WO2022100194A1 - 含氮化合物、有机电致发光器件和电子装置 - Google Patents

含氮化合物、有机电致发光器件和电子装置 Download PDF

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WO2022100194A1
WO2022100194A1 PCT/CN2021/113867 CN2021113867W WO2022100194A1 WO 2022100194 A1 WO2022100194 A1 WO 2022100194A1 CN 2021113867 W CN2021113867 W CN 2021113867W WO 2022100194 A1 WO2022100194 A1 WO 2022100194A1
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carbon atoms
substituted
unsubstituted
nitrogen
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French (fr)
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马天天
张孔燕
李昕轩
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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, and in particular, to a nitrogen-containing compound, an organic electroluminescent device using the nitrogen-containing compound, and an electronic device using the organic electroluminescent device.
  • Organic electroluminescent devices also known as organic light-emitting diodes, refer to the phenomenon that organic light-emitting materials emit light when excited by an electric current under the action of an electric field. It is a process of converting electrical energy into light energy.
  • organic electroluminescent diodes Compared with inorganic light-emitting materials, organic electroluminescent diodes (OLEDs) have the advantages of active light emission, large optical path range, low driving voltage, high brightness, high efficiency, low energy consumption and simple manufacturing process. It is because of these advantages that organic light-emitting materials and devices have become one of the most popular research topics in the scientific and industrial circles.
  • An organic electroluminescence device 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.
  • CN 107445910 A, CN 108884059 A, CN 109641840 A, CN 110540527 A. etc. disclose light-emitting layer materials that can be used in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
  • the purpose of the present application is to provide a nitrogen-containing compound, an organic electroluminescent device and an electronic device, so as to improve the performance of the organic electroluminescent device and the electronic device.
  • a first aspect of the present application provides a nitrogen-containing compound, the structure of which is shown in formula 1:
  • X 1 is selected from O or S;
  • X 2 , X 3 , X 4 and X 5 are the same or different from each other, and are each independently selected from C(H) or N;
  • L and L 1 are 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;
  • Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkanes with 1-20 carbon atoms base, substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
  • the substituents in L, L 1 and Ar are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, optionally replaced by 0, 1 , 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl aryl with 6-20 carbon atoms, and 3-12 carbon atoms
  • any two adjacent substituents form a ring.
  • the nitrogen-containing compounds provided in this application are based on triazine derivatives and phenanthrene as core structures.
  • the fused ring group of the phenanthrene is an aromatic structure with 10 ⁇ electrons, which has a stable planar structure.
  • the triazine derivative is substituted at the 4-position of the phenanthrene.
  • the compound substituted at the 4-position has a larger twisted dihedral angle, which reduces the degree of conjugation of the nitrogen-containing compound structure, so that the material has a higher T1 value; at the same time, the steric hindrance of the material is increased, the intermolecular force is reduced, and the evaporation temperature of the material is reduced under the same molecular weight, which can effectively reduce the performance degradation of organic electroluminescent devices caused by crystallization.
  • triazine derivatives can effectively enhance the electronegativity of compounds and improve the electron transport properties of compounds.
  • a second aspect of the present application provides an organic electroluminescence device, the organic electroluminescence device comprising an anode and a cathode disposed oppositely, and a functional layer disposed between the anode and the cathode; the functional layer comprises The nitrogen-containing compound of the first aspect;
  • the functional layer includes an organic electroluminescence layer, and the organic electroluminescence layer includes the nitrogen-containing compound.
  • a third aspect of the present application provides an electronic device including the organic electroluminescence device of the second aspect.
  • 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.
  • 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 first aspect of the present application provides a nitrogen-containing compound, and the structure of the nitrogen-containing compound is shown in formula 1:
  • X 1 is selected from O or S;
  • X 2 , X 3 , X 4 and X 5 are the same or different from each other, and are each independently selected from C(H) or N;
  • L and L 1 are 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;
  • Ar is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkane groups with 1-20 carbon atoms base, substituted or unsubstituted cycloalkyl with 3-20 carbon atoms;
  • the substituents in L, L 1 and Ar are the same or different from each other, and are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, optionally replaced by 0, 1 , 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl aryl with 6-20 carbon atoms, and 3-12 carbon atoms
  • any two adjacent substituents form a ring.
  • any two adjacent substituents form a ring; means that the two substituents may form a ring but need not form a ring, including: scenarios where two adjacent substituents form a ring and two A scenario where adjacent substituents do not form a ring.
  • the number of carbon atoms optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl is 6
  • Aryl group of ⁇ 20 means that the aryl group may be substituted by one or more of deuterium, fluorine, cyano, methyl, and tert-butyl, and may not be substituted by deuterium, fluorine, cyano, methyl, tert-butyl Substitution, and when the number of substituents on the aryl group is 2 or more, the substituents may be the same or different.
  • any two adjacent substituents may include two substituents on the same atom, and may also include two adjacent atoms each having 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 one substituent respectively, The two substituents can be fused to form a ring.
  • a saturated or unsaturated ring with 5-14 ring carbon atoms can be formed, for example: Benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, cyclopentane, cyclohexane, adamantane, etc.
  • 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.
  • the number of carbon atoms of L, L 1 and Ar refers to all the number of carbon atoms.
  • 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.
  • Ar is Then the number of carbon atoms is 7; L is Its total number of carbon atoms is 12.
  • hetero refers to a functional group including at least 1 heteroatom such as B, N, O, S, Se, Si or P 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 may have 1 to 20 carbon atoms, and in this application, a numerical range such as “1 to 20” refers to each integer in the given range; for example, “1 to 20 carbon atoms” means that 1 may be included 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, Alkyl groups of 18, 19 or 20 carbon atoms.
  • alkyl groups can be substituted or unsubstituted.
  • the alkyl group is selected from alkyl groups with 1-5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec- Butyl, tert-butyl, pentyl.
  • 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.
  • a bicyclic fused aryl group eg, naphthyl
  • a tricyclic fused aryl group eg, phenanthrenyl, fluorenyl, anthracenyl
  • biphenyl, terphenyl, etc. are aryl groups.
  • 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 may contain 6-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group is 6-25, in other embodiments The number of carbon atoms in the substituted or unsubstituted aryl group is 6-18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group is 6-13.
  • the number of carbon atoms of a substituted or unsubstituted aryl group can be 6, 12, 13, 14, 15, 18, 20, 24, 25, 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, 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.
  • heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted pheny
  • 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 atoms of the substituents is 18.
  • aryl groups as substituents include but are not limited to: phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorene base and so on.
  • the fluorenyl group can be substituted, and the two substituent groups can be combined with each other to form a spiro structure.
  • Specific examples include but are not limited to the following structures:
  • heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring, and the heteroatoms can be B, O, N, P, At least one of Si, 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.
  • 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, and in other implementations In the examples, the number of carbon atoms in the substituted or unsubstituted heteroaryl group is 3-20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl group is 12-20.
  • a substituted or unsubstituted heteroaryl group may also have 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30 carbon atoms. 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, N-phenylcarbazolyl, 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: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthroline, etc. .
  • the halogen group may be fluorine, chlorine, bromine, iodine.
  • X 2 , X 3 , X 4 and X 5 are respectively C(H).
  • one of X 2 , X 3 , X 4 and X 5 is N, and the rest are C(H).
  • X 2 is N
  • X 3 , X 4 and X 5 are respectively C(H); or
  • X 3 is N, and X 2 , X 4 and X 5 are respectively C(H); or
  • X 4 is N and X 3 , X 2 and X 5 are each C(H); or
  • X 5 is N, and X 3 , X 2 and X 4 are each C(H).
