WO2022088865A1 - Nitrogen-containing compound, electronic element, and electronic apparatus - Google Patents

Abstract

The present application relates to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic element, and an electronic apparatus. The nitrogen-containing compound has a structure as represented by the following formula 1. In the nitrogen-containing compound, R₁ to R₈ are the same or different, and at least two of them are selected from groups as represented by formula 2. By means of the nitrogen-containing compound, the performance of the electronic element can be improved, and in particular, the performance of an organic electroluminescent device and a photoelectric conversion device can be improved.

Description

Nitrogen-containing compounds, electronic components and electronic devices

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the priority of the Chinese patent application with the application number CN202011173737.5 filed on October 28, 2020, the full content of the above Chinese patent application is hereby cited as a part of this application.

technical field

The present application relates to the technical field of organic materials, and in particular, to a nitrogen-containing compound, an electronic component and an electronic device.

Background technique

With the development of electronic technology and the progress of material science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally include a cathode and an anode disposed opposite to each other, 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 component 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 stacked in this order. When a voltage is applied to the cathode and anode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move to the organic light-emitting layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitation The excitons are in an excited state and release energy to the outside, so that the organic light-emitting layer emits light to the outside.

Although there are some organic materials that can be used to transport holes, it is still necessary to continue to develop new materials to further improve the performance of electronic components.

SUMMARY OF THE INVENTION

The purpose of the present application is to provide a nitrogen-containing compound, an electronic component and an electronic device, so as to improve the performance of the electronic component.

In order to realize the above-mentioned purpose of the invention, the application adopts the following technical solutions:

According to a first aspect of the present application, a nitrogen-containing compound is provided, and the structure of the nitrogen-containing compound is shown in formula 1:

R ₁ to R ₇ are the same or different, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-20 carbon atoms, and those represented by formula 2. The group shown; R ₁ to R ₇ have at least one group selected from the group shown in formula 2;

Each R is independently selected from _deuterium , halogen group, cyano group, heteroaryl group with 3-18 carbon atoms, aryl group with 6-18 carbon atoms, halogenated group with 6-20 carbon atoms Aryl, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, alkyl halide with 1-10 carbon atoms group, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, or a group represented by formula 2;

n represents the number of R ₈ , selected from 0, 1, 2, 3, 4 or 5; when n>1, any two R ₈ are the same or different;

Ar ₃ is selected from substituted or unsubstituted aryl groups with 6-12 carbon atoms;

Each of L, L ₁ and L ₂ is the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, and a substituted or unsubstituted group having 6-30 carbon atoms the heteroarylene;

Each Ar ₁ and Ar ₂ are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 6-24 carbon atoms;

Wherein, at least 2 of R ₁ -R ₈ are selected from the groups shown in formula 2; when formula 1 contains multiple groups shown in formula 2, any two Ls are the same or different, and any two Ls are the same or different. L ₁ are the same or different, any two L ₂ are the same or different, any two Ar ₁ are the same or different, any two Ar ₂ are the same or different;

The substituents in each of L, L ₁ , L ₂ , Ar ₁ and Ar ₂ are independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-20 carbon atoms, optionally replaced by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl aryl group with 6-20 carbon atoms, and 3- Trialkylsilyl group of 12, triarylsilyl group of carbon number 18-24, alkyl group of carbon number of 1-10, haloalkyl group of carbon number of 1-10, carbon number of 2-6 alkenyl, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkene with 5-10 carbon atoms base, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms , an arylthio group with a carbon number of 6-18, a phosphineoxy group with a carbon number of 6-18;

The substituents in Ar ₃ are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

According to a second aspect of the present application, an electronic component is provided, 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 first aspect of the present application. the nitrogen-containing compound;

Preferably, the functional layer includes a hole injection layer, and the hole injection layer includes the nitrogen-containing compound;

Preferably, the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound.

According to a third aspect of the present application, an electronic device is provided, including the electronic component described in the second aspect of the present application.

