CN112300055B - Nitrogen-containing compound, electronic component, and electronic device - Google Patents

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

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CN112300055B
CN112300055B CN202011173737.5A CN202011173737A CN112300055B CN 112300055 B CN112300055 B CN 112300055B CN 202011173737 A CN202011173737 A CN 202011173737A CN 112300055 B CN112300055 B CN 112300055B
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nitrogen
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马天天
杨敏
南朋
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application provides a nitrogen-containing compound shown as chemical formula 1, an electronic element and an electronic device, and belongs to the technical field of organic materials. In the nitrogen-containing compound represented by the chemical formula 1, R 1 To R 8 The same or different, and at least two groups selected from the group represented by chemical formula 2. The nitrogen-containing compound can improve the performance of electronic elements, particularly the performance of organic electroluminescent devices and photoelectric conversion devices.
Figure DDA0002748106500000011

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 component, and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the application range of electronic elements for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic element is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the organic light emitting layer under the action of the electric field, holes on the anode side also move to the light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
Although there are some organic materials that can be used to transport holes, 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. 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.
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 BDA0002748106480000011
R 1 to R 7 The same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, cycloalkyl group with 3-20 carbon atoms, and group shown in chemical formula 2; r is 1 To R 7 At least one group selected from the group represented by chemical formula 2;
R 8 selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a haloaryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or a group represented by chemical formula 2;
n is R 8 The number of (b) is selected from 0,1,2,3,4,5; when n is>1, any two R 8 The same or different;
Ar 3 is selected from substituted or unsubstituted aryl with 6-12 carbon atoms;
each of L and L 1 、L 2 The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 6-24 carbon atoms;
wherein R is 1 ～R 8 At least 2 of them are selected from the structures shown in formula 2; when chemical formula 1 includes a plurality of groups represented by chemical formula 2, any two of L are the same or different, and any two of L are 1 Identical or different, any two L 2 Identical or different, any two Ar 1 Identical or different, any two Ar 2 The same or different.
According to a second aspect of the present application, there is provided an electronic component including an anode and a cathode which are oppositely disposed, and a functional layer provided between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, 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 diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
The reference numerals of the main elements in the figures are 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 light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
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 terms "comprising" and "having" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.
In the context of the present application, it is,
Figure BDA0002748106480000031
refers to a position bonded to other substituents or bonding positions.
In this application, the number of carbon atoms of a group refers to all the number of carbon atoms. For example, in a substituted arylene group having 10 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 10. Illustratively, the 9, 9-dimethylfluorenyl group is a substituted aryl group having 15 carbon atoms.
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, se, si, 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.
The description adopted in the application of 'each 8230' \8230, independently 'and' 8230 '\8230'; 'each independently' and '8230'; 'independently selected from' are interchangeable, should be understood in a broad sense, and can mean that in different groups, the specific options expressed between the same symbols do not affect each other, or that in the same groups, the specific options expressed between the same symbols do not affect each otherAnd (6) sounding. For example: in "
Figure BDA0002748106480000032
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 ' 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 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, halogen groups (F, cl, br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, alkylamino, cycloalkyl, heterocyclyl.
In this application, "optional" or "optionally" means that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, two substituents attached to the same atom are linked to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atoms to which they are commonly attached" means: when two substituents are bonded to the same atom, the two substituents may be present independently of each other, or may be bonded to each other so as to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are bonded together.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have from 1 to 10 carbon atoms, and in this application, numerical ranges such as "1 to 10" refer to each integer in the given range; for example, "1 to 10 carbon atoms" means that 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 can be includedAlkyl of 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. In still other embodiments, the alkyl group contains 1 to 5 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH) 3 ) Ethyl (Et, -CH) 2 CH 3 ) N-propyl (n-Pr, -CH) 2 CH 2 CH 3 ) Isopropyl group (i-Pr, -CH (CH) 3 ) 2 ) N-butyl (n-Bu, -CH) 2 CH 2 CH 2 CH 3 ) Isobutyl (i-Bu, -CH) 2 CH(CH 3 ) 2 ) Sec-butyl (s-Bu, -CH (CH) 3 )CH 2 CH 3 ) Tert-butyl (t-Bu, -C (CH) 3 ) 3 ) And the like. Further, the alkyl group may be substituted or unsubstituted.
