WO2021218491A1 - 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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WO2021218491A1
WO2021218491A1 PCT/CN2021/082174 CN2021082174W WO2021218491A1 WO 2021218491 A1 WO2021218491 A1 WO 2021218491A1 CN 2021082174 W CN2021082174 W CN 2021082174W WO 2021218491 A1 WO2021218491 A1 WO 2021218491A1
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carbon atoms
substituted
groups
unsubstituted
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PCT/CN2021/082174
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English (en)
French (fr)
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杨敏
南朋
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陕西莱特光电材料股份有限公司
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Priority to US17/787,700 priority Critical patent/US11655206B2/en
Priority to KR1020227022015A priority patent/KR102512339B1/ko
Publication of WO2021218491A1 publication Critical patent/WO2021218491A1/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 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 a and R b are each independently selected from hydrogen or the group shown in Chemical Formula 1-1, and only one of Ra and R b is a group shown in Chemical Formula 1-1;
  • L is selected from a single bond, a substituted or unsubstituted arylene group having a total carbon number of 6 to 30, and a substituted or unsubstituted heteroarylene group having a total carbon number of 3 to 30;
  • R 1 is selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group with total carbon atoms of 1-20, substituted or unsubstituted aryl group with total carbon atoms of 6-30, substituted or unsubstituted
  • R 2 is selected from deuterium, cyano, halogen group, substituted or unsubstituted alkyl group with total carbon atoms of 1-20, substituted or unsubstituted aryl group with total carbon atoms of 6-30, substituted or unsubstituted A substituted heteroaryl group with a total carbon number of 3-30, and at least one of R 1 and R 2 is selected from a substituted or unsubstituted aryl group with a total carbon number of 6-30, a substituted or unsubstituted Heteroaryl groups with a total carbon number of 3-30;
  • n 1 is selected from 0, 1, 2, 3 or 4. When n 1 is greater than 1, any two R 1 are the same or different;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted alkyl groups having a total carbon number of 1 to 20, substituted or unsubstituted cycloalkyl groups having a total carbon number of 3 to 20, A substituted or unsubstituted aryl group having a total carbon number of 6 to 30, a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 30, and the Ar 1 is not 9,9-diphenylfluorene Group, the Ar 2 is not 9,9-diphenylfluorenyl;
  • each of L, R 1 , R 2 , Ar 1 and Ar 2 are independently selected from deuterium, halogen groups, cyano groups, and heteroaryl groups having 3 to 20 carbon atoms, optionally 0, 1, 2, 3, 4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, and tert-butyl aryl groups with 6 to 20 carbon atoms, and the number of carbon atoms is 6 to 20 halogenated aryl groups, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, alkyl groups with 1 to 10 carbon atoms, and number of carbon atoms It is a haloalkyl group of 1 to 10, an alkenyl group of 2 to 6 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, and a carbon number of 2 to 10 Hetero
  • the compound provided in this application has good hole transport properties and can be applied between the anode and the energy conversion layer of organic electroluminescent devices and photoelectric conversion devices to improve the hole transport efficiency between the anode and the energy conversion layer. Furthermore, the luminous efficiency of the organic electroluminescence device and the power generation efficiency of the photoelectric conversion device are improved.
  • This application has designed an arylamine group to be introduced into the adamantane spirofluorene group, wherein the adamantane spirofluorene group has aryl or heteroaryl substituents, which can increase the steric hindrance of the compound
  • the effect which can effectively increase the glass transition temperature of the material, and the adamantyl group screwed on the fluorene group has a large space volume and strong rigidity, which makes the structure have higher electronic tolerance and film-forming properties, Therefore, the efficiency and life span of the organic electroluminescence device and the photoelectric conversion device can be improved.
  • the compound of the application has a lower working voltage.
  • this type of compound also has better thermal stability and can maintain a stable structure at high temperatures for a long time. Under the same molecular weight, the evaporation temperature decreases, making the nitrogen-containing compound of this application better when used in mass production.
  • the physical and thermal stability of the organic electroluminescent device is convenient for the mass production stability of the organic electroluminescent device.
  • 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 photoelectric conversion device.
  • an electronic device including the above-mentioned electronic component.
  • 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.
  • Electron transport layer 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.
  • L is selected from a single bond, a substituted or unsubstituted arylene group having a total carbon number of 6 to 30, and a substituted or unsubstituted heteroarylene group having a total carbon number of 3 to 30;
  • R 1 is selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having a total carbon number of 1-10, substituted or unsubstituted aryl group having a total carbon number of 6-30, substituted or unsubstituted The substituted heteroaryl group having a total carbon number of 3-30, and the R 1 is not a carbazolyl group or an N-phenylcarbazolyl group;
  • R 2 is selected from deuterium, cyano, halogen group, substituted or unsubstituted alkyl group with total carbon atoms of 1-20, substituted or unsubstituted aryl group with total carbon atoms of 6-30, substituted or unsubstituted A substituted heteroaryl group with a total carbon number of 3-30, and at least one of R 1 and R 2 is selected from a substituted or unsubstituted aryl group with a total carbon number of 6-30, a substituted or unsubstituted Heteroaryl groups with a total carbon number of 3-30;
  • n 1 and n 2 are the numbers of R 1 and R 2 respectively;
  • n 1 is selected from 0, 1, 2, 3 or 4. When n 1 is greater than 1, any two R 1 are the same or different;
  • Ar 1 and Ar 2 are the same or different, and are each independently selected from substituted or unsubstituted alkyl groups having a total carbon number of 1 to 20, substituted or unsubstituted cycloalkyl groups having a total carbon number of 3 to 20, A substituted or unsubstituted aryl group having a total carbon number of 6 to 30, a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 30, and the Ar 1 is not 9,9-diphenylfluorene Group, the Ar 2 is not 9,9-diphenylfluorenyl;
  • each of L, R 1 , R 2 , Ar 1 and Ar 2 are independently selected from deuterium, halogen groups, cyano groups, and heteroaryl groups having 3 to 20 carbon atoms, optionally 0, 1, 2, 3, 4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, tert-butyl substituted with 6 to 20 aryl groups with carbon atoms 6 to 20 halogenated aryl groups, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, alkyl groups with 1 to 10 carbon atoms, and number of carbon atoms It is a haloalkyl group of 1 to 10, an alkenyl group of 2 to 6 carbon atoms, an alkynyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 10 carbon atoms, and a carbon number of 2 to 10 Heterocycloalkyl, cycl
  • C6-20 is optionally substituted by 0, 1, 2, 3, 4 or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, and tert-butyl
  • Aryl means that the aryl group can be substituted by one or more of deuterium, fluorine, chlorine, cyano, methyl, and tert-butyl, or not by deuterium, fluorine, chlorine, cyano, methyl, tert-butyl.
  • the number of substituents on the aryl group is greater than or equal to 2, the substituents may be the same or different.
  • the substituents in each of L, R 1 , R 2 , Ar 1 and Ar 2 are independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 18 carbon atoms, C6-18 aryl group, C6-20 halogenated aryl group, C3-12 trialkylsilyl group, C18-24 triarylsilyl group , C1-C10 alkyl group, C1-C10 haloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C3-C3 ⁇ 10 cycloalkyl, carbon 2-10 heterocycloalkyl, carbon 5-10 cycloalkenyl, carbon 4-10 heterocycloalkenyl, carbon 1 ⁇ 10 alkoxy, C 1-10 alkylthio, C 6-18 aryloxy, C 6-18 arylthio, C 6-18 ⁇ phosphooxy.
  • adamantane is a three-dimensional structure, in the compound structure diagram, because of different drawing angles, it will show 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 compound provided in this application has good hole transport properties and can be applied between the anode and the energy conversion layer of organic electroluminescent devices and photoelectric conversion devices to improve the hole transport efficiency between the anode and the energy conversion layer. Furthermore, the luminous efficiency of the organic electroluminescence device and the power generation efficiency of the photoelectric conversion device are improved.
  • 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 total number of carbon atoms in the present application L, Ar, Ar 2, R 1, R 2, R a and R b are the substituted or unsubstituted 1, it refers to the number of all carbon atoms.
  • L is selected from a substituted arylene group having a total carbon number of 12, all carbon atoms of the arylene group and the substituents thereon are 12.
  • Ar 1 is Then its total number of carbon atoms is 7; L is The total number of carbon atoms is 12.
  • hetero means that a functional group includes at least one heteroatom such as B, N, O, S, Se, Si, 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.
  • Alkyl groups can have 1 to 20 carbon atoms.
  • a numerical range such as “1 to 20” refers to each integer in the given range; for example, “1 to 20 carbon atoms” means that it can contain 1 Carbon atoms, 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 base.
  • the alkyl group may also be a medium-sized 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 to 6 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and sec-butyl. Group, tert-butyl, pentyl and hexyl.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • the aryl group can be a monocyclic aryl group 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 a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-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, P, and Si.
  • examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl Group, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, Base and so on.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group.
  • a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group.
  • the total number of carbon atoms of the group is 18. That is, in this application, the number of carbon atoms of the aryl group is selected from 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
  • Specific examples include but are not limited to the following structures:
  • Ar 1 is not Ar 2 is not
  • a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof.
  • the heteroatom may be at least one of B, O, N, P, Si, and S.
  • the heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, 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 type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are multiple groups conjugated through carbon-carbon bonds.
  • Heteroaryl group of ring system type is heteroaryl group of ring system type.
  • the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkane Group, cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • heteroaryl groups as substituents include, but are not limited to: dibenzofuranyl, carbazolyl, dibenzothienyl, pyridyl and the like.
  • 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. That is, in this application, the number of carbon atoms of the heteroaryl group is selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 , 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
  • the explanation of the aryl group can be applied to the arylene group, and the explanation of the heteroaryl group can also be applied to the heteroarylene group.
  • the halogen group can be fluorine, chlorine, bromine, or iodine.
  • nitrogen-containing compound of the present application enable it to be used in the preparation of organic electroluminescent devices and photoelectric conversion devices, especially suitable for the preparation of electron blocking layers of organic electroluminescent devices and photoelectric conversion devices (also known as hole-assisted Layer, second hole transport layer, etc.) in order 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 Mass production stability of organic electroluminescent devices.
  • electron blocking layers of organic electroluminescent devices and photoelectric conversion devices also known as hole-assisted Layer, second hole transport layer, etc.
  • L is selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6 to 20, and a substituted or unsubstituted heteroarylene group with a total carbon number of 5 to 20 .
  • L is selected from a single bond, a substituted or unsubstituted arylene group having a total carbon number of 6-15.
  • the substituent in L is selected from deuterium, halogen, cyano, and alkyl having 1 to 5 carbon atoms. Specifically, the substituent in L is selected from deuterium, fluorine, cyano, methyl, ethyl, tert-butyl and the like.
  • L is selected from the group consisting of a single bond or a group represented by chemical formula j-1 to chemical formula j-14:
  • M 2 is selected from a single bond or Represents a chemical bond
  • Q 1 ⁇ Q 5 and Q '1 ⁇ Q' 5 are each independently selected from N or C (J 5), and in Q 1 ⁇ Q 5 is selected from at least one N; when two or more of Q 1 ⁇ Q 5 when selected from C (J 5), any two J 5 same or different, when Q '1 ⁇ Q' is selected from two or more of C (J 5), any two J 5 identical or different ;
  • Q 6 to Q 13 are each independently selected from N, C or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ), any two J 6 are the same or different;
  • Q 24 to Q 33 are each independently selected from N, C or C (J 8 ), and at least one of Q 24 to Q 32 is selected from N; when two or more of Q 24 to Q 32 are selected from C (J 8 ), any two J 8s are the same or different;
  • E 1 ⁇ E 14 , J 5 ⁇ J 9 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, optionally with 0, 1, 2, 3, 4 or 5 substituents selected from the group consisting of deuterium, fluorine, chlorine, cyano, methyl, and tert-butyl aryl groups with 6 to 20 carbon atoms, trioxanes with 3 to 12 carbon atoms Silyl group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, alkenyl group with 2-6 carbon atoms, alkynyl group with 2-6 carbon atoms, carbon atom 3-10 cycloalkyl, carbon 2-10 heterocycloalkyl, carbon 5-10 cycloalkenyl, carbon 4-10 heterocycloalkenyl, carbon atom
  • E r represents any integer of 1 to 14, E r E r represents the number of substituents; when r is selected from 1,2, When 3, 4, 5, 6, 9, 13, or 14, e r is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, e r is selected from 1, 2, 3, 4, 5 or 6; when r is 12, e r is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, e r is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when e r is greater than 1, any two E r are the same or different;
  • K 3 is selected from O, S, Se, N (E 15 ), C (E 16 E 17 ), Si (E 18 E 19 ); wherein, E 15 , E 16 , E 17 , E 18 and E 19 are each independent Is selected from: aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, carbon Alkynyl group with 2-6 atoms, cycloalkyl group with 3-10 carbon atoms, heterocycloalkyl group with 2-10 carbon atoms, cycloalkenyl group with 5-10 carbon atoms, carbon atom number Is a heterocycloalkenyl group of 4 to 10, or E 16 and E 17 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 18 and E 19 are connected to each other to form a saturated or unsaturated ring with carbon atoms
  • K 4 is selected from single bond, O, S, Se, N (E 20 ), C (E 21 E 22 ), Si (E 23 E 24 ); wherein, E 20 to E 24 are each independently selected from: carbon atoms An aryl group having 6 to 20, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and 2 to 6 carbon atoms The alkynyl group, the cycloalkyl group with 3 to 10 carbon atoms, the heterocycloalkyl group with 2 to 10 carbon atoms, the cycloalkenyl group with 5 to 10 carbon atoms, the heterocycloalkenyl group with 4 to 10 carbon atoms Cycloalkenyl, or E 21 and E 22 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 23 and E 24 are connected to each other to form a saturated or unsaturated ring with them
  • L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group .
  • L is selected from the group consisting of a single bond or the following groups:
  • L is selected from the group consisting of a single bond or the following groups:
  • the substituent in L is selected from deuterium, methyl, ethyl, and tert-butyl.
  • R 1 and R 2 are the same or different, and are independently selected from deuterium, cyano, halogen group, substituted or unsubstituted alkyl with a total carbon number of 1 to 6, substituted Or an unsubstituted aryl group having a total carbon number of 6 to 25, a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 25, and the R 1 is not a carbazolyl group or N-phenylcarba Azole.
  • R 1 is selected from deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having a total carbon number of 1 to 6, substituted or unsubstituted aryl group having a total carbon number of 6 to 25 , A substituted or unsubstituted heteroaryl group having a total carbon number of 5-12, and the R 1 is not a carbazolyl group or an N-phenylcarbazolyl group.
  • R 1 is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted Or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted pyridylene, substituted Or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl.
  • R 2 is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted Or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted pyridylene, substituted Or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.
  • the substituents in R 1 and R 2 are the same or different, and are independently selected from the group consisting of deuterium, cyano, halogen group, and the total number of substituted or unsubstituted carbon atoms is 1.
  • the alkyl group of ⁇ 6, the aryl group of 6 to 20 carbon atoms, and the heteroaryl group of 3 to 20 carbon atoms, and the substituent of R 1 is not a carbazolyl group.
  • the substituent in R 1 is selected from the group consisting of deuterium, fluorine, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, and cyano.
  • the substituent in R 2 is selected from: deuterium, fluorine, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, carbazolyl, N-phenylcarbazolyl, cyano base.
  • R 1 is selected from the group consisting of deuterium, halogen group, methyl, ethyl, tert-butyl, or the following groups, but is not limited to this:
  • R 2 is selected from the group consisting of deuterium, halogen group, methyl, ethyl, tert-butyl, or the following groups, but it is not limited to this:
  • R 1 is selected from the group consisting of deuterium, halogen group, methyl, ethyl, tert-butyl, or the following groups:
  • R 2 is selected from the group consisting of deuterium, halogen group, methyl, ethyl, tert-butyl, or the following groups:
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with a total carbon number of 6 to 24, and substituted or unsubstituted total carbon atoms. It is a heteroaryl group of 3-24.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, and 3 to 15 carbon atoms.
