substituted phenyl group.
  • the fluorenyl group may be substituted, and the substituted fluorenyl group may be: Can also be Wait.
  • the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si, and S as a heteroatom.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazole Group, benzothiazolyl, benzo, be
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system
  • N-arylcarbazolyl, N-heteroarylcarbazolyl, phenyl-substituted dibenzofuranyl, Dibenzofuranyl-substituted phenyl groups and the like are heteroaryl groups of multiple aromatic ring systems conjugated through carbon-carbon bonds.
  • the number of ring-forming carbon atoms refers to the total number of carbon atoms located on the aromatic ring.
  • a heteroaryl group with 3-20 ring-forming carbon atoms refers to the heteroaryl group located on the heteroaromatic ring
  • the number of carbon atoms in is 3-20, and the number of carbon atoms in the substituents on the heteroaryl group is not counted.
  • the number of ring-forming carbon atoms in the heteroaryl group can be 3-20, 3-18, 4-18, 3-12, 3-8, but is not limited thereto.
  • a substituted heteroaryl group refers to one or more hydrogen atoms in the heteroaryl group being replaced by its group, for example, at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, CN, amino group , Alkyl, haloalkyl, cycloalkyl, aryloxy, arylthio, silyl, alkylamino, arylamino, boryl, phosphine or other group substitutions.
  • the explanation of the aryl group can be applied to the arylene group, and the explanation of the heteroaryl group also applies to the heteroarylene group.
  • halogen can be fluorine, chlorine, bromine, or iodine.
  • the nitrogen-containing compound of the present application can be used to prepare organic electroluminescent devices and photoelectric conversion devices, and is especially suitable for preparing electron blocking layers (also known as hole auxiliary layers and second hole) of organic electroluminescent devices and photoelectric conversion devices. Transmission layer, etc.) to improve the efficiency and life of organic electroluminescent devices and photoelectric conversion devices, reduce the operating voltage of organic electroluminescent devices, increase the open circuit voltage of photoelectric conversion devices, and improve the performance of photoelectric conversion devices and organic electroluminescent devices. Mass production stability.
  • Ar 1 and Ar 2 are each independently selected from the following substituted or unsubstituted groups: aryl groups having 6-20 carbon atoms and heteroaryl groups having 3-20 carbon atoms.
  • L is selected from a single bond, a substituted or unsubstituted arylene group having 6-20 ring carbon atoms, and a substituted or unsubstituted heteroarylene group having 3-20 ring carbon atoms.
  • L is selected from a single bond or the group consisting of:
  • Z 1 to Z 22 are each independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, and alkane having 1 to 6 carbon atoms
  • An oxy group, an aryloxy group with 6-18 carbon atoms, an arylthio group with 6-18 carbon atoms, an aryl group with 6-20 carbon atoms, and a halogenated aryl group with 6-20 carbon atoms Heteroaryl groups with 3-20 carbon atoms, silyl groups with 3-12 carbon atoms, and cycloalkyl groups with 3-10 carbon atoms;
  • X is selected from substituted or unsubstituted alkylene groups with 1-10 carbon atoms, substituted or unsubstituted cycloalkylene groups with 3-10 carbon atoms, and substituted or unsubstituted carbon atoms with 6-20
  • X 1 to X 10 each independently represent C or N, and at least one is N
  • X 11 to X 15 each independently Represents C or N, and at least one is N
  • X 16 to X 23 each independently represent C or N, and at least one is N
  • X 24 , X 25 are selected from each independently selected from single bond, C(R 5 R 6 ), N(R 7 ), O, S, Si(R 5 R 6 ), Se; preferably, X 24 and X 25 cannot be single bonds at the same time;
  • R 5 to R 7 are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups with 1-10 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, substituted or unsubstituted A heteroaryl group with 3-20 carbon atoms;
  • X 26 and X 27 each independently represent C or N, and at least one of them is N;
  • n 1 , n 3 , n 4 , n 6 , n 7 , n 8 , n 9 , n 16 , n 18 , and n 21 are independently selected from 1, 2, 3 or 4; n 10 , n 11 , n 22 Each independently selected from 1, 2 or 3; n 13 , n 20 are selected from 1, 2 , 3, 4 or 5; n 2, n 14 , n 19 are each independently selected from 1, 2, 3, 4, 5 Or 6; n 15 is selected from 1, 2, 3, 4, 5 , 6 or 7; n 5, n 12 , and n 17 are independently selected from 1, 2, 3, 4, 5, 6, 7 or 8.
  • X is an alkylene group having 1-4 carbon atoms, a cycloalkylene group having 5-10 carbon atoms, an arylene group having 6-12 carbon atoms, and 3-12 carbon atoms.
  • the heteroarylene include, but are not limited to: methylene, phenylene and the like.
  • R 5 to R 7 are independently selected from hydrogen, deuterium, alkyl groups having 1-4 carbon atoms, aryl groups having 6-12 carbon atoms, and heteroaryl groups having 3-12 carbon atoms. base.
  • R 5 to R 7 include, but are not limited to: methyl, tert-butyl, phenyl and the like.
  • Z 1 is an aryl group having 6-20 carbon atoms substituted by deuterium, for example, a phenyl group substituted by deuterium.
  • L is selected from a single bond or the group consisting of:
  • L is selected from the group consisting of a single bond or the following groups:
  • Ar 1 and Ar 2 are each independently selected from the following substituted or unsubstituted groups: aryl groups having 6-20 carbon atoms and heteroaryl groups having 3-20 carbon atoms.
  • Ar 1 and Ar 2 are independently selected from the following substituted or unsubstituted groups: aryl groups having 6-20 ring carbon atoms, and heteroaryl groups having 5-20 ring carbon atoms.
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • T 1 to T 20 are independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 6 carbon atoms, and alkane having 1 to 6 carbon atoms.
  • An oxy group, an aryloxy group with 6-18 carbon atoms, an arylthio group with 6-18 carbon atoms, an aryl group with 6-20 carbon atoms, and a halogenated aryl group with 6-20 carbon atoms Heteroaryl groups with 3-20 carbon atoms, silyl groups with 3-12 carbon atoms, and cycloalkyl groups with 3-10 carbon atoms;
  • W is selected from substituted or unsubstituted alkylene groups with 1-10 carbon atoms, substituted or unsubstituted cycloalkylene groups with 3-10 carbon atoms, and substituted or unsubstituted carbon atoms with 6-20
  • W 1 and W 2 each independently represent C or N, and at least one of them is N
  • W 3 to W 7 are each independently Represents C or N, and at least one is N
  • W 8 to W 15 each independently represents C or N, and at least one is N
  • W 16 and W 17 are each independently selected from a single bond, C(R 9 R 10 ) , N(R 8 ), O, S, Si(R 9 R 10 ), Se; preferably, W 16 and W 17 cannot be single bonds at the same time.
  • R 9 to R 10 are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 7 to 18 carbon atoms, A substituted or unsubstituted heteroaryl group with 3-18 carbon atoms;
  • R 8 is selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups with 1-6 carbon atoms, substituted or unsubstituted aryl groups with 6-20 carbon atoms, and substituted or unsubstituted carbon atoms with 3 -20 heteroaryl;
  • W is an alkylene group having 1-4 carbon atoms, a cycloalkylene group having 5-10 carbon atoms, an arylene group having 6-12 carbon atoms, and 3-12 carbon atoms.
  • the heteroarylene include, but are not limited to: methylene, phenylene and the like.
  • R 9 to R 10 are each independently selected from hydrogen, deuterium, and an alkyl group having 1 to 4 carbon atoms.
  • R 9 to R 10 include, but are not limited to: methyl, tert-butyl and the like.
  • R 8 is each independently selected from hydrogen, deuterium, alkyl groups having 1-6 carbon atoms, aryl groups having 6-12 carbon atoms, and heteroaryl groups having 3-12 carbon atoms.
  • Specific examples of R 8 include but are not limited to: methyl, phenyl and the like.
  • T 1 is an aryl group having 6-20 carbon atoms substituted by deuterium, for example, a phenyl group substituted by deuterium.
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
  • R 3 and R 4 are each independently selected from deuterium, fluorine, cyano, aryl with 6-18 carbon atoms, heteroaryl with 5-18 carbon atoms, and A 1-6 alkyl group and a 3-10 cycloalkyl group.
  • R 3 and R 4 include, but are not limited to, deuterium, fluorine, cyano, methyl, tert-butyl, phenyl, cyclopentyl, cyclohexyl, pyridyl and the like.
  • R 3 and/or R 4 are phenyl substituted with deuterium.
  • the nitrogen-containing compound is selected from the group formed by the following compounds:
  • the present application also provides an electronic component, which includes an anode and a cathode arranged oppositely, and a functional layer provided between the anode and the cathode; the functional layer includes the nitrogen-containing compound of the present application.
