CN111518017B - Nitrogen-containing compound, electronic component, and electronic device - Google Patents

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

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CN111518017B
CN111518017B CN202010478505.4A CN202010478505A CN111518017B CN 111518017 B CN111518017 B CN 111518017B CN 202010478505 A CN202010478505 A CN 202010478505A CN 111518017 B CN111518017 B CN 111518017B
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CN111518017A (en
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聂齐齐
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application belongs to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic element and an electronic device. The structure of the nitrogen-containing compound is shown in chemical formula 1, and the nitrogen-containing compound can improve the performance of an electronic element.
Figure DDA0002516526490000011

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.
At present, when the organic electroluminescent device is driven at high temperature, the problems of working voltage rise, luminous efficiency reduction, service life shortening and the like occur, so that the performance of the organic electroluminescent device is reduced. Patent documents such as CN109836338A and JP2007077064A disclose that compounds containing an adamantyl group can be used for the hole transport layer. However, the performance of the existing hole transport layer materials is yet to be further improved.
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 structure represented by chemical formula 1:
Figure BDA0002516526470000011
wherein Ar is1Selected from the following substituted or unsubstituted groups: arylene having 6 to 30 carbon atomsA heteroarylene group having 3 to 30 carbon atoms;
Ar2and Ar3Each independently 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 3-30 carbon atoms;
Ar4and Ar5Independently selected from deuterium, halogen, cyano, heteroaryl with 3-18 carbon atoms, aryl with 6-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, arylsilyl with 8-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylthio with 6-18 carbon atoms and phosphorus oxy with 6-18 carbon atoms;
a is selected from 0, 1,2, 3 or 4, when a is more than or equal to 2, any two Ar4The same or different;
b is selected from 0, 1,2, 3 or 4, when b is more than or equal to 2, any two Ar5The same or different.
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 another 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. 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.
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 subject matter of the present 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 BDA0002516526470000031
wherein Ar is1Selected from the following substituted or unsubstituted groups: arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms;
Ar2and Ar3Each independently 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 3-30 carbon atoms;
Ar4and Ar5Independently selected from deuterium, halogen, cyano, heteroaryl with 3-18 carbon atoms, aryl with 6-18 carbon atoms, trialkylsilyl with 3-12 carbon atoms, arylsilyl with 8-12 carbon atoms, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, alkenyl with 2-6 carbon atoms, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkenyl with 5-10 carbon atoms, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms, arylthio with 6-18 carbon atoms and phosphorus oxy with 6-18 carbon atoms;
a is selected from 0, 1,2, 3 or 4, when a is more than or equal to 2, any two Ar4The same or different;
b is selected from 0, 1,2, 3 or 4, when b is more than or equal to 2, any two Ar5The same or different.
According to the nitrogen-containing compound, an adamantyl structure is introduced on an aryl group of triarylamine, the electron cloud density of a conjugated system of the triarylamine compound is improved through a super-conjugated effect, and further the hole conductivity and the electron tolerance of the nitrogen-containing compound can be enhanced, so that the voltage characteristic and the efficiency characteristic of an electronic element applying the nitrogen-containing compound can be improved, for example, the open-circuit voltage and the photoelectric efficiency of a photoelectric conversion device are improved, the driving voltage of an organic electroluminescent device is reduced, the luminous efficiency of the organic electroluminescent device is improved, and the like. The adamantyl is in spiro union with the substituted or unsubstituted fluorenyl, so that both sides of the adamantyl are in aromatic ring structures, and the adamantyl can be simultaneously protected by aryl groups on both sides, so that the dehydrogenation reaction of the adamantyl at high temperature can be inhibited, the stability of the nitrogen-containing compound can be improved, and the service life of an electronic element using the nitrogen-containing compound can be improved, such as the service life of a photoelectric conversion device and an organic electroluminescent device. Furthermore, since the nitrogen-containing compound is more stable at high temperatures, it has better thermal stability when used in mass production of electronic components, and can improve the uniformity of mass production of electronic components.
Moreover, the introduced adamantyl has larger steric hindrance and a rigid structure, and meanwhile, the non-conjugated molecular structure of the adamantyl does not influence the electronic energy level of the triarylamine group, so that the hole transport performance of the nitrogen-containing compound is ensured, the molecular weight of the compound can be increased, the molecular symmetry can be reduced, the glass transition temperature and the evaporation temperature of the nitrogen-containing compound can be increased, the crystallinity of the nitrogen-containing compound can be controlled, the compound has good physical and thermal stability, and the mass production stability of an organic electroluminescent device and a photoelectric conversion device is further improved.
Optionally, the Ar is1、Ar2And Ar3The substituents on the above groups are the same or different and are each independently selected from: deuterium, halogen, cyano, heteroaryl having 3 to 30 carbon atoms, aryl having 6 to 30 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkyl having 2 to 10 carbon atoms5 to 10 cycloalkenyl groups, 4 to 10 heterocycloalkenyl groups, 1 to 10 alkoxy groups, 1 to 10 alkylthio groups, 6 to 18 aryloxy groups, 6 to 18 arylthio groups, and 6 to 18 phosphonoxy groups.
Further optionally, the Ar1、Ar2And Ar3The substituent(s) is deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or alkyl having 1 to 5 carbon atoms.
In the context of the present application, it is,
Figure BDA0002516526470000041
represents a chemical bond.
