CN111892505A - Nitrogen-containing compound, electronic component, and electronic device - Google Patents

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

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Publication number
CN111892505A
CN111892505A CN202010334387.XA CN202010334387A CN111892505A CN 111892505 A CN111892505 A CN 111892505A CN 202010334387 A CN202010334387 A CN 202010334387A CN 111892505 A CN111892505 A CN 111892505A
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carbon atoms
group
nitrogen
containing compound
independently selected
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CN111892505B (en
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边春阳
马天天
曹佳梅
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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  • Electroluminescent Light Sources (AREA)

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, wherein, Ar1、Ar2、Ar3、Ar4Each independently selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; r1And R2Each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, or the like; n is1Represents R1Number of (2), n2Represents R2The number of (2). The nitrogen-containing compound can improve the performance of an electronic component.
Figure DDA0002466060100000011

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 organic light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
In the prior art, patent document CN110467536A also discloses some new electroluminescent materials. However, there is still a need to develop new materials to further improve the performance of electronic components.
The above information described in the background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
The invention aims to provide a nitrogen-containing compound which can improve the performance of an electronic component, an electronic component and an 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 BDA0002466060080000011
wherein Ar is1、Ar2、Ar3、Ar4Equal to or different from each other, each independently selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar1、Ar2、Ar3、Ar4the substituents on each of which are the same or different from each other and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R1and R2Equal to or different from each other, each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
n1represents R1Is a number of and n1Selected from 0, 1,2, 3 or 4; and when n is1When greater than 1, any two R1The same or different;
n2represents R2Is a number of and n2Selected from 0, 1 or 2; and when n is2When it is 2, two R2The 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 a third aspect of the present application, an electronic device is provided, which includes the above electronic element.
In the nitrogen-containing compound provided by the application, two triarylamine groups are connected through fluorenyl groups screwed by adamantane, and the triarylamine is positioned on a ring on the same side of the fluorenyl groups, so that the molecular asymmetry is increased; the combination mode enables the material to have excellent performance of inhibiting material crystallization while keeping high hole mobility, and when the material is used for a hole transport layer of an organic electroluminescent device, a uniform and stable film state can be formed, so that hole injection is facilitated, the voltage of the device is reduced, and the device has long service life.
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 nuclear magnetic hydrogen spectrum of Compound 1 of the present application.
FIG. 2 is a nuclear magnetic hydrogen spectrum of Compound 2 of the present application.
Fig. 3 is a schematic structural view of an organic electroluminescent 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.
Fig. 5 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 6 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
Description of the reference numerals：
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320: a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by chemical formula 1:
Figure BDA0002466060080000031
wherein Ar is1、Ar2、Ar3、Ar4Equal to or different from each other, each independently selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar1、Ar2、Ar3、Ar4the substituents on each of which are the same or different from each other and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R1and R2Equal to or different from each other, each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
n1represents R1Is a number of and n1Selected from 0, 1,2, 3 or 4; and when n is1When greater than 1, any two R1The same or different;
n2represents R2Is a number of and n2Selected from 0, 1 or 2; and when n is2When it is 2, two R2The same or different.
In the nitrogen-containing compound provided by the application, two triarylamine groups are connected through fluorenyl groups screwed by adamantane, and the triarylamine is positioned on a ring on the same side of the fluorenyl groups, so that the molecular asymmetry is increased; the combination mode enables the material to have excellent performance of inhibiting material crystallization while keeping high hole mobility, and when the material is used for a hole transport layer of an organic electroluminescent device, a uniform and stable film state can be formed, so that hole injection is facilitated, the voltage of the device is reduced, and the device has long service life.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic 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 hetero atom such as B, N, O, S, P or Si. 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 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
Figure BDA0002466060080000032
and the like.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof that contains at least one heteroatom, which may be at least one of B, O, N, P, Si and S, in the ring. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
Figure BDA0002466060080000041
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-7) includes any possible connection mode shown in the formula (f-1) to the formula (f-7).
