WO2022160661A1 - 一种含氮化合物及包含其的电子元件和电子装置 - Google Patents

一种含氮化合物及包含其的电子元件和电子装置 Download PDF

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WO2022160661A1
WO2022160661A1 PCT/CN2021/112354 CN2021112354W WO2022160661A1 WO 2022160661 A1 WO2022160661 A1 WO 2022160661A1 CN 2021112354 W CN2021112354 W CN 2021112354W WO 2022160661 A1 WO2022160661 A1 WO 2022160661A1
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substituted
unsubstituted
group
carbon atoms
independently selected
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PCT/CN2021/112354
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French (fr)
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马天天
张孔燕
李昕轩
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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Priority to KR1020227010623A priority Critical patent/KR102466473B1/ko
Priority to US17/763,869 priority patent/US11618754B2/en
Priority to JP2022521207A priority patent/JP7307515B2/ja
Priority to EP21870531.7A priority patent/EP4063368A4/en
Publication of WO2022160661A1 publication Critical patent/WO2022160661A1/zh

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Definitions

  • the present application relates to the technical field of organic electroluminescence, and in particular, to a nitrogen-containing compound and electronic components and electronic devices containing the same.
  • organic electroluminescent material As a new generation of display technology, organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in flat panel display, flexible display, solid-state lighting and vehicle display industries.
  • the organic light-emitting phenomenon refers to a phenomenon in which an organic material is used to convert electrical energy into light energy.
  • An organic light-emitting device utilizing an organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is usually formed in a multi-layer structure composed of different materials to improve the brightness, efficiency and lifetime of the organic electroluminescent device.
  • the organic material layer can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, etc.
  • an organic light-emitting device structure when a voltage is applied between two electrodes, holes and electrons are injected into the organic material layer from the anode and cathode, respectively, excitons are formed when the injected holes meet electrons, and when these excitons return Lights up in the ground state.
  • the main problems are the lifespan and efficiency. With the large area of the display, the driving voltage also increases, the luminous efficiency and power efficiency also need to be improved, and a certain service life must be guaranteed. Therefore, organic materials must solve these efficiency or lifetime issues, and new materials with high efficiency, long lifetime and suitable for mass production for organic light-emitting devices need to be continuously developed.
  • the purpose of the present application is to overcome the above-mentioned deficiencies in the prior art, and to provide a nitrogen-containing compound and an electronic component and electronic device containing the same, which can improve the luminous efficiency and prolong the life of the device.
  • a nitrogen-containing compound is provided, and the general structural formula of the nitrogen-containing compound is shown in Formula 1:
  • a and B are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, formula 2
  • U 1 , U 2 and U 3 are the same or different, independently selected from N or C(R), and at least one of U 1 , U 2 and U 3 is N;
  • Each R, R 1 , R 2 , R 3 , R 4 , R 5 is independently selected from hydrogen, deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, 5- 12 heteroaryl, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, cycloalkyl with 3-10 carbon atoms;
  • n 1 represents the number of substituents R 1 , n 1 is selected from 1, 2 or 3, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of substituent R 2 , n 2 is selected from 1, 2, 3 or 4, when n 2 is greater than 1, any two R 2 are the same or different, optionally, any two adjacent R 2 2 form a ring;
  • n 3 represents the number of substituent R 3 , n 3 is selected from 1, 2, 3 or 4, when n 3 is greater than 1, any two R 3 are the same or different;
  • n 4 represents the number of substituent R 4 , n 4 is selected from 1 or 2, when n 4 is greater than 1, any two R 4 are the same or different;
  • n 5 represents the number of substituent R 5 , n 5 is selected from 1, 2, 3 or 4, when n 5 is greater than 1, any two R 5 are the same or different;
  • X is selected from S or O;
  • L, L 1 , L 2 , L 3 and L 4 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a 3-30 carbon atom group substituted or unsubstituted heteroarylene;
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in A, B, L, L 1 , L 2 , L 3 , L 4 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, carbon atom Heteroaryl group with 3-20 carbon atoms, aryl group with carbon number of 6-20, trialkylsilyl group with carbon number of 3-12, alkyl group with carbon number of 1-10, carbon number of 1-10 haloalkyl, 3-10 carbon cycloalkyl, 2-10 carbon heterocycloalkyl, 1-10 carbon alkoxy;
  • any two adjacent substituents form a ring.
  • the nitrogen-containing compound provided by the present application has the characteristics of polycyclic conjugation, the compound has the parent structure of fused indolocarbazole, and the bond energy between atoms is high, so it has good thermal stability and is conducive to intermolecular bonding. Solid-state stacking, exhibits long lifetimes as light-emitting layer materials in organic electroluminescent devices.
  • the nitrogen-containing compounds of the present application are respectively connected to nitrogen-containing groups (triazine, pyridine and pyrimidine) and benzoxazole or benzothiazole groups through an indolocarbazole structure, and the resulting structure has a high dipole moment, thereby increasing the polarity of the material.
  • the nitrogen-containing compound provided in the present application has a relatively high T 1 value, and is suitable for use as a host material for a light-emitting layer in an OLED device, especially a green light host material.
  • the compound of the present application is used as the light-emitting layer material of an organic electroluminescent device, the electron transport performance of the device will be effectively improved, thereby enhancing the balance of hole and electron transport, and improving the luminous efficiency and service life of the device.
  • an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the above-mentioned nitrogen-containing compound.
  • an electronic device including the above electronic component.
  • FIG. 1 is a schematic structural diagram of an embodiment of the organic electroluminescent device of the present application.
  • FIG. 2 is a schematic structural diagram of an embodiment of the electronic device 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.
  • a and B are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, formula 2
  • the structure shown in -1 or the structure shown in formula 2-2, and at least one of A and B is selected from the structure shown in formula 2-1 or formula 2-2;
  • U 1 , U 2 and U 3 are the same or different, independently selected from N or C(R), and at least one of U 1 , U 2 and U 3 is N;
  • Each R, R 1 , R 2 , R 3 , R 4 , R 5 is independently selected from hydrogen, deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, 5- 12 heteroaryl, alkyl with 1-5 carbon atoms, haloalkyl with 1-5 carbon atoms, cycloalkyl with 3-10 carbon atoms;
  • n 1 represents the number of substituents R 1 , n 1 is selected from 1, 2 or 3, when n 1 is greater than 1, any two R 1 are the same or different;
  • n 2 represents the number of substituent R 2 , n 2 is selected from 1, 2, 3 or 4, when n 2 is greater than 1, any two R 2 are the same or different, optionally, any two adjacent R 2 2 form a ring;
  • n 3 represents the number of substituent R 3 , n 3 is selected from 1, 2, 3 or 4, when n 3 is greater than 1, any two R 3 are the same or different;
  • n 4 represents the number of substituent R 4 , n 4 is selected from 1 or 2, when n 4 is greater than 1, any two R 4 are the same or different;
  • n 5 represents the number of substituent R 5 , n 5 is selected from 1, 2, 3 or 4, when n 5 is greater than 1, any two R 5 are the same or different; X is selected from S or O;
  • L, L 1 , L 2 , L 3 and L 4 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a 3-30 carbon atom group substituted or unsubstituted heteroarylene;
  • Ar 1 and Ar 2 are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;
  • the substituents in A, B, L, L 1 , L 2 , L 3 , L 4 , Ar 1 and Ar 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, carbon atom Heteroaryl group with 3-20 carbon atoms, aryl group with carbon number of 6-20, trialkylsilyl group with carbon number of 3-12, alkyl group with carbon number of 1-10, carbon number of 1-10 haloalkyl, 3-10 carbon cycloalkyl, 2-10 carbon heterocycloalkyl, 1-10 carbon alkoxy;
  • any two adjacent substituents form a ring.
  • each q is independently 0, 1, 2 or 3
  • each R is independently selected from hydrogen, deuterium, fluorine, chlorine
  • 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 Rc).
  • substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
  • substituent namely Rc
  • Rc can be, for example, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, aryl group with 6-20 carbon atoms, aryl group with 3-12 carbon atoms
  • Trialkylsilyl group alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, heterocycle with 2-10 carbon atoms
  • the "substituted" functional group may be substituted by one or more than two substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc may exist independently Or connected to each other to form a ring with the atoms; when there are two adjacent substituents Rc on a functional group, the adjacent two substituents Rc can exist independently or be condensed into a ring with the functional group to which they are connected.
  • 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 XX form a ring;” means that the two substituents may form a ring but need not form a ring, including: the situation where two adjacent substituents form a ring and two A scenario where adjacent substituents do not form a ring.
  • any two adjacent substituents may include two substituents on the same atom, and may also include two adjacent atoms each has one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated ring with the atom to which they are commonly connected; when two adjacent atoms have two substituents respectively In the case of one substituent, the two substituents may be fused to form a ring.
  • a saturated or unsaturated membered ring with 5-13 carbon atoms can be formed, such as: benzene ring, naphthalene ring, cyclopentane, cyclohexane, adamantane, fluorene ring, etc.
  • any two adjacent R 2 are connected to each other to form a ring
  • any two adjacent R 2 may or may not form a ring.