In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic 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, ordinary or 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, bridged rings, in which two rings share one carbon atom, fused rings, and bridged rings, in which two rings share more than two carbon atoms. In addition, cycloalkyl groups may be substituted or unsubstituted. In some embodiments cycloalkyl is 5 to 10 membered cycloalkyl, in other embodiments cycloalkyl is 5 to 8 membered cycloalkyl, examples of which may be, but are not limited to: five-membered cycloalkyl, i.e., cyclopentyl, six-membered cycloalkylcyclohexylalkyl, 10-membered polycycloalkyl such as adamantyl, and the like.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bonds in a conjugated manner, a monocyclic aryl group and a fused ring aryl group joined by carbon-carbon bonds in a conjugated manner, or two or more fused ring aryl groups joined by carbon-carbon bonds in a conjugated manner. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, se, si and the like. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl a benzofluoranthenyl group,
Figure BDA0002748106480000042
And the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 13. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, 31, 32, 33, 34, 35, 36 or 40, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms in a substituted aryl group, as used herein, refers to the total number of carbon atoms in the aryl group and in the substituents on the aryl group, e.g., a substituted aryl group having a carbon number of 18, refers to a total carbon number of 18 in the aryl group and in the substituents thereof.
In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthrenyl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorenyl, and the like.
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 BDA0002748106480000041
in the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, si, se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups 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-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), 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. The term "heteroaryl" as used herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 12 to 20. For example, the number of carbon atoms may be 3,4,5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, N-phenylcarbazolyl, 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 the present application, specific examples of the heteroaryl group as a substituent include, but are not limited to: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthrolinyl, and the like.
In this application, the explanation for aryl applies to arylene, the explanation for heteroaryl applies equally to heteroarylene, the explanation for alkyl applies to alkylene, and the explanation for cycloalkyl applies to cycloalkylene.
In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring means a benzene ring, an indene ring, a naphthalene ring and the like.
The "ring" in the present application includes saturated rings, unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl, unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2,3,4,5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
Specific examples of triarylsilicon groups having 18 to 24 carbon atoms in the present application include, but are not limited to: triphenylsilyl groups, and the like.
Specific examples of the cycloalkyl group having 3 to 20 carbon atoms in the present application include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002748106480000051
It means that one end of the linkage may be attached to any position in the ring system through which the linkage runs, and the other end to the rest of the compound molecule. For example, the following formula (A)X), the naphthyl group represented by formula (X) is bonded to the rest of the molecule through two non-positional bonds extending through the bicyclic ring, and the meanings thereof include any of the possible bonding modes as shown in formulas (X-1) to (X-10).
Figure BDA0002748106480000061
For example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group represented by formula (X '-1) to formula (X' -4) includes any possible bonding means as shown in formulas (X '-1) to (X' -4).
Figure BDA0002748106480000062
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 BDA0002748106480000063
The application provides a nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
Figure BDA0002748106480000071
R 1 to R 7 The same or different, and each is independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-20 carbon atoms, and group represented by chemical formula 2Clustering; r is 1 To R 7 At least one group selected from the group represented by chemical formula 2;
R 8 selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or a group represented by chemical formula 2;
n is R 8 The number of (a) is selected from 0,1,2,3,4,5; when n is>At 1, any two R 8 The same or different;
Ar 3 is selected from substituted or unsubstituted aryl with 6-12 carbon atoms;
each of L and L 1 、L 2 The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 6-24 carbon atoms;
wherein R is 1 ～R 8 At least 2 of them are selected from the structures shown in formula 2; when chemical formula 1 includes a plurality of groups represented by chemical formula 2, any two of L are the same or different, and any two of L are 1 Identical or different, any two L 2 Identical or different, any two Ar 1 Identical or different, any two Ar 2 The same or different.