Figure BDA0002466060080000042
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
Figure BDA0002466060080000043
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
Figure BDA0002466060080000051
In the present application, a cycloalkyl group having 3 to 10 carbon atoms may be used as a substituent for the aryl group or the heteroaryl group, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a linear alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms, and examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups, and the like.
In the present application, halogen may include fluorine, chlorine, bromine, iodine.
In the present application, specific examples of the alkoxy group having 1 to 10 carbon atoms, which may have 1,2, 3,4, 5, 6, 7, 8, 9,10, or C1 to C10 carbon atoms, include, but are not limited to, methoxy group, ethoxy group, n-propoxy group, and the like.
In the present application, the number of carbon atoms of the aryl group having 6 to 20 carbon atoms and the aryl group having 6 to 18 carbon atoms may be independently 6 (for example, phenyl), 10 (for example, naphthalene), 12 (for example, biphenyl), 15, 18, or the like.
In the present application, the structure of the nitrogen-containing compound may be specifically represented by chemical formula 1-1 to chemical formula 1-6:
Figure BDA0002466060080000052
in some specific embodiments, the nitrogen-containing compound has a structure represented by chemical formula 1-1 or chemical formula 1-2.
In this application, when Ar is1、Ar2、Ar3And Ar4When having a substituent(s), the number of the substituent(s) may be one or more (i.e., one or more)One); when the number of the substituents is two or more, the substituents may be the same or different.
Alternatively, Ar1、Ar2、Ar3、Ar4Each independently selected from: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
Alternatively, Ar1、Ar2、Ar3、Ar4May be each independently selected from the group consisting of substituents represented by the formulae i-1 to i-15:
Figure BDA0002466060080000061
wherein M is1Selected from a single bond or
Figure BDA0002466060080000062
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C(F4) When, two arbitrary F4The same or different;
H1selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms and alkylthio having 1 to 10 carbon atoms;
H2～H9、H21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
H10～H20、F1～F4each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
h1～h21by hkIs represented by H1～H21With HkK is a variable and represents an arbitrary integer of 1 to 21, hkRepresents a substituent HkThe number of (2); wherein, when k is selected from 5 or 17, hkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when h iskWhen greater than 1, any two HkThe same or different;
K1selected from O, S, 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 or a cycloalkyl group having 3 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, N (H)25)、C(H26H27)、Si(H26H27) (ii) a 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 or a cycloalkyl group having 3 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.
In the present application, in the formulae i-10 and i-11, when K is2When it represents a single bond, the specific structures of the formulae i-10 and i-11 are as follows:
Figure BDA0002466060080000071
in the present application, the above-mentioned H23And H24H above26And H27In both groups, the ring formed by the interconnection of the two groups in each group may be saturated or unsaturated, for example a saturated or unsaturated 3 to 13 membered ring may be formed. For example, in the formula i-10, when K is2And M1Are all single bonds, H19Is hydrogen, h19＝7，K1Is C (H)23H24)，H23And H24When they are linked to each other to form a five-membered ring with the atoms to which they are commonly attached, formula i-10 is
Figure BDA0002466060080000072
Likewise, chemical formulai-10 may also represent
Figure BDA0002466060080000073
I.e. H23And H24The atoms that are linked to each other to be commonly bound to them form a partially unsaturated 13-membered ring.
Alternatively, Ar1、Ar2、Ar3And Ar4The substituents on (a) may each be independently selected from: deuterium, fluorine, cyano, alkyl group having 1 to 4 carbon atoms, cycloalkyl group having 5 to 10 carbon atoms, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, and alkylsilyl group having 3 to 7 carbon atoms (for example, trimethylsilyl group). Specifically, Ar1、Ar2、Ar3And Ar4The substituents on (a) may each be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, trimethylsilyl, cyclohexyl and the like, for example.
Alternatively, R1And R2Each independently selected from: deuterium, fluorine, cyano, alkyl group having 1 to 4 carbon atoms, cycloalkyl group having 5 to 10 carbon atoms, alkoxy group having 1 to 4 carbon atoms, alkylthio group having 1 to 4 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms (e.g., trimethylsilyl group), aryl group having 6 to 15 carbon atoms, and heteroaryl group having 5 to 12 carbon atoms.
