CN112812102B - Nitrogen-containing compound, electronic component, and electronic device - Google Patents

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

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CN112812102B
CN112812102B CN202010307832.3A CN202010307832A CN112812102B CN 112812102 B CN112812102 B CN 112812102B CN 202010307832 A CN202010307832 A CN 202010307832A CN 112812102 B CN112812102 B CN 112812102B
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containing compound
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张孔燕
李红燕
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Material Science Co Ltd
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Abstract

The application provides a nitrogen-containing compound shown in chemical formula 1, an electronic element and an electronic device, and belongs to the technical field of organic materials. The nitrogen-containing compound can improve the performance of an electronic component.
Figure DDA0002456407480000011

Description

Nitrogen-containing compound, electronic component, and electronic device
Technical Field
The present disclosure relates to the field of organic materials, and more particularly to a nitrogen-containing compound, an electronic device using the same, and an electronic device using the same.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components 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 electroluminescent 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 electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
Generally, an electron transport material has poor stability and low transport efficiency, and when the electron transport material is used for an organic electroluminescent device, hole electron transport cannot be truly balanced, so that the luminous efficiency of the device is reduced, and the service life of the device is shortened.
At present, although a large number of organic electroluminescent materials with excellent performance have been developed, for example, patent documents CN108912099A, CN103435597A, CN106883215A, etc. disclose some triazine compounds, there is still a need to develop new materials to further improve the performance of electronic components.
The above information disclosed in this 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, in order to improve the performance of the electronic component and the electronic device.
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 shown in chemical formula 1:
Figure BDA0002456407460000011
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wherein L is 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms;
Ar 1 selected from the following substituted or unsubstituted groups: alkyl with 1-20 carbon atoms, cycloalkyl with 3-20 carbon atoms, aryl with 6-30 carbon atoms and heteroaryl with 4-30 carbon atoms;
said L is 1 、Ar 1 And L 2 The substituents of (A) are one or more, and the same or different from each other, and each is independently selected from: deuterium, halogen group, cyano group, alkyl group, cycloalkyl group, heterocycloalkyl group, alkenyl group, cycloalkenyl group, alkoxy group, alkylthio group,Aryloxy, arylthio, alkylsilyl, arylsilyl, haloalkyl, aryl, heteroaryl.
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 one embodiment of the present application, the electronic component is an organic electroluminescent device. According to another embodiment of the present application, the electronic component is a solar cell.
According to a third aspect of the present application, there is provided an electronic device including the above electronic component.
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 view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 3 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic 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; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 370. a photoelectric conversion layer; 400. an electronic device; 500. an 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.
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. One skilled in the relevant art will recognize, however, that the embodiments of the application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring major technical ideas of the application.
The application provides a nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
Figure BDA0002456407460000031
wherein L is 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms;
Ar 1 selected from the following substituted or unsubstituted groups: alkyl with 1-20 carbon atoms, cycloalkyl with 3-20 carbon atoms, aryl with 6-30 carbon atoms and heteroaryl with 4-30 carbon atoms;
said L 1 、Ar 1 And L 2 The substituents of (A) are one or more, and the same or different from each other, and each is independently selected from: deuterium, halogen radical, cyano radical, alkyl radical, cycloalkyl radical, heterocycloalkyl radical, alkenyl radical, cycloalkenyl radical, alkoxy radical, alkylthio radical, aryloxy radical, arylthio radical, alkylmethyl radicalSilyl, arylsilyl, haloalkyl, aryl, heteroaryl.
The nitrogen-containing compound provided by the application comprises an aromatic amine group, a triazine group, a carbazole group and an adamantine group, wherein the aromatic amine group and the carbazole group have excellent hole transmission capability, the triazine group has better electron transmission capability, the triazine group is combined with the carbazole group, a conjugated system is added, and a continuous pi conjugate ties up better electron mobility, so that the nitrogen-containing compound has high electron mobility to balance carrier transmission, and further improves the voltage characteristic and the efficiency characteristic of an electronic element applying the nitrogen-containing compound, such as the open-circuit voltage and the photoelectric efficiency of a photoelectric conversion device, the driving voltage of an organic electroluminescent device is reduced, the luminous efficiency of the organic electroluminescent device is improved, and the nitrogen-containing compound can be used for an electron transmission layer. The conjugation and electron transfer of different functional groups are effectively interrupted by utilizing the rigid non-conjugated structure of adamantane, so that the compound has an energy level more matched with that of an adjacent layer, and the prepared organic electroluminescent device has low driving voltage. In addition, the compound provided by the application introduces a triphenylamine group and an adamantine group to expand a molecular system on the basis of a common triazine derivative substituted by carbazole, so that the overall molecular weight and asymmetry are enhanced, and the film-forming property of the molecule is improved.
On the other hand, in the nitrogen-containing compound molecule, by introducing adamantine groups with rigid non-conjugated structures into triarylamine groups and connecting the adamantine groups with carbazole-substituted triazine derivatives, the torsion angle is controlled, the HOMO and LUMO orbital distribution of the compound is effectively regulated, and the HOMO and LUMO are distributed on different units, so that holes and electrons can be favorably transferred on respective transmission units, a stable and uniform thin film can be formed in the preparation process of an electronic element, and the stability of the electronic element during operation is kept.
The triazine compound has a certain triplet state energy level and can also be used as a main material to be applied to a light-emitting layer of a light-emitting device, carbazole is of a nitrogen-containing heterocyclic structure, triazine is of a strong electron-deficient structure, the material has both hole transmission property and electron transmission property, hole and electron transmission balance in the light-emitting layer is realized, a region formed by carrier recombination and excitons is close to a light-emitting center and far away from the vicinity of a positive electrode or a negative electrode, a spacing unit is introduced between a triazine group used as an electron acceptor and an electron donor group, the spacing unit is specifically phenyl, naphthyl, biphenyl and pyridine, the distance between the electron donor and the electron acceptor is increased by the molecular structure, the dipole moment change in charge transfer conversion is further increased, and the radiative transition rate of material molecules is improved. According to the organic electroluminescent device provided by the application, the 1,3, 5-triazine derivative is used as a main material of the luminescent layer, so that the main material has bipolarity and a narrower energy gap, the electrons and holes are favorably compounded on the main material, the compounding area is increased, the exciton concentration is reduced, the exciton quenching is effectively reduced, and the problems of low efficiency and short service life caused by exciton quenching are solved.
Optionally, said L 1 、Ar 1 And L 2 Are the same or different from each other, and are each independently selected from: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, an alkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms.