In the present application, since adamantane is a three-dimensional structure, in the structure diagram of the compound, since drawing angles are different, planar shapes are different, and the cyclic structures formed on 9, 9-dimethylfluorene are all adamantane, and the connecting positions are also the same. For example:
Figure BDA0002516526470000042
all have the same structure.
In this application, Ar1、Ar2、Ar3And Ar4、Ar5The number of carbon atoms of (b) means all the number of carbon atoms. For example, if Ar1Selected from the group consisting of substituted arylene groups having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12.
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 or the like 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, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 20 carbon atoms, and numerical ranges such as "1 to 20" refer herein to each integer in the given range; for example, "1 to 20 carbon atoms" refers to an alkyl group that may contain 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 6 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. An alkenyl group 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 may contain 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, a numerical range such as "3 to 20" refers to each integer in the given range; for example, "3 to 20 carbon atoms" refers to a cycloalkyl group that can contain 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, or 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 10 carbon atoms, and specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantyl.
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 as an aryl group in the present application. Wherein the aryl group does not contain a heteroatom 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, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, hexabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
Figure BDA0002516526470000052
a phenyl group, a fluorenyl group, and the like, without being limited thereto.
In this application, substituted aryl refers to an aryl group 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, hydroxyl, amino, branched alkyl, straight chain alkyl, cycloalkyl, alkoxy, alkylamino, alkylthio, 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 25, and the number of carbon atoms of the 9, 9-diphenylfluorenyl group and the spirobifluorenyl group are both 25. Among them, biphenyl can be interpreted as an aryl group or a substituted phenyl group.
In the present application, the aryl group having 6 to 25 ring-forming carbon atoms means that the number of carbon atoms located on the aromatic ring in the aryl group is 6 to 25, and the number of carbon atoms in the substituent on the aryl group is not counted. The number of the ring-forming carbon atoms in the aryl group may be 6, 10, 12, 15, 18, 20 or 25, but is not limited thereto.
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 BDA0002516526470000051
in the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si and S as a heteroatom. 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, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl, phenyl-substituted dibenzofuryl, Dibenzofuranyl-substituted phenyl groups, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
In the present application, the heteroaryl group having 5 to 25 ring-forming carbon atoms means that the number of carbon atoms located on the heteroaryl ring in the heteroaryl group is 5 to 24, and the number of carbon atoms in the substituent on the heteroaryl group is not counted. The number of ring-forming carbon atoms on the heteroaryl group may be 5, 8, 12, 18, 20, 24, but is not limited thereto.
In this application, the explanation for aryl is applicable to arylene, and the explanation for heteroaryl is also applicable to heteroarylene.
In the present application, halogen may be fluorine, chlorine, bromine, iodine.
The descriptions used in this application that "… … independently" and "… … independently" and "… … independently selected from" are interchangeable and should be understood in a broad sense to mean that the particular items expressed between the same symbols do not interfere with each other in different groups or that the particular items expressed between the same symbols do not interfere with each other in the same groups.
For example: in "
Figure BDA0002516526470000061
Wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents 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 with each other.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002516526470000062
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 the following formula (X), naphthyl represented by the formula (X) is connected to 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 (X-1) to the formula (X-7) includes any possible connecting mode shown in the formula (X-1).
Figure BDA0002516526470000063
For example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is bonded to the rest 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 the formulas (X '-1) to (X' -4).
Figure BDA0002516526470000064
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, in the following formula (Y), the substituent R group 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 shown by the formulas (Y-1) to (Y-7).
Figure BDA0002516526470000071
According to one embodiment, Ar1Selected from the following substituted or unsubstituted groups: arylene having 6 to 25 ring-forming carbon atoms, ring-forming carbonHeteroarylene having 5 to 20 atoms.
According to another embodiment, Ar1Is selected from substituted or unsubstituted arylene with 6-25 carbon atoms and substituted or unsubstituted heteroarylene with 5-20 carbon atoms. Alternatively, Ar1Is selected from substituted or unsubstituted arylene with 6-15 carbon atoms and substituted or unsubstituted heteroarylene with 5-18 carbon atoms.
Alternatively, Ar1The substituent(s) is (are) deuterium, halogen, cyano, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, or pyridyl. Ar (Ar)1The substituent(s) may be selected from, for example, deuterium, fluorine, cyano, phenyl, naphthyl, biphenyl, pyridyl, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl.
According to a particular embodiment, Ar1Selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene. According to another specific embodiment, Ar1Selected from the group consisting of substituted or unsubstituted dimethylfluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted N-phenylcarbazolyl.
In some embodiments, Ar1Selected from the group consisting of groups represented by the following formulae j-1 to j-13:
Figure BDA0002516526470000072
Figure BDA0002516526470000081
wherein M is2Selected from a single bond or
Figure BDA0002516526470000082
Q1～Q5Each independently selected fromN or C (F)5) And Q is1～Q5At least one is selected from N; when Q is1～Q5Two or more of C (F)5) When, two arbitrary F5The same or different;
Q6～Q13each independently selected from N or C (F)6) And Q is6～Q13At least one is selected from N; when Q is6～Q13Two or more of C (F)6) When, two arbitrary F6The same or different;
Q14～Q23each independently selected from N or C (F)7) And Q is14～Q23At least one is selected from N; when Q is14～Q23Two or more of C (F)7) When, two arbitrary F7The same or different;
Q24～Q33each independently selected from N or C (F)8) And Q is24～Q33At least one is selected from N; when Q is24～Q33Two or more of C (F)8) When, two arbitrary F8The same or different;
E1～E14、F5～F8each independently selected from: deuterium, halogen, cyano, heteroaryl having 3 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, and phosphonoxy having 6 to 18 carbon atoms;
F5～F8any of which may also be independently selected from hydrogen;
erto getSubstituent ErR is any integer of 1-14; when r is selected from 1,2, 3,4, 5, 6, 9, 13 or 14, erSelected from 0, 1,2, 3 or 4; when r is selected from 7 or 11, erSelected from 0, 1,2, 3,4, 5 or 6; when r is 12, erSelected from 0, 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 0, 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)15)、C(E16E17)、Si(E16E17) (ii) a Wherein E is15、E16、E17Each 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, 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 E16And E17Atoms that are linked to each other to be commonly bound to them form a ring;
K4selected from the group consisting of a single bond, O, S, Se, N (E)18)、C(E19E20)、Si(E19E20) (ii) a Wherein E is18、E19、E20Each 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, 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 E19And E20The atoms that are linked to each other to be commonly linked to them form a ring.