Alternatively, n10, 1 or 2.
According to an exemplary embodiment, n10, 1 or 2, R1Selected from the group consisting of fluoro, cyano, methoxy, methyl, ethyl, tert-butyl, deuterium, trimethylsilyl, cyclohexyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl.
According to an exemplary embodiment, n20, 1 or 2, R2Selected from fluorine, cyano, methoxy, methylthio, methyl, ethyl, tert-butyl, deuterium, trimethylsilyl and phenyl.
According to one embodiment, Ar1Is substituted or unsubstituted Z1，Ar2Is substituted or unsubstitutedZ2，Ar3Is substituted or unsubstituted Z3，Ar4Is substituted or unsubstituted Z4(ii) a Wherein, Z is unsubstituted1、Z2、Z3And Z4Each independently selected from the group consisting of:
Figure BDA0002466060080000081
in this embodiment, Z is unsubstituted1、Z2、Z3And Z4For example, each may be independently selected from the group consisting of:
Figure BDA0002466060080000082
Figure BDA0002466060080000091
Figure BDA0002466060080000101
in this embodiment, substituted Z1Substituted Z2Substituted Z3Substituted Z4Each independently has one or more substituents selected from deuterium, cyano, fluorine, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and a pyridyl group.
According to an exemplary embodiment, Ar1、Ar2、Ar3、Ar4May each be independently selected from the group consisting of:
Figure BDA0002466060080000102
Figure BDA0002466060080000111
according to one embodiment, in the nitrogen-containing compound, Ar1And Ar3Same as Ar2And Ar4The same is true. Alternatively, the nitrogen-containing compound may be specifically selected from the group consisting of:
Figure BDA0002466060080000112
Figure BDA0002466060080000121
Figure BDA0002466060080000131
Figure BDA0002466060080000141
Figure BDA0002466060080000151
Figure BDA0002466060080000161
Figure BDA0002466060080000171
Figure BDA0002466060080000181
Figure BDA0002466060080000191
Figure BDA0002466060080000201
Figure BDA0002466060080000211
Figure BDA0002466060080000221
Figure BDA0002466060080000231
Figure BDA0002466060080000241
Figure BDA0002466060080000251
Figure BDA0002466060080000261
Figure BDA0002466060080000271
Figure BDA0002466060080000281
the method for synthesizing the nitrogen-containing compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method based on the nitrogen-containing compound of the present invention in combination with the preparation method of the synthesis example. In other words, the synthesis examples section of the present application illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from the preparation of these exemplary syntheses, and all specific preparations for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the scope of the application.
In a second aspect, the present application provides an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
The nitrogen-containing compound provided by the application can be used for forming at least one organic film layer in the functional layer, so that the electronic element has beneficial voltage characteristics, efficiency characteristics or service life characteristics at the same time, and particularly the voltage characteristics and the service life characteristics of the electronic element can be improved.
Optionally, an organic film layer containing a nitrogen-containing compound of the present application is positioned between the anode and the energy conversion layer of the electronic component in order to improve the transport of holes between the anode and the energy conversion layer.
Optionally, the functional layer comprises a hole transport layer comprising a nitrogen-containing compound as provided herein. The hole transport layer may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials. The hole transport layer may be one layer, or may be two or more layers.
According to one embodiment, the electronic component may be an organic electroluminescent device. As shown in fig. 3, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked, wherein the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322.
Optionally, the nitrogen-containing compound provided by the present application can be applied to the second hole transport layer 322 of the organic electroluminescent device to improve the lifetime of the organic electroluminescent device and reduce the driving voltage of the organic electroluminescent device.
In the present application, the anode 100 includes an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); gold in combinationMetals and oxides such as ZnO, Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. In one embodiment, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. 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.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of DBimiBphen and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably comprising magnesium and silverThe metal electrode serves as a cathode.
Optionally, as shown in fig. 3, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the hole transport layer. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, hole injection layer 310 may be comprised of m-MTDATA or HAT-CN.