In the nitrogen-containing compound provided in the present application, a triarylamine structure is conjugated and connected to the core of N-phenyl-4-arylcarbazole. Both the carbazolyl group and the triarylamine group have good hole-transporting ability, and their hole-transporting ability can be further enhanced after the two are conjugated. The phenyl group and the aryl group at the 4th position connected to N on the core of N-phenyl-4-arylcarbazole can further expand the conjugation plane of the nitrogen-containing compound and enhance its conjugation system. The electron cloud density increases its hole transport ability. Not only that, in the core of N-phenyl-4-arylcarbazole, the phenyl group attached to N has steric competition with the hydrogen or substituent at the 1/8 position of carbazole, and the aryl group at the 4th position competes with carbazole. There is steric competition for the hydrogen or substituent at the 5-position of the azole; this makes the planes of the phenyl group attached to N and the aryl group at the 4-position deviate from the plane of the carbazole, which can adjust the degree of conjugation of nitrogen-containing compounds. The adjustment of the HOMO (highest occupied molecular orbital) energy level is realized, so that the HOMO energy level of the nitrogen-containing compound can be better matched with the electron blocking layer or the organic light-emitting layer, thereby further improving the efficiency of hole injection into the organic light-emitting layer. Not only that, the planes of the phenyl group on N and the aryl group at the 4th position are deviated from the plane of carbazole, which can improve the asymmetry of nitrogen-containing compounds, reduce the π-π stacking effect of nitrogen-containing compounds, and further improve the The film-forming property of the nitrogen-containing compound improves the thermal stability of the electronic component to which the nitrogen-containing compound is applied.

Description of drawings

The above and other features and advantages of the present application will become more apparent from the detailed description of example embodiments thereof with reference to the accompanying drawings.

FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

FIG. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.

FIG. 3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

FIG. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

The main components in the figure are described as follows:

100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer 360, the photoelectric conversion layer; 400, the first electronic device; 500, the second electronic device.

Detailed ways

Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments, however, can be embodied in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application 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 in order to give a thorough understanding of the embodiments of the present application.

In the figures, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus their detailed descriptions 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 in order to give a thorough understanding of the embodiments of the present application. However, one skilled in the art will appreciate that the technical solutions of the present application may be practiced without one or more of the specific details, or other methods, components, materials, etc. may be employed. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the present application.

The terms "comprising" and "having" are used to indicate an open-ended inclusive meaning and mean that there may be additional elements/components/etc. in addition to the listed elements/components/etc.

In this application,

Refers to the position of binding to other substituents or binding positions.

In this application, the number of carbon atoms of a group refers to the number of all carbon atoms. For example, in a substituted arylene group having 10 carbon atoms, all of the arylene group and the substituents thereon have 10 carbon atoms. Illustratively, 9,9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.

In this application, when no specific definition is provided otherwise, "hetero" refers to a functional group including at least 1 heteroatom such as B, N, O, S, Se, Si or P and the remaining atoms are carbon and hydrogen . An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.

In this application, the description methods “each independently is” and “are independently” and “are independently selected from” can be interchanged, and should be understood in a broad sense, which can either refer to In different groups, the specific options expressed between the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed between the same symbols do not affect each other. For example: in

Wherein, each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, fluorine, chlorine" in the description, its meaning is: formula Q-1 represents that there are q substituents R on the benzene ring ", each R" can be the same or different, and the options of each R" do not affect each other; formula Q-2 indicates that each benzene ring of biphenyl has q substituents R", and the two benzene rings have q substituents R". The number q of R" substituents may be the same or different, and each R" may be the same or different, and the options of each R" do not affect each other.

In this application, the term "substituted or unsubstituted" means no substituents or substituted with one or more substituents. The substituents include, but are not limited to, deuterium, halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio group, silyl group, alkylamino group, cycloalkyl group, heterocyclic group.

In this application, "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur. For example, "optionally, two substituents attached to the same atom are attached to each other to form a saturated or unsaturated 5-18 membered aliphatic ring or a 5-18 membered aromatic ring with the atom to which they are commonly attached", Meaning: When there are two substituent groups attached to the same atom, the two substituent groups can exist independently of each other, or they can be attached to each other to form saturated or unsaturated 5-18-membered aliphatic with the atom to which they are commonly attached family ring or 5-18 membered aromatic ring.