  • the number of carbon atoms in the ring is 5-14, and the ring may be saturated or unsaturated.
  • cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, phenanthrene ring, etc. but not limited thereto.
  • 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. For example: Ar 1 is Then the number of carbon atoms is 7; L is Its carbon number is 12.
  • hetero refers to a functional group including at least 1 heteroatom selected from B, N, O, S, P, Si or Se, etc. and the remaining atoms are carbon and hydrogen.
  • An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
  • alkyl may include straight or branched chain alkyl groups.
  • An alkyl group can have 1 to 10 carbon atoms, and in this application, a numerical range such as “1 to 10" refers to each integer in the given range; for example, “1 to 10 carbon atoms” means that 1 can be included alkanes of carbon atoms, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms base.
  • the alkyl group is selected from alkyl groups with 1-5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl , tert-butyl and pentyl.
  • cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic and fused ring structures.
  • Cycloalkyl groups can have 3-10 carbon atoms, and a numerical range such as "3 to 10" refers to each integer in the given range; Cycloalkyl of 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms or 10 carbon atoms. Cycloalkyl groups can be substituted or unsubstituted. Examples of cycloalkyl groups such as cyclopentyl, cyclohexane.
  • 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 specified, 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.
  • aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene, Base et al.
  • the "substituted or unsubstituted aryl group" of the present application contains 6-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group is 6-25, in some embodiments, The number of carbon atoms in the substituted or unsubstituted aryl group is 6-20, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group is 6-18, in other embodiments substituted or The number of carbon atoms in the unsubstituted aryl group is 6-12.
  • the number of carbon atoms of a substituted or unsubstituted aryl group is 6, 12, 13, 14, 15, 18, 20, 24, 25 or 30, Of course, the number of carbon atoms may 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 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 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 substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents. The total number of carbon
  • aryl groups as substituents include, but are not limited to, phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl and the like.
  • 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, furanyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type
  • N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic groups connected by carbon-carbon bond conjugation System type of heteroaryl.
  • the "substituted or unsubstituted heteroaryl" of the present application contains 3-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl is 3-25, in some embodiments , the number of carbon atoms in the substituted or unsubstituted heteroaryl group is 5-25, in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group is 5-20, in other embodiments
  • the number of carbon atoms in the substituted or unsubstituted heteroaryl groups in the examples is 5-12.
  • the number of carbon atoms in a substituted or unsubstituted heteroaryl group is 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30
  • 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 and other groups.
  • 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, pyridyl, carbazolyl, dibenzofuranyl, and dibenzothienyl.
  • 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.
  • haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
  • 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)-Any possible connection mode shown in formula (f-10).
  • the dibenzofuranyl group represented by the formula (X') is connected to other positions of the molecule through a non-positional linkage extending from the middle of one side of the benzene ring,
  • the meaning represented by it includes any possible connection manner as shown by formula (X'-1)-formula (X'-4).
  • two of U 1 , U 2 , and U 3 are N, and the other is C(R); or U 1 , U 2 , and U 3 are all N.
  • each R, R 1 , R 2 , R 3 , R 4 , R 5 is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl propyl, tert-butyl, phenyl, pyridyl, trifluoromethyl, biphenyl, or, any two adjacent R 2 form a benzene ring, a naphthalene ring or a phenanthrene ring.
  • each of R, R 1 , R 3 , R 4 , R 5 is hydrogen.
  • each R2 is selected from hydrogen , deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, trifluoromethyl, Biphenyl, or any two adjacent Rs are connected to each other to form a benzene ring, a naphthalene ring or a phenanthrene ring.
  • Equation 2-1 The groups shown are selected from the following structures:
  • the L, L 1 , L 2 , L 3 and L 4 are the same or different, and are independently selected from single bond, substituted or unsubstituted with 6-20 carbon atoms.
  • the substituents in L, L 1 , L 2 , L 3 and L 4 are the same or different, and are independently selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms. group, and an alkyl group having 1 to 5 carbon atoms.
  • substituents in L, L 1 , L 2 , L 3 and L 4 include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
  • the L, L 1 , L 2 , L 3 and L 4 are the same or different, and are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted phenylene naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted Substituted fluorenylene, substituted or unsubstituted carbazolylylene, substituted or unsubstituted anthracylene.
  • the L, L 1 , L 2 , L 3 and L 4 are the same or different, and are independently selected from a single bond or a substituted or unsubstituted group V, an unsubstituted group V is selected from the group consisting of:
  • the substituted group V has one or more substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; when the number of substituents of V is greater than 1, each substituent is the same or different.
  • L, L 1 , L 2 , L 3 and L 4 are independently selected from the group consisting of a single bond or the following groups:
  • the Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, or substituted or unsubstituted aryl groups having 4-20 carbon atoms of heteroaryl.
  • the substituents in the Ar 1 are independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 5-12 carbon atoms, carbon atoms An alkyl group having 1-5 atoms or a cycloalkyl group having 3-10 carbon atoms.
  • the substituents in the Ar 1 are each independently selected from: deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl base or carbazolyl.
  • any two adjacent substituents in Ar 1 form a saturated or unsaturated ring with 5-13 carbon atoms.
  • any two adjacent substituents form cyclopentane, cyclohexane, fluorene rings, and the like.
  • the Ar 1 is selected from a substituted or unsubstituted aryl group with 6-20 carbon atoms, or a substituted or unsubstituted heteroaryl group with 5-12 carbon atoms.
  • any two adjacent substituents in the Ar 1 form a cyclopentane, cyclohexane or fluorene ring.
  • Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenanthryl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted or unsubstituted isoquinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted pyrenyl
  • the Ar 2 is selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, or substituted or unsubstituted heteroaryl groups with 4-20 carbon atoms;
  • the substituents in the Ar 2 are each independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 5-12 carbon atoms, carbon atoms
  • the substituents in Ar 2 are each independently selected from: deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl group, carbazolyl, and optionally, any two adjacent substituents form a 5-13 membered ring.
  • any two adjacent substituents form cyclopentyl, cyclohexyl, and the like.
  • the Ar 2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuran base, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl , substituted or unsubstituted anthracenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinoline phenanthrenyl, substituted
  • the Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group W 1 , and the unsubstituted group W 1 is selected from the group consisting of the following groups:
  • substituted W 1 has one or more group substituents, each of which is independently selected from deuterium, cyano, fluorine, methyl, ethyl, n-propyl, isopropyl, tert-butyl group, phenyl group, naphthyl group, biphenyl group or carbazolyl group; when the number of substituent groups of W 1 is greater than 1, each substituent group is the same or different.
  • the Ar 1 is selected from the group consisting of the following groups:
  • the Ar is selected from the group consisting of the following groups :
  • a and B are independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-20 carbon atoms group, the structure represented by the formula 2-1 or the structure represented by the formula 2-2, and only one of A and B is selected from the structure represented by the formula 2-1 or the structure represented by the formula 2-2.
  • A is the structure shown in formula 2-1 or the structure shown in formula 2-2
  • B is selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, substituted or unsubstituted aryl groups with 5-20 carbon atoms
  • the heteroaryl group, and B is not the structure shown in formula 2-1 or formula 2-2; or B is the structure shown in formula 2-1 or the structure shown in formula 2-2, and A is selected from 6- A substituted or unsubstituted aryl group of 25, a substituted or unsubstituted heteroaryl group of 5-20 carbon atoms, and A is not a structure represented by formula 2-1 or formula 2-2.
  • the substituents in described A and B are independently selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, An alkyl group having 1 to 5 carbon atoms and a cycloalkyl group having 3 to 10 carbon atoms.
  • the substituents in A and B are each independently selected from: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, bi- Phenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl, cyclopentyl or cyclohexyl.
  • a or B when A or B is selected from a substituted or substituted aryl group with 6-25 carbon atoms and a substituted or unsubstituted heteroaryl group with 5-20 carbon atoms, Said A or B are each independently selected from the following groups: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted Substituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triphenanthryl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, Substituted or unsubstituted isoquinolinyl, substituted
  • a or B when A or B is selected from substituted or substituted aryl groups with 6-25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5-20 carbon atoms , the A and B are independently selected from the following groups:
  • A is the structure shown in formula 2-1
  • B is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted trifenthyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted
  • A is the structure shown in formula 2-2
  • B is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted trifenthyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted
  • the substituent in B is selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, is the group consisting of alkyl of 1-5 and cycloalkyl of carbon atoms of 3-10, further selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl , phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl, cyclopentyl, cyclohexyl group.
  • B is the structure shown in formula 2-1, and A is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted trifenthyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted
  • B is the structure shown in formula 2-2, and A is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted Substituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted trifenthyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted
  • the substituent in A is selected from deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms, It is a group consisting of alkyl groups of 1-5 and cycloalkyl groups of carbon atoms of 3-10.
  • cyclopentyl is further selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuran The group consisting of cyclopentyl, dibenzothienyl, cyclopentyl, and cyclohexyl.
  • the nitrogen-containing compound is selected from the group consisting of:
  • the present application also provides an electronic component for realizing photoelectric conversion or electro-optical conversion.