  • the electronic component can be used to realize photoelectric conversion or electro-optical conversion.
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device includes an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes the nitrogen-containing compound provided in the present application.
  • the functional layer 300 includes an electron blocking layer 322, and the electron blocking layer 322 includes the nitrogen-containing compound provided in the present application.
  • the electron blocking layer 322 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided in the present application and other materials.
  • the functional layer 300 includes a hole transport layer 321 and/or a hole injection layer 310, and the hole transport layer 321 may contain the nitrogen-containing compound provided in the present application to improve the hole transport ability in the electronic device.
  • the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, and an electron transport layer which are sequentially stacked. Layer 350 and cathode 200.
  • the nitrogen-containing compound provided in the present application can be applied to the electron blocking layer 322, which can effectively improve the luminous efficiency and lifetime of the organic electroluminescent device, and reduce the driving voltage of the organic electroluminescent device.
  • 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 SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto.
  • a transparent electrode containing indium tin oxide (ITO) as an anode is included.
  • the hole transport layer 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. This does not make special restrictions.
  • the hole transport layer 321 is composed of the compound NPB.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, and may also include a host material and a guest material.
  • the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to The host material, the host material transfers energy to the guest material, so that the guest material can emit light.
  • the host material of the organic light-emitting layer 330 can be a metal chelating 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 CBP.
  • the guest 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 any special considerations for this. limit.
  • the guest material of the organic light-emitting layer 330 may be Ir(ppy) 3 .
  • the electron transport layer 350 may be a single layer structure or a multilayer structure, which may include one or more electron transport materials, which may be selected from benzimidazole derivatives, oxadiazole derivatives, and quinoxalines. Derivatives or other electronic transmission materials, this application does not impose special restrictions on this.
  • the electron transport layer 340 may be composed of ET-1 and LiQ.
  • the cathode 200 includes the following cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al, and BaF 2 /Ca, but not limited thereto. It is preferable to include a metal electrode containing aluminum as a cathode.
  • a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 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 m-MTDATA.
  • an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 350.
  • the electron injection layer 360 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 360 may include LiQ.
  • a hole blocking layer 340 may also be provided between the organic light emitting layer 330 and the electron transport layer 350.
  • the electronic component may be a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the nitrogen-containing compound provided in the present application.
  • the functional layer 300 includes an electron blocking layer 322, and the electron blocking layer 322 includes the nitrogen-containing compound provided in the present application.
  • the electron blocking layer 322 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound and other materials.
  • the photoelectric conversion device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370 as an energy conversion layer, an electron transport layer 350, and a cathode 200 that are sequentially stacked.
  • the nitrogen-containing compound provided in the present application can be applied to the electron blocking layer 322 of a photoelectric conversion device, which can effectively improve the luminous efficiency and lifetime of the photoelectric conversion device, and increase the open circuit voltage of the photoelectric conversion device.
  • a hole injection layer 310 may also be provided between the anode 100 and the hole transport layer 321.
  • an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350.
  • a hole blocking layer 340 may also be provided between the photoelectric conversion layer 370 and the electron transport layer 350.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • the solar cell includes an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370, an electron transport layer 350, and a cathode 200 stacked in sequence, wherein the electron blocking layer 322 contains The nitrogen-containing compound of the present application.
  • the present application also provides an electronic device, which includes the above-mentioned electronic component. Since the electronic device includes the above-mentioned electronic components, it has the same beneficial effects, which will not be repeated here in this application.
  • the electronic device is a first electronic device 400, and the electronic device includes the above-mentioned organic electroluminescent device.
  • the first electronic device 400 may be 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, which includes any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments.
  • the second electronic device 500 may be 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 magnesium bar (13.54g, 564mmol) and ether (100mL) were placed in a round-bottomed flask dried under the protection of nitrogen, and iodine (100mg) was added. Then the ether (200mL) solution containing intermediate IA-1 (50.00g, 187.0mmol) 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 reduced to 0°C, A diethyl ether (200mL) solution containing adamantanone (22.45g, 149mmol) was slowly dropped into it.
  • Table 1 Compound structure, preparation and characterization data
  • the nuclear magnetic data of compound 3 is, 1 H NMR (CD 2 Cl 2 , 400MHz): 8.10 (d, 1H), 8.00 (d, 1H), 7.67-7.59 (m, 6H), 7.54 (d, 2H) ,7.45-7.42(m,3H),7.36-7.25(m,8H),7.12(br,1H),7.06(br,1H),2.92(t,4H), 2.19(d,2H),2.00(s , 2H), 1.82 (d, 4H), 1.61 (s, 2H), 1.44 (s, 6H).
  • the nuclear magnetic data of compound 7 are, 1 H NMR (CD 2 Cl 2 , 400MHz): 8.11(d,1H), 8.03(d,1H), 7.91(d,1H), 7.85(d,1H), 7.62-7.60 (m,4H),7.56(d,2H),7.51(d,1H),7.45-7.39(m,3H),7.36-7.26(m,7H),7.21(d,1H),7.07(d,1H) ), 2.92 (t, 4H), 2.19 (d, 2H), 2.00 (s, 2H), 1.82 (d, 4H), 1.62 (s, 2H).
  • the NMR data of compound 54 are, 1 H NMR (400MHz, CD 2 Cl 2 ): 8.11 (d, 1H), 7.99 (d, 1H), 7.66 (d, 2H), 7.63-7.62 (m, 3H), 7.58 (d,1H),7.41(d,2H),7.35(s,2H),7.32(t,2H),7.28-7.24(m,4H),7.12(d,2H),7.07(d,1H), 2.92 (t, 4H), 2.19 (d, 2H), 2.00 (s, 2H), 1.82 (d, 4H), 1.62 (s, 2H), 1.42 (s, 12H).
  • Table 4 Compound number, structure, preparation and characterization data
  • the intermediate I-A-6 was prepared according to the synthesis method of the intermediate I-B, except that the intermediate I-A was replaced by the intermediate I-A-5, and the p-chlorophenylboronic acid was replaced by phenylboronic acid to obtain the intermediate I-A-6.
  • Table 5 Compound number, structure, preparation and characterization data
  • intermediate I-G-2 is used instead of intermediate I-A-2 to synthesize intermediate I-G.
  • the difference is that the intermediate IG is used instead of IA, the raw material 6 in the second column of the table below is used instead of 4-aminobiphenyl, and the raw material 7 in the third column is used instead of 4-bromobiphenyl, and the raw material is 6
  • the intermediates in the fourth column were synthesized with raw material 7 instead of intermediate II-A to prepare the compounds shown in the fifth column in Table 6.
  • the specific compound number, structure, synthesis yield of the last step, and characterization data are shown in Table 6.
  • intermediate I-G is used instead of intermediate I-A to synthesize intermediate I-G-1.
  • Table 7 Compound number, structure, preparation and characterization data
  • the ITO thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm (length) ⁇ 40mm (width) ⁇ 0.7mm (thickness).
  • the photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns.
  • Ozone and O 2 :N 2 plasma are used for surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • M-MTDATA was vacuum-evaporated on the experimental substrate (anode) to form a thickness of Hole injection layer (HIL), and vacuum evaporation of NPB on the hole injection layer to form a thickness of The first hole transport layer.
  • HIL Hole injection layer
  • Compound 1 was evaporated on the first hole transport layer to form a thickness of The second hole transport layer.
  • Ir(ppy) 3 is simultaneously doped according to the film thickness ratio of 100:5 to form a thickness of The light-emitting layer (EML).
  • EML The light-emitting layer
  • ET-1 and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation Thick electron transport layer (ETL), LiQ is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL) is then mixed with magnesium (Mg) and silver (Ag) at an evaporation rate of 1:9, and then vacuum-evaporated on the electron injection layer to form a thickness of The cathode.
  • ETL Thick electron transport layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-1, thus completing the manufacture of organic light-emitting devices.
  • each material used is as follows:
  • the second hole transport layer is prepared to prepare a corresponding green organic electroluminescent device.
  • the green organic electroluminescent devices prepared in Examples 1-43 and Comparative Examples 1-7 were tested for performance. Specifically , the IVL performance of the devices was tested under the condition of 10 mA/cm 2. The lifetime of the T95 device was under the initial brightness of 17,000 nits. The test was performed, and the test results are shown in Table 8.
  • the luminous efficiency (Cd/A) and lifetime of the organic electroluminescent devices prepared in Examples 1 to 43 are compared with Comparative Examples 1 to 7 when the color coordinates are not much different. Ratios 1 to 7 are equivalent, but the device voltages of Comparative Examples 1 to 7 are overall high. As shown in the above table, compared with Comparative Examples 1 to 7, the device voltages of Examples 1 to 43 are reduced by at least 0.45V. Therefore, the use of the nitrogen-containing compound of the present application in the second hole transport layer can prepare an organic electroluminescent device with a lower working voltage.