  • two of X 2 , X 3 , X 4 and X 5 are N, and the rest are C(H).
  • X 2 and X 4 are N, and X 3 and X 5 are respectively C(H); or X 3 and X 5 are N, and X 2 and X 4 are respectively C(H).
  • three of X 2 , X 3 , X 4 and X 5 are N, and the rest are C(H).
  • L and L 1 are independently selected from a single bond, a substituted or unsubstituted arylene group with 6-20 carbon atoms, a substituted or unsubstituted arylene group with 5-20 carbon atoms Heteroarylene.
  • L and L 1 are independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted or unsubstituted pyridylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylide, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted Unsubstituted dibenzothienylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted anthracylene, substituted or unsubstituted N-phenylcarbazoleidene;
  • L L 1 can also be selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted Unsubstituted biphenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylylene, substituted or unsubstituted Dibenzofuranyl, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted anthracylene, and substituted or unsubstituted N-phenylcarbazolylide
  • a group formed after any two groups are connected by a single bond, the connection by a single bond means that any two groups are connected
  • the substituents in the L and L 1 are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, Heteroaryl with 5-12 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, carbazolyl.
  • L and L 1 are independently selected from the group consisting of a single bond or a group represented by formula j-1 to formula j-14:
  • M 2 is selected from single bond or
  • Q 1 to Q 5 and Q' 1 to Q' 5 are each independently selected from N or C(J 5 ), and at least one of Q 1 to Q 5 is selected from N; when two or more of Q 1 to Q 5 are selected from N; When selected from C(J 5 ), any two J 5 are the same or different, and when two or more of Q' 1 to Q' 4 are selected from C(J 5 ), any two J 5 are the same or different ;
  • Q 6 to Q 13 are each independently selected from N, C or C(J 6 ), and at least one of Q 6 to Q 13 is selected from N; when two or more of Q 6 to Q 13 are selected from C(J 6 ) ), any two J 6 are the same or different;
  • Q 14 to Q 23 are each independently selected from N, C or C(J 7 ), and at least one of Q 14 to Q 23 is selected from N; when two or more of Q 14 to Q 23 are selected from C(J 7 ) ), any two J 7 are the same or different;
  • Q 24 to Q 33 are each independently selected from N, C or C(J 8 ), and at least one of Q 24 to Q 33 is selected from N; when two or more of Q 24 to Q 33 are selected from C(J 8 ) ), any two J 8 are the same or different;
  • E 1 -E 14 , J 5 -J 9 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, heteroaryl group with 3-20 carbon atoms, optionally by 0, 1, 2, Aryl groups having 6 to 20 carbon atoms, substituted by 3, 4 or 5 substituents independently selected from deuterium, fluorine, chlorine, cyano, methyl and tert-butyl groups, and aryl groups having 3 to 12 carbon atoms Trialkylsilyl, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, heterocycle with 2 to 10 carbon atoms Alkyl group, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, aryloxy group with 6 to 18 carbon atoms, arylthio group with 6 to 18 carbon atoms , a phosphineoxy group with
  • E 1 to E 14 when any one of E 1 to E 14 is independently selected from an aryl group having 6 to 20 carbon atoms, E 1 to E 3 and E 14 are not aryl groups;
  • e 1 to e 14 are represented by er, E 1 to E 14 are represented by Er , r is a variable, representing any integer from 1 to 14, and er represents the number of substituents E r ; when r is selected from 1, 2, When 3, 4, 5, 6, 9, 13 or 14, er is selected from 1, 2, 3 or 4; when r is selected from 7 or 11, er is selected from 1, 2, 3, 4, 5 or 6; when r is 12, er is selected from 1, 2, 3, 4, 5, 6 or 7; when r is selected from 8 or 10, er is selected from 1, 2, 3, 4, 5, 6 , 7 or 8; when er is greater than 1, any two Er are the same or different;
  • K 3 is selected from O, S, Se, N(E 15 ), C(E 16 E 17 ), Si(E 18 E 19 ); wherein, E 15 , E 16 , E 17 , E 18 and E 19 are each independently is selected from the group consisting of: an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, an alkyl group with 1-10 carbon atoms, a cycloalkyl group with 3-10 carbon atoms, Heterocycloalkyl with 2 to 10 carbon atoms, or E 16 and E 17 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 18 and E 19 Connected to each other to form saturated or unsaturated rings with 3 to 15 carbon atoms with the atoms they are commonly connected to;
  • K 4 is selected from single bond, O, S, Se, N(E 20 ), C(E 21 E 22 ), Si(E 23 E 24 ); wherein, E 20 to E 24 are each independently selected from: carbon atom Aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, and 2 to 2 carbon atoms 10 heterocycloalkyl, or E 21 and E 22 are connected to each other to form a saturated or unsaturated ring with 3 to 15 carbon atoms, or E 23 and E 24 are connected to each other to form a common connection with them The connected atoms form a saturated or unsaturated ring having 3 to 15 carbon atoms.
  • L and L 1 are each independently selected from a single bond, a substituted or unsubstituted group V; the 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, fluorine, cyano, halogen, methyl, ethyl, n-propyl, isopropyl propyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, carbazolyl group; when the number of substituent groups in group V is greater than 1, each substituent group is the same or different.
  • L and L 1 are independently selected from the group consisting of a single bond or the following groups, but are not limited thereto:
  • Ar is selected from a substituted or unsubstituted aryl group with 6-26 carbon atoms, and a substituted or unsubstituted heteroaryl group with 5-20 carbon atoms.
  • the substituents in the Ar are selected from deuterium, fluorine, cyano, alkyl groups with 1-5 carbon atoms, aryl groups with 6-20 carbon atoms, and aryl groups with 12-18 carbon atoms. Heteroaryl, cycloalkyl with 5-10 carbon atoms;
  • any two adjacent substituents form a saturated or unsaturated ring with 5-8 carbon atoms.
  • substituents in Ar include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cycloethyl, Phenyl, phenanthryl, naphthyl, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, carbazolyl, N-phenylcarbazolyl, cyclohexyl, cyclopentyl Alkyl, adamantyl, etc.
  • the substituents in Ar form cyclopentane and cyclohexane.
