WO2021136006A1 - 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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WO2021136006A1
WO2021136006A1 PCT/CN2020/138112 CN2020138112W WO2021136006A1 WO 2021136006 A1 WO2021136006 A1 WO 2021136006A1 CN 2020138112 W CN2020138112 W CN 2020138112W WO 2021136006 A1 WO2021136006 A1 WO 2021136006A1
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group
carbon atoms
groups
independently selected
nitrogen
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PCT/CN2020/138112
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French (fr)
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张林伟
马天天
南朋
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陕西莱特光电材料股份有限公司
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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.
  • KR1020130106255A, KR1020180137315A, CN108137500A, etc. have applied for materials that can be used to prepare hole transport layers in organic electroluminescent devices.
  • the purpose of this application is to provide a nitrogen-containing compound, organic electroluminescent device and electronic device to improve the performance of the organic electroluminescent device and electronic device.
  • a nitrogen-containing compound is provided, and the structure of the nitrogen-containing compound is shown in Chemical Formula 1:
  • L is a group containing a substituted or unsubstituted adamantane spiro-attached fluorene ring
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
  • the substituents in Ar 1 , Ar 2 and L are the same or different, and are each independently selected from: deuterium, tritium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, and 3 carbon atoms.
  • the number of atoms is 6-18 aryloxy groups
  • the number of carbon atoms is 6-18 arylthio groups
  • the number of carbon atoms is 6-18 arylsilyl groups
  • the number of carbon atoms is 6-18 alkylsilyl 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.
  • an electronic device including the above-mentioned electronic component.
  • the carbazole and the triarylamine group are connected through a fluorene ring with adamantane screw connection.
  • the fluorene ring with adamantane screw connection has electron-rich characteristics.
  • the material When it is combined with triarylamine, the material will have high holes Mobility: This group has strong rigidity at the same time. When it is connected with the carbazole group, it can effectively increase the energy of the first triplet state of the material. Therefore, when the material is used as the electron blocking layer of the organic electroluminescent device, It can prevent the outflow of excitons while ensuring the efficiency of hole injection into the light-emitting layer, thereby improving the light-emitting efficiency and lifetime of the device.
  • 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 diagram of the structure of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 3 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of an electronic device according to another 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; 340, hole blocking layer; 350, electron transport 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • the present application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in Chemical Formula 1:
  • L is a group containing a substituted or unsubstituted adamantane spiro-linked fluorene ring
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
  • the substituents in Ar 1 , Ar 2 and L are the same or different, and are each independently selected from: deuterium, tritium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, and 3 carbon atoms.
  • the number of atoms is 6-18 aryloxy groups
  • the number of carbon atoms is 6-18 arylthio groups
  • the number of carbon atoms is 6-18 arylsilyl groups
  • the number of carbon atoms is 6-18 alkylsilyl groups.
  • the number of carbon atoms of Ar 1 and Ar 2 refers to the total number of carbon atoms.
  • Ar 2 is selected from substituted aryl groups with 22 carbon atoms, the number of all carbon atoms of the aryl group and its substituents is 22; if Ar 1 is selected from substituted aryl groups with 20 carbon atoms
  • all carbon atoms of the heteroaryl and the substituents on it are 20.
  • 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 Rs).
  • substituted or unsubstituted aryl group refers to an aryl group having a substituent Rs or an unsubstituted aryl group.
  • the above-mentioned substituents can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, trialkylsilyl group, alkyl group, haloalkyl group, cycloalkyl group, alkoxy group, etc.; when the same When two substituents Rs are connected to an atom, the two substituents Rs can exist independently or are connected to each other to form a ring with the atoms to which they are connected together; when there are two adjacent substituents Rs on the functional group, adjacent The two substituents Rs may exist independently or be fused to form a ring with the functional group to which they are connected.
  • 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, O, N, P, Si, or S.
  • biphenyl, terphenyl, etc. are aryl groups.
  • aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrene Group, benzofluoranthene group, Group, fluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, etc., but not limited thereto.
  • a substituted aryl group means that one or more of the hydrogen atoms in the aryl group are replaced by other groups.
  • at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, I, cyano, aryl, heteroaryl, branched alkyl, linear alkyl, cycloalkyl, alkoxy 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.
  • the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si, Se, 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, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofur
  • thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple conjugated groups connected by carbon-carbon bonds.
  • Heteroaryl groups of aromatic ring systems are heteroaryl groups of aromatic ring systems.
  • the substituted heteroaryl group can be one or more of the hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group. , Cycloalkyl, alkoxy, alkylthio and other groups are substituted. 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.
  • 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.
  • the non-positioned connecting bond refers to the single bond protruding from the ring system " ", which means that one end of the bond can be connected to any position in the ring system through which 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 phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-positional bond extending from the middle of the benzene ring on one side, which represents The meaning of includes any possible connection modes shown in formula (X'-1) to formula (X'-4).
  • the non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system.
  • the substituent R'represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and the meaning represented by it includes formulas (Y-1) to Any possible connection mode shown in formula (Y-7).
  • the alkyl group having 1-10 carbon atoms may include a straight-chain alkyl group having 1-10 carbon atoms and a branched alkyl group having 3-10 carbon atoms.
  • the number of carbon atoms may be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, for example.
  • alkyl groups having 1-10 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 may include fluorine, bromine, chlorine, iodine and the like.
  • the number of carbon atoms of the aryl group as a substituent is 6-20, and the number of carbon atoms of the aryl group may be 6, 10, 12, 14, 15, 18, 20, etc., for example.
  • Specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, phenanthryl, fluorenyl, and the like.
  • the number of carbon atoms of the heteroaryl group as a substituent is 3-20, and the number of carbon atoms of the heteroaryl group may be 3, 4, 5, 7, 8, 9, 12, 18, 20, etc., for example.
  • Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
  • alkylsilyl group refers to a group formed by a silane substituted with one or more than two alkyl groups, for example, it may be a group formed by substituting a silane with one alkyl group (R).
  • group( ) can be a group formed by substituting two alkyl groups (R) for monosilane ( ), it can also be a group ( That is, trialkylsilyl).
  • the alkylsilyl group is a trialkylsilyl group.
  • the meanings of the terms "silyl group” and “alkylsilyl group” in this application can be interchanged.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • cycloalkyl groups having 3-10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • fluorene ring spiro-attached by unsubstituted adamantane has the structure shown below:
  • L is a group containing a substituted or unsubstituted adamantane spiro-linked fluorene ring
  • L group as a linking group contains a substituted or unsubstituted adamantane spiro-linked fluorene ring
  • other groups are optionally included, such as a substituted or unsubstituted benzene ring, and the other groups may be connected to the fluorene ring through a single bond.
  • L may be a substituted or unsubstituted adamantane spiro-linked fluorene ring.
  • L can also be a group formed by a substituted or unsubstituted adamantane spiro-linked fluorene ring and a substituted or unsubstituted benzene ring; the structure of the group L is composed of an unsubstituted adamantane
  • the connection between the two can be as follows:
  • L is selected from the group consisting of the following formulas 1-1 to 1-4:
  • R 1 to R 11 are the same or different, and are each independently selected from deuterium, tritium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, silyl group with 3-10 carbon atoms, number of carbon atoms Cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkoxy groups with 1-10 carbon atoms, and 1-10 carbon atoms ⁇ alkylthio;
  • R 1 to R 11 represents R & lt m
  • n-1 to n-11 to n-m represents
  • m represents the number of R & lt n-m
  • n 1 , n 2 , n 3 , n 4 , n 5 , n 6 , n 8 , n 11 are the same or different, and are each independently selected from 0, 1, 2 or 3; n 7 , n 9 , n 10 is selected from 0, 1, 2, 3 or 4; when n m is greater than 1, any two R m are the same or different.