In the nitrogen-containing compound provided by the application, a triarylamine structure is connected to an N-phenyl-4-aryl carbazole parent nucleus in a conjugated manner. The carbazolyl and the triarylamine group both have good hole transport capability, and the hole transport capability can be further enhanced after the carbazolyl and the triarylamine group are connected in a conjugated manner. The phenyl group connected with N on the N-phenyl-4-aryl carbazole parent nucleus and the aryl group at the 4 th site can further enlarge the conjugated plane of the nitrogen-containing compound and strengthen the conjugated system of the nitrogen-containing compound, and the electron cloud density on the nitrogen-containing compound is improved, so that the hole transport capability of the nitrogen-containing compound is improved. Furthermore, in the N-phenyl-4-arylcarbazole parent nucleus, the phenyl group attached to N is sterically competitive with the hydrogen or substituent at the 1/8 position of carbazole, and the aryl group at the 4 position is sterically competitive with the hydrogen or substituent at the 5 position of carbazole; the planes of the phenyl connected to the N and the aryl at the 4-position are deviated from the plane of the carbazole, so that the conjugation degree of the nitrogen-containing compound can be adjusted to realize adjustment of the HOMO (highest occupied molecular orbital) energy level, the HOMO energy level of the nitrogen-containing compound can be well matched with the electron blocking layer or the organic light emitting layer, and the efficiency of injecting holes into the organic light emitting layer is further improved. In addition, the planes of the phenyl on N and the aryl at the 4-position are deviated from the plane of carbazole, so that the asymmetry of the nitrogen-containing compound can be improved, the pi-pi stacking effect of the nitrogen-containing compound can be reduced, the film forming property of the nitrogen-containing compound can be improved, and the thermal stability of an electronic element using the nitrogen-containing compound can be improved.
Alternatively, R 1 To R 7 The same or different, and each is independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, norbornyl, or a group represented by chemical formula 2.
Alternatively, R 8 Selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or a group of formula 2.
In this application, R 1 To R 4 At most one group selected from the group represented by chemical formula 2, R 5 To R 7 At most one group selected from the group represented by chemical formula 2, when n>At 1 time, each R 8 At most one group selected from the group represented by chemical formula 2.
In this application, R 1 To R 8 In total, 2 or 3 groups are represented by chemical formula 2, and the remainder are hydrogen.
In one embodiment of the present application, R 1 To R 8 Are the same or different and are each independently selected from hydrogen or a group represented by chemical formula 2.
In the present application, the nitrogen-containing compound is selected from compounds represented by the following chemical formula:
Figure BDA0002748106480000081
preferably, ar is 3 Selected from phenyl, naphthyl and biphenyl.
In one embodiment of the present application, L 1 、L 2 The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
In another embodiment of the present application, L 1 、L 2 The same or different, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group.
Optionally, the L, L 1 、L 2 The substituents (A) are the same or different and are each independently selected from deuterium, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
Specifically, the L and the L 1 And L 2 Substituents of (a) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, phenanthryl, and the like.
In one embodiment of the present application, L 1 、L 2 The same or different, and each is independently selected from a single bond or substituted or unsubstituted W: unsubstituted W is selected from the group consisting of:
Figure BDA0002748106480000082
Figure BDA0002748106480000091
wherein the content of the first and second substances,
Figure BDA0002748106480000092
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl; when the number of substituents of the group W is more than 1, the substituents may be the same or different.
Alternatively, L 1 、L 2 The same or different, and each is independently selected from the group consisting of a single bond or the following substituents:
Figure BDA0002748106480000093
in one embodiment of the present application, ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-20 carbon atoms.
Optionally, the Ar is 1 And Ar 2 The substituents of (a) are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.
Specifically, the Ar 1 And Ar 2 Substituents of (c) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dimethylfluorenylDiphenylfluorenyl, spirobifluorenyl, carbazolyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, and the like.
Preferably, ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-15 carbon atoms, and substituted or unsubstituted heteroaryl with 12-18 carbon atoms.
In another embodiment of the present application, ar 1 And Ar 2 Identical or different and each is independently selected from the group consisting of substituted or unsubstituted V: unsubstituted V is selected from the group consisting of:
Figure BDA0002748106480000094
wherein the content of the first and second substances,
Figure BDA0002748106480000095
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl; when the number of substituents of the group V is more than 1, the substituents may be the same or different.
