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WO2022007909A1 - 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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Publication number
WO2022007909A1
WO2022007909A1 PCT/CN2021/105331 CN2021105331W WO2022007909A1 WO 2022007909 A1 WO2022007909 A1 WO 2022007909A1 CN 2021105331 W CN2021105331 W CN 2021105331W WO 2022007909 A1 WO2022007909 A1 WO 2022007909A1
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carbon atoms
group
substituted
independently selected
nitrogen
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PCT/CN2021/105331
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English (en)
French (fr)
Inventor
马天天
杨雷
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陕西莱特迈思光电材料有限公司
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Priority to US18/011,219 priority Critical patent/US20230250048A1/en
Publication of WO2022007909A1 publication Critical patent/WO2022007909A1/zh

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Definitions

  • the present application relates to the technical field of organic materials, and in particular, to a nitrogen-containing compound, an electronic component including the nitrogen-containing compound, and an electronic device including the electronic component.
  • Such electronic components usually include oppositely disposed cathodes and anodes, and functional layers disposed between the cathodes and the anodes.
  • the functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
  • an organic electroluminescence device as an example, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence.
  • an electric field is generated between the two electrodes.
  • the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer, and the electrons and holes combine in the electroluminescent layer.
  • Excitons are formed, and the excitons are in an excited state to release energy to the outside, thereby causing the electroluminescent layer to emit light to the outside.
  • JP2012167058A discloses a light-emitting layer material with 1,8-disubstituted naphthalene as a basic structure
  • KR1020150006374A discloses a hole transport layer material with disubstituted naphthalene as a connecting group.
  • the purpose of the present 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 first aspect of the present application provides a nitrogen-containing compound, and the structure of the nitrogen-containing compound is shown in Formula 1:
  • B 1 and B 2 are the same or different from each other, and are each independently selected from the groups represented by Formula 1-1, Formula 1-2 or Formula 1-3, and B 1 and B 2 are not the same as Formula 1-1 and Formula 1-3.
  • Ar 1 , Ar 2 , Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms in total, substituted or unsubstituted aryl groups having 3-30 carbon atoms in total Heteroaryl;
  • L 1 is selected from a substituted or unsubstituted arylene group with a total carbon number of 6-20, a substituted or unsubstituted heteroarylene group with a total carbon number of 4-15;
  • L 2 and L 3 are the same or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6-20, a substituted or unsubstituted group with a total carbon number of 4-15 the heteroarylene;
  • R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, carbon atom Alkenyl group with 2-6 carbon atoms, cycloalkyl group with carbon number of 3-10, group A, heteroaryl group with carbon number of 3-20, alkoxy group with carbon number of 1-10, carbon Alkylthio group with 1-10 atoms or trialkylsilyl group with 3-12 carbon atoms; group A is selected from substituted or unsubstituted aryl groups with total carbon number of 6-20, among the aryl groups The substituents are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-4 carbon atoms, haloalkyl group with carbon number of 1-4, cycloalkyl group with carbon number of 3-10 or trialkylsilyl with 3-7 carbon atoms;
  • n 1 is the number of substituent R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n 1 is greater than 1, any two R 1 are the same or different, optionally, Any two adjacent R 1 form a ring;
  • n 2 is the number of substituent R 2 , n 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when n 2 is greater than 1, any two R 2 are the same or different, optionally, any two adjacent R 2 form a ring;
  • the substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3- Heteroaryl of 18, alkyl of 1-10 carbon atoms, haloalkyl of 1-10 of carbon atoms, cycloalkyl of 3-10 of carbon atoms, alkoxy of 1-10 of carbon atoms base, alkylthio group with 1-10 carbon atoms or trialkylsilyl group with 3-12 carbon atoms;
  • the substituents in L 1 , L 2 and L 3 are the same or different, and each is independently selected from: deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, 3- Heteroaryl with 12, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms base, alkylthio group with 1-10 carbon atoms or trialkylsilyl group with 3-12 carbon atoms;
  • any two adjacent substituents form a ring;
  • B 1 and B 2 are not simultaneously When the structure is selected from formula 1-3 B 1, and L 3 is a substituted or unsubstituted 1,4-phenylene, B 2 and B 1 different from the structure.
  • a second aspect of the present application provides an electronic component, the electronic component includes an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the first aspect the nitrogen-containing compounds mentioned.
  • a third aspect of the present application provides an electronic device, which includes the electronic component described in the second aspect.
  • the nitrogen-containing compound of the present application uses 1,8-disubstituted naphthalene as the core structure, and combines triarylamine and/or groups including carbazole-like structures in a specific manner as the substituent of 1,8-disubstituted naphthalene
  • triarylamine and carbazole-like groups with strong hole transport properties are stacked face to face in close space, thus forming a large-scale conjugated system with a non-planar structure.
  • the nitrogen-containing compound of the present application protects the nitrogen atom with high chemical activity in the structure, thereby improving the stability of the material;
  • This type of compound with a planar structure has low intermolecular forces, so that the compound has low sublimation temperature and evaporation temperature.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.
  • FIG. 3 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
  • FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
  • Example embodiments will now be described more fully with reference to the accompanying drawings.
  • Example embodiments can be embodied in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art.
  • the described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided in order to give a thorough understanding of the embodiments of the present application.
  • the present application provides a nitrogen-containing compound, and the structure of the nitrogen-containing compound is shown in formula 1:
  • B 1 and B 2 are the same or different from each other, and are each independently selected from the groups represented by Formula 1-1, Formula 1-2 or Formula 1-3, and B 1 and B 2 are not the same as Formula 1-1 and Formula 1-3.
  • Ar 1 , Ar 2 , Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms in total, substituted or unsubstituted aryl groups having 3-30 carbon atoms in total Heteroaryl;
  • L 1 is selected from a substituted or unsubstituted arylene group with a total carbon number of 6-20, a substituted or unsubstituted heteroarylene group with a total carbon number of 4-15;
  • L 2 and L 3 are the same or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6-20, a substituted or unsubstituted group with a total carbon number of 4-15 the heteroarylene;
  • R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, carbon atom Alkenyl group with 2-6 carbon atoms, cycloalkyl group with carbon number of 3-10, group A, heteroaryl group with carbon number of 3-20, alkoxy group with carbon number of 1-10, carbon Alkylthio group with 1-10 atoms or trialkylsilyl group with 3-12 carbon atoms; group A is selected from substituted or unsubstituted aryl groups with total carbon number of 6-20, among the aryl groups The substituents are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-4 carbon atoms, haloalkyl group with carbon number of 1-4, cycloalkyl group with carbon number of 3-10 or trialkylsilyl with 3-7 carbon atoms;
  • n 1 is the number of substituent R 1 , n 1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when n 1 is greater than 1, any two R 1 are the same or different, optionally, Any two adjacent R 1 form a ring;
  • n 2 is the number of substituent R 2 , n 2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, when n 2 is greater than 1, any two R 2 are the same or different, optionally, any two adjacent R 2 form a ring;
  • the substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3- Heteroaryl of 18, alkyl of 1-10 carbon atoms, haloalkyl of 1-10 of carbon atoms, cycloalkyl of 3-10 of carbon atoms, alkoxy of 1-10 of carbon atoms base, alkylthio group with 1-10 carbon atoms or trialkylsilyl group with 3-12 carbon atoms;
  • the substituents in L 1 , L 2 and L 3 are the same or different, and each is independently selected from: deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, 3- Heteroaryl with 12, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms base, alkylthio group with 1-10 carbon atoms or trialkylsilyl group with 3-12 carbon atoms;
  • any two adjacent substituents form a ring;
  • B 1 and B 2 are not simultaneously When the structure is selected from formula 1-3 B 1, and L 3 is a substituted or unsubstituted 1,4-phenylene, B 2 and B 1 different from the structure.
  • the nitrogen-containing compound of the present application uses 1,8-disubstituted naphthalene as the core structure, and combines triarylamine and/or carbazole structure-containing group in a specific way as the substituent group of 1,8-disubstituted naphthalene
  • triarylamines and carbazole-like groups with strong hole transport properties are stacked face-to-face at close distances in space, thus forming a large-scale conjugated system with a non-planar structure.
  • the nitrogen-containing compound of the present application protects the nitrogen atom with high chemical activity in the structure, thereby improving the stability of the material;
  • This type of compound with a planar structure has lower intermolecular forces, so that the compound has a low sublimation and evaporation temperature.
  • B 1 and B 2 are not the combination of formula 1-1 and formula 1-3, which means that when one of B 1 and B 2 is represented by formula 1-1 When the group of , the other one cannot be the formula 1-3, but the other one can be selected from the group represented by the formula 1-1 or the formula 1-2, for example.
  • the total number of carbon atoms of a substituted group refers to the number of all carbon atoms. For example, if Ar 1 is selected from a substituted aryl group with a total carbon number of 20, then all carbon atoms of the aryl group and the substituents thereon are 20.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can either refer to In different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other.
  • each q" is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is:
  • formula Q-1 represents that there are q" substituents on the benzene ring R", each R" can be the same or different, and the options of each R" do not affect each other;
  • formula Q-2 means that each benzene ring of biphenyl has q" substituents R", two benzene rings The number q" of R" substituents can be the same or different, each R" can be the same or different, and the options of each R" do not affect each other.
  • any two adjacent R 1 form a ring;
  • any two adjacent R 1 can form a ring but need not form a ring, including: any two adjacent R 1 form a ring and any two adjacent R 1 do not form a ring.
  • references to adjacent groups "forming a ring” include: adjacent groups may be joined by a single bond to form a ring together with the atoms to which they are commonly joined, or adjacent groups may be fused together with the atoms to which they are joined to form a ring .
  • the ring formed by adjacent groups may be, for example, a 5- to 13-membered saturated or unsaturated ring.
  • the ring formed by the adjacent group and the atoms that are connected together can be, for example, fluorene ring, cyclohexane or cyclopentane
  • the ring formed by the condensing of adjacent groups and the atoms to which they are connected can be, for example, a benzene ring. , Naphthalene ring.
  • an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
  • Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation.
  • two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application.
  • the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like.