In the present application, L 1 、Ar 1 And L 2 The substituent(s) may be one or more, and a plurality of substituents may be the same or different.
In the present application, L 1 、Ar 1 And L 2 The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L 1 、Ar 1 And L 2 Selected from the group consisting of substituted aryl groups having 20 carbon atoms, all of the carbon atoms of the aryl group and substituents thereon are 20.
In the application, the description mode of ' each 8230 ' \8230; ' and ' 8230 '; ' 823030 '; ' and ' 8230 '; ' are independently selected from ' interchangeable ' and should be broadly understood, which can mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example,'
Figure BDA0002456407460000041
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' exist on a benzene ring, each R ' can be the same or different, and the options of each R ' do not influence each other; the formula Q-2 shows that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced mutually.
In this application, the term "substituted or unsubstituted" means either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium (D), halogen groups (F, cl, br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, cycloalkyl, heterocycloalkyl.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
In the present application, the term "substituted or unsubstituted" means either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium (D), halogen groups (F, cl, br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, cycloalkyl, heterocycloalkyl.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have from 1 to 20 carbon atoms, and in this application, numerical ranges such as "1 to 20" refer to each integer in the given range. For example, "1 to 20 carbon atoms" refers to an alkyl group that may include 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The alkyl group can also be a medium size alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. Further, the alkyl group may be substituted or unsubstituted.
Preferably, the alkyl group is selected from alkyl groups having 1 to 10 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.
In the present application, "alkenyl" refers to a hydrocarbon group comprising one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups may be unsubstituted or substituted. Alkenyl groups may have 1 to 20 carbon atoms, and whenever appearing herein, numerical ranges such as "1 to 20" refer to each integer in the given range. For example, "1 to 20 carbon atoms" refers to an alkenyl group that can include 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. For example, the alkenyl group can be vinyl, butadiene, or 1,3, 5-hexatriene.
In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-20 carbon atoms, and numerical ranges such as "3 to 20" refer to each integer in the given range. For example, "3 to 20 carbon atoms" refers to a cycloalkyl group that can include 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The cycloalkyl group may be a small ring, a normal ring or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be divided into monocyclic-only one ring, bicyclic-two rings, polycyclic-three or more rings. Cycloalkyl groups can also be divided into spiro rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and more than two rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted.
Preferably, the cycloalkyl group is selected from cycloalkyl groups having 3 to 15 carbon atoms, specific examples including, but not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered an aryl group herein. Wherein the aryl group does not contain a hetero atom such as B, N, O, S or P. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quatiphenyl, pentabiphenyl, hexabiphenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl a benzofluoranthenyl group,
Figure BDA0002456407460000052
A phenyl group, a fluorenyl group, and the like, without being limited thereto.
In this application, substituted aryl refers to an aryl in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with deuterium atoms, F, cl, I, CN, branched alkyl, linear alkyl, cycloalkyl, alkoxy, or other groups. It is understood that a substituted aryl group having 18 carbon atoms refers to an aryl group and the total number of carbon atoms in the substituents on the aryl group being 18. For example, the number of carbon atoms of the 9, 9-dimethylfluorenyl group is 15. Wherein biphenyl can be interpreted as aryl or substituted phenyl.
In the present application, the fluorenyl group may be substituted and two substituents may be combined with each other to form a spiro structure, specific examples including, but not limited to, the following structures:
Figure BDA0002456407460000051
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 and S, in the ring or a derivative thereof. The heteroaryl group can be monocyclic heteroaryl or polycyclic heteroaryl, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems which are 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 may include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, 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-pyridylcarbazyl), N-alkylcarbazolyl (e.g., N-methylcarbazyl), and the like. 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 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.
In this application, the explanation for aryl applies to arylene and the explanation for heteroaryl applies equally to heteroarylene.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
Figure BDA0002456407460000061
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-7) includes any possible connection mode shown in the formula (f-1) to the formula (f-7).
Figure BDA0002456407460000062
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 through an delocalized bond extending from the middle of the phenyl ring on one side, and the meanings represented thereby include any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
Figure BDA0002456407460000063
/>
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 BDA0002456407460000064
In the present application, the halogen group may be fluorine, chlorine, bromine, iodine.
Optionally, said L 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: arylene having 6 to 20 carbon atoms and heteroarylene having 3 to 20 carbon atoms.
Preferably, said L 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: an arylene group having 6 to 18 carbon atoms.
Alternatively, L 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: selected from the group consisting of groups represented by the formula j-1 to groups represented by the formula j-14:
Figure BDA0002456407460000071
wherein M is 2 Selected from a single bond or
Figure BDA0002456407460000072
Q 1 ～Q 5 And Q' 1 ～Q’ 5 Each independently selected from N or C (J) 5 ) And Q is 1 ～Q 5 At least one is selected from N; when Q is 1 ～Q 5 Two of (1) orTwo or more selected from C (J) 5 ) When, two arbitrary J 5 Same or different, when Q' 1 ～Q’ 4 Two or more of them are selected from C (J) 5 ) When is two of any J 5 The same or different;
Q 6 ～Q 13 each independently selected from N or C (J) 6 ) And Q is 6 ～Q 13 At least one is selected from N; when Q is 6 ～Q 13 Two or more of them are selected from C (J) 6 ) When, two arbitrary J 6 The same or different;
Q 14 ～Q 23 each independently selected from N or C (J) 7 ) And Q is 14 ～Q 23 At least one is selected from N; when Q is 14 ～Q 23 Two or more of them are selected from C (J) 7 ) When is two of any J 7 The same or different;
Q 24 ～Q 32 each independently selected from N or C (J) 8 ) And Q is 24 ～Q 32 At least one is selected from N; when Q is 24 ～Q 32 Two or more of them are selected from C (J) 8 ) When, two arbitrary J 8 The same or different;
E 1 ～E 14 、J 5 ～J 8 each independently selected from: hydrogen, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthio group having 6 to 18 carbon atoms; j. the design is a square 5 ～J 8 、E 4 ～E 13 Any one of which may also be independently selected from aryl groups having 6 to 20 carbon atoms;
e 1 ～e 14 with e r Is represented by 1 ～E 14 With E r R is a variable and represents an arbitrary integer of 1 to 14, e r Represents a substituent E r The number of (2); when r is selected from 1,2,3,4,5,6, 9, 13 or 14, e r Selected from 1,2,3 or 4; when r is selected from 7 or 11, e r Selected from 1,2,3,4,5 or 6; when r is 12, e r Selected from 1,2,3,4,5,6 or 7; when r is selected from 8 or 10, e r Selected from 1,2,3,4,5,6,7 or 8; when e is r When greater than 1, any two of E r The same or different;
K 3 selected from O, S, se, N (E) 15 )、C(E 16 E 17 )、Si(E 18 E 19 ) (ii) a Wherein E is 15 、E 16 、E 17 、E 18 And E 19 Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, or E 16 And E 17 Are linked to each other so as to form, with the atoms to which they are commonly linked, a saturated or unsaturated ring having 3 to 15 carbon atoms, or E 18 And E 19 Are linked to each other so as to form, with the atoms to which they are commonly linked, a saturated or unsaturated ring having a carbon number of 3 to 15;
K 4 selected from the group consisting of single bond, O, S, se, N (E) 20 )、C(E 21 E 22 )、Si(E 23 E 24 ) (ii) a Wherein E is 20 To E 24 Each independently selected from: an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, or E 21 And E 22 Form of atoms linked to each other to be commonly bound to themA saturated or unsaturated ring having 3 to 15 carbon atoms, or E 23 And E 24 Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked.
