WO2022121618A1 - 一种含氮化合物以及使用其的电子元件和电子装置 - Google Patents

一种含氮化合物以及使用其的电子元件和电子装置 Download PDF

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WO2022121618A1
WO2022121618A1 PCT/CN2021/130172 CN2021130172W WO2022121618A1 WO 2022121618 A1 WO2022121618 A1 WO 2022121618A1 CN 2021130172 W CN2021130172 W CN 2021130172W WO 2022121618 A1 WO2022121618 A1 WO 2022121618A1
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substituted
carbon atoms
unsubstituted
nitrogen
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French (fr)
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马天天
杨敏
南朋
郑奕奕
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陕西莱特光电材料股份有限公司
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Definitions

  • the present application relates to the technical field of organic materials, in particular, to a nitrogen-containing compound and electronic components and electronic devices using the same.
  • 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.
  • the purpose of the present application is to provide a nitrogen-containing compound and electronic components and electronic devices using the same.
  • the nitrogen-containing compound can be used in organic electroluminescent devices to improve the performance of organic electroluminescent devices performance.
  • a first aspect of the present application provides a nitrogen-containing compound, and the organic compound has the structure shown in the following formula I:
  • T 1 is selected from O or S;
  • L and L 1 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms base;
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms;
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 2-30 carbon atoms;
  • Ar 2 is selected from the structure represented by formula II or formula III;
  • X and Y are independently selected from single bond, O, S, C(R 5 R 6 ) or N(R 7 ), and X and Y are not single bonds at the same time;
  • R 5 , R 6 and R 7 are the same or different, and are each independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a 3-30 substituted or unsubstituted heteroaryl;
  • Z is selected from O, S, C(R 8 R 9 ) or N(R 10 );
  • R 8 , R 9 and R 10 are the same or different, and are each independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a 3-30 substituted or unsubstituted heteroaryl;
  • any of R 5 and R 6 , R 8 and R 9 and the atoms to which they are commonly attached form a saturated or unsaturated ring having 3-14 carbon atoms;
  • R 1 , R 2 , R 3 and R 4 are the same or different, and are each independently selected from deuterium, a halogen group, an alkyl group having 1-10 carbon atoms, a cycloalkyl group having 3-10 carbon atoms, An aryl group with a carbon number of 6-20, a heteroaryl group with a carbon number of 3-24;
  • R 1 -R 4 are represented by R i
  • n 1 -n 4 are represented by n i
  • i is a variable, representing 1, 2, 3 or 4
  • n 1 , n 2 , n 3 and n 4 represent R 1 , R respectively 2 , the number of R 3 and R 4 ;
  • n i is selected from 0, 1, 2 or 3; when i is 2, 3 or 4, n i is selected from 0, 1, 2, 3 or 4;
  • n i is greater than 1, any two n i are the same or different;
  • any two adjacent R i are connected to the benzene ring to form a naphthalene ring or a phenanthrene ring;
  • the substituent in L 2 is selected from deuterium, halogen group, cyano group, phenyl group;
  • the substituents in L, L 1 , Ar 1 and R 5 -R 10 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optional Aryl having 6-20 carbon atoms, substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl It is a trialkylsilyl group of 3-12, a triarylsilyl group with a carbon number of 18-24, an alkyl group with a carbon number of 1-10, a halogenated alkyl group with a carbon number of 1-10, and a carbon number of 1-10.
  • Cycloalkyl with 3-10 heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, 6 carbon atoms -18 aryloxy group, arylthio group having 6-18 carbon atoms, phosphineoxy group having 6-18 carbon atoms.
  • a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the nitrogen-containing element described in the first aspect of the present application compound;
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound;
  • the organic light-emitting layer includes a host material and a guest material, and the host material includes the nitrogen-containing compound.
  • a third aspect of the present application provides an electronic device, and the electronic device includes the electronic element described in the second aspect of the present application.
  • the nitrogen-containing compound of the present application can significantly reduce the driving voltage of the device and improve the service life of the device; in addition, the nitrogen-containing compound of the present application can also improve the luminous efficiency of the device.
  • the nitrogen-containing compound provided by the present application uses azadibenzofuran/dibenzothiophene and triazine as core groups, and uses electron-rich condensed heteroaryl groups as fixed substituent groups on triazine.
  • monoazadibenzofuran/dibenzothiophene has high electron mobility, and combined with the electron-deficient triazine group, can effectively improve the electron injection and transport ability of the material;
  • the electron-fused heteroaryl group is attached to the triazine, which can effectively improve the molecular polarity, thereby further improving the electron transport ability of the material.
  • the compound of the present application has a relatively high T1 value, and is especially suitable for the host material of organic electroluminescence devices, especially the green light host material.
  • the electron transport performance of the device will be effectively improved, thereby enhancing the balance of hole and electron injection, and improving the luminous efficiency and service life of the device.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
  • FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
  • the present application provides a nitrogen-containing compound, and the nitrogen-containing compound has the structure shown in the following formula I:
  • T 1 is selected from O or S;
  • L and L 1 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3-30 carbon atoms base;
  • L 2 is selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms;
  • Ar 1 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 2-30 carbon atoms;
  • Ar 2 is selected from the structure represented by formula II or formula III;
  • X and Y are independently selected from single bond, O, S, C(R 5 R 6 ) or N(R 7 ), and X and Y are not single bonds at the same time;
  • R 5 , R 6 and R 7 are the same or different, and are each independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a 3-30 substituted or unsubstituted heteroaryl;
  • Z is selected from O, S, C(R 8 R 9 ) or N(R 10 );
  • R 8 , R 9 and R 10 are the same or different, and are each independently selected from an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a 3-30 substituted or unsubstituted heteroaryl;
  • any of R 5 and R 6 , R 8 and R 9 and the atoms to which they are commonly attached form a saturated or unsaturated ring having 3-14 carbon atoms;
  • R 1 , R 2 , R 3 and R 4 are the same or different, and are each independently selected from deuterium, a halogen group, an alkyl group having 1-10 carbon atoms, a cycloalkyl group having 3-10 carbon atoms, Unsubstituted aryl groups with 6-20 carbon atoms, unsubstituted heteroaryl groups with 3-24 carbon atoms;
  • R 1 -R 4 are represented by R i
  • n 1 -n 4 are represented by n i
  • i is a variable, representing 1, 2, 3 or 4
  • n 1 , n 2 , n 3 and n 4 represent R 1 , R respectively 2 , the number of R 3 and R 4 ;
  • n i is selected from 0, 1, 2 or 3;
  • n i is selected from 0, 1, 2, 3 or 4;
  • n i is greater than 1, any two n i are the same or different;
  • any two adjacent R i are connected to the benzene ring to form a naphthalene ring or a phenanthrene ring;
  • the substituent in L 2 is selected from deuterium, halogen group, cyano group, phenyl group;
  • the substituents in L, L 1 , Ar 1 and R 5 -R 10 are the same or different, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optional Aryl having 6-20 carbon atoms, substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl and tert-butyl It is a trialkylsilyl group of 3-12, a triarylsilyl group with a carbon number of 18-24, an alkyl group with a carbon number of 1-10, a halogenated alkyl group with a carbon number of 1-10, and a carbon number of 1-10.