  • the R 1 to R 11 are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1-4 carbon atoms, and silanes with 3-10 carbon atoms.
  • R 1 to R 11 are the same or different, and are each independently selected from deuterium, tritium, fluorine, cyano, alkyl with 1-4 carbon atoms, and trialkyl with 3-7 carbon atoms Silicon group, cycloalkyl group having 5-10 carbon atoms, aryl group having 6-12 carbon atoms, heteroaryl group having 5-10 carbon atoms, alkoxy group having 1-4 carbon atoms, Alkylthio group having 1 to 4 carbon atoms.
  • R 1 to R 11 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trimethylsilyl, ring Pentyl, cyclohexyl, phenyl, naphthyl, pyridyl, methoxy, ethoxy, methylthio, ethylthio.
  • n 1 to n 11 are each independently selected from 0, 1, or 2.
  • the substituents in Ar 1 , Ar 2 and L are the same or different, and are independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-7 carbon atoms, carbon atom Cycloalkyl groups with 5-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 5-20 carbon atoms, alkoxy groups with 1-7 carbon atoms, 1 carbon atoms -7 alkylthio, 6-10 aryloxy, and 6-10 arylthio.
  • the substituents in Ar 1 , Ar 2 and L are the same or different, and are independently selected from: deuterium, halogen group, cyano group, alkyl group having 1 to 4 carbon atoms, carbon Cycloalkyl groups with 5-10 atoms, aryl groups with 6-15 carbon atoms (e.g., aryl groups with 6-12 carbon atoms, aryl groups with 15 carbon atoms), 5-carbon atoms 12 heteroaryl groups, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having 1 to 4 carbon atoms, trialkylsilyl groups having 3 to 7 carbon atoms, and triphenylsilyl groups.
  • the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, tri Methylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, phenanthryl, 9,9-dimethylfluorenyl, dipyridyl, methoxy, ethoxy, methylthio, ethylthio , Trimethylsilyl, triphenylsilyl, dibenzofuranyl, dibenzothienyl, etc.
  • the substituents in L are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trimethylsilyl, ring Pentyl, cyclohexyl, phenyl, naphthyl, pyridyl, methoxy, ethoxy, methylthio, ethylthio, etc.
  • the Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-25 carbon atoms.
  • Ar 1 and Ar 2 are each independently selected from carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30 substituted or unsubstituted aryl groups, or selected from 3, 4, 5, 6, 7, 8, 9, 12, 16, 18, 20, 21, 22, 23, 24, 25 substituted or unsubstituted heteroaryl.
  • the Ar 1 and Ar 2 are each independently selected from the group consisting of the following chemical formula i-1 to chemical formula i-15:
  • M 1 is selected from a single bond or
  • G 1 to G 5 are each independently selected from N or C(F 1 ), and at least one of G 1 to G 5 is selected from N; when two or more of G 1 to G 5 are selected from C(F 1 ) , Any two F 1 are the same or different;
  • G 6 to G 13 are each independently selected from N or C(F 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(F 2 ) , Any two F 2 are the same or different;
  • G 14 to G 23 are each independently selected from N or C(F 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(F 3 ) , Any two F 3 are the same or different;
  • G 24 to G 33 are each independently selected from N or C(F 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(F 4 ) , Any two F 4 are the same or different;
  • H 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and those having 3 to 10 carbon atoms Cycloalkyl, alkoxy having 1 to 10 carbon atoms, and alkylthio having 1 to 10 carbon atoms;
  • H 2 to H 9 and H 21 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms Group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a heteroaryl group having 3 to 18 carbon atoms;
  • H 10 to H 20 and F 1 to F 4 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and 1 to carbon atoms 10 alkyl groups, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkylthio groups having 1 to 10 carbon atoms, aryl groups having 6 to 18 carbon atoms Group, heteroaryl group having 3 to 18 carbon atoms;
  • H 1 ⁇ H 21 are represented by H k
  • h 1 ⁇ h 21 are represented by h k
  • k represents a variable and is selected from any integer from 1 to 21
  • h k represents the number of substituents H k ; where, when k When k is selected from 5 or 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 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 selected from 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; when h k is greater than 1, any two H
  • K 1 is selected from O, S, Se, N (H 22 ), C (H 23 H 24 ), Si (H 23 H 24 ); wherein, H 22 , H 23 , and H 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, or a cycloalkyl group having 3 to 10 carbon atoms, or the above H 23 and H 24 are connected to each other to form a ring with the atoms they are commonly connected to;
  • K 2 is selected from a single bond, O, S, Se, N (H 25 ), C (H 26 H 27 ), Si (H 26 H 27 ); wherein, H 25 , H 26 , and H 27 are each independently selected from : C6-C20 aryl group, C3-C20 heteroaryl group, C1-C10 alkyl group or C3-C10 cycloalkyl group, or the above H 26 and H 27 are connected to each other to form a ring with the atoms to which they are commonly connected.
  • F 1 to F 4 can be represented by F f , where f is a variable and represents 1, 2, 3, or 4. For example, when f is 2, F f refers to F 2 . It should be appreciated that, when not connected to the positioning linkage C (F f) a, C (F f) F f is absent.
  • C (F f) F f when " When connected to G 12 , G 12 can only represent C atom, that is, the structure of chemical formula i-13 is:
  • the ring formed by connecting two groups in each group may be saturated or unsaturated with 3 to 15 carbon atoms.
  • the ring in chemical formula i-10, when K 2 and M 1 are both single bonds, H 19 is hydrogen, and K 1 is C (H 23 H 24 ), H 23 and H 24 are connected to each other to share them When the connected atoms form a 5-membered ring, the formula i-10 is Similarly, the chemical formula i-10 can also represent That is, H 23 and H 24 are connected to each other to form a partially unsaturated 13-membered ring with their common atoms.
  • the Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted group Z; wherein, the unsubstituted group Z is selected from the group consisting of the following groups:
  • the substituted group Z has one or more than two substituents, and the substituents are independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, and cycloalkane with 3-10 carbon atoms Group, alkoxy group having 1-4 carbon atoms, alkylthio group having 1-4 carbon atoms, trialkylsilyl group having 3-7 carbon atoms, pyridyl, phenyl, naphthyl, three Phenylsilyl; when the number of substituents is two or more, any two substituents are the same or different.
  • the substituents are independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, Methylthio, ethylthio, cyclopentyl, cyclohexyl, trimethylsilyl, triphenylsilyl, pyridyl, phenyl, naphthyl.
  • the Ar 1 and Ar 2 are each independently selected from the group consisting of:
  • Ar 1 and Ar 2 are each independently selected from the group consisting of:
  • the structure of the nitrogen-containing compound may be selected from the group consisting of the following formula A to formula D:
  • the nitrogen-containing compound is selected from the group consisting of the following compounds:
  • the application also provides an electronic component, the electronic component comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound of the application .
  • the electronic component is an organic electroluminescent device.
  • the organic electroluminescent device includes 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 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 organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light emitting layer 330 as an energy conversion layer, and an electron transport layer 350 which are sequentially stacked. And cathode 200.
  • the nitrogen-containing compound provided in the present application can be applied to the electron blocking layer 322 of an organic electroluminescent device, effectively improving the luminous efficiency and lifetime of the organic electroluminescent device, and reducing 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 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 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 light-emitting layer 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 may 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 CBP or ⁇ , ⁇ -ADN.
  • 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(piq) 2 (acac) or BD-1 (the structure is shown below).
  • the electron transport layer 350 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 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 350 may be composed of TPBi 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 silver and magnesium 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 of injecting holes into the hole transport layer 321.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application.
  • the hole injection layer 310 may be composed of HAT-CN or F4-TCNQ.
  • an electron injection layer 360 may be further provided between the cathode 200 and the electron transport layer 350 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 be composed of Yb.