Alternatively, ar 1 And Ar 2 The same or different, and each is independently selected from the group consisting of:
Figure BDA0002748106480000101
in some embodiments, the chemical formula 2
Figure BDA0002748106480000102
The group shown is selected from the group consisting of:
Figure BDA0002748106480000103
Figure BDA0002748106480000111
Figure BDA0002748106480000121
preferably, the nitrogen-containing compound is selected from the group consisting of:
Figure BDA0002748106480000122
Figure BDA0002748106480000131
Figure BDA0002748106480000141
Figure BDA0002748106480000151
Figure BDA0002748106480000161
Figure BDA0002748106480000171
Figure BDA0002748106480000181
Figure BDA0002748106480000191
Figure BDA0002748106480000201
Figure BDA0002748106480000211
the application also provides an electronic element, which comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
The nitrogen-containing compounds provided herein can be used to form at least one organic film layer in a functional layer to improve voltage characteristics, efficiency characteristics, or lifetime characteristics of an electronic component. Optionally, an organic film layer containing a nitrogen-containing compound of the present application is positioned between the anode and the energy conversion layer of the electronic component to improve the transport of holes between the anode and the energy conversion layer. Further, the functional layer comprises a hole transport layer, and the hole transport layer comprises the nitrogen-containing compound of the present application; or the functional layer comprises a hole injection layer, and the hole injection layer comprises the nitrogen-containing compound of the present application; or the functional layer comprises a hole transport layer and a hole injection layer, and the hole transport layer and the hole injection layer both contain the nitrogen-containing compound of the present application.
The electronic element of the present application may be, for example, an organic electroluminescent device or a photoelectric conversion device. For an organic electroluminescent device, its functional layers may include an organic light-emitting layer as an energy conversion layer; for a photoelectric conversion device, the functional layer may include a photoelectric conversion layer as an energy conversion layer.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be, for example, a red organic electroluminescent device, a blue organic electroluminescent device, a green organic electroluminescent device, a yellow organic electroluminescent device, a white organic electroluminescent device, or an organic electroluminescent device of other colors.
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 injection layer 310, and the hole injection layer 310 is disposed on a surface of the anode 100 near the organic light emitting layer 330.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 is disposed between the organic light emitting layer 330 and the anode 100. Further, when the functional layer 300 includes the hole transport layer 321 and the hole injection layer 310, the hole injection layer 310 is interposed between the hole transport layer 321 and the anode 100.
In a specific embodiment, the hole injection layer 310 comprises a nitrogen-containing compound as provided herein. Preferably, the hole injection layer 310 includes a hole injection host material and the nitrogen-containing compound of the present application as a hole injection adjusting material. Further, in the hole injection layer 310, the amount of the hole injection host material is larger than that of the nitrogen-containing compound of the present application. In one embodiment of the present application, the hole injection host material is F4-TCNQ.
In a specific embodiment, the hole transport layer 321 includes the nitrogen-containing compound provided herein to improve the hole transport capability of the organic electroluminescent device, thereby improving the light emitting efficiency of the organic electroluminescent device and reducing the driving voltage of the organic electroluminescent device. Alternatively, the hole transport layer 321 may be composed of the nitrogen-containing compound of the present application.
Optionally, the anode 100 comprises an anode material, which is 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 comprises indium tin oxide (I) and (II)Indium Tin Oxide (ITO) is used as the transparent electrode of the anode.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, or may include a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, the excitons transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be BH-01.
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-01.
Alternatively, the cathode 200 includes a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: 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, liO 2 Al, liF/Ca, liF/Al and BaF 2 But not limited thereto,/Ca. Preferably, a metal electrode comprising an Mg-Ag alloy is included as a cathode.
Alternatively, as shown in fig. 1, an electron transport layer 340 may be further disposed between the cathode 200 and the organic light emitting layer 330. The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not limited in this application. For example, in one embodiment of the present application, the electron transport layer 340 may be composed of ET-06 and LiQ.
Optionally, as shown in fig. 1, an electron blocking layer 322 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability of injecting holes into the organic light emitting layer 330. The electron blocking layer 322 may be selected from benzidine derivatives, triarylamine compounds, or other materials, which are not particularly limited in this application. In one embodiment of the present application, the electron blocking layer 322 may be composed of EB-01.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 may include Yb.
According to another embodiment, the electronic component may be a photoelectric conversion device, 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, as shown in fig. 3; the functional layer 300 comprises a nitrogen-containing compound as provided herein. Among them, the functional layer includes a photoelectric conversion layer 360 as an energy conversion layer.