  • the substituents in Ar 1 and Ar 2 are the same or different, and are each independently selected from deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclohexane, adamantane Alkyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups having a total carbon number of 6 to 21, substituted or unsubstituted heterocyclic groups having a total carbon number of 12 to 24. Aryl.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the groups represented by the following chemical formula i-1 to chemical formula i-15:
  • M 1 is selected from a single bond or
  • G 1 ⁇ G 5 and G '1 ⁇ G' 4 are each independently selected from N, C, or C (J 1), and in G 1 ⁇ G 5 is selected from at least one N; when the two G 1 ⁇ G 5 When more than one is selected from C(J 1 ), any two J 1 are the same or different;
  • G 6 to G 13 are each independently selected from N, C or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ), any two J 2 are the same or different;
  • G 14 to G 23 are each independently selected from N, C or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ), any two J 3 are the same or different;
  • G 24 to G 33 are each independently selected from N, C or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ), any two J 4 are the same or different;
  • Z 1 is selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and haloalkyl group having 1 to 10 carbon atoms , Cycloalkyl groups with 3-10 carbon atoms, alkoxy groups with 1-10 carbon atoms, alkylthio groups with 1-10 carbon atoms, triarylsilyl groups with 18-24 carbon atoms;
  • Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, C1-C10 haloalkyl group, C3-C10 cycloalkyl group, C1-C10 alkoxy group, C1-C10 alkylthio group, C1-C10 It is an alkylthio group of 1 to 10, a heteroaryl group of 3 to 18 carbon atoms, and a triarylsilyl group of 18 to 24 carbon atoms;
  • Z 10 to Z 20 and J 1 to J 4 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, and one having 1 to 10 carbon atoms Alkyl group, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, alkoxy group having 1-10 carbon atoms, alkylthio group having 1-10 carbon atoms, Optionally substituted with 0, 1, 2, 3, 4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, tert-butyl, and having 6 to 18 carbon atoms Aryl group, heteroaryl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms;
  • h 1 ⁇ h 21 are represented by h k
  • Z 1 ⁇ Z 21 are represented by Z k
  • k is a variable, representing any integer from 1 to 21
  • h k is the number of substituents Z k ; wherein, when k is selected from 5 Or when 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected When 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 Or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
  • K 1 is selected from O, S, N (Z 22 ), C (Z 23 Z 24 ), Si (Z 28 Z 29 ); wherein, Z 22 , Z 23 , Z 24 , Z 28 , and Z 29 are each independently selected From: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or the above Z 23 and Z 24 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms with the atoms connected to them, or the above-mentioned Z 28 and Z 29 are connected to each other to form a carbon atom number with their commonly connected atoms A saturated or unsaturated ring of 3-15;
  • K 2 is selected from a single bond, O, S, N (Z 25 ), C (Z 26 Z 27 ), Si (Z 30 Z 31 ); wherein, Z 25 , Z 26 , Z 27 , Z 30 , and Z 31 are each Independently selected from: aryl groups having 6 to 18 carbon atoms, heteroaryl groups having 3 to 18 carbon atoms, alkyl groups having 1 to 10 carbon atoms, or cycloalkyl groups having 3 to 10 carbon atoms , Or the above-mentioned Z 26 and Z 27 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or the above-mentioned Z 30 and Z 31 are connected to each other to form a shared atom with them A saturated or unsaturated ring having 3 to 15 carbon atoms.
  • Ar 1 and Ar 2 are respectively selected from the groups represented by the following chemical formula i-16:
  • Z 32 and Z 33 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, and the number of carbon atoms Is a haloalkyl group having 1-10, a cycloalkyl group having 3-10 carbon atoms, an alkoxy group having 1-10 carbon atoms, an alkylthio group having 1-10 carbon atoms, optionally substituted by 0, 1, 2, 3, 4, or 5 substituents selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, and tert-butyl aryl groups with 6 to 18 carbon atoms, and the number of carbon atoms Heteroaryl groups of 3-18, triarylsilyl groups of 18-24 carbon atoms;
  • h 32 is the number of Z 32
  • h 33 is the number of Z 33
  • h 32 is selected from 0, 1, 2 or 3, when h 32 is greater than 1, any two Z 32 are the same or different;
  • h 33 is selected from 0, 1, 2, 3, 4 or 5. When h 33 is greater than 1, any two Z 33 are the same or different.
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of the following groups, but are not limited to this:
  • Ar 1 and Ar 2 are the same or different, and are independently selected from the group consisting of the following groups, but not limited to:
  • the nitrogen-containing compound is selected from the group consisting of, but not limited to:
  • This application also provides an electronic component for realizing photoelectric conversion or electro-optical conversion.
  • the electronic component includes an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer includes the nitrogen-containing compound of the present application.
  • 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 organic electroluminescence device is a green organic electroluminescence device or a blue organic electroluminescence device.
  • 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 or a hole injection layer 310.
  • the hole transport layer 321 or the hole injection layer 310 may contain the nitrogen-containing compound provided in the present application to improve the hole density of the electronic device. Transmission capacity.
  • 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. 350 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, 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 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.
  • a transparent electrode containing indium tin oxide (ITO) as an anode is preferable.
  • 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 electroluminescent layer 330 may be composed of a single luminescent material, or may include a host material and a guest material.
  • the organic electroluminescent layer 330 is composed of a host material and a guest material. The holes injected into the organic electroluminescent layer 330 and the electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form an excitation. The exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
  • the host material of the organic electroluminescent layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and this application does not make any special considerations for this. limit.
  • the host material of the organic electroluminescent layer 330 may be a combination of GH-n1 and GH-n2 or ⁇ , ⁇ -ADN.
  • the guest material of the organic electroluminescent layer 330 may be a compound with a condensed aryl ring or a derivative thereof, a compound with a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials, which are not described in this application. Special restrictions.
  • the guest material of the organic electroluminescent layer 330 may be Ir(ppy) 3 or BD-1.
  • 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 ET-06 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 magnesium (Mg) and silver (Ag) 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 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 include Yb.
  • a hole blocking layer 340 may also be provided between the organic electroluminescent 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 provided in the present application 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.
  • a solar cell includes an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370, and an electron transport layer 350 which are sequentially stacked.
  • the embodiments of the present application also provide an electronic device, which includes any one of the electronic components described in the above-mentioned electronic component embodiments. Since the electronic device has any one of the electronic components described in the above-mentioned electronic component embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the present application provides a first electronic device 400
  • the first electronic device 400 includes any of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments.
  • 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. Since the electronic device 400 has any one of the organic electroluminescent devices described in the foregoing organic electroluminescent device embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the present application provides a second electronic device 500, and the second electronic device 500 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. Since the electronic device 500 has any one of the photoelectric conversion devices described in the foregoing photoelectric conversion device embodiments, it has the same beneficial effects, which will not be repeated here in this application.
  • the intermediate IM-X is obtained by the above reaction, where X can be 2, 3, and the reaction process is similar to that of the intermediate IM-1.
  • the obtained intermediates are shown in Table 1:
  • intermediate IM-1 Refer to the synthesis method of intermediate IM-1 to synthesize intermediate IM-10 and intermediate IM-11, and specifically use raw material B with different structures in Table 4 instead of o-bromoiodobenzene to obtain intermediate IM-X, where X can be 10 and 11.
  • the prepared intermediate IM-10 and intermediate IM-11 are shown in Table 4.
  • intermediate IM-1 to synthesize intermediate IM-12 and intermediate IM-14, and specifically use raw material C with different structures in Table 5 instead of o-bromoiodobenzene to obtain intermediate IM-X, where X can be 12 and 14, the prepared intermediate IM-12 and intermediate IM-14 are shown in Table 5.
  • intermediate IM-15 Refer to the synthesis method of intermediate IM-1 to synthesize intermediate IM-15 and intermediate IM-16, using raw material RM-D and raw material RM-E instead of o-bromo iodobenzene to obtain intermediate IM-15 and intermediate IM -16, the mass of the intermediate IM-15 is 51.3 g, and the yield is 67%, and the mass of the intermediate IM-16 is 50.5 g, and the yield is 66%.
  • Y can be 2 to 14, 16 to 18, 20 to 26, 101 to 123.
  • SMC with different structures in Table 8 is used instead of phenylboronic acid, and Each type of compound SMC has a unique corresponding compound Y. The obtained compounds are shown in Table 8:
  • the anode is prepared by the following process: the thickness of ITO is The substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with a pattern of cathode, anode, and insulating layer. The surface was surfaced with ultraviolet ozone and O 2 :N 2 plasma Treatment to increase the work function of the anode (experimental substrate) and remove dross.
  • F4-TCNQ was vacuum-evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and NPB is vapor-deposited on the hole injection layer to form a thickness of The hole transport layer.
  • HIL hole injection layer
  • Compound 1 was vacuum-evaporated on the hole transport layer to form a thickness of ⁇ electron blocking layer.
  • GH-n1 On the electron blocking layer, GH-n1: GH-n2: Ir(ppy) 3 is co-evaporated at a ratio of 50%: 45%: 5% (evaporation rate) to form a thickness of The green organic electroluminescent layer (EML).
  • EML green organic electroluminescent layer
  • ET-06 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form 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
  • EIL electron injection layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-05, forming an organic cover layer (CPL), thus completing the manufacture of organic light-emitting devices.
  • the use of the nitrogen-containing compound of the present application in the electron blocking layer can prepare an organic electroluminescent device with a lower working voltage.
  • Example Electron blocking layer Tg(°C) Te(°C) Example 1 Compound 1 135 234 Example 2 Compound 2 135 235 Example 3 Compound 3 136 233 Example 4 Compound 4 135 223 Example 5 Compound 5 145 240 Example 6 Compound 11 143 238 Example 7 Compound 12 135 222 Example 8 Compound 13 145 241 Example 9 Compound 14 145 242 Example 10 Compound 17 140 231 Example 11 Compound 18 137 229 Example 12 Compound 20 138 225 Example 13 Compound 21 135 216 Example 14 Compound 22 137 221 Example 15 Compound 24 141 236 Example 16 Compound 109 139 227 Example 17 Compound 110 139 226 Example 18 Compound 111 136 224 Example 19 Compound 112 135 210 Example 20 Compound 113 135 227 Example 21 Compound 116 136 223 Example 22 Compound 117 144 241 Example 23 Compound 118 140 229
  • Example 24 Compound 119 144 238 Example 25 Compound 121 143 237 Example 26 Compound 122 135 226 Example 27 Compound 123 135 223 Example 28 Compound 146 144 244 Example 29 Compound 147 138 216 Example 30 Compound 148 138 221 Example 31 Compound 149 142 239 Example 32 Compound 150 137 222 Example 33 Compound 151 139 227 Comparative example 1 Compound A-1 133 258 Comparative example 2 Compound B-1 111 278 Comparative example 3 Compound C-1 117 276
  • the compound of the present application has a lower possibility of decomposition during the evaporation and film formation process of a high-temperature device, and has a higher resistance to crystallization in an electric Joule heat environment during device operation.