  • the aryl group does not contain heteroatoms such as B, N, O, S, P and Si.
  • a biphenyl group and a 9, 9- dimethyl fluorenyl group are regarded as an aryl group.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene base, base, spirobifluorenyl, etc.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • a substituted aryl group may be one or two or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothienyl-substituted phenyl groups, pyridyl-substituted pheny
  • the total number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group.
  • any two adjacent substituents can form a ring, for example, through a single bond, or can be fused to form a ring.
  • a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be at least one of B, O, N, P, Si and S.
  • a heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic
  • the ring system is an aromatic monocyclic ring or an aromatic fused ring.
  • heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thieny
  • heteroarylene group refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be one or more than two hydrogen atoms in the heteroaryl group replaced by a group such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups.
  • aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like.
  • the total number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
  • any two adjacent substituents can form a ring, for example, through a single bond, or can be fused to form a ring.
  • the number of ring-forming carbon atoms refers to the number of carbon atoms located on an aromatic ring (aromatic ring, heteroaromatic ring).
  • aromatic ring aromatic ring, heteroaromatic ring
  • the number of ring carbon atoms of phenyl is 6, the number of ring carbon atoms of naphthyl is 10, the number of ring carbon atoms of biphenyl is 12, and the number of ring carbon atoms of dibenzofuranyl is 12, N-phenylcarbazolyl has 18 ring carbon atoms.
  • the number of carbon atoms of the aryl group and the heteroaryl group as the substituent is also considered in the number of ring carbon atoms, for example, The number of ring carbon atoms is 25, The number of ring carbon atoms is 18.
  • a non-positioned connecting bond refers to a single bond extending from the ring system It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule.
  • the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two non-positioned linkages running through the bicyclic ring. -1) to any possible connection method shown in formula (f-10).
  • the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, which represents The meaning of , includes any possible connection modes shown by formula (X'-1) to formula (X'-4).
  • a non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system.
  • the substituent R' represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings represented by the formula (Y-1) to Any possible connection method shown in formula (Y-7):
  • a cycloalkyl group having 3-10 carbon atoms can be used as a substituent for an aryl group and a heteroaryl group, and specific examples thereof include but are not limited to cyclopentyl, cyclohexyl, adamantyl and the like.
  • alkyl groups with 1-10 carbon atoms include straight-chain alkyl groups with 1-10 carbon atoms and branched-chain alkyl groups with 3-10 carbon atoms, and the number of carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, the specific implementation of alkyl may include but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n- Amyl, n-hexyl, n-heptyl, n-octyl, etc.
  • halogen includes fluorine, chlorine, bromine, and iodine.
  • the number of carbon atoms of an alkoxy group having 1 to 10 carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
  • Specific examples of the alkoxy group include but Not limited to, methoxy, ethoxy, n-propoxy and the like.
  • the number of carbon atoms of an aryl group having 6 to 20 carbon atoms may be, for example, 6 (for example, phenyl), 10 (for example, naphthalene), 12 (for example, biphenyl), 15 (9 , 9-dimethylfluorenyl), 18 (such as terphenyl) and the like.
  • Specific examples of the aryl group having 6 to 12 carbon atoms include, but are not limited to, phenyl, naphthyl, biphenyl.
  • the haloalkyl group may be, for example, a fluoroalkyl group, and the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and specific examples include but are not limited to trifluoromethyl base.
  • trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • the structure of the nitrogen-containing compound can be as shown in Formula 11,
  • B 2 is selected from formula 1-1, formula 1-2 or formula 1-3.
  • the nitrogen-containing compound may be selected from the group consisting of the following formulae A to E:
  • the two Ar 1 may be the same or different, and the two Ar 2 may also be the same or different.
  • the two Ar 3 s may be the same or different, the two L 2 s may be the same or different, and the multiple R 1 s and n 1 s that exist may also be the same or different.
  • the two L 3 s may be the same or different, and the plurality of R 2 and n 2 present may be the same or different, respectively.
  • formula A two not at the same time
  • one of L 3 is a substituted or unsubstituted 1,4-phenylene (the structure of 1,4-phenylene)
  • two The specific structure is different.
  • Ar 2 can be selected from substituted or unsubstituted aryl groups with a total carbon number of 7-30, substituted or unsubstituted heteroaryl groups with a total carbon number of 3-30.
  • the number of carbon atoms can be 7, 8, 9, 10, 11, 12, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30;
  • the carbon atom Numbers can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 , 21, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30.
  • R 1 and R 2 are the same or different from each other, and each is independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, and 1-4 carbon atoms haloalkyl, cycloalkyl with 5-10 carbon atoms, group B, heteroaryl with 3-18 carbon atoms, alkoxy with 1-4 carbon atoms, 1- An alkylthio group of 4 or a trialkylsilyl group of 3-7 carbon atoms.
  • the group B is selected from substituted or unsubstituted aryl groups with a total carbon number of 6-15, and the substituents in the aryl group are independently selected from deuterium, fluorine, cyano, and 1-4 carbon atoms.
  • R 1 , R 2 are each independently selected from: deuterium, fluorine, cyano, methyl, tert-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, adamantyl, Phenyl, naphthyl, biphenyl, phenyl substituted with trifluoromethyl, methyl, tert-butyl, cyano, fluorine or deuterium, and the like.
  • any two adjacent R 1 can be fused to form a ring, such as a benzene ring.
  • any two adjacent R 2 can be fused to form a ring, such as a benzene ring.
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are independently selected from substituted or unsubstituted aryl groups with a total carbon number of 6-25, a total carbon number of 5 -25 substituted or unsubstituted heteroaryl.
  • the substituents in Ar 1 , Ar 2 , Ar 3 are each independently selected from: deuterium, fluorine, cyano, aryl with 6-15 carbon atoms, and heteroaryl with 5-12 carbon atoms base, alkyl group having 1-4 carbon atoms, haloalkyl group having 1-4 carbon atoms, cycloalkyl group having 5-10 carbon atoms, alkoxy group having 1-4 carbon atoms, carbon atom Alkylthio group with 1-4 number or trialkylsilyl group with 3-7 carbon atoms.
  • any two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
  • the substituents in Ar 1 , Ar 2 , Ar 3 are each independently selected from: deuterium, fluorine, cyano, phenyl, naphthyl, biphenyl, phenanthrenyl, anthracenyl, dimethylfluorenyl , pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, Adamantyl, trimethylsilyl, methylthio, methylthio.
  • any two adjacent substituents form a fluorene ring, cyclopentane or cyclohexane.
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups with 6-25 ring carbon atoms, 5-25 ring carbon atoms. Substituted or unsubstituted heteroaryl. Wherein, the number of ring carbon atoms of the substituted or unsubstituted aryl group is, for example, 6, 10, 12, 13, 18, 21, 25, etc., and the number of ring carbon atoms of the substituted or unsubstituted heteroaryl group is, for example, 5, 6, 7, 8, 9, 10, 12, 18, 20, 24, 25, etc.
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are each independently selected from the group consisting of groups represented by formula i-1 to formula i-15:
  • M 1 is selected from 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;
  • H 1 is selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl with 3 to 12 carbon atoms, alkyl with 1 to 10 carbon atoms, and 1 to 10 carbon atoms haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms or alkylthio group with 1-10 carbon atoms;
  • H 2 to H 9 and H 22 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms. group, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, or carbon Heteroaryl with 3 to 18 atoms;
  • H 10 to H 21 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 12 carbon atoms.
  • h 1 to h 22 are represented by h k
  • H 1 to H 22 are represented by H k
  • k is a variable, representing any integer from 1 to 22
  • h k represents the number of substituents H k ; wherein, 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, 21 or 22, h k is selected from 1, 2, 3 or 4; when 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 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 H k are the same
  • K 1 is selected from O, S, Se, N(H 23 ), C(H 24 H 25 ), Si(H 24 H 25 ); wherein, H 23 , H 24 and H 25 are each independently selected from: carbon atom Aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, or the above H 24 and H 25 are connected to each other to form a saturated or unsaturated ring of 5-13 members together with the atoms they are commonly connected to;
  • K 2 is selected from single bond, O, S, Se, N(H 26 ), C(H 27 H 28 ), Si(H 27 H 28 ); wherein, H 26 , H 27 , H 28 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, a cycloalkyl group having 3 to 10 carbon atoms, or the above H 27 and H 28 are connected to each other to form a 5- to 13-membered saturated or unsaturated ring together with the atoms to which they are commonly connected;
  • K 3 represents O or S.
  • the ring formed by the interconnection of the two groups in each group may be a 5-13 membered saturated or unsaturated ring.
  • the ring formed by the interconnection of the two groups in each group may be a 5-13 membered saturated aliphatic ring or an aromatic ring.
  • the above-mentioned two groups of H 24 and H 25 , and the above-mentioned H 27 and H 28 can respectively form a 5-8-membered saturated aliphatic monocyclic ring or a 10-13-membered aromatic ring.
  • F 2 to F 4 can be represented by F j , wherein j is a variable, representing 2, 3 or 4.
  • j is a variable, representing 2, 3 or 4.
  • J j refers to J 2 .
  • F j C (F j) does not exist.
  • G 12 when When connected to G 12 , G 12 can only represent a C atom, that is, the structure of formula i-13 is specifically:
  • formula j-4 involving L 1 to L 3
  • Q represents a C atom.
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted group Z, wherein the unsubstituted group Z is selected from the group consisting of:
  • the substituted group Z has one or more substituents, and the substituents are independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, and ring with 5-10 carbon atoms. Alkyl, haloalkyl with 1-4 carbon atoms, trialkylsilyl with 3-7 carbon atoms; when the number of substituents is more than 1, the substituents are the same or different.
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and are each independently selected from the group consisting of:
  • Ar 1 , Ar 2 and Ar 3 are the same or different from each other, and each is independently selected from the group consisting of the following groups:
  • L 1 and L 3 are the same or different from each other, and are independently selected from substituted or unsubstituted arylene groups with a total carbon number of 6-12, a total carbon number of 5-12 substituted or unsubstituted heteroarylene.
  • L 1 and L 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups with 6-12 ring carbon atoms, and substituted or unsubstituted aryl groups with 5-12 ring carbon atoms. or unsubstituted heteroaryl.