  • the electronic component includes an anode and a cathode disposed oppositely, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the nitrogen-containing compound of the present application.
  • the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer.
  • the functional layer 300 includes a hole injection layer 310, a hole transport layer, an organic electroluminescence layer 330, a hole blocking layer 340, an electron transport layer 350 and an electron injection layer 360;
  • the hole transport layer includes a first hole transport layer 321 and the second hole transport layer 322, wherein the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322;
  • the hole blocking layer 340 , the electron transport layer 350 and the electron injection layer 360 may be formed on the anode 100 in sequence, and the organic electroluminescence layer 330 may contain the nitrogen-containing compound described in the first aspect of the present application, preferably the compound 1-700. at least one.
  • 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 hole transport layer 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, to which the present application No special restrictions are made.
  • the hole transport layer includes a first hole transport layer 321 and a second hole transport layer 322, the first hole transport layer 321 is composed of compound NPB, and the second hole transport layer is composed of NPB.
  • the hole transport layer 322 is composed of the compound TCBPA.
  • the organic electroluminescent layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
  • the organic electroluminescent layer 330 is composed of a host material and a guest material. The holes and 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, and the host The material transfers energy to the guest material, which in turn enables the guest material to emit light.
  • the host material of the organic electroluminescent layer 330 is composed of the nitrogen-containing compound provided in the present application and GH-P1.
  • the nitrogen-containing compound provided by the present application has the characteristics of polycyclic conjugation, the parent structure of the fused indolocarbazole, the bond energy between atoms is high, the thermal stability is good, and the solid-state stacking between molecules is favorable. In organic electroluminescent devices, it exhibits a long lifetime as a light-emitting layer material.
  • the nitrogen-containing compound provided in the present application has a high T1 value, and is suitable for use as a host material for a light-emitting layer in an OLED device, especially a green light host material.
  • the compound of the present application is used in the light-emitting layer material of an organic electroluminescent device, 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.
  • the guest material of the organic electroluminescent layer 330 can 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 described in this application. special restrictions.
  • the guest material of the organic light-emitting layer 330 may be Ir(ppy) 2 acac.
  • the electron transport layer 350 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 benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials, which are not specifically limited in this application.
  • the electron transport layer 350 may be composed of HNBphen and LiQ.
  • the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
  • cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/ Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca, but not limited thereto.
  • a metal electrode comprising silver and magnesium is preferably included as the cathode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 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 HAT-CN.
  • an electron injection layer 360 may also be disposed between the cathode 200 and the electron transport layer 350 to enhance the capability of injecting electrons into the electron transport layer 350 .
  • the electron injection layer 360 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.
  • the electron injection layer 360 may include ytterbium (Yb).
  • the present application also provides an electronic device, which includes the electronic components described in the present application.
  • the electronic device provided by the present application is a first electronic device 400
  • the first electronic device 400 includes any organic electroluminescent device described in the above organic electroluminescent device embodiment.
  • the electronic device may be a display device, a lighting device, an optical communication device or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, it has the same beneficial effects, and details are not described herein again.
  • B-1 (50.0g, 182.40mmol), m-chlorobenzeneboronic acid (31.37g, 200.64mmol) (A-1), potassium carbonate (55.5 g, 401.3 mmol), tetrakis(triphenylphosphine)palladium (4.2 g, 3.6 mmol), tetrabutylammonium bromide (1.2 g, 3.6 mmol), and toluene ( 400 mL), a mixed solvent of ethanol (200 mL) and water (100 mL).
  • intermediate sub A-2 shown in the following table 1 to intermediate subA-10 are synthesized with reference to the (2) step and (3) reaction of intermediate sub A-1, reactant A-X (X is 1- 7) Instead of reactant A-1, reactant B-X (X is 1-6) replaces reactant B-1.
  • the intermediate sub A-11-sub A-18 shown in Table 1 refers to the reaction of step (3) of sub A-1, and replaces reactant B-1 with reactant B-X (X is 7-14).
  • intermediate sub1-I-A11 With reference to the synthesis method of intermediate sub1-I-A11, the intermediate shown in the following table 3 is synthesized, wherein reactant B-X replaces reactant B-1 (X is 15, 16 or 17), wherein reactant A-X (X is 9 , 10, 11, 12, 13 or 14) instead of reactant A-8, the intermediate sub1-I-AX (X is 12, 13, 14, 15, 16 or 17) as shown in Table 3 below was synthesized.
  • Extract with toluene and water combine the organic phases, dry with anhydrous magnesium sulfate, filter and concentrate, and use dichloromethane/n-heptane system to purify the crude product by silica gel column chromatography to obtain a solid intermediate sub B-1 (38.1 g , the yield is 56%).
  • Extract with toluene and water combine the organic phases, dry with anhydrous magnesium sulfate, filter and concentrate, and use dichloromethane/n-heptane system to purify the crude product by silica gel column chromatography to obtain a solid intermediate sub B-7 (17.3 g , the yield is 55%).
  • intermediate sub B-7 With reference to the synthesis method of intermediate sub B-7, the intermediate shown in the following table 8 is synthesized, wherein reactant C-X (X is 19 or 20) replaces reactant C-19, reactant B-X (X is 7 or 11) replaces Reactant B-7, the intermediate sub B-X (X is 8 or 9) shown in Table 8 below is synthesized.
  • Extract with toluene and water combine the organic phases, dry with anhydrous magnesium sulfate, filter and concentrate, and use dichloromethane/n-heptane system to purify the crude product by silica gel column chromatography to obtain a solid intermediate sub A-I-29 (32.5 g , the yield is 55%).
  • the intermediate shown in the following table 10 is synthesized, wherein the reactant A-X (4, 12, 13 or 15) replaces the reactant A-5, and the intermediate shown in the following table 10 is synthesized sub A-I-X (X is 30-33).
  • the intermediate sub A-X (X is 30-33) shown in Table 10 below was synthesized.
  • the anode 100ITO substrate with a thickness of 110 nm was cut into a size of 40 mm (length) ⁇ 40 mm (width) ⁇ 0.7 mm (thickness), and a photolithography process was used to prepare an experimental substrate with a cathode 200, an anode 100 and an insulating layer pattern. , using ultraviolet ozone and O 2 : N 2 plasma for surface treatment to increase the work function of the anode 100 (experimental substrate), and using an organic solvent to clean the surface of the ITO substrate to remove scum and oil on the surface of the ITO substrate.
  • the compound HAT-CN (see below for the structural formula) was vacuum-evaporated on the experimental substrate to form a hole injection layer 310 (HIL) with a thickness of 10 nm; and the compound NPB was vacuum-evaporated on the hole injection layer 310 to form a thickness of 115 nm.
  • the first hole transport layer 321 (HTL1).
  • a layer of TCBPA was vacuum evaporated on the first hole transport layer 321 (HTL1) to form a second hole transport layer 322 (HTL2) with a thickness of 35 nm.
  • HNBphen and LiQ were mixed at a weight ratio of 1:1 and evaporated to form an electron transport layer 350 (ETL) with a thickness of 30 nm, and then Yb was evaporated on the electron transport layer to form an electron injection layer 360 (EIL) with a thickness of 1 nm. ).
  • ETL electron transport layer 350
  • EIL electron injection layer 360
  • Magnesium (Mg) and silver (Ag) were vacuum-deposited on the electron injection layer at a film thickness ratio of 1:9 to form a cathode 200 having a thickness of 13 nm.
  • a layer of CP-1 with a thickness of 65 nm is vapor-deposited on the cathode 200 as a protective layer to form a capping layer (CPL), thereby completing the manufacture of the organic light-emitting device.
  • CPL capping layer
  • a green organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound shown in Table 14 was used instead of Compound 67 in forming the light-emitting layer (EML).
  • the IVL performance of the device was tested under the condition of 10 mA/cm 2
  • the lifetime of the T95 device was tested under the condition of 20 mA/cm 2 .
  • the results are shown in Table 14.
  • the performance of the organic electroluminescent devices prepared in Examples 1-56 is improved.
  • Examples 1-56 as the compound of the light-emitting layer are compared with the comparative examples 1-4 of the devices corresponding to the compounds in the prior art.
  • the luminous efficiency (Cd/A) is increased by at least 22.4%
  • the external quantum efficiency EQE (%) is increased by at least 22.9%
  • the lifetime is increased to 27.8%.

