CN112209840A - Nitrogen-containing compound, electronic component, and electronic device - Google Patents

Nitrogen-containing compound, electronic component, and electronic device Download PDF

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Publication number
CN112209840A
CN112209840A CN202010990078.8A CN202010990078A CN112209840A CN 112209840 A CN112209840 A CN 112209840A CN 202010990078 A CN202010990078 A CN 202010990078A CN 112209840 A CN112209840 A CN 112209840A
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carbon atoms
group
independently selected
nitrogen
ring
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CN112209840B (en
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岳富民
马天天
南朋
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic light-emitting materials, and provides a nitrogen-containing compound, an electronic element and an electronic device. The nitrogen-containing compound has a structural formula shown in formula 1, wherein ring A and ring B are respectively and independently selected from benzene rings or condensed aromatic rings with ring-forming carbon atoms of 10-14, and at least one of ring A and ring B is selected from the condensed aromatic rings. The nitrogen-containing compound can improve the performance of an electronic component.
Figure DDA0002690561110000011

Description

Nitrogen-containing compound, electronic component, and electronic device
Technical Field
The present disclosure relates to organic light emitting materials, and particularly to a nitrogen-containing compound, an electronic device and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the application range of electronic elements for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic element is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the organic light emitting layer under the action of the electric field, holes on the anode side also move to the organic light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
In the prior art, some new electroluminescent materials are described in patent documents such as KR1020190035567A, CN106008424A, WO2020032574a1, etc. However, there is still a need to develop new materials to further improve the performance of electronic components.
The above information disclosed in the background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
An object of the present application is to provide a nitrogen-containing compound, an electronic component, and an electronic device, which improve the performance of the electronic component.
In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:
according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structural formula as shown in formula 1:
Figure BDA0002690561090000011
wherein, the ring A and the ring B are respectively and independently selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms, and at least one of the ring A and the ring B is selected from the condensed aromatic ring;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms;
Q1and Q2The same or different, each independently selected from a halogen group, a cyano group, a halogenated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a heteroaryl group having 4 to 12 carbon atoms, and a heteroaralkyl group having 5 to 13 carbon atoms; n represents Q1The number of (3) is 0 or 1; m represents Q2The number of (3) is 0 or 1;
Ar1and Ar2The same or different, each is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 4-30 carbon atoms;
Ar1、Ar2and the substituents in L are the same or different and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 1 to 10 carbon atomsAlkylthio group, trialkyl silicon group with 3-12 carbon atoms; at Ar1、Ar2And L, when two substituents are present on the same atom, optionally, the two substituents are linked to each other to form a 5-to 18-membered saturated or unsaturated ring together with the atom to which they are linked.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, an electronic device is provided, which includes the above electronic element.
In the nitrogen-containing compound provided by the present application, it can be seen from formula 1 that the large condensed ring structure at least includes a fluorenyl group and at least one aromatic ring condensed with the fluorenyl group, and the large condensed ring structure has stronger conjugation compared to the fluorenyl group, and can be used as a core group of the nitrogen-containing compound to improve the hole transport capability of the nitrogen-containing compound. Moreover, the large condensed ring system is combined with the adamantyl group rich in the electron group, so that the electron density of the large condensed ring system can be further improved through a super-conjugation effect, and further the hole migration capability of the nitrogen-containing compound is further improved. The adamantyl has larger steric hindrance, so that the adamantyl can reduce the intermolecular stacking effect of a triarylamine structure and the molecular symmetry of the nitrogen-containing compound, thereby improving the form of the nitrogen-containing compound during film formation, increasing the glass transition temperature and the evaporation temperature of the nitrogen-containing compound, controlling the crystallinity of the nitrogen-containing compound, enabling the nitrogen-containing compound to have good physical and thermal stability, further improving the stability and the mass production uniformity of an electronic element, and prolonging the service life of the electronic element containing the nitrogen-containing compound. Moreover, the adamantyl group with large steric hindrance is positioned among three aromatic branches of the triarylamine, so that the bonding included angle and the conjugation degree among the aromatic branches can be adjusted, and the HOMO energy level of the nitrogen-containing compound is further adjusted, so that the nitrogen-containing compound has better hole migration capability. In this way, when the nitrogen-containing compound is used for an electronic element that realizes photoelectric conversion or electroluminescence, for example, as a hole transport layer, the performance of the electronic element can be improved, and for example, the light emission efficiency and the device life of an organic electroluminescent device can be improved.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic second device according to an embodiment of the present application.
The reference numerals of the main elements in the figures are explained as follows:
100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure 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 to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
In a first aspect, the present application provides a nitrogen-containing compound having a structural formula as shown in formula 1:
Figure BDA0002690561090000031
wherein, the ring A and the ring B are respectively and independently selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms, and at least one of the ring A and the ring B is selected from the condensed aromatic ring;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms;
Q1and Q2The same or different, each independently selected from a halogen group, a cyano group, a halogenated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a heteroaryl group having 4 to 12 carbon atoms, and a heteroaralkyl group having 5 to 13 carbon atoms; n represents Q1The number of (3) is 0 or 1; m represents Q2The number of (3) is 0 or 1;
Ar1and Ar2The same or different, each is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 4-30 carbon atoms;
Ar1、Ar2and the substituents in L are the same or different and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms; at Ar1、Ar2And in L, when two substituents are present on the same atom, optionally, two substituents are presentThe substituents are linked to each other to form, together with the atoms to which they are commonly attached, a 5-to 18-membered saturated or unsaturated ring. The expression "optionally, two substituents are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 18-membered saturated or unsaturated ring" means that the two substituents may be present individually or may be linked to form, together with the atoms to which they are commonly linked, the above-mentioned ring structure.
In this application, ring A refers to
Figure BDA0002690561090000032
It is selected from benzene rings or fused aromatic rings, which may be selected from naphthalene rings, anthracene rings, phenanthrene rings, and the like, for example. Correspondingly, ring B means
Figure BDA0002690561090000033
It is selected from benzene rings or fused aromatic rings, which may be selected from naphthalene rings, anthracene rings, phenanthrene rings, and the like, for example. For example, in the compounds
Figure BDA0002690561090000034
Wherein ring A is a benzene ring, ring B is a naphthalene ring, and substituent group Q on ring A1Is methyl, and L connecting the nitrogen atom with the ring B is a single bond.
It is to be understood that each of the rings a and B includes at least one benzene ring structure, and the two benzene ring structures are connected to the adamantyl group to form a structure in which the fluorenyl group is spiro-connected to the adamantyl group. At least one of the ring A and the ring B is a condensed aromatic ring, so that the fluorenyl is condensed with at least other aromatic rings to form a large condensed ring structure. Wherein the content of the first and second substances,
Figure BDA0002690561090000041
represents a chemical bond.