  • the compound of the present application has a higher steric hindrance under the condition that the molecular weight of the compound of the present application is not much different, so that the vapor deposition temperature (Te) of the compound of the present application is reduced. Therefore, the compound of the present application has better thermal stability.
  • Example 34 Blue organic electroluminescent device
  • 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 The hole injection layer (HIL), and the compound NPB is vacuum-evaporated on the hole injection layer to form a thickness of The hole transport layer (HTL).
  • HIL hole injection layer
  • HTL hole transport layer
  • Compound 6 was vapor-deposited on the HTL as an electron blocking layer (EBL) with a thickness of EBL.
  • EBL electron blocking layer
  • the compound ⁇ , ⁇ -ADN is vapor-deposited on the EBL as the main body, and BD-1 is doped at the same time.
  • the main body and the dopant are formed with a film thickness ratio of 100:3 to form a thickness of The organic electroluminescent layer (EML).
  • EML organic electroluminescent layer
  • Thick hole blocking layer HBL
  • ET-06 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form 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
  • EIL electron injection layer
  • Mg magnesium
  • Ag silver
  • the vapor deposition thickness on the above cathode is CP-5 to form an organic cover layer (CPL) to complete the manufacture of organic light-emitting devices.
  • An organic electroluminescence device was produced in the same manner as in Example 34, except that the compounds shown in Table 13 below were used in place of Compound 6 when forming the electron blocking layer.
  • the driving voltage of the organic electroluminescent devices prepared in Examples 34-52 is reduced by at least 0.32V, and the current efficiency is (Cd/A) increased by at least 11.17%, external quantum efficiency increased by at least 11.11%, the least life span increased by 19.14%, and the highest life span increased by 124h.
  • the nitrogen-containing compound of the present application has a low vapor deposition temperature, and when used as an electron blocking layer material, an organic electroluminescent device with a low driving voltage can be manufactured.
  • Example Electron blocking layer Tg(°C) Te(°C) Example 34 Compound 6 136 227 Example 35 Compound 7 145 246 Example 36 Compound 8 142 244 Example 37 Compound 9 144 243 Example 38 Compound 10 136 226 Example 39 Compound 16 140 241 Example 40 Compound 23 137 224 Example 41 Compound 25 138 221 Example 42 Compound 26 139 239 Example 43 Compound 101 145 246 Example 44 Compound 102 143 243 Example 45 Compound 103 138 227 Example 46 Compound 104 135 226 Example 47 Compound 105 135 222 Example 48 Compound 106 143 243 Example 49 Compound 107 136 226
  • Example 50 Compound 108 137 224
  • Example 51 Compound 114 136 234
  • Example 52 Compound 115 145 247 Comparative example 4
  • Compound A-2 130 256
  • Comparative example 5 Compound B-2 122 272
  • Comparative example 6 Compound C-2 118 270
  • the compound of the present application has a lower possibility of decomposition during the evaporation and film formation process of a high-temperature device, and has a higher resistance to crystallization in an electric Joule heat environment during device operation.
  • the compound of the present application Compared with the compound of the comparative example, the compound of the present application has a higher steric hindrance, which reduces the evaporation temperature (Te) of the compound of the present application under the condition that the molecular weight is not much different. Therefore, the compound of the present application has better thermal stability.

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Abstract

本申请提供了一种含氮化合物、电子元件和电子装置，属于有机材料技术领域。所述含氮化合物的结构如化学式(1)所示，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
相关申请的交叉引用
本申请要求于2020年4月27日递交的申请号为CN202010346414.5的中国专利申请以及2020年8月20日递交的申请号为CN202010844829.5的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请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。
目前，在有机电致发光材料方面，绿光材料的性能比较好，但对于绿光和蓝光材料，目前性能尚不满足商业化要求，在彩色化方面寿命也只有几十个小时。因此，有必要开发新的材料，从而提高电子元器件的性能。
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 PCTCN2021082174-appb-000001
其中，
Figure PCTCN2021082174-appb-000002
表示化学键；
R a和R b分别独立地选自氢或化学式1-1所示的基团，且R a和R b中有且只有一个为化学式1- 1所示的基团；
L选自单键、取代或未取代的总碳原子数为6～30的亚芳基、取代或未取代的总碳原子数为3～30的亚杂芳基；
R 1选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基；
R 2选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1和R 2至少有一个选自取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基；
n 1和n 2分别为R 1和R 2的个数；
n 1选自0，1，2，3或4，当n 1大于1时，任意两个R 1相同或不同；
n 2选自0，1、2或3，当n 2大于1时，任意两个R 2相同或不同；
n 1+n 2≥1；
Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为3～20的环烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述Ar 1不为9,9-二苯基芴基，所述Ar 2不为9,9-二苯基芴基；
所述各L、R 1、R 2、Ar 1和Ar 2中的取代基分别独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为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18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基。
本申请提供的化合物，具有良好的空穴传输特性，能够应用于有机电致发光器件和光电转化器件的阳极与能量转化层之间，以提高阳极与能量转化层之间的空穴传输效率，进而提高有机电致发光器件的发光效率和光电转化器件的发电效率。
本申请设计了一种将芳胺基团引入到金刚烷螺芴基团上，其中金刚烷螺芴基团上带有芳基类型或杂芳基类型的取代基，能够增加化合物的空间位阻效应，其可以有效提升材料的玻璃化转变温度，并且螺合于芴基上的金刚烷基具有大的空间体积和较强的刚性，使得结构具有更高的电子耐受度以及成膜性，从而能够提高有机电致发光器件和光电转化器件的效率和寿命。其次，本申请化合物具有较低的工作电压。
不仅如此，此类化合物还具有更佳的热稳定性，能够在长时间高温下保持结构稳定，在相同分子量情况下，蒸镀温度下降，使得本申请含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量产稳定性。
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，所述电子元件为光电转化器件。
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。
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。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、空穴传输层；322、电子阻挡层；330、有机电致发光层；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。
本申请第一方面提供一种含氮化合物，所述含氮化合物的结构如化学式1所示：
Figure PCTCN2021082174-appb-000003
其中，
Figure PCTCN2021082174-appb-000004
表示化学键；
R a和R b分别独立地选自氢或化学式1-1所示的基团，且R a和R b中有且只有一个为化学式1-1所示的基团；
L选自单键、取代或未取代的总碳原子数为6～30的亚芳基、取代或未取代的总碳原子数为3～30的亚杂芳基；
R 1选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～10的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基；
R 2选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1和R 2至少有 一个选自取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基；