  • a hole blocking layer 340 may also be provided between the organic electroluminescent layer 330 and the electron transport layer 350.
  • the organic electroluminescent device is a red light device or a blue light device.
  • the electronic component is a photoelectric conversion device.
  • the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer disposed between the anode 100 and the cathode 200. 300;
  • 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 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.
  • a 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 application also provides an electronic device, which includes the electronic component described in the second aspect of the 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 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 a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • Extract combine the organic phases, wash with water to neutrality, dry with anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure, add the obtained oily substance to the flask with n-heptane, heat to reflux to a clear solution, and place in- It was recrystallized at 20°C to obtain a white intermediate l-A1-2 (61 g, yield 65.3%).
  • NMR of compound 51 1 H NMR (400MHz, CD 2 Cl 2 ): 8.24 (d, 2H), 8.06 (d, 2H), 7.86-7.78 (m, 10H), 7.75-7.66 (m, 6H), 7.59 -7.52 (m, 4H), 7.24 (d, 3H), 6.49-6.44 (m, 5H), 2.91 (d, 2H), 2.61 (d, 2H), 2.16 (s, 1H), 1.90 (s, 3H) ), 1.77(d, 2H), 1.69(d, 2H), 1.60(s, 2H).
  • the compound was prepared according to the same synthetic method as compound 51, except that in step (6), the intermediates in Table 1 were used instead of intermediates II-A1.
  • the raw materials used and the corresponding synthesized compounds, the yield of the last step, and the compound mass spectrum characterization results are shown in Table 1.
  • the compound was prepared according to the same synthetic method as compound 123, except that the intermediates in Table 2 were used instead of intermediate IV-A1.
  • the raw materials used and the corresponding synthesized compounds, the yield of the last step, and the compound mass spectrum characterization results are shown in Table 2.
  • Extract combine the organic phases, wash with water to neutrality, dry with anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure, add the obtained oily substance to the flask with n-heptane, heat to reflux to a clear solution, and place in- Recrystallized at 20°C to obtain a white intermediate VA-1 (122 g, yield 84.7%).
  • the intermediate VA-4 (11.9g, 25mmol), carbazole (4.18g, 25mmol), tris(dibenzylideneacetone) two palladium (0.23g, 0.25mmol), 2-dicyclohexylphosphorus-2', 6'-Dimethoxybiphenyl (0.21g, 0.5mmol) and sodium tert-butoxide (3.61g, 37.5mmol) were added to toluene (120mL), heated to 108°C under nitrogen protection, stirred for 3h; then cooled to room temperature The reaction solution was washed with water and then dried by adding magnesium sulfate. After filtration, the filtrate was depressurized to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain a white solid intermediate VA (7.2 g, yield 51.4%).
  • the compound was prepared according to the synthetic method of compound 141, except that in step (6), the intermediates in Table 3 were used instead of intermediates II-A1.
  • the raw materials used and the corresponding synthesized compounds, the yield of the last step, and the compound mass spectrum characterization results are shown in Table 3.
  • the organic electroluminescent device 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 cathode, anode, and insulating layer patterns. 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.
  • the compound HAT-CN was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL);
  • the compound NPB is vacuum-evaporated on the hole injection layer to form a thickness of The hole transport layer (HTL).
  • HTL hole transport layer
  • compound 51 was vapor-deposited as an electron blocking layer (EBL) with a thickness of .
  • EBL electron blocking layer
  • the electron blocking layer is vapor-deposited with compound CBP as the main body and doped with Ir(piq) 2 (acac) with a film thickness ratio of 3% to form a thickness of Organic light emitting layer (EML).
  • the organic light-emitting layer is doped with TPBi and LiQ as the electron transport layer (ETL) according to the evaporation ratio of 1:1.
  • the thickness is .
  • Yb is vapor-deposited on the electron transport layer to form a thickness of The electron injection layer (EIL).
  • magnesium (Mg) and silver (Ag) were vacuum vapor-deposited on the electron injection layer at a film thickness ratio of 1:9 to form a thickness of The cathode.
  • the compound CP-1 is vapor-deposited on the cathode as an organic covering layer (CPL) with a thickness of
  • the vapor-deposited device is encapsulated with ultraviolet hardening resin in a nitrogen glove box (the content of water and oxygen needs to be strictly controlled) to prevent the device from being corroded by external moisture or other substances.
  • 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 cathode, anode and insulating layer patterns, 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 Hole injection layer (HIL), and NPB is vapor-deposited on the hole injection layer to form a thickness of The hole transport layer.
  • HIL Hole injection layer
  • Compound 51 was vacuum-evaporated on the hole transport layer to form a thickness of The electron blocking layer (EBL).
  • EBL electron blocking layer
  • ⁇ , ⁇ -ADN is used as the main body, and BD-1 is simultaneously doped according to the film thickness ratio of 100:1 to form a thickness of The light-emitting layer (EML).
  • EML The light-emitting layer
  • the electron transport layer (ETL), Yb 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 a vapor deposition rate of 1:9, and then vacuum-evaporated on the electron injection layer to form a thickness of The cathode.
  • the vapor deposition thickness on the above cathode is CP-1 to form an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • the main material structure used is shown in Table 8.
  • the organic electroluminescence device was fabricated in the same manner as in Example 45 except that the compounds shown in Table 9 below were used in place of Compound 51 when forming the electron blocking layer.
  • An organic electroluminescence device was produced by the same method as in Example 45 except that Compound E, Compound F, and Compound G shown in Table 8 below were used to replace Compound 51 when forming the electron blocking layer.
  • the nitrogen-containing compound of the present application acts as an electron blocking layer, so that the organic electroluminescent device can further improve the efficiency and lifetime of the device while ensuring a lower driving voltage.