In the nitrogen-containing compound provided by the present application, it can be seen from formula 1 that the large condensed ring structure at least includes a fluorenyl group and at least one aromatic ring condensed with the fluorenyl group, and the large condensed ring structure has stronger conjugation compared to the fluorenyl group, and can be used as a core group of the nitrogen-containing compound to improve the hole transport capability of the nitrogen-containing compound. Moreover, the large condensed ring system is combined with the adamantyl group rich in the electron group, so that the electron density of the large condensed ring system can be further improved through a super-conjugation effect, and further the hole migration capability of the nitrogen-containing compound is further improved. The adamantyl has larger steric hindrance, so that the adamantyl can reduce the intermolecular stacking effect of a triarylamine structure and the molecular symmetry of the nitrogen-containing compound, thereby improving the form of the nitrogen-containing compound during film formation, increasing the glass transition temperature and the evaporation temperature of the nitrogen-containing compound, controlling the crystallinity of the nitrogen-containing compound, enabling the nitrogen-containing compound to have good physical and thermal stability, further improving the stability and the mass production uniformity of an electronic element, and prolonging the service life of the electronic element containing the nitrogen-containing compound. Moreover, the adamantyl group with large steric hindrance is positioned among three aromatic branches of the triarylamine, so that the bonding included angle and the conjugation degree among the aromatic branches can be adjusted, and the HOMO energy level of the nitrogen-containing compound is further adjusted, so that the nitrogen-containing compound has better hole migration capability. In this way, when the nitrogen-containing compound is used as a hole transport layer in an electronic element for realizing photoelectric conversion or electroluminescence, the performance of the electronic element can be improved, and for example, the light-emitting efficiency and the device life of an organic electroluminescent device can be improved.
In this application L, Ar1And Ar2The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L is selected from substituted arylene having 7 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 7. For another example, if L is 3-cyano-1, 5-phenylene, then L is a substituted arylene group having 7 carbon atoms.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated by a carbon-carbon bond may also be considered as aromatic groups of the present applicationAnd (4) a base. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. In the present application, the biphenyl group and the terphenyl group are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
Figure BDA0002690561090000042
and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom. The fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure, and specific examples of the substituted fluorenyl group include, but are not limited to, the following structures:
Figure BDA0002690561090000043
in the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, carbazole-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary 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, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
Figure BDA0002690561090000051
It means that one end of the connecting key can be connected to the through part of the keyThe other end of the ring system is connected with the rest of the compound molecule at any position in the penetrated ring system.
For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).
Figure BDA0002690561090000052
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
Figure BDA0002690561090000053
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
Figure BDA0002690561090000054
Figure BDA0002690561090000061
In the present application, a cycloalkyl group having 3 to 10 carbon atoms may be used as a substituent for the aryl group or the heteroaryl group, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. The alkyl group having 1 to 7 carbon atoms may have 1,2, 3,4, 5, 6 or 7 carbon atoms.
In this application, halogen includes fluorine, chlorine, bromine, iodine.
In the present application, the alkoxy group having 1 to 10 carbon atoms may have, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10 carbon atoms, and specific examples of the alkoxy group having 1 to 10 carbon atoms include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, and the like.
In the present application, the substituents may be aryl groups having 6 to 18 carbon atoms and aryl groups having 6 to 20 carbon atoms, each of which has 6 (e.g., phenyl), 10 (e.g., naphthalene), 12 (e.g., biphenyl), 14, 18, or the like. Specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, phenanthryl, 9-dimethylfluorenyl and the like.
In the present application, the number of carbon atoms of the heteroaryl group as a substituent may be 3 to 18, and for example, may be 3,4, 5, 7, 8, 9, 12, 18, or the like. Specific examples of heteroaryl as a substituent include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
Alternatively,
Figure BDA0002690561090000062
selected from the group consisting of the structures shown below:
Figure BDA0002690561090000063
in a further alternative,
Figure BDA0002690561090000064
wherein n is 1 and
Figure BDA0002690561090000065
selected from the group consisting of the structures shown below:
Figure BDA0002690561090000071
in the context of the present application, it is,
Figure BDA0002690561090000072
represents a chemical bond; it shows the above structure for use in combination with
Figure BDA0002690561090000073
With the above structure for connection with
Figure BDA0002690561090000074
And (4) connecting. For example, in the compounds
Figure BDA0002690561090000075
In (1),
Figure BDA0002690561090000076
is composed of
Figure BDA0002690561090000077
And n is 0.
Alternatively,
Figure BDA0002690561090000078
selected from the group consisting of the structures shown below:
Figure BDA0002690561090000079
Figure BDA0002690561090000081
in a further alternative,
Figure BDA0002690561090000082
selected from the group consisting of the structures shown below:
Figure BDA0002690561090000083
in the context of the present application, it is,
Figure BDA0002690561090000084
represents a chemical bond; # denotes the above structure for use with
Figure BDA0002690561090000085
Connection, # # denotes the above structure for
Figure BDA0002690561090000086
And (4) connecting. For example, in the compounds
Figure BDA0002690561090000087
In (1),
Figure BDA0002690561090000088
is composed of
Figure BDA0002690561090000089
Wherein L is a single bond, Ar1And Ar2Are both biphenyl groups, and m ═ 0.
In some embodiments of the present application, the nitrogen-containing compound has a structure as shown in formula 1-1 to formula 1-37:
Figure BDA0002690561090000091
Figure BDA0002690561090000101
in bookIn application, optionally, Q1And Q2Each independently selected from fluorine, cyano, fluoroalkyl having 1 to 4 carbon atoms, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms and aryl having 6 to 12 carbon atoms. According to an exemplary embodiment, Q1And Q2Each independently selected from deuterium, methyl, phenyl, cyano, trifluoromethyl, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trimethylsilyl, methoxy, pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl, naphthyl.
In the application, L is selected from single bond, substituted or unsubstituted arylene with 6-26 carbon atoms and substituted or unsubstituted heteroarylene with 5-25 carbon atoms. For example, L may be a single bond, and may be selected from a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 8, 9, 12, 16, 18, 20, 21, 22, 24, 25 carbon atoms.
Alternatively, L is selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 5 to 24 carbon atoms.
Alternatively, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted dihydroanthracenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzop-dioxin group, and the like.
Alternatively, the substituents in L are each independently selected from: deuterium, a halogen group (e.g., fluorine), a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms (e.g., trifluoromethyl), a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.