Optionally, as shown in fig. 3, 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 alkali metal sulfide, alkali metal halide, Yb, or the like, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may include LiQ or Yb.
Alternatively, as shown in fig. 3, the hole injection layer 310, the first hole transport layer 321, the second hole transport layer 322, the organic light emitting layer 330, the electron transport layer 340, and the electron injection layer 350 constitute the functional layer 330.
According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 5, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises a nitrogen-containing compound as provided herein.
Alternatively, as shown in fig. 5, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application. The hole transport layer 320 may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
Optionally, the hole transport layer 320 may further include an inorganic doping material to improve the hole transport property of the hole transport layer 321.
Alternatively, as shown in fig. 5, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer contains the nitrogen-containing compound of the present application.
In a third aspect, the present application further provides an electronic device including any one of the electronic components described in the above electronic component embodiments. Since the electronic device has any one of the electronic elements described in the above embodiments of the electronic element, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.
For example, as shown in fig. 4, the present application provides an electronic device, i.e., a first electronic device 400, which may include the above-mentioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device has the organic electroluminescent device, the electronic device has the same beneficial effects, and the details are not repeated herein.
For another example, as shown in fig. 6, the present application provides another electronic device, i.e., a second electronic device 500, which includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, 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.
The present application is further illustrated by the following examples.
1. Synthesis of intermediates
The structure and specific numbering of each intermediate II is as follows:
Figure BDA0002466060080000301
the general synthetic routes of the intermediates A to D, the intermediates A-1 to D-1 and the intermediates D-2 to D-4 are as follows:
Figure BDA0002466060080000302
wherein R is1Represents H, F, methyl or tert-butyl; r2Represents a methyl group, a phenyl group or-F.
The synthesis of the intermediate is illustrated below by taking intermediate a as an example.
(1)
Figure BDA0002466060080000311
Adding raw material 1(46.7g, 165.08mmol), raw material 2(30g, 157.22mmol), anhydrous potassium carbonate (47g, 345.89mmol) TBAB (10.13g, 31.44mmol) into a mixed solution of toluene (373.6mL), ethanol (93.4mL) and water (93.4mL), slowly raising the temperature to 50 ℃, adding tetrakis (triphenylphosphine) palladium (1.82g, 1.57mmol), raising the temperature to reflux, reacting completely after 16h, cooling the reaction solution to room temperature, washing the reaction solution with water to neutrality, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; recrystallization of the crude product from toluene/n-heptane afforded intermediate a1 as a solid (36.4g, 76.66% yield).
(2)
Figure BDA0002466060080000312
Adding the intermediate A1(36.4g, 120.53mmol) into THF (364mL), cooling the system to-90 ℃ under the protection of nitrogen, dropwise adding n-BuLi (120.53mL, 301.33mmol, 2.5M/L), after finishing dropwise adding for 3h, after keeping the temperature and reacting for 1h, dropwise adding a THF solution of 2-adamantanone (14.18g, 96.42mmol,70mL THF), completely dropwise adding for 40min, after keeping the temperature and reacting for 1h, naturally heating to room temperature, adding 500mL water, extracting with 1L dichloromethane, washing with water to neutrality, then adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; column purification of the crude product was performed using n-heptane to yield a solid, intermediate a2(30.6g, yield 68.01%).
(3)
Figure BDA0002466060080000313
Adding the intermediate A2(30.6g, 81.97mmol) into glacial acetic acid (306mL), slowly dropwise adding concentrated sulfuric acid (98 wt%, 8.19mmol) under the protection of nitrogen, after dropwise adding, generating a large amount of solid, slowly heating to 65 ℃, keeping the temperature, reacting for 1h, and completing the reaction. Cooling the reaction solution to room temperature, filtering, dissolving with dichloromethane, washing with water to neutrality, adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; recrystallization of the crude product from dichloromethane/n-heptane afforded intermediate a as a solid (24g, 82.41% yield).
The intermediates II listed in table 1 were synthesized with reference to the procedure for intermediate a, except that starting material 1 was replaced with starting material I and starting material 2 was replaced with starting material II. The numbering, structure and overall yields of the main raw materials used and the intermediates synthesized accordingly are shown in table 1.