  • Cycloalkyl with 3-10 heterocycloalkyl with 2-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, 6 carbon atoms -18 aryloxy group, arylthio group having 6-18 carbon atoms, phosphineoxy group having 6-18 carbon atoms.
  • formula II when formula II is linked to formula I, it refers to the main part of the group of formula II Linked to formula I through a single bond, L 2 in formula I is not linked to R 3 , R 4 , R 5 , R 6 or R 7 as substituents in formula II. It should be clear that when X or Y is selected from N( R7 ) and L2 is attached to N( R7 ) in formula II , R7 is absent. For example, when X is N (R 7 ), Y is O, n 3 and n 4 are 0, and L 2 is connected to X, the formula II group is
  • formula III when formula III is attached to formula I, it refers to the main part of the group of formula III Linked to formula I via a single bond, formula I is not linked to R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 or R 10 as substituents in formula III.
  • X or Y is selected from N(R 7 ), and L 2 is linked to N(R 7 ) in formula III, R 7 is absent.
  • X is N(R 7 )
  • Y is a single bond
  • Z is O
  • the terms “optional” and “optionally” mean that the subsequently described event or circumstance can, but need not, occur, and that the description includes instances where the event or circumstance does or does not occur.
  • “optionally, two adjacent substituents form a ring;” means that the two substituents may but need not form a ring, including: scenarios where two adjacent substituents form a ring and two phases The case where the adjacent substituents do not form a ring.
  • any two adjacent R i and the benzene ring to which it is connected form a naphthalene ring or a phenanthrene ring means that any two adjacent R i can form a ring or not.
  • the new ring formed is a benzene ring or a naphthalene ring, that is, the adjacent R i and its connected benzene ring together form a naphthalene ring or a phenanthrene ring.
  • each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can be either It means that in different groups, the specific options expressed between the same symbols do not affect each other, 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
  • each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and its meaning is: formula Q-1 represents that there are 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 indicates that each benzene ring of biphenyl has q substituents R", and the R" on the two benzene rings The number q of "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.
  • substituted or unsubstituted means that the functional group described after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as R x ).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rx or an unsubstituted aryl group.
  • substituent namely R x
  • R x can be, for example, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optionally independently selected from 0, 1, 2, 3, 4 or 5
  • the number of carbon atoms of a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then all carbon atoms in the arylene group and the substituents thereon are 12.
  • aryl 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. That is, unless otherwise stated, 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, Se and Si.
  • a biphenyl group, a terphenyl group, and a 9, 9- dimethyl fluorenyl group are all regarded as an aryl group in this application.
  • aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene base, Base et al.
  • the "substituted or unsubstituted aryl group" of the present application may contain 6-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-25, in other implementations For example, the number of carbon atoms in a substituted or unsubstituted aryl group may be 6-18.
  • the number of carbon atoms of a substituted or unsubstituted aryl group may also be 6, 12, 13, 14, 15, 18, 20, 24, 25 or 30
  • the number of carbon atoms can also be other numbers, which will not be listed here.
  • biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.
  • the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.
  • the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, 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, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted.
  • the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituent on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group
  • aryl groups as substituents include, but are not limited to: phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, dimethylfluorenyl, terphenyl, diphenylfluorenyl, Spirobifluorenyl.
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be B, O, N, P, Si, At least one of Se 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
  • thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds.
  • Heteroaryl of ring system type is the same as thienyl, furyl, phenanthroline, etc.
  • substituted or unsubstituted heteroaryl may contain 2-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3-25, in other In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12-24, and in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12-20 indivual.
  • the number of carbon atoms of a substituted or unsubstituted heteroaryl group may also be 2, 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 One or 30, of course, the number of carbon atoms can also be other numbers, which will not be listed here.
  • the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.
  • a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, 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. It should be understood that the 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.
  • heteroaryl groups as substituents include, but are not limited to: dibenzothienyl, dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, indolocarbazolyl, N- -(1-Naphthyl)carbazolyl, N-(2-naphthyl)carbazolyl, 9-(4-phenyl)carbazolyl, 9,9-dimethyl-9H-9-siliconfluorene.
  • the non-positioning connection keys involved It refers to a single bond extending from the ring system, which means that one end of the connecting bond can be connected to any position in the ring system through which the bond passes, 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, and the meanings it represents include such as the formula (f). -1)-Any possible connection mode 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)-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 an unpositioned link, and the meanings represented by the formula (Y-1)- Any possible connection mode shown by formula (Y-7).
  • the alkyl group with 1-10 carbon atoms may include straight-chain alkyl groups with 1-10 carbon atoms and branched-chain alkyl groups with 1-10 carbon atoms, and the number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.
  • alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl and the like.
  • halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
  • trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
  • cycloalkyl groups having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.
  • n 1 , n 2 , n 3 , and n 4 are each independently selected from 0.
  • the L and L 1 are independently selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms;
  • the substituents in L and L 1 are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, and aryl group with 6-12 carbon atoms.
  • substituents in the L and L 1 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl , Biphenyl.
  • the L and L 1 are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene radical, substituted or unsubstituted terphenylene.
  • the L and L 1 are independently selected from the group consisting of a single bond or the following groups:
  • the L 2 is selected from a single bond, a phenylene group, or a biphenylene group.
  • L 2 is selected from the group consisting of a single bond or the following groups:
  • the Ar 1 is selected from a substituted or unsubstituted aryl group with 6-20 carbon atoms and a substituted or unsubstituted heteroaryl group with 12-20 carbon atoms;
  • the substituent in the Ar 1 is selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, aryl group with 6-14 carbon atoms, 3 carbon atoms -6 trialkylsilyl groups.
  • substituents in the Ar 1 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, bi- Phenyl, dimethylfluorenyl, phenanthrenyl, terphenyl, trimethylsilyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.
  • the Ar 1 is selected from a substituted or unsubstituted group V, and the unsubstituted group V is selected from the group consisting of the following groups:
  • the substituted group V has one or more substituents, and the substituents in the substituted group V are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tertiary Butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, trimethylsilyl.
  • the Ar 1 is selected from the group consisting of the following groups:
  • the Ar 2 is selected from the formula II, the formula II is selected from the substituted or unsubstituted group V 1 , and the unsubstituted group V 1 is selected from the following groups.
  • the substituted group V 1 has one or more substituents, and the substituents in the substituted group V 1 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl.