  • Ar is selected from the groups represented by the following formula i-1 to formula i-15:
  • M 1 is selected from single bond or
  • G 1 to G 5 and G' 1 to G' 4 are each independently selected from N, C or C(J 1 ), and at least one of G 1 to G 5 is selected from N; when two of G 1 to G 5 are selected from N; When more than one is selected from C(J 1 ), any two J 1 are the same or different;
  • G 6 to G 13 are each independently selected from N, C or C(J 2 ), and at least one of G 6 to G 13 is selected from N; when two or more of G 6 to G 13 are selected from C(J 2 ) ), any two J 2 are the same or different;
  • G 14 to G 23 are each independently selected from N, C or C(J 3 ), and at least one of G 14 to G 23 is selected from N; when two or more of G 14 to G 23 are selected from C(J 3 ) ), any two J 3 are the same or different;
  • G 24 to G 33 are each independently selected from N, C or C(J 4 ), and at least one of G 24 to G 33 is selected from N; when two or more of G 24 to G 33 are selected from C(J 4 ) ), any two J 4 are the same or different;
  • Z 1 is selected from hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group with 3-12 carbon atoms, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms , cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio group with 1-10 carbon atoms, triarylsilyl with 18-24 carbon atoms;
  • Z 2 to Z 9 and Z 21 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group with 3-12 carbon atoms, triarylsilicon group with 18-24 carbon atoms group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, carbon atom Alkylthio group with 1-10 carbon atoms, alkylthio group with carbon number of 1-10, heteroaryl group with carbon number of 3-18;
  • Z 10 -Z 20 and J 1 -J 4 are each independently selected from: hydrogen, deuterium, halogen group, cyano group, trialkylsilyl group having 3-12 carbon atoms, and Alkyl, halogenated alkyl group with 1 to 10 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, The number of carbon atoms optionally substituted by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, chlorine, cyano, methyl, ethyl, tert-butyl is 6 ⁇
  • h 1 to h 21 are represented by h k
  • Z 1 to Z 21 are represented by Z k
  • k is a variable, representing any integer from 1 to 21
  • h k represents the number of substituents Z k ; wherein, when k is selected from 5 or 17, h k is selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h k is selected from 1, 2, 3 or 4; when k is selected from When from 1, 3, 4, 6, 9 or 14, h k is selected from 1, 2, 3, 4 or 5; when k is 13, h k is selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h k is selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h k is selected from 1, 2, 3, 4, 5, 6, 7 or 8; when k is 11, h k is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h k is greater than 1, any two Z k are the same or different;
  • K 1 is selected from O, S, N(Z 22 ), C(Z 23 Z 24 ), Si(Z 28 Z 29 ); wherein Z 22 , Z 23 , Z 24 , Z 28 , Z 29 are independently selected from each other From: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms, or the above Z 23 and Z 24 are connected to each other to form a saturated or unsaturated ring with a carbon number of 3-15 with their commonly connected atoms, or the above Z 28 and Z 29 are connected to each other to form a carbon number with their commonly connected atoms is a saturated or unsaturated ring of 3-15;
  • K 2 is selected from single bond, O, S, N(Z 25 ), C(Z 26 Z 27 ), Si(Z 30 Z 31 ); wherein Z 25 , Z 26 , Z 27 , Z 30 , Z 31 are each Independently selected from: aryl group with 6-18 carbon atoms, heteroaryl group with 3-18 carbon atoms, alkyl group with 1-10 carbon atoms, or cycloalkyl group with 3-10 carbon atoms , or the above-mentioned Z 26 and Z 27 are connected to each other to form a saturated or unsaturated ring with a carbon number of 3-15 with the atoms they are commonly connected to, or the above-mentioned Z 30 and Z 31 are connected to each other to form with their commonly connected atoms A saturated or unsaturated ring having 3-15 carbon atoms.
  • the ring refers to a saturated or unsaturated ring, such as etc., but not limited to this.
  • Ar is selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of:
  • the substituted group W has one or more substituents, each of which is independently selected from: deuterium, fluorine, cyano, halogen, methyl, ethyl, n-propyl, isopropyl propyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, cyclopentyl group, cyclohexane group; when the number of substituents in group W is greater than 1, the substituents are the same or different.
  • Ar is selected from the group consisting of, but is not limited to:
  • the nitrogen-containing compound is selected from the group consisting of, but is not limited to:
  • the present application also 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 nitrogen-containing compound of the present application.
  • the organic electroluminescent device includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the nitrogen compounds.
  • the organic electroluminescent device may be, for example, a green organic electroluminescent device.
  • the functional layer 300 includes an organic electroluminescence layer 330, and the organic electroluminescence layer 330 includes the nitrogen-containing compound of the present application.
  • 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 injected into the organic electroluminescent layer 330 and the electrons injected into the organic electroluminescent layer 330 can be recombined in the organic electroluminescent layer 330 to form excitation. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
  • the host material of the organic electroluminescent layer 330 can be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specially made in this application. limits.
  • the host material of the organic electroluminescent layer 330 is a mixture of the compound of the present application and other compounds, such as GH-P1.
  • the guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative or other materials.
  • the guest material of the organic electroluminescent layer 330 is Ir(npy) 2 acac.
  • the organic electroluminescence device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescence layer 330 serving as an energy conversion layer, and an electron transport layer, which are stacked in sequence. 350 and cathode 200.
  • the nitrogen-containing compound provided in the present application can be applied to the organic electroluminescent layer 330 of an organic electroluminescent device, and can effectively improve the luminous efficiency and lifetime of the organic electroluminescent device.
  • 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 321 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds. This does not make special restrictions.
  • the hole transport layer 321 is composed of the compound NPB.
  • the electron blocking layer 322 includes one or more electron blocking materials, the electron blocking layer is also referred to as the second hole transport property, and the electron blocking material can be selected from carbazole polymers or other types of compounds. No special restrictions.
  • electron blocking layer 322 consists of TCBPA.
  • 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 340 may be composed of TPyQB 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 multilayer 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 magnesium and silver is preferably included as the cathode.
  • a hole injection layer 310 may also be disposed between the anode 100 and the hole transport layer 321 to enhance the capability of injecting holes into the hole transport layer 321 .
  • the hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not 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 Yb (ytterbium).
  • a hole blocking layer 340 may also be disposed between the organic electroluminescent layer 330 and the electron transport layer 350 .
  • Embodiments of the present application further provide an electronic device including the above organic electroluminescence device. Since the electronic device has the above-mentioned organic electroluminescence device, it has the same beneficial effects, and details are not described here in this application.
  • the present application provides an electronic device 400 , and the electronic device 400 includes the above-mentioned organic electroluminescence device.
  • the electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like. Since the electronic device 400 has the above-mentioned organic electroluminescence device, it has the same beneficial effects, and details are not described herein again.
  • the intermediate sub A-1 was synthesized by the following synthetic route:
  • magnesium chips (2.9g, 120mmol) and 30mL of tetrahydrofuran solution were added to the three-necked flask, the temperature of the system was raised to 80°C, and iodine (0.6g, 2.4mmol) and 4-bromodibenzofuran were added to the system. (30.0 g, 120 mmol) was completely dissolved in 30 mL of THF solution to form the mixture, slowly added dropwise to the system within 30 min, and the temperature was controlled at 80° C. during the dropwise addition. After the dropwise addition was completed, the reaction was stirred at 80 °C for 2 h.
  • magnesium flakes (1.52 g, 63.7 mmol) and 30 mL of tetrahydrofuran solution were added to the three-necked flask, the temperature of the system was raised to 80 °C, and iodine (0.32 g, 1.26 mmol) and 4-bromodibenzo were added to the system.
  • Furan ((15.73g, 63.7mmol) was completely dissolved in 30mL of THF solution to form the mixture, slowly added dropwise to the system within 30min, and the temperature was controlled at 80°C during the dropwise addition. The reaction was stirred under the conditions for 2h.
  • the intermediate aI-1 (20.13g, 63.7mmol) dissolved in 40mL of THF was added dropwise to the mixed solution, and the reaction was terminated after stirring for 3h. After the reaction was completed, toluene and water were added to carry out The reaction solution was extracted, the organic phases were combined, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated by distillation under reduced pressure; the crude product was purified by silica gel column chromatography, recrystallized from methanol and filtered to obtain a solid intermediate sub A-1 (22.5 g, 79% ).
  • the intermediate sub B-1 was synthesized by the following synthetic route:
  • 4-Bromophenanthrene (50.0 g, 194.4 mmol), pinacol diboronate (74.1 g, 291.6 mmol), tris(dibenzylideneacetone)dipalladium (1.7 g, 1.9 mmol), 2-dicyclohexyl Phosphorus-2',4',6'-triisopropylbiphenyl (1.8g, 3.8mmol) and 1,4-dioxane (500mL) were added to a round-bottomed flask, and the temperature was raised to 100°C under nitrogen protection, Heated and stirred for 12h under reflux.