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  • Plural Heterocyclic Compounds (AREA)

Abstract

本申请提供一种含氮化合物及其电子元件和电子装置，属于有机电致发光技术领域。本申请提供的含氮化合物具有多环共轭特性，该化合物具有稠合的吲哚并咔唑母体结构，原子间的键能高，因而具有良好的热稳定性，并有利于分子间的固态堆积，在有机电致发光器件中作为发光层材料表现为长寿命。本申请提供的含氮化合物通过稠合芳香环的母核结构分别连接含氮基团(三嗪、吡啶和嘧啶)以及苯并噁唑或苯并噻唑基团，由此组合而成的结构具有高的偶极矩，从而使材料极性提高。将本申请含氮化合物用作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，改善器件发光效率以及使用寿命。

Description

一种含氮化合物及包含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2021年1月28日递交的申请号为CN202110122427.9的中国专利申请以及2021年4月8日递交的申请号为CN202110380418.X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
本申请涉及有机电致发光技术领域，具体而言，涉及一种含氮化合物及包含其的电子元件和电子装置。
背景技术
有机电致发光材料(OLED)作为新一代显示技术，具有超薄、自发光、视角宽、响应快、发光效率高、温度适应性好、生产工艺简单、驱动电压低、能耗低等优点，已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
有机发光现象是指使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件通常具有这样的结构，其包括阳极、阴极和其间的有机材料层。有机材料层通常以由不同材料构成的多层结构形成以提高有机电致发光器件的亮度、效率和寿命，有机材料层可由空穴注入层、空穴传输层、发光层、电子传输层和电子注入层等构成。有机发光器件结构中，当在两个电极之间施加电压时，空穴和电子分别从阳极和阴极注入有机材料层，当注入的空穴与电子相遇时形成激子，并且当这些激子返回基态时发光。现有的有机电致发光器件中，最主要的问题为寿命和效率，随着显示器的大面积化，驱动电压也随之提高，发光效率及电力效率也需要提高，并且要保证一定的使用寿命，因此，有机材料必须要解决这些效率或寿命问题，需要不断地开发高效率，长寿命，适于量产的用于有机发光器件的新材料。
需要说明的是，在上述背景技术部分公开的信息仅用于加强对本申请的背景的理解，因此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
本申请的目的在于克服上述现有技术中的不足，提供一种含氮化合物及包含其的电子元件和电子装置，可提高发光效率，延长器件寿命。
为实现上述发明目的，本申请采用如下技术方案：
根据本申请的第一个方面，提供了一种含氮化合物，所述含氮化合物的结构通式如式1所示：
Figure PCTCN2021112354-appb-000001
Figure PCTCN2021112354-appb-000002
其中，
Figure PCTCN2021112354-appb-000003
表示化学键，A、B相同或不同，分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基、式2-1所示结构或式2-2所示结构，且A和B中至少有一个选自式2-1或式2-2；
U 1、U 2和U 3相同或不同，分别独立地选自N或C(R)，且U 1、U 2和U 3中的至少一个为N；
各R、R 1、R 2、R 3、R 4、R 5分别独立地选自氢、氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为1-5的卤代烷基、碳原子数为3-10的环烷基；
n 1表示取代基R 1的个数，n 1选自1、2或3，当n 1大于1时，任意两个R 1相同或不同；
n 2表示取代基R 2的个数，n 2选自1、2、3或4，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；
n 3表示取代基R 3的个数，n 3选自1、2、3或4，当n 3大于1时，任意两个R 3相同或不同；
n 4表示取代基R 4的个数，n 4选自1或2，当n 4大于1时，任意两个R 4相同或不同；
n 5表示取代基R 5的个数，n 5选自1、2、3或4，当n 5大于1时，任意两个R 5相同或不同；
X选自S或O；
L、L 1、L 2、L 3和L 4相同或不同，且分别独立地选自单键、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；
Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述A、B、L、L 1、L 2、L 3、L 4、Ar 1和Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为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；
任选地，在Ar 1和Ar 2中，任意两个相邻的取代基形成环。
本申请提供的含氮化合物具有多环共轭特性，该化合物具有稠合的吲哚并咔唑的母体结构，原子间的键能高，因而具有良好的热稳定性，并有利于分子间的固态堆积，在有机电致发光器件中作为发光层材料表现为长寿命。本申请的含氮化合物通过吲哚并咔唑结构分别连接含氮基团(三嗪、吡啶和嘧啶)以及苯并噁唑或苯并噻唑基团，由此所组成的结构具有高的偶极矩，从而使材料极性提高。
本申请提供的含氮化合物具有较高的T 1值，适于用作OLED器件中的发光层主体材料，尤其是绿光主体材料。将本申请化合物用作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传输的平衡程度，改善器件发光效率以及使用寿命。
根据本申请的第二个方面，提供一种电子元件，包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，功能层包含上述的含氮化合物。
根据本申请的第三个方面，提供一种电子装置，包括上述的电子元件。
应当理解的是，以上的一般描述和后文的细节描述仅是示例性和解释性的，并不能限制本申请。
附图说明
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。
在附图中：
图1是本申请的有机电致发光器件的一种实施方式的结构示意图。
图2是本申请的电子装置的一种实施方式的结构示意图。
附图标记说明
100、阳极；200、阴极；300、功能层；310、空穴注入层；321、第一空穴传输层；322、第二空穴传输层；330、有机电致发光层；340、空穴阻挡层；350、电子传输层；360、电子注入层；400、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。
本申请提供了一种含氮化合物，该含氮化合物的结构通式如式1所示：
Figure PCTCN2021112354-appb-000004
其中，
Figure PCTCN2021112354-appb-000005
表示化学键，A、B相同或不同，分别独立地选自碳原子数为6-30的取代或未取代的芳基、取代或未取代的碳原子数为3-30的杂芳基、式2-1所示结构或式2-2所示结构，且A和B中至少有一个选自式2-1或式2-2所示结构；
U 1、U 2和U 3相同或不同，分别独立地选自N或C(R)，且U 1、U 2和U 3中的至少一个为N；
各R、R 1、R 2、R 3、R 4、R 5分别独立地选自氢、氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为1-5的卤代烷基、碳原子数为3-10的环烷基；
n 1表示取代基R 1的个数，n 1选自1、2或3，当n 1大于1时，任意两个R 1相同或不同；
n 2表示取代基R 2的个数，n 2选自1、2、3或4，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；
n 3表示取代基R 3的个数，n 3选自1、2、3或4，当n 3大于1时，任意两个R 3相同或不同；
n 4表示取代基R 4的个数，n 4选自1或2，当n 4大于1时，任意两个R 4相同或不同；
n 5表示取代基R 5的个数，n 5选自1、2、3或4，当n 5大于1时，任意两个R 5相同或不同；X选自S或O；
L、L 1、L 2、L 3和L 4相同或不同，且分别独立地选自单键、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；
Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
所述A、B、L、L 1、L 2、L 3、L 4、Ar 1和Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为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；
任选地，在Ar 1和Ar 2中，任意两个相邻的取代基形成环。
在本申请中，所采用的描述方式“各自独立地选自”与“分别独立地选自”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 PCTCN2021112354-appb-000006
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，“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Rc)。例如，“取代或未取代的芳基”是指具有取代基Rc的芳基或者非取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为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。在本申请中，“取代的”官能团可以被上述Rc中的一个或2个以上的取代基取代；当同一个原子上连接有两个取代基Rc时，这两个取代基Rc可以独立地存在或者相互连接以与所述原子形成环；当官能团上存在两个相邻的取代基Rc时，相邻的两个取代基Rc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，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以发生但不必发生，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，“任意两个相邻的取代基形成环”中，“任意两个相邻的取代基”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的该原子形成饱和或不饱和的环；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环。举例而言，当Ar 2有2个或2个以上的取代基，且任意相邻的取代基形成环时，可以形成饱和或不饱和的碳原子数为5-13的元 环，例如：苯环、萘环、环戊烷、环己烷、金刚烷、芴环等等。
在本申请中，“任选地，任意两个相邻的R 2相互连接形成环”是指任意两个相邻的R 2可以形成环，也可以不形成环。举例而言，当相邻的两个R 2成环时，该环的碳原子数为5-14，且该环可以是饱和的，也可以是不饱和的。例如：环己烷、环戊烷、金刚烷、苯环、萘环、菲环等，但不限于此。
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。例如：Ar 1为
Figure PCTCN2021112354-appb-000007
则其碳原子数为7；L为
Figure PCTCN2021112354-appb-000008
其碳原子数为12。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个选自B、N、O、S、P、Si或Se等的杂原子且其余原子为碳和氢。未取代的烷基可以是没有任何双键或三键的“饱和烷基基团”。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至10个碳原子，在本申请中，诸如“1至10”的数值范围是指给定范围中的各个整数；例如，"1至10个碳原子”是指可包含1个碳原子、2个碳原子、3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子、10个碳原子的烷基。可选地，烷基选自碳原子数为1-5的烷基，具体实施例包括但不限于，甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基和戊基。
在本申请中，环烷基指的是含有脂环结构的饱和烃，包含单环和稠环结构。环烷基可具有3-10个碳原子，诸如“3至10”的数值范围是指给定范围中的各个整数；例如，“3至10个碳原子”是指可包含3个碳原子、4个碳原子、5个碳原子、6个碳原子、7个碳原子、8个碳原子、9个碳原子或10个碳原子的环烷基。环烷基可为取代的或未取代的。环烷基的实例，如环戊烷基、环己烷基。