n 1和n 2分别为R 1和R 2的个数；
n 1选自0，1，2，3或4，当n 1大于1时，任意两个R 1相同或不同；
n 2选自0，1、2或3，当n 2大于1时，任意两个R 2相同或不同；
n 1+n 2≥1；
Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为3～20的环烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述Ar 1不为9,9-二苯基芴基，所述Ar 2不为9,9-二苯基芴基；
所述各L、R 1、R 2、Ar 1和Ar 2中的取代基分别独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为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18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基。
其中，“任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基”是指芳基可以被氘、氟、氯、氰基、甲基、叔丁基中的一个或多个取代，也可以不被氘、氟、氯、氰基、甲基、叔丁基取代，且当芳基上的取代基的个数大于等于2时，取代基可以相同或不同。
可选地，所述各L、R 1、R 2、Ar 1和Ar 2中的取代基分别独立地选自氘、卤素基团、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18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的膦氧基。
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 PCTCN2021082174-appb-000005
均为同一种结构。
本申请提供的化合物，具有良好的空穴传输特性，能够应用于有机电致发光器件和光电转化器件的阳极与能量转化层之间，以提高阳极与能量转化层之间的空穴传输效率，进而提高有机电致发光器件的发光效率和光电转化器件的发电效率。
本申请设计合成了一种将芳胺基团引入到金刚烷芴基团上，其中金刚烷螺芴基团上带有芳基类型或杂芳基类型的取代基，能够增加化合物的空间位阻效应，其可以有效提升材料的玻璃化转变温度，并且螺合于芴基上的金刚烷基具有大的空间体积和较强的刚性。这样的结构具有更高的电子耐受度以及成膜性，能够提高有机电致发光器件和光电转化器件的效率和寿命。不仅如此，此 类化合物还具有更佳的热稳定性，能够在长时间高温下保持结构稳定，尤其是连接基团L均为对位连接，在相同分子量情况下，蒸镀温度下降，空穴传输能力提高，电压降低。
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 PCTCN2021082174-appb-000006
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，L、Ar 1、Ar 2、R 1、R 2、R a和R b的取代或未取代的总碳原子数，指的是所有碳原子数。举例而言，若L选自取代的总碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar 1为
Figure PCTCN2021082174-appb-000007
则其总碳原子数为7；L为
Figure PCTCN2021082174-appb-000008
其总碳原子数为12。
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、Se、Si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；例如，“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个碳原子的中等大小烷基。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。
可选地，烷基选自碳原子数为1～6的烷基，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、仲丁基、叔丁基、戊基和己基。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，芳基中不含有B、N、O、S、P和Si等杂原子。举例而言，在本申请中，芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021082174-appb-000009
基等。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。
在本申请中，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、三联苯基、菲基、芴基。
应当理解地是，取代的芳基的碳原子数，指的是芳基和芳基上的取代基的碳原子总数，例如碳 原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。即在本申请中，芳基的碳原子数选自6个、7个、8个、9个、10个、11个、12个、13个、14个、15个、16个、17个、18个、19个、20个、21个、22个、23个、24个、25个、26个、27个、28个、29个或30个。
在本申请中，芴基可以是取代的，两个取代基可以彼此结合形成螺结构，具体实例包括但不限于以下结构：
Figure PCTCN2021082174-appb-000010
特别地，Ar 1不为
Figure PCTCN2021082174-appb-000011
Ar 2不为
Figure PCTCN2021082174-appb-000012
在本申请中，杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、苯并噻唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-芳基咔唑基(如N-苯基咔唑基)、N-杂芳基咔唑基(如N-吡啶基咔唑基)、N-烷基咔唑基(如N-甲基咔唑基)等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-芳基咔唑基、N-杂芳基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。
在本申请中，作为取代基的杂芳基具体实例包括但不限于：二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基等。
应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。即在本申请中，杂芳基的碳原子数选自3个、4个、5个、6个、7个、8个、9个、10个、11个、12个、13个、14个、15个、16个、17个、18个、19个、20个、21个、22个、23个、24个、25个、26个、27个、28个、29个或30个。
在本申请中，对芳基的解释可适用于亚芳基，对杂芳基的解释同样适用于亚杂芳基。
在本申请中，卤素基团可以为氟、氯、溴、碘。
本申请的含氮化合物的这些特性，使得其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。
按照本申请一种实施方式，L选自单键、取代或未取代的总碳原子数为6～20的亚芳基、取代或未取代的总碳原子数为5～20的亚杂芳基。
优选地，L选自单键、取代或未取代的总碳原子数为6～15的亚芳基。
在本申请中，L中的取代基选自氘、卤素、氰基、碳原子数为1～5的烷基。具体地，L中的取代基选自氘、氟、氰基、甲基、乙基、叔丁基等等。
按照本申请另一种实施方式，L选自单键或化学式j-1至化学式j-14所示基团所组成的组：
Figure PCTCN2021082174-appb-000013
其中，M 2选自单键或者
Figure PCTCN2021082174-appb-000014
表示化学键；
Q 1～Q 5和Q’ 1～Q’ 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 32中至少一个选自N；当Q 24～Q 32中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
E 1～E 14、J 5～J 9各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基，碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10 的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基，碳原子数为18～24的三芳基硅基；
e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
按照本申请一种实施方式，L选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基。
可选地，L选自单键或者如下基团所组成的组：
Figure PCTCN2021082174-appb-000015
可选地，L选自单键或者如下基团所组成的组：
Figure PCTCN2021082174-appb-000016
可选地，L中的取代基选自氘、甲基、乙基、叔丁基。
按照本申请一种实施方式，R 1和R 2相同或不同，且分别独立地选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～6的烷基、取代或未取代的总碳原子数为6～25的芳基、取代或未取代的总碳原子数为5～25的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基。
可选地，R 1选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～6的烷基、取代或未取代的总碳原子数为6～25的芳基、取代或未取代的总碳原子数为5～12的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基。具体地，R 1选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的蒽基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的亚吡啶基、取代或未取代的萘基、取代或未取代的二苯并呋喃基。
可选地，R 2选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～6的烷基、取代或未取代的总碳原子数为6～25的芳基、取代或未取代的总碳原子数为5～18的杂芳基。具体地，R 2选 自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的蒽基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的芘基、取代或未取代的亚吡啶基、取代或未取代的萘基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基。
在本申请一种实施方式中，R 1和R 2中的取代基的相同或不同，且分别独立地选自：氘、氰基、卤素基团、取代或未取代的总碳原子数为1～6的烷基、碳原子数为6～20的芳基、碳原子数为3～20的杂芳基，且所述R 1的取代基不为咔唑基。
可选地，R 1中的取代基选自：氘、氟、甲基、乙基、叔丁基、苯基、萘基、联苯基、氰基。
可选地，R 2中的取代基选自：氘、氟、甲基、乙基、叔丁基、苯基、萘基、联苯基、咔唑基、N-苯基咔唑基、氰基。
在本申请一种实施方式中，R 1选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组，但不仅限于此：
Figure PCTCN2021082174-appb-000017
在本申请一种实施方式中，R 2选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组，但不仅限于此：
Figure PCTCN2021082174-appb-000018
可选地，R 1选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组：
Figure PCTCN2021082174-appb-000019
可选地，R 2选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组：
Figure PCTCN2021082174-appb-000020
在本申请一种实施方式中，Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为6～24的芳基、取代或未取代的总碳原子数为3～24的杂芳基。
可选地，Ar 1和Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子 数为1～5的烷基、碳原子数为3～15的环烷基、碳原子数为6～18的芳基、碳原子数为12～18的杂芳基。具体地，Ar 1和Ar 2中的取代基相同或不同，且分别独立地选自氘、氟、甲基、乙基、正丙基、异丙基、叔丁基、环己烷基、金刚烷基、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基。
优选地，Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为6～21的芳基、取代或未取代的总碳原子数为12～24的杂芳基。
在本申请另一种实施方式中，Ar 1和Ar 2相同或不同，且分别独立地选自如下化学式i-1至化学式i-15所示的基团：
Figure PCTCN2021082174-appb-000021
其中，M 1选自单键或者
Figure PCTCN2021082174-appb-000022
G 1～G 5和G’ 1～G’ 4各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个 以上选自C(J 2)时，任意两个J 2相同或者不相同；