  • Intermediate sub A-1 (10.0 g, 22.3 mmol), intermediate sub B-1 (7.1 g, 23.4 mmol), tetrakis(triphenylphosphine)palladium (0.5 g, 0.4 mmol), potassium carbonate (6.2 g , 44.6mmol), tetrabutylammonium bromide (0.1g, 0.4mmol), toluene (80mL), ethanol (20mL) and deionized water (20mL) were added to the three-necked flask, heated to 76°C under nitrogen protection, heated to reflux Stir for 8h.
  • intermediates sub A-2 to sub A-17 shown in Table 1 were prepared, except that starting material A in table 1 was used instead of starting material 4 in the preparation of intermediate a-I-1 -Bromodibenzofuran, use raw material B in table 1 to replace the raw material 4-bromodibenzofuran in the preparation intermediate sub A-1.
  • the anode was prepared by the following process: an ITO substrate with an ITO 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 it with overlapping regions of anode and cathode.
  • the surface of the substrate can be treated by plasma such as ultraviolet, ozone, etc., so as to increase the work function of the anode.
  • the surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface.
  • HIL hole injection layer
  • NPB hole transport layer
  • Vacuum evaporation of TCBPA was performed on the hole transport layer to form an electron blocking layer with a thickness of 35 nm.
  • EML Organic Electroluminescent Layer
  • TPyQB and LiQ were mixed in a weight ratio of 1:1 and evaporated to form an electron transport layer (ETL) with a thickness of 28 nm.
  • ETL electron transport layer
  • EIL electron injection layer
  • Magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1:9 and vacuum-evaporated on the electron injection layer to form a cathode with a thickness of 14 nm.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compound shown in Table 4 was used instead of Compound 3 in Example 1 when the organic electroluminescent layer was formed.
  • An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compounds A, B, C, D, E, and F were used instead of Compound 3 in Example 1 when the organic electroluminescent layer was formed.
  • the performance of the green organic electroluminescent devices prepared in Examples 1 to 24 and Comparative Examples 1 to 6 was tested. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 . The T95 device life was 20 mA/cm 2 . The test was carried out under the conditions, and the test results are shown in Table 5.
  • the compounds of the present application are used as the host material of the N-type green organic electroluminescent layer in Examples 1-24.
  • the color coordinates are not much different.
  • the luminous efficiency Cd/A is increased by at least 18.5%
  • the external quantum efficiency is increased by at least 42.5%
  • the lifetime T95 is increased by at least 12.7%.
  • the nitrogen-containing compound of the present application when used to prepare a green organic electroluminescent device, the lifetime of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency of the organic electroluminescent device can be greatly improved.

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Abstract

本申请属于有机材料技术领域，提供了一种含氮化合物、有机电致发光器件和电子装置，该含氮化合物的结构如式(1)所示。

Description

含氮化合物、有机电致发光器件和电子装置
相关申请的交叉引用
本申请要求于2020年11月10日递交的申请号为202011249452.5的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。
技术领域
本申请涉及有机材料技术领域，尤其涉及一种含氮化合物、使用该含氮化合物的有机电致发光器件和应用该有机电致发光器件的电子装置。
背景技术
有机电致发光器件又称为有机发光二极管，是指有机发光材料在电场作用下，受到电流的激发而发光的现象。它是一种将电能转换为光能的过程。相比于无机发光材料，有机电致发光二极管OLED具有主动发光、光程范围大、驱动电压低、亮度大、效率高、耗能少以及制作工艺简单等优点。正是由于这些优点，有机发光材料与器件已经成为科学界和产业界十分热门的科研课题之一。
有机电致发光器件一般包括依次层叠设置的阳极、空穴传输层、作为能量转化层的电致发光层、电子传输层和阴极。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向电致发光层移动，阳极侧的空穴也向发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得电致发光层对外发光。
现有技术中，CN 107445910 A、CN 108884059 A、CN 109641840 A、CN 110540527 A.等公开了可以在有机电致发光器件中使用的发光层材料。然而，依然有必要继续研发新型的材料，以进一步提高电子元器件的性能。
所述背景技术部分申请的上述信息仅用于加强对本申请的背景的理解，因此它可以包括不构成对本领域普通技术人员已知的现有技术的信息。
发明内容
本申请的目的在于提供一种含氮化合物、有机电致发光器件和电子装置，以改善有机电致发光器件和电子装置的性能。
为实现上述发明目的，本申请采用如下技术方案：
本申请的第一方面，提供一种含氮化合物，所述含氮化合物的结构如式1所示：
Figure PCTCN2021113867-appb-000001
其中，X 1选自O或S；
X 2、X 3、X 4和X 5彼此相同或不同，且各自独立地选自C(H)或N；
L和L 1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、 碳原子数为1-20的取代或未取代的烷基、碳原子数为3-20的取代或未取代的环烷基；
L、L 1和Ar中的各取代基彼此相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、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L、L 2和Ar中，任选地，任意两个相邻的取代基形成环。
本申请提供的含氮化合物，基于三嗪衍生物和菲为核心结构。其中，菲的稠环基团为具有10个π电子的芳香族结构，其具有稳定的平面结构。三嗪衍生物在菲的4位进行取代，相比其他位置取代，4位取代的化合物具有较大的扭曲二面角，降低了含氮化合物结构的共轭程度，从而使材料具有较高的T1值；同时增加了材料的空间位阻，降低分子间作用力，使材料在相同分子量情况下，蒸镀温度下降，能有效减少由结晶导致的有机电致发光器件的性能降低。此外，三嗪衍生物能有效增强化合物的电负性、提高化合物的电子传输性能。将本申请含氮化合物用作有机电致发光器件的有机电致发光层的主体材料时，能有效提升器件的发光效率以及寿命。
本申请的第二方面提供一种有机电致发光器件，该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；所述功能层包含第一方面所述的含氮化合物；
优选地，所述功能层包括有机电致发光层，所述有机电致发光层包含所述的含氮化合物。