Optionally, said L 1 And L 2 Each independently selected from the following substituted or unsubstituted groups: phenylene, naphthylene, biphenylene, terphenylene, dimethylfluorenylene.
Preferably, said L 1 、L 2 The substituents of (A) are each independently selected from alkyl groups having 1 to 4 carbon atoms.
More preferably, said L 1 、L 2 Each of the substituents of (a) is independently selected from methyl.
Optionally, said L 1 、L 2 Each independently selected from the group consisting of:
Figure BDA0002456407460000091
preferably, L 1 Selected from the group consisting of:
Figure BDA0002456407460000092
preferably, L 1 Selected from the group consisting of, but not limited to:
Figure BDA0002456407460000093
preferably, L 2 Selected from the group consisting of:
Figure BDA0002456407460000094
preferably, L 2 Selected from the group consisting of, but not limited to:
Figure BDA0002456407460000095
alternatively, ar 1 Selected from the following substituted or unsubstituted groups: aryl group having 6 to 25 carbon atoms and heteroaryl group having 5 to 24 carbon atoms.
Alternatively, ar 1 Selected from the group consisting of:
Figure BDA0002456407460000096
/>
Figure BDA0002456407460000101
wherein, M is 1 Selected from a single bond or
Figure BDA0002456407460000102
Y is selected from C (R) 1 R 2 )、N(R 3 )、O、S、Se、Si(R 1 R 2 )；
R 1 ，R 2 ，R 3 The same or different from each other, are independently selected from aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, or R 1 And R 2 Are linked to each other so as to form, with the atoms to which they are commonly linked, a saturated or unsaturated ring having a carbon number of 3 to 15;
W 1 to W 5 Each independently selected from CH or N, and at least one is N;
T 1 selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 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, and an alkylthio group having 1 to 10 carbon atoms;
T 5 to T 9 、T 15 Independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 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 heteroaryl group having 3 to 18 carbon atoms;
T 2 、T 3 、T 4 、T 10 to T 14 Selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 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, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;
T 1 ～T 15 by T r Is represented by e 1 ～e 15 With e r Is represented by e r Is a substituent T r Wherein r represents a variable and is selected from any integer of 1 to 15, when e r When greater than, any two T r The same or different;
e 1 ，e 5 ，e 7 each independently selected from 0, 1,2,3,4 or 5;
e 2 ，e 10 ，e 14 each independently selected from 0, 1,2,3,4,5,6, or 7;
e 3 ，e 4 each independently selected from 0, 1,2,3,4,5,6,7,8 or 9;
e 6 ，e 8 ，e 9 ，e 12 ，e 13 ，e 15 each independently selected from 0, 1,2,3 or 4;
e 11 selected from 0, 1,2,3,4,5,6,7 or 8.
In the group
Figure BDA0002456407460000111
In (B) when M 1 Is a single bond and e 10 When 0, Y is C (R) 1 R 2 ) When the temperature of the water is higher than the set temperature,R 1 and R 2 When the atoms which are linked together to form a five-membered ring form together with them, i.e. </R>
Figure BDA0002456407460000112
Likewise, the radical may represent->
Figure BDA0002456407460000113
Namely R 1 And R 2 The atoms that are linked to each other to be commonly bound to them form a partially unsaturated 13-membered ring.
Alternatively, ar 1 Selected from the group consisting of:
Figure BDA0002456407460000114
Figure BDA0002456407460000121
alternatively, ar 1 Selected from the group consisting of, but not limited to:
Figure BDA0002456407460000122
/>
Figure BDA0002456407460000131
optionally, the nitrogen-containing compound is selected from the group consisting of, but not limited to:
Figure BDA0002456407460000132
/>
Figure BDA0002456407460000141
/>
Figure BDA0002456407460000151
/>
Figure BDA0002456407460000161
/>
Figure BDA0002456407460000171
/>
Figure BDA0002456407460000181
/>
Figure BDA0002456407460000191
/>
Figure BDA0002456407460000201
/>
Figure BDA0002456407460000211
/>
Figure BDA0002456407460000221
/>
Figure BDA0002456407460000231
the application also provides an electronic component for realizing photoelectric conversion or electro-optical conversion. The electronic element comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises a nitrogen-containing compound of the present application.
For example, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, 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.
Alternatively, the functional layer 300 includes an electron transport layer 350, the electron transport layer 350 comprising a nitrogen-containing compound as provided herein. The electron transport layer 350 may be made of the nitrogen-containing compound provided herein, or may be made of the nitrogen-containing compound provided herein and other materials. As in some embodiments of the present application, the electron transport layer 350 is composed of the present nitrogen-containing compound and LiQ.
In one embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked. The nitrogen-containing compound provided by the application can be applied to the electron blocking layer 322 of the organic electroluminescent device, can effectively improve the luminous efficiency and the service life of the organic electroluminescent device, and reduces the driving voltage of the organic electroluminescent device.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: 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 SnO 2 Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. For example, in one embodiment of the present application, the hole transport layer 321 is composed of the compound NPB.
Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking materials may be selected from carbazole multimers or other types of compounds, which are not particularly limited in this application. For example, in some embodiments of the present application, the electron blocking layer 322 is composed of the compound TCTA.
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. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic 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 α, β -ADN.
In another embodiment of the present application, the host material of the organic light emitting layer 330 may also include the nitrogen-containing compound of the present application.
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 BD-1.
In another embodiment of the present application, the guest material of the organic layer 330 may be GD.
Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodiumPotassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca, but is not limited thereto. Preferably, an alloy metal electrode comprising silver and magnesium is included as the cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the 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. In one embodiment of the present application, the hole injection layer 310 may be composed of m-MTDATA.
Optionally, as shown in fig. 1, an electron injection layer 360 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 350. The electron injection layer 360 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. In one embodiment of the present application, the electron injection layer 360 may include LiQ.
Optionally, a hole blocking layer 340 may be further disposed between the organic electroluminescent layer 330 and the electron transport layer 350.
As another example, the electronic component may be a photoelectric conversion device, as shown in fig. 2, which may include an anode 100 and a cathode 200 oppositely disposed, 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.
Alternatively, the functional layer 300 includes an electron transport layer 350, the electron transport layer 350 comprising a nitrogen-containing compound as provided herein. The electron transport layer 350 may be made of the nitrogen-containing compound provided herein, or may be made of the nitrogen-containing compound provided herein and other materials.
Alternatively, as shown in fig. 2, the photoelectric conversion device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked. The nitrogen-containing compound provided by the application can be applied to the electron transport layer 350 of the photoelectric conversion device, can effectively improve the luminous efficiency and the service life of the photoelectric conversion device, and can improve the open-circuit voltage of the photoelectric conversion device.
Optionally, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321.
Optionally, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350.
Optionally, a hole blocking layer 340 may be further disposed between the photoelectric conversion layer 370 and the electron transport layer 350.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, as shown in fig. 2, in one embodiment of the present application, the solar cell includes an anode 100, a hole transport layer 321, an electron blocking layer 322, a photoelectric conversion layer 370, an electron transport layer 350, and a cathode 200, which are sequentially stacked, wherein the electron transport layer 350 includes the nitrogen-containing compound of the present application.
Embodiments also provide an electronic device including any one of the electronic elements described in the above electronic element embodiments. Since the electronic device has any one of the electronic elements described in the above embodiments of the electronic element, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.
For example, as shown in fig. 3, the present application provides an electronic device 400, and the electronic device 200 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device 400 has any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, the same advantages are obtained, and details are not repeated herein.
As another example, as shown in fig. 4, the present application provides an electronic device 500, where the electronic device 500 includes any one of the photoelectric conversion devices described in the above embodiments of the photoelectric conversion device. The electronic device 500 may be a solar power generation device, a light detector, a fingerprint recognition device, a light module, a CCD camera, or other types of electronic devices. Since the electronic device 500 has any one of the photoelectric conversion devices described in the above embodiments of the photoelectric conversion device, the same advantages are obtained, and details are not repeated herein.
Hereinafter, the present application will be described in further detail with reference to examples. However, the following examples are merely illustrative of the present application and do not limit the present application.
Synthesis of compounds
Synthesis example 1: synthesis of Compound 8
Figure BDA0002456407460000261
Adding carbazole (35g, 209.53mmol) into dehydrated THF (525 ml), dissolving and stirring in a three-neck flask, cooling to-5-0 ℃ under the protection of nitrogen, slowly dropwise adding n-butyllithium (80ml, 199.55mmol, 2.5M) solution at low temperature, keeping the temperature and stirring for 30min.2,4, 6-trichloro-1, 3, 5-triazine (18.40g, 99.77mmol) was dissolved in THF (200 ml) and added dropwise to a three-necked flask, and the mixture was heated to 70 ℃ under nitrogen and stirred under reflux for 6 hours. After the reaction is finished, cooling the solution to room temperature, adding dichloromethane and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; the crude product was purified by silica gel column chromatography to give intermediate 1-1 as a white solid (27.24 g, yield 61.23%).
Figure BDA0002456407460000262
Intermediate 1-1 (27.00g, 60.55mmol), p-chlorobenzoic acid (9.66g, 61.76mmol), tetrakis (triphenylphosphine) palladium (1.40g, 1.21mmol), potassium carbonate (18.41g, 133.21mmol), tetrabutylammonium chloride (0.33g, 1.21mmol), toluene (216 mL), ethanol (108 mL) and deionized water (54 mL) were added to a three-necked flask, heated to 75-80 ℃ under nitrogen, heated to reflux and stirred for 8h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; purification by silica gel column chromatography using n-heptane as the mobile phase gave solid intermediate 1-2 (23.77 g, yield 75.21%).
Figure BDA0002456407460000271
1-adamantanol (50.0g, 328.4mmol), bromobenzene (51.6g, 328.4mmol) and dichloromethane (500 mL) are added into a round-bottom flask, the temperature is reduced to-5-0 ℃ under the protection of nitrogen, trifluoromethanesulfonic acid (73.9g, 492.6mmol) is added dropwise at the temperature of-5-0 ℃, and the mixture is stirred for 3 hours under the condition of heat preservation; deionized water (300 mL) was added to the reaction mixture, the mixture was washed with water to pH =7, methylene chloride (100 mL) was added to extract the mixture, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to obtain intermediate 1-3 (53.1 g, yield 55.4%) as a white solid.
Figure BDA0002456407460000272
Adding the intermediates 1-3 (7.0g, 24.04mmol), aniline (2.69g, 28.84mmol), tris (dibenzylideneacetone) dipalladium (0.22g, 0.24mmol), 2-dicyclohexyl phosphorus-2 ',4',6' -triisopropyl biphenyl (x-phos) (0.23g, 0.48mmol) and sodium tert-butoxide (3.46g, 36.05mmol) into toluene (60 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3h; then cooling to room temperature, washing the reaction solution by using deionized water, adding anhydrous magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford intermediates 1-4 as pale green solids (5.83 g, yield 79.9%).
Figure BDA0002456407460000273
Adding the intermediates 1-2 (3.5g, 6.70mmol), the intermediates 1-4 (2.14g, 7.04mmol), the tris (dibenzylideneacetone) dipalladium (0.06g, 0.06mmol), the x-phos (0.06g, 0.13mmol) and the sodium tert-butoxide (0.96g, 10.05mmol) into toluene (35 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 8 (3.81 g, 72.12% yield). m/z =789.4[ m ] +H] + 。
Compound 8 nuclear magnetic data: 1 H NMR(400MHZ,CD 2 Cl 2 )δ8.62(d,2H,CH),δ8.18(d,4H,CH),δ8.13(d,2H,CH),δ8.08(d,2H,CH),δ7.40(m,6H,CH)，δ7.29-7.23(m,6H,CH),δ7.18(d,2H,CH)，δ7.13-7.05(m,5H,CH)，δ2.14(s，3H,CH),δ1.94(s，6H,CH 2 ),1.82-1.76(m，6H,CH 2 )
synthesis example 2: synthesis of Compound 16
Figure BDA0002456407460000281
Adding the intermediates 1-3 (4.00g, 13.73mmol), 2-naphthylamine (2.06g, 14.42mmol), tris (dibenzylideneacetone) dipalladium (0.12g, 0.14mmol), x-phos (0.13g, 0.27mmol) and sodium tert-butoxide (1.98g, 20.06mmol) into toluene (40 mL), heating to 105-110 ℃ under nitrogen and stirring for 3h; cooling to room temperature, washing the reaction solution with deionized water, adding anhydrous magnesium sulfate, drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford solid intermediate 2-4 (3.95 g, 81.54% yield).