G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～10的烷硫基、碳原子数为3～18的杂芳基、碳原子数为18～24的三芳基硅基；
Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、乙基、叔丁基的取代基所取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18～24的三芳基硅基；
h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
在本申请另一种实施方式中，Ar 1和Ar 2分别选自如下化学式i-16所示的基团：
Figure PCTCN2021082174-appb-000023
Z 32、Z 33各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、 甲基、乙基、叔丁基的取代基所取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18-24的三芳基硅基；
h 32为Z 32的个数，h 33为Z 33的个数；
h 32选自0，1，2或3，当h 32大于1时，任意两个Z 32相同或不同；
h 33选自0，1，2，3，4或5，当h 33大于1时，任意两个Z 33相同或不同。
在本申请一种实施方式中，Ar 1和Ar 2相同或不同，且分别独立地选自如下基团所组成的组，但不仅限于此：
Figure PCTCN2021082174-appb-000024
在本申请中，
Figure PCTCN2021082174-appb-000025
是指
Figure PCTCN2021082174-appb-000026
可选地，Ar 1和Ar 2相同或不同，且分别独立地选自如下基团所组成的组，但不仅限于此：
Figure PCTCN2021082174-appb-000027
可选地，所述含氮化合物选自如下化合物所组成的组，但不仅限于此：
Figure PCTCN2021082174-appb-000028
Figure PCTCN2021082174-appb-000029
Figure PCTCN2021082174-appb-000030
Figure PCTCN2021082174-appb-000031
Figure PCTCN2021082174-appb-000032
Figure PCTCN2021082174-appb-000033
本申请还提供一种电子元件，用于实现光电转换或者电光转化。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。
举例而言，电子元件为一种有机电致发光器件。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。
优选地，所述有机电致发光器件为绿色有机电致发光器件或蓝色有机电致发光器件。
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或者空穴注入层310，空穴传输层321或者空穴注入层310中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有机电致发光器件的电子阻挡层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。举例而言，在本申请的一种实施方式中，空穴传输层321由化合物NPB组成。
可选地，有机电致发光层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，有机电致发光层330由主体材料和客体材料组成，注入有机电致发光层330的空穴和注入有机电致发光层330的电子可以在有机电致发光层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。
有机电致发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机电致发光层330的主体材料可以为GH-n1和GH-n2的组合物或α,β-ADN。
有机电致发光层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。在本申请的一种实施方式中，有机电致发光层330的客体材料可以为Ir(ppy) 3或BD-1。
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。举例而言，在本申请的一种实施方式中，电子传输层350可以由ET-06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。优选包括包含镁(Mg)和银(Ag)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。在本申请的一种实施方式中，空穴注入层310可以由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层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。在本申请的一种实施方式中，电子注入层360可以包括Yb。
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。
再举例而言，电子元件可以为一种光电转化器件，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，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。举例而言，如图2所示，在本申请的一种实施方式中，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。
本申请实施方式还提供一种电子装置，该电子装置包括上述电子元件实施方式所描述的任意一种电子元件。由于该电子装置具有上述电子元件实施方式所描述的任意一种电子元件，因此具有相同的有益效果，本申请在此不再赘述。
举例而言，如图3所示，本申请提供第一电子装置400，第一电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。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。由于该电子装置400具有上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
再举例而言，如图4所示，本申请提供第二电子装置500，第二电子装置500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。由于该电子装置500具有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，因此具有相同的有益效果，本申请在此不再赘述。
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。
化合物的合成
Figure PCTCN2021082174-appb-000034
将SM1(100g,524.1mmol)、邻溴碘苯(148.26g,524.1mmol)、四(三苯基膦)钯(30.2g,26.2mmol)、碳酸钾(216.9g,1572.2mol)、四丁基氯化铵(7.25g,26.2mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(500mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯(体积比1:3)体系进行重结晶提纯，得到中间体IM-1-1(134.5g,收率85％)。
将中间体IM-1-1(100g,331.13mmol)加入盛有THF(1L)的三口瓶中，-80℃下滴加正丁基锂(25.45g,397.35mmol)，滴加完后保温1h后滴加金刚烷酮(39.78g,264.90mmol)，继续保温1h后 升温至室温搅拌过夜。加入盐酸(2mol/L)调节pH至中性，后过滤得白色粗品，用正庚烷打浆得白色固体中间体IM-1-2(86.52g,收率70％)。
将中间体IM-1-2(86.52g,231.77mmol)、三氟乙酸(79.28g,695.31mmol)和二氯甲烷(900mL)加入三口烧瓶中，氮气保护下搅拌2小时；加入氢氧化钠水溶液至反应液呈中性，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(体积比1:2)进行硅胶柱色谱提纯，得到白色固体状中间体IM-1(70.82g,收率：86％)。
Figure PCTCN2021082174-appb-000035
在一种实施方式中，中间体IM-X由上式反应得到，其中，X可以是2、3，其反应过程与中间体IM-1相似，用表1中的SMA代替SM1，制备中间体IM-X-1、中间体IM-X-2、中间体IM-X。所得中间体如表1所示：
表1
Figure PCTCN2021082174-appb-000036
中间体IM-2核磁：
1HNMR(400MHz,CD 2Cl 2),δ(ppm)：8.07(d,1H),7.97(s,1H),7.83(s,1H),7.29-7.26(m,1H),7.19-7.16(m,1H),7.08(d,1H),2.91-2.83(m,4H),2.73-2.39(m,4H),2.19(s,2H),1.92(d,2H),1.56(s,2H).
中间体IM-3核磁：
1HNMR(400MHz,CD 2Cl 2),δ(ppm)：8.08(d,1H),7.88-7.25(m,2H),7.30-7.26(m,1H),7.19(d,1H),7.11-7.07(m,1H),2.62-2.59(m,4H),2.48-2.45(m,4H),2.03(s,2H),1.89(d,2H),1.56(s,2H).
Figure PCTCN2021082174-appb-000037
将2-溴-4-氯-1-碘苯(100g,315.1mmol)、对氯苯硼酸(49.27g,315.1mmol)、四(三苯基膦)钯(18.21g,15.7mmol)、碳酸钾(87.1g,630.2mmol)、四丁基氯化铵(3.59g,15.7mmol)、甲苯(800mL)、乙醇(400mL)和去离子水(200mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌8小时；将反应液冷却至室温，加入甲苯(500mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥， 过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯，得到白色固体中间体IM-4-1(75.16g,收率79％)。
将中间体IM-4-1(100g,331.13mmol)加入盛有THF(1L)的三口瓶中，-80℃下滴加正丁基锂(25.45g,397.35mmol)，滴加完后保温1h后滴加金刚烷酮(39.78g,264.90mmol)，继续保温1h后升温至室温搅拌过夜。加入盐酸(2mol/L)调节PH至中性，后过滤得白色粗品，用正庚烷打浆得固体中间体IM-4-2(86.52g,收率87％)。
将中间体IM-4-2(86.52g,231.77mmol)、三氟乙酸(79.28g,695.31mmol)和二氯甲烷(900mL)加入三口烧瓶中，氮气保护下搅拌2小时；加入氢氧化钠水溶液至反应液呈中性，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(体积比1:2)进行硅胶柱色谱提纯，得到白色固体状中间体IM-4(70.82g,收率86％)。
Figure PCTCN2021082174-appb-000038
参照中间体IM-4的合成方法，合成中间体IM-5、中间体IM-6和中间体IM-17，具体使用表2中不同结构的原料1代替2-溴-4-氯-1-碘苯，原料2代替对氯苯硼酸得到中间体IM-X，其中X可以为5、6或17，制得的中间体IM-5、中间体IM-6和中间体IM-17如表2所示。
表2
Figure PCTCN2021082174-appb-000039
Figure PCTCN2021082174-appb-000040
Figure PCTCN2021082174-appb-000041
参照中间体IM-1的合成方法，合成中间体IM-7和中间体IM-8，具体使用表3中不同结构的原料A代替邻溴碘苯，制得的中间体IM-7和中间体IM-8如表3所示。
表3
Figure PCTCN2021082174-appb-000042
Figure PCTCN2021082174-appb-000043
Figure PCTCN2021082174-appb-000044
参照中间体IM-1的合成方法，合成中间体IM-10和中间体IM-11，具体使用表4中不同结构的原料B代替邻溴碘苯，得到中间体IM-X，其中X可以为10、11，制得的中间体IM-10和中间体IM-11如表4所示。
表4
Figure PCTCN2021082174-appb-000045
Figure PCTCN2021082174-appb-000046
Figure PCTCN2021082174-appb-000047
参照中间体IM-1的合成方法，合成中间体IM-12和中间体IM-14，具体使用表5中不同结构的原料C代替邻溴碘苯，得到中间体IM-X，其中X可以为12、14，制得的中间体IM-12和中间体IM-14如表5所示。
表5
Figure PCTCN2021082174-appb-000048
Figure PCTCN2021082174-appb-000049
Figure PCTCN2021082174-appb-000050
参照中间体IM-1的合成方法，合成中间体IM-15和中间体IM-16，分别使用原料RM-D、原料RM-E代替邻溴碘苯，得到中间体IM-15和中间体IM-16，中间体IM-15的质量为51.3g，收率为67％、中间体IM-16的质量为50.5g，收率为66％。
Figure PCTCN2021082174-appb-000051