According to one embodiment, L is selected from the group consisting of groups represented by formula j-1 through formula j-15:
Figure BDA0002690561090000111
wherein M is2Selected from a single bond or
Figure BDA0002690561090000112
D1～D5Each independently selected from N or C (F)5) And D is1～D5At least one is selected from N; when D is present1～D5Two or more of C (F)5) When, two arbitrary F5The same or different;
D6～D13each independently selected from N or C (F)6) And D is6～D13At least one is selected from N; when D is present6～D13Two or more of C (F)6) When, two arbitrary F6The same or different;
D14～D23each independently selected from N or C (F)7) And D is14～D23At least one is selected from N; when D is present14～D23Two or more of C (F)7) When, two arbitrary F7The same or different;
D24～D33each independently selected from N or C (F)8) And D is24～D33At least one is selected from N; when D is present24～D33Two or more of C (F)8) When, two arbitrary F8Is the same or differentThe same;
E1～E19、F5～F8each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-18 carbon atoms, aryl with 6-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms and alkylthio with 1-10 carbon atoms;
e1～e19with erIs represented by1～E19With ErR is a variable and is an arbitrary integer of 1 to 19, erRepresents a substituent ErThe number of (2); when r is 17, erSelected from 1,2 or 3; when r is selected from 1,2, 3,4, 5, 6, 9, 13, 14, 18 or 19, erSelected from 1,2, 3 or 4; when r is selected from 15 or 16, erSelected from 1,2, 3,4 or 5; when r is selected from 7 or 11, erSelected from 1,2, 3,4, 5 or 6; when r is 12, erSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different;
K3selected from O, S, Se, N (E)20)、C(E21E22)、Si(E21E22) (ii) a Wherein E is20、E21、E22Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or E21And E22Are linked to each other to form, together with the atoms to which they are commonly linked, a saturated or unsaturated 5-to 18-membered ring;
K4selected from the group consisting of a single bond, O, S, Se, N (E)23)、C(E24E25)、Si(E24E25) (ii) a Wherein E is23、E24、E25Each independently selected from: aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atomsIs an alkyl group of 1 to 10, a cycloalkyl group having 3 to 10 carbon atoms, or E24And E25Are linked to form, together with the atoms to which they are commonly attached, a 5-to 18-membered saturated or unsaturated ring.
In this application, E is as defined above21And E22The above-mentioned E24And E25In both groups, the ring formed by the interconnection of the two groups in each group is a 5-13 membered saturated or unsaturated ring. For example, in the formula j-8, when K is4And M2Are all single bonds, E11Is hydrogen, e11＝6，K3Is C (E)21E22)，E24And E25When linked to each other to form a 5-membered saturated ring with the atoms to which they are commonly attached, formula j-8 may be
Figure BDA0002690561090000121
Likewise, the formula j-8 may be
Figure BDA0002690561090000122
I.e. E21And E22Are linked to each other to form, together with the atoms to which they are commonly linked, a 13-membered unsaturated ring, a 14-membered unsaturated ring, respectively.
Alternatively, L is selected from a single bond, an unsubstituted group V or a substituted group V, wherein the unsubstituted group V is selected from the group consisting of:
Figure BDA0002690561090000123
wherein, V1Is selected from C (R)7R8)、N(R9)、O、S、Se、Si(R7R8)，V2Selected from single bond, C (R)10R11)、N(R12)、O、S、Se、Si(R10R11)；R7、R8、R9、R10、R11、R12Each independently selected from: an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, or R7And R8Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 13-membered saturated or unsaturated ring, or R as defined above10And R11Are linked to each other to form, together with the atoms to which they are commonly linked, a saturated or unsaturated ring having 5 to 13 carbon atoms;
the substituted group V has one or more than two substituent groups, the substituent groups are selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, phenyl, trimethylsilyl, phenyl and cyclohexyl, and when the number of the substituent groups on the substituted group V is more than two, any two substituent groups are the same or different.
Further optionally, L is selected from a single bond or a group consisting of:
Figure BDA0002690561090000131
in this application, optionally, Ar1And Ar2Each independently selected from a substituted or unsubstituted aryl group having 6 to 33 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 26 carbon atoms. For example, Ar1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 24, 25, 26, 28, 29, 30, 31, 32, 33 carbon atoms or substituted or unsubstituted heteroaryl groups having 5, 8, 9, 12, 14, 16, 18, 20, 21, 22, 24, 25, 26 carbon atoms.
Further optionally, Ar1And Ar2Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms.
Alternatively, Ar1And the substituents in Ar are independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a carbon atomA trialkylsilyl group with a numerator of 3-7.
According to one embodiment, Ar1And Ar2Each independently selected from the group consisting of formula i-1 through formula i-17:
Figure BDA0002690561090000141
wherein M is1Selected from a single bond or
Figure BDA0002690561090000142
Each ring C and D is a naphthalene ring;
G1～G5each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H1selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3-12 carbon atoms, alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, and haloalkyl having 3-10 carbon atomsA cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkylthio group having 1 to 10 carbon atoms;
H2～H9、H21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
H10～H20and H22～H23、F1～F4Each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
h1～h23by hkIs represented by H1～H23With HkK is a variable and represents an arbitrary integer of 1 to 23, hkRepresents a substituent HkThe number of (2); wherein, when k is selected from 5 or 17, hkSelected from 0, 1,2 or 3; when k is selected from 2,7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 23, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11 or 22, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; when k is 23, hkSelected from 1,2, 3,4, 5, 6, 7, 8, 9,10 or 11; and when h iskWhen greater than 1, any two HkThe same or different;
K1selected from O, S, Se, N (H)24)、C(H25H26)、Si(H25H26) (ii) a Wherein H24、H25、H26Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H25And H26Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 13-membered saturated or unsaturated ring;
K2selected from single bond, O, S, Se, N (H)27)、C(H28H29)、Si(H28H29) (ii) a Wherein H27、H28、H29Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H28And H29Are linked to form, together with the atoms to which they are commonly attached, a 5-to 18-membered saturated or unsaturated ring.
In the present application, the above-mentioned H25And H26H above28And H29In the two groups, the ring formed by connecting the two groups in each group is a 5-18-membered saturated or unsaturated ring. According to one embodiment, H25And H26H above28And H29The two groups can form 5-15 saturated or unsaturated rings respectively.
Alternatively, Ar1And Ar2Each independently selected from a substituted or unsubstituted group T, wherein the unsubstituted group T is selected from the group consisting of:
Figure BDA0002690561090000151
Figure BDA0002690561090000161
wherein, V3Is selected from C (R)1R2)、N(R3)、O、S、Se、Si(R1R2)，V4Is selected fromBond, C (R)4R5)、N(R6)、O、S、Se、Si(R4R5)；R1、R2、R3、R4、R5、R6Each independently selected from: an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, or R1And R2Are linked to each other to form a 5-to 10-membered saturated ring together with the atoms to which they are commonly linked, or the above R4And R5Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 10-membered saturated ring;
the substituted group T has one or more substituents independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trimethylsilyl, pyridyl and cyclohexyl, and when the number of the substituents on the substituted group T is more than two, any two substituents are the same or different.