In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups can have 3-10 carbon atoms, and a numerical range such as "3 to 10" refers to each integer in the given range; Cycloalkyl of 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. Cycloalkyl groups can also be divided into two rings sharing one carbon atom - spiro rings, two rings sharing two carbon atoms - fused rings and two rings sharing more than two carbon atoms - bridged rings. Additionally, cycloalkyl groups may be substituted or unsubstituted. In some embodiments, the cycloalkyl group is a 5- to 10-membered cycloalkyl group, and in other embodiments, the cycloalkyl group is a 5- to 8-membered cycloalkyl group. In the present application, specific examples of cycloalkyl groups having 3 to 10 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl groups can be monocyclic aryl groups (eg, phenyl) or polycyclic aryl groups, in other words, aryl groups can be monocyclic aryl groups, fused-ring aryl groups, two or more monocyclic aryl groups conjugated through carbon-carbon bonds. Cyclic aryl groups, monocyclic aryl groups and fused-ring aryl groups linked by carbon-carbon bond conjugation, two or more fused-ring aryl groups linked by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation may also be considered aryl groups in the present application. Among them, the fused ring aryl group may include, for example, a bicyclic fused aryl group (eg, naphthyl), a tricyclic fused aryl group (eg, phenanthrenyl, fluorenyl, anthracenyl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10] phenanthryl, pyrenyl, benzofluoranthene,

Base et al. The "substituted or unsubstituted aryl group" of the present application contains 6-30 carbon atoms, in some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group is 6-25, in other embodiments The number of carbon atoms in the substituted or unsubstituted aryl group is 6-18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl group is 6-13. For example, in the present application, the number of carbon atoms of a substituted or unsubstituted aryl group can be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30 , of course, the number of carbon atoms can also be other numbers, which will not be listed here. In this application, biphenyl can be understood as a phenyl substituted aryl group, and can also be understood as an unsubstituted aryl group.

In the present application, the arylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the aryl group.

In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, Cycloalkyl, alkoxy, alkylthio and other groups are substituted. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, and the like. It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with a carbon number of 18 refers to the aryl group and its substituents. The total number of carbon atoms of the substituents is 18.

In this application, specific examples of aryl groups as substituents include but are not limited to: phenyl, naphthyl, anthracenyl, phenanthryl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorene base and so on.

In this application, the fluorenyl group can be substituted, and the two substituent groups can be combined with each other to form a spiro structure. Specific examples include but are not limited to the following structures:

In this application, heteroaryl refers to a monovalent aromatic ring or its derivatives containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be B, O, N, P, Si, At least one of Se and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, a heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems linked by carbon-carbon bonds, and any aromatic The ring system is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, 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 Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene thienyl, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl and N-arylcarbazole base (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), etc., not limited to this. Among them, thienyl, furyl, phenanthroline, etc. are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl and N-heteroarylcarbazolyl are polycarbazolyl groups conjugated through carbon-carbon bonds. Heteroaryl of ring system type. The "substituted or unsubstituted heteroaryl" of the present application contains 3-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3-25, and in others The number of carbon atoms in the substituted or unsubstituted heteroaryl group in embodiments may be 3-20, and the number of carbon atoms in the substituted or unsubstituted heteroaryl group in other embodiments may be 12-20. For example, the number of carbon atoms can be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30. Of course, the number of carbon atoms can also be are other quantities, which will not be listed here.

In the present application, the heteroarylene group referred to refers to a divalent group formed by the further loss of one hydrogen atom from the heteroaryl group.

In this application, a substituted heteroaryl group may be a heteroaryl group in which one or more than two hydrogen atoms are replaced by, for example, a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkane group group, cycloalkyl, alkoxy, alkylthio and other groups. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, N-phenylcarbazolyl, and the like. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

In the present application, specific examples of heteroaryl groups as substituents include but are not limited to: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthroline, etc. .

In this application, the explanation for aryl can be applied to arylene, the explanation for heteroaryl also applies to heteroarylene, the explanation for alkyl can be applied to alkylene, and the explanation for cycloalkyl can be Applied to cycloalkylene.

In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl group. The 6-10 membered aromatic ring refers to benzene ring, indene ring and naphthalene ring.

"Ring" in this application includes saturated rings, unsaturated rings; saturated rings are cycloalkyl, heterocycloalkyl, unsaturated rings are cycloalkenyl, heterocycloalkenyl, aryl and heteroaryl.

In the present application, the alkyl group with 1-10 carbon atoms may include straight-chain alkyl groups with 1-10 carbon atoms and branched-chain alkyl groups with 3-10 carbon atoms. 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 base, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl and the like.

In the present application, halogen groups 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, trimethylsilyl, triethylsilyl, and the like.

In the present application, specific examples of the triarylsilyl group having 18 to 24 carbon atoms include, but are not limited to, triphenylsilyl and the like.