Figure BDA0002456407460000282
Intermediate 1-2 (4.50g, 8.62mmol), intermediate 2-4 (3.19g, 9.05mmol), tris (dibenzylideneacetone) dipalladium(0.07g, 0.08mmol), x-phos (0.08g, 0.17mmol) and sodium tert-butoxide (1.24g, 12.93mmol) in toluene (45 mL) heated to 105-110 ℃ under nitrogen and stirred for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 16 (4.87 g, 67.37% yield). m/z =839.4[ m ] +H] +
Synthesis example 3: synthesis of Compound 6
Figure BDA0002456407460000283
Adding the intermediates 1-3 (4.00g, 13.73mmol), 2-aminobiphenyl (2.44g, 14.42mmol), tris (dibenzylideneacetone) dipalladium (0.12g, 0.14mmol), x-phos (0.13g, 0.27mmol) and sodium tert-butoxide (1.98g, 20.60mmol) into toluene (40 mL), heating to 105-110 ℃ under nitrogen protection, and stirring for 3h; then cooling to room temperature, washing the reaction solution by using deionized water, adding anhydrous magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford intermediate 3-4 as a solid (3.05 g, yield 72.40%).
Figure BDA0002456407460000284
Adding the intermediates 1-2 (4.00g, 7.66mmol), the intermediates 3-4 (3.05g, 8.05mmol), the bis-palladium tris (dibenzylideneacetone) (0.07g, 0.08mmol), the x-phos (0.08g, 0.15mmol) and the sodium tert-butoxide (1.10g, 11.49mmol) into toluene (40 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 6 (4.46 g, 67.49% yield). m/z =865.4[ m ] +H] +
Nuclear magnetic data for compound 6: 1 HNMR(400MHZ,CD 2 Cl 2 )δ8.64(d,4H,CH),δ8.17(m,6H,CH),δ8.08(d,2H,CH),δ7.45-7.34(m,8H,CH),δ7.29-7.18(m,8H,CH),δ7.13(d,2H,CH),δ7.02(d,1H,CH),δ6.90(d,2H,CH),δ2.14(s，3H,CH),δ1.94(s，6H,CH 2 ),1.82-1.76(m，6H,CH 2 )
synthesis example 4: synthesis of Compound 19
Compound 19 was synthesized in the same manner as in Synthesis example 1,2,3, except that aniline in the Synthesis of intermediates 1 to 4 in Synthesis example 1 was replaced with 3-aminodibenzofuran, and the detection yield was 68.93%, and the product mass spectrum m/z =879.37[ 2 ], [ M + H ] +] + 。
Figure BDA0002456407460000291
Nuclear magnetic data for compound 19: 1 HNMR(400MHZ,CD 2 Cl 2 )δ8.64(d,4H,CH),δ8.16(d,2H,CH),δ8.08(d,4H,CH),δ7.96(m,2H,CH),δ7.48-7.36(m,8H,CH),δ7.33-7.25(m,7H,CH),δ7.07(s,1H,CH),δ6.91(d,1H,CH),δ6.85(d,2H,CH),δ2.13(s，3H,CH),δ1.95(s，6H,CH 2 ),1.84-1.77(m，6H,CH 2 )
synthesis example 5: synthesis of Compound 48
Figure BDA0002456407460000292
Adding 1-adamantanol (10.0g, 65.69mmol), 4-bromobiphenyl (15.31g, 65.69mmol) into a round-bottom flask containing dichloromethane (150 mL), cooling to (-20) (-10) DEG C and (-20) - (-10) DEG C under the protection of nitrogen, dropwise adding trifluoromethanesulfonic acid (14.7g, 98.53mmol), keeping the temperature and stirring for 6h; adding deionized water (100 mL) to the reaction solution, washing with water to pH =7, adding MC (100 mL) to extract, combining the organic phases, drying over anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to obtain intermediate 5-3 (9.80 g, yield 40.61%) as a white solid.
Figure BDA0002456407460000293
Adding intermediate 5-3 (9.50g, 25.89mmol), 4-aminobiphenyl (4.60g, 27.18mmol), tris (dibenzylideneacetone) dipalladium (0.24g, 0.26mmol), x-phos (0.25g, 0.52mmol) and sodium tert-butoxide (3.73g, 38.83mmol) into toluene (100 mL), heating to 105-110 ℃ under nitrogen and stirring for 3h; then cooling to room temperature, washing the reaction solution by using deionized water, adding anhydrous magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; recrystallization purification of the crude product using a dichloromethane/n-heptane system yielded solid intermediate 5-4 (8.71 g, 73.88% yield).
Figure BDA0002456407460000301
Adding the intermediates 1-2 (3.00g, 5.74mmol), the intermediates 5-4 (2.75g, 6.03mmol), the bis-palladium tris (dibenzylideneacetone) (0.05g, 0.057 mmol), the x-phos (0.05g, 0.111mmol) and the sodium tert-butoxide (0.83g, 8.62mmol) into toluene (30 mL), heating to 105-110 ℃ under nitrogen protection, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 48 (3.82 g, yield 70.84%). m/z =941.4[ m ] +H] + 。
Synthesis example 6: synthesis of Compound 60
Figure BDA0002456407460000302
Intermediate 5-3 (5.00g, 13.61mmol), 4-aminopyridine (1.34g, 14.29mmol), tris (dibenzylideneacetone) dipalladium (0.12g, 0.14mmol), x-phos (0.13g, 0.27mmol) and sodium t-butoxide (1.96g, 20.41mmol) were added to toluene (50 mL), heated to 105-110 ℃ under nitrogen and stirred for 3h; then cooling to room temperature, washing the reaction solution by using deionized water, adding anhydrous magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford intermediate 6-4 as a solid (3.97 g, yield 76.88%).