According to one embodiment, Ar1And Ar2Each independently selected from:
Figure BDA0002690561090000162
Figure BDA0002690561090000171
Figure BDA0002690561090000181
in some embodiments, L is a single bond, Ar1And Ar2Not phenyl at the same time. Optionally, the nitrogen-containing compound is selected from the group consisting of:
Figure BDA0002690561090000182
Figure BDA0002690561090000191
Figure BDA0002690561090000201
Figure BDA0002690561090000211
Figure BDA0002690561090000221
Figure BDA0002690561090000231
Figure BDA0002690561090000241
Figure BDA0002690561090000251
Figure BDA0002690561090000261
Figure BDA0002690561090000271
Figure BDA0002690561090000281
Figure BDA0002690561090000291
Figure BDA0002690561090000301
Figure BDA0002690561090000311
Figure BDA0002690561090000321
Figure BDA0002690561090000331
Figure BDA0002690561090000341
the synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present invention illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the present application.
In a second aspect, the present application further provides an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
The nitrogen-containing compounds provided herein can be used to form at least one organic film layer in a functional layer to improve efficiency and lifetime characteristics of electronic components.
Optionally, an organic film layer containing a nitrogen-containing compound of the present application is positioned between the anode and the energy conversion layer of the electronic component in order to improve the transport of holes between the anode and the energy conversion layer.
Optionally, the functional layer comprises a hole transport layer comprising a nitrogen-containing compound as provided herein. The hole transport layer may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
According to one embodiment, the hole transport layer includes a first hole transport layer and a second hole transport layer which are stacked, and the first hole transport layer is closer to the surface of the anode than the second hole transport layer; the first hole transport layer and/or the second hole transport layer comprise a nitrogen-containing compound provided herein. In other words, either one of the first hole transporting layer and the second hole transporting layer may contain the nitrogen-containing compound provided herein, or both of the first hole transporting layer and the second hole transporting layer may contain the nitrogen-containing compound provided herein. It is to be understood that the first hole transport layer and the second hole transport layer may or may not contain other materials.
According to a specific embodiment, as shown in fig. 1, the electronic component may be an organic electroluminescent device. The organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
In the present application, the anode 100 includes an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline. Preferably comprises oxygenIndium Tin Oxide (ITO) is used as a transparent electrode of the anode.
According to a specific embodiment, the nitrogen-containing compound provided by the present application can be applied to the second hole transport layer 322 of the organic electroluminescent device to improve the lifetime and luminous efficiency of the organic electroluminescent device.
Alternatively, the first hole transport layer 321 includes one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. For example, the first hole transport layer 321 may be composed of a compound NPB.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. In one embodiment, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be CBP.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq)2(acac) and the like.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of TPBi and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of HAT-CN.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.
According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises a nitrogen-containing compound as provided herein.
According to an exemplary embodiment, as shown in fig. 3, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application. The hole transport layer 320 may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
Optionally, the hole transport layer 320 may further include an inorganic doping material to improve the hole transport property of the hole transport layer 320.
According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer contains the nitrogen-containing compound of the present application.
In a third aspect, the present application further provides an electronic device including the electronic component according to the second aspect.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.
In the following, several specific embodiments are exemplarily provided to further explain and illustrate the present application. However, the following examples are merely illustrative of the present application and do not limit the present application.
Example 1: preparation of Compound 1
Step (1)
Figure BDA0002690561090000361
Under the protection of nitrogen, adding 2-bromo-4-chloroiodobenzene (53.98g, 170.11mmol), 2-naphthalene boric acid (30.00g, 154.644mmol), toluene (240mL), ethanol (120mL), water (60mL), potassium carbonate (42.68g, 309.29mmol), stirring, heating to 55 ℃, rapidly adding tetrakis (triphenylphosphine) palladium (3.57g, 3.09mmol) and tetrabutylammonium bromide (TBAB) (2.14g,7.73mmol), then continuously heating to 70-75 ℃, refluxing for 18h, after the reaction is finished, naturally cooling to room temperature (20-35 ℃), extracting with dichloromethane, washing the organic phase with water, drying the organic phase, filtering, and concentrating the organic phase to obtain a crude product. The crude product was recrystallized with a mixed solvent of dichloromethane and n-heptane to a LC purity of > 98%. Drying to obtain white solid intermediate I-A-1(45.48g, yield 85%).
Step (2)
Figure BDA0002690561090000362
42.4g (133.5mmol) of intermediate I-A-1 and 420mL of dried tetrahydrofuran are added into a 1000mL three-neck flask, the temperature is reduced to below minus 80 ℃ under stirring, 70.1mL of n-butyllithium (140.2mmol) n-hexane solution with the concentration of 2mol/L is slowly dropped under the protection of nitrogen, the temperature is kept for 30min after dropping, then a mixed solution consisting of 150.1g (140.2mmol) of adamantanone and 200mL of tetrahydrofuran is added, the temperature is kept for 30min, the mixture is naturally raised to the room temperature and is continuously stirred for 2 h, water quenching reaction is dropped, ethyl acetate is used for extracting reaction liquid, an organic phase is dried by magnesium sulfate and then is distilled under reduced pressure, and the obtained solid crude product is recrystallized by using a mixed solvent of dichloromethane and n-heptane (the volume ratio is 1: 5) to obtain intermediate I-A-2(39.46g, the yield is 76%).
Step (3)
Figure BDA0002690561090000363
36.5g of intermediate I-A-2(93.84mmol) and 360mL of acetic acid were put into a 500mL three-necked flask, 36mL of concentrated sulfuric acid (98 wt%) was slowly added dropwise with stirring, heating was started to 80 ℃ to react for 8 hours, the reaction solution was extracted with ethyl acetate, the mixture was separated, the organic phase was dried over magnesium sulfate and distilled under reduced pressure, and the crude product was recrystallized from a mixed solvent of ethyl acetate and n-heptane (volume ratio 1:3) to give intermediate I-A (22.17g, yield 63.7%).
Step (4)
Figure BDA0002690561090000371
Adding the intermediate I-A (14.0g,37.74mmol), 4-aminobiphenyl (8.97g,38.5mmol), tris (dibenzylideneacetone) dipalladium (0.35g,0.38mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.36g,0.75mmol) and sodium tert-butoxide (10.88g,113.23mmol) into toluene (140mL), heating to 108 ℃ under nitrogen protection, and stirring for 3 h; cooling to room temperature, washing the reaction solution to be neutral by using water, adding magnesium sulfate into the organic phase, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/N-heptane (1: 3 by volume) system to yield intermediate I-A-N as a pale yellow solid (15.08g, 79.33% yield).