在本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(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。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021112354-appb-000009
基等。本申请的“取代或未取代的芳基”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是6-25个，在一些实施例中，取代或未取代的芳基中的碳原子数是6-20个，在另一些实施例中取代或未取代的芳基中的碳原子数是6-18个，在另一些实施例中取代或未取代的芳基中的碳原子数是6-12个。举例而言，本申请中，取代或未取代的芳基的碳原子数量是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，指的是芳基及其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、萘基、蒽基、菲基、二甲基芴基、联苯基等等。
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-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-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。本申请的“取代或未取代的杂芳基”含有3-30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是3-25个，在一些实施例中，取代或未取代的杂芳基中的碳原子数是5-25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是5-20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是5-12个。举例而言，其取代或未取代的杂芳基中的碳原子数量是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、烷氧基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。
在本申请中，作为取代基的杂芳基，具体实例包括但不限于：吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基。
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1-10的卤代烷基的具体实例包括但不限于，三氟甲基。
本申请中，不定位连接键是指从环体系中伸出的单键
Figure PCTCN2021112354-appb-000010
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 PCTCN2021112354-appb-000011
Figure PCTCN2021112354-appb-000012
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃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 PCTCN2021112354-appb-000013
下文中对于不定位连接或不定位取代的含义与此处相同，后续将不再进行赘述。
在本申请一种实施方式中，U 1、U 2、U 3中，有2个为N，另一个为C(R)；或者U 1、U 2、U 3均为N。
在本申请的一些实施方式中，各R、R 1、R 2、R 3、R 4、R 5独立地选自氢、氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、吡啶基、三氟甲基、联苯基，或者，任意两个相邻的R 2形成苯环、萘环或菲环。
可选地，各R、R 1、R 3、R 4、R 5均为氢。
可选地，各R 2选自氢、氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、吡啶基、三氟甲基、联苯基，或者任意两个相邻的R相互连接形成苯环、萘环或菲环。
在本申请中，式2-1
Figure PCTCN2021112354-appb-000014
所示基团选自以下结构：
Figure PCTCN2021112354-appb-000015
在本申请的一些实施方式中，所述L、L 1、L 2、L 3和L 4相同或不同，且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、或者碳原子数为5-20的取代或未取代的亚杂芳基。
可选地，所述L、L 1、L 2、L 3和L 4中的取代基相同或不同，分别独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为1-5的烷基。
具体地，所述L、L 1、L 2、L 3和L 4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。
在本申请的一些实施方式中，所述L、L 1、L 2、L 3和L 4相同或不同，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、取代或未取代的亚吡啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚芴基、取代或未取代的亚咔唑基、取代或未取代的亚蒽基。
在本申请的一些实施方式中，所述L、L 1、L 2、L 3和L 4相同或不同，分别独立地选自单键或者取代或未取代的基团V，未取代的基团V选自如下基团所组成的组：
Figure PCTCN2021112354-appb-000016
其中，
Figure PCTCN2021112354-appb-000017
表示化学键；取代的基团V上具有一个或多个取代基，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基或苯基；当V的取代基个数大于1时，各取代基相同或不同。
可选地，L、L 1、L 2、L 3和L 4分别独立地选自单键或者如下基团所组成的组：
Figure PCTCN2021112354-appb-000018
Figure PCTCN2021112354-appb-000019
在本申请的一些实施方式中，所述Ar 1、Ar 2各自独立地选自碳原子数为6-25的取代或未取代的芳基、或者碳原子数为4-20的取代或未取代的杂芳基。
可选地，所述Ar 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6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基或碳原子3-10的环烷基。
具体地，所述Ar 1中的取代基各自独立地选自：氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基或咔唑基。
任选地，所述Ar 1中任意两个相邻的取代基形成碳原子数为5-13的饱和或不饱和环。举例而言，任意两个相邻的取代基形成环戊烷、环己烷、芴环等。
进一步可选地，所述Ar 1选自碳原子数为6-20的取代或未取代的芳基、或者碳原子数为5-12的取代或未取代的杂芳基。
任选地，所述Ar 1中任意两个相邻的取代基形成环戊烷、环己烷或芴环。
在本申请的一些实施方式中，Ar 1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芘基、取代或未取代的菲咯啉基。
在本申请的一些实施方式中，所述Ar 2选自碳原子数为6-25的取代或未取代的芳基、或者碳原子数为4-20的取代或未取代的杂芳基；
可选地，所述Ar 2中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为1-5的卤代烷基或碳原子数为3-10的环烷基，任选地，所述Ar 2中任意两个相邻的取代基形成碳原子数为5-13的饱和或不饱和环。
具体地，所述Ar 2中的取代基各自独立地选自：氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、咔唑基，任选地，任意两个相邻的取代基形成5-13元环。举例而言，任意两个相邻的取代基形成环戊烷基、环己烷基等。
在本申请的另一些实施方式中，所述Ar 2选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基，取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的N-苯基咔唑基、取代或未取代的咔唑基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的芘基、取代或未取代的喹啉基、取代或未取代异喹啉基、取代或未取代的菲咯啉基、取代或未取代的苯并菲基、取代或未取代的呋喃基、取代或未取代的噻吩基或以下取代或未取代的基团：
Figure PCTCN2021112354-appb-000020
(苯并呋喃[2,3-b]吡啶)。
在本申请的一些实施方式中，所述Ar 1、Ar 2各自独立地选自取代或未取代的基团W 1，未取代的基团W 1选自如下基团组成的组：
Figure PCTCN2021112354-appb-000021
其中，
Figure PCTCN2021112354-appb-000022
表示化学键；取代的W 1上具有一个或多个基团取代基，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基或咔唑基；当W 1的取代基个数大于1时，各取代基相同或不同。
可选地，所述Ar 1选自以下基团组成的组：
Figure PCTCN2021112354-appb-000023
Figure PCTCN2021112354-appb-000024
可选地，所述Ar 2选自以下基团组成的组：
Figure PCTCN2021112354-appb-000025
在本申请的一些实施方式中，所述A、B分别独立地选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基、式2-1所示结构或式2-2所示结构，且A 和B中有且仅有一个选自式2-1所示结构或式2-2所示结构。即A为式2-1所示结构或式2-2所示结构，B选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基，且B不为式2-1或式2-2所示结构；或者B为式2-1所示结构或式2-2所示结构，A选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基，且A不为式2-1或式2-2所示结构。
可选地，所述A、B中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为3-10的环烷基。
具体地，所述A、B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、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、环戊烷基或环己烷基。
在本申请的一些实施方式中，当所述A或B选自碳原子数为6-25的取代或取代的芳基、碳原子数为5-20的取代或未取代的杂芳基时，所述A或B分别独立地选自以下基团：取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基。
在本申请的另一些实施方式中，当所述A或B选自碳原子数为6-25的取代或取代的芳基、碳原子数为5-20的取代或未取代的杂芳基时，所述A、B分别独立地选自以下基团：
Figure PCTCN2021112354-appb-000026
Figure PCTCN2021112354-appb-000027
在本申请的一些实施方式中，A为式2-1所示结构，B选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基所组成的组。
在本申请的一些实施方式中，A为式2-2所示结构，B选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基所组成的组。
在本申请一些实施方式中，B中的取代基选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子3-10的环烷基所组成的组，进一步地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、环戊烷基、环己烷基所组成的组。
在本申请的一些实施方式中，B为式2-1所示结构，A选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基所组成的组。
在本申请的一些实施方式中，B为式2-2所示结构，A选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基所组成的组。