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Abstract

本申请属于有机材料技术领域，提供了一种含氮化合物、电子元件和电子装置。该含氮化合物的结构如化学式1所示，其中，L为包含取代或未取代的金刚烷螺接的芴环的基团；该含氮化合物能够改善电子元件的性能。

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KR1020130106255A、KR1020180137315A、CN108137500A等申请了可以在有机电致发光器件中制备空穴传输层的材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
所述背景技术部分申请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、有机电致发光器件和电子装置，以改善有机电致发光器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 PCTCN2020138112-appb-000001
其中，L为包含取代或未取代的金刚烷螺接芴环的基团；
Ar 1和Ar 2相同或不同，分别独立地选自碳原子数为6-40的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、氚、卤素基团、氰基、碳 原子数为1-10烷基、碳原子数为3-10环烷基、碳原子数为6-20芳基、碳原子数为3-20杂芳基、碳原子数为1-10烷氧基、碳原子数为1-10烷硫基、碳原子数为6-18芳氧基、碳原子数为6-18芳硫基、碳原子数为6-18芳基甲硅烷基、碳原子数为6-18烷基甲硅烷基。
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。
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。
本申请将咔唑和三芳胺基通过带有金刚烷螺接的芴环连接，其中金刚烷螺接的芴环具有富电子特征，将其和三芳基胺组合时将使材料具有高的空穴迁移率；该基团同时具有强的刚性，将其和咔唑基团连接时，可以有效提升材料第一三重态能量，因此，将该材料作为有机电致发光器件的电子阻挡层时，可以在保证空穴向发光层注入效率的同时阻挡激子的流出，提升器件的发光效率和寿命。
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光电转化器件的结构示意图。
图3是本申请一实施方式的电子装置的结构示意图。
图4是本申请另一实施方式的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。
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 PCTCN2020138112-appb-000002
其中，L为包含取代或未取代的金刚烷螺接的芴环的基团；
Ar 1和Ar 2相同或不同，分别独立地选自碳原子数为6-40的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、氚、卤素基团、氰基、碳原子数为1-10烷基、碳原子数为3-10环烷基、碳原子数为6-20芳基、碳原子数为3-20杂芳基、碳原子数为1-10烷氧基、碳原子数为1-10烷硫基、碳原子数为6-18芳氧基、碳原子数为6-18芳硫基、碳原子数为6-18芳基甲硅烷基、碳原子数为6-18烷基甲硅烷基。
在本申请中，Ar 1及Ar 2的碳原子数，指的是所有碳原子数。举例而言，若Ar 2选自碳原子数为22的取代的芳基，则芳基及其上的取代基的所有碳原子数目为22；若Ar 1选自碳原子数为20的取代的杂芳基，则杂芳基及其上的取代基的所有碳原子数为20。
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Rs)。例如，“取代或未取代的芳基”是指具有取代基Rs的芳基或者非取代的芳基。其中上述的取代基即Rs例如可以为氘、卤素基团、氰基、杂芳基、芳基、三烷基硅基、烷基、卤代烷基、环烷基、烷氧基等；当同一个原子上连接有两个取代基Rs时，这两个取代基Rs可以独立地存在或者相互连接以与其所共同连接的原子形成环；当官能团上存在两个相邻的取代基Rs时，相邻的两个取代基Rs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，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、O、N、P、Si或S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、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2020138112-appb-000003
基、芴基、9,9-二甲基芴基、9,9-二苯基芴基、螺二芴基等，而不限于此。
在本申请中，取代的芳基，指的是芳基中的一个或者两个以上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、Br、I、氰基、芳基、杂芳基、支链烷基、直链烷基、环烷基、烷氧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。
在本申请中，杂芳基可以是包括B、O、N、P、Si、Se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、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个芳香环体系的杂芳基。
本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基 团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。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，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 PCTCN2020138112-appb-000004
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。
本申请中，不定位连接键是指从环体系中伸出的单键“
Figure PCTCN2020138112-appb-000005
”，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 PCTCN2020138112-appb-000006
再举例而言，如下式(X')中所示地，式(X')所表示的菲基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式。
Figure PCTCN2020138112-appb-000007
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，如下式(Y)中所示地，式(Y)所表示的取代基R'通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式。
Figure PCTCN2020138112-appb-000008
Figure PCTCN2020138112-appb-000009
在本申请中，碳原子数为1-10的烷基可以包括碳原子数为1-10的直链烷基和碳原子数为3-10的支链烷基。碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1-10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
在本申请中，卤素基团可以包括氟、溴、氯、碘等。
在本申请中，作为取代基的芳基的碳原子数为6-20，该芳基的碳原子数例如可以为6、10、12、14、15、18、20等。作为取代基的芳基的具体实例包括但不限于，苯基、萘基、联苯基、蒽基、菲基、芴基等。
本申请中，作为取代基的杂芳基的碳原子数为3-20，该杂芳基的碳原子数例如可以为3、4、5、7、8、9、12、18、20等。作为取代基的杂芳基的具体实例包括但不限于，吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基等。
在本申请中，术语“烷基甲硅烷基”是指通过一个或两个以上烷基取代的甲硅烷所形成的基团，例如可以为通过一个烷基(R)取代甲硅烷所形成的基团(
Figure PCTCN2020138112-appb-000010
)，可以为通过两个烷基(R)取代甲硅烷所形成的基团(
Figure PCTCN2020138112-appb-000011
)，还可以为三个烷基(R)取代甲硅烷所形成的基团(
Figure PCTCN2020138112-appb-000012
即三烷基硅基)。在一些优选的实施方式中，烷基甲硅烷基为三烷基硅基。另外，在本申请中的术语“硅烷基”和“烷基甲硅烷基”的意义可以互换。
在本申请中，三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。
在本申请中，碳原子数为3-10的环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基等。
本申请中，“未取代的金刚烷螺接的芴环”为如下所示的结构：
Figure PCTCN2020138112-appb-000013
在本申请中，“L为包含取代或未取代的金刚烷螺接的芴环的基团”指的是作为连接基团的L基团包含取代或未取代的金刚烷螺接的芴环，并且还任选地包含其他基团，所述其他基团例如为取代或未取代的苯环，所述其他基团可以通过单键连接在芴环上。
在一种实施方式中，L可以为取代或未取代的金刚烷螺接的芴环。在另一种实施方式中，L还可以为取代或未取代的金刚烷螺接的芴环与取代或未取代的苯环连接形成的基团；以基团L的结构由未取代的金刚烷螺接的芴环和未取代的苯环组成为例，两者的连接方式可如下所示：
Figure PCTCN2020138112-appb-000014
以上结构式中，两个化学键其中一个与
Figure PCTCN2020138112-appb-000015
连接，另一个与
Figure PCTCN2020138112-appb-000016
连接。
可选地，L选自如下式1-1至1-4所组成的组：
Figure PCTCN2020138112-appb-000017
其中，
Figure PCTCN2020138112-appb-000018
表示化学键；
**表示上述取代基用于与
Figure PCTCN2020138112-appb-000019
基团连接；*表示上述取代基用于与
Figure PCTCN2020138112-appb-000020
基团连接。
R 1至R 11相同或不同，且分别独立地选自氘、氚、卤素基团、氰基、碳原子数为1-10烷基、碳原子数为3-10的硅烷基、碳原子数为3-10的环烷基、碳原子数为6-20芳基、碳原子数为3-20的杂芳基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基；
R 1至R 11以R m表示，n 1至n 11以n m表示，n m表示R m的个数，其中的m表示变量并选自1～11的任意整数；举例来讲，当m＝1时，R m是指R 1，n m是指n 1。
具体地，n 1、n 2、n 3、n 4、n 5、n 6、n 8、n 11相同或不同，各自独立地选自0、1、2或3；n 7、n 9、n 10选自0、1、2、3或4；当n m大于1时，任意两者R m相同或不同。