  • the number of ring carbon atoms of the substituted or unsubstituted aryl group is, for example, 6, 10, 12, etc.
  • the number of ring carbon atoms of the substituted or unsubstituted heteroaryl group is, for example, 5, 6, 7, 8, 9, 10, 12.
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6-12, and a substituted or unsubstituted heteroarylene group with a total carbon number of 5-12.
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 6-12 ring carbon atoms, a substituted or unsubstituted heteroarylene group with 5-12 ring carbon atoms .
  • the number of ring carbon atoms of the substituted or unsubstituted arylene group is, for example, 6, 10, 12, etc.
  • the number of ring carbon atoms of the substituted or unsubstituted heteroarylene group is, for example, 5, 6, 7, 8, 9, 10, 12, etc.
  • the substituents in L 1 , L 2 and L 3 are the same or different, and each is independently selected from: deuterium, fluorine, cyano, phenyl, pyridyl, and alkyl groups with 1-4 carbon atoms , a halogenated alkyl group with 1-4 carbon atoms or a trialkylsilyl group with 3-7 carbon atoms.
  • the substituents in L 1 , L 2 , and L 3 are each independently selected from: deuterium, fluorine, cyano, phenyl, pyridyl, methyl, ethyl, isopropyl, tert-butyl, Trifluoromethyl or trimethylsilyl.
  • L 1 , L 2 and L 3 are the same or different from each other, and are each independently selected from the group consisting of groups represented by formula j-1 to formula j-4 below:
  • M 2 is selected from single bond or
  • Q 1 to Q 5 are each independently selected from N or C(F 4 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from C(F 4 ) , any two F 4 are the same or different;
  • E 1 to E 5 and F 4 are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, Trialkylsilyl group with 3 to 12 carbon atoms, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, carbon atom an alkoxy group with 1 to 10 carbon atoms or an alkylthio group with 1 to 10 carbon atoms;
  • E 1 ⁇ E 5 to E r represents, E 1 to E 5 to E r, where r represents the variable and is selected from any integer from 1 to 5; when r is selected from 2, 3 or 5, E r is selected from 1, 2, 3 or 4; when r is 4, er is selected from 1, 2, 3 , 4, 5 or 6; and when er is greater than 1, any two Er are the same or different.
  • L 1 , L 2 and L 3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the group consisting of:
  • the substituted group V has one or more substituents, and the substituents are independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, and ring with 5-10 carbon atoms.
  • substituents are independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, and ring with 5-10 carbon atoms.
  • alkyl, haloalkyl with 1-4 carbon atoms, and trialkylsilyl group with 3-7 carbon atoms when the number of substituents is more than 1, the substituents are the same or different.
  • L 1 , L 2 and L 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene , substituted or unsubstituted naphthylene, the substituent is phenyl.
  • L 1 , L 2 and L 3 are the same or different from each other, and are each independently selected from the group consisting of:
  • the structure of the nitrogen-containing compound is shown in formula A or formula D.
  • the nitrogen-containing compound can be used as a hole transport layer material of an electronic component, such as a first hole transport layer material and/or a second hole transport layer (also called electron blocking layer) of an organic electroluminescence device. layer) material.
  • Ar 1 , Ar 2 , Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having a total carbon number of 6-25, substituted or unsubstituted aryl groups having a total carbon number of 5-20, or Unsubstituted Heteroaryl.
  • L 1 is selected from a substituted or unsubstituted arylene group with a total carbon number of 6-12;
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6-12.
  • the structure of the nitrogen-containing compound is shown in formula B, formula C or formula E.
  • the nitrogen-containing compound can be used as a light-emitting layer material of an electronic component, such as a light-emitting layer host material of an electroluminescent device.
  • Ar 3 is selected from a substituted or unsubstituted aryl group with a total carbon number of 6-20, a substituted or unsubstituted heteroaryl group with a total carbon number of 5-20.
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with a total carbon number of 6-12.
  • L 3 is selected from substituted or unsubstituted arylene groups with a total carbon number of 6-12.
  • the structure of the nitrogen-containing compound is shown in formula A.
  • Ar 1 is selected from substituted or unsubstituted aryl groups with ring carbon atoms of 6-20
  • Ar 2 is selected from substituted or unsubstituted aryl groups with ring carbon atoms of 10-25, ring carbon atoms A substituted or unsubstituted heteroaryl group having 7-20 atoms.
  • the nitrogen-containing compound can further improve the overall performance of the device, especially the lifetime of the device.
  • the structure of the nitrogen-containing compound is shown in formula C.
  • at least one L 3 is selected from a substituted or unsubstituted arylene group having 10-20 ring carbon atoms.
  • the nitrogen-containing compound can further improve the overall performance of the device, especially the lifetime of the device.
  • the nitrogen-containing compound is selected from the group consisting of:
  • the present application does not specifically limit the synthesis method of the nitrogen-containing compound provided, and those skilled in the art can determine a suitable synthesis method according to the preparation method provided in the synthesis example section of the present application for the nitrogen-containing compound.
  • the synthesis examples section of the present invention exemplarily provides a method for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art.
  • Those skilled in the art can obtain all nitrogen-containing compounds provided in the present application according to these exemplary preparation methods, and all specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here, and those skilled in the art should not interpret it as a limit.
  • the present application also provides an electronic component, the electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer includes the nitrogen-containing compound of the present application.
  • the electronic component may be an organic electroluminescent device or a photoelectric conversion device.
  • the functional layer includes a hole transport layer, and the hole transport layer may be one layer or more than two layers.
  • the functional layer includes a light-emitting layer, and the light-emitting layer includes a host material and a guest material.
  • the hole transport layer may include the nitrogen-containing compound.
  • the host material of the light-emitting layer includes the nitrogen-containing compound.
  • the nitrogen-containing compound provided in the present application can be applied to the hole transport layer of an organic electroluminescent device or as the host material of the light-emitting layer, and can improve the luminous efficiency and lifespan of the organic electroluminescent device under the condition of ensuring a lower driving voltage .
  • the organic electroluminescence device may be a red light device, a blue light device or a green light device.
  • the electronic component is an organic electroluminescence device.
  • the organic electroluminescent device may include an anode 100 , a hole transport layer 320 , a light-emitting layer 330 serving as an energy conversion layer, an electron transport layer 340 and a cathode 200 , which are stacked in sequence, wherein the hole transport layer 320 A first hole transport layer 321 and a second hole transport layer 322 are included. As shown, the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322 .
  • the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
  • anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (the IZO); a combination of metal and oxides such as ZnO: Al or SnO 2: Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2- oxy)thiophene] (PEDT), polypyrrole and polyaniline. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the hole transport layer 320 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.
  • the nitrogen-containing compound provided in the present application can be applied to the first hole transport layer 321 and/or the second hole transport layer 322 of the organic electroluminescence device.
  • one of the first hole transport layer 321 and the second hole transport layer 322 includes the compound of the present application, and the other may be composed of the compound HT-02 or HT-01.
  • the light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the light-emitting layer 330 is composed of a host material and a guest material.
  • the holes injected into the light-emitting layer 330 and the electrons injected into the light-emitting layer 330 can recombine in the light-emitting layer 330 to form excitons, and the excitons transfer energy to the light-emitting layer 330.
  • Host material the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the light-emitting layer 330 may be a metal chelate compound, a bis-styryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials.
  • the guest material of the light-emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials.
  • the host material of the light-emitting layer 330 includes BH-01, and the guest material includes BD-01.
  • the host material of the light-emitting layer 330 includes the compound of the present application.
  • the host material of the light emitting layer 330 includes the nitrogen-containing compound of the present application and GH-n1, and the guest material includes Ir(ppy) 3 .
  • the electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives , quinoxaline derivatives or other electron transport materials.
  • the electron transport layer 340 may be composed of ET-01 and LiQ.
  • the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al , Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
  • a metal electrode containing magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting holes into the hole transport layer.
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in this application.
  • the hole injection layer 310 may be composed of F4-TCNQ.
  • an electron injection layer 350 may also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 .
  • the electron injection layer 350 may include inorganic materials such as alkali metal sulfide, alkali metal halide, Yb, or the like, or may include a complex compound of alkali metal and organic matter.
  • the electron injection layer 350 may include LiQ.
  • the hole injection layer 310 , the first hole transport layer 321 , the second hole transport layer 322 , the light emitting layer 330 , the electron transport layer 340 and the electron injection layer 350 constitute the functional layer 300 .
  • 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 a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application.
  • the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.
  • the hole transport layer 320 may further include an inorganic dopant material to improve the hole transport performance of the hole transport layer 320 .
  • the photoelectric conversion device may include an anode 100 , a hole transport layer 320 , a photoelectric conversion layer 360 , an electron transport layer 340 and a cathode 200 which are stacked in sequence.
  • the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell.
  • a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode that are stacked in sequence, wherein the hole transport layer includes the Nitrogenous compounds.
  • the present application also provides an electronic device, which includes the above-mentioned electronic components.
  • the electronic device is a first electronic device 400
  • the first electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like.
  • the electronic device is a second electronic device 500
  • the second electronic device 500 includes the above-mentioned photoelectric conversion device.
  • the second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices.
  • Reactants used to synthesize the compounds of the present application may include intermediates IM 1-I, IM 2-I and IM 3-I whose structures are shown below;
  • the above-mentioned reactants can be obtained commercially; they can also be obtained by methods well known in the art, for example, reference can be made to the literature KR1020140082486A, WO2014081206A1, WO2012015274A2 for synthesis, and the specific methods for synthesizing the above-mentioned reactants are well known in the art, and will not be repeated here. .
  • the IM 1-1 employed includes the following intermediates IM 1-1 to IM 1-9:
  • IM 2-1 include the following IM 2-1 to IM 2-11:
  • IM 3-1 include IM 3-1 to IM 3-4:
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. Ultraviolet ozone and O 2 :N 2 plasma were used for 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 compound A1 is evaporated on the hole injection layer to form a thickness of The first hole transport layer (HTL1).