Figure BDA0002456407460000303
Adding the intermediate 1-2 (4.50g, 8.62mmol), the intermediate 6-4 (3.44g, 9.05mmol), the tris (dibenzylideneacetone) dipalladium (0.07g, 0.086 mmol), the x-phos (0.08, 0.17mmol) and the sodium tert-butoxide (1.24g, 12.93mmol) into toluene (45 mL), heating to 105-110 ℃ under nitrogen protection, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 60 (5.10 g, yield 68.47%). m/z =866.4[ m ] +H] + 。
Synthesis example 7 Synthesis of Compound 67
The 4-aminobiphenyl in the synthesis process of the intermediate 5-4 in synthesis example 5 is replaced by 3-methylaniline, and the compound 67 is synthesized by the same method as synthesis examples 5 and 6, the detection yield is 64.89%, and the product mass spectrum m/z =879.41[ m ] +H ]] + 。
Figure BDA0002456407460000311
Synthesis example 8 Synthesis of Compound 77
The 4-aminobiphenyl in the synthesis process of the intermediate 5-4 in synthesis example 5 is replaced by 2-phenanthrene amine, and the compound 77 is synthesized by the same method as synthesis examples 5 and 6, the detection yield is 64.89%, and the product mass spectrum m/z =965.43[ 2 ], [ M ] +H ]] + 。
Figure BDA0002456407460000312
Synthesis example 9: synthesis of Compound 65
The 4-aminobiphenyl in the synthesis process of the intermediate 5-4 in synthesis example 5 is replaced by 3-aminodibenzothiophene, and the compound 65 is synthesized by the same method as in synthesis examples 5 and 6, the detection yield is 70.10%, and the mass spectrum m/z =971.83[ 2 ], [ M ] +H ] +.
Figure BDA0002456407460000321
Synthesis example 10: synthesis of Compound 81
Figure BDA0002456407460000322
Intermediate 1-1 (10.00g, 22.42mmol), 3-chlorobenzeneboronic acid (3.68g, 23.54mmol), tetrakis (triphenylphosphine) palladium (0.52, 0.45mmol), potassium carbonate (6.82g, 49.33mmol), tetrabutylammonium chloride (0.31g, 1.12mmol), toluene (80 mL), ethanol (40 mL) and deionized water (20 mL) were added to a three-necked flask, warmed to 75-80 ℃ under nitrogen, heated to reflux and stirred for 8h. After the reaction is finished, cooling the solution to room temperature, adding toluene and water to extract the reaction solution, combining organic phases, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating; purification by silica gel column chromatography using n-heptane as the mobile phase gave intermediate 10-2 as a solid (7.75 g, yield 64.78%).
Figure BDA0002456407460000323
Adding intermediate 10-2 (4.40g, 8.43mmol), intermediate 1-4 (2.68g, 8.85mmol), tris (dibenzylideneacetone) dipalladium (0.07g, 0.084mmol), x-phos (0.08, 0.17mmol) and sodium tert-butoxide (1.21g, 12.64mmol) into toluene (45 mL), heating to 105-110 ℃ under nitrogen and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 81 (4.30 g, 64.74% yield). m/z =789.36[ m + H ]] + 。
Synthesis example 11: synthesis of Compound 82
Figure BDA0002456407460000331
Compound 82 was synthesized in the same manner as in Synthesis example 1, except that intermediates 1-2 in Synthesis example 10 were replaced with intermediate 10-2. Intermediate 10-2 (5.50g, 10.53mmol), intermediate 2-4 (3.91g, 11.06mmol),adding tris (dibenzylideneacetone) dipalladium (0.09g, 0.10mmol), x-phos (0.1, 0.21mmol) and sodium tert-butoxide (1.51g, 15.80mmol) into toluene (55 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 82 (5.60 g, yield 63.45%). m/z =839.38[ m + H ]] + 。
Synthesis example 12: synthesis of Compound 83
Figure BDA0002456407460000332
Compound 83 was synthesized in the same manner as in Synthesis example 1, except that intermediates 1-2 in Synthesis example 1 were replaced with intermediate 10-2. Adding the intermediate 10-2 (5.20g, 9.96mmol), 3-4 (3.96g, 10.45mmol), tris (dibenzylideneacetone) dipalladium (0.09g, 0.09mmol), x-phos (0.09, 0.19mmol) and sodium tert-butoxide (1.46g, 14.94mmol) into toluene (50 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 83 (5.44 g, yield 63.26%). m/z =865.39[ m ] +H] +
Synthesis example 13: synthesis of Compound 84
Figure BDA0002456407460000341
Adding 1-adamantanol (10.0g, 65.69mmol), 1-bromonaphthalene (12.95g, 62.56mmol) and dichloromethane (120 mL) into a round-bottom flask, cooling to (-20) - (-10) DEG C under the protection of nitrogen, dropwise adding trifluoromethanesulfonic acid (14.08g, 93.84mmol) at (-20) - (-10) DEG C, and stirring for 6 hours under heat preservation; adding deionized water (300 mL) into the reaction solution, washing with water to pH =7, adding MC (50 mL) for extraction, combining the organic phases, drying with anhydrous magnesium sulfate, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to obtain intermediate 13-3 (12.58 g, yield 58.92%) as a white solid.
Figure BDA0002456407460000342
Adding the intermediate 13-3 (10g, 29.30mmol), aniline (2.87g, 30.77mmol), tris (dibenzylideneacetone) dipalladium (0.27g, 0.29mmol), x-phos (0.28g, 0.59mmol) and sodium tert-butoxide (4.22g, 43.95mmol) into toluene (80 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3 hours; then cooling to room temperature, washing the reaction solution by using deionized water, adding anhydrous magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, and removing the solvent under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to afford intermediate 13-4 as a solid (7.63 g, 73.65% yield).
Figure BDA0002456407460000343
Adding intermediate 10-2 (5.10g, 9.77mmol), intermediate 13-4 (3.62g, 10.25mmol), tris (dibenzylideneacetone) dipalladium (0.09g, 0.09mmol), x-phos (0.09, 0.19mmol) and sodium tert-butoxide (1.40g, 14.65mmol) into toluene (50 mL), heating to 105-110 ℃ under the protection of nitrogen, and stirring for 3 hours; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 84 (5.05g, 61.75%). m/z =839.38[ m + H ]] +
Synthesis example 14: synthesis of Compound 85
Figure BDA0002456407460000351
Adding 1-adamantanol (10.0g, 65.69mmol), o-bromotoluene (11.23g, 65.69mmol) and dichloromethane (120 mL) into a round-bottom flask, cooling to (-45) - (-35) DEG C and (-45) - (-35) DEG C under the protection of nitrogen, dropwise adding trifluoromethanesulfonic acid (14.78g, 98.53mmol), and stirring for 5 hours under the condition of heat preservation; adding deionized water (300 mL) to the reaction solution, washing with water to pH =7, adding MC (50 mL) to extract, combining the organic phases, drying with anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using n-heptane as a mobile phase to give intermediate 14-3 (12.84 g, yield 63.94%) as a white solid. Intermediate 14-4 was synthesized in the same manner as in Synthesis example 1 from intermediate 14-3 in Synthesis example 14, and the yield was 75.12%.