可选地，所述R 1至R 11相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为3-10的硅烷基、碳原子数为5-10的环烷基、碳原子数为6-15的芳基、碳原子数为5-15的杂芳基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基。
可选地，R 1至R 11相同或不同，且分别独立地选自氘、氚、氟、氰基、碳原子数为1-4的烷基、碳原子数为3-7的三烷基硅基、碳原子数为5-10的环烷基、碳原子数为6-12的芳基、碳原子数为5-10的杂芳基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基。
可选地，R 1至R 11分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三甲基硅基、环戊基、环己基、苯基、萘基、吡啶基、甲氧基、乙氧基、甲硫基、乙硫基。
在一种实施方式中，n 1～n 11各自独立地选自0、1或2。
可选地，所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、卤素基团、氰基、碳原子数为1-7的烷基、碳原子数为5-10的环烷基、碳原子数为6-20的芳基、碳原子数为5-20的杂芳基、碳原子数为1-7的烷氧基、碳原子数为1-7的烷硫基、碳原子数为6-10的芳氧基、碳原子数为6-10的芳硫基。
还可选地，所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为6-15的芳基(例如碳原子数为6-12的芳基、碳原子数为15的芳基)、碳原子数为5-12的杂芳基、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、三苯基硅基。
可选地，所述Ar 1、Ar 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三甲基硅基、环戊基、环己基、苯基、萘基、菲基、9,9-二甲基芴基、二吡啶基、甲氧基、乙氧基、甲硫基、乙硫基、三甲基硅基、三苯基硅基、二苯并呋喃基、二苯并噻吩基等。
可选地，L中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三甲基硅基、环戊基、环己基、苯基、萘基、吡啶基、甲氧基、乙氧基、甲硫基、乙硫基等。
可选地，所述Ar 1和Ar 2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-25的取代或未取代的杂芳基。例如，Ar 1和Ar 2各自独立地选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30的取代或未取代的芳基，或者选自碳原子数3、4、5、6、7、8、9、12、16、18、20、21、22、23、24、25的取代或未取代的杂芳基。
在一些实施方式中，所述Ar 1和Ar 2分别独立地选自如下如下化学式i-1至化学式i-15所示基团组成的组：
Figure PCTCN2020138112-appb-000021
Figure PCTCN2020138112-appb-000022
其中，M 1选自单键或者
Figure PCTCN2020138112-appb-000023
G 1～G 5各自独立地选自N或者C(F 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(F 1)时，任意两个F 1相同或者不相同；
G 6～G 13各自独立地选自N或者C(F 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(F 2)时，任意两个F 2相同或者不相同；
G 14～G 23各自独立地选自N或者C(F 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(F 3)时，任意两个F 3相同或者不相同；
G 24～G 33各自独立地选自N或者C(F 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(F 4)时，任意两个F 4相同或者不相同；
H 1选自氢、氘、氟、氯、溴、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；
H 2～H 9、H 21各自独立地选自：氢、氘、氟、氯、溴、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3～18的杂芳基；
H 10～H 20、F 1～F 4各自独立地选自：氢、氘、氟、氯、溴、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6～18的芳基、碳原子数为3～18的杂芳基；
H 1～H 21以H k表示，h 1～h 21以h k表示，其中的k表示变量并选自1～21的任意整数，h k表示取代基H 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选自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；当h k大于1时，任意两个H k相同或者不相同；
K 1选自O、S、Se、N(H 22)、C(H 23H 24)、Si(H 23H 24)；其中，H 22、H 23、H 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的烷基或碳原子数为3～10的 环烷基，或者上述H 23和H 24相互连接以与它们共同连接的原子形成环；
K 2选自单键、O、S、Se、N(H 25)、C(H 26H 27)、Si(H 26H 27)；其中，H 25、H 26、H 27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的烷基或碳原子数为3～10的环烷基，或者上述H 26和H 27相互连接以与它们共同连接的原子形成环。
化学式i-12至化学式i-15中，F 1至F 4可以以F f表示，其中的f为变量，表示1、2、3或4。举例来讲，当f为2时，F f是指F 2。应当理解地是，当不定位连接键连接到C(F f)上时，C(F f)中的F f不存在。例如，在化学式i-13中，当“
Figure PCTCN2020138112-appb-000024
”连接到G 12时，G 12只能表示C原子，即化学式i-13的结构具体为：
Figure PCTCN2020138112-appb-000025
在本申请中，上述H 23与H 24、上述H 26与H 27两组中，每组中的两个基团相互连接所形成的环可以是碳原子数为3～15的饱和或不饱和的环。举例来讲，化学式i-10中，当K 2和M 1均为单键，H 19为氢，且K 1为C(H 23H 24)时，H 23与H 24相互连接以与它们共同连接的原子形成5元环时，化学式i-10即为
Figure PCTCN2020138112-appb-000026
同样地，化学式i-10也可以代表
Figure PCTCN2020138112-appb-000027
即H 23与H 24相互连接以与它们共同连接的原子形成部分不饱和的13元环。
可选地，所述Ar 1和Ar 2分别独立地选自取代或者未取代的基团Z；其中，未取代的基团Z选自如下基团所组成的组：
Figure PCTCN2020138112-appb-000028
取代的基团Z中具有一个或者两个以上取代基，且取代基独立地选自氘、氰基、氟、碳原子数为1-4的烷基、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、吡啶基、苯基、萘基、三苯基硅基；当取代基的数量为两个以上时，任意两个取代基相同或者不相同。
可选地，取代的基团Z中，取代基独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、甲氧基、乙氧基、甲硫基、乙硫基、环戊基、环己基、三甲基硅基、三苯基硅基、吡啶基、苯基、萘基。
可选地，所述Ar 1和Ar 2分别独立地选自下基团所组成的组：
Figure PCTCN2020138112-appb-000029
Figure PCTCN2020138112-appb-000030
进一步可选地，所述Ar 1和Ar 2分别独立地选自下基团所组成的组：
Figure PCTCN2020138112-appb-000031
Figure PCTCN2020138112-appb-000032
可选地，所述含氮化合物的结构可以选自以下结式A至式D所组成的组：
Figure PCTCN2020138112-appb-000033
可选地，所述含氮化合物选自如下化合物所组成的组：
Figure PCTCN2020138112-appb-000034
Figure PCTCN2020138112-appb-000035
Figure PCTCN2020138112-appb-000036
Figure PCTCN2020138112-appb-000037
Figure PCTCN2020138112-appb-000038
Figure PCTCN2020138112-appb-000039
Figure PCTCN2020138112-appb-000040
Figure PCTCN2020138112-appb-000041
Figure PCTCN2020138112-appb-000042
Figure PCTCN2020138112-appb-000043
Figure PCTCN2020138112-appb-000044
Figure PCTCN2020138112-appb-000045
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；其中，所述功能层包含本申请的含氮化合物。
按照一种实施方式，所述电子元件为有机电致发光器件。如图1所示，所述有机电致发光器件包括相对设置的阳极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。
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有机电致发光器件的电子阻挡层322，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的电子可以在发光层复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物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或α,β-ADN。
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(piq) 2(acac)或BD-1(结构如下文所示)。
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、噁二唑衍生物、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350可以由TPBi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。优选包括包含银和镁的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由HAT-CN组成或由F4-TCNQ组成。
可选地，如图1所示，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，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可以由Yb组成。
可选地，在有机电致发光层330和电子传输层350之间还可以设置有空穴阻挡层340。