  • the Ar 2 is selected from the formula III, the formula III is selected from the substituted or unsubstituted group V 2 , and the unsubstituted group V 2 is selected from the following groups.
  • the substituted group V 2 has one or more substituents, and the substituents in the substituted group V 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl base, tert-butyl, phenyl, naphthyl.
  • the Ar is selected from the group consisting of the following groups :
  • the nitrogen-containing compound is selected from the group consisting of the following compounds:
  • 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 application exemplarily provides a method for preparing nitrogen-containing compounds, and the raw materials used can be obtained commercially or by methods well known in the art.
  • Those skilled in the art can obtain all nitrogen-containing compounds provided in 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.
  • a second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the first aspect of the present application. of nitrogenous compounds.
  • the nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer, so as to improve the efficiency characteristics and lifetime characteristics of the organic electroluminescent device.
  • the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound.
  • the organic light-emitting layer may include a host material and a guest material, wherein the host material includes the nitrogen-containing compound of the present application.
  • the organic electroluminescence device is a green organic electroluminescence device.
  • the organic electroluminescent device may include an anode 100 , a first hole transport layer 321 , a second hole transport layer 322 , an organic light emitting layer 330 serving as an energy conversion layer, and an electron transport layer 340 , which are stacked in sequence. and cathode 200.
  • 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: 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 (IZO); Combined metals and oxides such as ZnO:Al or SnO2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.
  • ITO indium tin oxide
  • the first hole transport layer 321 and the second hole transport layer 322 respectively include one or more hole transport materials, and the hole transport materials can be selected from carbazole polymers, carbazole-linked triarylamines compounds or other types of compounds.
  • the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the host material of the organic light-emitting layer 330 may contain the nitrogen-containing compound of the present application.
  • the organic light-emitting layer 330 is composed of a host material and a guest material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy. To the host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the guest material of the organic 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, which are not specially made in this application. limit.
  • the organic electroluminescent device is a green organic electroluminescent device, wherein the organic light-emitting layer 330 may be composed of the nitrogen-containing compound provided in this application; or, the organic light-emitting layer 330 may be composed of a Nitrogen-containing compounds are provided in combination with other materials.
  • 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-06 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 comprising magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting holes into the first 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 specifically limited in this application.
  • 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 and alkali metal halide, or may include a complex compound of alkali metal and organic matter.
  • a third aspect of the present application provides an electronic device, including the electronic component described in the second aspect of the present application.
  • the electronic device is an electronic device 400
  • the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the 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 compounds of the synthetic methods not mentioned in this application are all raw materials obtained through commercial channels.
  • the analytical detection of the intermediates and compounds in this application uses an ICP-7700 mass spectrometer.
  • reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane (50 mL) and water (50 mL) and washed with water three times each. The organic layer was dried over anhydrous magnesium sulfate and filtered. After filtration, the filtrate was passed through a short silica gel column and reduced pressure. The solvent was removed, and the obtained crude product was purified by recrystallization using dichloromethane/n-heptane system (volume ratio 1:3) to obtain intermediate Q-3 (6.9 g, 73%).
  • Raw material IM-1 (6.65 g, 29.4 mmol), raw material IM-2 (5.0 g, 23.6 mmol), tetrakis(triphenylphosphonium) palladium (1.7 g, 1.47 mmol), potassium carbonate (8.14 g, 58.9 mmol) , tetrabutylammonium chloride (0.41g, 1.47mmol) were respectively added to the three-necked flask, tetrahydrofuran (200mL) and water (40mL) were weighed and added to the reactor, refluxed at 80°C for 12h, when the reaction was over, dichloride was used.
  • the intermediate M-X in Table 1 was synthesized with reference to the method of intermediate M-1, except that the raw material A was used to replace the raw material IM-1, and the raw material B was used to replace the raw material IM-2.
  • the obtained intermediate M-X is shown in Table 1.
  • the intermediate N-X in Table 2 was synthesized with reference to the method of intermediate N-1, except that the raw material A was used to replace the raw material IM-1, and the raw material C was used to replace the raw material IM-17.
  • the obtained intermediate N-X is shown in Table 2.
  • the intermediate B-X in Table 3 was synthesized according to the method of intermediate B-1, except that the raw material SM-X in Table 3 was used instead of SM-1, and the prepared B-X was shown in Table 3.
  • the intermediate C-X in Table 4 is synthesized with reference to the method of intermediate C-1, the difference is that the raw material M-X/N-X in Table 4 is used to replace M-1, the raw material J-X is used to replace the raw material J-1, and the obtained intermediate C-X is as shown in the table 4 shown.
  • the compound X in Table 5 was synthesized according to the method of compound 1024, except that the raw material M-X/N-X was used instead of M-1, and the raw material S-X/B-X was used instead of S-1.
  • the prepared compound X is shown in Table 5.
  • serial number Compound code mass spectrometry serial number Compound code mass spectrometry 1 1024 491.3 2 1061 567.3 3 1062 567.3 4 1098 643.2 5 1097 643.2 6 1042 567.3 7 1043 567.3 8 1079 567.3 9 803 507.3 10 1118 507.3 11 1150 583.2 12 1188 659.3 13 1028 583.3 14 1208 583.3 15 1249 583.3 16 363 507.2 17 364 533.2 18 626 491.3 19 816 490.3 20 805 491.3 twenty one 807 523.3 twenty two 942 506.2 twenty three 946 655.2 twenty four 1035 655.3 25 1129 747.2 26 179 642.3 27 939 507.3 28 707 731.3 29 451 609.2 30 1034 566.2 31 245 642.3 32 178 599.3 33 1151 583.3 34 1153 599.3 35 563 583.2 36 1194 675.2 37 1045 583.3 38 1234 599.3 39 1100 659.3 40 1006 643.3 41 158 643.2 42 452
  • Anodes were prepared by the following process: ITO thickness was The substrate (manufactured by Corning) was cut into a size of 40mm x 40mm x 0.7mm, and a photolithography process was used to prepare it into an experimental substrate with cathode, anode and insulating layer patterns. UV ozone and O 2 : N 2 plasma were used for surface treatment. Treatment to increase the work function of the anode (experimental substrate) and to remove scum.
  • Compound HTL-1 was vacuum evaporated on the first hole transport layer to form a thickness of the second hole transport layer.
  • ET-06 and LiQ were mixed at a weight ratio of 1:1 and evaporated to form Thick electron transport layer (ETL), Yb 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 cathode is The CP-05 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 electroluminescent device was fabricated by the same method as in Example 1, except that the compounds shown in Table 9 below were used instead of Compound 1024 in forming the organic light-emitting layer.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A, Compound B, Compound C, Compound D, and Compound E in Table 9 were used instead of Compound 1024 when forming the organic light-emitting layer.