In this application, E16And E17Can be independent of each other and are not directly connected; or E16And E17May be directly attached, forming a ring with the atoms that are attached in common, for example: it is possible to form a ring having 3 to 15 carbon atoms, and also, for example, to formA ring having 3 to 10 carbon atoms; the ring may be saturated (e.g., five-membered ring, six-membered ring, adamantane, etc.) or unsaturated, e.g., aromatic. That is, E16And E17The substituents may be independent of each other or may be linked to each other to form a cyclic group, and specific examples of the cyclic group that may be formed include, but are not limited to: cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane. This explanation applies equally to E19And E20。
Alternatively, Ar1Selected from the group consisting of:
Figure BDA0002516526470000091
Figure BDA0002516526470000101
further optionally, Ar1Selected from the group consisting of:
Figure BDA0002516526470000102
Figure BDA0002516526470000111
according to one embodiment, Ar2And Ar3Each independently selected from the following substituted or unsubstituted groups: an aryl group having 6 to 25 ring-forming carbon atoms and a heteroaryl group having 3 to 25 ring-forming carbon atoms.
According to another embodiment, Ar2And Ar3Each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 24 carbon atoms.
Alternatively, Ar2And Ar3The substituents are independently selected from deuterium, halogen, cyano, aryl with 6-20 carbon atoms, and aryl with 6-20 carbon atoms4-20 heteroaryl, C1-5 alkyl, and C3-10 cycloalkyl. Ar (Ar)2And Ar3The substituents of (a) may be, for example, independently selected from deuterium, fluorine, cyano, phenyl, naphthyl, biphenyl, dimethylfluorenyl, triphenylene, methyl, ethyl, propyl, isopropyl, tert-butyl, pyridyl, quinolyl, pyrimidinyl, phenanthrolinyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, etc.
In some embodiments, Ar2And Ar3Selected from the group consisting of groups represented by the following chemical formula i-1 to chemical formula i-15:
Figure BDA0002516526470000112
Figure BDA0002516526470000121
wherein M is1Selected from a single bond or
Figure BDA0002516526470000122
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 F3Same orDifferent;
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;
H1～H21、F1～F4each independently selected from: deuterium, halogen, cyano, heteroaryl having 3 to 18 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, arylsilyl having 8 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkenyl having 2 to 6 carbon atoms, alkynyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, cycloalkenyl having 5 to 10 carbon atoms, heterocycloalkenyl having 4 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, and phosphonoxy having 6 to 18 carbon atoms;
H4～H20any one of the aryl groups can be independently selected from aryl groups with 6-18 carbon atoms, wherein the aryl groups are optionally substituted by deuterium, fluorine, chlorine or cyano; the expression "aryl group optionally substituted with deuterium, fluorine, chlorine or cyano group having 6 to 18 carbon atoms" as used herein means that the aryl group may be substituted with one or more of deuterium, fluorine, chlorine or cyano group, or may not be substituted with deuterium, fluorine, chlorine or cyano group.
F1～F4Any one of the above groups can be independently selected from hydrogen and aryl with 6-18 carbon atoms;
hkis a substituent HkK is any integer of 1-21; 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 0, 1,2, 3 or 4; when k is selected from 1,3, 4, 6, 9 or 14, hkSelected from 0, 1,2, 3,4 or 5; when k is 13, hkSelected from 0, 1,2, 3,4, 5 or 6; when k is selected from 10 or 19When h is presentkSelected from 0, 1,2, 3,4, 5, 6 or 7; when k is selected from 20, hkSelected from 0, 1,2, 3,4, 5, 6, 7 or 8; when k is 11, hkSelected from 0, 1,2, 3,4, 5, 6, 7, 8 or 9;
when h is generatedkWhen greater than 1, any two HkThe same or different;
K1selected from O, S, Se, N (H)22)、C(H23H24)、Si(H23H24) (ii) a Wherein H22、H23、H24Each 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, 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 the above H23And H24Atoms that are linked to each other to be commonly bound to them form a ring;
K2selected from single bond, O, S, Se, N (H)25)、C(H26H27)、Si(H26H27)；
Wherein H25、H26、H27Each 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, 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 the above H26And H27The atoms that are linked to each other to be commonly linked to them form a ring.