可选地，所述有机电致发光器件为红光器件或蓝光器件。
按照另一种实施方式，所述电子元件为光电转化器件，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。 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，如图2所示，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，该电子装置包括本申请第二方面所述的电子元件。
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。
下面结合合成例和实施例来说明本申请的含氮化合物及其应用。除非另有说明，所采用的原料、材料均可通过商购获得，或者本领域熟知的方法获得。
化合物合成
化合物51的合成：
(1)
Figure PCTCN2020138112-appb-000046
将2-溴-4-氯-1-碘苯(210.09g,662mmol)、对氯苯硼酸(113.87g,728.2mmol)、四(三苯基膦钯)(3.82g,3.31mmol)、碳酸钾(182.71g,1324mmol)、四丁基氯化铵(3.68g,13.24mmol)、甲苯(1050mL)、乙醇(630mL)和去离子水(420mL)加入圆底烧瓶中，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(1100mL)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-A1-1(80g，收率40％)。
(2)
Figure PCTCN2020138112-appb-000047
将中间体I-A1-1(75.5g,250mmol)和THF(453mL)置于氮气保护下干燥的圆底烧瓶中，在-80℃至-90℃下溶解至澄清后，缓慢滴加n-BuLi(110mL,275mmol)的正己烷溶液至反应体系中，在-80℃至-90℃下反应1h，然后将金刚烷酮(37.56g,250mmol)用THF(150mL)溶解后逐滴缓慢滴加至反应体系中，在-80℃至-90℃下反应1h后自然升至室温，搅拌6小时；向反应液加入5wt％盐酸至pH<7,充分搅拌后，加入二氯甲烷(DCM)进行萃取，合并有机相，水洗至中性，用无水硫酸镁进行干燥，过滤后减压除去溶剂，将所得油状物，加入至有正庚烷的烧瓶内，加热回流至澄清溶液，置于-20℃下重结晶，得到白色中间体l-A1-2(61g，收率65.3％)。
(3)
Figure PCTCN2020138112-appb-000048
将中间体I-A1-2(60g,160.7mmol)、三氟乙酸(54.97g,482.1mmol)和二氯甲烷(480mL)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)进行硅胶柱色谱提纯，得到白色固体状中间体I-A1-3(55.2g，收率96.6％)。
(4)
Figure PCTCN2020138112-appb-000049
将中间体I-A1-3(10g,28.15mmol)、咔唑(4.71g,28.15mmol)、三(二亚苄基丙酮)二钯(0.26g,0.28mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.23g,0.56mmol)以及叔丁醇钠(4.06g,42.23mmol)加入甲苯(100mL)中，氮气保护下加热至108℃，搅拌3h；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，得到中间体1-A1(6g，收率43.8％)。
(5)
Figure PCTCN2020138112-appb-000050
将4-溴联苯(5.0g,21.0mmol)、4-氨基联苯(3.63g,21.45mmol)、三(二亚苄基丙酮)二钯(0.20g,0.21mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.20g,0.42mmol)以及叔丁醇钠(3.09g,32.18mmol)加入甲苯(80mL)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-A1(5.61g，收率81.5％)。
(6)
Figure PCTCN2020138112-appb-000051
将中间体I-A1(5g,10.28mmol)、中间体Ⅱ-A1(3.31g,10.28mmol)、三(二亚苄基丙酮)二钯(0.10g,0.11mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.10g,0.22mmol)以及叔丁醇钠(1.48g,15.42mmol)加入甲苯(50mL)中，氮气保护下加热至108℃，搅拌3h；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51(5.1g，收率64.3％)；质谱：m/z＝771.4[M+H] +。化合物51的核磁： 1H NMR(400MHz,CD 2Cl 2)：8.24(d,2H),8.06(d,2H),7.86-7.78(m,10H),7.75-7.66(m,6H),7.59-7.52(m,4H),7.24(d,3H),6.49-6.44(m,5H),2.91(d,2H),2.61(d,2H),2.16(s,1H),1.90(s,3H),1.77(d,2H),1.69(d,2H),1.60(s,2H)。
化合物52-60的合成
1)制备中间体
按照化合物51的步骤(5)制备表1中的中间体，不同的是，以原料1代替4-溴联苯，原料2代替4-氨基联苯。所合成的中间体结构如表1所示。
2)合成化合物
按照与化合物51相同的合成方法制备化合物，不同的是，步骤(6)中，以表1中的中间体分别代替中间体II-A1。所采用的原料及相应合成的化合物、最后一步的产率、化合物质谱表征结如表1所示。
表1
Figure PCTCN2020138112-appb-000052
Figure PCTCN2020138112-appb-000053
化合物123的合成：
(1)
Figure PCTCN2020138112-appb-000054
将中间体I-A(24.3g,50mmol)、对氯苯硼酸(8.60g,55mmol)、四(三苯基膦)钯(0.58g,0.5mmol)、碳酸钾(13.8g,100mmol)、四丁基氯化铵(0.28g,1mmol)、甲苯(120mL)、乙醇(72mL)和去离子水(48mL)加入圆底烧瓶中，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(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III-A(21.2g，收率75.4％)。
(2)
Figure PCTCN2020138112-appb-000055
将溴苯(10.0g,63.7mmol)、4-氨基联苯(7.07g,41.8mmol)、三(二亚苄基丙酮)二钯(0.35g,0.38mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.36g,0.76mmol)以及叔丁醇钠(5.48g,57.0mmol)加入甲苯(80mL)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IV-A(8.8g，收率86％)。
(3)
Figure PCTCN2020138112-appb-000056
将中间体III-A(5.62g,10.0mmol)、中间体IV-A1(2.45g,10.0mmol)、三(二亚苄基丙酮)二钯(0.183g,0.2mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.16g,0.4mmol)以及叔丁醇钠(1.44g,15mmol)加入甲苯(60mL)中，氮气保护下加热至108℃，搅拌3h；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123(4.8g，收率62.0％)。质谱：m/z＝771.4[M+H] +。
化合物121-130的合成：
1)制备中间体
按照化合物123的步骤(2)制备表2中的中间体，不同的是，以原料3代替溴苯，原料4代替4-氨基联苯。所合成的中间体结构如表2所示。
2)制备化合物
按照与化合物123相同的合成方法制备化合物，不同的是，以表2中的的中间体分别代替中间体IV-A1。所采用的原料及相应合成的化合物、最后一步的产率、化合物质谱表征结如表2所示。
表2化合物结构、制备及表征
Figure PCTCN2020138112-appb-000057
Figure PCTCN2020138112-appb-000058
化合物141的合成：
(1)
Figure PCTCN2020138112-appb-000059
将2′-溴-4-氯联苯(142g,530mmol)和THF(852mL)置于氮气保护下干燥的圆底烧瓶中，在-80℃至-90℃下溶解至澄清后，缓慢滴加n-BuLi的正己烷溶液(254.75mL，2.5M)至反应体系中，在-80℃至-90℃下反应1h，然后将金刚烷酮(63.78g,424.5mmol)用THF(260mL)溶解后逐滴缓慢滴加至反应体系中，在-80℃至-90℃下反应1h后自然升至室温，搅拌6小时；向反应液加入5wt％盐酸至pH<7,充分搅拌后，加入DCM进行萃取，合并有机相，水洗至中性，用无水硫酸镁进行干燥，过滤后减压除去溶剂，将所得油状物，加入至有正庚烷的烧瓶内，加热回流至澄清溶液，置于-20℃下重结晶，得到白色中间体V-A-1(122g，收率84.7％)。
(2)
Figure PCTCN2020138112-appb-000060
将中间体V-A-1(43g,126.9mmol)、三氟乙酸(36.93g,380.6mmol)和二氯甲烷(300mL)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)进行硅胶柱色谱提纯，得到白色固体状中间体V-A-2(39.2g，收率96.3％)。
(3)
Figure PCTCN2020138112-appb-000061
将中间体V-A-2(32.1g,100mmol)、联硼酸频那醇酯(30.47g,120mmol)、三(二亚苄基丙酮)二钯(0.92g,1mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.48g,1mmol)、醋酸钾(29.4g,300mmol)和1,4-二氧六环(320mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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，得到固体中间体V-A-3(33g，收率80％)。
(4)
Figure PCTCN2020138112-appb-000062
将中间体V-A-3(20.6g,50mmol)、1-溴-3-氯-5-碘苯(15.87g,50mmol)、醋酸钯(0.11g,0.5mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.48g,1mmol)、碳酸钾(13.8g,100mmol)、甲苯(100mL)、无水乙醇(60mL)和去离子水(40mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌4h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到固体中间体V-A-4(12g，收率50％)。
(5)
Figure PCTCN2020138112-appb-000063