  • HIL hole injection layer
  • HTL1 The first hole transport layer
  • Compound HT-02 was vacuum evaporated on the first hole transport layer to form a thickness of The second hole transport layer (HTL2).
  • BH-01:BD-01 was co-evaporated at the evaporation rate ratio of 98%:2% to form a thickness of The blue light-emitting layer (EML).
  • ET-01 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above-mentioned cathode is The CP-01 is formed to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
  • CPL organic capping layer
  • An organic electroluminescence device was fabricated by the same method as in Example 1, except that the compounds shown in Table 4 below were substituted for Compound A1 in forming the first hole transport layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that HT-01 and Compound a were used instead of Compound A1 in Comparative Example 1 and Comparative Example 2, respectively, when forming the first hole transport layer.
  • Example 2 The same method as in Example 1 was used except that compound HT-01 was used instead of compound A1 when the first hole transport layer was formed, and HT-02 was replaced by the compounds in Table 4 when the second hole transport layer was formed.
  • the method fabricates an organic electroluminescent device.
  • the optoelectronic properties of the device were analyzed under the condition of 10 mA/cm 2 , and the lifetime performance of the device was analyzed under the condition of 20 mA/cm 2 .
  • the results are shown in Table 4.
  • the anode is prepared by the following process: the thickness is The ITO substrate (manufactured by Corning) was cut into a size of 40mm ⁇ 40mm ⁇ 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. Ultraviolet ozone and O 2 :N 2 plasma were used for Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.
  • F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a thickness of The hole injection layer (HIL), and HT-01 was evaporated on the hole injection layer to form a thickness of the first hole transport layer.
  • HIL hole injection layer
  • HT-02 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • compound B1:GH-n1:Ir(ppy) 3 was co-evaporated at the ratio of evaporation rate of 50%:45%:5% to form a thickness of green emissive layer (EML).
  • EML green emissive layer
  • ET-01 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), LiQ was evaporated on the electron transport layer to form a thickness of The electron injection layer (EIL) of the the cathode.
  • ETL Thick electron transport layer
  • EIL electron injection layer
  • the thickness of the vapor deposition on the above-mentioned cathode is The CP-01 is formed to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.
  • CPL organic capping layer
  • Organic electroluminescence was produced by the same method as in Example 12, except that the compounds shown in Table 5 below were substituted for Compound B1 in forming the light-emitting layer (Compound B1 and compounds in place of B1 are collectively referred to as EM1 compounds in Table 5) device.
  • Organic electroluminescent devices were fabricated by the same method as in Example 12, except that Compound C and Compound d were used instead of Compound B1 in Comparative Examples 4 and 5, respectively, when forming the light-emitting layer.
  • the optoelectronic properties of the device were analyzed under the condition of 10mA/cm 2
  • the lifetime performance of the device was analyzed under the condition of 20mA/cm 2 , and the results are shown in the following table:
  • the nitrogen-containing compound of the present application when used to prepare a green organic electroluminescent device, it can effectively prolong the life of the organic electroluminescent device, and has both high luminous efficiency and low 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式（1）所示。所述含氮化合物应用于有机电致发光器件中时，可以在维持器件发光效率的同时，有效提升器件寿命。

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7月9日递交的申请号为202010659195.6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，具体涉及一种含氮化合物、包括该含氮化合物的电子元件和包括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。
以有机电致发光器件为例，其一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
现有技术中，JP2012167058A公开了一种以1,8-二取代萘为基础结构的发光层材料；KR1020150006374A公开了一种以二取代萘为连接基团的空穴传输层材料。然而，该类型材料结构以及性能表现仍然具有很大的改进空间。
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、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：
本申请的第一方面提供一种含氮化合物，所述含氮化合物的结构如式1所示：
Figure PCTCN2021105331-appb-000001
B 1、B 2彼此相同或不同，且各自独立地选自式1-1、式1-2或式1-3所示的基团，且B 1、B 2不为式1-1和式1-3的组合：
Figure PCTCN2021105331-appb-000002
其中，
Figure PCTCN2021105331-appb-000003
表示化学键；
Ar 1、Ar 2、Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-30的取代或未取代的芳基、总碳原子数为3-30的取代或未取代的杂芳基；
L 1选自总碳原子数为6-20的取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
L 2、L 3彼此相同或不同，且各自独立地选自单键、总碳原子数为6-20的取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
R 1、R 2彼此相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为1-10的烷基、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3-10的环烷基、基团A、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的烷硫基或碳原子数为3-12的三烷基硅基；基团A选自总碳原子数为6-20的取代或未取代的芳基，芳基中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基、碳原子数为3-10的环烷基或碳原子数为3-7的三烷基硅基；
n 1为取代基R 1的数量，n 1选自0、1、2、3、4、5、6或7，当n 1大于1时，任意两个R 1相同或不同，任选地，任意两个相邻的R 1形成环；n 2为取代基R 2的数，n 2选自0、1、2、3、4、5、6、7或8，当n 2大于1时，任意两个R 2相同或不同，任选地，任意两个相邻的R 2形成环；
Ar 1、Ar 2、Ar 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-20的芳基、碳原子数为3-18的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
L 1、L 2、L 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
任选地，Ar 1、Ar 2、Ar 3、L 1、L 2和L 3的取代基中，任意两个相邻的取代基形成环；
并且，
B 1、B 2不同时为
Figure PCTCN2021105331-appb-000004
当B 1选自式1-3结构，且L 3为取代或未取代的1,4-亚苯基时，B 2的结构与B 1不同。
本申请的第二方面提供一种电子元件，该电子元件包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；其中，所述功能层包含第一方面所述的含氮化合物。
本申请的第三方面提供一种电子装置，该电子装置包括第二方面所述的电子元件。
本申请的含氮化合物以1,8-二取代萘作为核心结构，将三芳基胺和/或包括咔唑类结构的基团以特定方式进行组合，作为1,8-二取代萘的取代基团；在该结构的化合物中，具有强的空穴传输性能的三芳基胺和咔唑类基团，在空间上近距离面对面堆叠，从而组成了具有非平面结构的大型共轭体系。本申请的含氮化合物在保障材料的载流子迁移率和合适的分子轨道能级的前提下，保护了结构中具有高化学活性的氮原子，从而提升材料的稳定性；同时，由于具有非平面结构的该类型化合物具有较低的分子间作用力，从而使该化合物具有低的升华温度和蒸镀温度。将该类化合物应用于有机电致发光器件中时，可以在维持器件发光效率的同时，有效提升器件寿命。
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是本申请一种实施方式的第一电子装置的结构示意图。
图4是本申请一种实施方式的第二电子装置的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；320：空穴传输层；321、第一空穴传输层；322、第二空穴传输层；330、发光层；340、电子传输层；350、电子注入层；360、光电转化层；400、第一电子装置；500、第二电子装置。
具体实施方式
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，该含氮化合物的结构如式1所示：
Figure PCTCN2021105331-appb-000005