Alternatively, the nitrogen-containing compound provided herein may be used to form at least one organic thin layer in the functional layer 300 to improve the photoelectric conversion device performance, in particular, to increase the open circuit voltage of the photoelectric conversion device or to increase the photoelectric conversion efficiency of the photoelectric conversion device.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 includes the nitrogen-containing compound of the present application. 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, the functional layer 300 includes a hole injection layer containing the nitrogen-containing compound of the present application.
In one embodiment of the present application, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 321, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell includes an anode 100, a hole transport layer 321, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked, wherein the hole transport layer 321 contains the nitrogen-containing compound of the present application.
In another embodiment of the present application, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole injection layer (not shown in fig. 3), a hole transport layer 321, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked. Wherein the hole injection layer contains the nitrogen-containing compound of the present application.
The application also provides an electronic device which comprises the electronic element.
According to one embodiment, as shown in fig. 2, the electronic device provided by the present application is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The electronic device may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device has the organic electroluminescent device, the electronic device has the same beneficial effects, and the details are not repeated.
According to another embodiment, as shown in fig. 4, the electronic device provided by the present application is a second electronic device 500, and the second electronic device 500 includes the above photoelectric conversion device. The electronic device may be, for example, 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 has the photoelectric conversion device, the electronic device has the same beneficial effects, and the 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.
And (3) synthesis of an intermediate:
Figure BDA0002748106480000241
1-bromo-2-iodo-3-chlorobenzene (50.0g, 157.5 mmol), phenylboronic acid (19.2g, 157.5 mmol), tetrakis (triphenylphosphine) palladium (9.1g, 7.8mmol), tetrabutylammonium bromide (2.5g, 7.8mmol), potassium carbonate (65.2g, 472.6mmol), toluene (400 mL), ethanol (200 mL), deionized water (100 mL) were added to a dried and nitrogen-substituted round-bottom flask, and the mixture was heated to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was subjected to silica gel column chromatography using dichloromethane/n-heptane (1.
To a dried nitrogen-substituted round-bottomed flask, SM-D (35.8g, 133.8mmol) and tetrahydrofuran (400 mL) were added, and after cooling to-78 ℃, n-butyllithium (12.8g, 200.7mmol) was added dropwise, and after completion of the addition, heat was preserved at-78 ℃ for 30min, and after completion of the addition, trimethyl borate (41.7g, 401.4mmol) was added dropwise, and after completion of the addition, heat was preserved at-78 ℃ for 30min. Heating to room temperature, stirring for 12h, and adding hydrochloric acid aqueous solution to adjust pH to neutral. The resulting reaction was filtered to give a crude product, which was recrystallized from n-heptane (600 mL) to give SM-D-1 (19.6 g, 63% yield).
Referring to the synthesis method of intermediate SM-D, the intermediates shown in table 1 below were synthesized by substituting reactant Q in table 1 below for phenylboronic acid:
table 1: synthesis of partial intermediate
Figure BDA0002748106480000242
Referring to the synthesis method of intermediate SM-D, the intermediates shown in table 2 below were synthesized by substituting reactant N for 1-bromo-2-iodo-3-chlorobenzene and reactant M for phenylboronic acid in table 2 below:
table 2: synthesis of partial intermediate
Figure BDA0002748106480000251
Referring to the synthesis of intermediate SM-D-1, the intermediates shown in table 3 below were synthesized instead of SM-D in table 3 below:
table 3: synthesis of partial intermediate
Figure BDA0002748106480000252
Figure BDA0002748106480000261
Figure BDA0002748106480000262
To a dry, nitrogen-purged round-bottomed flask, SM-D-1 (5.0 g,26.0 mmol), 2, 4-dichloronitrobenzene (6.1g, 26.0 mmol), tetrakis (triphenylphosphine) palladium (0.6g, 0.5mmol), tetrabutylammonium bromide (0.4g, 1.3mmol), potassium carbonate (10.8g, 78.1mmol), toluene (40 mL), ethanol (20 mL), deionized water (10 mL) were added, and the mixture was heated to 78 ℃ under stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1.
Adding IMA-1 (5.0 g of 14.5 mmol), triphenylphosphine (9.5 g of 36.3 mmol) and o-dichlorobenzene (40 mL) into a dried and nitrogen-replaced round-bottom flask, heating to 160 ℃ under stirring, and reacting for 6h; and then silica gel was added thereto to volatilize the liquid therein, followed by silica gel column chromatography purification using dichloromethane/n-heptane (1.