本申请的第三方面提供一种电子装置，该电子装置包括第二方面所述的有机电致发光器件。
附图说明
通过参照附图详细描述其示例实施方式，本申请的上述和其它特征及优点将变得更加明显。
图1是本申请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；321、空穴传输层；322、电子阻挡层；330、有机电致发光层；340、空穴阻挡层；350、电子传输层；360、电子注入层；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。
本申请第一方面提供一种含氮化合物，所述含氮化合物的结构如式1所示：
Figure PCTCN2021113867-appb-000002
其中，X 1选自O或S；
X 2、X 3、X 4和X 5彼此相同或不同，且各自独立地选自C(H)或N；
L和L 1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、碳原子数为1-20的取代或未取代的烷基、碳原子数为3-20的取代或未取代的环烷基；
L、L 1和Ar中的各取代基彼此相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、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L、L 2和Ar中，任选地，任意两个相邻的取代基形成环。
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，任意两个相邻的取代基形成环；”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，“任选地被0、1、2、3、4或5个独立地选自氘、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”是指芳基可以被氘、氟、氰基、甲基、叔丁基中的一个或多个取代，也可以不被氘、氟、氰基、甲基、叔丁基取代，且当芳基上的取代基的个数大于等于2时，取代基可以相同或不同。
在本申请中，“任意两个相邻的取代基形成环”中，“任意相邻”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有2个或2个以上的取代基时，且任意相邻的取代基形成环时，可以形成饱和或不饱和的成环碳原子数为5-14的环，例如：苯环、萘环、菲环、蒽环、环戊烷、环己烷、金刚烷等等。
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 PCTCN2021113867-appb-000003
其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。
在本申请中，L、L 1、Ar的碳原子数，指的是所有碳原子数。举例而言，若L选自碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。例如：Ar为
Figure PCTCN2021113867-appb-000004
则其碳原子数为7；L为
Figure PCTCN2021113867-appb-000005
其总碳原子数为12。
在本申请中，当没有另外提供具体的定义时，“杂”是指在一个官能团中包括至少1个B、N、O、S、Se、Si或P等杂原子且其余原子为碳和氢。未取代的烷基可以是没有任何双键或三键的“饱和烷基基团”。
在本申请中，“烷基”可以包括直链烷基或支链烷基。烷基可具有1至20个碳原子，在本申请中，诸如“1至20”的数值范围是指给定范围中的各个整数；例如，“1至20个碳原子”是指可包含1个、2个、3个、4个、5个、6个、7个、8个、9个、10个、11个、12个、13个、14个、15个、16个、17个、18个、19个或20个碳原子的烷基。此外，烷基可为取代的或未取代的。
可选地，烷基选自碳原子数为1-5的烷基，具体施例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基。
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。举例而言，在本申请中，联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于，苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、四联苯基、五联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、
Figure PCTCN2021113867-appb-000006
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6-13个。举例而言，本申请中，取代或未取代芳基的碳原子数可以是6个、12个、13个、14个、15个、18个、20个、24个、25个、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。杂芳基取代的芳基的具体实例包括但不限于，二苯并呋喃基取代的苯基、二苯并噻吩取代的苯基、吡啶取代的苯基等。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、二苯基芴基、螺二芴基等等。
在本申请中，芴基可以是取代的，两个取代基可以彼此结合形成螺结构，具体施例包括但不限于以下结构：
Figure PCTCN2021113867-appb-000007
在本申请中，杂芳基是指环中包含1、2、3、4、5、6或7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-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”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，在另一些实施例中取代或未取代的杂芳基中的碳原子数是3-20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12-20个。举例而言，取代或未取代的杂芳基其碳原子数量还可以是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、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、N-苯基咔唑基等。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：二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、菲咯啉基等等。
在本申请中，卤素基团可以为氟、氯、溴、碘。
按照本申请一种实施方式，X 2、X 3、X 4和X 5分别为C(H)。
按照本申请另一种实施方式，X 2、X 3、X 4和X 5中的一者为N，其余为C(H)。例如X 2为N，X 3、X 4和X 5分别为C(H)；或者X 3为N，X 2、X 4和X 5分别为C(H)；或者X 4为N，X 3、X 2和X 5分别为C(H)；或者X 5为N，X 3、X 2和X 4分别为C(H)。
按照本申请另一种实施方式，X 2、X 3、X 4和X 5中的两者为N，其余为C(H)。例如X 2、X 4为N，X 3和X 5分别为C(H)；或者X 3、X 5为N，X 2和X 4分别为C(H)。
按照本申请另一种实施方式，X 2、X 3、X 4和X 5中的三者为N，其余为C(H)。
按照本申请一种实施方式，L和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、碳原子数为5-20的取代或未取代的亚杂芳基。
按照本申请另一种实施方式，L和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、取代或未取亚吡啶基、取代或未取代的亚喹啉基、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、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的N-苯基咔唑亚基；
或者，上述任意两个基团通过单键连接所形成的基团。
其中，“上述任意两个基团通过单键连接所形成的基团”是指：L、L 1也可以选自由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、取代或未取亚吡啶基、取代或未取代的亚喹啉基、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、取代或未取代的亚菲基、取代或未取代的亚蒽基和取代或未取代的N-苯基咔唑亚基中的任意两个基团通过单键连接后所形成的基团，通过单键连接是指任意两个基团通过自身的化学键
Figure PCTCN2021113867-appb-000008
相互连接。如取代或未取代的亚苯基
Figure PCTCN2021113867-appb-000009
通过自身的
Figure PCTCN2021113867-appb-000010
与取代或未取代的亚咔唑基
Figure PCTCN2021113867-appb-000011
的
Figure PCTCN2021113867-appb-000012
连接形成
Figure PCTCN2021113867-appb-000013
基团。
可选地，所述L和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、碳原子数为5-12的杂芳基。
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、咔唑基。
按照本申请一种实施方式，L和L 1分别独立地选自单键或式j-1至式j-14所示基团所组成的组：
Figure PCTCN2021113867-appb-000014
其中，M 2选自单键或者
Figure PCTCN2021113867-appb-000015
Q 1～Q 5和Q’ 1～Q’ 5各自独立地选自N或者C(J 5)，且Q 1～Q 5中至少一个选自N；当Q 1～Q 5中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同，当Q’ 1～Q’ 4中的两个以上选自C(J 5)时，任意两个J 5相同或者不相同；
Q 6～Q 13各自独立地选自N、C或者C(J 6)，且Q 6～Q 13中至少一个选自N；当Q 6～Q 13中的两个以上选自C(J 6)时，任意两个J 6相同或者不相同；
Q 14～Q 23各自独立地选自N、C或者C(J 7)，且Q 14～Q 23中至少一个选自N；当Q 14～Q 23中的两个以上选自C(J 7)时，任意两个J 7相同或者不相同；
Q 24～Q 33各自独立地选自N、C或者C(J 8)，且Q 24～Q 33中至少一个选自N；当Q 24～Q 33中的两个以上选自C(J 8)时，任意两个J 8相同或者不相同；