B 1、B 2彼此相同或不同，且各自独立地选自式1-1、式1-2或式1-3所示的基团，且B 1、B 2不为式1-1和式1-3的组合：
Figure PCTCN2021105331-appb-000006
其中，
Figure PCTCN2021105331-appb-000007
表示化学键。
Ar 1、Ar 2、Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-30的取代或未取代的芳基、总碳原子数为3-30的取代或未取代的杂芳基；
L 1选自总碳原子数为6-20取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
L 2、L 3彼此相同或不同，且各自独立地选自单键、总碳原子数为6-20的取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
R 1、R 2彼此相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为1-10的烷基、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3-10的环烷基、基团A、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的烷硫基或碳原子数为3-12的三烷基硅基；基团A选自总碳原子数为6-20的取代或未取代的芳基，芳基中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基、碳原子数为3-10的环烷基或碳原子数为3-7的三烷基硅基；
n 1为取代基R 1的数量，n 1选自0、1、2、3、4、5、6或7，当n 1大于1时，任意两个R 1相同或不同，任选地，任意两个相邻的R 1形成环；n 2为取代基R 2的数，n 2选自0、1、2、3、4、5、6、7或8，当n 2大于1时，任意两个R 2相同或不同，任选地，任意两个相邻的R 2形成环；
Ar 1、Ar 2、Ar 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-20的芳基、碳原子数为3-18的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
L 1、L 2、L 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
任选地，Ar 1、Ar 2、Ar 3、L 1、L 2和L 3的取代基中，任意两个相邻的取代基形成环；
并且，
B 1、B 2不同时为
Figure PCTCN2021105331-appb-000008
当B 1选自式1-3结构，且L 3为取代或未取代的1,4-亚苯基时，B 2的结构与B 1不同。
本申请的含氮化合物以1,8-二取代萘作为核心结构，将三芳基胺和/或含咔唑结构的基团以特定方式进行组合，作为1,8-二取代萘的取代基团；在该结构的化合物中，具有强的空穴传输性能的三芳基胺和咔唑类基团，在空间上近距离面对面堆叠，从而组成了具有非平面结构的大型共轭体系。本申请的含氮化合物在保障材料的载流子迁移率和合适的分子轨道能级的前提下，保护了结构中具有高化学活性的氮原子，从而提升材料的稳定性；同时，由于具有非平面结构的该类型化合物具有较低的分子间作用力，从而使该化合物具有低的升华和蒸镀温度。将该类化合物应用于有机电致发光器件中时，可以在维持器件发光效率的同时，有效提升器件寿命。
为了实现本申请的发明目的，式1中，B 1、B 2不为式1-1和式1-3的组合，其是指当B 1、B 2中一者为式1-1所示的基团时，另一者不能为式1-3，但另一者例如可以选自式1-1或式1-2所示的基团。
在本申请中，取代的基团的总碳原子数，指的是所有碳原子数。举例而言，若Ar 1选自总碳原子数为20的取代的的芳基，则芳基及其上的取代基的所有碳原子数为20。
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 PCTCN2021105331-appb-000009
其中，各q”独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q”个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q”个取代基R”，两个苯环上的R”取代基的个数q”可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，术语“任选”或“任选地”意味着随后所描述的事件或者环境可以但不必发生，该说明包括该事情或者环境发生或者不发生的场合。例如，“任选地，任意两个相邻的R 1形成环；”意味着任意两个相邻的R 1可以形成环但不是必须形成环，包括：任意两个相邻的R 1形成环的情景和任意两个相邻的R 1不形成环的情景。
所涉及的相邻基团“形成环”包括：相邻基团之间可通过单键连接以与其共同连接的原子一起形成环，或者是相邻基团与各自连接的原子一起稠合形成环。相邻基团形成的环例如可以为5～13元的饱和或不饱和环。其中，相邻基团与其共同连接的原子一起形成的环，例如可以为芴环、环己烷或环戊烷，相邻基团与各自连接的原子一起稠合形成的环例如可以为苯环、萘环。
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合 芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P和Si等杂原子。需要说明的是，在本申请中，联苯基、9,9-二甲基芴基均视为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021105331-appb-000010
基、螺二芴基等。本申请中，涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩基取代的苯基、吡啶基取代的苯基等。应当理解地是，取代的芳基的总碳原子数，指的是芳基和芳基上的取代基的碳原子总数。任选地，任意两个相邻的取代基可形成环，例如可通过单键成环，也可稠合形成环。
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-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等，而不限于此。其中，噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基，N-苯基咔唑基、N-吡啶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。另外，苯并呋喃基、苯并吡啶基等属于双环稠合杂芳基，二苯并呋喃基、二苯并噻吩基、咔唑基等属于三环稠合杂芳基。本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
在本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、-CN、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。应当理解地是，取代的杂芳基的总碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。任选地，任意两个相邻的取代基可形成环，例如可通过单键成环，也可稠合形成环。
在本申请中，成环碳原子数是指位于芳香环(芳环、杂芳环)上的碳原子数。举例来讲，苯基的成环碳原子数为6，萘基的成环碳原子数为10，联苯基的成环碳原子数为12，二苯并呋喃基的成环碳原子数为12，N-苯基咔唑基的成环碳原子数为18。需要说明地是，本申请中，作为取代基的芳基、杂芳基的碳原子数也被考虑在成环碳原子数中，例如，
Figure PCTCN2021105331-appb-000011
的成环碳原子数为25，
Figure PCTCN2021105331-appb-000012
的成环碳原子数为18。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021105331-appb-000013
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。
举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式。
Figure PCTCN2021105331-appb-000014
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 PCTCN2021105331-appb-000015
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 PCTCN2021105331-appb-000016
本申请中，碳原子数为3-10的环烷基可以作为芳基、杂芳基的取代基，其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，碳原子数为1-10的烷基包括碳原子数为1-10的直链烷基和碳原子数为3-10的支链烷基，碳原子数可以为1、2、3、4、5、6、7、8、9、10，烷基的具体实施可以包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、叔丁基、正戊基、正己基、正庚基、正辛基等。
本申请中，卤素包括氟、氯、溴、碘。
本申请中，碳原子数为1-10的烷氧基的碳原子数例如可以为1、2、3、4、5、6、7、8、9或10，烷氧基的具体实例包括但不限于，甲氧基、乙氧基、正丙氧基等。
本申请中，碳原子数为6-20的芳基的碳原子数例如可以分别为6(例如为苯基)、10(例如为 萘)、12(例如为二联苯基)、15(9,9-二甲基芴基)、18(例如三联苯基)等。碳原子数为6-12的芳基的具体实例包括但不限于苯基、萘基、二联苯基。
在本申请中，卤代烷基例如可以为氟代烷基，碳原子数例如可以为1、2、3、4、5、6、7、8、9或10，具体实例包括但不限于三氟甲基。
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。
在一些实施方式中，所述含氮化合物的结构可以如式11所示，
Figure PCTCN2021105331-appb-000017
其中，B 2的结构选自式1-1、式1-2或式1-3。
在本申请中，所述含氮化合物可以选自如下式A至式E所组成的组：
Figure PCTCN2021105331-appb-000018
式A中，两个Ar 1可以相同或不同，两个Ar 2也可以相同或不同。式B中，两个Ar 3可以相同或不同，两个L 2可以相同或不同，存在的多个R 1、n 1也可以相同或不同。式C中，两个L 3可以相同或不同，存在的多个R 2、n 2也可以分别相同或不同。为了实现本申请的发明目的，式A中，两个
Figure PCTCN2021105331-appb-000019
不同时为
Figure PCTCN2021105331-appb-000020
式C中，当其中一个L 3为取代或未取代的1,4-亚苯基(1,4-亚苯基的结构
Figure PCTCN2021105331-appb-000021
)时，两个
Figure PCTCN2021105331-appb-000022
的具体结构不同。
在一种示例性的实施方式中，式A中，两个
Figure PCTCN2021105331-appb-000023
中，其中一个
Figure PCTCN2021105331-appb-000024
可以为
Figure PCTCN2021105331-appb-000025
另一个
Figure PCTCN2021105331-appb-000026
中，Ar 2可以选自总碳原子数为7-30的取代或未取代的芳基、总碳原子数为3-30的取代或未取代的杂芳基。当该Ar 2选自取代或未取代的芳基时，碳原子数可以为7、8、9、10、11、12、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、21、22、23、24、25、26、27、28、29或30；当该Ar 2选自取代或未取代的杂芳基时，碳原子数可以为3、4、5、6、7、8、9、10、11、12、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、21、22、23、24、25、26、27、28、29或30。
本申请中，可选地，R 1、R 2彼此相同或不同，且各自独立地选自：氘、氟、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基、碳原子数为5-10的环烷基、基团B、碳原子数为3-18的杂芳基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基或碳原子数为3-7的三烷基硅基。其中，基团B选自总碳原子数为6-15的取代或未取代的芳基，芳基中的取代基各自独立地选自氘、氟、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氟代烷基或碳原子数为3-7的三烷基硅基。例如，R 1、R 2各自独立地选自：氘、氟、氰基、甲基、叔丁基、三氟甲基、三甲基硅基、环戊基、环已基、金刚烷基、苯基、萘基、联苯基，被三氟甲基、甲基、叔丁基、氰基、氟或氘取代的苯基等。
任选地，任意相邻的两个R 1可稠合成环，例如为苯环。任选地，任意相邻的两个R 2可稠合成环，例如为苯环。
本申请中，可选地，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-25的取代或未取代的芳基、总碳原子数为5-25的取代或未取代的杂芳基。
可选地，Ar 1、Ar 2、Ar 3中的取代基各自独立地选自：氘、氟、氰基、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的烷基、碳原子数为1-4的卤代烷基、碳原子数为5-10的环烷基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基或碳原子数为3-7的三烷基硅基。任选地，任意相邻的两个取代基形成5～13元的饱和或不饱和环。
可选地，Ar 1、Ar 2、Ar 3中的取代基各自独立地选自：氘、氟、氰基、苯基、萘基、联苯基、菲基、蒽基、二甲基芴基、吡啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、咔唑基、甲基、乙基、异丙基、叔丁基、三氟甲基、环戊基、环己基、金刚烷基、三甲基硅基、甲硫基、甲硫基。任选地，任意相邻的两个取代基形成芴环、环戊烷或环己烷。
还可选地，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自成环碳原子为6-25的取代或未取代的芳基、成环碳原子为5-25的取代或未取代的杂芳基。其中，取代或未取代的芳基的成环碳原子数例如为6、10、12、13、18、21、25等，取代或未取代的杂芳基的成环碳原子数例如为5、6、7、8、9、10、12、18、20、24、25等。