TABLE 1
Figure BDA0002466060080000314
Figure BDA0002466060080000321
Wherein, the raw materials
Figure BDA0002466060080000322
The synthesis method comprises the following steps:
(1)
Figure BDA0002466060080000323
adding 3, 5-dichloro-2-iodobromobenzene (57g, 162.0mmol), phenylboronic acid (19.2g, 157.22mmol), anhydrous potassium carbonate (47g, 345.89mmol) and TBAB (10.13g, 31.44mmol) into a mixed solution of toluene (480mL), ethanol (120mL) and water (120mL), slowly heating to 50 ℃, adding tetrakis (triphenylphosphine) palladium (1.82g, 1.57mmol), heating to 60 ℃, reacting for 16h, cooling the reaction solution to room temperature, washing the reaction solution with water to neutrality, adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was recrystallized using a toluene/n-heptane system to yield intermediate b as a solid (40.0g, 81.5% yield).
(2)
Figure BDA0002466060080000331
Under the protection of nitrogen, sequentially adding the intermediate b (27.18g, 90mmol) and 300mL of tetrahydrofuran, starting stirring, cooling the system to-90 ℃ to-80 ℃, starting to dropwise add n-butyl lithium n-hexane solution (2.5mol/L, 96mmol) in the temperature range, then preserving heat for 1.5h, starting to dropwise add tributyl borate (27.42g, 135mmol), reacting at-90 ℃ to-78 ℃ for 2h, then naturally heating to room temperature, pouring the obtained reaction solution into water, stirring for 15min, then carrying out liquid separation, washing the organic phase with water for multiple times until white solids are separated out, filtering and drying to obtain the target product (20.7g, yield 86.6%).
Synthesis of intermediate E:
(1)
Figure BDA0002466060080000332
adding raw material a (58.1g, 165.08mmol), phenylboronic acid (19.2g, 157.22mmol), anhydrous potassium carbonate (47g, 345.89mmol) TBAB (10.13g, 31.44mmol) into a mixed solution of toluene (375mL), ethanol (95mL) and water (95mL), slowly raising the temperature to 50 ℃, adding tetrakis (triphenylphosphine) palladium (1.82g, 1.57mmol), raising the temperature to 60 ℃, reacting for 16h, cooling the reaction liquid to room temperature, washing the reaction liquid with water to neutrality, adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; recrystallization of the crude product from toluene/n-heptane afforded intermediate a1 as a solid (39.0g, 78.2% yield).
(2)
Figure BDA0002466060080000333
Adding the intermediate a1(39.0g, 129.09mmol) into THF (380mL), cooling the system to-90 ℃ under the protection of nitrogen, dropwise adding n-BuLi (129.1mL, 2.5M/L), after finishing dropwise adding for 3h, keeping the temperature for reaction for 1h, dropwise adding a THF solution of 2-adamantanone (15.51g, 103.27mmol,80mL THF), completely dropwise adding for 55min, keeping the temperature for reaction for 1h, naturally heating to room temperature, adding 500mL water, extracting with 1L dichloromethane, washing with water to neutrality, then adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by column chromatography using n-heptane to yield a solid, intermediate a2(31.4g, 65.2% yield).
(3)
Figure BDA0002466060080000334
Adding the intermediate a2(31g, 83.04mmol) into glacial acetic acid (312mL), slowly dropwise adding concentrated sulfuric acid (98 wt%, 8.3mmol) under the protection of nitrogen, after dropwise adding, generating a large amount of solid, slowly heating to 65 ℃, keeping the temperature, reacting for 1h, and completing the reaction. Cooling the reaction solution to room temperature, filtering, dissolving with dichloromethane, washing with water to neutrality, adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; recrystallization of the crude product from dichloromethane/n-heptane gave intermediate E as a solid (24.8g, 84.2% yield).
Intermediate E-1 was synthesized by the method referenced for intermediate E, except that phenylboronic acid was replaced with 2-tolueneboronic acid. The numbering, structure and overall yields of the main raw materials used and the intermediates synthesized accordingly are shown in table 2.