将中间体IM-1(20g,56.29mmol)、对溴苯硼酸(11.31g,56.29mmol)、四(三苯基膦)钯(3.25g,2.81mmol)、碳酸钾(23.3g,168.8mmol)、四丁基氯化铵(0.78g,2.81mmol)、甲苯(160mL)、乙醇(40mL)和去离子水(40mL)加入圆底烧瓶中，氮气保护下升温至78℃，搅拌12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(体积比1:3)体系进行重结晶提纯，得到中间体IM-1-A(22.7g,85％)。
在一种实施方式中，参照中间体IM-1-A的合成方法，用表6中不同结构的SMD代替对溴苯硼酸，合成下表6所示的中间体IM-MM，每一种类型的化合物SMD具有与之唯一对应的中间体MM。合成的中间体IM-MM如表6所示：
表6
Figure PCTCN2021082174-appb-000052
Figure PCTCN2021082174-appb-000053
Figure PCTCN2021082174-appb-000054
Figure PCTCN2021082174-appb-000055
向反应瓶中投入中间体IM-1(20g,56.29mmol)、二苯胺(9.53g,56.29mmol)、三(二亚苄基丙酮)二钯(0.52g,0.56mmol)、2-二环己基膦-2,4,6,-三异丙基联苯(0.46g,1.12mmol)、叔丁醇钠(8.10g,84.4mmol)和甲苯溶剂(250mL)，氮气保护下升温至110℃，加热回流搅拌3h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，有机层经无水硫酸镁干燥并过滤，过滤后将滤液通过短硅胶柱，减压除去溶剂，使用二氯甲烷/正庚烷体系(体积比1:3)对粗品进行重结晶提纯，得到中间体IM-A(20.6g,收率为75％)。
在一种实施方式中，参照中间体IM-A的合成方法，用表7中不同结构的SMB代替二苯胺，合成下表7所示的中间体IM-Y，其中，每一种类型的化合物SMB具有与之唯一对应的中间体IM-Y。所得中间体如表7所示：
表7
Figure PCTCN2021082174-appb-000056
Figure PCTCN2021082174-appb-000057
Figure PCTCN2021082174-appb-000058
Figure PCTCN2021082174-appb-000059
Figure PCTCN2021082174-appb-000060
Figure PCTCN2021082174-appb-000061
Figure PCTCN2021082174-appb-000062
Figure PCTCN2021082174-appb-000063
Figure PCTCN2021082174-appb-000064
化合物1的合成
Figure PCTCN2021082174-appb-000065
将中间体IM-A(10g,20.4mmol)、苯硼酸(2.50g,20.4mmol)、四(三苯基膦)钯(1.18g,1.02mmol)、碳酸钾(8.48g,61.4mmol)、四丁基氯化铵(0.28g,1.02mmol)、甲苯(80mL)、乙醇(40mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至78℃，搅拌10小时；将反应液冷却至室温，加入甲苯(250mL)进行萃取，合并有机相，有机相用无水硫酸镁进行干燥，过滤得到滤液，将滤液减压浓缩得到粗品；所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯，之后用二氯甲烷/正庚烷(体积比1:3)体系进行重结晶提纯，得到化合物1(7.05g,收率65％)。m/z＝530.2[M+H] +。
Figure PCTCN2021082174-appb-000066
在一种实施方式中，参照化合物1的合成方法合成化合物Y，Y可以是2至14、16至18、20至26、101至123，具体用表8中不同结构的SMC代替苯硼酸，且每一种类型的化合物SMC具有与之唯一对应的化合物Y。所得化合物如表8所示：
表8
Figure PCTCN2021082174-appb-000067
Figure PCTCN2021082174-appb-000068
Figure PCTCN2021082174-appb-000069
Figure PCTCN2021082174-appb-000070
Figure PCTCN2021082174-appb-000071
Figure PCTCN2021082174-appb-000072
Figure PCTCN2021082174-appb-000073
Figure PCTCN2021082174-appb-000074
Figure PCTCN2021082174-appb-000075
Figure PCTCN2021082174-appb-000076
向反应瓶中投入中间体IM-Q-1(20g,38.3mmol)、SM-L(4496-49-5)(8.6g,38.3mmol)、三(二亚苄基丙酮)二钯(0.35g,0.38mmol)、2-二环己基膦-2,4,6,-三异丙基联苯(0.35g,0.76mmol)、叔丁醇钠(5.5g,57.3mmol)和甲苯溶剂(160mL)，氮气保护下升温至110℃，加热回流搅拌3h。反应液冷却至室温后，利用二氯甲烷和水萃取反应溶液，有机层经无水硫酸镁干燥并过滤，过滤后将滤液通过短硅胶柱，减压除去溶剂，使用二氯甲烷/正庚烷体系(体积比1:3)对粗品进行重结晶提纯，得到化合物146(19.1g,收率为：70％)。m/z＝712.3[M+H]+。
在一种实施方式中，参照化合物146的合成方法，用表9中不同结构的SMQ代替SM-L，中间体IM-Q-X代替中间体IM-Q-1，合成化合物Z。且每一种类型的化合物SMQ具有与之唯一对应的化合物Z。所得化合物如表9所示：
表9
Figure PCTCN2021082174-appb-000077
Figure PCTCN2021082174-appb-000078
部分化合物核磁数据如下表10所示
表10
Figure PCTCN2021082174-appb-000079
Figure PCTCN2021082174-appb-000080
有机电致发光器件制备及评估
实施例1：绿色有机电致发光器件
通过以下过程制备阳极：将ITO厚度为
Figure PCTCN2021082174-appb-000081
的基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为的厚度为
Figure PCTCN2021082174-appb-000082
的空穴注入层(HIL)，并且在空穴注入层蒸镀NPB，形成厚度为
Figure PCTCN2021082174-appb-000083
的空穴传输层。
在空穴传输层上真空蒸镀化合物1，形成厚度为
Figure PCTCN2021082174-appb-000084
的电子阻挡层。
在电子阻挡层上，将GH-n1：GH-n2：Ir(ppy) 3以50％：45％：5％(蒸镀速率)的比例进行共同蒸镀，形成厚度为
Figure PCTCN2021082174-appb-000085
的绿色有机电致发光层(EML)。
将ET-06和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021082174-appb-000086
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 PCTCN2021082174-appb-000087
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 PCTCN2021082174-appb-000088
的阴极。
在上述阴极上蒸镀厚度为
Figure PCTCN2021082174-appb-000089
的CP-05，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2-33
除了在形成电子阻挡层时，用以下表11中所示的化合物替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
对比例1
除了在形成电子阻挡层时，用化合物A-1替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
对比例2
除了在形成电子阻挡层时，用化合物B-1替代化合物1以外，利用与实施例1相同的方法制作有机电致发光器件。
对比例3
除了在形成电子阻挡层时，用化合物C-1替代化合物1以外，利用与实施例1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所示：
Figure PCTCN2021082174-appb-000090
Figure PCTCN2021082174-appb-000091
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果示于下表11所示：
表11
Figure PCTCN2021082174-appb-000092
Figure PCTCN2021082174-appb-000093
根据上表11可知，在色坐标相差不大的情况下，相较于对比例1～3而言，实施例1～33制备的有机电致发光器件的驱动电压至少降低了0.25V，电流效率(Cd/A)至少提高了8.7％，外量子效率至少提高了8.7％，寿命最少的提高了4.4％，最高的寿命可提高93h。
因此，在电子阻挡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。
表12
实施例 电子阻挡层 Tg(℃) Te(℃)
实施例1 化合物1 135 234
实施例2 化合物2 135 235
实施例3 化合物3 136 233
实施例4 化合物4 135 223
实施例5 化合物5 145 240
实施例6 化合物11 143 238
实施例7 化合物12 135 222
实施例8 化合物13 145 241
实施例9 化合物14 145 242
实施例10 化合物17 140 231
实施例11 化合物18 137 229
实施例12 化合物20 138 225
实施例13 化合物21 135 216
实施例14 化合物22 137 221
实施例15 化合物24 141 236
实施例16 化合物109 139 227
实施例17 化合物110 139 226
实施例18 化合物111 136 224
实施例19 化合物112 135 210
实施例20 化合物113 135 227
实施例21 化合物116 136 223
实施例22 化合物117 144 241
实施例23 化合物118 140 229
实施例24 化合物119 144 238
实施例25 化合物121 143 237
实施例26 化合物122 135 226
实施例27 化合物123 135 223
实施例28 化合物146 144 244
实施例29 化合物147 138 216
实施例30 化合物148 138 221
实施例31 化合物149 142 239
实施例32 化合物150 137 222
实施例33 化合物151 139 227
对比例1 化合物A-1 133 258
对比例2 化合物B-1 111 278
对比例3 化合物C-1 117 276
由表12可知，本申请化合物在高温器件蒸镀成膜过程中具有较低的分解可能性，并且在器件运行中具有在电焦耳热环境下更高的结晶抵抗性。
本申请化合物与对比例化合物相比，在分子量相差不大的情况下，本申请化合物由于较高的空间位阻，使得本申请化合物的蒸镀温度(Te)降低。因此，本申请化合物具有更好的热稳定性。
实施例34：蓝色有机电致发光器件
通过以下过程制备阳极：将厚度为
Figure PCTCN2021082174-appb-000094
的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸，采用光刻工序，将其制备成具有阴极、阳极以及绝缘层图案的实验基板，利用紫外臭氧以及O 2:N 2等离子进行表面处理，以增加阳极(实验基板)的功函数的和清除浮渣。
在实验基板(阳极)上真空蒸镀F4-TCNQ以形成厚度为
Figure PCTCN2021082174-appb-000095
的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀化合物NPB，以形成厚度为
Figure PCTCN2021082174-appb-000096
的空穴传输层(HTL)。
在HTL上蒸镀化合物6作为电子阻挡层(EBL)，厚度为
Figure PCTCN2021082174-appb-000097
在EBL上蒸镀以化合物α,β-ADN作为主体，同时掺杂BD-1，主体和掺杂剂按以100:3的膜厚比，形成了厚度为
Figure PCTCN2021082174-appb-000098
的有机电致发光层(EML)。
在有机电致发光层上，将化合物ET-1蒸镀形成了
Figure PCTCN2021082174-appb-000099
厚的空穴阻挡层(HBL)。
将ET-06和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021082174-appb-000100
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 PCTCN2021082174-appb-000101
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 PCTCN2021082174-appb-000102
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021082174-appb-000103
的CP-5，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例35-52
除了在形成电子阻挡层时，以下表13中所示的化合物替代化合物6以外，利用与实施例34相同的方法制作有机电致发光器件。
对比例6
除了在形成电子阻挡层时，用化合物A-2替代化合物6以外，利用与实施例34相同的方法制作有机电致发光器件。
对比例7
除了在形成电子阻挡层时，用化合物B-2替代化合物6以外，利用与实施例34相同的方法制作有机电致发光器件。