在一些实施方式中，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自式i-1至式i-15所示基团所组成的组：
Figure PCTCN2021105331-appb-000027
其中，M 1选自单键或者
Figure PCTCN2021105331-appb-000028
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；
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的烷氧基或碳原子数为1～10的烷硫基；
H 2～H 9、H 22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的烷硫基或碳原子数为3～18的杂芳基；
H 10～H 21、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6～18的芳基或碳原子数为3～18的杂芳基；
h 1～h 22以h k表示，H 1～H 22以H k表示，k为变量，表示1～22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、21或者22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H k相同或者不相同；
K 1选自O、S、Se、N(H 23)、C(H 24H 25)、Si(H 24H 25)；其中，H 23、H 24、H 25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、碳原子数为3～10的环烷基，或者上述H 24和H 25相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
K 2选自单键、O、S、Se、N(H 26)、C(H 27H 28)、Si(H 27H 28)；其中，H 26、H 27、H 28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、碳原子数为3～10的环烷基，或者上述H 27和H 28相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
K 3表示O或S。
本申请中，式i-10和i-11中，当K 2表示单键时，式i-10和i-11具体的结构分别如下所示：
Figure PCTCN2021105331-appb-000029
本申请中，上述H 24与H 25、上述H 27与H 28两组中，每组中的两个基团相互连接所形成的环可以是5-13元的饱和或不饱和环。可选地，上述H 24与H 25、上述H 27与H 28两组中，每组中的两个基团相互连接所形成的环可以为5～13元的饱和脂肪族环或芳香环。按照一种实施方式，上述H 24与H 25、上述H 27与H 28两组可以分别形成5～8元的饱和脂肪族单环或者形成10～13元芳香环。举例来讲，式i-10中，当K 2和M 1均为单键，h 19＝7，H 19为氢，K 1为C(H 24H 25)，H 24与H 25相互连接以与它们共同连接的原子一起形成5元的饱和脂肪族单环时，式i-10即为
Figure PCTCN2021105331-appb-000030
同样地，式i-10也可以为
Figure PCTCN2021105331-appb-000031
即H 24与H 25相互连接以与它们共同连接的原子一起形成13元芳香环。
式i-13至式i-15中，F 2至F 4可以以F j表示，其中的j为变量，表示2、3或4。举例来讲，当j为2时，J j是指J 2。应当理解地是，当不定位连接键连接到C(F j)上时，C(F j)中的F j不存在。例如， 在式i-13中，当
Figure PCTCN2021105331-appb-000032
连接到G 12时，G 12只能表示C原子，即式i-13的结构具体为：
Figure PCTCN2021105331-appb-000033
同理，下文中涉及到L 1至L 3的式j-4中，当
Figure PCTCN2021105331-appb-000034
连接到各个含C基团(C(F 4))的Q(例如Q 1)上时，Q表示C原子。
可选地，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自取代或未取代的基团Z，其中，未取代的基团Z选自如下基团所组成的组：
Figure PCTCN2021105331-appb-000035
取代的基团Z中具有一个或者两个以上取代基，且取代基分别独立地选自氘、氰基、氟、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1-4的卤代烷基、碳原子数为3-7的三烷基硅基；取代基个数大于1时，各取代基相同或不同。
可选地，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自如下基团所组成的组：
Figure PCTCN2021105331-appb-000036
Figure PCTCN2021105331-appb-000037
进一步可选地，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自如下基团所组成的组：
Figure PCTCN2021105331-appb-000038
本申请中，可选地，L 1和L 3彼此相同或不同，且各自独立地选自总碳原子数为6-12的取代或未取代的亚芳基、总碳原子数为5-12的取代或未取代的亚杂芳基。
还可选地，L 1和L 3彼此相同或不同，且各自独立地选自成环碳原子数为6-12的取代或未取代的芳基、成环碳原子数为5-12的取代或未取代的杂芳基。其中，取代或未取代的芳基的成环碳原子数例如为6、10、12等，取代或未取代的杂芳基的成环碳原子数例如为5、6、7、8、9、10、12。
可选地，L 2选自单键、总碳原子数为6-12的取代或未取代的亚芳基、总碳原子数为5-12的取代或未取代的亚杂芳基。
还可选地，L 2选自单键、成环碳原子数为6-12的取代或未取代的亚芳基、成环碳原子数为5-12的取代或未取代的亚杂芳基。其中，取代或未取代的亚芳基的成环碳原子数例如为6、10、12等，取代或未取代的亚杂芳基的成环碳原子数例如为5、6、7、8、9、10、12等。
可选地，L 1、L 2、L 3中的取代基相同或不同，且各自独立的选自：氘、氟、氰基、苯基、吡啶基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基或碳原子数为3-7的三烷基硅基。
进一步可选地，L 1、L 2、L 3中的取代基各自独立的选自：氘、氟、氰基、苯基、吡啶基、甲基、乙基、异丙基、叔丁基、三氟甲基或三甲基硅基。
在一些实施方式中，L 1、L 2和L 3彼此相同或不同，且各自独立地选自如下式j-1至式j-4所示基团所组成的组：
Figure PCTCN2021105331-appb-000039
其中，M 2选自单键或者
Figure PCTCN2021105331-appb-000040
Q 1～Q 5各自独立地选自N或者C(F 4)，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(F 4)时，任意两个F 4相同或者不相同；
E 1～E 5、F 4各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～10的杂芳基、碳原子数为6～12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3～10的环烷基、碳原子数为1～10的烷氧基或碳原子数为1～10的烷硫基；
E 1～E 5以E r表示，e 1～e 5以e r表示，其中的r表示变量并选自1～5的任意整数；当r选自1、2、3或5时，e r选自1、2、3或者4；当r为4时，e r选自1、2、3、4、5或者6；且当e r大于1时，任意两个E r相同或者不相同。
可选地，L 1、L 2和L 3彼此相同或不同，且各自独立地选自取代或未取代的基团V，其中，未取代的基团V选自如下基团所组成的组：
Figure PCTCN2021105331-appb-000041
取代的基团V中具有一个或者两个以上取代基，且取代基分别独立地选自氘、氰基、氟、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1-4的卤代烷基、碳原子数为3-7的三烷基硅基，取代基个数大于1时，各取代基相同或不同。
可选地，L 1、L 2和L 3彼此相同或不同，且各自独立地选自取代或未取代的亚苯基、取代或未取代的亚联苯基、取代或未取代的亚吡啶基、取代或未取代的亚萘基，取代基为苯基。
按照一种示例性的实施方式，L 1、L 2和L 3彼此相同或不同，且各自独立地选自以下基团所组成的组：
Figure PCTCN2021105331-appb-000042
在一种实施方式中，所述含氮化合物的结构如式A或式D所示。该实施方式中，所述含氮化合物可以作为电子元件的空穴传输层材料，如作为有机电致发光器件的第一空穴传输层材料和/或第二空穴传输层(也称电子阻挡层)材料。
优选地，Ar 1、Ar 2、Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-25的取代或未取代的芳基、总碳原子数为5-20的取代或未取代的杂芳基。
优选地，L 1选自总碳原子数为6-12的取代或未取代的亚芳基；L 2选自单键、总碳原子数为6-12取代或未取代的亚芳基。
在另一种实施方式中，所述含氮化合物的结构如式B、式C或式E所示。该实施方式中，所述含氮化合物可以作为电子元件的发光层材料，如有机电致发光器件的发光层主体材料。
优选地，Ar 3选自总碳原子数为6-20的取代或未取代的芳基、总碳原子数为5-20的取代或未取代的杂芳基。
优选地，L 2选自单键、总碳原子数为6-12的取代或未取代的亚芳基。
优选地，L 3选自总碳原子数为6-12的取代或未取代的亚芳基。
在一种实施方式中，所述含氮化合物的结构如式A所示。优选地，Ar 1选自成环碳原子数为6-20的取代或未取代的芳基，Ar 2选自成环碳原子数为10-25的取代或未取代的芳基、成环碳原子数为7-20的取代或未取代的杂芳基。这种情况下，所述含氮化合物可进一步提高器件的综合性能，尤其是器件的寿命。
在另一种具体的实施方式中，所述含氮化合物的结构如式C所示。优选地，两个L 3中，至少有一个L 3选自取代或未取代的成环碳原子数为10-20的亚芳基。这种情况下，所述含氮化合物可进一步提高器件的综合性能，尤其是器件的寿命。
可选地，所述含氮化合物选自如下化合物所组成的组：
Figure PCTCN2021105331-appb-000043
Figure PCTCN2021105331-appb-000044
Figure PCTCN2021105331-appb-000045
Figure PCTCN2021105331-appb-000046
Figure PCTCN2021105331-appb-000047
Figure PCTCN2021105331-appb-000048
Figure PCTCN2021105331-appb-000049
本申请对提供的含氮化合物的合成方法没有特别限定，本领域技术人员可以根据本申请的含氮化合物结合合成例部分提供的制备方法确定合适的合成方法。换言之，本发明的合成例部分示例性地提供了含氮化合物的制备方法，所采用的原料可通过商购获得或本领域熟知的方法获得。本领域技术人员可以根据这些示例性的制备方法得到本申请提供的所有含氮化合物，在此不再详述制备该含氮化合物的所有具体制备方法，本领域技术人员不应理解为对本申请的限制。
本申请还提供一种电子元件，所述电子元件包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请的含氮化合物。通常地，所述电子元件可以为有机电致发光器件或光电转化器件。
可选地，所述功能层包括空穴传输层，所述空穴传输层可以为一层或两层以上。
可选地，所述功能层包括发光层，所述发光层包括主体材料和客体材料。
在一种实施方式中，所述空穴传输层可以包括所述含氮化合物。在另一种实施方式中，所述发光层的主体材料包括所述含氮化合物。本申请提供的含氮化合物可应用于有机电致发光器件的空穴传输层或作为发光层的主体材料，在保证较低驱动电压的情况下，可提高有机电致发光器件的发光效率和寿命。
本申请中，所述有机电致发光器件可以为红光器件、蓝光器件或绿光器件。
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。如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层320、作为能量转化层的发光层330、电子传输层340和阴极200，其中，空穴传输层320包括第一空穴传输层321和第二空穴传输层322。如图所示，所述第一空穴传输层321较第二空穴传输层322更靠近阳极100。
本申请中，阳极100包括阳极材料，其优选是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料的具体实例包括但不限于：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
本申请中，空穴传输层320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。在本申请的一种实施方式中，本申请提供的含氮化合物可应用于有机电致发光器件的第一空穴传输层321和/或第二空穴传输层322。例如，所述第一空穴传输层321和第二空穴传输层322中的一者包含本申请的化合物，另一者可以由化合物HT-02或HT-01组成。
本申请中，发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。一种具体的实施方式中，发光层330由主体材料和客体材料组成，注入发光层330的空穴和注入发光层330的电子可以在发光层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。
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。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。在本申请的一种实施方式中，发光层330的主体材料包含BH-01，客体材料包含BD-01。在本申请的另一种实施方式中，发光层330的主体材料包含本申请的化合物。例如，发光层330的主体材料包含本申请的含氮化合物和GH-n1，客体材料包含Ir(ppy) 3。