Alternatively, in some embodiments of the compounds described herein, H23And H24Are independent of each other and are not directly connected; or H23And H24Directly attached, with the atoms commonly attached forming a ring, for example: a ring having 3 to 15 carbon atoms may be formed, and for example, a ring having 3 to 10 carbon atoms may be formed; the ring may be saturatedAnd (e.g., five-membered rings, six-membered rings, adamantane, etc.), and may also be unsaturated, such as aromatic rings. That is, H23And H24The substituents may be independent of each other or may be linked to each other to form a cyclic group, and specific examples of the cyclic group that may be formed include, but are not limited to: cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane. This explanation applies equally to H26And H27。
Alternatively, Ar2And Ar3Each independently selected from the group consisting of:
Figure BDA0002516526470000131
Figure BDA0002516526470000141
Figure BDA0002516526470000151
further optionally, Ar2And Ar3Each independently selected from the group consisting of:
Figure BDA0002516526470000152
Figure BDA0002516526470000161
optionally, the nitrogen-containing compound is selected from the group formed by:
Figure BDA0002516526470000171
Figure BDA0002516526470000181
Figure BDA0002516526470000191
Figure BDA0002516526470000201
Figure BDA0002516526470000211
Figure BDA0002516526470000221
Figure BDA0002516526470000231
Figure BDA0002516526470000241
Figure BDA0002516526470000251
Figure BDA0002516526470000261
Figure BDA0002516526470000271
Figure BDA0002516526470000281
Figure BDA0002516526470000291
Figure BDA0002516526470000301
Figure BDA0002516526470000311
Figure BDA0002516526470000321
Figure BDA0002516526470000331
Figure BDA0002516526470000341
Figure BDA0002516526470000351
Figure BDA0002516526470000361
Figure BDA0002516526470000371
Figure BDA0002516526470000381
Figure BDA0002516526470000391
Figure BDA0002516526470000401
Figure BDA0002516526470000411
Figure BDA0002516526470000421
Figure BDA0002516526470000431
Figure BDA0002516526470000441
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.
According to one embodiment, 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 a hole transport layer 321, the hole transport layer 321 comprising a nitrogen-containing compound as provided herein. The hole transport layer 321 may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
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 hole transport layer 321 of the organic electroluminescent device, can effectively improve the luminous efficiency, the service life and the thermal stability of the organic electroluminescent device, and can reduce 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 SnO2Sb; 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.
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 electroluminescent layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic electroluminescent layer 330 may be composed of a host material and a guest material, and a hole injected into the organic electroluminescent layer 330 and an electron injected into the organic electroluminescent layer 330 may be combined in the organic electroluminescent layer 330 to form an exciton, and the exciton transfers 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 electroluminescent 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 electroluminescent layer 330 may be 4,4'-N, N' -dicarbazole-biphenyl (abbreviated as "CBP").
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic electroluminescent layer 330 may be Ir (piq)2(acac)。
Alternatively, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, the electron transport layer 350 may be composed of TPBi and LiQ.
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, 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 BaF2But not limited thereto,/Ca. Preferably, a metal electrode comprising silver and magnesium 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 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 HAT-CN.
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.
Optionally, a hole blocking layer 340 may be further disposed between the organic electroluminescent layer 330 and the electron transport layer 350.
According to another embodiment, the electronic component may be a photoelectric conversion device, as shown in fig. 2, which 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.
Alternatively, the functional layer 300 includes a hole transport layer 321, the hole transport layer 321 comprising a nitrogen-containing compound as provided herein. The hole transport layer 321 may be composed of the nitrogen-containing compound provided herein, or may be composed 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 hole transport layer 321 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 hole transport layer 321 includes the nitrogen-containing compound of the present application.
The application also provides an electronic device which comprises the electronic element. 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.
According to one embodiment, as shown in fig. 3, the electronic device is a first electronic device 400 comprising the above-described organic electroluminescent device. The electronic device may be 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. Since the first electronic device 400 has the organic electroluminescent device, the same advantages are obtained, and the description of the present application is omitted.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, which includes the above-described 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 second electronic device 500 has the above-mentioned photoelectric conversion device, the same beneficial effects are obtained, and the description of the application is omitted here.
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
Compounds were synthesized by the following synthetic route.
Figure BDA0002516526470000461
Synthesis of Compound 1:
Figure BDA0002516526470000462
magnesium strips (13.54g,564mmol) and diethyl ether (100mL) were placed in a dry round bottom flask under nitrogen and iodine (100mg) was added. Then, slowly dripping the solution of 2-bromobiphenyl (50.00g,214.5mmol) dissolved in diethyl ether (200mL) into the flask, heating to 35 ℃ after finishing dripping, and stirring for 3 hours; cooling the reaction solution to 0 ℃, slowly dropping an ether (200mL) solution dissolved with 5-hydroxy-2-adamantanone (24.76g, 149mmol), heating to 35 ℃ after dropping, and stirring for 6 hours; cooling the reaction solution to room temperature, adding 5% hydrochloric acid to the reaction solution until the pH value is less than 7, stirring the solution for 1 hour, adding diethyl ether (200mL) to the solution for extraction, combining organic phases, drying the organic phases by using anhydrous magnesium sulfate, filtering the mixture, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using ethyl acetate/n-heptane (1:2) as the mobile phase to give intermediate I-A-1(43g, yield 90%) as a white solid.