E 1～E 14、J 5～J 9各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基、甲基、叔丁基的取代基所取代的碳原子数为6～20的芳基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为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，碳原子数为18～24的三芳基硅基；任选地被0、1、2、3、4或5个独立地选 自氘、氟、氯、氰基、甲基、乙基、叔丁基的取代基所取代的碳原子数为6～20的芳基”是指芳基可以被氘、氟、氯、氰基、甲基、叔丁基中的一个或多个取代，也可以不被取代，且当芳基上的取代基的个数大于等于2时，取代基可以相同或不同。
其中，当E 1～E 14中的任意一个独立地选自碳原子数为6～20的芳基时，E 1～E 3和E 14不为芳基；
e 1～e 14以e r表示，E 1～E 14以E r表示，r为变量，表示1～14的任意整数，e r表示取代基E r的数量；当r选自1、2、3、4、5、6、9、13或14时，e r选自1、2、3或者4；当r选自7或11时，e r选自1、2、3、4、5或者6；当r为12时，e r选自1、2、3、4、5、6或者7；当r选自8或10时，e r选自1、2、3、4、5、6、7或者8；当e r大于1时，任意两个E r相同或者不相同；
K 3选自O、S、Se、N(E 15)、C(E 16E 17)、Si(E 18E 19)；其中，E 15、E 16、E 17、E 18和E 19各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、或者E 16和E 17相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 18和E 19相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环；
K 4选自单键、O、S、Se、N(E 20)、C(E 21E 22)、Si(E 23E 24)；其中，E 20至E 24各自独立地选自：碳原子数为6～20的芳基、碳原子数为3～20的杂芳基、碳原子数为1～10的烷基、碳原子数为3～10的环烷基、碳原子数为2～10的杂环烷基、或者E 21和E 22相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环，或者E 23和E 24相互连接以与它们共同连接的原子形成碳原子数为3～15的饱和或不饱和的环。
可选地，L和L 1分别独立地选自单键、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 PCTCN2021113867-appb-000016
其中，
Figure PCTCN2021113867-appb-000017
表示化学键；取代的基团V上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氟、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、咔唑基；当基团V中的取代基个数大于1时，各取代基相同或不同。
可选地，L和L 1分别独立地选自单键或如下基团所组成的组，但不仅限于此：
Figure PCTCN2021113867-appb-000018
按照本申请一种实施方式，Ar选自碳原子数为6-26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。
可选地，所述Ar中的取代基选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-20的芳基、碳原子数为12-18的杂芳基、碳原子数为5-10的环烷基；
或者，任意相邻的两个取代基形成碳原子数为5-8的饱和或不饱和环。
具体地，Ar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、环戊烷基、环乙烷基、苯基、菲基、萘基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、咔唑基、N-苯基咔唑基、环己烷基、环戊烷基、金刚烷基等。
在本申请一种实施方式中，Ar中的取代基形成环戊烷、环己烷。
按照本申请一种实施方式，Ar选自如下式i-1至式i-15所示的基团：
Figure PCTCN2021113867-appb-000019
Figure PCTCN2021113867-appb-000020
其中，M 1选自单键或者
Figure PCTCN2021113867-appb-000021
G 1～G 5和G’ 1～G’ 4各自独立地选自N、C或者C(J 1)，且G 1～G 5中至少一个选自N；当G 1～G 5中的两个以上选自C(J 1)时，任意两个J 1相同或者不相同；
G 6～G 13各自独立地选自N、C或者C(J 2)，且G 6～G 13中至少一个选自N；当G 6～G 13中的两个以上选自C(J 2)时，任意两个J 2相同或者不相同；
G 14～G 23各自独立地选自N、C或者C(J 3)，且G 14～G 23中至少一个选自N；当G 14～G 23中的两个以上选自C(J 3)时，任意两个J 3相同或者不相同；
G 24～G 33各自独立地选自N、C或者C(J 4)，且G 24～G 33中至少一个选自N；当G 24～G 33中的两个以上选自C(J 4)时，任意两个J 4相同或者不相同；
Z 1选自氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为3～10的环烷基、碳原子数为1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为18～24的三芳基硅基；
Z 2～Z 9、Z 21各自独立地选自：氢、氘、卤素基团、氰基、碳原子数为3～12的三烷基硅基、碳原子数为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1～10的烷氧基、碳原子数为1～10的烷硫基、碳原子数为1～10的烷硫基、碳原子数为3～18的杂芳基；
Z 10～Z 20、J 1～J 4各自独立地选自：氢，氘，卤素基团，氰基，碳原子数为3～12的三烷基硅基，碳原子数为1～10的烷基，碳原子数为1～10的卤代烷基，碳原子数为3～10的环烷基，碳原子数为1～10的烷氧基，碳原子数为1～10的烷硫基，任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基、甲基、乙基、叔丁基的取代基所取代的碳原子数为6～18的芳基，碳原子数为3～18的杂芳基，碳原子数为18-24的三芳基硅基；在本申请中，“任选地被0、1、2、3、4或5个独立地选自氘、氟、氯、氰基、甲基、乙基、叔丁基的取代基所取代的碳原子数为6～18的芳基”是指芳基可以被氘、氟、氯、氰基、甲基、叔丁基中的一个或多个取代，也可以不被取代，且当芳基中的取 代基的个数大于等于2时，取代基可以相同或不同。
h 1～h 21以h k表示，Z 1～Z 21以Z k表示，k为变量，表示1～21的任意整数，h k表示取代基Z k的个数；其中，当k选自5或者17时，h k选自1、2或者3；当k选自2、7、8、12、15、16、18或者21时，h k选自1、2、3或者4；当k选自1、3、4、6、9或者14时，h k选自1、2、3、4或者5；当k为13时，h k选自1、2、3、4、5或者6；当k选自10或者19时，h k选自1、2、3、4、5、6或者7；当k为20时，h k选自1、2、3、4、5、6、7或者8；当k为11时，h k选自1、2、3、4、5、6、7、8或9；且当h k大于1时，任意两个Z k相同或者不相同；
K 1选自O、S、N(Z 22)、C(Z 23Z 24)、Si(Z 28Z 29)；其中，Z 22、Z 23、Z 24、Z 28、Z 29各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 23和Z 24相互连接以与它们共同连接的原子形成碳原子数为3-15的饱和或不饱和的环，或者上述Z 28和Z 29相互连接以与它们共同连接的原子形成碳原子数为3-15的饱和或不饱和的环；
K 2选自单键、O、S、N(Z 25)、C(Z 26Z 27)、Si(Z 30Z 31)；其中，Z 25、Z 26、Z 27、Z 30、Z 31各自独立地选自：碳原子数为6～18的芳基、碳原子数为3～18的杂芳基、碳原子数为1～10的烷基或碳原子数为3～10的环烷基，或者上述Z 26和Z 27相互连接以与它们共同连接的原子形成碳原子数为3-15的饱和或不饱和的环，或者上述Z 30和Z 31相互连接以与它们共同连接的原子形成碳原子数为3-15的饱和或不饱和的环。在本申请中，所述的环指的是饱和或不饱和的环，例如
Figure PCTCN2021113867-appb-000022
Figure PCTCN2021113867-appb-000023
等，但不限于此。
可选地，Ar选自取代或未取代的基团W，所述未取代的基团W选自如下基团所组成的组：
Figure PCTCN2021113867-appb-000024
Figure PCTCN2021113867-appb-000025
其中，
Figure PCTCN2021113867-appb-000026
表示化学键；取代的基团W上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氟、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、环戊烷基、环己烷基；当基团W中的取代基个数大于1时，各取代基相同或不同。
可选地，Ar选自如下基团所组成的组，但不仅限于此：
Figure PCTCN2021113867-appb-000027
Figure PCTCN2021113867-appb-000028
可选地，所述含氮化合物选自如下化合物所组成的组，但不仅限于此：
Figure PCTCN2021113867-appb-000029
Figure PCTCN2021113867-appb-000030
Figure PCTCN2021113867-appb-000031
Figure PCTCN2021113867-appb-000032
Figure PCTCN2021113867-appb-000033
Figure PCTCN2021113867-appb-000034
Figure PCTCN2021113867-appb-000035
Figure PCTCN2021113867-appb-000036
Figure PCTCN2021113867-appb-000037
Figure PCTCN2021113867-appb-000038
Figure PCTCN2021113867-appb-000039
Figure PCTCN2021113867-appb-000040
Figure PCTCN2021113867-appb-000041