在本申请一些实施方式中，A中的取代基选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子3-10的环烷基所组成的组。进一步地选自氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、环戊烷基、环己烷基所组成的组。
在本申请的一些实施方式中，当A选自式2-1所示结构或2-2所示结构时，X为O。
可选地，含氮化合物选自如下化合物组成的组：
Figure PCTCN2021112354-appb-000028
Figure PCTCN2021112354-appb-000029
Figure PCTCN2021112354-appb-000030
Figure PCTCN2021112354-appb-000031
Figure PCTCN2021112354-appb-000032
Figure PCTCN2021112354-appb-000033
Figure PCTCN2021112354-appb-000034
Figure PCTCN2021112354-appb-000035
Figure PCTCN2021112354-appb-000036
Figure PCTCN2021112354-appb-000037
Figure PCTCN2021112354-appb-000038
Figure PCTCN2021112354-appb-000039
Figure PCTCN2021112354-appb-000040
Figure PCTCN2021112354-appb-000041
Figure PCTCN2021112354-appb-000042
Figure PCTCN2021112354-appb-000043
Figure PCTCN2021112354-appb-000044
Figure PCTCN2021112354-appb-000045
Figure PCTCN2021112354-appb-000046
Figure PCTCN2021112354-appb-000047
Figure PCTCN2021112354-appb-000048
Figure PCTCN2021112354-appb-000049
Figure PCTCN2021112354-appb-000050
Figure PCTCN2021112354-appb-000051
Figure PCTCN2021112354-appb-000052
Figure PCTCN2021112354-appb-000053
本申请还提供一种电子元件，用于实现光电转换或者电光转化。该电子元件包括相对设置的阳极和阴极，以及介于阳极与阴极之间的至少一层功能层，该功能层包含本申请的含氮化合物。
在本申请一种具体实施方式中，如图1所示，本申请的有机电致发光器件包括阳极100、阴极200、以及介于阳极层与阴极层之间的至少一层功能层300，该功能层300包括空穴注入层310、空穴传输层、有机电致发光层330、空穴阻挡层340、电子传输层350以及电子注入层360；空穴传输层包括第一空穴传输层321和第二空穴传输层322，其中第一空穴传输层321相对于第二空穴传输层322更靠近阳极100；空穴注入层310、空穴传输层、有机电致发光层330、空穴阻挡层340、电子传输层350以及电子注入层360可以依次形成在阳极100上，有机电致发光层330可以含有本申请第一方面所述的含氮化合物，优选含有化合物1-700中的至少一种。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括:金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层可以包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，空穴传输层包括第一空穴传输层321和第二空穴传输层322，第一空穴传输层321由化合物NPB组成，第二空穴传输层322由化合物TCBPA组成。
可选地，有机电致发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机电致发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和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。
有机电致发光层330的主体材料由本申请所提供的含氮化合物和GH-P1组成。本申请提供的含氮化合物具有多环共轭特性，稠合的吲哚并咔唑的母体结构，原子间的键能高，具有良好的热稳定性，并有利于分子间的固态堆积，在有机电致发光器件中作为发光层材料表现为长寿命。通过吲哚并咔唑结构分别连接苯并噁唑或苯并噻唑基团和含氮基团(三嗪、吡啶和嘧啶) 所组成结构；此种组合使得该部分结构具有高的偶极矩，从而使材料极性提高。本申请提供的含氮化合物具有较高的T1值，适于用作OLED器件中的发光层主体材料，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。
有机电致发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机发光层330的客体材料可以为Ir(ppy) 2acac。
电子传输层350可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，电子传输层350可以由HNBphen和LiQ组成。
可选地，阴极200包括以下阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括:金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al，Liq/Al，LiO 2/Al，LiF/Ca，LiF/Al和BaF 2/Ca，但不限于此。优选包括包含银和镁的金属电极作为阴极。
可选地，在阳极100和空穴传输层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。在本申请的一种实施方式中，空穴注入层310可以由HAT-CN组成。
可选地，在阴极200和电子传输层350之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。在本申请的一种实施方式中，电子注入层360可以包括镱(Yb)。
本申请还提供一种电子装置，该电子装置包括本申请所述的电子元件。
举例而言，如图2所示，本申请提供的电子装置为第一电子装置400，该第一电子装置400包括上述有机电致发光器件实施方式所描述的任意一种有机电致发光器件。该电子装置可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于第一电子装置400具有上述有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
下面将结合实施例详细描述本申请，但是，以下描述是用于解释本申请，而不是以任意方式限制本申请的范围。
合成实施例
所属领域的专业人员应该认识到，本申请所描述的化学反应可以用来合适地制备许多本申请的其他化合物，且用于制备本申请的化合物的其它方法都被认为是在本申请的范围之内。例如，根据本申请那些非例证的化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成，如适当的保护干扰基团，通过利用其他已知的试剂替代本申请所描述的试剂，或将反应条件做一些常规的修改。另外，本申请所公开的反化合物合成。
合成例1：化合物67的合成
(1)反应物B-1的合成
Figure PCTCN2021112354-appb-000054
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入2-溴-6-硝基苯酚(50.0g,229.3mmol)，苯甲醇(29.76g,275.2mmol)，1,1'-双(二苯基膦)二茂铁(3.71g,6.8mmol)和二甲苯(500mL)开启搅拌和加热，待温度上升到125-135℃，回流反应36h，待反应完成后停止搅拌和加热，待温度降到室温时开始处理反应；加入甲苯和水萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体化合物反应物B-1(40.23g，64％)。
(2)中间体sub 1-I-A1的合成
Figure PCTCN2021112354-appb-000055
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入B-1(50.0g,182.40mmol)、间氯苯硼酸(31.37g,200.64mmol)(A-1)、碳酸钾(55.5g，401.3mmol)、四(三苯基膦)钯(4.2g,3.6mmol)、四丁基溴化铵(1.2g，3.6mmol)，并加入甲苯(400mL)、乙醇(200mL)和水(100mL)的混合溶剂。开启搅拌并加热，待温度上升到75-80℃，回流反应8h，反应结束后，冷却至室温。用甲苯和水萃取分离有机相，水洗至中性，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体化合物中间体sub1-I-A1(39.6g,71％)。
(3)中间体sub A-1的合成
Figure PCTCN2021112354-appb-000056
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入中间体sub 1-I-A1(35.0g,114.5mmol)、吲哚并[2,3-A]咔唑(35.3g,137.6mmol)、Pd 2(dba) 3(2.1g，2.3mmol)、三叔丁基膦(0.92g,4.6mmol)、叔丁醇钠(27.5g,286.2mmol)、二甲苯(500mL)。开启搅拌并加热，待温度上升到135-145℃，回流反应10h，反应结束后，冷却至室温。反应液水洗后分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，使用二氯甲烷/乙醇体系对粗品进行重结晶，得到白色固体中间体sub A-1(45.1g,75％)。
参照中间体sub A-1的合成方法，合成下表1所示的中间体，合成如下表1所示的中间体sub A-X(X为2-18)。其中，下表1所示的中间体sub A-2至中间体subA-10参照中间体sub A-1的第(2)步和第(3)反应合成，将反应物A-X(X为1-7)代替反应物A-1，反应物B-X(X为1-6)代替反应物B-1。而表1所示的中间体sub A-11-sub A-18参照sub A-1的第(3)步反应，将化反应物B-X(X为7-14)代替反应物B-1。
表1
Figure PCTCN2021112354-appb-000057
Figure PCTCN2021112354-appb-000058
Figure PCTCN2021112354-appb-000059
Figure PCTCN2021112354-appb-000060
(4)化合物67的合成
Figure PCTCN2021112354-appb-000061
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入中间体sub A-1(20.0g,38.0mmol)、2-氯-4,6-二苯基-1,3,5-三嗪(35.3g,137.6mmol)(反应物C-1)、DMF(200mL)，降温至0℃，加入NaH(1.0g,41.8mmol)后体系由白色变成黄色，自然升至室温有固体析出，反应结束。反应液水洗后过滤得到固体产物，用少量乙醇进行淋洗，粗品利用甲苯进行重结晶，得到化合物67(13.2g,46％)。质谱：m/z＝757.26[M+H] +。
参照化合物67的合成方法，合成下表2所示的化合物，其中，中间体sub A-X(X为1-18)代替中间体sub A-1，其中反应物C-X(X为1-11)代替反应物C-1，合成如下表2所示的化合物。
表2
Figure PCTCN2021112354-appb-000062
Figure PCTCN2021112354-appb-000063
Figure PCTCN2021112354-appb-000064
Figure PCTCN2021112354-appb-000065
Figure PCTCN2021112354-appb-000066
合成例28：化合物257的合成
(1)中间体Sub 1-II-A11的合成
Figure PCTCN2021112354-appb-000067
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入2,5-二氯苯并噁唑(35.0g,186.1mmol)(反应物B-15)、2-萘硼酸(32.0,186.1mmol)(反应物A-8)、碳酸钾(64.3g,465.4mmol)、四(三苯基膦)钯(4.3g,3.7mmol)、四丁基溴化铵(1.2g,3.72mmol)，并加入甲苯(280mL)、乙醇(70mL)和水(70mL)的混合溶剂。开启搅拌并加热，待温度上升到75-80℃，回流反应15h，反应结束后，冷却至室温。用甲苯和水萃取分离有机相，水洗至中性，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩；使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体化合物中间体sub1-I-A11(31.7g,61％)。