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Abstract

本申请涉及一种含氮化合物以及使用其的电子元件和电子装置，所述有机化合物具有如下式(I)所示的结构。本申请的含氮化合物能够显著降低器件的驱动电压，提高器件使用寿命；此外，本申请的含氮化合物还可提高器件的效率。

Description

一种含氮化合物以及使用其的电子元件和电子装置
相关申请的交叉引用
本申请要求于2020年12月11日递交的申请号为202011460044.4的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请涉及有机材料技术领域，具体地，涉及一种含氮化合物以及使用其的电子元件和电子装置。
背景技术
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。
目前，有机电致发光器件的使用过程中存在发光效率降低和寿命缩短等问题，导致有机电致发光器件的性能下降。
发明内容
针对现有技术存在的上述问题，本申请的目的在于提供一种含氮化合物以及使用其的电子元件和电子装置，该含氮化合物可用于有机电致发光器件中，提高有机电致发光器件的性能。
为了实现上述目的，本申请第一方面提供一种含氮化合物，所述有机化合物具有如下式I所示的结构：
Figure PCTCN2021130172-appb-000001
其中，T 1选自O或S；
L、L 1相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
L 2选自单键、碳原子数为6-20的取代或未取代的亚芳基；
Ar 1选自碳原子数为6-30的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
Ar 2选自式Ⅱ或式Ⅲ所示的结构；
其中，X、Y分别独立地选自单键、O、S、C(R 5R 6)或者N(R 7)，且X，Y不同时为单键；
R 5、R 6和R 7相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
Z选自O、S、C(R 8R 9)或者N(R 10)；
R 8、R 9和R 10相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
任选地，任意R 5和R 6、R 8和R 9与它们共同连接的原子形成碳原子数为3-14的饱和或不饱和环；
R 1、R 2、R 3和R 4相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-20的芳基、碳原子数为3-24的杂芳基；
R 1-R 4以R i表示，n 1-n 4以n i表示，i为变量，表示1、2、3或4，n 1、n 2、n 3和n 4分别表示R 1、R 2、R 3和R 4的个数；
其中，当i为1时，n i选自0、1、2或者3；当i为2、3或者4时，n i选自0、1、2、3或者4；
且当n i大于1时，任意两个n i相同或不同；
任选地，任意两个相邻的R i与其相连的苯环形成萘环或菲环；
L 2中的取代基选自氘、卤素基团、氰基、苯基；
L、L 1、Ar 1和R 5-R 10中的取代基相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、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3-10的环烷基，碳原子数为2-10的杂环烷基，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。
本申请第二方面提供一种电子元件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的含氮化合物；
优选地，所述功能层包括有机发光层，所述有机发光层包括所述含氮化合物；
更优选地，所述有机发光层包含主体材料和客体材料，所述主体材料包含所述含氮化合物。
本申请第三方面提供一种电子装置，所述电子装置包括本申请第二方面所述的电子元件。
本申请的含氮化合物能够显著降低器件的驱动电压，提高器件使用寿命；此外，本申请的含氮化合物还可提高器件的发光效率。
本申请提供的含氮化合物以氮杂二苯并呋喃/二苯并噻吩与三嗪作为核心基团，并以富电子的稠合杂芳基作为三嗪上的固定取代基团。其中，单氮杂二苯并呋喃/二苯并噻吩具备高的电子迁移率，与缺电子的三嗪基团相结合，可以有效提升材料的电子注入与传输能力；在此基础上，将富电子的稠合杂芳基连接在三嗪上，可有效提升分子极性，从而进一步提升材料的电子传输能力。其次，本申请化合物具备较高的T1值，特别适用于有机电致发光器件的主体材料，尤其是绿光主体材料。将本申请化合物用于有机电致发光器件的发光层材料时，将有效提升器件的电子传输性能，从而增强空穴与电子注入的平衡程度，改善器件发光效率以及使用寿命。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图说明
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、有机发光层；340、电子传输层；350、电子注入层；400、电子装置。
具体实施方式
以下结合附图对本申请的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本申请，并不用于限制本申请。
第一方面，本申请提供一种含氮化合物，所述含氮化合物具有如下式I所示的结构：
Figure PCTCN2021130172-appb-000002
其中，T 1选自O或S；
L、L 1相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
L 2选自单键、碳原子数为6-20的取代或未取代的亚芳基；
Ar 1选自碳原子数为6-30的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
Ar 2选自式Ⅱ或式Ⅲ所示的结构；
其中，X、Y分别独立地选自单键、O、S、C(R 5R 6)或者N(R 7)，且X，Y不同时为单键；
R 5、R 6和R 7相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
Z选自O、S、C(R 8R 9)或者N(R 10)；
R 8、R 9和R 10相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
任选地，任意R 5和R 6、R 8和R 9与它们共同连接的原子形成碳原子数为3-14的饱和或不饱和环；
R 1、R 2、R 3和R 4相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-20的未取代的芳基、碳原子数为3-24的未取代的杂芳基；
R 1-R 4以R i表示，n 1-n 4以n i表示，i为变量，表示1、2、3或4，n 1、n 2、n 3和n 4分别表示R 1、R 2、R 3和R 4的个数；
其中，当i为1时，n i选自0、1、2或者3；
当i为2、3或者4时，n i选自0、1、2、3或者4；
且当n i大于1时，任意两个n i相同或不同；
任选地，任意两个相邻的R i与其相连的苯环形成萘环或菲环；
L 2中的取代基选自氘、卤素基团、氰基、苯基；
L、L 1、Ar 1和R 5-R 10中的取代基相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、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3-10的环烷基，碳原子数为2-10的杂环烷基，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，当式Ⅱ与式Ⅰ连接时，指的是式Ⅱ基团的主体部分
Figure PCTCN2021130172-appb-000003
与式Ⅰ通过单键连接，式Ⅰ中L 2并不与式Ⅱ中作为取代基的R 3、R 4、R 5、R 6或R 7连接。应当明确的是，当X或Y 选自N(R 7)，且L 2与式Ⅱ中的N(R 7)连接时，R 7不存在。比如，X为N(R 7)，Y为O，n 3和n 4为0，L 2连接于X上时，式Ⅱ基团为
Figure PCTCN2021130172-appb-000004
同理，当式Ⅲ与式Ⅰ连接时，指的是式Ⅲ基团的主体部分
Figure PCTCN2021130172-appb-000005
与式Ⅰ通过单键连接，式Ⅰ并不与式Ⅲ中作为取代基的R 3、R 4、R 5、R 6、R 7、R 8、R 9或R 10连接。当X或Y选自N(R 7)，L 2与式Ⅲ中N(R 7)连接时，R 7不存在。举例而言，X为N(R 7)，Y为单键，Z为O时，式Ⅲ基团为
Figure PCTCN2021130172-appb-000006
在本申请中，术语“任选”、“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，两个相邻取代基形成环；”意味着这两个取代基可以形成环但不是必须形成环，包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。
在本申请中，“任选地，任意两个相邻的R i与其相连的苯环形成萘环或菲环”是指任意两个相邻的R i可以形成环，也可以不形成环。举例而言，当相邻的R i成环时，所形成的新环为苯环或萘环，即相邻的R i与其相连的苯环共同形成萘环或菲环。
在本申请中，所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，“
Figure PCTCN2021130172-appb-000007