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，苯并咪唑衍生物、恶二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种实施方式中，电子传输层340可以由ET-01和LiQ组成。
本申请中，HT-02、HT-01、BH-01、BD-01、ET-01、GH-n1等的具体结构如下文的实施例所述，在此不再赘述。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向空穴传输层注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。例如，空穴注入层310可以由F4-TCNQ组成。
可选地，如图1所示，在阴极200和电子传输层340之间还可以设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物、Yb等无机材料，或者可以包括碱金属与有机物的络合物。例如，电子注入层350可以包括LiQ。
可选地，如图1所示，空穴注入层310、第一空穴传输层321、第二空穴传输层322、发光层330、电子传输层340和电子注入层350组成功能层300。
按照另一种实施方式，电子元件可以为光电转化器件。如图2所示，该光电转化器件可以包括相对设置的阳极100和阴极200，以及设于阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的含氮化合物。
可选地，所述功能层300包括空穴传输层320，所述空穴传输层320包含本申请的含氮化合物。其中，空穴传输层320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，空穴传输层320还可以包括无机掺杂材料，以提高空穴传输层320的空穴传输性能。
按照一种示例性的实施方式，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320、光电转化层360、电子传输层340和阴极200。
可选地，光电转化器件可以为太阳能电池，尤其是可以为有机薄膜太阳能电池。举例而言，在本申请的一种实施方式中，太阳能电池可以包括依次层叠设置的阳极、空穴传输层、光电转化层、电子传输层和阴极，其中，空穴传输层包含有本申请的含氮化合物。
本申请还提供一种电子装置，该电子装置包括上述电子元件。
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，第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式，如图4所示，所述电子装置为第二电子装置500，第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
以下，通过合成例和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。
合成例用于说明化合物的合成。
用于合成本申请化合物的反应物可以包括结构如下所示的中间体IM 1-I、IM 2-I和IM 3-I；
Figure PCTCN2021105331-appb-000050
其中，上述反应物可通过商购获得；也可以通过本领域熟知的方法获得，例如可参照文献KR1020140082486A、WO2014081206A1、WO2012015274A2合成，合成上述反应物的具体方法为本领域所熟知，在此不再赘述。
合成例中，所采用的IM 1-I包括以下中间体IM 1-1至IM 1-9：
Figure PCTCN2021105331-appb-000051
中间体IM 2-I包括以下IM 2-1至IM 2-11：
Figure PCTCN2021105331-appb-000052
Figure PCTCN2021105331-appb-000053
中间体IM 3-I包括IM 3-1至IM 3-4：
Figure PCTCN2021105331-appb-000054
合成例1
使用以下方法进行化合物A1的合成：
Figure PCTCN2021105331-appb-000055
向干燥并经过氮气置换的100mL圆底烧瓶中，加入1,8-二溴萘(2.0g；7.0mmol)，IM 1-1(7.1g；21.0mmol)，醋酸钯(0.3g；1.4mmol)，2-二环己基磷-2,4,6-三异丙基联苯(0.7g；1.4mmol)，碳酸铯(6.8g；21.0mmol)，甲苯(30mL)，搅拌条件下升温至105-110℃，保持18h；而后将反应混合物降至室温，加入去离子水(90mL)，搅拌30min，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用体积比为1∶3二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色固体化合物A1(1.9g；收率38％)。
合成例2至9
参照合成化合物A1的方法合成表1中化合物，不同的是，使用下表中反应物A替代IM 1-1：
表1
Figure PCTCN2021105331-appb-000056
Figure PCTCN2021105331-appb-000057
Figure PCTCN2021105331-appb-000058
合成例10至20
1、中间体IM a至IM k的合成
1)使用以下方法进行IM a的合成：
Figure PCTCN2021105331-appb-000059
向干燥并经过氮气置换的250mL圆底烧瓶中，加入中间体IM 1-4(10.0g；34.6mmol)，1,8-二溴萘(10.9g；38.0mmol)，四(三苯基膦)钯(0.8g；0.7mmol)，四丁基溴化铵(2.2g；6.9mmol)，碳酸钾(7.2g；51.9mmol)，甲苯(100mL)，乙醇(20mL)，去离子水(20mL)，搅拌条件下升温至75-80℃，保持12h；而后将反应混合物降至室温，加入去离子水(200mL)，搅拌10min，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用体积比1∶5二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色固体中间体IM a(11.7g；收率75％)
2)参照中间体IM a相同的方法合成表2中的中间体，不同的是，以表2的反应物B替代中间体1-4：
表2
Figure PCTCN2021105331-appb-000060
Figure PCTCN2021105331-appb-000061
合成例10
使用以下方法进行化合物A30的合成：
Figure PCTCN2021105331-appb-000062
向干燥并经过氮气置换的100mL圆底烧瓶中，加入中间体IM a(3.0g；6.7mmol)，IM 1-5(4.0g；10.0mmol)，醋酸钯(0.3g；1.3mmol),2-二环己基磷-2,4,6-三异丙基联苯(0.6g；1.3mmol),碳酸铯(3.3g；10.0mmol)，甲苯(40mL)，搅拌条件下升温至105-110℃，保持16h；而后将反应混合物降至室温，加入去离子水(100mL)，搅拌30分钟，分离有机相，加入无水硫酸镁干燥后，减压除去溶剂；将所得粗产品使用体积比1∶2二氯甲烷/正庚烷作为流动相进行硅胶柱色谱提纯，得到白色固体化合物A30(2.0g；收率41％)。
合成例11-20
参照化合物A30的方法合成表3所示的化合物，不同的是，以下表中反应物C替代中间体IM a，以反应物D替代IM 1-5，合成表3中化合物：
表3
Figure PCTCN2021105331-appb-000063
Figure PCTCN2021105331-appb-000064
对以上合成化合物进行质谱分析，得到数据如下所示：
化合物A1：m/z＝715.3(M+H) + 化合物B16：m/z＝763.3(M+H) +
化合物A3：m/z＝643.3(M+H) + 化合物B18：m/z＝611.2(M+H) +
化合物A21：m/z＝919.4(M+H) + 化合物B28：m/z＝737.3(M+H) +
化合物A30：m/z＝731.3(M+H) + 化合物B41：m/z＝687.3(M+H) +
化合物A36：m/z＝807.4(M+H) + 化合物C3：m/z＝841.4(M+H) +
化合物A39：m/z＝817.4(M+H) + 化合物C5：m/z＝789.3(M+H) +
化合物B1：m/z＝611.2(M+H) + 化合物C10：m/z＝855.3(M+H) +
化合物B5：m/z＝763.3(M+H) + 化合物C12：m/z＝915.4(M+H) +
化合物B10：m/z＝763.3(M+H) + 化合物C13：m/z＝779.3(M+H) +
化合物B23：m/z＝763.3(M+H) + 化合物B46：m/z＝687.3(M+H)
化合物A1的核磁数据：
1H NMR(CD 2Cl 2,400MHz):7.82(d,2H),7.77(d,2H),7.71(d,2H),7.54(d,2H),7.48(t,2H),7.38(t,2H),7.34-7.29(m,4H),7.25(t,2H),7.15(d,2H),7.05(t,4H),7.01(t,4H),6.95(d,4H),6.81-6.77(m,6H).
化合物B28的核磁数据：
1H NMR(CD 2Cl 2,400MHz):8.03-7.99(m,2H),7.95(d,1H)，7.91-7.88(m,3H),7.79(d,2H),7.69-7.66(m,2H),7.64-7.58(m,4H),7.57-7.53(m,5H),7.51-7.46(m,5H),7.43(t,1H),7.38-7.32(m,3H),7.24-7.18(m,6H),7.05-7.01(m,2H).
有机电致发光器件制备及评估
实施例1至11：蓝色有机发光电致器件制备及评估
实施例1
通过以下过程制备阳极：将厚度为
Figure PCTCN2021105331-appb-000065
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 PCTCN2021105331-appb-000066
的空穴注入层(HIL)，并且在空穴注入层蒸镀化合物A1，形成厚度为
Figure PCTCN2021105331-appb-000067
的第一空穴传输层(HTL1)。
在第一空穴传输层上真空蒸镀化合物HT-02，形成厚度为
Figure PCTCN2021105331-appb-000068
的第二空穴传输层(HTL2)。
在第二空穴传输层上，将BH-01∶BD-01以98％∶2％的蒸镀速率比进行共同蒸镀，形成厚度为
Figure PCTCN2021105331-appb-000069
的蓝色发光层(EML)。
将ET-01和LiQ以1∶1的重量比进行混合并蒸镀形成
Figure PCTCN2021105331-appb-000070
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 PCTCN2021105331-appb-000071
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 PCTCN2021105331-appb-000072
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021105331-appb-000073
的CP-01，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例2-实施例6
除了在形成第一空穴传输层时，以下表4中所示的化合物替代化合物A1以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1-比较例2
除了在形成第一空穴传输层时，比较例1、比较例2分别以HT-01、化合物a替代化合物A1以外，利用与实施例1相同的方法制作有机电致发光器件。
实施例7-实施例11
除了在形成第一空穴传输层时，以化合物HT-01替代化合物A1，并在形成第二空穴传输层时， 以表4中的化合物替代HT-02以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例3
除了在形成第一空穴传输层时，以化合物HT-01替代化合物A1，并在形成第二空穴传输层时，以化合物b替代HT-02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主要材料结构如下所示：
Figure PCTCN2021105331-appb-000074
对如上制得的有机电致发光器件，在10mA/cm 2的条件下分析了器件光电性能，在20mA/cm 2的条件下分析了器件寿命性能，其结果示于表4。
表4
Figure PCTCN2021105331-appb-000075
Figure PCTCN2021105331-appb-000076
结合上表所知，在器件其他层相同的情况下，将实施例1至6与比较例1-2相比可知，本申请的化合物作为第一空穴传输层材料时，能降低驱动电压，并提高器件寿命；将实施例7至11与比较例1和3相比可知，本申请的化合物作为第二空穴传输层材料时，能同时提高器件发光效率和器件寿命。因此，本申请的化合物用于制备蓝色有机电致发光器件时，可以有效地延长有机电致发光器件的寿命，并一定程度上改善发光效率或驱动电压。
实施例12至20：绿色有机发光电致器件制备及评估
实施例12
通过以下过程制备阳极：将厚度为
Figure PCTCN2021105331-appb-000077
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 PCTCN2021105331-appb-000078
的空穴注入层(HIL)，并且在空穴注入层蒸镀HT-01，形成厚度为
Figure PCTCN2021105331-appb-000079
的第一空穴传输层。
在第一空穴传输层上真空蒸镀HT-02，形成厚度为
Figure PCTCN2021105331-appb-000080
的第二空穴传输层。
在第二空穴传输层上，将化合物B1∶GH-n1∶Ir(ppy) 3以50％∶45％∶5％的蒸镀速率比例进行共同蒸镀，形成厚度为
Figure PCTCN2021105331-appb-000081
的绿色发光层(EML)。
将ET-01和LiQ以1∶1的重量比进行混合并蒸镀形成
Figure PCTCN2021105331-appb-000082
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 PCTCN2021105331-appb-000083
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 PCTCN2021105331-appb-000084
的阴极。
此外，在上述阴极上蒸镀厚度为