Figure BDA0002516526470000471
Adding intermediate I-A-1(43g,134.2mmol), trifluoroacetic acid (36.93g,380.6mmol) and dichloromethane (300mL) into a round-bottom flask, and stirring under nitrogen for 2 hours; then, an aqueous sodium hydroxide solution was added to the reaction mixture until the pH became 8, followed by liquid separation, drying of the organic phase with anhydrous magnesium sulfate, filtration, and removal of the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:2) to give intermediate I-A-2(39.2g, yield 96.6%)
Figure BDA0002516526470000472
Adding the intermediate I-A-2(20g,65mmol), phenol (5.7g,61.4mmol) and dichloromethane (150mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding concentrated sulfuric acid (12.0g,123.3mmol) at-10 ℃ to 5 ℃, and stirring for 3 hours under the condition of heat preservation; then, an aqueous sodium hydroxide solution was added to the reaction mixture until the pH became 8, followed by liquid separation, drying of the organic phase with anhydrous magnesium sulfate, filtration, and removal of the solvent under reduced pressure; the crude product was purified by recrystallization from ethanol to give intermediate I-A-3 as a white solid (15.5g, yield 63%).
The same procedure was used to synthesize the intermediates shown in the second column in table 1 below, substituting phenol with starting material 1 in the first column in table 1 below:
table 1 starting materials and intermediates
Figure BDA0002516526470000473
Figure BDA0002516526470000481
Figure BDA0002516526470000482
Adding the intermediate I-A-3(15.5g,40.9mmol), pyridine (6.2g,78mmol) and dichloromethane (150mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding trifluoromethanesulfonic anhydride (11.0g,39mmol) at-10 ℃ to-5 ℃, and stirring for 3 hours under the condition of heat preservation; then, the reaction solution was washed with dilute hydrochloric acid until the pH was 8, separated, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by column chromatography on silica gel using dichloromethane/n-heptane (1:2) to give intermediate I-A as a white solid (18g, yield 90.4%).
Intermediates I-a-3 were substituted with the intermediates in the first column of table 2 below and the same procedure was used to synthesize the intermediates shown in the second column of table 2 below:
table 2 intermediate synthesis
Figure BDA0002516526470000483
Figure BDA0002516526470000491
Adding the intermediate I-A (2.5g,4.9mmol), 4-aminobiphenyl (1.8g,10.63mmol), tris (dibenzylideneacetone) dipalladium (0.1g, 0.15mmol), 2-dicyclohexylphosphonium-2 ', 4', 6 ' -triisopropylbiphenyl (0.10g,0.21mmol) and sodium tert-butoxide (1.52g, 16.09mmol) into toluene (40mL), heating to 108 ℃ under nitrogen protection, stirring for 2 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 using a dichloromethane/ethyl acetate system to afford intermediate I-B as a pale yellow solid (2.08g, yield 80.25%).
Figure BDA0002516526470000492
Adding the intermediate I-B (2.85g,5.38mmol), 4-bromobiphenyl (1.25g,5.38mmol), tris (dibenzylideneacetone) dipalladium (0.05g,0.05mmol), 2-dicyclohexyl-phosphorus-2 ', 6' -dimethoxybiphenyl (0.04g,0.11mmol) and sodium tert-butoxide (0.78g, 8.07mmol) into toluene (30mL), heating to 108 ℃ under nitrogen 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 compound 1 as a white solid (2.35g, yield 64%). Mass spectrum: 682.3[ M + H ] M/z]+
Nuclear magnetic data for compound 1:
1HNMR(400MHZ，CD2Cl2)8.04(d,2H),7.70-7.65(m,4H),7.59-7.40(m,16H),7.35(d,2H),7.31-7.23(m,6H),2.53(d,2H),2.42(d,2H),1.99-1.60(m,9H)。
the same procedure was used to synthesize the compounds shown in the third column in table 3 below, substituting intermediate I-a with the intermediate in the second column in table 3 below:
TABLE 3 intermediates and Compounds
Figure BDA0002516526470000493
Figure BDA0002516526470000501
The compounds shown in the fourth column in Table 4 were synthesized in the same manner as in Compound 1 except that the second column in Table 4 below was used as starting material 2 instead of 4-aminobiphenyl, and the third column in Table 4 below was used as starting material 3 instead of 4-bromobiphenyl. Specific compound numbers, structures, starting materials, synthesis yields for the last step, characterization data, etc. are shown in table 4.
Table 4: compound structure, preparation and characterization data
Figure BDA0002516526470000502
Figure BDA0002516526470000511
Figure BDA0002516526470000521
Figure BDA0002516526470000531
Adding the intermediate I-A (80.0 g; 156.8mmol), 2-bromobenzoic acid (36.5 g; 181.7mmol), tetrakis (triphenylphosphine) palladium (6.9 g; 6.0mmol), potassium carbonate (103.2 g; 746.7mmol), tetrabutylammonium bromide (19.2 g; 59.7mmol) into a flask, adding a mixed solvent of toluene (600mL), ethanol (150mL) and water (150mL), heating to 80 ℃ under the protection of nitrogen, keeping the temperature, and stirring for 18 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using methylene chloride/n-heptane as the mobile phase crude gave the intermediate I-A-5(42.0 g; yield 52%)
Figure BDA0002516526470000532
Reacting intermediate I-A-5(5.7g,11mmol),Diphenylamine (1.86g,11mmol), tris (dibenzylideneacetone) dipalladium (0.1g,0.1mmol), 2-dicyclohexylphosphonium-2 ', 6' -dimethoxybiphenyl (0.08g,0.12mmol) and sodium tert-butoxide (0.78g, 8.07mmol) were added to toluene (50mL), heated to 108 ℃ under nitrogen and stirred 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 to give compound 344 as a white solid (5.8g, 87% yield). Mass spectrum: 606.3[ M + H ] M/z]+
Nuclear magnetic data for compound 344:
1HNMR(400MHz，CD2Cl2)8.03(d,2H),7.70(d,2H),7.7.63-7.31(m,15H),7.26-7.17(m,3H),6.95(d,4H),2.49-2.38(m,4H),1.92-1.61(m,9H).