In the present application, the non-positioning connecting bond refers to the single bond extending from the ring system

It means that one end of the linking bond can be connected to any position in the ring system through which the bond runs, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (X), the naphthyl group represented by the formula (X) is connected with other positions of the molecule through two non-positioned linkages running through the bicyclic ring. )-any possible connection mode shown by formula (X-10).

For example, as shown in the following formula (X'), the phenanthrene represented by the formula (X') is connected to other positions of the molecule through a non-positioned link extending from the middle of one side of the benzene ring, and the meaning it represents, It includes any possible connection modes shown by formula (X'-1)-formula (X'-4).

A non-positioned substituent in the present application refers to a substituent attached through a single bond extending from the center of the ring system, which means 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 group represented by the formula (Y) is connected to the quinoline ring through a non-positioning link, and the meanings represented by the formula (Y-1)- Any possible connection mode shown by formula (Y-7).

A first aspect of the present application provides a nitrogen-containing compound, and the structure of the nitrogen-containing compound is shown in formula 1:

R ₁ to R ₇ are the same or different, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-20 carbon atoms, and those represented by formula 2. The group shown; R ₁ to R ₇ have at least one group selected from the group shown in formula 2;

Each R is independently selected from _deuterium , halogen group, cyano group, heteroaryl group with 3-18 carbon atoms, aryl group with 6-18 carbon atoms, halogenated group with 6-20 carbon atoms Aryl, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, alkyl halide with 1-10 carbon atoms group, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, or a group represented by formula 2;

n represents the number of R ₈ , selected from 0, 1, 2, 3, 4 or 5; when n>1, any two R ₈ are the same or different;

Ar ₃ is selected from substituted or unsubstituted aryl groups with 6-12 carbon atoms;

Each of L, L ₁ , L ₂ is the same or different, and is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted group with 6-30 carbon atoms the heteroarylene;

Each Ar ₁ and Ar ₂ are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 6-24 carbon atoms;

Wherein, at least 2 of R ₁ -R ₈ are selected from the groups shown in formula 2; when formula 1 contains multiple groups shown in formula 2, any two Ls are the same or different, and any two Ls are the same or different. L ₁ are the same or different, any two L ₂ are the same or different, any two Ar ₁ are the same or different, any two Ar ₂ are the same or different;

The substituents in each of L, L ₁ , L ₂ , Ar ₁ and Ar ₂ are independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-20 carbon atoms, optionally replaced by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl aryl group with 6-20 carbon atoms, and 3- Trialkylsilyl group of 12, triarylsilyl group of carbon number 18-24, alkyl group of carbon number of 1-10, haloalkyl group of carbon number of 1-10, carbon number of 2-6 alkenyl, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkene with 5-10 carbon atoms base, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms , an arylthio group with a carbon number of 6-18, a phosphineoxy group with a carbon number of 6-18;

The substituents in Ar ₃ are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

In the nitrogen-containing compound provided in the present application, a triarylamine structure is conjugated and connected to the core of N-phenyl-4-arylcarbazole. Both the carbazolyl group and the triarylamine group have good hole-transporting ability, and their hole-transporting ability can be further enhanced after the two are conjugated. The phenyl group and the aryl group at the 4th position connected to N on the core of N-phenyl-4-arylcarbazole can further expand the conjugation plane of the nitrogen-containing compound and enhance its conjugation system. The electron cloud density increases its hole transport ability. Not only that, in the core of N-phenyl-4-arylcarbazole, the phenyl group attached to N has steric competition with the hydrogen or substituent at the 1/8 position of carbazole, and the aryl group at the 4th position competes with carbazole. There is steric competition for the hydrogen or substituent at the 5-position of the azole; this makes the planes of the phenyl group attached to N and the aryl group at the 4-position deviate from the plane of the carbazole, which can adjust the degree of conjugation of nitrogen-containing compounds. The adjustment of the HOMO (highest occupied molecular orbital) energy level is realized, so that the HOMO energy level of the nitrogen-containing compound can be better matched with the electron blocking layer or the organic light-emitting layer, thereby further improving the efficiency of hole injection into the organic light-emitting layer. Not only that, the planes of the phenyl group on N and the aryl group at the 4th position are deviated from the plane of carbazole, which can improve the asymmetry of nitrogen-containing compounds, reduce the π-π stacking effect of nitrogen-containing compounds, and further improve the The film-forming property of the nitrogen-containing compound improves the thermal stability of the electronic component to which the nitrogen-containing compound is applied.