  • the nitrogen-containing compound of the present application introduces an adamantyl structure on the side of the fluorene, which increases the electron density of the fluorene ring and the conjugated system of the entire compound through the hyperconjugation effect, which can enhance the hole conductivity and electron tolerance of the nitrogen-containing compound
  • the introduced adamantyl group can also increase the molecular weight of nitrogen-containing compounds and reduce molecular symmetry, increase the glass transition temperature and vapor deposition temperature of the compound of the application, and control the crystallinity of nitrogen-containing compounds so that the nitrogen compounds When used in mass production, it has better physical and thermal stability, which facilitates the mass production stability of organic electroluminescent devices and photoelectric conversion devices.
  • the organic electroluminescent devices prepared in Example 1 were divided into two groups. One group of devices was directly subjected to performance testing without heat treatment. The test results are shown in Table 9. The other group was heat-treated (placed at 110°C for 1 hour) and then tested for performance. See Table 10 for the performance test results. With reference to the above method, the organic electroluminescent devices prepared in Example 1, Example 14, Example 21, Example 32, Example 35, Example 38, Example 41, and Comparative Examples 1 to 7 were obtained without heat treatment. The performance parameters and performance parameters after heat treatment.
  • the organic electroluminescent devices of Comparative Examples 1, Comparative Examples 2, and Comparative Examples 4 to 7 reduced the luminous efficiency and external quantum by about 23% or more after the heat treatment.
  • the efficiency and life are reduced by more than 10% after heat treatment.
  • the efficiency and lifespan of the organic electroluminescent device after the heat treatment in Comparative Example 3 were reduced by 5.8% and the lifespan by 6.5% compared with that before the heat treatment; while in Example 1, Example 14, Example 21, Example 35, implementation After the heat treatment, the organic electroluminescent devices of Example 38 and Example 41 still maintained the same efficiency and lifetime as before the heat treatment.
  • the compound of the present invention has a lower voltage compared with Comparative Example 1 and Comparative Example 3.
  • the reason may be that the compound of the present invention is higher than adamantane fluorene in No. 1, 3 adamantane fluorene.
  • Position 2 has a deeper HOMO, which makes the injection of holes into the light-emitting layer smoother.
  • Comparative Example 5 Comparative Example 6 and Comparative Example 7, the compound of the present invention has lower voltage and improved thermal stability.
  • the reason may be that the cycloalkyl group formed on the 9,9-dimethylfluorene of the present invention It is a rigid and bulky adamantyl group. Compared with a single ring structure, it has a stronger ability to reduce molecular stacking and can make the material reach a more stable film state.

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Abstract

一种结构如化学式1所示的含氮化合物、电子元件和电子装置被公开，该含氮化合物能够改善电子元件的性能，属于有机材料技术领域。其中，化学式1-1表示化学键； R1和R2分别独立地选自氢、化学式1-1所示的基团，且R1和R2有且只有一个为化学式1-1所示的基团，当R1或R2选自氢时，选自氢的所述R1或R2能被R4取代。

Description

含氮化合物、电子元件和电子装置 技术领域
本申请涉及有机材料技术领域，尤其涉及一种含氮化合物、应用该含氮化合物的电子元件和应用该电子元件的电子装置。
背景技术
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。该类电子元器件通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括能量转化层、位于能量转化层与阳极之间的空穴传输层、位于能量转化层与阴极之间的电子传输层。
举例而言，当电子元件为有机电致发光器件时，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。为了提高实现电致发光或者光电转化的电子元器件的性能，在能量转化层和空穴传输层之间还可以设置有电子阻挡层。
在实现电致发光或者光电转化的电子元器件中，位于阳极和能量转化层之间的膜层的空穴传输性能，对电子元器件的性能具有重要的影响。如中国专利申请CN201710407382.3等专利文献中的记载，含有芴基团的化合物可以用于空穴传输层。然而，现有的含有芴基团的空穴传输层材料，其性能有待进一步地提高。
所述背景技术部分公开的上述信息仅用于加强对本申请的背景的理解，因此它可以包括不构成对本领域普通技术人员已知的现有技术的信息。
发明内容
本申请的目的在于提供一种含氮化合物、电子元件和电子装置，以改善电子元件和电子装置的性能。
为实现上述发明目的，本申请采用如下技术方案：
根据本申请的第一个方面，提供一种含氮化合物，所述含氮化合物的结构如化学式1所示：
Figure PCTCN2020105862-appb-000001
其中，
Figure PCTCN2020105862-appb-000002
表示化学键；
R 1和R 2分别独立地选自氢、化学式1-1所示的基团，且R 1和R 2有且只有一个为化学式1-1所示的基团，当R 1或R 2选自氢时，选自氢的所述R 1或R 2能被R 4取代；
R 3、R 4分别独立地选自氘、卤素、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳 基、碳原子数为3～12的三烷基硅基、碳原子数为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3～20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；
a选自0，1，2，3或4，当a大于等于2时，任意两个R 3相同或不同；
b选自0，1，2或3，当b大于等于2时，任意两个R 4相同或不同；
L选自：单键、取代或未取代的碳原子数为6-30的亚芳基、取代或未取代的碳原子数为3-30的亚杂芳基；
Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基，且所述Ar 1和Ar 2均不为9，9-二苯基芴基。
根据本申请的第二个方面，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；所述功能层包含上述的含氮化合物。按照本申请的一种实施方式，所述电子元件为有机电致发光器件。按照本申请的另一种实施方式，所述电子元件为太阳能电池。
根据本申请的第三个方面，提供一种电子装置，包括上述的电子元件。
本申请的含氮化合物在芴的侧位引入金刚烷结构，通过超共轭效应提升芴环以及整个含氮化合物的共轭体系的电子密度，可以增强含氮化合物的空穴传导率以及电子耐受度，同时可以提高有应用该含氮化合物的机电致发光器件的发光效率以及寿命、提高应用该含氮化合物的光电转化器件的转换效率和寿命。金刚烷基引入至原本为近平面结构的三芳基胺的分支之间而非末端处，金刚烷基的大体积空间位阻可以精细调节胺与各个芳基成键键角及共轭程度，从而得到更适合于相邻层的材料HOMO值，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。不仅如此，引入的金刚烷基还可以增加含氮化合物的分子量并降低分子对称性，可以提高本申请化合物的玻璃化转变温度以及蒸镀温度，控制含氮化合物的结晶性，使得氮化合物用于量产时有更佳的物理和热学稳定性，进而便于电子元件，如有机电致发光器件和光电转化器件的量产稳定性。
附图说明
通过参照附图详细描述其示例实施方式，本申请的上述和其它特征及优点将变得更加明显。
图1是本申请实施方式的有机电致发光器件的结构示意图。
图2是本申请实施方式的光电转化器件的结构示意图。
图3是本申请一实施方式的第一电子装置的结构示意图。
图4是本申请一实施方式的第二电子装置的结构示意图。
图中主要元件附图标记说明如下：
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；330、有机电致发光层；340、空穴阻挡层；350、电子传输层；360、电子注入层；370、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
现在将参考附图更全面地描述示例实施例。然而，示例实施例能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施例使得本申请将更加全面和完整，并将示例实施例的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。
在图中，为了清晰，可能夸大了区域和层的厚度。在图中相同的附图标记表示相同或类似的结构，因而将省略它们的详细描述。
所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多实施例中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。然而，本领域技术人员将意识到，可以实践本申请的技术方案而没有所述特定细节中的一个或更多，或者可以采用其它的方法、组元、材料等。在其它情况下，不详细示出或描述公知结构、材料或者操作以避免模糊本申请的主要技术创意。