Figure PCTCN2021105331-appb-000085
的CP-01，形成有机覆盖层(CPL)，从而完成有机发光器件的制造。
实施例13-实施例20
除了在形成发光层时，以下表5中所示的化合物替代化合物B1(化合物B1与代替B1的化合物在表5中统称为EM1化合物)以外，利用与实施例12相同的方法制作有机电致发光器件。
比较例4-5
除了在形成发光层时，比较例4和5分别以化合物c、化合物d替代化合物B1以外，利用与实施例12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所示：
Figure PCTCN2021105331-appb-000086
对如上制得的有机电致发光器件，在10mA/cm 2的条件下分析了器件光电性能，在20mA/cm 2的条件下分析了器件寿命性能，其结果示于下表：
表5
Figure PCTCN2021105331-appb-000087
结合表5的数据可知，实施例12-20将本发明化合物用作绿色发光层的混合主体材料，与比较例4相比，在驱动电压和电流效率水平相当的情况下，器件寿命得到了较大幅度的增强；与比较例5相比，电流效率和寿命亦具有一定幅度的提高。
综上，本申请的含氮化合物用于制备绿色有机电致发光器件时，可以有效地延长有机电致发光器件的寿命，并且兼具较高的发光效率和和较低的驱动电压。

Claims (16)

  1. 一种含氮化合物，其特征在于，所述含氮化合物的结构如式1所示：
    Figure PCTCN2021105331-appb-100001
    B 1、B 2彼此相同或不同，且各自独立地选自式1-1、式1-2或式1-3所示的基团，且B 1、B 2不为式1-1和式1-3的组合：
    Figure PCTCN2021105331-appb-100002
    其中，
    Figure PCTCN2021105331-appb-100003
    表示化学键；
    Ar 1、Ar 2、Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-30的取代或未取代的芳基、总碳原子数为3-30的取代或未取代的杂芳基；
    L 1选自总碳原子数为6-20的取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
    L 2、L 3彼此相同或不同，且各自独立地选自单键、总碳原子数为6-20的取代或未取代的亚芳基、总碳原子数为4-15的取代或未取代的亚杂芳基；
    R 1、R 2彼此相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为1-10的烷基、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3-10的环烷基、基团A、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的烷硫基或碳原子数为3-12的三烷基硅基；基团A选自总碳原子数为6-20的取代或未取代的芳基，芳基中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基、碳原子数为3-10的环烷基或碳原子数为3-7的三烷基硅基；
    n 1为取代基R 1的数量，n 1选自0、1、2、3、4、5、6或7，当n 1大于1时，任意两个R 1相同或不同，任选地，任意两个相邻的R 1形成环；n 2为取代基R 2的数，n 2选自0、1、2、3、4、5、6、7或8，当n 2大于1时，任意两个R 2相同或不同，任选地，任意两个相邻的R 2形成环；
    Ar 1、Ar 2、Ar 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-20的芳基、碳原子数为3-18的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
    L 1、L 2、L 3中的各取代基相同或不同，且各自独立地选自：氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为3-12的杂芳基、碳原子数为1-10的烷基、碳原子数为1-10的卤代烷基、碳原子数为3-10的环烷基、碳原子数为1-10的烷氧基、碳原子数为1-10的烷硫基或碳原子数为3-12的三烷基硅基；
    任选地，Ar 1、Ar 2、Ar 3、L 1、L 2和L 3的取代基中，任意两个相邻的取代基形成环；
    并且，
    B 1、B 2不同时为
    Figure PCTCN2021105331-appb-100004
    当B 1选自式1-3结构，且L 3为取代或未取代的1,4-亚苯基时，B 2的结构与B 1不同。
  2. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下式A至式E所组成的组：
    Figure PCTCN2021105331-appb-100005
    优选地，R 1、R 2彼此相同或不同，且各自独立地选自：氘、氟、氰基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基、碳原子数为5-10的环烷基、基团B、碳原子数为3-18的杂芳基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基或碳原子数为3-7的三烷基硅基；基团B选自总碳原子数为6-15的取代或未取代的芳基，芳基中的取代基各自独立地选自氘、氟、氰基、碳原子数为1-4的烷基、碳原子数为1-4的氟代烷基或碳原子数为3-7的三烷基硅基。
  3. 根据权利要求1或2所述的含氮化合物，其特征在于，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-25的取代或未取代的芳基、总碳原子数为5-25的取代或未取代的杂芳基；
    优选地，Ar 1、Ar 2、Ar 3中的取代基各自独立地选自：氘、氟、氰基、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的烷基、碳原子数为1-4的卤代烷基、碳原子数为5-10的环烷基、碳原子数为1-4的烷氧基、碳原子数为1-4的烷硫基或碳原子数为3-7的三烷基硅基。
  4. 根据权利要求1或2所述的含氮化合物，其特征在于，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自式i-1至式i-15所示基团所组成的组：
    Figure PCTCN2021105331-appb-100006
    Figure PCTCN2021105331-appb-100007
    其中，M 1选自单键或者
    Figure PCTCN2021105331-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；
    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的烷氧基或碳原子数为1～10的烷硫基；
    H 2～H 9、H 22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的烷硫基或碳原子数为3～18的杂芳基；
    H 10～H 21、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6～18的芳基或碳原子数为3～18的杂芳基；
    h 1～h 22以h k表示，H 1～H 22以H k表示，k为变量，表示1～22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、21或者22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H k相同或者不相同；
    K 1选自O、S、Se、N(H 23)、C(H 24H 25)、Si(H 24H 25)；其中，H 23、H 24、H 25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H 24和H 25相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
    K 2选自单键、O、S、Se、N(H 26)、C(H 27H 28)、Si(H 27H 28)；其中，H 26、H 27、H 28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H 27和H 28相互连接以与它们共同连接的原子一起形成5～13元的饱和或不饱和环；
    K 3选自O或S。
  5. 根据权利要求1或2所述的含氮化合物，其特征在于，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自取代或未取代的基团Z，其中，未取代的基团Z选自如下基团所组成的组：
    Figure PCTCN2021105331-appb-100009
    取代的基团Z中具有一个或者两个以上取代基，且各取代基分别独立地选自氘、氰基、氟、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1-4的卤代烷基、碳原子数为3-7的三烷基硅基；取代基个数大于1时，各取代基相同或不同。
  6. 根据权利要求1或2所述的含氮化合物，其特征在于，Ar 1、Ar 2和Ar 3彼此相同或不同，且各自独立地选自如下基团所组成的组：
    Figure PCTCN2021105331-appb-100010
    Figure PCTCN2021105331-appb-100011
  7. 根据权利要求1或2所述的含氮化合物，其特征在于，L 1和L 3彼此相同或不同，且各自独立地选自总碳原子数为6-12的取代或未取代的亚芳基、总碳原子数为5-12的取代或未取代的亚杂芳基；L 2选自单键、总碳原子数为6-12的取代或未取代的亚芳基、总碳原子数为5-12的取代或未取代的亚杂芳基；
    优选地，L 1、L 2、L 3中的取代基相同或不同，且各自独立的选自：氘、氟、氰基、苯基、吡啶基、碳原子数为1-4的烷基、碳原子数为1-4的卤代烷基或碳原子数为3-7的三烷基硅基。
  8. 根据权利要求1或2所述的含氮化合物，其特征在于，L 1、L 2和L 3相同或不同，且各自独立地选自如下式j-1至式j-4所示基团所组成的组：
    Figure PCTCN2021105331-appb-100012
    其中，M 2选自单键或者
    Figure PCTCN2021105331-appb-100013
    Q 1～Q 5各自独立地选自N或者C(F 4)，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(F 4)时，任意两个F 4相同或者不相同；
    E 1～E 5、F 4各自独立地选自：氢、氘、氟、氯、溴、氰基、碳原子数为3～10的杂芳基、碳原子数为6～12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3～10的环烷基、碳原子数为1～10的烷氧基或碳原子数为1～10的烷硫基；
    E 1～E 5以E r表示，e 1～e 5以e r表示，其中的r表示变量并选自1～5的任意整数；当r选自1、2、3或5时，e r选自1、2、3或者4；当r为4时，e r选自1、2、3、4、5或者6；且当e r大于1时，任意两个E r相同或者不相同。
  9. 根据权利要求1或2所述的含氮化合物，其特征在于，L 1、L 2和L 3彼此相同或不同，且各 自独立地选自取代或未取代的基团V，其中，未取代的基团V选自如下基团所组成的组：
    Figure PCTCN2021105331-appb-100014
    取代的基团V中具有一个或者两个以上取代基，且取代基分别独立地选自氘、氰基、氟、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1-4的卤代烷基、碳原子数为3-7的三烷基硅基，取代基个数大于1时，各取代基相同或不同。
  10. 根据权利要求2所述的含氮化合物，其特征在于，所述含氮化合物的结构如式A或式D所示；优选地，Ar 1、Ar 2、Ar 3彼此相同或不同，且各自独立地选自总碳原子数为6-25的取代或未取代的芳基、总碳原子数为5-20的取代或未取代的杂芳基；或者
    所述含氮化合物的结构如式B、式C或式E所示；优选地，Ar 3选自总碳原子数为6-20的取代或未取代的芳基、总碳原子数为5-20的取代或未取代的杂芳基。
  11. 根据权利要求2或10所述的含氮化合物，其特征在于，所述含氮化合物的结构如式A所示，其中，Ar 1选自成环碳原子数为6-20的取代或未取代的芳基，Ar 2选自成环碳原子数为10-25的取代或未取代的芳基、成环碳原子数为7-20的取代或未取代的杂芳基；或者
    所述含氮化合物的结构如式C所示，其中，两个L 3中，至少有一个L 3选自成环碳原子数为10-20的取代或未取代亚芳基。
  12. 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 PCTCN2021105331-appb-100015
    Figure PCTCN2021105331-appb-100016
    Figure PCTCN2021105331-appb-100017
    Figure PCTCN2021105331-appb-100018
    Figure PCTCN2021105331-appb-100019
    Figure PCTCN2021105331-appb-100020
    Figure PCTCN2021105331-appb-100021
  13. 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1-12中任一项所述的含氮化合物。
  14. 根据权利要求13所述的电子元件，其特征在于，所述电子元件为有机电致发光器件或光电转化器件。
  15. 根据权利要求13或14所述的电子元件，其特征在于，所述功能层包括空穴传输层，所述空穴传输层包括所述含氮化合物；和/或
    所述功能层包括发光层，所述发光层包括主体材料和客体材料，其中，所述主体材料包括所述的含氮化合物。
  16. 一种电子装置，其特征在于，包括权利要求13-15任一项所述的电子元件。
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CN115466184A (zh) * 2022-09-20 2022-12-13 北京八亿时空液晶科技股份有限公司 一种有机化合物及其应用

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