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为R x)。例如，“取代或未取代的芳基”是指具有取代基R x的芳基或者非取代的芳基。其中上述的取代基即R x例如可以为氘，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个独立选自氘、氟、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3-10的环烷基，碳原子数为2-10的杂环烷基，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的芳氧基，碳原子数为6-18的芳硫基，碳原子数为6-18的膦氧基；当同一个原子上连接有两个取代基R x时，这两个取代基R x可以独立地存在或者相互连接以与所述原子形成螺环；当官能团上存在两个相邻的取代基R x时，相邻的个取代基R x可以独立地存在或者与其所连接的官能团稠合成环。
在本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L选自取代的碳原子数为12的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳 基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。需要说明地是，联苯基、三联苯基、9,9-二甲基芴基在本申请中均视为芳基。芳基的具体实例包括但不限于，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 PCTCN2021130172-appb-000008
基等。本申请的“取代或未取代的芳基”可含有6-30个碳原子，在一些实施例中，取代或未取代的芳基中的碳原子数可以是6-25个，在另一些实施例中，取代或未取代的芳基中的碳原子数可以是6-18个。举例而言，本申请中，取代或未取代的芳基的碳原子数还可以是6个、12个、13个、14个、15个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。在本申请中，联苯基可以理解为苯基取代的芳基，也可以理解为未取代的芳基。
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、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。应当理解地是，取代的芳基的碳原子数，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。
在本申请中，作为取代基的芳基具体实例包括但不限于：苯基、联苯基、萘基、菲基、蒽基、二甲基芴基、三联苯基、二苯基芴基、螺二芴基。
在本申请中，杂芳基是指环中包含1、2、3、4、5或6个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的至少一种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳键共轭连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、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-(1-萘基)咔唑基、N-(2-萘基)咔唑基、9-(4-苯基苯基)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。本申请的“取代或未取代的杂芳基”可含有2-30个碳原子，在一些实施例中，取代或未取代的杂芳基中的碳原子数可以是3-25个，在另一些实施例中，取代或未取代的杂芳基中的碳原子数可以是12-24个，在另一些实施例中，取代或未取代的杂芳基中的碳原子数可以是12-20个。举例而言，取代或未取代的杂芳基的碳原子数还可以是2个、3个、4个、5个、7个、12个、13个、18个、20个、24个、25个或30个，当然，碳原子数还可以是其他数量，在此不再一一列举。
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、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、烷氧基、烷硫基等基团取代。芳基取代的杂芳基的具体实例包括但不限于，苯基取代的二苯并呋喃基、苯基取代的二苯并噻吩基、苯基取代的吡啶基等。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基具体实例包括但不限于：二苯并噻吩基、二苯并呋喃基、咔唑基、N-苯基咔唑基、吲哚咔唑基、N-(1-萘基)咔唑基、N-(2-萘基)咔唑基、9-(4-苯基)咔唑基、9,9-二甲基-9H-9-硅芴。
本申请中，涉及到的不定位连接键
Figure PCTCN2021130172-appb-000009
是指从环体系中伸出的单键，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它位置连接，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 PCTCN2021130172-appb-000010
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 PCTCN2021130172-appb-000011
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 PCTCN2021130172-appb-000012
在本申请中，碳原子数为1-10的烷基可以包括碳原子数1-10的直链烷基和碳原子数为1-10的支链烷基，碳原子数例如可以为1、2、3、4、5、6、7、8、9、10。碳原子数为1-10的烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、环戊基、正己基、庚基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
在本申请中，卤素基团可以包括氟、碘、溴、氯等。
在本申请中，碳原子数为3-12的三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。
在本申请中，碳原子数为3-10的环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基等。
在本申请的一种实施方式中，所述n 1、n 2、n 3、n 4分别独立地选自0。
在本申请的一种实施方式中，所述L、L 1分别独立地选自单键、碳原子数为6-20的取代或未取代的亚芳基；
可选地，所述L、L 1中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-12的芳基。
具体地，所述L、L 1中的取代基具体实例包括但不限于：氘、氟、氰基、甲基、乙基、正丙基、 异丙基、叔丁基、苯基、萘基、联苯基。
在本申请另一种实施方式中，所述L、L 1分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基。
在本申请的一种实施方式中，所述L、L 1分别独立地选自单键或如下基团组成的组：
Figure PCTCN2021130172-appb-000013
在本申请的一种实施方式中，所述L 2选自单键、亚苯基，或者亚联苯基。
在本申请一种实施方式中，L 2选自单键或如下基团组成的组：
Figure PCTCN2021130172-appb-000014
在本申请的一种实施方式中，所述Ar 1选自碳原子数6-20的取代或未取代的芳基、碳原子数为12-20的取代或未取代的杂芳基；
可选地，所述Ar 1中的取代基选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-14的芳基、碳原子数为3-6的三烷基硅基。
具体地，所述Ar 1中的取代基具体实例包括但不限于：氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、二甲基芴基、菲基、三联苯基、三甲基硅基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基。
在本申请中，可选地，所述Ar 1选自取代或未取代的基团V，所述未取代的基团V选自以下基团组成的组：
Figure PCTCN2021130172-appb-000015
取代的基团V具有一个或两个以上取代基，取代的基团V中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、三联苯基、三甲基硅基。
在本申请的一种实施方式中，所述Ar 1选自以下基团组成的组：
Figure PCTCN2021130172-appb-000016
Figure PCTCN2021130172-appb-000017
在本申请的一种实施方式中，所述Ar 2选自式Ⅱ，所述式Ⅱ选自取代或未取代的基团V 1，未取代的基团V 1选自以下基团所组成的组：
Figure PCTCN2021130172-appb-000018
取代的基团V 1具有一个或两个以上取代基，取代的基团V 1中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
在本申请的一种实施方式中，所述Ar 2选自式Ⅲ，所述式Ⅲ选自取代或未取代的基团V 2，未取代的基团V 2选自以下基团所组成的组：
Figure PCTCN2021130172-appb-000019
Figure PCTCN2021130172-appb-000020
取代的基团V 2中具有一个或两个以上取代基，取代的基团V 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
可选地，所述Ar 2选自以下基团所组成的组：
Figure PCTCN2021130172-appb-000021
Figure PCTCN2021130172-appb-000022
在本申请中，可选地，所述含氮化合物选自如下化合物组成的组：