Figure BDA0002456407460000352
Adding intermediate 10-2 (5.50g, 10.53mmol), intermediate 14-4 (4.35g, 11.06mmol), tris (dibenzylideneacetone) dipalladium (0.09g, 0.10 mmol), x-phos (0.10, 0.21mmol) and sodium tert-butoxide (1.51g, 15.80mmol) into toluene (55 mL), heating to 105-110 ℃ under nitrogen protection, and stirring for 3h; cooling to room temperature, cooling the reaction solution to room temperature, separating out solids, and washing with water and ethanol; purification using silica gel chromatography gave compound 85 (5.90 g, yield 63.79%). m/z =879.41[ m ] +H] +
Synthesis example 15: synthesis of Compound 86
3-aminobiphenyl in the synthesis process of the intermediate 14-4 in synthesis example 14 is replaced by 3-aminodibenzothiophene, and the compound 86 is synthesized by the same method as in synthesis examples 5 and 6, with the detection yield of 67.90%, and the mass spectrum m/z =909.37[ M ] +H of the product] + 。
Figure BDA0002456407460000361
Synthesis examples 16 to 20
Intermediates 16-4 to 20-4 were prepared in the same manner as intermediate 1-4 in Synthesis example 1, except that the aniline in Experimental example 1 was replaced with the raw materials in Table 1. The compounds shown in Table 1 below were prepared in the same manner as in Experimental example 1
Table 1 compound structure, preparation and characterization data
Figure BDA0002456407460000362
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Figure BDA0002456407460000371
Preparation and evaluation of organic electroluminescent device
Example 1
Blue organic electroluminescent device
The anode was prepared by the following procedure: the thickness of ITO/Ag/ITO is
Figure BDA0002456407460000372
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 O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
The m-MTDATA (CAS No.: 124729-98-2) was vacuum evaporated on the experimental substrate (anode) to a thickness of
Figure BDA0002456407460000381
And NPB (CAS No. 123847-85-8) is vacuum-evaporated on the hole injection layer to form a film having a thickness of ^ 4>
Figure BDA0002456407460000382
A Hole Transport Layer (HTL).
TCTA (CAS No.: 139092-78-7) was vapor-deposited on the hole transport layer to a thickness of
Figure BDA0002456407460000383
Electron Blocking Layer (EBL).
Alpha, beta-ADN (CAS No.: 122648-99-1) was used as a host, and BD-1 was doped at a weight ratio of 3% to form a film having a thickness of
Figure BDA0002456407460000384
The light emitting layer (EML).
Compound 8 and LiQ were mixed at a weight ratio of 1 and vapor-deposited to form compound 8
Figure BDA0002456407460000385
A thick Electron Transport Layer (ETL), and LiQ is evaporated on the electron transport layer to form a thickness ^ H>
Figure BDA0002456407460000386
Then magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1>
Figure BDA0002456407460000387
The cathode of (1).
Further, the cathode is deposited with a thickness of
Figure BDA0002456407460000388
Forming a capping layer (CP-1) to complete the fabrication of the organic light emitting device.
The functional material and the main material used by the invention have the following structures:
Figure BDA0002456407460000389
Figure BDA0002456407460000391
examples 2 to 16
Blue organic electroluminescent devices were fabricated in the same manner as in example 1, using the corresponding compounds in table 2 in place of compound 8, and the properties of the fabricated devices are shown in table 2.
Comparative example 1
A blue organic electroluminescent device was produced in the same manner as in example 1, using compound a instead of compound 8.
Comparative example 2
A blue organic electroluminescent device was produced in the same manner as in example 1, using compound B instead of compound 8.
Comparative example 3
Using the compound Alq 3 A blue organic electroluminescent device was produced in the same manner as in example 1, except for using compound 8.
Comparative example 4
A blue organic electroluminescent device was produced in the same manner as in example 1, except that compound TAZ was used instead of compound 8.
For the organic electroluminescent device prepared as above, the voltage, efficiency, and color coordinate were 10mA/cm at constant current density 2 The test is carried out, and the service life of the T95 device is 20mA/cm at constant current density 2 The following tests were carried out and the results are shown in Table 2.
Table 2 performance test results of blue organic electroluminescent device
Figure BDA0002456407460000392
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Figure BDA0002456407460000401
As can be seen from Table 2, in the device structure using the compound as an electron transport layer, the organic electroluminescent devices prepared in examples 1 to 16 were improved in various properties as compared with the comparative examples. Wherein, compared with the comparative example 1, the working voltage of the organic electroluminescent devices prepared in the examples 1 to 16 is reduced by 0.2 to 0.3V, the External Quantum Efficiency (EQE) is improved by 4 to 11 percent, the luminous efficiency is improved by 7.5 to 13 percent, and the service life is improved by 26 to 43 percent; compared with the comparative example 2, the working voltage of the organic electroluminescent devices prepared in the examples 1 to 16 is reduced by 0.3 to 0.39V, the External Quantum Efficiency (EQE) is improved by 1.6 to 13 percent, the luminous efficiency is improved by 11.6 to 15 percent, and the service life is improved by 31 to 50 percent; compared with the comparative example 3, the working voltage of the organic electroluminescent devices prepared in the examples 1 to 16 is reduced by 0.38 to 0.47V, the External Quantum Efficiency (EQE) is improved by 9 to 17 percent, the luminous efficiency is improved by 6.8 to 16 percent, and the service life is improved by 31 to 50 percent; compared with comparative example 4, the organic electroluminescent devices prepared in examples 1 to 16 have a reduced operating voltage of 0.43 to 0.52V, an improved External Quantum Efficiency (EQE) of 8 to 15.8%, an improved luminous efficiency of 5 to 12%, and an improved lifetime of at least 52.6 to 73%, and thus, low-voltage and long-life organic electroluminescent devices can be prepared using the nitrogen-containing compounds of the present application in the electron transport layer.
Example 17 example of manufacturing an organic light emitting diode in which a green phosphorescent compound and the material of the comparative example were used as a green host.