Figure PCTCN2021113867-appb-000042
Figure PCTCN2021113867-appb-000043
Figure PCTCN2021113867-appb-000044
Figure PCTCN2021113867-appb-000045
Figure PCTCN2021113867-appb-000046
本申请还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的含氮化合物。
举例而言，如图1所示，有机电致发光器件包括相对设置的阳极100和阴极200，以及设于 阳极100和阴极200之间的功能层300；功能层300包含本申请所提供的含氮化合物。
按照一种实施方式，所述有机电致发光器件例如可以为绿色有机电致发光器件。
可选地，功能层300包括有机电致发光层330，有机电致发光层330包含本申请的含氮化合物。
可选地，有机电致发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机电致发光层330由主体材料和客体材料组成，注入有机电致发光层330的空穴和注入有机电致发光层330的电子可以在有机电致发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。
有机电致发光层330的主体材料可以为金属螯合物类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，有机电致发光层330的主体材料为本申请化合物与其他化合物，如GH-P1的混合。
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，在本申请一种实施方式中，有机电致发光层330的客体材料为Ir(npy) 2acac。
在本申请的一种实施方式中，有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层321、电子阻挡层322、作为能量转化层的有机电致发光层330、电子传输层350和阴极200。本申请提供的含氮化合物可以应用于有机电致发光器件的有机电致发光层330，可以有效改善有机电致发光器件的发光效率和寿命。
可选地，阳极100包括以下阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料具体实例包括：金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO 2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。
可选地，空穴传输层321可以包括一种或者多种空穴传输材料，空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，本申请对此不做特殊的限定。举例而言，在本申请的一种实施方式中，空穴传输层321由化合物NPB组成。
可选地，电子阻挡层322包括一种或多种电子阻挡材料，电子阻挡层也称第二空穴传输性，电子阻挡材料可以选自咔唑多聚体或者其他类型化合物，本申请对此不特殊的限定。举例而言，在本申请的一些实施方式中，电子阻挡层322由TCBPA组成。
可选地，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340可以由TPyQB和LiQ组成。
可选地，阴极200包括以下阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括：金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO 2/Al、LiF/Ca、LiF/Al和BaF 2/Ca，但不限于此。优选包括包含镁和银的金属电极作为阴极。
可选地，如图1所示，在阳极100和空穴传输层321之间还可以设置有空穴注入层310， 以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。在本申请的一种实施方式中，空穴注入层310可以由HAT-CN组成。
可选地，如图1所示，在阴极200和电子传输层350之间还可以设置有电子注入层360，以增强向电子传输层350注入电子的能力。电子注入层360可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。在本申请的一种实施方式中，电子注入层360可以包括Yb(镱)。
可选地，在有机电致发光层330和电子传输层350之间还可以设置有空穴阻挡层340。
本申请实施方式还提供一种电子装置，该电子装置包括上述有机电致发光器件。由于该电子装置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。
举例而言，如图2所示，本申请提供一种电子装置400，该电子装置400包括上述有机电致发光器件。该电子装置400可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。由于该电子装置400具有上述有机电致发光器件，因此具有相同的有益效果，本申请在此不再赘述。
以下，通过实施例对本申请进一步详细说明。但是，下述实施例仅是本申请的例示，而并非限定本申请。
合成例：化合物合成
制备例1：化合物3的合成
1)中间体sub A-1的合成
通过以下合成路线合成中间体sub A-1：
Figure PCTCN2021113867-appb-000047
中间体a-I-1的合成
N 2保护下，向三口烧瓶中加入镁片(2.9g，120mmol)和四氢呋喃30mL溶液，体系温度升至80℃，向体系中加入碘(0.6g，2.4mmol)和4-溴二苯并呋喃(30.0g，120mmol)在30mL的THF溶液中完全溶解形成的混合物，30min内慢慢向体系中进行滴加，滴加过程中控制温度在80℃。滴加完毕，在80℃温度条件下搅拌反应2h。常温冷却后将溶解在80mL的THF的2,4,6-三氯-1,3,5-三嗪(22.3g，120mmol)滴加到混合溶液中，搅拌3h后结束反应。反应结束后，加入甲苯和水进行萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，减压蒸馏进行浓缩；粗品利用硅胶柱色谱进行提纯，甲醇重结晶过滤得到固体中间体a-I-1(24.2g，63％)。
中间体sub A-1的合成
N 2保护下，向三口烧瓶中加入镁片(1.52g，63.7mmol)和四氢呋喃30mL溶液，体系温度升至80℃，向体系中加入碘(0.32g，1.26mmol)和4-溴二苯并呋喃((15.73g，63.7mmol)在30mL的THF溶液中完全溶解形成的混合物，30min内慢慢向体系中进行滴加，滴加过程中控制温度在80℃。滴加完毕，在80℃温度条件下搅拌反应2h。常温冷却后将溶解在40mL的THF的中间体a-I-1(20.13g，63.7mmol)滴加到混合溶液中，搅拌3h后结束反应。反应结束后，加入 甲苯和水进行萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，减压蒸馏进行浓缩；粗品利用硅胶柱色谱进行提纯，甲醇重结晶过滤得到固体中间体sub A-1(22.5g，79％)。
2)中间体sub B-1合成
通过以下合成路线合成中间体sub B-1：
Figure PCTCN2021113867-appb-000048
将4-溴菲(50.0g，194.4mmol)、联硼酸频那醇酯(74.1g，291.6mmol)、三(二亚苄基丙酮)二钯(1.7g，1.9mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(1.8g，3.8mmol)、1,4-二氧六环(500mL)加入圆底烧瓶中，氮气保护下升温至100℃，加热回流搅拌12h。反应结束后，溶液冷却至室温，加入甲苯和水进行萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩，用正庚烷打浆得到固体化合物中间体sub B-1(23.6g，40％)。
3)化合物3的制备
Figure PCTCN2021113867-appb-000049
将中间体sub A-1(10.0g，22.3mmol)、中间体sub B-1(7.1g，23.4mmol)、四(三苯基膦)钯(0.5g，0.4mmol)、碳酸钾(6.2g，44.6mmol)、四丁基溴化铵(0.1g，0.4mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌8h。反应结束后，溶液冷却至室温，加入甲苯和水进行萃取反应溶液，合并有机相，无水硫酸镁干燥有机层，过滤，进行浓缩；粗品利用硅胶柱色谱进行提纯，得到固体化合物3(7.7g，59％)。m/z＝590.18[M+H] +。
制备例2-10：化合物1、27、149、124、374、266、17、65、31的合成
参照中间体sub A-1合成方法，制备表1所示的中间体sub A-2到sub A-17，不同之处在于使用表1中的原料A替代制备中间体a-I-1中的原料4-溴二苯并呋喃，使用表1中原料B替代制备中间体sub A-1中的原料4-溴二苯并呋喃。
表1
Figure PCTCN2021113867-appb-000050
Figure PCTCN2021113867-appb-000051
Figure PCTCN2021113867-appb-000052
以与制备例1相似的方法合成下表2中所示的化合物，不同之处在于使用表2中的中间体sub A-2～sub A-10替代中间体sub A-1。
表2
Figure PCTCN2021113867-appb-000053
Figure PCTCN2021113867-appb-000054
制备例11：化合物256的合成
通过以下合成路线合成化合物256：
Figure PCTCN2021113867-appb-000055
1)中间体sub A-I-1的合成
将中间体sub A-1(30.0g，66.9mmol)、3-氯苯硼酸(11.5g，73.6mmol)、四(三苯基膦)钯(1.5g，1.3mmol)、碳酸钾(18.5g，133.9mmol)、四丁基溴化铵(0.2g，0.6mmol)、甲苯(240mL)、乙醇(60mL)和去离子水(60mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌8h。反应结束后，溶液冷却至室温，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；粗品利用硅胶柱色谱进行提纯，得到固体化合物中间体sub A-I-1(22.8g，65％)。
2)中间体sub A-II-1的合成
将中间体sub A-I-1(20.g，38.1mmol)，联硼酸频哪醇酯(14.5g，57.2mmol)、三(二亚苄基丙酮)二钯(0.3g，0.4mmol)、2-二环己基磷-2',4',6'-三异丙基联苯(0.4g，0.7mmol)，醋酸钾(7.5g，76.3mmol)，加入1,4-二氧六环(200mL)在100℃温度条件下回流反应12h。当反应结束时，使用二氯甲烷和水进行提取。利用硫酸镁来干燥和浓缩有机层，对所生成的化合物用乙醇打浆2次，获得中间体sub A-II-1(16.2g，69％)。