Step (5)
Figure BDA0002690561090000372
Adding the intermediate I-A-N (13.0g,25.81mmol), 4-bromobiphenyl (6.02g,25.81mmol), tris (dibenzylideneacetone) dipalladium (0.24g,0.26mmol), 2-dicyclohexyl phosphorus-2 ',6' -dimethoxybiphenyl (0.21g,0.52mmol) and sodium tert-butoxide (3.72g,38.71mmol) into toluene (105mL), heating to 108 ℃ under the protection of nitrogen, stirring for 4h, then cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and decompressing the filtrate to remove the solvent; the crude product was purified by recrystallization from a toluene system to obtain compound 1 as a white solid (8.39g, yield 49.53%). Mass spectrum: 656.32[ M + H ] M/z]+. Nuclear magnetic data for compound 1:1H NMR(CD2Cl2,400MHz):8.36(d,1H),8.02(d,1H),7.89-7.83(m,2H),7.79-7.70(m,10H),7.65-7.56(m,7H),7.23(s,1H),7.18-7.04(m,4H),6.98(d,1H),2.87(d,2H),2.64(d,2H),2.15(s,1H),2.07(s,1H),1.85(s,2H),1.68(t,4H),1.54(s,2H).
examples 2 to 9
The compounds listed in Table 1 were prepared by referring to the synthesis method according to example 1, respectively, with the difference that in steps (4) and (5), specifically, 4-aminobiphenyl of step (4) of example 1 was replaced with raw material 1, and 4-bromobiphenyl of step (5) was replaced with raw material 2. The main raw materials and the corresponding synthesized compounds, the structure of the compounds, the yield of the last step and the mass spectrum result are shown in table 1.
TABLE 1
Figure BDA0002690561090000373
Figure BDA0002690561090000381
Example 10: preparation of Compound 157
Step (1)
Figure BDA0002690561090000391
Under the protection of nitrogen, 2-bromo-4-chloroiodobenzene (22.52g, 70.97mmol), 6-chloro-2-naphthalene boronic acid (14.06g, 68.13mmol), toluene (160mL), ethanol (800mL), water (40mL), and potassium carbonate (19.62g, 141.95mmol) are added into a reaction bottle, stirred, heated to 55 ℃, and rapidly added with tetrakis (triphenylphosphine) palladium (1.58g, 1.42mmol), tetrabutylammonium bromide (TBAB) (4.58g, 14.19mmol), then continuously heated to 70-75 ℃ for reflux reaction for 18h, after the reaction is finished, cooled to room temperature, extracted with dichloromethane, washed with organic phase water, dried organic phase, filtered and concentrated to obtain crude product. The crude product was recrystallized with a mixed solvent of dichloromethane and n-heptane to a LC purity of > 98%. Drying to obtain white solid intermediate I-O-1(18.85g, yield 75.8%).
Step (2)
Figure BDA0002690561090000392
Adding 16.4g (46.6mmol) of intermediate I-O-1 and 160mL of dried tetrahydrofuran into a 250mL three-neck flask, cooling to below-80 ℃ under stirring, slowly dropwise adding 24.5mL of n-butyllithium (48.93mmol) n-hexane solution with the concentration of 2mol/L under the protection of nitrogen, preserving heat for 30min after dropwise adding, then adding a mixed solution consisting of 43.5g (46.6mmol) of adamantanone and 60mL of tetrahydrofuran, preserving heat for 30min, continuing stirring for 2 h after naturally rising to room temperature, dropwise adding water to quench the reaction, extracting the reaction solution with ethyl acetate, drying an organic phase with magnesium sulfate, distilling under reduced pressure, recrystallizing an obtained solid crude product with a mixed solution of dichloromethane and n-heptane (volume ratio of 1: 5), and obtaining intermediate I-O-2(15.44g, yield of 78.3%).
Step (3)
Figure BDA0002690561090000393
14.5g (34.25mmol) of intermediate I-O-2 and 140mL of acetic acid are added into a 250mL three-neck flask, 14mL of concentrated sulfuric acid (with the concentration of 98 wt%) is slowly added dropwise under stirring, heating is started to raise the temperature to 80 ℃ for reaction for 8 hours, water is added into the reaction liquid, ethyl acetate is used for extraction, liquid separation is carried out, an organic phase is dried by magnesium sulfate and then reduced pressure distillation is carried out, the obtained crude product is recrystallized by using a mixed solvent of dichloromethane and n-heptane (the volume ratio is 1: 5), and intermediate I-O-3(9.35g, the yield is 67.4%) is obtained.
Step (4)
Figure BDA0002690561090000394
Under the protection of nitrogen, adding the intermediate I-O-3(9.2g, 22.69mmol), phenylboronic acid (2.63g, 21.63mmol), toluene (80mL), ethanol (40mL), water (20mL), potassium carbonate (6.58g, 47.58mmol), stirring, heating to 55 ℃, rapidly adding tetrakis (triphenylphosphine) palladium (0.48g, 0.43mmol) and tetrabutylammonium bromide (TBAB) (1.39g, 4.32mmol), after the addition, continuing heating to 70-75 ℃, refluxing for 18h, after the reaction is finished, cooling, extracting with dichloromethane, washing an organic phase with water, drying, filtering and concentrating. Recrystallization from a dichloromethane/n-heptane mixture (1: 4 by volume) to a LC purity of > 98%. Drying gave intermediate I-O as a white solid (6.33g, 65.6% yield).
Step (5)
Figure BDA0002690561090000401
Adding the intermediate I-O (6.0g,13.43mmol), 3-aminobiphenyl (2.39g,14.09mmol), tris (dibenzylideneacetone) dipalladium (0.12g,0.13mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.13g,0.27mmol) and sodium tert-butoxide (1.93g,20.13mmol) into toluene (50mL), heating to 108 ℃ under nitrogen protection, and stirring for 3 h; cooling to room temperature, washing the reaction solution to be neutral by using water, adding magnesium sulfate into the organic phase, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/N-heptane system (1: 3 by volume) to yield the intermediate I-O-N as a pale yellow solid (5.72g, 73.5% yield).
Step (6)
Figure BDA0002690561090000402
Adding the intermediate I-O-N (5.0g, 8.62mmol), 1-bromonaphthalene (1.82g, 8.79mmol), tris (dibenzylideneacetone) dipalladium (0.08g, 0.086mmol), 2-dicyclohexylphosphonium-2 ',6' -dimethoxybiphenyl (0.07g, 0.17mmol) and sodium tert-butoxide (1.24g, 12.94mmol) into toluene (50mL), heating to 108 ℃ under nitrogen protection, and stirring for 3 h; then cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization from toluene system to obtain 157(3.83g, yield 62.9%) as a white solid. Mass spectrum: 706.34[ M + H ] M/z]+。
Examples 11 to 51
Examples 11 to 51 were used for the preparation of the compounds shown in table 2, respectively.
1) Preparation of intermediates
1-1) preparation of intermediates I-B to I-S
Intermediates I-B to I-N were prepared according to the synthetic methods of steps (1) to (3) of example 1, respectively, except that 2-bromo-4-chloroiodobenzene of step (1) was replaced with raw material 3 and 2-naphthalene boronic acid of step (1) was replaced with raw material 4. The yields of the main raw materials and the intermediates prepared correspondingly, and the final step are shown in table 2.