An organic light emitting diode was manufactured using the same manufacturing process as described above, except that the compound 3 was used as a host while doping GD at a weight ratio of 5% for an emission layer (EML). Adding Alq 3 And LiQ in a weight ratio of 1
Figure BDA0002456407460000402
Figure BDA0002456407460000403
A thick Electron Transport Layer (ETL), and LiQ is evaporated on the electron transport layer to form a thickness ^ H>
Figure BDA0002456407460000404
Then magnesium (Mg) and silver (Ag) were mixed at an evaporation rate of 1>
Figure BDA0002456407460000405
The cathode of (2).
Examples 18 to 22
Green organic electroluminescent devices were fabricated in the same manner as in example 17, using the corresponding compounds in table 3 in place of compound 3, and the properties of the fabricated devices are shown in table 3.
Comparative example 5
A green organic electroluminescent device was produced in the same manner as in example 17, using compound C in place of compound 3.
Comparative example 6
A green organic electroluminescent device was produced in the same manner as in example 17, using compound D in place of compound 3.
Comparative example 7
A green organic electroluminescent device was fabricated in the same manner as in example 17, using compound CBP instead of compound 3.
For the organic electroluminescent device prepared as above, the voltage, efficiency, and color coordinate were 10mA/cm at constant current density 2 The test is carried out, and the service life of the T95 device is 50mA/cm at constant current density 2 The following tests were carried out and the results are shown in Table 3.
TABLE 3 Performance test results of Green organic electroluminescent devices
Figure BDA0002456407460000411
As is apparent from Table 3, in the structure of the green host device using the compound, the organic electroluminescent devices prepared in examples 17 to 22 were improved in each performance as compared with the comparative example. Wherein, compared with the comparative example 5, the working voltage of the organic electroluminescent devices prepared in the examples 17 to 22 is reduced by 0.2 to 0.41V, the External Quantum Efficiency (EQE) is improved by 10 to 17 percent, the luminous efficiency is improved by 16 to 28 percent, and the service life is improved by 12 to 28 percent; compared with the comparative example 6, the working voltage of the organic electroluminescent devices prepared in the examples 17 to 22 is reduced by 0.13 to 0.34V, the External Quantum Efficiency (EQE) is improved by 8 to 19 percent, the luminous efficiency is improved by 15 to 27 percent, and the service life is improved by 19 to 31 percent; compared with comparative example 7, the working voltage of the organic electroluminescent devices prepared in examples 17 to 22 was reduced by 0.1 to 0.31V, the External Quantum Efficiency (EQE) was improved by 4 to 15%, the luminous efficiency was improved by 12 to 24%, and the lifetime was improved by 11 to 23%. Therefore, by using the nitrogen-containing compound of the present application in a green host, electron mobility is improved, and carrier transport is balanced, so that a low-voltage, high-luminous efficiency, long-life organic electroluminescent device can be obtained.
The nitrogen-containing compound provided by the application comprises an aromatic amine group, a triazine group, a carbazole group and an adamantine group, wherein the aromatic amine group and the carbazole group have excellent hole transmission capability, the triazine group has better electron transmission capability, the triazine group is combined with the carbazole group, a conjugated system is added, and a continuous pi conjugate ties up better electron mobility, so that the nitrogen-containing compound has high electron mobility to balance carrier transmission, and further improves the voltage characteristic and the efficiency characteristic of an electronic element applying the nitrogen-containing compound, such as the open-circuit voltage and the photoelectric efficiency of a photoelectric conversion device, the driving voltage of an organic electroluminescent device is reduced, and the luminous efficiency of the organic electroluminescent device is improved. The conjugation and electron transfer of different functional groups are effectively interrupted by utilizing the rigid non-conjugated structure of adamantane, so that the compound has an energy level more matched with that of an adjacent layer, and the prepared organic electroluminescent device has low driving voltage. In addition, the compound provided by the application introduces a triphenylamine group and an adamantine group to expand a molecular system on the basis of a common triazine derivative substituted by carbazole, so that the overall molecular weight and asymmetry are enhanced, and the film-forming property of the molecule is improved.
TABLE 4 calculated values of energy levels of nitrogen-containing compounds and compounds A, B
Figure BDA0002456407460000412
Figure BDA0002456407460000421
As can be seen from table 4, the nitrogen-containing compound of the present application has a higher triplet energy level compared with compound a and compound B, and when the nitrogen-containing compound of the present application is used in an electron transport layer of an organic electroluminescent device, the nitrogen-containing compound of the present application promotes efficient injection of electrons into a light emitting layer, which is beneficial to improving the emission efficiency and the service life of the organic electroluminescent device. In addition, in the nitrogen-containing compound molecule, HOMO and LUMO are distributed on different units, so that holes and electrons can be transferred on respective transmission units, a stable and uniform thin film can be formed in the preparation process of an electronic element, and the stability of the electronic element during operation is kept.
In summary, the method of the present application manufactures the phosphorescent compound having high triplet energy and uses the phosphorescent compound as a host of the light emitting layer of the organic light emitting diode, thereby promoting energy transfer in the light emitting layer and improving green light emission efficiency and lifespan of the organic light emitting layer.

Claims (7)

1. A nitrogen-containing compound, wherein the structural formula of the nitrogen-containing compound is shown in chemical formula 1:
Figure FDA0003975778110000011
wherein, L is 1 、L 2 Each independently selected from the group consisting of:
Figure FDA0003975778110000012
Ar 1 selected from the group consisting of:
Figure FDA0003975778110000013
/>
Figure FDA0003975778110000021
2. the nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0003975778110000022
/>
Figure FDA0003975778110000031
/>
Figure FDA0003975778110000041
/>
Figure FDA0003975778110000051
/>
Figure FDA0003975778110000061
/>
Figure FDA0003975778110000071
/>
Figure FDA0003975778110000081
/>
Figure FDA0003975778110000091
/>
Figure FDA0003975778110000101
/>
Figure FDA0003975778110000111
/>
Figure FDA0003975778110000121
3. 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 2.
4. The electronic component according to claim 3, wherein the functional layer comprises an electron transport layer comprising the nitrogen-containing compound.
5. The electronic element according to claim 3, wherein the functional layer comprises a light-emitting layer including a host material and a guest material;
the host material comprises the nitrogen-containing compound.
6. The electronic component according to any one of claims 3 to 5, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
7. An electronic device, characterized by comprising the electronic component according to any one of claims 3 to 6.
CN202010307832.3A 2020-04-17 2020-04-17 Nitrogen-containing compound, electronic component, and electronic device Active CN112812102B (en)

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