Adding IM-B-1 (5.0 g,16.0 mmol), iodobenzene (3.3 g,16.3 mmol), cuprous iodide (0.61g, 3.2 mmol), potassium carbonate (4.9g, 35.2mmol), 1, 10-phenanthroline (1.2g, 6.4mmol), 18-crown ether-6 (0.4g, 1.6mmol), N, N-dimethylformamide (50 mL) into a dried round-bottomed flask subjected to nitrogen replacement, heating to 160 ℃ under a stirring condition, and keeping for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was subjected to silica gel column chromatography purification using dichloromethane/n-heptane (1.
Referring to the synthesis of IM-A-1, in Table 4 below, starting material A was used in place of 2, 4-dichloronitrobenzene and SM-X was used in place of SM-D-1. Intermediates shown in table 4 below were synthesized:
table 4: synthesis of partial intermediates
Figure BDA0002748106480000263
Figure BDA0002748106480000271
Referring to the synthesis of IM-B-1, the intermediates shown in Table 5 below were synthesized by substituting raw material B in Table 5 below for IM-A-1:
table 5: synthesis of partial intermediates
Figure BDA0002748106480000272
Figure BDA0002748106480000281
Referring to the synthesis of IM-C-1, intermediates shown in Table 6 below were synthesized by substituting IM-B-1 with starting material C in Table 6 below:
table 6: synthesis of partial intermediates
Figure BDA0002748106480000282
Figure BDA0002748106480000291
Figure BDA0002748106480000301
To a dry, nitrogen-purged round-bottomed flask, p-chlorobenzoic acid (4.0g, 25.7mmol), IM-C-1 (5.0g, 12.9mmol), tetrakis (triphenylphosphine) palladium (0.3g, 0.3mmol), tetrabutylammonium bromide (0.18g, 0.6mmol), potassium carbonate (5.3g, 38.6mmol), toluene (40 mL), ethanol (20 mL), deionized water (10 mL) were added, and the temperature was raised to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (100 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1.
Referring to the synthesis of IM-D-1, the intermediates in Table 7 below were synthesized by substituting IM-C-1 with starting material D and p-chlorobenzeneboronic acid with SM-D in Table 7 below:
table 7: synthesis of partial intermediate
Figure BDA0002748106480000302
Figure BDA0002748106480000311
Figure BDA0002748106480000312
To a dry, nitrogen-purged round-bottomed flask, biphenyl-2-boronic acid (51.6g, 260.4mmol), 2, 4-dichloronitrobenzene (50.0g, 260.4mmol), tetrakis (triphenylphosphine) palladium (15.0g, 13.0mmol), tetrabutylammonium bromide (4.2g, 13.0mmol), potassium carbonate (107.9g, 781.3mmol), toluene (400 mL), ethanol (200 mL), deionized water (100 mL) were added, and the mixture was heated to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was subjected to silica gel column chromatography purification using methylene chloride/n-heptane (1.
To a dry round-bottomed flask purged with nitrogen, IM-O-1 (56.5g, 182.4 mmol), triphenylphosphine (119.6 g,456.0 mmol) and O-dichlorobenzene (400 mL) were added, and the mixture was heated to 160 ℃ with stirring to react for 6 hours; and then thereto was added silica gel to volatilize the liquid therein, followed by silica gel column chromatography purification using dichloromethane/n-heptane (1.
Adding IM-P-1 (5.0g, 17.9mmol), P-chloroiodobenzene (4.4g, 18.3mmol), cuprous iodide (0.7g, 3.6mmol), potassium carbonate (5.5g, 39.6mmol), 1, 10-phenanthroline (1.3g, 7.2mmol), 18-crown ether-6 (0.5g, 1.8mmol), N, N, -dimethylformamide (30 mL) into a dried round-bottom flask subjected to nitrogen replacement, and heating to 160 ℃ under the stirring condition for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200 mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1.