Figure BDA0002516526470000533
adding the intermediate I-A-2(10g,33mmol), o-bromophenol (5.45g,31.5mmol) and dichloromethane (100mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding concentrated sulfuric acid (6.18g,62.99mmol) at-10 ℃ to-5 ℃, and keeping the temperature and stirring for 3 hours; then, an aqueous sodium hydroxide solution was added to the reaction mixture until the pH became 8, followed by liquid separation, drying of the organic phase with anhydrous magnesium sulfate, filtration, and removal of the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (1:3) to give intermediate I-A-4 as a white solid (10.7g, yield 74.3%).
Figure BDA0002516526470000541
I-A-4(10.7g, 23.39mmol), phenylboronic acid (2.85g, 23.39mmol), tetrakis (triphenylphosphine) palladium (0.54g, 0.47mmol), potassium carbonate (7.1g,51.46mmol), tetrabutylammonium chloride (1.3g,4.68mmol), toluene (80mL), ethanol (20mL), and deionized water (20mL) were added to a three-necked flask, warmed to 75 ℃ to 80 ℃ under nitrogen, heated to reflux, and stirred for 8 h. After the reaction is finished, cooling the solution to room temperature, adding toluene and (100mL) 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 column chromatography on silica gel to give intermediate I-A-51 as a solid (9.1g, yield 85.6%).
Figure BDA0002516526470000542
Adding the intermediate I-A-51(9.1g,20.0mmol), pyridine (4.75g,60.05mmol) and dichloromethane (100mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding trifluoromethanesulfonic anhydride (6.78g, 24.02mmol) at-10 ℃ to-5 ℃, and stirring for 3 hours under the condition of heat preservation; then, the reaction solution was washed with dilute hydrochloric acid until the pH was 8, separated, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane (1:2) to give intermediate I-A-6 as a white solid (10g, yield 85.5%).
The compounds in the fourth column in table 5 were synthesized using the same synthesis method as compound 1 except that intermediate I-a-6 was used instead of intermediate I-a, the second column of raw material in table 5 was used instead of 4-aminobiphenyl as raw material 2, and the third column of raw material in table 5 was used instead of 4-bromobiphenyl raw material 3.
Table 5: compound number, structure, preparation and characterization data
Figure BDA0002516526470000543
Figure BDA0002516526470000551
Figure BDA0002516526470000552
Adding the intermediate I-A-2(9g,29.8mmol), p-hydroxybiphenyl (4.82g,28.34mmol) and dichloromethane (100mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding concentrated sulfuric acid (5.6g,56.69mmol) at-10 ℃ to-5 ℃, and stirring for 3 hours under the condition of heat preservation; then, an aqueous sodium hydroxide solution was added to the reaction mixture until the pH became 8, followed by liquid separation, drying of the organic phase with anhydrous magnesium sulfate, filtration, and removal of the solvent under reduced pressure; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane (1:2) to give intermediate I-A-7 as a white solid (11.4g, yield 88.5%).
Figure BDA0002516526470000553
Adding the intermediate I-A-7(11.4g,25.1mmol), pyridine (5.95g,75.23mmol) and dichloromethane (100mL) into a round-bottom flask, cooling to-10 ℃ under the protection of nitrogen, slowly dropwise adding trifluoromethanesulfonic anhydride (8.49g,30.09mmol) at-10 ℃ to-5 ℃, and stirring for 3 hours under the condition of heat preservation; then, the reaction solution was washed with dilute hydrochloric acid until the pH was 8, separated, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane (1:2) to give intermediate I-A-8 as a white solid (12.3g, yield 83.7%).
The compounds in table 6 were synthesized using the same synthesis method as compound 1, except that intermediate I-a-8 was used instead of intermediate I-a, the second column of raw material in table 6 below was used instead of 4-aminobiphenyl as raw material 2, the third column of raw material in table 6 below was used instead of 4-bromobiphenyl as raw material 3.
Table 6: compound number, structure, preparation and characterization data
Figure BDA0002516526470000561
Synthesis of compound 525:
Figure BDA0002516526470000562
synthesis of Compound 52 Using 4-bromobenzonitrile instead of 4-bromobiphenyl as starting Material 3 with reference to the Synthesis method of Compound 15. Mass spectrum: 631.3[ M + H ] M/z]+。
Synthesis of compound 526:
Figure BDA0002516526470000563
compound 526 was synthesized according to the synthesis method of compound 1 using 5-bromo-2-fluorotoluene instead of 4-bromobiphenyl as raw material 3. Mass spectrum: 638.3[ M + H ] M/z]+。
Synthesis of compound 527:
Figure BDA0002516526470000571
compound 527 was synthesized according to the synthesis method of compound 1, using 4-tert-butylbromobenzene instead of 4-bromobiphenyl as raw material 3. Mass spectrum: 662.4[ M + H ] M/z]+。
Synthesis of compound 528:
Figure BDA0002516526470000572
intermediate I-A-9 was synthesized using 2, 3-xylenol instead of p-hydroxybiphenyl as starting material 4, according to the synthetic method for intermediate I-A-8.