在本申请中，当R 1或R 2选自氢时，选自氢的所述R 1或R 2能被R 4取代。是指当R 1和R 2中有一者选自氢时，其中选自氢的一者能被R 4取代，也可以不被R 4取代。举例而言，当R 2选自化学式1-1，R 1选自氢时，R 1可被R 4取代，也可不被R 4取代，具体化学式1可包括：
Figure PCTCN2020105862-appb-000003
但不限于此。其中，任意两者R 4相同或不同。
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，9，9-二甲基芴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：
Figure PCTCN2020105862-appb-000004
均为同一种结构。
本申请提供一种含氮化合物，所述含氮化合物的结构如化学式1所示：
Figure PCTCN2020105862-appb-000005
其中，
Figure PCTCN2020105862-appb-000006
表示化学键；
R 1和R 2分别独立地选自氢、化学式1-1所示的基团，且R 1和R 2有且只有一个为化学式1-1所示的基团，当R 1或R 2选自氢时，选自氢的所述R 1或R 2能被R 4取代；
R 3、R 4分别独立地选自氘、卤素、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为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3～20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；
a选自0，1，2，3或4，当a大于等于2时，任意两个R 3相同或不同；b选自0，1，2或3，当b大于等于2时，任意两个R 4相同或不同；
L选自：单键、取代或未取代的碳原子数为6-30的亚芳基、取代或未取代的碳原子数为3-30的亚杂芳基；
Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基，且所述Ar 1和Ar 2均不为9，9-二苯基芴基。可选地，所述Ar 1和Ar 2均不为螺二芴基。
可选地，所述L、Ar 1和Ar 2的取代基分别独立地选自氘、卤素、氰基、碳原子数为3～18的杂芳基、碳原子数为6～18的芳基、碳原子数为6～20的卤代芳基、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。
还可选地，Ar 1和/或Ar 2的取代基还可以为三苯基硅基。
在本申请中，L、Ar 1和Ar 2的碳原子数，指的是所有碳原子数。举例而言，若L选自取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。
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 PCTCN2020105862-appb-000007
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，术语“取代或未取代的”是指没有取代基或者被一个或多个取代基取代。所述取代基包括但不限于，氘(D)、卤素(例如F、Cl、Br)、氰基、烷基、烯基、炔基、卤代烷基、芳基、杂芳基、芳氧基、芳硫基、环烷基、杂环烷基等。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、N、O、S或P等杂原子且其余原子为碳和氢。未取代的烷基可以是没有任何双键或三键的“饱和烷基基团”。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至20个碳原子，在本申请中，诸如“1至20”的数值范围是指给定范围中的各个整数。举例而言，“1至20个碳原子”是指可 包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的烷基。烷基还可为具有1至10个碳原子的烷基。烷基还可为具有1至6个碳原子的低级烷基。此外，烷基可为取代的或未取代的。
优选地，烷基选自碳原子数为1-10的烷基，具体实例包括但不限于，甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基和己基。
在本申请中，“烯基”是指在直链或支链烃链中包含一个或多个双键的烃基。烯基可为未取代的或取代的。烯基可具有1至20个碳原子，每当在本文出现时，诸如“1至20”的数值范围是指给定范围中的各个整数。举例而言，“1至20个碳原子”是指可包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的烯基。例如，烯基可以为乙烯基、丁二烯、或1,3,5-己三烯。
在本申请中，环烷基指的是含有脂环结构的饱和烃，包含单环和稠环结构。环烷基可具有3-20个碳原子，诸如“3至20”的数值范围是指给定范围中的各个整数。举例而言，“3至20个碳原子”是指可包含3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子、11个碳原子、12个碳原子、13个碳原子、14个碳原子、15个碳原子、16个碳原子、17个碳原子、18个碳原子、19个碳原子或20个碳原子的环烷基。环烷基可为具有3至20个碳原子的小环、普通环或大环。环烷基也可分为单环-只有一个环、双环-两个环、多环-三个或三个以上环。环烷基还可分为两个环共用一个碳原子-螺环、两个环共用两个碳原子-稠环和两个环共用两个以上碳原子-桥环。此外，环烷基可为取代的或未取代的。
优选地，环烷基选自碳原子数为3-10的环烷基，具体施例包括但不限于，环丙基、环丁基、环戊基、环己基和金刚烷基。
在本申请中，芳基指的是衍生自芳香烃环的任选官能团或取代基。芳基可以是单环芳基或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者多个稠环芳基。即，通过碳碳键共轭连接的两个或者多个芳香基团也可以视为本申请的芳基。其中，芳基中不含有B、N、O、S或P等杂原子。举例而言，在本申请中，联苯基、三联苯基等为芳基。芳基的示例可以包括苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、六联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2020105862-appb-000008
基、芴基等，而不限于此。本申请的“芳基”可含有6-30个碳原子，在一些实施方式中，芳基中的碳原子数可以是6-25个，在另一些实施方式中芳基中的碳原子数可以是6-18个，在另一些实施方式中芳基中的碳原子数可以是6-13个。举例而言，芳基的碳原子数量可以是6个、12个、13个、18个、20个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
在本申请中，成环碳原子数指的是，在取代或未取代的芳基、取代或未取代的杂芳基中，位于芳香环上的碳原子数，需要注意的是，作为取代基的芳基和杂芳基的成环碳原子数也考虑在内，芳香环上的其它取代基的碳原子数则不计算在内。举例来讲，芴基的成环碳原子数为13，9,9-二甲芴基的成环碳原子数为13，二苯基芴基的成环碳原子数为25。成环碳原子数为6-20的芳基的成环碳原子数例如可以是6-20个、6-18个、6-14个或6-10个，但不仅限于此。
在本申请中，取代的芳基，指的是芳基中的一个或者多个氢原子被其它基团所取代。例如至少一个氢原子被氘原子、F、Cl、I、CN、羟基、氨基、支链烷基、直链烷基、环烷基、烷氧基、烷胺基或者其他基团取代。可以理解的是，取代的碳原子数为18的芳基，指的是芳基和芳基上的取代基的碳原子总数为18个。举例而言，9,9-二甲基芴基的碳原子数为15，9,9-二苯基芴基和螺二芴基的碳原子数均为25。其中，联苯基可解释为芳基或取代的苯基。
在本申请中，芴基可以被取代，取代的芴基可以为：
Figure PCTCN2020105862-appb-000009
也可以为
Figure PCTCN2020105862-appb-000010
Figure PCTCN2020105862-appb-000011
等。
在本申请中，杂芳基可以是包括B、O、N、P、Si和S中的至少一个作为杂原子的杂芳基。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、N-芳基咔唑基、N-杂芳基咔唑基、N-烷基咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、二苯并甲硅烷基、二苯并呋喃基、苯基取代的二苯并呋喃基、二苯并呋喃基取代的苯基等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基、苯基取代的二苯并呋喃基、二苯并呋喃基取代的苯基等为通过碳碳键共轭连接的多个芳香环体系的杂芳基。
在本申请中，成环碳原子数是指位于芳香环上的碳原子总数，举例来讲，成环碳原子数为3-20的杂芳基指的是杂芳基中位于杂芳环上的碳原子数是3-20个，杂芳基上的取代基中的碳原子数不计算在内。杂芳基中的成环碳原子数可以是3-20个，3-18个、4-18个、3-12个、3-8个，但不限于此。
在本申请中，取代的杂芳基，指的是杂芳基中的一个或者多个氢原子被其基团所取代，例如至少一个氢原子被氘原子、F、Cl、Br、CN、氨基、烷基、卤代烷基、环烷基、芳氧基、芳硫基、硅烷基、烷胺基、芳胺基、硼烷基、膦基或者其他基团取代。
在本申请中，对芳基的解释可应用于亚芳基，对杂芳基的解释同样应用于亚杂芳基。
在本申请中，卤素可以为氟、氯、溴、碘。
本申请的含氮化合物能够用于制备有机电致发光器件和光电转化器件，尤其是适合制备有机电致发光器件和光电转化器件的电子阻挡层(亦称为空穴辅助层、第二空穴传输层等)，以提高有机电致发光器件和光电转化器件的效率和寿命，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，提高光电转化器件和有机电致发光器件的量产稳定性。
可选地，Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为6-20的芳基、碳原子数为3-20的杂芳基。
优选地，L选自单键、取代或未取代的成环碳原子数为6-20的亚芳基、取代或未取代的成环碳原子数为3-20的亚杂芳基。
在一些实施方式中，L选自单键或者如下基团所组成的组：
Figure PCTCN2020105862-appb-000012
其中，
Figure PCTCN2020105862-appb-000013
表示化学键，
Z 1至Z 22分别独立地选自氢、氘、卤素、氰基、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为1-6的烷氧基、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6-20的芳基、碳原子数为6-20的卤代芳基、碳原子数为3-20的杂芳基、碳原子数为3-12的硅烷基、碳原子数为3-10的环烷基；
X选自取代或未取代的碳原子数为1-10的亚烷基、取代或未取代的碳原子数为3-10的亚环烷基、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；X 1至X 10分别独立地表示C或N，且至少一个为N；X 11至X 15分别独立地表示C或N，且至少一个为N；X 16至X 23分别独立地表示C或N，且至少一个为N；X 24、X 25选自分别独立地选自单键、C(R 5R 6)，N(R 7)，O，S，Si(R 5R 6)，Se；优选地，X 24和X 25不能同时为单键；
R 5至R 7分别独立地选自氢、氘、取代或未取代的碳原子数为1-10的烷基、取代或未取代的碳原子数为6-20的芳基、取代或未取代的碳原子数为3-20的杂芳基；
X 26、X 27分别独立地表示C或N，且至少一个为N；
n 1，n 3，n 4，n 6，n 7，n 8，n 9，n 16，n 18，n 21分别独立地选自1，2，3或4；n 10，n 11，n 22分别独立地选自1，2或3；n 13，n 20选自1，2，3，4或5；n 2，n 14，n 19分别独立地选自1，2，3，4， 5或6；n 15选自1，2，3，4，5，6或7；n 5，n 12，n 17分别独立地选自1，2，3，4，5，6，7或8。
可选地，X为碳原子数为1-4的亚烷基、碳原子数为5-10的亚环烷基、碳原子数为6-12的亚芳基、碳原子数为3-12的亚杂芳基。X的具体实例包括但不限于：亚甲基、亚苯基等。
可选地，R 5至R 7分别独立地选自氢、氘、碳原子数为1-4的烷基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基。R 5至R 7的具体实例包括但不限于：甲基、叔丁基、苯基等。
还可选地，Z 1为被氘取代的碳原子数为6-20的芳基，例如为被氘取代的苯基。
按照一种实施方式，L选自单键或者如下基团所组成的组：
Figure PCTCN2020105862-appb-000014
进一步可选地，L选自单键或者如下基团所组成的组：
Figure PCTCN2020105862-appb-000015
可选地，Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为6-20的芳基、碳原子数为3-20的杂芳基。
可选地，Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：成环碳原子数为6-20的芳基、成环碳原子数为5-20的杂芳基。
在一些实施方式中，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
Figure PCTCN2020105862-appb-000016