对比例8
除了在形成电子阻挡层时，用化合物C-2替代化合物6以外，利用与实施例34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所示：
Figure PCTCN2021082174-appb-000104
对如上制得的有机电致发光器件，在20mA/cm 2的条件下分析了器件的性能，其结果示于下表13所示：
表13
Figure PCTCN2021082174-appb-000105
Figure PCTCN2021082174-appb-000106
根据上表13可知，在色坐标相差不大的情况下，相较于对比例4～6而言，实施例34～52制备的有机电致发光器件的驱动电压至少降低了0.32V，电流效率(Cd/A)至少提高了11.17％，外量子效率至少提高了11.11％，寿命最少的提高了19.14％，最高的寿命可提高124h。
可见，本申请的含氮化合物蒸镀温度低，作为电子阻挡层材料时，可制造低驱动电压的有机电致发光器件。
表14
实施例 电子阻挡层 Tg(℃) Te(℃)
实施例34 化合物6 136 227
实施例35 化合物7 145 246
实施例36 化合物8 142 244
实施例37 化合物9 144 243
实施例38 化合物10 136 226
实施例39 化合物16 140 241
实施例40 化合物23 137 224
实施例41 化合物25 138 221
实施例42 化合物26 139 239
实施例43 化合物101 145 246
实施例44 化合物102 143 243
实施例45 化合物103 138 227
实施例46 化合物104 135 226
实施例47 化合物105 135 222
实施例48 化合物106 143 243
实施例49 化合物107 136 226
实施例50 化合物108 137 224
实施例51 化合物114 136 234
实施例52 化合物115 145 247
对比例4 化合物A-2 130 256
对比例5 化合物B-2 122 272
对比例6 化合物C-2 118 270
由表14可知，本申请化合物在高温器件蒸镀成膜过程中具有较低的分解可能性，并且在器件运行中具有在电焦耳热环境下更高的结晶抵抗性。
本申请化合物与比较例化合物相比，在分子量相差不大的情况下，本申请化合物由于较高的空间位阻，使得本申请化合物的蒸镀温度(Te)降低。因此，本申请化合物具有更好的热稳定性。
以上结合附图详细描述了本申请的优选实施方式，但是，本申请并不限于上述实施方式中的具体细节，在本申请的技术构思范围内，可以对本申请的技术方案进行多种简单变型，这些简单变型均属于本申请的保护范围。
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合，为了避免不必要的重复，本申请对各种可能的组合方式不再另行说明。
此外，本申请的各种不同的实施方式之间也可以进行任意组合，只要其不违背本申请的思想，其同样应当视为本申请所公开的内容。

Claims (18)

  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 PCTCN2021082174-appb-100001
    其中，
    Figure PCTCN2021082174-appb-100002
    表示化学键；
    R a和R b分别独立地选自氢或化学式1-1所示的基团，且R a和R b中有且只有一个为化学式1-1所示的基团；
    L选自单键、取代或未取代的总碳原子数为6～30的亚芳基、取代或未取代的总碳原子数为3～30的亚杂芳基；
    R 1选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基；
    R 2选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述R 1和R 2至少有一个选自取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基；
    n 1和n 2分别为R 1和R 2的个数；
    n 1选自0，1，2，3或4，当n 1大于1时，任意两个R 1相同或不同；
    n 2选自0，1，2或3，当n 2大于1时，任意两个R 2相同或不同；
    n 1+n 2≥1；
    Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为1～20的烷基、取代或未取代的总碳原子数为3～20的环烷基、取代或未取代的总碳原子数为6～30的芳基、取代或未取代的总碳原子数为3～30的杂芳基，且所述Ar 1不为9,9-二苯基芴基，所述Ar 2不为9,9-二苯基芴基；
    所述各L、R 1、R 2、Ar 1和Ar 2中的取代基分别独立地选自氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为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18～24的三芳基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基。
  2. 根据权利要求1所述的含氮化合物，其特征在于，所述各L、R 1、R 2、Ar 1和Ar 2中的取代基分别独立地选自氘、卤素基团、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18～24的三芳基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、 碳原子数为4～10的杂环烯基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为6～18的芳氧基、碳原子数为6～18的芳硫基、碳原子数为6～18的膦氧基。
  3. 根据权利要求1或2所述的含氮化合物，其特征在于，L选自单键、取代或未取代的总碳原子数为6～20的亚芳基、取代或未取代的总碳原子数为5～20的亚杂芳基。
  4. 根据权利要求1～3中任意一项所述的含氮化合物，其特征在于，L选自单键或化学式j-1至化学式j-14所示基团所组成的组：
    Figure PCTCN2021082174-appb-100003
    其中，M 2选自单键或者
    Figure PCTCN2021082174-appb-100004
    表示化学键；
    Q 1～Q 5和Q’ 1～Q’ 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
    Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
    Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
    Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 32中至少一个选自N；当Q 24～Q 32中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
    E 1～E 14、J 5～J 9各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选 地被0、1、2、3、4或5个选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为2～6的烯基，碳原子数为2～6的炔基，碳原子数为3～10的环烷基，碳原子数为2～10的杂环烷基，碳原子数为5～10的环烯基，碳原子数为4～10的杂环烯基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，碳原子数为6～18的芳氧基，碳原子数为6～18的芳硫基，碳原子数为6～18的膦氧基，碳原子数为18～24的三芳基硅基；
    e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
    K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
    K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为2～6的烯基、碳原子数为2～6的炔基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、碳原子数为5～10的环烯基、碳原子数为4～10的杂环烯基，或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
  5. 根据权利要求1～4中任意一项所述的含氮化合物，其特征在于，L选自单键、取代或未取代的总碳原子数为6～15的亚芳基。
  6. 根据权利要求1～5中任意一项所述的含氮化合物，其特征在于，L选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚芴基。
  7. 根据权利要求1～6中任意一项所述的含氮化合物，其特征在于，L选自单键或者如下基团所组成的组：
    Figure PCTCN2021082174-appb-100005
  8. 根据权利要求1～7中任意一项所述的含氮化合物，其特征在于，R 1和R 2相同或不同，且分别独立地选自氘、氰基、卤素基团、取代或未取代的总碳原子数为1～6的烷基、取代或未取代的总碳原子数为6～25的芳基、取代或未取代的总碳原子数为5～25的杂芳基，且所述R 1不为咔唑基或N-苯基咔唑基。
  9. 根据权利要求1～8中任意一项所述的含氮化合物，其特征在于，R 1选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组：
    Figure PCTCN2021082174-appb-100006
  10. 根据权利要求1～9中任意一项所述的含氮化合物，其特征在于，R 2选自氘、卤素基团、甲基、乙基、叔丁基或如下基团所组成的组：
    Figure PCTCN2021082174-appb-100007
  11. 根据权利要求1～9中任意一项所述的含氮化合物，其特征在于，R 2选自如下基团：
    Figure PCTCN2021082174-appb-100008
  12. 根据权利要求1～11中任意一项所述的含氮化合物，其特征在于，Ar 1和Ar 2相同或不同，且分别独立地选自取代或未取代的总碳原子数为6～24的芳基、取代或未取代的总碳原子数为3～24的杂芳基。
  13. 根据权利要求1～12中任意一项所述的含氮化合物，其特征在于，Ar 1和Ar 2相同或不同，且分别独立地选自如下化学式i-1至化学式i-15所示的基团：
    Figure PCTCN2021082174-appb-100009
    其中，M 1选自单键或者
    Figure PCTCN2021082174-appb-100010
    G 1～G 5和G’ 1～G’ 4各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
    G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
    G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
    G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
    Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
    Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～10的烷硫基、碳原子数为3～18的杂芳基、碳原子数为18-24的三芳基硅基；
    Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被0、1、2、3、4、5个选自氘、氟、氯、氰基、甲基、乙基、叔丁基的取代基所取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18～24的三芳基硅基；
    h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
    K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
    K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
  14. 根据权利要求1～13中任意一项所述的含氮化合物，其特征在于，Ar 1和Ar 2相同或不同，且分别独立地选自如下基团所组成的组：
    Figure PCTCN2021082174-appb-100011
  15. 根据权利要求1～14中任意一项所述的含氮化合物，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 PCTCN2021082174-appb-100012
    Figure PCTCN2021082174-appb-100013
    Figure PCTCN2021082174-appb-100014
    Figure PCTCN2021082174-appb-100015
    Figure PCTCN2021082174-appb-100016
    Figure PCTCN2021082174-appb-100017
  16. 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1～15中任一项所述的含氮化合物；
    优选地，所述功能层包括电子阻挡层，所述电子阻挡层包括所述含氮化合物。
  17. 根据权利要求16所述的电子元件，其特征在于，所述电子元件为有机电致发光器件或光电转化器件；
    优选地，所述有机电致发光器件为绿色有机电致发光器件或蓝色有机电致发光器件。
  18. 一种电子装置，其特征在于，包括权利要求16或17所述的电子元件。
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