The intermediates of Table 8 below were synthesized by the same method as that of IM-O-1, substituting O for 2, 4-dichloronitrobenzene and SM-M for biphenyl-2-boronic acid in Table 8 below:
table 8: synthesis of partial intermediate
Figure BDA0002748106480000321
Figure BDA0002748106480000331
Referring to the same procedure as IM-P-1, the intermediates shown in Table 9 below were synthesized by substituting the starting material P in Table 9 for IM-O-1:
table 9: synthesis of partial intermediates
Figure BDA0002748106480000332
Referring to the synthesis method of IM-Q-1, the intermediate shown in Table 10 below was synthesized by substituting IM-P-1 with Q as a raw material and P-chloroiodobenzene with N as a raw material in Table 10 below:
table 10: synthesis of partial intermediates
Figure BDA0002748106480000341
Figure BDA0002748106480000351
Figure BDA0002748106480000352
A reaction flask was charged with IMC-1 (5.0g, 12.9mmol), SM-1 (diphenylamine) (4.4g, 25.8mmol), tris (dibenzylideneacetone) dipalladium (0.2g, 0.25mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl (0.21g, 0.5mmol), sodium tert-butoxide (4.9g, 51.6mmol) and a toluene solvent (50 mL), heated to 110 ℃ under nitrogen protection, and stirred under reflux for 8h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane (50 mL) and water (50 mL) 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtering, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system (1.
Referring to the synthesis of compound 49, in Table 11 below SM-Y is substituted for SM-1 (diphenylamine) and IM-X is substituted for IM-C-1. The compounds shown in table 11 below were synthesized:
table 11: synthesis of partial Compound
Figure BDA0002748106480000353
Figure BDA0002748106480000361
Figure BDA0002748106480000371
Figure BDA0002748106480000381
Figure BDA0002748106480000391
Mass spectrometry analysis of the above synthesized compounds yielded mass spectrometry data for each compound as shown in table 12 below:
table 12: mass spectral data of partial compounds
Compound number Mass spectrum [ M + H] + Compound number Mass spectrum [ M + H] +
Compound 49 654.3 Compound 178 906.4
Compound 47 654.3 Compound 113 654.3
Compound 26 654.3 Compound 175 834.3
Compound 146 806.3 Compound 176 886.4
Compound 147 958.4 Compound 179 1115.4
Compound 148 820.3 Compound 180 1109.4
Compound 149 730.3 Compound 199 682.3
Compound 150 754.3 Compound 200 766.4
Compound 151 958.4 Compound 201 674.4
Compound 173 958.4 Compound 202 922.4
Compound 174 806.3 Compound 203 704.3
Compound 177 920.4
Nuclear magnetic analysis of the partially synthesized compounds above gave the following nuclear magnetic data for each compound as shown in table 13 below:
table 13: mass spectral data of partial compounds
Figure BDA0002748106480000392
Figure BDA0002748106480000401
Preparation and evaluation of organic electroluminescent device
Example 1: preparation of blue organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0002748106480000402
The ITO substrate (manufactured by Corning) of (1) 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.
Compound 49 and F4-TCNQ were applied to an experimental substrate (anode) at 97%:3% by mass of the above components was co-evaporated to a thickness of
Figure BDA0002748106480000403
And a compound 49 is vapor-deposited on the hole injection layer to form a layer having a thickness of
Figure BDA0002748106480000404
A Hole Transport Layer (HTL).
Vacuum evaporating EB-01 on the hole transport layer to form a layer with a thickness of
Figure BDA0002748106480000405
The electron blocking layer of (1).
On the electron blocking layer, BH-01 and BD-01 were mixed in a ratio of 98%:2% by mass ratio, and forming a film having a thickness of
Figure BDA0002748106480000406
Blue light emitting layer (EML).
ET-06 and LiQ were formed by vapor deposition at a film thickness ratio of 1
Figure BDA0002748106480000407
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
Figure BDA0002748106480000408
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1:9 is formed on the electron injection layer to a thickness of
Figure BDA0002748106480000409
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA00027481064800004010
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 23
An organic electroluminescent device was fabricated by the same method as example 1, except that compounds shown in the column (HIL/HTL) in table 14 below were used instead of compound 49 in forming the hole injection layer/hole transport layer.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the hole injection layer/hole transport layer, the compound a-1 was used instead of the compound 49.
Comparative example 2
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a-2 was used instead of compound 49 in forming the hole injection layer/hole transport layer.
Comparative example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound a-3 was used instead of the compound 49 in forming the hole injection layer/hole transport layer.