TABLE 2
Figure BDA0002466060080000341
2. Synthesis of Compounds
Synthesis example 1: synthesis of Compound 1:
(1)
Figure BDA0002466060080000342
raw material 3(4.0g, 17.16mmol), raw material 4(1.63g, 17.5mmol), tris (dibenzylideneacetone) dipalladium (0.15g, 0.17 mmol), 2-dicyclohexylphosphorus-2 ', 4', 6 ' -triisopropylbiphenyl (0.16g, 0.34mmol) and sodium tert-butoxide (2.47g, 25.7mmol) were added to toluene (32mL), heated to 108 ℃ under nitrogen protection, stirred for 1h, the reaction solution was cooled to room temperature, the reaction solution was washed with water to neutrality, magnesium sulfate was added to dry, the filtrate was filtered, and the solvent was removed under reduced pressure. The crude product was purified by recrystallization using a dichloromethane/n-heptane system to yield intermediate 1 as a solid (3.0g, 71.27%).
(2)
Figure BDA0002466060080000343
Adding intermediate A (4.43g, 12.47mmol), intermediate 1(3g, 12.22mmol), tris (dibenzylideneacetone) dipalladium (0.11g, 0.12mmol), 2-dicyclohexyl-phosphorus-2 ', 6' -dimethoxy-biphenyl (0.10g, 0.24mmol) and sodium tert-butoxide (1.76g, 18.34mmol) into toluene (32mL), heating to 108 ℃ under nitrogen protection, stirring for 1h, cooling to room temperature, washing the reaction solution to neutrality with water, adding magnesium sulfate for drying, filtering, passing the filtrate through a short silica gel column, removing the solvent under reduced pressure, and recrystallizing and purifying the crude product by using a toluene/n-heptane system to obtain solid compound 1(4.1g, 42.3%), and mass spectrum: 773.4[ M + H ] M/z]+. Fig. 1 is a nuclear magnetic hydrogen spectrum of compound 1, with nuclear magnetic data:1H NMR(CD2Cl2,400MHz):8.07(d,1H),7.95(d,1H),7.79(s,1H),7.55-7.53(m,4H),7.48-7.45(m,4H),7.41-7.38(m,4H),7.31-7.26(m,4H),7.24-7.11(m,12H),7.04(t,1H),6.96(s,1H),6.94(t,1H),2.92(d,2H),2.61-2.57(m,2H),2.15(s,1H),1.90(s,2H),1.85(s,1H)，1.75(d,2H),1.68(d,2H),1.63(d,2H)。
synthesis examples 2 to 35
1) Synthesis of intermediate I
Each intermediate I was synthesized with reference to the procedure of step (1) in compound 1, except that starting material 3 was replaced with starting material III and starting material 4 was replaced with starting material IV. Wherein, the main raw materials adopted and each intermediate I correspondingly synthesized are shown in the table 2.
2) Synthesis of compounds
Compounds were synthesized according to the procedure of step (2) for compound 1, except that intermediate a was replaced with each intermediate II and intermediate 1 was replaced with each intermediate I.
The main raw materials used, the intermediate I of the corresponding synthesis, and the number, structure, final yield and mass spectra of the final synthesized compound are shown in table 3.
TABLE 3
Figure BDA0002466060080000351
Figure BDA0002466060080000361
Figure BDA0002466060080000371
Figure BDA0002466060080000381
Figure BDA0002466060080000391
In addition, fig. 2 is a nuclear magnetic hydrogen spectrum of compound 2, and nuclear magnetic data of compound 2 is:1H NMR(CD2Cl2,400MHz):8.06(d,1H),7.97(d,1H),7.77(s,1H),7.45-7.42(m,4H),7.37-7.34(m,6H),7.31-7.10(m,16H),7.07(d,1H),7.03-7.00(m,3H),6.90(t,1H),2.90(d,2H),2.56(d,2H),2.13(s,1H),1.89(s,2H),1.82(s,1H)，1.73(d,2H),1.65-1,61(m,4H)。
organic electroluminescent device production and evaluation examples
Preparation of red organic electroluminescent device
Example 1
The anode was prepared by the following procedure: the thickness of ITO is set as
Figure BDA0002466060080000393
The ITO substrate (manufactured by KANGNING) was cut into a size of 40mm (length) X40 mm (width) X0.7 mm (thickness), and a photolithography process was usedPrepared into an experimental substrate with a cathode, an anode and an insulating layer pattern, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002466060080000394
And a layer of NPB is vapor-deposited on the hole injection layer to form a thickness of
Figure BDA0002466060080000395
A first hole transport layer (HTL 1).