Figure PCTCN2021130172-appb-000023
Figure PCTCN2021130172-appb-000024
Figure PCTCN2021130172-appb-000025
Figure PCTCN2021130172-appb-000026
Figure PCTCN2021130172-appb-000027
Figure PCTCN2021130172-appb-000028
Figure PCTCN2021130172-appb-000029
Figure PCTCN2021130172-appb-000030
Figure PCTCN2021130172-appb-000031
Figure PCTCN2021130172-appb-000032
Figure PCTCN2021130172-appb-000033
Figure PCTCN2021130172-appb-000034
Figure PCTCN2021130172-appb-000035
Figure PCTCN2021130172-appb-000036
Figure PCTCN2021130172-appb-000037
Figure PCTCN2021130172-appb-000038
Figure PCTCN2021130172-appb-000039
Figure PCTCN2021130172-appb-000040
Figure PCTCN2021130172-appb-000041
Figure PCTCN2021130172-appb-000042
Figure PCTCN2021130172-appb-000043
Figure PCTCN2021130172-appb-000044
Figure PCTCN2021130172-appb-000045
Figure PCTCN2021130172-appb-000046
Figure PCTCN2021130172-appb-000047
Figure PCTCN2021130172-appb-000048
Figure PCTCN2021130172-appb-000049
Figure PCTCN2021130172-appb-000050
Figure PCTCN2021130172-appb-000051
Figure PCTCN2021130172-appb-000052
Figure PCTCN2021130172-appb-000053
Figure PCTCN2021130172-appb-000054
Figure PCTCN2021130172-appb-000055
Figure PCTCN2021130172-appb-000056
Figure PCTCN2021130172-appb-000057
Figure PCTCN2021130172-appb-000058
Figure PCTCN2021130172-appb-000059
Figure PCTCN2021130172-appb-000060
Figure PCTCN2021130172-appb-000061
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，本申请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。
本申请第二方面提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含本申请第一方面所述的含氮化合物。
本申请所提供的含氮化合物可以用于形成功能层中的至少一个有机膜层，以改善有机电致发光器件的效率特性和寿命特性。
具体的一种实施方式中，所述功能层包括有机发光层，所述有机发光层包括所述含氮化合物。通常地，所述有机发光层可以包含主体材料和客体材料，其中，所述主体材料包含本申请的含氮化合物。
按照本申请的一种实施方式中，所述有机电致发光器件为绿色有机电致发光器件。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、第一空穴传输层321、第二空穴传输层322、作为能量转化层的有机发光层330、电子传输层340和阴极200。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，第一空穴传输层321和第二空穴传输层322分别包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物。
可选地，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。有机发光层330的主体材料可以含有本申请的含氮化合物。进一步可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。有机发光层330的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。
按照一种具体的实施方式，所述有机电致发光器件为绿色有机电致发光器件，其中的有机发光层330可以由本申请所提供的含氮化合物组成；或者，有机发光层330可以由本申请所提供的含氮化合物和其他材料共同组成。
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、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料。在本申请的一种示例性实施方式中，电子传输层340可以由ET-06和LiQ组成。
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310，以增强向第一空穴传输层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。
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、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。
本申请第三方面提供一种电子装置，包含本申请第二方面所述的电子元件。
按照一种实施方式，如图2所示，所述电子装置为电子装置400，该电子装置400包括上述有机电致发光器件。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。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
本申请中的中间体和化合物的分析检测使用ICP-7700质谱仪。
下面结合合成实施例来具体说明本申请的含氮化合物的合成方法。
使用以下方法合成本申请中化合物
Figure PCTCN2021130172-appb-000062
向反应瓶中投入Q-1(5.0g，19.5mmol)、Q-2(6.03g，19.5mmol)、三(二亚苄基丙酮)二钯(0.18g，0.19mmol)、2-二环己基膦-2’,6’-二甲氧基-联苯(0.16g，0.39mmol)、叔丁醇钠(5.62g，58.5mmol)和甲苯(50mL)，氮气保护下升温至110℃，加热回流搅拌8h。反应液冷却至室温后，用二氯甲烷(50mL)和水(50mL)萃取和水洗反应溶液各3次，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，所得粗品使用二氯甲烷/正庚烷体系(体积比1:3)进行重结晶提纯，得到中间体Q-3(6.9g，73％)。
Figure PCTCN2021130172-appb-000063
将原料IM-1(6.65g，29.4mmol)、原料IM-2(5.0g，23.6mmol)、四(三苯基磷)钯(1.7g，1.47mmol)、碳酸钾(8.14g，58.9mmol)、四丁基氯化铵(0.41g，1.47mmol)分别加入三口烧瓶中，量取四氢呋喃(200mL)、水(40mL)加入反应器中，80℃下回流12h，当反应结束时，使用二氯甲烷和水进行萃取，取有机相用无水MgSO 4干燥，抽滤，浓缩有机层，所得粗产物经硅胶过柱提纯，得到中间体M-1(7.9g，产率75％)。
参照中间体M-1的方法合成表1中中间体M-X，不同之处在于，使用原料A代替原料IM-1，原料B代替原料IM-2，制得的中间体M-X如表1所示。
表1
Figure PCTCN2021130172-appb-000064
Figure PCTCN2021130172-appb-000065
Figure PCTCN2021130172-appb-000066
Figure PCTCN2021130172-appb-000067
Figure PCTCN2021130172-appb-000068
Figure PCTCN2021130172-appb-000069
中间体N的合成
Figure PCTCN2021130172-appb-000070
在反应瓶中，加入原料IM-17(5.0g，20.6mmol)和N,N-二甲基甲酰胺(50mL),在氮气氛围下，降温至0℃后，加入钠氢(0.54g，22.6mmol)，保温30min后加入原料IM-1(6.9g，30.9mmol)，升温至室温反应2小时。当反应结束时，使用二氯甲烷和水进行萃取，取有机相用无水MgSO 4干燥，抽滤，浓缩有机层，所得粗产物经硅胶过柱提纯，得到中间体N-1(4.4g，产率60％)。
参照中间体N-1的方法合成表2中中间体N-X，不同之处在于，使用原料A代替原料IM- 1，原料C代替原料IM-17，制得的中间体N-X如表2所示。
表2
Figure PCTCN2021130172-appb-000071
Figure PCTCN2021130172-appb-000072
Figure PCTCN2021130172-appb-000073
中间体B-1的合成
Figure PCTCN2021130172-appb-000074