其中，
Figure PCTCN2020105862-appb-000017
表示化学键；
T 1至T 20分别独立地选自氢、氘、卤素、氰基、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为1-6的烷氧基、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6-20的芳基、碳原子数为6-20的卤代芳基、碳原子数为3-20的杂芳基、碳原子数为3-12的硅烷基、碳原子数为3-10的环烷基；
W选自取代或未取代的碳原子数为1-10的亚烷基、取代或未取代的碳原子数为3-10的亚环烷基、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；W 1、W 2分别独立地表示C或N，且至少一个为N；W 3至W 7分别独立地表示C或N，且至少一个为N；W 8至W 15分别独立地表示C或N，且至少一个为N；W 16、W 17分别独立地选自单键、C(R 9R 10)，N(R 8)，O，S，Si(R 9R 10)，Se；优选地，W 16、W 17不能同时为单键。
R 9至R 10相同或不同，分别独立地选自氢、氘、取代或未取代的碳原子数为1-6的烷基、取代或未取代的碳原子数为7-18的芳基、取代或未取代的碳原子数为3-18的杂芳基；
R 8选自氢、氘、取代或未取代的碳原子数为1-6的烷基、取代或未取代的碳原子数为6-20的芳基、取代或未取代的碳原子数为3-20的杂芳基；
e 1，e 11，e 14，e 15，e 17分别独立地选自1，2，3，4或5；e 16，e 20分别独立地选自1，2或3；e 2，e 9分别独立地选自1，2，3，4，5，6或7；e 3，e 4，e 5分别独立地选自1，2，3，4，5，6，7，8或9；e 6选自1，2，3，4，5，6，7或8；e 7，e 10，e 12，e 13，e 18，e 19分别独立地选自1，2，3或4；e 8选自1，2，3，4，5或6。
可选地，W为碳原子数为1-4的亚烷基、碳原子数为5-10的亚环烷基、碳原子数为6-12的亚芳基、碳原子数为3-12的亚杂芳基。X的具体实例包括但不限于：亚甲基、亚苯基等。
可选地，R 9至R 10分别独立地选自氢、氘、碳原子数为1-4的烷基。R 9至R 10的具体实例包括但不限于：甲基、叔丁基等。
可选地，R 8分别独立地选自氢、氘、碳原子数为1-6的烷基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基。R 8的具体实例包括但不限于：甲基、苯基等。
还可选地，T 1为被氘取代的碳原子数为6-20的芳基，例如为被氘取代的苯基。
可选地，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
Figure PCTCN2020105862-appb-000018
进一步可选地，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
Figure PCTCN2020105862-appb-000019
可选地，所述R 3、R 4分别独立地选自氘、氟、氰基、碳原子数为6-18的芳基、碳原子数为5-18的杂芳基、碳原子数为1-6的烷基、碳原子数为3-10的环烷基。R 3、R 4的具体实例包括但不限于，氘、氟、氰基、甲基、叔丁基、苯基、环戊基、环己基、吡啶基等。
还可选地，所述R 3和/或R 4为被氘取代的苯基。
可选地，所述含氮化合物选自如下化合物所形成的组：
Figure PCTCN2020105862-appb-000020
Figure PCTCN2020105862-appb-000021
Figure PCTCN2020105862-appb-000022
Figure PCTCN2020105862-appb-000023
Figure PCTCN2020105862-appb-000024
Figure PCTCN2020105862-appb-000025
Figure PCTCN2020105862-appb-000026
Figure PCTCN2020105862-appb-000027
Figure PCTCN2020105862-appb-000028
Figure PCTCN2020105862-appb-000029
Figure PCTCN2020105862-appb-000030
Figure PCTCN2020105862-appb-000031
Figure PCTCN2020105862-appb-000032
Figure PCTCN2020105862-appb-000033
Figure PCTCN2020105862-appb-000034
Figure PCTCN2020105862-appb-000035
Figure PCTCN2020105862-appb-000036
Figure PCTCN2020105862-appb-000037
Figure PCTCN2020105862-appb-000038
Figure PCTCN2020105862-appb-000039
Figure PCTCN2020105862-appb-000040
Figure PCTCN2020105862-appb-000041
Figure PCTCN2020105862-appb-000042
Figure PCTCN2020105862-appb-000043
Figure PCTCN2020105862-appb-000044
本申请还提供一种电子元件，所述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的含氮化合物。所述电子元件可用于实现光电转换或者电光转化。
按照一种实施方式，电子元件为有机电致发光器件。如图1所示，有机电致发光器件包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的含氮化合物。
可选地，功能层300包括电子阻挡层322，电子阻挡层322包含本申请所提供的含氮化合物。其中，电子阻挡层322既可以为本申请所提供的含氮化合物组成，也可以由本申请所提供的含氮化合物和其他材料共同组成。
可选地，功能层300包括空穴传输层321和/或空穴注入层310，所述空穴传输层321可以包含有本申请提供的含氮化合物，以提高电子元件中空穴的传输能力。
在本申请的一种具体实施方式中，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、作为能量转化层的有机电致发光层330、电子传输层350和阴极200。本申请提供的含氮化合物可以应用于电子阻挡层322，可以有效改善有机电致发光器件的发光效率和寿命，降低有机电致发光器件的驱动电压。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层321可以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由化合物NPB组成。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的主体材料可以为金属螯合化类化合物、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。例如，有机发光层330的主体材料可以为CBP。
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。例如，有机发光层330的客体材料可以为Ir(ppy) 3。
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自苯并咪唑衍生物、恶二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。例如，电子传输层340可以由ET-1和LiQ组成。
可选地，阴极200包括以下阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括：金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca，但不限于此。优选包括包含铝的金属电极作为阴极。
可选地，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由m-MTDATA组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360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360可以包括LiQ。
可选地，在有机发光层330和电子传输层350之间还可以设置有空穴阻挡层340。
按照另一种实施方式，电子元件可以为光电转化器件。如图2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。
可选地，功能层300包括电子阻挡层322，电子阻挡层322包含本申请所提供的含氮化合物。其中，电子阻挡层322既可以由本申请所提供的含氮化合物组成，也可以由所述含氮化合物和其他材料共同组成。
可选地，如图2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、电子阻挡层322、作为能量转化层的光电转化层370、电子传输层350和阴极200。本申请提供的含氮化合物可以应用于光电转化器件的电子阻挡层322，可以有效改善光电转化器件的发光效率和寿命，提高光电转化器件的开路电压。
可选地，在阳极100和空穴传输层321之间还可以设置有空穴注入层310。
可选地，在阴极200和电子传输层350之间还可以设置有电子注入层360。
可选地，在光电转化层370和电子传输层350之间还可以设置有空穴阻挡层340。
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。按照一种具体的实施方式，太阳能电池包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、光电转化层370、电子传输层350和阴极200，其中，电子阻挡层322包含有本申请的含氮化合物。
本申请还提供一种电子装置，该电子装置包括上述电子元件。由于该电子装置包括上述电子元件，因此具有相同的有益效果，本申请在此不再赘述。
按照一种实施方式，如图3所示，所述电子装置为第一电子装置400，该电子装置包括上述有机电致发光器件。第一电子装置400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，该电子装置包括上述光电转化器件实施方式所描述的任意一种光电转化器件。第二电子装置500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。
以下，通过实施例对本申请进一步详细说明。但是，下述实施例仅是本申请的例示，而并非限定本申请。
化合物合成
通过如下合成路线合成表1所示化合物。
Figure PCTCN2020105862-appb-000045
化合物1的合成
Figure PCTCN2020105862-appb-000046
将2-溴苯硼酸(100.0g,500.0mmol)、1-氯-3碘苯(142.6g,597.6mmol)、四(三苯基膦)钯(11.5g,9.97mmol)、碳酸钾(102g,746mmol)、四丁基溴化铵(32.1g,99.6mmol)、甲苯(800mL)、乙醇(200mL)和去离子水(200mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌2小时；将反应液冷却至室温，加入甲苯(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之后使用二氯甲烷/乙醇体系进行重结晶提纯，得到浅黄色固体中间体I-A-1(64.0g，收率为48％)。
Figure PCTCN2020105862-appb-000047
将镁条(13.54g,564mmol)和乙醚(100mL)置于氮气保护下干燥的圆底烧瓶中，加入碘(100mg)。而后将溶有中间体I-A-1(50.00g,187.0mmol)的乙醚(200mL)溶液缓慢滴入烧瓶中，滴加完毕后升温至35℃，搅拌3小时；将反应液降至0℃，向其中缓慢滴入溶有金刚烷酮(22.45g，149mmol)的乙醚(200mL)溶液，滴加完毕后升温至35℃，搅拌6小时；将反应液冷却至室温，向其中加入5wt％盐酸至pH<7，搅拌1小时，加入乙醚(200mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，得到固体中间体I-A-2(24g,收率48％)。
Figure PCTCN2020105862-appb-000048
将中间体I-A-2(24g,71.0mmol)、三氟乙酸(40.48g,355.0mmol)和二氯甲烷(200mL)加入圆底烧瓶中，氮气保护下搅拌2小时；而后向反应液中加入氢氧化钠水溶液至pH＝8，分液，有机相使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用二氯甲烷/正庚烷(1:2)进行重结晶提纯，得到白色固体状中间体I-A(21g，收率92.5％)。
中间体I-A核磁数据为：
1HNMR(400MHz,CD 2Cl 2):8.11(d,1H),8.03(d,1H),7.41-7.63(m,2H),7.37-7.39(m,1H),7.30-7.33(m,1H),7.23-7.24(m,1H),2.88-2.93(m,2H),2.81-2.85(m,2H),2.19(s,2H),1.99(s,2H),1.77-1.83(m,4H),1.54(s,2H).