Then, compound 1 was vacuum-evaporated on the first hole transport layer to form a layer having a thickness of
Figure BDA0002466060080000396
And a second hole transport layer (HTL 2).
Then 4,4'-N, N' -dicarbazole-biphenol (abbreviated as "CBP") is evaporated on the second hole transport layer as a main body, and Ir (flq) is doped at the same time2(acac) wherein the host and dopant are formed to a thickness of 100:3 film-after ratio
Figure BDA0002466060080000397
The organic electroluminescent layer (EML).
DBimiBphen and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form the film with the thickness of
Figure BDA0002466060080000398
The Electron Transport Layer (ETL) of (2), Yb is deposited on the electron transport layer to form a layer having a thickness of
Figure BDA0002466060080000399
An Electron Injection Layer (EIL);
mixing magnesium (Mg) and silver (Ag) in a ratio of 1: 10, vacuum-evaporating on the electron injection layer to a thickness of
Figure BDA00024660600800003910
The cathode of (1).
Further, the cathode is deposited with a thickness of
Figure BDA00024660600800003911
Forming a capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Wherein, HAT-CN, NPB, CBP, Ir (flq)2The structural formulae of (acac), DbimiBphen and CP-1 are as follows:
Figure BDA0002466060080000392
Figure BDA0002466060080000401
examples 2 to 35
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compounds listed in table 4 were each used in place of compound 1 of example 1 in forming the second hole transport layer (HTL 2). For example, the organic electroluminescent device of example 2 was prepared using compound 2, the organic electroluminescent device of example 3 was prepared using compound 11, and the devices of examples 4 to 35 were prepared in this order.
Comparative examples 1 to 3
An organic electroluminescent device was fabricated by the same method as in example 1, except that TPD, and compound a and compound B were each used instead of compound 1 of example 1 in forming the second hole transport layer (HTL 2). That is, comparative example 1 produced an organic electroluminescent device using TPD, comparative example 2 produced an organic electroluminescent device using compound a, and comparative example 3 produced an organic electroluminescent device using compound B.
Wherein the structural formulas of TPD, compound A and compound B are as follows:
Figure BDA0002466060080000402
comparative example 4
An organic electroluminescent device was fabricated by the same method as example 1, except that compound C was used in forming the second hole transport layer (HTL 2). Wherein the structural formula of the compound C is as follows:
Figure BDA0002466060080000403
the organic electroluminescent devices of the above examples and comparative examples were analyzed for their performance (IVL and lifetime), and the results are shown in table 4; wherein the driving voltage, luminous efficiency, external quantum efficiency and color coordinate are 10mA/cm at constant current density2The test is carried out, and the service life of the T95 device is 20mA/cm at constant current density2The test was performed.
TABLE 4
Figure BDA0002466060080000411
Figure BDA0002466060080000421
With the results shown in table 4, compared with comparative examples 1 to 4, the working voltage of the organic electroluminescent devices prepared in examples 1 to 35 is reduced by at least 0.22V, the lifetime of the T95 device is improved by at least 7.8%, and the device efficiency is substantially equivalent to that of comparative examples 1 to 4. Specifically, the driving voltage of the organic electroluminescent device prepared in comparative example 2 was 4.12V, the lifetime of the T95 device was 502h, and the optimum performance was obtained for the organic electroluminescent devices of the respective comparative examples; the working voltage of the organic electroluminescent devices prepared in the embodiments 1 to 35 is 3.78 to 3.90V, which is at least 0.22V lower than that of the comparative example 2; the service life of the T95 device is 541-580 h, which is at least 7.8% longer than that of the device of comparative example 2. Therefore, when the nitrogen-containing compound is applied to the organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged under the condition of higher luminous efficiency, and the working voltage of the organic electroluminescent device is reduced.