Figure BDA0002516526470000573
Compound 528 was synthesized according to the synthesis method for compound 1, using intermediate I-a-9 instead of intermediate I-a. Mass spectrum: 710.4[ M + H ] M/z]+。
Preparation and evaluation of organic electroluminescent device
Example 1 organic electroluminescent element using compound 1 as a Hole Transport Layer (HTL) material
An organic electroluminescent element was prepared by the following procedure: cutting a substrate containing an Ag alloy light reflecting layer and an anode ITO (thickness: 15nm) of an organic electroluminescent elementCutting into size of 40mm × 40mm × 0.7mm, performing photolithography to prepare experimental substrate with cathode, anode and insulating layer patterns, and treating with ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
The HAT-CN compound was vacuum-deposited on the test substrate (anode) to a thickness of
Figure BDA0002516526470000574
A Hole Injection Layer (HIL); followed by vacuum evaporation of a compound 1 over the hole injection layer to a thickness of
Figure BDA0002516526470000575
A Hole Transport Layer (HTL).
A compound TCTA as an Electron Blocking Layer (EBL) is evaporated on the Hole Transport Layer (HTL) to a thickness of
Figure BDA0002516526470000576
Depositing a compound 4,4'-N, N' -dicarbazole-biphenyl (CBP) as a main body on an Electron Blocking Layer (EBL) by vapor deposition, and doping 3 wt% of Ir (piq)2(acac) to a thickness of
Figure BDA0002516526470000577
The organic light emitting layer (EML).
The ratio of evaporation plating on the organic light emitting layer (EML) was 1: TPBi and LiQ are doped as an Electron Transport Layer (ETL) in a weight ratio of 1 and in a thickness of
Figure BDA0002516526470000581
Silver (Ag) and magnesium (Mg) are doped on the Electron Transport Layer (ETL) in a weight ratio of 10:1 as a cathode (cathode) and the thickness is
Figure BDA0002516526470000582
The cathode (cathode) is vapor-deposited with a compound CP-1 as an organic capping layer (CPL) to a thickness of
Figure BDA0002516526470000583
The evaporated devices were encapsulated with uv curable resin in a nitrogen glove box (water, oxygen content is strictly controlled).
Figure BDA0002516526470000584
Examples 2 to 30
In the above-described device structure, the organic electroluminescent device was fabricated by the same fabrication process as in example 1, except that compound 1 of the Hole Transport Layer (HTL) was replaced with the compound shown in table 7 below.
Comparative examples 1 to 4
In comparative examples 1 to 4, organic electroluminescent devices were fabricated in the same manner as in example 1, except that compound a, compound B, compound C and compound D were used as the hole transport layer instead of compound 1. The structures of compound a, compound B, compound C and compound D are shown below:
Figure BDA0002516526470000591
namely: comparative example 1 an organic electroluminescent device was fabricated using compound a, comparative example 2 an organic electroluminescent device was fabricated using compound B, comparative example 3 an organic electroluminescent device was fabricated using compound C, and comparative example 4 an organic electroluminescent device was fabricated using compound D, and device properties are shown in table 7 below.
Wherein the IVL (Current, Voltage, Brightness) data contrast is at 10mA/cm2As a result of the test under, T95 life was 15mA/cm2The test results at current density are shown in table 7.
Table 7 performance test results of organic electroluminescent device
Figure BDA0002516526470000592
Figure BDA0002516526470000601
Referring to the results of table 7, the organic electroluminescent devices prepared in examples 1 to 30 generally had high efficiency and long life characteristics compared to comparative examples 1,2, 3 and 4 in the case where CIEx was not much different in color coordinates.
From the results of table 7 above, it can be seen that the organic electroluminescent devices obtained in examples 1 to 30 have improved luminous efficiency and device lifetime compared to comparative examples 1,2, 3 and 4. The luminous efficiency of the organic electroluminescent device in the embodiment 3 can be as high as 36.9Cd/A, and is improved by nearly 62% compared with the luminous efficiency 22.9Cd/A of the comparative example 2; and the life of the organic electroluminescent device T95 of example 2 is 41% longer than that of comparative example 2.
In summary, the material of the present application is applied to a Hole Transport Layer (HTL) of an organic electroluminescent device, which contributes to the efficiency improvement and the lifetime extension of the organic electroluminescent device.
The organic electroluminescent devices prepared in example 1 were divided into two groups, one of which was directly subjected to a performance test without heat treatment, and the test results are shown in table 8. The other group was subjected to a heat treatment (standing at 110 ℃ C. for 1 hour) and then to a performance test, the results of which are shown in Table 9. With reference to the above-mentioned methods, the performance parameters of the organic electroluminescent devices prepared in example 12, example 19, comparative example 1, comparative example 2, comparative example 3 and comparative example 4 without heat treatment and the performance parameters after heat treatment were obtained, respectively.
TABLE 8 Performance parameters of organic light emitting devices without Heat treatment
Figure BDA0002516526470000611
TABLE 9 Performance parameters of the organic light emitting device after Heat treatment
Figure BDA0002516526470000612
From the results of tables 8 and 9, it is understood that the life of the organic electroluminescent device fabricated using the comparative example compound is significantly reduced by approximately 50%, whereas the organic electroluminescent device fabricated using the compound of the present application has substantially unchanged performance after heat treatment due to excellent thermal stability.
As can be seen from tables 7 to 9 of the results of the organic electroluminescent elements of the above examples, when an arylamine compound having an adamantane-fluorene core was used as a hole transport material, it was possible to produce an organic electroluminescent element having high efficiency, high heat resistance, and long life, which is excellent in characteristics such as driving voltage, light emission efficiency, external quantum efficiency, and thermal stability.