TABLE 2
Figure BDA0002690561090000403
Figure BDA0002690561090000411
Figure BDA0002690561090000421
1-2) preparation of derivatized intermediates
1-2-1) preparation of intermediates I-A-L1, I-B-L1, I-B-L2, I-B-L3
The above intermediate was synthesized by referring to the procedure of step (4) of example 10, except that the intermediate I-O-3 of step (4) was replaced with the starting material 5 and the p-chlorobenzoic acid was replaced with the starting material 6, respectively. The starting materials and the intermediates prepared accordingly, as well as their numbers and yields are shown in table 3.
TABLE 3
Figure BDA0002690561090000422
Figure BDA0002690561090000431
1-2-2) preparation of intermediate I-P-L1
Figure BDA0002690561090000432
Adding the intermediate I-P (48g,121.232mmol), pinacol diboron (32.32g,119.701mmol), tris (dibenzylideneacetone) dipalladium (1.11g,1.212mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (1.16g,2.423mmol) and potassium acetate (23.79g,242.475mmol) to 1, 4-dioxane (400mL), heating to 80 ℃ under nitrogen protection, and stirring for 3 h; then cooling to room temperature, washing the reaction solution to be neutral, combining organic phases, adding 60g of anhydrous magnesium sulfate, drying overnight, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization from toluene to give the intermediate I-P-L1-1# (42.37g, yield 71.7%) as a pale yellow solid.
Figure BDA0002690561090000433
Under the protection of nitrogen, 3, 6-dibromo-9-phenylcarbazole (36.28g, 90.471mmol), an intermediate I-P-L-1# (42g, 86.163mmol), toluene (240mL), ethanol (120mL), water (60mL), potassium carbonate (26.16g, 189.558mmol) are added into a reaction bottle, then the mixture is stirred, heated to 50-60 ℃, tetrakis (triphenylphosphine) palladium (1.99g, 1.723mmol) and tetrabutylammonium bromide TBAB (5.55g,17.235mmol) are rapidly added, the mixture is continuously heated to 70-75 ℃ for reflux reaction for 18 hours, after the reaction is finished, the temperature is reduced, dichloromethane is used for extraction, an organic phase is washed to be neutral, anhydrous magnesium sulfate is used for drying, filtering is carried out, and the solvent is removed by reduced pressure distillation. Recrystallizing with a mixed solvent of ethyl acetate and n-heptane (volume ratio 1: 2). Drying to obtain intermediate I-P-L1(34.84g, 63.6%) as a white solid.
1-2-3) preparation of other derivative intermediates
Intermediates listed in table 4 were synthesized with reference to the preparation of intermediate I-P-L1, except that starting material 7 was used instead of intermediate I-P and starting material 8 was used instead of 3, 6-dibromo-9-phenylcarbazole, respectively. The main raw materials and the corresponding prepared target intermediate and the final yield thereof are shown in table 4.
TABLE 4
Figure BDA0002690561090000441
Figure BDA0002690561090000451
2) Preparation of the Compounds
Compounds were prepared with reference to steps (4) to (5) of example 1, except that intermediate 1-a in step (4) was replaced with raw material 9 (i.e., an intermediate synthesized in the above step), 4-aminobiphenyl was replaced with raw material 10, and 4-bromobiphenyl in step (5) was replaced with raw material 11. The structures, yields and mass spectrum characterization results of the used raw materials and the synthesized corresponding compounds are shown in table 5.
TABLE 5
Figure BDA0002690561090000452
Figure BDA0002690561090000461
Figure BDA0002690561090000471
Figure BDA0002690561090000481
Figure BDA0002690561090000491
Figure BDA0002690561090000501
EXAMPLE 55 preparation of Compound 388
Step (1)
Figure BDA0002690561090000502
Intermediate I-T-1 was prepared with reference to step (1) of example 1, except that: 2, 7-dibromophenanthrene (29g, 86.31mmol) was used in place of 2-bromo-4-chloroiodobenzene and triphenylamine 4-borate (24.94g, 86.31mmol) was used in place of 2-naphthalene boronic acid, respectively. Intermediate I-T-1(32.7g, 75.2%) was obtained.
Step (2)
Figure BDA0002690561090000503
Adding 32.5g (64.95mmol) of intermediate I-T-1 and 240mL of dried tetrahydrofuran into a 5000mL three-neck flask, cooling to below-80 ℃ under stirring, slowly dropwise adding 39mL of n-butyllithium (78mmol) n-hexane solution with the concentration of 2mol/L under the protection of nitrogen, preserving heat for 1h after dropwise adding, then slowly dropwise adding trimethyl borate (10.12g and 97.42mmol), preserving heat for 30min, naturally raising the temperature to room temperature, then continuing stirring for 2 h, dropwise adding 4mL of dilute hydrochloric acid with the mass concentration of 3.5% to hydrolyze, extracting the reaction liquid with ethyl acetate after stirring for 30min, drying the organic phase with magnesium sulfate, distilling under reduced pressure, and recrystallizing the obtained yellow solid crude product with a mixed solvent of ethyl acetate and n-heptane (the volume ratio of 1:3) to obtain intermediate I-T-2(25.72g and the yield of 85.1%).
Step (3)
Figure BDA0002690561090000511
Intermediate I-T-3 was prepared with reference to step (1) of example 1, except that: intermediate I-T-3(10.4g, 79.5%) was obtained by substituting intermediate I-T-2(10g, 21.49mmol) for 2-naphthaleneboronic acid.
Step (4)
Figure BDA0002690561090000512
Intermediate I-T-4 was prepared with reference to step (2) of example 1, except that: intermediate I-T-4(7.73g, 69.2%) was obtained by substituting intermediate I-T-3(10g, 16.37mmol) for intermediate I-A-2.
Step (5)
Figure BDA0002690561090000513
Intermediate I-T-5 was prepared with reference to step (3) of example 1, except that: intermediate I-T-5(4.23g, 57.9%) was obtained by substituting intermediate I-T-4(7.5g, 10.99mmol) for intermediate I-A-2.