将中间体V-A-4(11.9g,25mmol)，咔唑(4.18g,25mmol)，三(二亚苄基丙酮)二钯(0.23g,0.25mmol)，2-二环己基磷-2’,6’-二甲氧基联苯(0.21g,0.5mmol)以及叔丁醇钠(3.61g,37.5mmol)加入甲苯(120mL)中，氮气保护下加热至108℃，搅拌3h；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，得到白色固体中间体V-A(7.2g，收率51.4％)。
(6)
Figure PCTCN2020138112-appb-000064
将中间体V-A(5.62g,10mmol)、中间体II-A1(3.21g,10mmol)、三(二亚苄基丙酮)二钯(0.18g,0.2mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.16g,0.4mmol)以及叔丁醇钠(1.44g,15mmol)加入甲苯(60mL)中，氮气保护下加热至108℃，搅拌3h；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141(5.35g，收率63.1％)；质谱：m/z＝847.4[M+H] +。化合物141核磁： 1H NMR(400MHz,CD 2Cl 2)：8.19(d,2H),7.96-7.90(m,2H),7.80(s,1H),7.76-7.69(m,10H),7.66(d,4H),7.62-7.54(m,5H),7.49-7.38(m,6H),6.90(d,4H),6.82(s,1H),6.70(s,1H),2.91(d,2H),2.61(d,2H),2.16(s,1H),1.90(s,3H),1.77(d,2H).1.69(d,2H),1.60(s,2H)。
化合物142-150的合成：
1)制备中间体
按照化合物51的步骤(5)制备表3中的中间体，不同的是，以原料5代替4-溴联苯，原料6代替4-氨基联苯。所合成的中间体结构如表3所示。
2)制备化合物
按照化合物141的合成方法制备化合物，不同的是，步骤(6)中，以表3中的中间体分别代替中间体II-A1。所采用的原料及相应合成的化合物、最后一步的产率、化合物质谱表征结如表3所示。
表3
Figure PCTCN2020138112-appb-000065
Figure PCTCN2020138112-appb-000066
按照以上中间体以及化合物的合成还可以制备以下中间体及化合物：
(1)中间体的制备
a、中间体I-AI的制备：
按照中间体1-A1的方法(化合物51的步骤(1)至步骤(4))制备下列中间体，不同的是，使用原料7代替2-溴-4-氯-1-碘苯，使用原料8代替对氯苯硼酸。所制备的中间体及四步的总收率如4所示。
表4原料及中间体
Figure PCTCN2020138112-appb-000067
b、中间体II-AI的制备：按照中间体II-A1的方法(化合物51的步骤(5))制备下列中间体，在以下中间体II-AI中，不同在于，使用原料9代替4-溴联苯、使用原料10代替4-氨基联苯，所制备的中间体及收率如5所示。
表5原料及中间体
Figure PCTCN2020138112-appb-000068
Figure PCTCN2020138112-appb-000069
Figure PCTCN2020138112-appb-000070
(2)化合物的合成
在以下的实施例中，除了调整中间体I-AI和中间体II-AI，参照化合物51的合成方法制备表6中的化合物，所采用的中间体以及相应合成的化合物、化合物的产率和质谱表征如表6所示。
表6
Figure PCTCN2020138112-appb-000071
Figure PCTCN2020138112-appb-000072
Figure PCTCN2020138112-appb-000073
化合物304的合成：
(1)
Figure PCTCN2020138112-appb-000074
将中间体I-A1-3(10g,28.15mmol)、联硼酸频那醇酯(9.30g,36.59mmol)、三(二亚苄基丙酮)二钯(0.26g,0.28mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.27g,0.56mmol)、醋酸钾(5.52g,56.29mmol)和1,4-二氧六环(100mL)加入三口圆底烧瓶中，氮气保护下加热至80℃，搅拌3h；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，得到固体中间体VI-1(8.4g，收率66.8％)。
(2)
Figure PCTCN2020138112-appb-000075
将中间体VI-1(8g,17.9mmol)、9-(4-溴苯基)咔唑(5.77g,17.9mmol)、醋酸钯(0.04g, 0.179mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.17g,0.358mmol)、碳酸钾(4.94g,35.8mmol)、甲苯(50mL)、无水乙醇(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4h；而后冷却至室温，反应液使用水洗后加入硫酸镁干燥，过滤后将滤液减压除去溶剂；使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯，得到固体中间体VI-2(6.5g，收率65％)。
(3)
Figure PCTCN2020138112-appb-000076
将2-溴萘(10.0g,48.29mmol)、3-氨基联苯(8.17g,48.29mmol)、三(二亚苄基丙酮)二钯(0.44g,0.48mmol)、2-二环己基磷-2’,4’,6’-三异丙基联苯(0.43g,0.96mmol)以及叔丁醇钠(6.96g,72.44mmol)加入甲苯(100mL)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IV-A(12.26g，收率86％)。
(4)
Figure PCTCN2020138112-appb-000077
将中间体VI-2(6.5g,11.56mmol)、中间体VI-3(3.41g,11.56mmol)、三(二亚苄基丙酮)二钯(0.11g,0.116mmol)、2-二环己基磷-2’,6’-二甲氧基联苯(0.09g,0.23mmol)以及叔丁醇钠(1.66g,17.34mmol)加入甲苯(65mL)中，氮气保护下加热至108℃，搅拌3h；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304(5.85g，收率61.6％)。质谱：m/z＝821.4[M+H] +。
有机电致发光器件制备及评估
实施例1
通过以下过程制备有机电致发光器件：将ITO厚度为
Figure PCTCN2020138112-appb-000078
的基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀化合物HAT-CN以形成厚度为
Figure PCTCN2020138112-appb-000079
的空穴注入层(HIL)；
在空穴注入层上真空蒸镀化合物NPB，以形成厚度为
Figure PCTCN2020138112-appb-000080
的空穴传输层(HTL)。
在空穴传输层上蒸镀化合物51作为电子阻挡层(EBL)，厚度为
Figure PCTCN2020138112-appb-000081
。
在电子阻挡层上蒸镀以化合物CBP作为主体，掺杂膜厚比为3％的Ir(piq) 2(acac)，形成厚度为
Figure PCTCN2020138112-appb-000082
的有机发光层(EML)。
在有机发光层上按蒸镀比例为1∶1的膜厚比掺杂TPBi和LiQ作为电子传输层(ETL)，厚度为
Figure PCTCN2020138112-appb-000083
。在电子传输层上蒸镀Yb以形成厚度为
Figure PCTCN2020138112-appb-000084
的电子注入层(EIL)。
然后，在电子注入层将镁(Mg)和银(Ag)以1∶9膜厚比真空蒸镀在电子注入层上，形成厚度为
Figure PCTCN2020138112-appb-000085
的阴极。在阴极上蒸镀化合物CP-1，作为有机覆盖层(CPL)，厚度为
Figure PCTCN2020138112-appb-000086
将蒸镀完成的器件在氮气手套箱(水、氧的含量需严格控制)中用紫外线硬化树脂封装，以免器件被外界的水分或其他物质腐蚀。
其中，在制备有机电致发光器件时，所使用的各个材料的结构如下：
Figure PCTCN2020138112-appb-000087
实施例2-44
上述器件结构中，除了把电子阻挡层(EBL)的化合物51替代为表7所列举的化合物外，其他与实施例1相同，采用相同的制备工艺进行有机电致发光器件的制备。
对比例1-4
分别利用化合物A、B、C、D替代化合物51，其他与实施例1相同，按照相同的方法，制备相应的有机电致发光器件。化合物A、B、C和D的结构如下：
Figure PCTCN2020138112-appb-000088
对以上实施例和对比例制备的有机电致发光器件在10mA/cm 2的条件下分析了器件的光电性能，并在15mA/cm 2的条件下分析其T95寿命，结果如表7所示。
表7有机电致发光器件及测试结果
Figure PCTCN2020138112-appb-000089
Figure PCTCN2020138112-appb-000090
由表7可知，在化合物作为电子阻挡层应用于红光有机电致发光器件，实施例1-44与对比例1至3的器件的性能相比，外量子效率最少提高了14％，电流效率最小提高22％，T95寿命至少提高了42.5％。实施例1-44与对比例4的器件的性能相比，在寿命上最少提高了11.3％，电流效率至少提高了9.3％。并且，与对比例1-4相比，实施例1-44的器件也兼具较低的驱动电压。
实施例45
通过以下过程制备阳极：将厚度为
Figure PCTCN2020138112-appb-000091
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，形成厚度为
Figure PCTCN2020138112-appb-000092
的空穴注入层(HIL)，并且在空穴注入层上蒸镀NPB，形成厚度为
Figure PCTCN2020138112-appb-000093
的空穴传输层。
在空穴传输层上真空蒸镀化合物51，形成厚度为
Figure PCTCN2020138112-appb-000094
的电子阻挡层(EBL)。
在电子阻挡层上，将α,β-ADN作为主体，按照膜厚比100:1同时掺杂BD-1，形成厚度为
Figure PCTCN2020138112-appb-000095
的发光层(EML)。
将TPBi和LiQ以1∶1的膜厚比进行共蒸镀形成
Figure PCTCN2020138112-appb-000096
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 PCTCN2020138112-appb-000097
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 PCTCN2020138112-appb-000098
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2020138112-appb-000099
的CP-1，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。所采用的主要材料结构如表8所示。
实施例46-实施例84