According to the nitrogen-containing compound, an adamantyl structure is introduced on an aryl group of triarylamine, the electron cloud density of a conjugated system of the triarylamine compound is improved through a super-conjugated effect, and further the hole conductivity and the electron tolerance of the nitrogen-containing compound can be enhanced, so that the voltage characteristic and the efficiency characteristic of an electronic element applying the nitrogen-containing compound can be improved, for example, the open-circuit voltage and the photoelectric efficiency of a photoelectric conversion device are improved, the driving voltage of an organic electroluminescent device is reduced, the luminous efficiency of the organic electroluminescent device is improved, and the like. The adamantyl is in spiro union with the substituted or unsubstituted fluorenyl, so that both sides of the adamantyl are in aromatic ring structures, and the adamantyl can be simultaneously protected by aryl groups on both sides, so that the dehydrogenation reaction of the adamantyl at high temperature can be inhibited, the stability of the nitrogen-containing compound can be improved, and the service life of an electronic element using the nitrogen-containing compound can be improved, such as the service life of a photoelectric conversion device and an organic electroluminescent device. Furthermore, since the nitrogen-containing compound is more stable at high temperatures, it has better thermal stability when used in mass production of electronic components, and can improve the uniformity of mass production of electronic components.
It should be understood that this application is not intended to limit the application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. The foregoing variations and modifications are within the scope of the present application. It will be understood that the application disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute a number of alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.

Claims (6)

1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
Figure FDA0003466345040000011
wherein Ar is1Selected from the group consisting of:
Figure FDA0003466345040000012
Ar2and Ar3Each independently selected from the group consisting of:
Figure FDA0003466345040000013
Figure FDA0003466345040000021
Ar4and Ar5Independently selected from deuterium, halogen, cyano, heteroaryl with 3-18 carbon atoms, aryl with 6-18 carbon atoms and alkyl with 1-10 carbon atoms;
a is selected from 0;
b is selected from 0.
2. A nitrogen-containing compound selected from the group consisting of:
Figure FDA0003466345040000022
Figure FDA0003466345040000031
Figure FDA0003466345040000041
Figure FDA0003466345040000051
Figure FDA0003466345040000061
Figure FDA0003466345040000071
Figure FDA0003466345040000081
Figure FDA0003466345040000091
Figure FDA0003466345040000101
Figure FDA0003466345040000111
Figure FDA0003466345040000121
Figure FDA0003466345040000131
Figure FDA0003466345040000141
Figure FDA0003466345040000151
Figure FDA0003466345040000161
Figure FDA0003466345040000171
Figure FDA0003466345040000181
Figure FDA0003466345040000191
Figure FDA0003466345040000201
Figure FDA0003466345040000211
Figure FDA0003466345040000221
Figure FDA0003466345040000231
Figure FDA0003466345040000241
Figure FDA0003466345040000251
Figure FDA0003466345040000261
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 contains 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 a hole transport layer comprising the nitrogen-containing compound.
5. The electronic component according to claim 3 or 4, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
6. An electronic device comprising the electronic component according to any one of claims 3 to 5.
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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011093825A (en) * 2009-10-28 2011-05-12 Hodogaya Chem Co Ltd Compound including 2,2-diphenyladamantyl structure, and organic electroluminescent element
WO2017116168A1 (en) * 2015-12-31 2017-07-06 머티어리얼사이언스 주식회사 Organic electroluminescent element
CN107459466A (en) * 2016-06-02 2017-12-12 株式会社Lg化学 Compound and the organic electronic element for including it
KR20180078177A (en) * 2016-12-29 2018-07-09 머티어리얼사이언스 주식회사 Organic compound and organic electroluminescent device comprising the same
US10135001B1 (en) * 2017-09-13 2018-11-20 Int Tech Co., Ltd. Organic electroluminescent compound and organic electroluminescent device containing the same
CN110156756A (en) * 2019-05-27 2019-08-23 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN110467536A (en) * 2019-06-14 2019-11-19 陕西莱特光电材料股份有限公司 Nitrogenous compound, organic electroluminescence device and photoelectric conversion device
CN110563647A (en) * 2019-08-27 2019-12-13 陕西莱特光电材料股份有限公司 nitrogen-containing compound, organic electroluminescent device, and photoelectric conversion device

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011093825A (en) * 2009-10-28 2011-05-12 Hodogaya Chem Co Ltd Compound including 2,2-diphenyladamantyl structure, and organic electroluminescent element
WO2017116168A1 (en) * 2015-12-31 2017-07-06 머티어리얼사이언스 주식회사 Organic electroluminescent element
CN107459466A (en) * 2016-06-02 2017-12-12 株式会社Lg化学 Compound and the organic electronic element for including it
KR20180078177A (en) * 2016-12-29 2018-07-09 머티어리얼사이언스 주식회사 Organic compound and organic electroluminescent device comprising the same
US10135001B1 (en) * 2017-09-13 2018-11-20 Int Tech Co., Ltd. Organic electroluminescent compound and organic electroluminescent device containing the same
CN110156756A (en) * 2019-05-27 2019-08-23 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN110467536A (en) * 2019-06-14 2019-11-19 陕西莱特光电材料股份有限公司 Nitrogenous compound, organic electroluminescence device and photoelectric conversion device
CN110563647A (en) * 2019-08-27 2019-12-13 陕西莱特光电材料股份有限公司 nitrogen-containing compound, organic electroluminescent device, and photoelectric conversion device

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