Figure PCTCN2020105862-appb-000049
将4-溴联苯(4.0g,17.16mmol)、4-氨基联苯(2.96g,17.5mmol)、三(二亚苄基丙酮)二钯(0.16g,0.17mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.16g,0.34mmol)以及叔丁醇钠(2.47g,25.74mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯，得到淡黄色固体中间体II-A(4.1g,收率72.6％)。
Figure PCTCN2020105862-appb-000050
将中间体I-A(4.1g,12.77mmol)、中间体Ⅱ-A(4.1g,12.77mmol)、三(二亚苄基丙酮)二钯(0.12g,0.13mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.10g,0.25mmol)以及叔丁醇钠(1.84g,19.17mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌1h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯，得到白色固体化合物1(4.35g,收率56.2％)。质谱：m/z＝606.3[M+H] +。
化合物1核磁数据：
1H NMR(400MHz,CD 2Cl 2):8.11(d,1H),8.02(d,1H),7.64-7.60(m,6H),7.55(d,4H),7.43(t,4H),7.33-7.24(m,8H),7.06(dd,1H),2.91(m,4H),2.19(m,2H),2.00(s,2H),1.82(d,4H),1.61(s,2H)。
参照化合物1的合成方法，且使用原料2代替4-溴联苯，使用原料1代替4-氨基联苯合成表1第四列的中间体，并用该第四列的中间体代替中间体Ⅱ-A与中间体I-A合成制备表1中的化合物。具体的化合物编号、结构、原料、最后一步的合成收率、表征数据等展示在表1中。
表1：化合物结构、制备及表征数据
Figure PCTCN2020105862-appb-000051
Figure PCTCN2020105862-appb-000052
Figure PCTCN2020105862-appb-000053
Figure PCTCN2020105862-appb-000054
其中，化合物3的核磁数据为， 1H NMR(CD 2Cl 2,400MHz):8.10(d,1H),8.00(d,1H),7.67-7.59(m,6H),7.54(d,2H),7.45-7.42(m,3H),7.36-7.25(m,8H),7.12(br,1H),7.06(br,1H),2.92(t,4H), 2.19(d,2H),2.00(s,2H),1.82(d,4H),1.61(s,2H),1.44(s,6H)。
化合物7的核磁数据为， 1H NMR(CD 2Cl 2,400MHz):8.11(d,1H),8.03(d,1H),7.91(d,1H),7.85(d,1H),7.62-7.60(m,4H),7.56(d,2H),7.51(d,1H),7.45-7.39(m,3H),7.36-7.26(m,7H),7.21(d,1H),7.07(d,1H),2.92(t,4H),2.19(d,2H),2.00(s,2H),1.82(d,4H),1.62(s,2H)。
化合物54的核磁数据为， 1H NMR(400MHz,CD 2Cl 2):8.11(d,1H),7.99(d,1H),7.66(d,2H),7.63-7.62(m,3H),7.58(d,1H),7.41(d,2H),7.35(s,2H),7.32(t,2H),7.28-7.24(m,4H),7.12(d,2H),7.07(d,1H),2.92(t,4H),2.19(d,2H),2.00(s,2H),1.82(d,4H),1.62(s,2H),1.42(s,12H)。
化合物295的合成
Figure PCTCN2020105862-appb-000055
将中间体Ⅰ-A(10g,31.17mmol)、对氯苯硼酸(3.89g,24.93mmol)、四(三苯基膦)钯(0.72g,0.62mmol)、碳酸钾(6.45g,46.75mmol)、四丁基氯化铵(1.73g,6.23mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌6小时；将反应液冷却至室温，加入甲苯(100mL)进行萃取，合并有机相，使用无水硫酸镁进行干燥，过滤，减压除去溶剂；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体I-B(7.5g，收率75.7％)。
参照中间体I-B的合成方法，不同之处在于以下表2中第二列的原料3替代对氯苯硼酸，合成下表中第三列所示中间体：
表2
Figure PCTCN2020105862-appb-000056
Figure PCTCN2020105862-appb-000057
Figure PCTCN2020105862-appb-000058
将中间体I-A(20.4g；63.7mmol)、联硼酸频哪醇酯(19.4g；76.5mmol)、三(二亚苄基丙酮)二钯(0.6g；0.6mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.6g；1.3mmol)，醋酸钾(12.5g；127.4mmol)和1，4-二氧六环(150mL)加入烧瓶中，氮气保护条件下于100℃回流搅拌16小时；降至室温，向反应液中加入二氯甲烷和水，分液，有机相使用水洗后用无水硫酸镁干燥，减压条件下除去溶剂得到粗品；粗品使用二氯甲烷/正庚烷体系进行硅胶柱色谱提纯，得到白色固体中间体I-A-1(13.3g；51％)。
Figure PCTCN2020105862-appb-000059
将中间体I-A-1(13.3g；32.3mmol)、2-溴7-氯-9,9-二甲基芴(10.9g；35.5mmol)、四三苯基膦钯(0.7g；0.6mmol)、碳酸钾(11.1g；80.7mmol)、四丁基溴化铵(2.1g；6.5mmol)加入烧瓶中，并加入甲苯(80mL)、乙醇(20mL)和水(20mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌24小时；冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体I-A-2(9.0g；54.5％)。
参照中间体I-A-2的合成方法，不同之处在于以下表3中第二列的原料41替代2-溴7-氯-9,9-二甲基芴，合成下表中第三列所示中间体：
表3原料及中间体
Figure PCTCN2020105862-appb-000060
Figure PCTCN2020105862-appb-000061
将4-叔丁基溴苯(4.0g,18.7mmol)、2-氨基联苯(4.39g,25.9mmol)、三(二亚苄基丙酮)二钯(0.23g,0.25mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.24g,0.50mmol)以及叔丁醇钠(3.67g,38.22mmol)加入甲苯(40mL)中，氮气保护下加热至108℃，搅拌2h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯，得到淡黄色固体中间体II-B(3.2g,收率为56.6％)。
Figure PCTCN2020105862-appb-000062
将中间体I-B(1.50g,3.78mmol)、中间体Ⅱ-B(0.95g,3.85mmol)、三(二亚苄基丙酮)二钯(0.03g,0.04mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.03g,0.07mmol)以及叔丁醇钠(0.55g,5.67mmol)加入甲苯(20mL)中，氮气保护下加热至108℃，搅拌5h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用甲苯体系对粗品进行重结晶提纯， 得到白色固体化合物1(1.7g,74％)。质谱：m/z＝662.4[M+H] +。
参照化合物295的合成方法，不同的是，使用原料4代替2-氨基联苯，原料5代替4-叔丁基溴苯合成下表中第四列中间体，并以该第四列的中间体代替中间体Ⅱ-B，制备表4中的化合物，具体的化合物编号、结构、原料、最后一步的合成收率、质谱表征数据等展示在表4中。
表4：化合物编号、结构、制备及表征数据
Figure PCTCN2020105862-appb-000063
Figure PCTCN2020105862-appb-000064
参照中间体I-B的合成方法制备中间体I-A-6，不同的是，将中间体I-A替换为中间体I-A-5，对氯苯硼酸替换为苯硼酸，从而获得中间体I-A-6。
参照化合物1的合成方法，以下表5中第三列所示中间体代替中间体I-A与中间体Ⅱ-A反应，制备表5中第4列所示的化合物，具体的化合物编号、结构、原料、最后一步的合成收率、表征数据等展示在表5中。
表5：化合物编号、结构、制备及表征数据
Figure PCTCN2020105862-appb-000065
Figure PCTCN2020105862-appb-000066
Figure PCTCN2020105862-appb-000067
将1,2-二溴-3-氯苯(80.0g，298.7mmol)、苯硼酸(36.5g，298.7mmol)、四(三苯基膦)钯(6.9g，6.0mmol)、碳酸钾(103.2g，746.7mmol)、四丁基溴化铵(19.2g，59.7mmol)加入烧瓶中，并加入甲苯(600mL)、乙醇(150mL)和水(150mL)的混合溶剂，氮气保护下，升温至80℃，保持温度搅拌18小时；冷却至室温，停止搅拌，反应液水洗后分离有机相，使用无水硫酸镁干燥，减压除去溶剂，得到粗品；使用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体I-G-1(42.0g；收率53％)