除了在形成电子阻挡层时，以下表9中所示的化合物替代化合物51以外，利用与实施例45相同的方法制作有机电致发光器件。
比较例5-7
除了在形成电子阻挡层时，分别以下表8中所示的化合物E、化合物F和化合物G替代化合物51以外，利用与实施例45相同的方法制作有机电致发光器件。
以上实施例和对比例使用的材料结构如下表8所示：
表8
Figure PCTCN2020138112-appb-000100
对如上制得的有机电致发光器件，除寿命T95外，在20mA/cm 2的条件下分析了器件的性能，其结果示于下表9。
表9有机电致发光器件及测试结果
Figure PCTCN2020138112-appb-000101
Figure PCTCN2020138112-appb-000102
由表8可知，在化合物作为电子阻挡层应用于蓝光有机电致发光器件，实施例45-84与对比例5-7的器件的性能相比，外量子效率最少提高了10.6％，T95寿命至少提高了23.1％，同时也兼具较低的驱动电压。
综上可知，本申请的含氮化合物作为电子阻挡层，使有机电致发光器件在保证较低驱动电压的同时，能进一步改善器件的效率和寿命。

Claims (15)

  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 PCTCN2020138112-appb-100001
    其中，L为包含取代或未取代的金刚烷螺接的芴环的基团；
    Ar 1和Ar 2相同或不同，分别独立地选自碳原子数为6-40的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
    所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、氚、卤素基团、氰基、碳原子数为1-10烷基、碳原子数为3-10环烷基、碳原子数为6-20芳基、碳原子数为3-20杂芳基、碳原子数为1-10烷氧基、碳原子数为1-10烷硫基、碳原子数为6-18芳氧基、碳原子数为6-18芳硫基、碳原子数为6-18芳基甲硅烷基、碳原子数为6-18烷基甲硅烷基。
  2. 根据权利要求1所述的含氮化合物，其特征在于，L选自如下式1-1至1-4所组成的组：
    Figure PCTCN2020138112-appb-100002
    其中，
    Figure PCTCN2020138112-appb-100003
    表示化学键；
    **表示上述取代基用于与
    Figure PCTCN2020138112-appb-100004
    基团连接；
    *表示上述取代基用于与
    Figure PCTCN2020138112-appb-100005
    基团连接；
    R 1至R 11相同或不同，且分别独立地选自氘、氚、卤素基团、氰基、碳原子数为1-10烷基、碳原子数为3-10的硅烷基、碳原子数为3-10的环烷基、碳原子数为6-20芳基、碳原子数为3-20的杂芳基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基；
    R 1至R 11以R m表示，n 1至n 11以n m表示，n m表示R m的个数，其中的m表示变量并选自1～11的任意整数；n 1、n 2、n 3、n 4、n 5、n 6、n 8、n 11相同或不同，各自独立地选自0、1、2或3；n 7、n 9、n 10选自0、1、2、3或4；且当n m大于1时，任意两者R m相同或不同。
  3. 根据权利要求2所述的含氮化合物，其特征在于，所述R 1至R 11相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为3-10的硅烷基、碳原子数为5-10的环烷基、碳原子数为6-15的芳基、碳原子数为5-15的杂芳基、碳原子数为1-4的烷氧基、碳原子数 为1-4的烷硫基。
  4. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、卤素基团、氰基、碳原子数为1-7的烷基、碳原子数为5-10的环烷基、碳原子数为6-20的芳基、碳原子数为5-20的杂芳基、碳原子数为1-7的烷氧基、碳原子数为1-7的烷硫基、碳原子数为6-10的芳氧基、碳原子数为6-10的芳硫基。
  5. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1、Ar 2和L中的取代基相同或不同，且分别独立地选自：氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为5-10的环烷基、碳原子数为6-15的芳基、碳原子数为5-12的杂芳基、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、三苯基硅基。
  6. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1和Ar 2分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-25的取代或未取代的杂芳基。
  7. 根据权利要求1或6所述的含氮化合物，其特征在于，所述Ar 1、Ar 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、正丁基、叔丁基、三甲基硅基、环戊基、环己基、苯基、萘基、菲基、9,9-二甲基芴基、二吡啶基、甲氧基、乙氧基、甲硫基、乙硫基、三甲基硅基、三苯基硅基、二苯并呋喃基或二苯并噻吩基。
  8. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1和Ar 2分别独立地选自如下化学式i-1至化学式i-15所组成的组：
    Figure PCTCN2020138112-appb-100006
    Figure PCTCN2020138112-appb-100007
    其中，M 1选自单键或者
    Figure PCTCN2020138112-appb-100008
    G 1～G 5各自独立地选自N或者C(F 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(F 1)时，任意两个F 1相同或者不相同；
    G 6～G 13各自独立地选自N或者C(F 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(F 2)时，任意两个F 2相同或者不相同；
    G 14～G 23各自独立地选自N或者C(F 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(F 3)时，任意两个F 3相同或者不相同；
    G 24～G 33各自独立地选自N或者C(F 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(F 4)时，任意两个F 4相同或者不相同；
    H 1选自氢、氘、氟、氯、溴、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；
    H 2～H 9、H 21各自独立地选自：氢、氘、氟、氯、溴、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3～18的杂芳基；
    H 10～H 20、F 1～F 4各自独立地选自：氢、氘、氟、氯、溴、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6～18的芳基、碳原子数为3～18的杂芳基；
    H 1～H 21以H k表示，h 1～h 21以h k表示，其中的k表示变量并选自1～21的任意整数，h k表示取代基H 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选自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；当h k大于1时，任意两个H k相同或者不相同；
    K 1选自O、S、Se、N(H 22)、C(H 23H 24)、Si(H 23H 24)；其中，H 22、H 23、H 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的烷基或碳原子数为3～10的环烷基，或者上述H 23和H 24相互连接以与它们共同连接的原子形成环；
    K 2选自单键、O、S、Se、N(H 25)、C(H 26H 27)、Si(H 26H 27)；其中，H 25、H 26、H 27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的烷基或碳原子数为3～10的环烷基，或者上述H 26和H 27相互连接以与它们共同连接的原子形成环。
  9. 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分别独立地选自取代或者未取代的基团Z；其中，未取代的基团Z选自如下基团所组成的组：
    Figure PCTCN2020138112-appb-100009
    取代的基团Z中具有一个或者两个以上取代基，且取代基独立地选自氘、氰基、氟、碳原子数为1-4的烷基、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、吡啶基、苯基、萘基、三甲基硅基、三苯基硅基；当取代基的数量为两个以上时，任意两个取代基相同或者不相同。
  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分别独立地选自以下基团所组成的组：
    Figure PCTCN2020138112-appb-100010
    Figure PCTCN2020138112-appb-100011
  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组成的组：
    Figure PCTCN2020138112-appb-100012
    Figure PCTCN2020138112-appb-100013
    Figure PCTCN2020138112-appb-100014
    Figure PCTCN2020138112-appb-100015
    Figure PCTCN2020138112-appb-100016
    Figure PCTCN2020138112-appb-100017
    Figure PCTCN2020138112-appb-100018
    Figure PCTCN2020138112-appb-100019
    Figure PCTCN2020138112-appb-100020
    Figure PCTCN2020138112-appb-100021
    Figure PCTCN2020138112-appb-100022
    Figure PCTCN2020138112-appb-100023
    Figure PCTCN2020138112-appb-100024
  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；其中，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. 一种电子装置，其特征在于，包括权利要求12-14任一项所述的电子元件。
PCT/CN2020/138112 2019-12-31 2020-12-21 含氮化合物、电子元件和电子装置 WO2021136006A1 (zh)

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