参照中间体sub1-I-A11的合成方法，合成下表3所示的中间体，其中反应物B-X代替反应物B-1(X为15、16或17)，其中反应物A-X(X为9、10、11、12、13或14)代替反应物A-8，合成如下表3所示的中间体sub1-I-AX(X为12、13、14、15、16或17)。
表3
Figure PCTCN2021112354-appb-000068
Figure PCTCN2021112354-appb-000069
(2)化合物257的合成
参照化合物67的合成方法，合成下表4所示的化合物，其中，中间体sub1-I-AX(X为11、12、13、14或17)代替中间体sub1-I-A1，其中反应物C-X(X为1、2、4或14-18)代替反应物C-1，合成如下表4所示的化合物。
表4
Figure PCTCN2021112354-appb-000070
Figure PCTCN2021112354-appb-000071
制备例38：化合物121的合成
(1)中间体Sub A-19的合成
Figure PCTCN2021112354-appb-000072
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入哚并[2,3-A]咔唑(50.0g,195.1mmol)、溴苯(27.5g,175.5mmol)(反应物D-1)、Pd 2(dba) 3(3.5g，3.9mmol)、三叔丁基膦(1.6g,7.8mmol)、叔丁醇钠(41.2g,429.2mmol)、二甲苯(500mL)。开启搅拌并加热，待温度上升到135-145℃，回流反应10h，反应结束后，冷却至室温。加入甲苯和水萃取反应溶液，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩，使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体中间体sub A-19(47.3g,73％)。
参照中间体sub A-19的合成方法，合成下表5所示的中间体，其中反应物D-X代替反应物D-1(X为2-10)，合成如下表5所示的中间体sub A-X(X为20-28)。
表5
Figure PCTCN2021112354-appb-000073
Figure PCTCN2021112354-appb-000074
(2)中间体sub B-1的合成
Figure PCTCN2021112354-appb-000075
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入反应物B-1(55.0g,200.6mmol)，联硼酸频哪醇酯(76.4g,300.9mmol)，1，4二氧六环(600mL)，乙酸钾(49.2g，501.6mmol),x-phos(1.9g，4.0mmol)，Pd 2(dba) 3(1.8g，2.0mmol)，加热至95-105℃回流反应14h，反应结束后，冷却至室温。加入甲苯和水萃取反应溶液，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩，生成物用乙醇打浆，过滤得到中间体sub 1-I-B1(54.1g，84％)。
Figure PCTCN2021112354-appb-000076
向装有机械搅拌、温C度19计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入中间体sub 1-I-B1(45.5g，141.5mmol),2,4-二氯-6-苯基-1,3,5-三嗪(40.0g，176.9mmol)(反应物C-19)，四(三苯基膦)钯(2.0g，1.7mmol)，碳酸钾(61.1g，442.3mmol)，四丁基溴化铵(1.1g，3.5mmol)，四氢呋喃(320ml)和去离子水(80ml)；开启搅拌和加热，待温度上升到60-70℃，回流反应10h，反应结束后，冷却至室温。用甲苯和水进行萃取，合并有机相，用无水硫酸镁进行干燥，过滤浓缩，使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体中间体sub B-1(38.1g，收率56％)。
参照中间体sub B-1的合成方法，合成下表6所示的中间体，其中反应物C-X代替反应物C-19(X为20-24)，合成如下表6所示的中间体sub B-X(X为2、3、4、5或6)。
表6
Figure PCTCN2021112354-appb-000077
Figure PCTCN2021112354-appb-000078
(3)化合物121的合成
Figure PCTCN2021112354-appb-000079
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入中间体sub A-19(20.0g,60.2mmol)、中间体sub B-1(27.7g,72.2mmol)、DMF(200mL)，降温至0℃，加入NaH(1.6g,66.2mmol)后体系由白色变成黄色，自然升至室温有固体析出，反应结束。反应液水洗后过滤得到固体产物，用少量乙醇进行淋洗，粗品利用甲苯进行重结晶，得到化合物121(23.3g,57％)。质谱：m/z＝681.23[M+H] +。
参照化合物121的合成方法，合成下表7所示的化合物，其中，中间体sub A-X(X为19-28)代替中间体sub A-19，中间体sub B-X(X为2-6)代替中间体sub B-1，合成如下表7所示的化合物。
表7
Figure PCTCN2021112354-appb-000080
Figure PCTCN2021112354-appb-000081
合成例48：化合物667的合成
(1)中间体sub B-7的合成
Figure PCTCN2021112354-appb-000082
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入反应物B-2(30.0g,195.3mmol)，联硼酸频哪醇酯(74.4g,293.0mmol)，1，4二氧六环(600mL)，乙酸钾(38.3g，390.70mmol),x-phos(1.8g，3.9mmol)，Pd 2(dba) 3(1.7g，1.9mmol)，加热至95-105℃回流反应14h，反应结束后，冷却至室温。加入甲苯和水萃取反应溶液，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏浓缩，生成物用乙醇打浆，过滤得到中间体sub 1-I-B7(29.2g，61％)。
Figure PCTCN2021112354-appb-000083
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入中间体sub 1-I-B7(25.0g，102.0mmol),2,4-二氯-6-苯基-1,3,5-三嗪(23.0g，102.0mmol)(反应物C-13)，四(三苯基膦)钯(2.3g，2.0mmol)，碳酸钾(28.2g，204.0mmol)，四丁基溴化铵(0.6g，2.0mmol)，四氢呋喃(100ml)和去离子水(25ml)；开启搅拌和加热，待温度上升到60-70℃，回流反应10h，反应结束后，冷却至室温。用甲苯和水进行萃取，合并有机相，用无水硫酸镁进行干燥，过滤浓缩，使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体中间体sub B-7(17.3g，收率55％)。
(2)化合物667的合成
参照中间体sub B-7的合成方法，合成下表8所示的中间体，其中反应物C-X(X为19或20)代替反应物C-19，反应物B-X(X为7或11)代替反应物B-7，合成如下表8所示的中间 体sub B-X(X为8或9)。
表8
Figure PCTCN2021112354-appb-000084
参照化合物121的合成方法，合成下表9所示的化合物，其中，中间体sub A-X(X为19-21)代替中间体sub A-19，中间体sub B-X(X为7-8)代替中间体sub B-1，合成如下表9所示的化合物。
表9
Figure PCTCN2021112354-appb-000085
Figure PCTCN2021112354-appb-000086
制备例51：化合物664的合成
(1)中间体sub A-29的合成
Figure PCTCN2021112354-appb-000087
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，依次加入(5-氯-3-联苯)硼酸(45.0g，193.5mmol)(反应物A-5),2-氯苯并噁唑(29.7g，193.5mmol)(反应物A-7)，四(三苯基膦)钯(4.4g，3.8mmol)，碳酸钾(53.5g，387.1mmol)，四丁基溴化铵(1.2g，3.8mmol)，四氢呋喃(180)和去离子水(45ml)；开启搅拌和加热，待温度上升到66℃，回流反应15h，反应结束后，冷却至室温。用甲苯和水进行萃取，合并有机相，用无水硫酸镁进行干燥，过滤浓缩，使用二氯甲烷/正庚烷体系对粗品进行硅胶柱色谱提纯，得到固体中间体sub A-I-29(32.5g，收率55％)。
Figure PCTCN2021112354-appb-000088
向装有机械搅拌、温度计、球形冷凝管的三口瓶中通入氮气(0.100L/min)置换15min，加入中间体sub A-I-29(20.0g,65.4mmol)、吲哚并[2,3-A]咔唑(20.1g,78.5mmol)、Pd 2(dba) 3(0.6g，0.6mmol)、三叔丁基膦(0.3g,1.3mmol)、叔丁醇钠(12.5g,130.8mmol)、二甲苯(200mL)。开启搅拌并加热，待温度上升到140℃，回流反应5h，反应结束后，冷却至室温。反应液水洗后分离有机相，使用无水硫酸镁干燥有机相，过滤后将滤液减压蒸馏除去溶剂，使用二氯甲烷/乙醇体系对粗品进行重结晶，得到白色固体中间体sub A-29(20.9g,61％)。
参照中间体sub A-I-29的合成方法，合成下表10所示的中间体，其中反应物A-X(4、12、13或15)代替反应物A-5，合成如下表10所示的中间体sub A-I-X(X为30-33)。参照中间体sub A-29的合成方法，合成如下表10所示的中间体sub A-X(X为30-33)。
表10
Figure PCTCN2021112354-appb-000089
Figure PCTCN2021112354-appb-000090
(2)化合物664的合成
参照化合物67的合成方法，合成下表11所示的化合物，其中，中间体sub A-X(X为29-33)代替中间体sub A-1，其中反应物C-X(X为1、2或4)代替反应物C-1，合成如下表11所示的化合物。
表11
Figure PCTCN2021112354-appb-000091
Figure PCTCN2021112354-appb-000092
部分化合物核磁数据如下表12所示
表12
Figure PCTCN2021112354-appb-000093
Figure PCTCN2021112354-appb-000094
有机电致发光器件的制备和性能评估
实施例1
绿色有机电致发光器件
将厚度为110nm的阳极100ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阴极200、阳极100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100(实验基板)的功函数，并采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的浮渣及油污。
在实验基板上真空蒸镀化合物HAT-CN(结构式见下文)以形成厚度为10nm的空穴注入层310(HIL)；并在空穴注入层310上方真空蒸镀化合物NPB，以形成厚度为115nm的第一空穴传输层321(HTL1)。
在第一空穴传输层321(HTL1)上真空蒸镀一层TCBPA，形成厚度为35nm的第二空穴传输层322(HTL2)。
在第二空穴传输层322(HTL2)上，将化合物67：GH-P1：Ir(ppy) 2acac以45％：50％：5％膜厚比例进行共同蒸镀，形成厚度为38nm的绿色发光层330(G-EML)。
将HNBphen和LiQ以1:1的重量比进行混合并蒸镀形成30nm厚的电子传输层350(ETL)，接着将Yb蒸镀在电子传输层上，形成厚度为1nm的电子注入层360(EIL)。
将镁(Mg)和银(Ag)以1:9的膜厚比真空蒸镀在电子注入层上，形成厚度为13nm的阴极200。
此外，在上述阴极200上作为保护层蒸镀一层厚度为65nm的CP-1，形成覆盖层(CPL)，从而完成有机发光器件的制造。
其中，HAT-CN、NPB、TCBPA、GH-P1、Ir(ppy) 2acac、HNBphen、LiQ、CP-1的结构式如下表13所示：
表13
Figure PCTCN2021112354-appb-000095