Figure PCTCN2020105862-appb-000068
将中间体I-G-1(42.0g；157.9mmol)和四氢呋喃(300mL)加入烧瓶中，氮气保护下，降温至-78℃，于搅拌条件下，滴加正丁基锂的四氢呋喃(2.5M)溶液(95mL；236.9mmol)，滴加完毕后保温搅拌1小时，保持-78℃滴加溶有金刚烷酮(19.0g；126.3mmol)的四氢呋喃(100mL)溶液，滴加完毕后保温1小时后升至室温，搅拌24小时；向反应液中加入盐酸(12M)(26.3mL；315.8mmol)的水(100mL)溶液，搅拌1小时；分液，有机相使用水洗至中性，加入无水硫酸镁干燥，减压除去溶剂得到粗品；使用乙酸乙酯/正庚烷体系对粗品进行硅胶柱色谱提纯，得到白色固体产物中间体I-G-2(25.8g；收率60％)
Figure PCTCN2020105862-appb-000069
参照中间体I-A的合成方法，不同的是，使用中间体I-G-2代替中间体I-A-2，合成中间体I-G。
参照化合物1的合成方法，不同的是，使用中间体I-G代替I-A，用下表中第二列的原料6代替4-氨基联苯，第三列的原料7代替4-溴联苯，原料6与原料7合成第四列的中间体代替中间体Ⅱ-A，制备表6中第五列所示的化合物。具体的化合物编号、结构、最后一步的合成收率、表征数据等展示在表6中。
表6：化合物编号、结构、制备及表征数据
Figure PCTCN2020105862-appb-000070
Figure PCTCN2020105862-appb-000071
Figure PCTCN2020105862-appb-000072
参照中间体I-B的合成方法，不同的是，使用中间体I-G代替中间体I-A，合成中间体I-G-1。
参照化合物295的合成方法，不同的是，使用中间体I-G-1代替I-B，制备化合物439。具体的化合物、最后一步的合成收率、表征数据等展示在表7中。
表7：化合物编号、结构、制备及表征数据
Figure PCTCN2020105862-appb-000073
有机电致发光器件制备及评估
实施例1
通过如下方法制备绿色有机电致发光器件
将ITO厚度为
Figure PCTCN2020105862-appb-000074
的ITO基板(康宁制造)切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀m-MTDATA以形成厚度为
Figure PCTCN2020105862-appb-000075
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀NPB，以形成厚度为
Figure PCTCN2020105862-appb-000076
的第一空穴传输层。
在第一空穴传输层上蒸镀化合物1，形成厚度为
Figure PCTCN2020105862-appb-000077
的第二空穴传输层。
将CBP作为主体材料，按照膜厚比100:5同时掺杂Ir(ppy) 3，形成厚度为
Figure PCTCN2020105862-appb-000078
的发光层(EML)。
将ET-1和LiQ以1:1的重量比进行混合并蒸镀形成
Figure PCTCN2020105862-appb-000079
厚的电子传输层(ETL)，将LiQ蒸镀在电子传输层上以形成厚度为
Figure PCTCN2020105862-appb-000080
的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1:9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2020105862-appb-000081
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2020105862-appb-000082
的CP-1，从而完成有机发光器件的制造。
其中，在制备电致发光器件时，所使用的各个材料的结构如下：
Figure PCTCN2020105862-appb-000083
实施例2-实施例43
利用下表8中合成的化合物分别替代化合物1，形成厚度为
Figure PCTCN2020105862-appb-000084
的第二空穴传输层，制备相应的绿色有机电致发光器件。
对比例1至对比例7
对比例1至对比例7中，分别利用化合物A、化合物B、化合物C、化合物D、化合物E、化合物F、化合物G分别替代化合物1，按照相同的方法，制备相应的绿色有机电致发光器件。化合物A至化合物G的结构如下所示：
Figure PCTCN2020105862-appb-000085
对实施例1-43和对比例1-7制备所得的绿色有机电致发光器件进行性能测试，具体在10mA/cm 2的条件下测试了器件的IVL性能，T95器件寿命在初始亮度17,000nit下进行测试，测试结果展示在表8中。
表8绿色有机电致发光器件的性能测试结果
Figure PCTCN2020105862-appb-000086
Figure PCTCN2020105862-appb-000087
根据上表可知，在色坐标相差不大的情况下，相较于对比例1～7而言，实施例1～43制备的有机电致发光器件的发光效率(Cd/A)和寿命与对比例1～7相当，但是对比例1～7的器件电压整体偏高，如上表所示，与对比例1～7相比，实施例1～43的器件电压至少降低了0.45V。因此，在第二空穴传输层中使用本申请的含氮化合物可制备得到工作电压较低的有机电致发光器件。
本申请的含氮化合物在芴的侧位引入金刚烷基结构，通过超共轭效应提升芴环以及整个化合物的共轭体系的电子密度，可以增强含氮化合物的空穴传导率以及电子耐受度，不仅如此，引入的金刚烷基还可以增加含氮化合物的分子量并降低分子对称性，可以提高本申请化合物的玻璃化转变温度以及蒸镀温度，控制含氮化合物的结晶性，使得氮化合物用于量产时有更佳的物理和热学稳定性，进而便于有机电致发光器件和光电转化器件的量产稳定性。相较于对比例1、2、3，将胺与芴的1、3号位连接，能一定程度的提高芳胺结构的空间位阻，增大芴平面与芳胺平面(尤其是三芳胺平面)的扭曲角度，从而降低含氮化合物的共轭程度，这使得将该含氮化合物作为第二空穴传输层(亦称为电子阻挡层)时能更好的与相邻层的HOMO能级匹配，进而降低了有机电致发光器件的工作电压。
将实施例1所制备的有机电致发光器件分为两组，其中一组器件不经过热处理直接进行性能测试，测试结果参见表9。另一组经过热处理(110℃下放置1小时)后再进行性能测试，性能测 试结果参见表10。参照上述方法，分别获得实施例1、实施例14、实施例21、实施例32、实施例35、实施例38、实施例41、对比例1～7所制备的有机电致发光器件不进行热处理的性能参数和热处理后的性能参数。
表9有机发光器件不进行热处理的性能参数
Figure PCTCN2020105862-appb-000088
表10有机发光器件进行热处理后的性能参数
Figure PCTCN2020105862-appb-000089
从表9和表10的结果可知，与热处理前相比，对比例1、对比例2、对比例4～7的有机电 致发光器件在热处理后减少了约23％以上的发光效率以及外量子效率，寿命方面在热处理后减少了10％以上。对比例3热处理后的有机电致发光器件的效率和寿命与热处理前相比效率降低了5.8％，寿命降低了6.5％；而实施例1、实施例14、实施例21、实施例35、实施例38和实施例41的有机电致发光器件在热处理后，仍保持与热处理前同等的效率和寿命。
从表8-表10的器件结果可知，本发明的化合物与对比例1和对比例3相比，电压降低，究其原因，可能在于本发明化合物在金刚烷芴1，3号比金刚烷芴2号位具有更深的HOMO，从而使空穴向发光层的注入更为顺畅。本发明化合物与对比例5、对比例6和对比例7相比，电压降低且热稳定性能提升，究其原因可能在于在于，本发明9,9-二甲基芴上所形成的环烷基为刚性大体积的金刚烷基，相比于单环结构，其在降低分子堆叠方面的能力更强，可使材料达到更为稳定的膜层状态。
可见，根据所述实施例的有机电发光器件的结果的表8-表10可知，当以金刚烷-芴为核心的芳基胺化合物用作绿光器件的第二空穴传输层材料时，可制造驱动电压、发光效率、外量子效率以及热稳定性等特性优异的高效率、高耐热性、长寿命的有机电致发光器件。
应可理解的是，本申请不将其应用限制到本说明书提出的部件的详细结构和布置方式。本申请能够具有其他实施方式，并且能够以多种方式实现并且执行。前述变形形式和修改形式落在本申请的范围内。应可理解的是，本说明书公开和限定的本申请延伸到文中和/或附图中提到或明显的两个或两个以上单独特征的所有可替代组合。所有这些不同的组合构成本申请的多个可替代方面。本说明书所述的实施方式说明了已知用于实现本申请的最佳方式，并且将使本领域技术人员能够利用本申请。

Claims (16)

  1. 一种含氮化合物，其特征在于，所述含氮化合物的结构如化学式1所示：
    Figure PCTCN2020105862-appb-100001
    其中，
    Figure PCTCN2020105862-appb-100002
    表示化学键；
    R 1和R 2分别独立地选自氢、化学式1-1所示的基团，且R 1和R 2有且只有一个为化学式1-1所示的基团，当R 1或R 2选自氢时，选自氢的所述R 1或R 2能被R 4取代；
    R 3、R 4分别独立地选自氘、卤素、氰基、碳原子数为3～20的杂芳基、碳原子数为6～20的芳基、碳原子数为3～12的三烷基硅基、碳原子数为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3～20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；
    a选自0，1，2，3或4，当a大于等于2时，任意两个R 3相同或不同；