The structures of the materials used in the above examples and comparative examples are as follows:
Figure BDA00027481064800004011
Figure BDA0002748106480000411
for the organic electroluminescent device prepared as above, at 20mA/cm 2 Formation tests were performed under the conditions of (1), and the test results are shown in table 14.
Table 14: performance test results of organic electroluminescent device
Figure BDA0002748106480000412
Figure BDA0002748106480000421
From the results in table 14, it is understood that in examples 1 to 23, which are examples of the compound for the hole injection layer/hole transport layer, the luminous efficiency (Cd/a) of the above-mentioned organic electroluminescent device prepared by using the compound used in the present application as the hole injection layer/hole transport layer is improved by at least 13.51%, the external quantum efficiency EQE (%) is improved by at least 13.49%, and the lifetime is improved by at least 6.80%, compared with comparative examples 1 to 4, which are examples of devices corresponding to known compounds.
It should be understood that the application is not limited in its application to the details of construction and the arrangement of components set forth in the present 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 various alternative aspects of the present application. The embodiments described herein explain the best modes known for practicing the application and will enable others skilled in the art to utilize the application.

Claims (15)

1. A nitrogen-containing compound having a structure represented by chemical formula 1-1, chemical formula 1-2, or chemical formula 1-3:
Figure FDA0003996889530000011
wherein Ar is 3 Selected from phenyl, naphthyl, biphenyl;
each of L and L 1 、L 2 The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 6-30 carbon atoms;
each Ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 6-24 carbon atoms;
each of L and L 1 、L 2 、Ar 1 And Ar 2 Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with 0,1,2,3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 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, a heterocycloalkyl group having 2 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.
2. The nitrogen-containing compound according to claim 1, characterized in thatCharacterized in that L and L 1 、L 2 The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
3. The nitrogen-containing compound according to claim 1, wherein L and L are 1 、L 2 The substituents (A) are the same or different and are each independently selected from deuterium, a halogen group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
4. The nitrogen-containing compound according to claim 1, wherein L and L are 1 、L 2 The same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted N-phenylcarbazolyl group.
5. The nitrogen-containing compound according to claim 4, wherein L and L are 1 And L 2 The substituents of (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl.
6. The nitrogen-containing compound according to claim 1, wherein each of L and L is 1 、L 2 The same or different, and each is independently selected from a single bond or substituted or unsubstituted W: unsubstituted W is selected from the group consisting of:
Figure FDA0003996889530000021
wherein the content of the first and second substances,
Figure FDA0003996889530000024
represents a chemical bond; substituted W has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl; when the number of substituents of the group W is more than 1, the substituents may be the same or different.
7. The nitrogen-containing compound according to claim 1, wherein each Ar is Ar 1 And Ar 2 The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-20 carbon atoms.
8. The nitrogen-containing compound according to claim 7, wherein Ar is 1 And Ar 2 The substituents of (a) are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.
9. The nitrogen-containing compound according to claim 1, wherein Ar 1 And Ar 2 Identical or different and each is independently selected from the group consisting of substituted or unsubstituted V: unsubstituted V is selected from the group consisting of:
Figure FDA0003996889530000022
wherein, the first and the second end of the pipe are connected with each other,
Figure FDA0003996889530000023
represents a chemical bond; substituted V has one or more substituents thereon, each independently selected from: deuterium, cyano, halogen groups, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl; when taking the group VWhen the number of substituents is more than 1, the substituents may be the same or different.
10. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0003996889530000031
Figure FDA0003996889530000041
Figure FDA0003996889530000051
Figure FDA0003996889530000061
Figure FDA0003996889530000071
Figure FDA0003996889530000081
Figure FDA0003996889530000091
Figure FDA0003996889530000101
Figure FDA0003996889530000111
Figure FDA0003996889530000121
Figure FDA0003996889530000131
11. 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 10.
12. The electronic component according to claim 11, wherein the functional layer comprises a hole injection layer comprising the nitrogen-containing compound.
13. The electronic component according to claim 11, wherein the functional layer comprises a hole transport layer comprising the nitrogen-containing compound.
14. The electronic element according to claim 11, wherein the electronic element is an organic electroluminescent device or a solar cell.
15. An electronic device comprising the electronic component according to any one of claims 11 to 14.
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