向干燥并经过氮气置换的圆底烧瓶中，加入SM-1(5.0g，18.92mmol)，四氢呋喃(400mL)，降温至零下78℃后滴加正丁基锂(1.5g，22.7mmol)，滴加完毕在零下78℃保温30min后滴加硼酸三甲酯(5.9g，56.8mmol)，滴加完毕在零下78℃保温30min。升温至室温搅拌12h后加入浓盐酸调节至pH＝7。析出固体，过滤得到粗品，将粗品用正庚烷(600mL)重结晶得到中间体B-1(2.6g，产率60％)。
参照中间体B-1的方法合成表3中中间体B-X，不同之处在于，使用表3中原料SM-X代替SM-1，制得的B-X如表3所示。
表3
Figure PCTCN2021130172-appb-000075
中间体C-1的合成：
Figure PCTCN2021130172-appb-000076
将原料M-1(5.0g，13.97mmol)、原料J-1(2.18g，13.97mmol)、四(三苯基磷)钯(0.08g，0.07mmol)、碳酸钾(3.86g，27.95mmol)、四丁基氯化铵(0.02g，0.07mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)、水(10mL)加入反应器中，80℃下回流12h，当反应结束时，使用二氯甲烷和水进行萃取，有机相用无水MgSO 4干燥，抽滤，浓缩有机层，所得粗产物经硅胶柱提纯，得到中间体C-1(4.67g，产率77％)。
参照中间体C-1的方法合成表4中中间体C-X，不同之处在于，使用表4中原料M-X/N-X代替M-1，原料J-X代替原料J-1，制得的中间体C-X如表4所示。
表4
Figure PCTCN2021130172-appb-000077
Figure PCTCN2021130172-appb-000078
化合物1024的合成
Figure PCTCN2021130172-appb-000079
将M-1(5.0g，13.9mmol)、S-1(2.9g，13.9mmol)、四(三苯基磷)钯(0.8g，0.69mmol)、碳酸钾(3.8g，0.69mmol)、四丁基氯化铵(0.19g，0.69mmol)分别加入三口烧瓶中，量取甲苯(40mL)、乙醇(20mL)和水(10mL)加入反应器中，78℃下回流12h，当反应结束时，使用二氯甲烷和水进行萃取，有机相用无水MgSO 4干燥，抽滤，浓缩有机层，所得粗产物硅胶过柱提纯，得到化合物1024(4.79g，产率70％)。
参照化合物1024的方法合成表5中化合物X，不同之处在于，使用原料M-X/N-X代替M-1，原料S-X/B-X代替S-1，制得的化合物X如表5所示。
表5
Figure PCTCN2021130172-appb-000080
Figure PCTCN2021130172-appb-000081
Figure PCTCN2021130172-appb-000082
Figure PCTCN2021130172-appb-000083
Figure PCTCN2021130172-appb-000084
Figure PCTCN2021130172-appb-000085
Figure PCTCN2021130172-appb-000086
Figure PCTCN2021130172-appb-000087
Figure PCTCN2021130172-appb-000088
Figure PCTCN2021130172-appb-000089
Figure PCTCN2021130172-appb-000090
Figure PCTCN2021130172-appb-000091
Figure PCTCN2021130172-appb-000092
Figure PCTCN2021130172-appb-000093
对以上化合物进行质谱分析，数据如下表6所示。
表6
序号 化合物编码 质谱 序号 化合物编码 质谱
1 1024 491.3 2 1061 567.3
3 1062 567.3 4 1098 643.2
5 1097 643.2 6 1042 567.3
7 1043 567.3 8 1079 567.3
9 803 507.3 10 1118 507.3
11 1150 583.2 12 1188 659.3
13 1028 583.3 14 1208 583.3
15 1249 583.3 16 363 507.2
17 364 533.2 18 626 491.3
19 816 490.3 20 805 491.3
21 807 523.3 22 942 506.2
23 946 655.2 24 1035 655.3
25 1129 747.2 26 179 642.3
27 939 507.3 28 707 731.3
29 451 609.2 30 1034 566.2
31 245 642.3 32 178 599.3
33 1151 583.3 34 1153 599.3
35 563 583.2 36 1194 675.2
37 1045 583.3 38 1234 599.3
39 1100 659.3 40 1006 643.3
41 158 643.2 42 452 583.2
43 668 642.3 44 393 567.3
45 845 642.3 46 960 747.3
47 1216 747.3 48 1204 748.2
49 1050 566.3 50 1138 582.3
51 907 731.2 52 1087 566.3
53 1192 659.3 54 1219 747.2
55 1108 807.2 56 1052 731.3
57 1109 807.3 58 858 747.2
59 860 672.3 60 913 643.2
61 1266 580.2 62 1267 807.3
63 1271 516.2 64 1272 547.2
65 1273 508.2 66 1274 687.4
67 1275 583.2 68 1276 643.2
69 1277 675.2 70 1278 719.2
71 1279 642.2 72 1287 496.2
73 1288 589.2      
对以上个别化合物进行核磁分析，数据如下表7所示。
表7
Figure PCTCN2021130172-appb-000094
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 PCTCN2021130172-appb-000095
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 PCTCN2021130172-appb-000096
的空穴注入层(HIL)，并且在空穴注入层蒸镀NPB，形成厚度为
Figure PCTCN2021130172-appb-000097
的第一空穴传输层。
在第一空穴传输层上真空蒸镀化合物HTL-1，形成厚度为
Figure PCTCN2021130172-appb-000098
的第二空穴传输层。
在第二空穴传输层上，以(1：1)(蒸镀速率)的比例将(GH-1：化合物1024)与8％(占比主体材料总蒸镀速率)的客体材料Ir(ppy) 3以进行共同蒸镀，形成厚度为
Figure PCTCN2021130172-appb-000099
的绿色有机发光层(EML)。
将ET-06和LiQ以1:1的重量比进行混合并蒸镀形成了
Figure PCTCN2021130172-appb-000100
厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为
Figure PCTCN2021130172-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 PCTCN2021130172-appb-000102
的阴极。
在上述阴极上蒸镀厚度为
Figure PCTCN2021130172-appb-000103
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2-73
除了在形成有机发光层时，用以下表9中所示的化合物替代化合物1024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1-5
除了在形成有机发光层时，分别用以下表9中化合物A、化合物B、化合物C、化合物D和化合物E替代化合物1024以外，利用与实施例1相同的方法制作有机电致发光器件。
以上实施例和比较例使用的材料结构如下所示表8所示。
表8
Figure PCTCN2021130172-appb-000104
Figure PCTCN2021130172-appb-000105
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9所示。
表9
Figure PCTCN2021130172-appb-000106
Figure PCTCN2021130172-appb-000107
Figure PCTCN2021130172-appb-000108
根据上述表9的结果可知，采用本申请的含氮化合物作为有机发光层的实施例1-73与使用已公知的化合物比较例1-5相比，本申请中的有机电致发光器件的驱动电压至少降低了0.19V，发光效率(Cd/A)至少提高了11.74％，功率效率(lm/W)至少提高了18.68％，外量子效率至少提高了11.73％，寿命至少提高了6.74％，最高提升114h。
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。

Claims (12)

  1. 一种含氮化合物，其特征在于，所述含氮化合物具有如下式I所示的结构：
    Figure PCTCN2021130172-appb-100001
    其中，T 1选自O或S；
    L、L 1相同或不同，且各自独立地选自单键、碳原子数为6-30的取代或未取代的亚芳基、碳原子数为3-30的取代或未取代的亚杂芳基；
    L 2选自单键、碳原子数为6-20的取代或未取代的亚芳基；