    b选自0，1，2或3，当b大于等于2时，任意两个R 4相同或不同；
    L选自：单键、取代或未取代的碳原子数为6-30的亚芳基、取代或未取代的碳原子数为3-30的亚杂芳基；
    Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为1-20的烷基、碳原子数为3-20的环烷基、碳原子数为6-30的芳基、碳原子数为3-30的杂芳基，且所述Ar 1和Ar 2均不为9，9-二苯基芴基。
  2. 根据权利要求1所述的含氮化合物，其特征在于，所述L、Ar 1和Ar 2的取代基分别独立地选自氘、卤素、氰基、碳原子数为3～18的杂芳基、碳原子数为6～18的芳基、碳原子数为6～20的卤代芳基、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。
  3. 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、取代或未取代的成环碳原子数为6-20的亚芳基、取代或未取代的成环碳原子数为3-20的亚杂芳基。
  4. 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 PCTCN2020105862-appb-100003
    Figure PCTCN2020105862-appb-100004
    其中，
    Figure PCTCN2020105862-appb-100005
    表示化学键，
    Z 1至Z 22分别独立地选自氢、氘、卤素、氰基、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为1-6的烷氧基、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6-20的芳基、碳原子数为6-20的卤代芳基、碳原子数为3-20的杂芳基、碳原子数为3-12的硅烷基、碳原子数为3-10的环烷基；
    X选自取代或未取代的碳原子数为1-10的亚烷基、取代或未取代的碳原子数为3-10的亚环烷基、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；
    X 1至X 10分别独立地表示C或N，且至少一个为N；
    X 11至X 15分别独立地表示C或N，且至少一个为N；
    X 16至X 23分别独立地表示C或N，且至少一个为N；
    X 24、X 25分别独立地选自单键、C(R 5R 6)，N(R 7)，O，S，Si(R 5R 6)，Se；
    R 5至R 7分别独立地选自氢、氘、取代或未取代的碳原子数为1-10的烷基、取代或未取代的碳原子数为6-20的芳基、取代或未取代的碳原子数为3-20的杂芳基；
    X 26、X 27分别独立地表示C或N，且至少一个为N；
    n 1，n 3，n 4，n 6，n 7，n 8，n 9，n 16，n 18，n 21分别独立地选自1，2，3或4；
    n 10，n 11，n 22分别独立地选自1，2或3；
    n 13，n 20选自1，2，3，4或5；
    n 2，n 14，n 19分别独立地选自1，2，3，4，5或6；
    n 15选自1，2，3，4，5，6或7；
    n 5，n 12，n 17分别独立地选自1，2，3，4，5，6，7或8。
  5. 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 PCTCN2020105862-appb-100006
  6. 根据权利要求1所述的含氮化合物，其特征在于，Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：碳原子数为6-20的芳基、碳原子数为3-20的杂芳基。
  7. 根据权利要求1所述的含氮化合物，其特征在于，Ar 1和Ar 2分别独立地选自以下取代或未取代的基团：成环碳原子数为6-20的芳基、成环碳原子数为5-20的杂芳基。
  8. 根据权利要求1所述的含氮化合物，其特征在于，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
    Figure PCTCN2020105862-appb-100007
    其中，
    Figure PCTCN2020105862-appb-100008
    表示化学键；
    T 1至T 20分别独立地选自氢、氘、卤素、氰基、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为1-6的烷氧基、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6-20的芳基、碳原子数为6-20的卤代芳基、碳原子数为3-20的杂芳基、碳原子数为3-12的硅烷基、碳原子数为3-10的环烷基；
    W选自取代或未取代的碳原子数为1-10的亚烷基、取代或未取代的碳原子数为3-10的亚环烷基、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；
    W 1、W 2分别独立地表示C或N，且至少一个为N；W 3至W 7分别独立地表示C或N，且至少一个为N；W 8至W 15分别独立地表示C或N，且至少一个为N；W 16、W 17分别独立地选自单键、C(R 9R 10)，N(R 8)，O，S，Si(R 9R 10)，Se；
    R 9至R 10相同或不同，分别独立地选自氢、氘、取代或未取代的碳原子数为1-6的烷基、取代或未取代的碳原子数为7-18的芳基、取代或未取代的碳原子数为3-18的杂芳基；
    R 8选自氢、氘、取代或未取代的碳原子数为1-6的烷基、取代或未取代的碳原子数为6-20的芳基、取代或未取代的碳原子数为3-20的杂芳基；
    e 1，e 11，e 14，e 15，e 17分别独立地选自1，2，3，4或5；e 16，e 20分别独立地选自1，2或3；
    e 2，e 9分别独立地选自1，2，3，4，5，6或7；e 3，e 4，e 5分别独立地选自1，2，3，4，5，6，7，8或9；e 6选自1，2，3，4，5，6，7或8；e 7，e 10，e 12，e 13，e 18，e 19分别独立地选自1，2，3或4；e 8选自1，2，3，4，5或6。
  9. 根据权利要求1所述的含氮化合物，其特征在于，Ar 1和Ar 2分别独立地选自如下基团所组成的组：
    Figure PCTCN2020105862-appb-100009
  10. 根据权利要求1所述的含氮化合物，其特征在于，所述R 3、R 4分别独立地选自氘、氟、氰基、碳原子数为6-18的芳基、碳原子数为5-18的杂芳基、碳原子数为1-6的烷基、碳原子数为3-10的环烷基。
  11. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下化合物所形成的组：
    Figure PCTCN2020105862-appb-100010
    Figure PCTCN2020105862-appb-100011
    Figure PCTCN2020105862-appb-100012
    Figure PCTCN2020105862-appb-100013
    Figure PCTCN2020105862-appb-100014
    Figure PCTCN2020105862-appb-100015
    Figure PCTCN2020105862-appb-100016
    Figure PCTCN2020105862-appb-100017
    Figure PCTCN2020105862-appb-100018
    Figure PCTCN2020105862-appb-100019
    Figure PCTCN2020105862-appb-100020
    Figure PCTCN2020105862-appb-100021
    Figure PCTCN2020105862-appb-100022
    Figure PCTCN2020105862-appb-100023
    Figure PCTCN2020105862-appb-100024
    Figure PCTCN2020105862-appb-100025
    Figure PCTCN2020105862-appb-100026
    Figure PCTCN2020105862-appb-100027
    Figure PCTCN2020105862-appb-100028
    Figure PCTCN2020105862-appb-100029
    Figure PCTCN2020105862-appb-100030
    Figure PCTCN2020105862-appb-100031
    Figure PCTCN2020105862-appb-100032
    Figure PCTCN2020105862-appb-100033
    Figure PCTCN2020105862-appb-100034
  12. 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1-11任一项所述的含氮化合物。
  13. 根据权利要求12所述的电子元件，其特征在于，所述功能层包括电子阻挡层，所述电子阻挡层包括所述的含氮化合物。
  14. 根据权利要求12或13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。
  15. 根据权利要求14所述的电子元件，其特征在于，所述有机电致发光器件为绿光器件。
  16. 一种电子装置，其特征在于，包括权利要求12-15任一项所述的电子元件。
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