Claims (12)

1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is shown in chemical formula 1:
Figure FDA0002466060070000011
wherein Ar is1、Ar2、Ar3、Ar4Equal to or different from each other, each independently selected from: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar1、Ar2、Ar3、Ar4the substituents on each of which are the same or different from each other and are each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
R1and R2Equal to or different from each other, each independently selected from: deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
n1represents R1Is a number of and n1Selected from 0, 1,2, 3 or 4; and when n is1When greater than 1, any two R1The same or different;
n2represents R2Is a number of and n2Selected from 0, 1 or 2; and when n is2When it is 2, two R2The same or different.
2. The nitrogen-containing compound according to claim 1,characterized in that Ar is1、Ar2、Ar3、Ar4Each independently selected from: a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.
3. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1、Ar2、Ar3、Ar4Each independently selected from the group consisting of groups represented by formulas i-1 through i-15:
Figure FDA0002466060070000012
Figure FDA0002466060070000021
wherein M is1Selected from a single bond or
Figure FDA0002466060070000022
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
H1selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms and alkylthio having 1 to 10 carbon atoms;
H2～H9、H21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
H10～H20、F1～F4each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, and heteroaryl having 3 to 18 carbon atoms;
h1～h21by hkIs represented by H1～H21With HkK is a variable and represents an arbitrary integer of 1 to 21, hkRepresents a substituent HkThe number of (2); wherein, when k is selected from 5 or 17, hkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1, 3,4, 6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when h iskWhen greater than 1, any two HkThe same or different;
K1selected from O, S, 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 or a cycloalkyl group having 3 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, N (H)25)、C(H26H27)、Si(H26H27) (ii) a 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 or a cycloalkyl group having 3 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.
4. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1Is substituted or unsubstituted Z1，Ar2Is substituted or unsubstituted Z2，Ar3Is substituted or unsubstituted Z3，Ar4Is substituted or unsubstituted Z4(ii) a Wherein, Z is unsubstituted1、Z2、Z3And Z4Each independently selected from the group consisting of:
Figure FDA0002466060070000031
substituted Z1、Z2、Z3And Z4Each independently has one or more substituents selected from deuterium, cyano, fluorine, carbon atom1-4 alkyl, 3-10 cycloalkyl, 1-4 alkoxy, 1-4 alkylthio, 3-7 trialkylsilyl and pyridyl.
5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1、Ar2、Ar3、Ar4Each independently selected from the group consisting of the following substituents:
Figure FDA0002466060070000032
Figure FDA0002466060070000041
6. the nitrogen-containing compound according to any one of claims 1 to 5, wherein the structure of the nitrogen-containing compound is represented by chemical formula 1-1 or chemical formula 1-2:
Figure FDA0002466060070000042
7. the nitrogen-containing compound according to any one of claims 1 to 5, wherein R is1、R2Each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, trialkylsilyl with 3-7 carbon atoms, aryl with 6-15 carbon atoms and heteroaryl with 5-12 carbon atoms.
8. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0002466060070000051
Figure FDA0002466060070000061
Figure FDA0002466060070000071
Figure FDA0002466060070000081
Figure FDA0002466060070000091
Figure FDA0002466060070000101
Figure FDA0002466060070000111
Figure FDA0002466060070000121
Figure FDA0002466060070000131
Figure FDA0002466060070000141
Figure FDA0002466060070000151
Figure FDA0002466060070000161
Figure FDA0002466060070000171
Figure FDA0002466060070000181
Figure FDA0002466060070000191
Figure FDA0002466060070000201
Figure FDA0002466060070000211
9. 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 8.
10. The electronic component according to claim 9, wherein the functional layer comprises a hole transport layer comprising the nitrogen-containing compound.
11. The electronic component according to claim 9 or 10, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
12. An electronic device comprising the electronic component according to any one of claims 9 to 11.
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