    Ar 1选自碳原子数为6-30的取代或未取代的芳基，或者碳原子数为2-30的取代或未取代的杂芳基；
    Ar 2选自式Ⅱ或式Ⅲ所示的结构；
    其中，X、Y分别独立地选自单键、O、S、C(R 5R 6)或者N(R 7)，且X、Y不同时为单键；
    R 5、R 6和R 7相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
    Z选自O、S、C(R 8R 9)或者N(R 10)；
    R 8、R 9和R 10相同或不同，且各自独立地选自碳原子数为1-10的烷基、碳原子数为6-25的取代或未取代的芳基，或者碳原子数为3-30的取代或未取代的杂芳基；
    任选地，任意R 5和R 6、R 8和R 9与它们共同连接的原子形成碳原子数为3-14的饱和或不饱和环；
    R 1、R 2、R 3和R 4相同或不同，且各自独立地选自氘、卤素基团、碳原子数为1-10的烷基、碳原子数为3-10的环烷基、碳原子数为6-20的芳基、碳原子数为3-24的杂芳基；
    R 1-R 4以R i表示，n 1-n 4以n i表示，i为变量，表示1、2、3或4，n 1、n 2、n 3和n 4分别表示R 1、R 2、R 3和R 4的个数；
    其中，当i为1时，n i选自0、1、2或者3；
    当i为2、3或者4时，n i选自0、1、2、3或者4；
    且当n i大于1时，任意两个n i相同或不同；
    任选地，任意两个相邻的R i与其相连的苯环形成萘环或菲环；
    L 2中的取代基选自氘、卤素基团、氰基、苯基；
    L、L 1、Ar 1和R 5-R 10中的取代基相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立选自氘、氟、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3-10的环烷基，碳原子数为2-10的杂环烷基，碳原子数为1-10的烷氧基，碳原子数为1-0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L、L 1分别独立地选自单键、碳原子数为6-20的取代或未取代的亚芳基；
    优选地，所述L、L 1中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为1-5的烷基、 碳原子数为6-12的芳基。
  3. 根据权利要求1所述的含氮化合物，其特征在于，所述L、L 1分别独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基；
    优选地，所述L、L 1中的取代基分别独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、联苯基。
  4. 根据权利要求1所述的含氮化合物，其特征在于，所述L 2选自单键、亚苯基，或者亚联苯基。
  5. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1选自碳原子数6-20的取代或未取代的芳基、碳原子数为12-20的取代或未取代的杂芳基；
    优选地，所述Ar 1中的取代基选自氘、卤素基团、氰基、碳原子数为1-5的烷基、碳原子数为6-14的芳基、碳原子数为3-6的三烷基硅基。
  6. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1选自取代或未取代的基团V，所述未取代的基团V选自以下基团组成的组：
    Figure PCTCN2021130172-appb-100002
    取代的基团V具有一个或两个以上取代基，取代的基团V中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、菲基、三甲基硅基。
  7. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 2选自式Ⅱ，所述式Ⅱ选自取代或未取代的基团V 1，未取代的基团V 1选自以下基团所组成的组：
    Figure PCTCN2021130172-appb-100003
    Figure PCTCN2021130172-appb-100004
    取代的基团V 1具有一个或两个以上取代基，取代的基团V 1中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
  8. 根据权利要求1任意一项所述的含氮化合物，其特征在于，所述Ar 2选自式Ⅲ，所述式Ⅲ选自取代或未取代的基团V 2，未取代的基团V 2选自以下基团所组成的组：
    Figure PCTCN2021130172-appb-100005
    Figure PCTCN2021130172-appb-100006
    Figure PCTCN2021130172-appb-100007
    取代的基团V 2中具有一个或两个以上取代基，取代的基团V 2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基。
  9. 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组成的组：
    Figure PCTCN2021130172-appb-100008
    Figure PCTCN2021130172-appb-100009
    Figure PCTCN2021130172-appb-100010
    Figure PCTCN2021130172-appb-100011
    Figure PCTCN2021130172-appb-100012
    Figure PCTCN2021130172-appb-100013
    Figure PCTCN2021130172-appb-100014
    Figure PCTCN2021130172-appb-100015
    Figure PCTCN2021130172-appb-100016
    Figure PCTCN2021130172-appb-100017
    Figure PCTCN2021130172-appb-100018
    Figure PCTCN2021130172-appb-100019
    Figure PCTCN2021130172-appb-100020
    Figure PCTCN2021130172-appb-100021
    Figure PCTCN2021130172-appb-100022
    Figure PCTCN2021130172-appb-100023
    Figure PCTCN2021130172-appb-100024
    Figure PCTCN2021130172-appb-100025
    Figure PCTCN2021130172-appb-100026
    Figure PCTCN2021130172-appb-100027
    Figure PCTCN2021130172-appb-100028
    Figure PCTCN2021130172-appb-100029
    Figure PCTCN2021130172-appb-100030
    Figure PCTCN2021130172-appb-100031
    Figure PCTCN2021130172-appb-100032
    Figure PCTCN2021130172-appb-100033
    Figure PCTCN2021130172-appb-100034
    Figure PCTCN2021130172-appb-100035
    Figure PCTCN2021130172-appb-100036
    Figure PCTCN2021130172-appb-100037
    Figure PCTCN2021130172-appb-100038
    Figure PCTCN2021130172-appb-100039
    Figure PCTCN2021130172-appb-100040
    Figure PCTCN2021130172-appb-100041
    Figure PCTCN2021130172-appb-100042
    Figure PCTCN2021130172-appb-100043
    Figure PCTCN2021130172-appb-100044
    Figure PCTCN2021130172-appb-100045
    Figure PCTCN2021130172-appb-100046
    Figure PCTCN2021130172-appb-100047
  10. 一种电子元件，其特征在于，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层，所述功能层包含权利要求1-9中任意一项所述的含氮化合物；
    优选地，所述功能层包括有机发光层，所述有机发光层包括所述含氮化合物；
    更优选地，所述有机发光层包含主体材料和客体材料，所述主体材料包含所述含氮化合物。
  11. 根据权利要求10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；
    优选地，所述有机电致发光器件为绿色有机电致发光器件。
  12. 一种电子装置，其特征在于，包含权利要求10或11所述的电子元件。
PCT/CN2021/130172 2020-12-11 2021-11-11 一种含氮化合物以及使用其的电子元件和电子装置 WO2022121618A1 (zh)

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