Figure PCTCN2021112354-appb-000096
实施例2-56
除了在形成发光层(EML)时，采用表14中所示的化合物替代化合物67以外，采用与实施例1相同的方法制作绿色有机电致发光器件。
比较例1
利用化合物A替代化合物67，采用与实施例1相同的方法制作绿色有机电致发光器件。
比较例2
利用化合物B替代化合物67，采用与实施例1相同的方法制作绿色有机电致发光器件。
比较例3
利用化合物C替代化合物67，采用与实施例1相同的方法制作绿色有机电致发光器件。
比较例4
利用化合物D替代化合物67，采用与实施例1相同的方法制作绿色有机电致发光器件。
对如上制得的有机电致发光器材，在10mA/cm 2的条件下测试了器件的IVL性能，T95器件寿命在20mA/cm 2的条件下进行测试，其结果示于表14。
表14 绿色有机电致发光器件的性能测试结果
Figure PCTCN2021112354-appb-000097
Figure PCTCN2021112354-appb-000098
根据表14的结果可知，在化合物作为有机电致发光层的OLED器件中，与比较例相比，实施例1-56制备的有机电致发光器件的各项性能均有所提高。其中，作为发光层的化合物的实施例1-56 与现有技术中的化合物所对应的器件比较例1-4相比，本申请中使用的化合物作为发光层制备的上述有机电致发光器件的发光效率(Cd/A)至少提高了22.4％，外量子效率EQE(％)至少提高了22.9％，寿命最少的提高到了27.8％。由上述数据可知，采用本申请的含氮化合物作为电子元件的有机电致发光层，该电子元件的发光效率(Cd/A)、外量子效率(EQE)以及寿命(T95)都有显著的提高。因此，在有机电致发光层中使用本申请的含氮化合物可制备得到高发光效率、长寿命的有机电致发光器件。

Claims (14)

  1. 一种含氮化合物，其特征在于，所述含氮化合物的结构通式如式1所示：
    Figure PCTCN2021112354-appb-100001
    其中，
    Figure PCTCN2021112354-appb-100002
    表示化学键，A、B相同或不同，分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基、式2-1所示结构或式2-2所示结构，且A和B中至少有一个选自式2-1所示结构或式2-2所示结构；
    U 1、U 2和U 3相同或不同，分别独立地选自N或C(R)，且U 1、U 2和U 3中的至少一个为N；
    各R、R 1、R 2、R 3、R 4、R 5分别独立地选自氢、氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为1-5的卤代烷基、碳原子数为3-10的环烷基；
    n 1表示取代基R 1的个数，n 1选自1、2或3，当n 1大于1时，任意两个R 1相同或不同；
    n 2表示取代基R 2的个数，n 2选自1、2、3或4，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；
    n 3表示取代基R 3的个数，n 3选自1、2、3或4，当n 3大于1时，任意两个R 3相同或不同；
    n 4表示取代基R 4的个数，n 4选自1或2，当n 4大于1时，任意两个R 4相同或不同；
    n 5表示取代基R 5的个数，n 5选自1、2、3或4，当n 5大于1时，任意两个R 5相同或不同；
    X选自S或O；
    L、L 1、L 2、L 3和L 4相同或不同，且分别独立地选自单键、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；
    Ar 1和Ar 2相同或不同，且分别独立地选自碳原子数为6-30的取代或未取代的芳基、碳原子数为3-30的取代或未取代的杂芳基；
    所述A、B、L、L 1、L 2、L 3、L 4、Ar 1和Ar 2中的取代基相同或不同，且分别独立地选自氘、卤素基团、氰基、碳原子数为3-20的杂芳基、碳原子数为6-20的芳基、碳原子数为3-12的三烷基硅基、碳原子数为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；
    任选地，在Ar 1和Ar 2中，任意两个相邻的取代基形成环。
  2. 根据权利要求1所述的含氮化合物，其特征在于，各R、R 1、R 2、R 3、R 4、R 5独立地选自氢、氘、氟、氰基、甲基、乙基、正丙基、异丙基、叔丁基、苯基、吡啶基、三氟甲基、联苯基，或者，任意两个相邻的R 2形成苯环、萘环或菲环。
  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、L 2、L 3和L 4相同或不同，且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、或者碳原子数为5-20的取代或未取代的亚杂芳基。
  4. 根据权利要求1所述的含氮化合物，其特征在于，所述L、L 1、L 2、L 3和L 4相同或不同，且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、取代或未取代的亚吡啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚芴基、取代或未取代的亚咔唑基、取代或未取代的亚蒽基；
    优选地，所述L、L 1、L 2、L 3和L 4中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为1-5的烷基。
  5. 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、L 2、L 3和L 4相同或不同，且分别独立地选自单键或者取代或未取代的基团V，未取代的基团V选自如下基团所组成的组：
    Figure PCTCN2021112354-appb-100003
    其中，
    Figure PCTCN2021112354-appb-100004
    表示化学键；取代的基团V上具有一个或多个取代基，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基或苯基；当V的取代基个数大于1时，各取代基相同或不同。
  6. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1、Ar 2各自独立地选自碳原子数为6-25的取代或未取代的芳基、或者碳原子数为4-20的取代或未取代的杂芳基；
    优选地，所述Ar 1中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基或碳原子数为3-10的环烷基；
    优选地，所述Ar 2中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子数为1-5的卤代烷基、碳原子数为3-10的环烷基，所述Ar 2中任意两个相邻的取代基任选地形成碳原子数为5-13的饱和或不饱和环。
  7. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1、Ar 2各自独立地选自取代或未取代的基团W 1，未取代的W 1选自如下基团组成的组：
    Figure PCTCN2021112354-appb-100005
    Figure PCTCN2021112354-appb-100006
    其中，
    Figure PCTCN2021112354-appb-100007
    表示化学键；取代的基团W 1上具有一个或多个取代基，所述取代基各自独立地选自氘、氰基、氟、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基或咔唑基；当W 1的取代基个数大于1时，各取代基相同或不同。
  8. 根据权利要求1所述的含氮化合物，其特征在于，所述Ar 1、Ar 2各自独立地选自取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的二苯并呋喃基，取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的N-苯基咔唑基、取代或未取代的咔唑基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的芘基、取代或未取代的喹啉基、取代或未取代异喹啉基、取代或未取代的菲咯啉基、取代或未取代的苯并菲基、取代或未取代的呋喃基、取代或未取代的噻吩基或以下取代或未取代的基团：
    Figure PCTCN2021112354-appb-100008
  9. 根据权利要求1所述的含氮化合物，其特征在于，所述A、B分别独立地选自碳原子数为6-25的取代或未取代的芳基、碳原子数为5-20的取代或未取代的杂芳基、式2-1所示结构或式2-2所示结构，且A和B中有且仅有一个选自式2-1所示结构或式2-2所示结构；
    优选地，所述A、B中的取代基分别独立地选自氘、卤素基团、氰基、碳原子数为6-12的芳基、碳原子数为5-12的杂芳基、碳原子数为1-5的烷基、碳原子3-10的环烷基。
  10. 根据权利要求1所述的含氮化合物，其特征在于，所述A、B分别独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的吡啶基、取代或未取代的苯并菲基、取代或未取代的螺二芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的芴基、取代或未取代的芘基、取代或未取代的菲咯啉基、式2-1所示结构或式2-2所示结构，且A和B中有且仅有一个选自式2-1所示结构或式2-2所示结构；
    优选地，所述A、B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、萘基、联苯基、吡啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、环戊烷基、环己烷基。
  11. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下化合物所形成的组：
    Figure PCTCN2021112354-appb-100009
    Figure PCTCN2021112354-appb-100010
    Figure PCTCN2021112354-appb-100011
    Figure PCTCN2021112354-appb-100012
    Figure PCTCN2021112354-appb-100013
    Figure PCTCN2021112354-appb-100014
    Figure PCTCN2021112354-appb-100015
    Figure PCTCN2021112354-appb-100016
    Figure PCTCN2021112354-appb-100017
    Figure PCTCN2021112354-appb-100018
    Figure PCTCN2021112354-appb-100019
    Figure PCTCN2021112354-appb-100020
    Figure PCTCN2021112354-appb-100021
    Figure PCTCN2021112354-appb-100022
    Figure PCTCN2021112354-appb-100023
    Figure PCTCN2021112354-appb-100024
    Figure PCTCN2021112354-appb-100025
    Figure PCTCN2021112354-appb-100026
    Figure PCTCN2021112354-appb-100027
    Figure PCTCN2021112354-appb-100028
    Figure PCTCN2021112354-appb-100029
    Figure PCTCN2021112354-appb-100030
    Figure PCTCN2021112354-appb-100031
    Figure PCTCN2021112354-appb-100032
    Figure PCTCN2021112354-appb-100033
    Figure PCTCN2021112354-appb-100034
  12. 一种电子元件，其特征在于，所述电子元件包括阳极、阴极、以及介于阳极与阴极之间的至少一层功能层，所述功能层包含权利要求1-11中任意一项所述的含氮化合物；
    优选地，所述功能层包括发光层，所述发光层包括所述含氮化合物。
  13. 根据权利要求12所述的电子元件，其特征在于，所述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。
  14. 一种电子装置，其特征在于，包括权利要求12或13所述的电子元件。
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