Step (6)
Figure BDA0002690561090000514
Adding the intermediate I-T-5(4.0g,6.02mmol), carbazole (1.21g,7.23mmol), tris (dibenzylideneacetone) dipalladium (0.055g,0.06mmol), triphenylphosphine (0.032g,0.12mmol) and sodium tert-butoxide (1.157g,12.04mmol) into toluene (40mL), heating to 108 ℃ under the protection of nitrogen, and stirring for 24 h; cooling to room temperature, washing the reaction solution to be neutral by using water, adding magnesium sulfate into the organic phase, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization from dichloromethane/n-heptane (1: 3 by volume) to yield a white solid (2.6g, 54.4%). Mass spectrum: 795.36[ M + H ] M/z]+. Nuclear magnetic data for compound 388:1H NMR(CDCl2,400MHz):8.56(d,1H),8.28(s,1H),8.24(s,1H),8.06(s,1H),8.02-7.91(m,4H),7.80-7.76(m,3H),7.61(s,1H),7.47(d,2H),7.31-7.24(m,8H),7.15(d,1H),7.12(s,1H),7.08-7.02(m,4H),6.98(d,4H),2.83(d,2H),2.75(d,2H),2.17(s,1H),2.14(s,1H),1.93(s,2H),1.75(t,4H),1.46(s,2H).
application example 1: preparation of red organic electroluminescent device
The anode was prepared by the following procedure: the thickness of ITO is set as
Figure BDA0002690561090000521
Was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process using ultraviolet ozone and O2:N2The plasma was subjected to surface treatment to increase the work function of the anode (experimental substrate) and remove dross.
HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002690561090000522
And NPB is vapor-deposited on the hole injection layer to form a layer having a thickness of
Figure BDA0002690561090000523
The first hole transport layer of (1).
Vacuum evaporating compound 1 on the first hole transport layer to a thickness of
Figure BDA0002690561090000524
The second hole transport layer of (1). Depositing CBP as main material on the second hole transport layer and doping Ir (piq)2(acac) as a guest material, having a film thickness ratio of 100:3 and a thickness formed by vapor deposition
Figure BDA0002690561090000525
The light emitting layer (EML).
TPBi and LiQ are formed by co-evaporation with a film thickness ratio of 1:1
Figure BDA0002690561090000526
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
Figure BDA0002690561090000527
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 film thickness is formed on the electron injection layer by vacuum deposition to a thickness of
Figure BDA0002690561090000528
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA0002690561090000529
Forming an organic capping layer (CPL) to complete the fabrication of the organic light emitting device, and marking the fabricated device as a 1.
The vapor-deposited device a1 was encapsulated with an ultraviolet-curable resin in a nitrogen glove box.
The structures of the compounds used in the above layers are specifically shown below:
Figure BDA00026905610900005210
application examples 2 to 55
Organic electroluminescent devices were produced in the same manner as in application example 1 except that the compounds shown in table 6 were each used in place of compound 1 in forming the second hole transport layer, and the produced devices were denoted as a2 to a55, respectively. For example, in application example 2, an organic electroluminescent device was produced as shown in application example 1 using compound 3 instead of compound 1, and the produced device was designated as a 2.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in application example 1 except that compound a was used in forming the second hole transporting layer, and the produced device was denoted as D1.
Figure BDA0002690561090000531
Comparative example 2
An organic electroluminescent device was produced in the same manner as in application example 1, except that the compound B was used in forming the second hole transporting layer, and the produced device was denoted as D2.
Figure BDA0002690561090000532
Comparative example 3
An organic electroluminescent device was produced in the same manner as in application example 1, except that the compound C was used in forming the second hole transport layer, and the produced device was denoted as D3.
Figure BDA0002690561090000533
Comparative example 4
An organic electroluminescent device was produced in the same manner as in application example 1, except that the compound D was used in forming the second hole transporting layer, and the produced device was denoted as D4.
Figure BDA0002690561090000541
Devices A1-A51 and D1-D4 corresponding to application examples 1-55 and comparative examples 1-4 were at 10mA/cm2Was carried out under the conditions of (1) and (2) and at 15mA/cm2The devices were analyzed for T95 lifetime with the results shown in table 6 below.
TABLE 6
Figure BDA0002690561090000542
Figure BDA0002690561090000551
As is clear from table 5, the efficiency performance and the lifetime performance of the devices a1 to a55 are improved as compared with the devices D1 to D4. Specifically, the device D2 in comparative example 2 has the best overall effect, and compared with the comparative example, the light emitting efficiency of the devices a1 to a51 is 34.1 to 35.3Cd/a, which is 7.9 to 11.7% higher than that of the device D2, the life of T95 is 490 to 519h, which is 6.2 to 12.6% higher than that of the device D2, and the devices a1 to a55 also have lower driving voltages. Therefore, when the nitrogen-containing compound is used in a hole transport layer of an organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved and the service life of the organic electroluminescent device can be prolonged under the condition of ensuring that the device has lower driving voltage.
In the nitrogen-containing compound provided by the application, the adamantyl group is in threaded connection with a large condensed ring structure containing the fluorenyl group, the large condensed ring structure at least comprises the fluorenyl group and at least one aromatic ring condensed with the fluorenyl group, the large condensed ring structure has stronger conjugation compared with the fluorenyl group, and the aromatic amine is combined to be used as a core group of the nitrogen-containing compound so as to improve the hole migration capability of the nitrogen-containing compound. Moreover, the adamantyl group is an electron-rich group, and can further improve the electron density of a large condensed ring system through a super-conjugation effect, so that the hole migration capability of the nitrogen-containing compound is further improved. Thus, when the nitrogen-containing compound is used for a hole transport layer of an organic electroluminescent device, the light-emitting efficiency and the service life of the organic electroluminescent device can be improved under the condition of ensuring that the device has lower driving voltage.
The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.

Claims (16)

1. A nitrogen-containing compound having a structural formula shown in formula 1:
Figure FDA0002690561080000011
wherein, the ring A and the ring B are respectively and independently selected from a benzene ring or a condensed aromatic ring with 10-14 ring carbon atoms, and at least one of the ring A and the ring B is selected from the condensed aromatic ring;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 4 to 30 carbon atoms;
Q1and Q2The same or different, each independently selected from a halogen group, a cyano group, a halogenated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 7 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a heteroaryl group having 4 to 12 carbon atoms, and a heteroaralkyl group having 5 to 13 carbon atoms; n represents Q1The number of (3) is 0 or 1; m represents Q2The number of (3) is 0 or 1;
Ar1and Ar2The same or different, each is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 4-30 carbon atoms;
Ar1、Ar2and the substituents in L are the same or different and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms; at Ar1、Ar2And L, when two substituents are present on the same atom, optionally, the two substituents are linked to each other to form a 5-to 18-membered ring together with the atom to which they are linkedSaturated or unsaturated rings of (a).
2. The nitrogen-containing compound according to claim 1,
Figure FDA0002690561080000012
selected from the group consisting of the structures shown below:
Figure FDA0002690561080000013
wherein the content of the first and second substances,
Figure FDA0002690561080000021
represents a chemical bond; it shows the above structure for use in combination with
Figure FDA0002690561080000022
With the above structure for connection with
Figure FDA0002690561080000023
And (4) connecting.
3. The nitrogen-containing compound according to claim 1,
Figure FDA0002690561080000024
selected from the group consisting of the structures shown below:
Figure FDA0002690561080000025
wherein the content of the first and second substances,
Figure FDA0002690561080000026
represents a chemical bond; # denotes the above structure for use with
Figure FDA0002690561080000027
Connection, # # denotes the above structure for
Figure FDA0002690561080000028
And (4) connecting.
4. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 25 carbon atoms;
preferably, Ar1、Ar2Wherein the substituents in (a) are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.
5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each independently selected from the group consisting of formula i-1 through formula i-17:
Figure FDA0002690561080000029
Figure FDA0002690561080000031
wherein M is1Selected from a single bond or
Figure FDA0002690561080000032
Each ring C and D is a naphthalene ring;
G1～G5each independently selected from N or C (F)1) And G is1～G5At least one ofIs selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H1selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms and alkylthio having 1 to 10 carbon atoms;
H2～H9、H21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
H10～H20and H22～H23、F1～F4Each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, and halogen having 1 to 10 carbon atomsAn alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, and a heteroaryl group having 3 to 18 carbon atoms;
h1～h23by hkIs represented by H1～H23With HkK is a variable and represents an arbitrary integer of 1 to 23, hkRepresents a substituent HkThe number of (2); wherein, when k is selected from 5 or 17, hkSelected from 0, 1,2 or 3; when k is selected from 2,7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 23, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11 or 22, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; when k is 23, hkSelected from 1,2, 3,4, 5, 6, 7, 8, 9,10 or 11; and when h iskWhen greater than 1, any two HkThe same or different;
K1selected from O, S, Se, N (H)24)、C(H25H26)、Si(H25H26) (ii) a Wherein H24、H25、H26Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H25And H26Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 18-membered saturated or unsaturated ring;
K2selected from single bond, O, S, Se, N (H)27)、C(H28H29)、Si(H28H29) (ii) a Wherein H27、H28、H29Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H28And H29Are linked to form, together with the atoms to which they are commonly attached, a 5-to 18-membered saturated or unsaturated ring.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each independently selected from a substituted or unsubstituted group T, wherein the unsubstituted group T is selected from the group consisting of:
Figure FDA0002690561080000041
wherein, V3Is selected from C (R)1R2)、N(R3)、O、S、Se、Si(R1R2)，V4Selected from single bond, C (R)4R5)、N(R6)、O、S、Se、Si(R4R5)；R1、R2、R3、R4、R5、R6Each independently selected from: an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, or R1And R2Are linked to each other to form a 5-to 10-membered saturated ring together with the atoms to which they are commonly linked, or the above R4And R5Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 10-membered saturated ring;
the substituted group T has one or more than two substituent groups, the substituent groups are independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trimethylsilyl, pyridyl and cyclohexyl, and when the number of the substituent groups on the substituted group T is more than two, any two substituent groups are the same or different.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each independently selected from:
Figure FDA0002690561080000051
Figure FDA0002690561080000061
8. the nitrogen-containing compound according to claim 1, wherein L is selected from a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 24 carbon atoms;
preferably, the substituents in L are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.
9. The nitrogen-containing compound of claim 1, wherein L is selected from the group consisting of groups represented by formula j-1 through formula j-15:
Figure FDA0002690561080000071
wherein M is2Selected from a single bond or
Figure FDA0002690561080000072
D1～D5Each independently selected from N or C (F)5) And D is1～D5At least one is selected from N; when D is present1～D5Two or more of C (F)5) When, two arbitrary F5The same or different;
D6～D13each independently selected from N or C (F)6) And D is6～D13At least one is selected from N; when D is present6～D13Two or more of C (F)6) When, two arbitrary F6The same or different;
D14～D23each independently selected from N or C (F)7) And D is14～D23At least one is selected from N; when D is present14～D23Two or more of C (F)7) When, two arbitrary F7The same or different;
D24～D33each independently selected from N or C (F)8) And D is24～D33At least one is selected from N; when D is present24～D33Two or more of C (F)8) When, two arbitrary F8The same or different;
E1～E19、F5～F8each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3-18 carbon atoms, aryl with 6-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms and alkylthio with 1-10 carbon atoms;
e1～e19with erIs represented by1～E19With ErR is a variable and is an arbitrary integer of 1 to 19, erRepresents a substituent ErThe number of (2); when r is 17, erSelected from 1,2 or 3; when r is selected from 1,2, 3,4, 5, 6, 9, 13, 14, 18 or 19, erSelected from 1,2, 3 or 4; when r is selected from 15 or 16, erSelected from 1,2, 3,4 or 5; when r is selected from 7 or 11, erSelected from 1,2, 3,4, 5 or 6; when r is 12, erSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different;
K3selected from O, S, Se, N (E)20)、C(E21E22)、Si(E21E22) (ii) a Wherein，E20、E21、E22Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or E21And E22Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 18-membered saturated or unsaturated ring;
K4selected from the group consisting of a single bond, O, S, Se, N (E)23)、C(E24E25)、Si(E24E25) (ii) a Wherein E is23、E24、E25Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or E24And E25Are linked to form, together with the atoms to which they are commonly attached, a 5-to 18-membered saturated or unsaturated ring.
10. The nitrogen-containing compound of claim 1, wherein L is selected from a single bond, an unsubstituted group V, or a substituted group V, wherein the unsubstituted group V is selected from the group consisting of:
Figure FDA0002690561080000081
wherein, V1Is selected from C (R)7R8)、N(R9)、O、S、Se、Si(R7R8)，V2Selected from single bond, C (R)10R11)、N(R12)、O、S、Se、Si(R10R11)；R7、R8、R9、R10、R11、R12Each independently selected from: an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, or R7And R8Are linked to each other to form, together with the atoms to which they are commonly linked, a 5-to 13-membered saturated or unsaturated ring, or R as defined above10And R11Are interconnected to be common with themThe atoms connected form a saturated or unsaturated ring with 5-13 carbon atoms;
the substituted group V has one or more substituents selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, phenyl, trimethylsilyl and cyclohexyl, and when the number of the substituents on the substituted group V is more than two, any two substituents are the same or different.
11. The nitrogen-containing compound of claim 1, wherein L is selected from the group consisting of a single bond or the following group:
Figure FDA0002690561080000082
Figure FDA0002690561080000091
12. the nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0002690561080000092
Figure FDA0002690561080000101
Figure FDA0002690561080000111
Figure FDA0002690561080000121
Figure FDA0002690561080000131
Figure FDA0002690561080000141
Figure FDA0002690561080000151
Figure FDA0002690561080000161
Figure FDA0002690561080000171
Figure FDA0002690561080000181
Figure FDA0002690561080000191
Figure FDA0002690561080000201
Figure FDA0002690561080000211
Figure FDA0002690561080000221
Figure FDA0002690561080000231
Figure FDA0002690561080000241
Figure FDA0002690561080000251
13. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 12.
14. The electronic component according to claim 13, wherein the functional layer comprises a hole transport layer, and wherein the hole transport layer comprises the nitrogen-containing compound.
15. The electronic component according to claim 13 or 14, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
16. An electronic device comprising the electronic component according to any one of claims 13 to 15.
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