3)化合物256的合成
将中间体sub A-II-1(15.8g，25.6mmol)、4-溴菲(6.0g，23.3mmol)、四(三苯基膦)钯(0.5g，0.5mmol)、碳酸钾(6.4g，46.6mmol)、四丁基溴化铵(0.07g，0.2mmol)、甲苯(120mL)、乙醇(30mL)和去离子水(30mL)加入三口烧瓶中，氮气保护下升温至76℃，加热回流搅拌13h。反应结束后，溶液冷却至室温，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；粗品利用硅胶柱色谱进行提纯，得到固体化合物256(9.2g，59％)。MS[M+H]+＝666.21。
制备例12-24：化合物294、366、389、398、399、245、230、270、392、400、401、402、403的合成
以与制备例11类似的方法合成下表3中所示化合物，不同之处在于使用表3中原料C替代制备中间体sub A-I-1中的3-氯苯硼酸，使用表3中的中间体sub A替代中间体sub A-1。
表3
Figure PCTCN2021113867-appb-000056
Figure PCTCN2021113867-appb-000057
Figure PCTCN2021113867-appb-000058
部分化合物核磁数据如下表4所示：
表4
Figure PCTCN2021113867-appb-000059
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110nm的ITO基板切割成40mm(长)×40mm(宽)×0.7mm(厚)的尺寸，采用光刻工序，将其制备成具有阳极、阴极搭接区域以及绝缘层图案的实验基板，并可利用紫外臭氧等等离子对基板进行表面处理，以增加阳极的功函数。也可采用有机溶剂清洗ITO基板表面，以清除其表面的杂质及油污。
在ITO基板上真空蒸镀一层HAT-CN以形成厚度为10nm的空穴注入层(HIL)，并且在空穴注入层上真空蒸镀NPB，以形成厚度为110nm的空穴传输层。
在空穴传输层上真空蒸镀TCBPA，形成厚度为35nm的电子阻挡层。
在电子阻挡层上，将化合物3与GH-P1作为主体，Ir(npy) 2acac作为掺杂剂，按照50％：45％：5％的质量比进行共同蒸镀，形成厚度为38nm的绿色有机电致发光层(EML)。
将TPyQB和LiQ以1:1的重量比进行混合并蒸镀形成28nm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1.5nm的电子注入层(EIL)。
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14nm的阴极。
此外，在上述阴极上真空蒸镀厚度为66nm的CP-1，从而完成有机电致发光器件的制造。
实施例2～实施例24
除了在形成有机电致发光层时，以表4中所示的化合物替代实施例1中的化合物3以外，利用与实施例1相同的方法制作有机电致发光器件。
比较例1～比较例6
除了在形成有机电致发光层时，以化合物A、B、C、D、E、F替代实施例1中的化合物3以外，利用与实施例1相同的方法制作有机电致发光器件。
其中，在制备有机电致发光器件时，比较例1～6与实施例1～24所使用的材料结构如下：
Figure PCTCN2021113867-appb-000060
Figure PCTCN2021113867-appb-000061
对实施例1～24和比较例1～6制备所得的绿色有机电致发光器件进行性能测试，具体在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，测试结果展示在表5中。
表5
Figure PCTCN2021113867-appb-000062
如表5中的器件性能测试结果可知，实施例1-24将本申请化合物用作N型绿色有机电致发光层主体材料，与比较例1-6相比，在色坐标相差不大的情况下，发光效率Cd/A至少提高了18.5％，外量子效率至少提高了42.5％，寿命T95至少提高了12.7％。
因此，本申请的含氮化合物用于制备绿色有机电致发光器件时，可以有效地延长有机电致发光器件的寿命，大幅提升有机电致发光器件的发光效率。
以上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 (10)

  1. 一种含氮化合物，其特征在于，所述含氮化合物的结构如式1所示：
    Figure PCTCN2021113867-appb-100001
    其中，X 1选自O或S；
    X 2、X 3、X 4和X 5彼此相同或不同，且各自独立地选自C(H)或N；
    L和L 1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、碳原子数为1-20的取代或未取代的烷基、碳原子数为3-20的取代或未取代的环烷基；
    L、L 1和Ar中的各取代基彼此相同或不同，且各自独立地选自氘，卤素基团，氰基，碳原子数为3-20的杂芳基，任选地被0、1、2、3、4或5个独立地选自氘、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L、L 1和Ar中，任选地，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，L和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、碳原子数为5-20的亚取代或未取代的亚杂芳基；
    优选地，所述L和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、碳原子数为5-12的杂芳基。
  3. 根据权利要求1所述的含氮化合物，其特征在于，L和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、取代或未取亚吡啶基、取代或未取代的亚喹啉基、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、取代或未取代的亚菲基、取代或未取代的亚蒽基、取代或未取代的N-苯基咔唑亚基；
    或者，上述任意两个基团通过单键连接所形成的基团；
    优选地，所述L和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、萘基、联苯基、咔唑基。
  4. 根据权利要求1所述的含氮化合物，其特征在于，L和L 1分别独立地选自单键、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 PCTCN2021113867-appb-100002
    Figure PCTCN2021113867-appb-100003
    其中，
    Figure PCTCN2021113867-appb-100004
    表示化学键；取代的基团V上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氟、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、咔唑基；当基团V中的取代基个数大于1时，各取代基相同或不同。
  5. 根据权利要求1所述的含氮化合物，其特征在于，Ar选自碳原子数为6-26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；
    优选地，所述Ar中的取代基选自氘、氟、氰基、碳原子数为1-5的烷基、碳原子数为6-20的芳基、碳原子数为12-18的杂芳基、碳原子数为5-10的环烷基；
    或者，任意相邻的两个取代基形成碳原子数为5-8的饱和或不饱和环。
  6. 根据权利要求1所述的含氮化合物，Ar选自取代或未取代的基团W，所述未取代的基团W选自如下基团所组成的组：
    Figure PCTCN2021113867-appb-100005
    其中，
    Figure PCTCN2021113867-appb-100006
    表示化学键；取代的基团W上具有一个或多个的取代基，所述取代基各自独立地选自：氘、氟、氰基、卤素基团、甲基、乙基、正丙基、异丙基、叔丁基、苯基、萘基、联苯基、环戊烷基、环己烷基；当基团W中的取代基个数大于1时，各取代基相同或不同。
  7. 根据权利要求1所述的含氮化合物，其特征在于，所述含氮化合物选自如下化合物所组成的组：
    Figure PCTCN2021113867-appb-100007
    Figure PCTCN2021113867-appb-100008
    Figure PCTCN2021113867-appb-100009
    Figure PCTCN2021113867-appb-100010
    Figure PCTCN2021113867-appb-100011
    Figure PCTCN2021113867-appb-100012
    Figure PCTCN2021113867-appb-100013
    Figure PCTCN2021113867-appb-100014
    Figure PCTCN2021113867-appb-100015
    Figure PCTCN2021113867-appb-100016
    Figure PCTCN2021113867-appb-100017
    Figure PCTCN2021113867-appb-100018
    Figure PCTCN2021113867-appb-100019
    Figure PCTCN2021113867-appb-100020
    Figure PCTCN2021113867-appb-100021
    Figure PCTCN2021113867-appb-100022
    Figure PCTCN2021113867-appb-100023
    Figure PCTCN2021113867-appb-100024
  8. 一种有机电致发光器件，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1-7任一项所述的含氮化合物；
    优选地，所述功能层包括有机电致发光层，所述有机电致发光层包含所述的含氮化合物。
  9. 根据权利要求8所述的有机电致发光器件，其特征在于，所述有机电致发光层包含主体材料，所述主体材料含有所述的含氮化合物。
  10. 一种电子装置，其特征在于，包括权利要求8或9所述的有机电致发光器件。
PCT/CN2021/113867 2020-11-10 2021-08-20 含氮化合物、有机电致发光器件和电子装置 WO2022100194A1 (zh)

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