Optionally, R ₁ to R ₇ are the same or different, and are each 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 formula 2.

Optionally, each R is independently selected from _deuterium , fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl Butyl, cyclohexyl, cyclopentyl, adamantyl, phenyl, naphthyl, biphenyl, fluorenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or formula 2 shown in the group.

In one embodiment of the present application, R ₁ to R ₄ have at most one group selected from the group shown in formula 2, and R ₅ to R ₇ have at most one group selected from the group shown in formula 2, when n When >1, each R ₈ has at most one group selected from the group represented by formula 2.

In an embodiment of the present application, among R ₁ to R ₈ , a total of 2 are groups represented by formula 2, and the rest are hydrogen.

In one embodiment of the present application, R ₁ to R ₈ are the same or different, and each is independently selected from hydrogen or the group represented by formula 2.

In the present application, the nitrogen-containing compound is selected from the compounds represented by the following formulas 1-1 to 1-3:

Preferably, the Ar ₃ is selected from phenyl, naphthyl, and biphenyl.

In one embodiment of the present application, each L, L ₁ and L ₂ are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-15 carbon atoms, a carbon atom number is 12-20 substituted or unsubstituted heteroarylene.

In another embodiment of the present application, each L, L ₁ and L ₂ are the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dimethylfluorenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted Carbazolylylene, substituted or unsubstituted N-phenylcarbazolylidene.

Optionally, the substituents in each of L, L ₁ and L ₂ are the same or different, and are independently selected from deuterium, halogen groups, alkyl groups with 1-5 carbon atoms, and 6- 12 aryl.

Specifically, the substituents in each of L, L ₁ and L ₂ include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, Naphthyl, biphenyl, phenanthryl, etc.

In an embodiment of the present application, each L, L ₁ and L ₂ are the same or different, and each is independently selected from a single bond or a substituted or unsubstituted group W; the unsubstituted group W is selected from the following groups Formed group:

in,

Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, and phenanthrenyl; when the number of substituents in group W is greater than 1, the substituents are the same or different.

Optionally, each L, L ₁ and L ₂ are the same or different, and each is independently selected from the group consisting of a single bond or the following substituents:

In one embodiment of the present application, each of Ar ₁ and Ar ₂ is the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, and substituted with 12-20 carbon atoms. or unsubstituted heteroaryl.

Optionally, the substituents in each of Ar ₁ and Ar ₂ are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, aryl group with 6-20 carbon atoms. group, heteroaryl group with 12-18 carbon atoms.

Specifically, the substituents in each of Ar ₁ and Ar ₂ include but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl , biphenyl, terphenyl, phenanthrenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, carbazolyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzoyl Thienyl, etc.

Preferably, each Ar ₁ and Ar ₂ are the same or different, and are each independently selected from substituted or unsubstituted aryl groups with 6-15 carbon atoms, substituted or unsubstituted heteroaryl groups with 12-18 carbon atoms base.

In another embodiment of the present application, each Ar ₁ and Ar ₂ are the same or different, and each is independently selected from a substituted or unsubstituted group V; the unsubstituted group V is selected from the group consisting of the following groups:

in,

Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, terphenyl; when the number of substituents in group V is greater than 1, the substituents are the same or different.

Optionally, each Ar ₁ and Ar ₂ are the same or different, and each is independently selected from the group consisting of the following substituents:

In some embodiments, in the formula 2,

The groups shown are each independently selected from the group consisting of:

Optionally, the nitrogen-containing compound is selected from the group consisting of:

The present application also provides an electronic component, the electronic component includes an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer includes the above-mentioned nitrogen-containing compound.

The nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer, so as to improve the voltage characteristics, efficiency characteristics or lifetime characteristics of electronic components. Optionally, an organic film layer comprising the nitrogen-containing compound of the present application is located 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. Further, the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound of the present application; or the functional layer includes a hole injection layer, and the hole injection layer includes the nitrogen-containing compound of the present application; or the functional layer includes The hole transport layer and the hole injection layer, and both the hole transport layer and the hole injection layer contain the nitrogen-containing compound of the present application.

The electronic component of the present application may be, for example, an organic electroluminescence device or a photoelectric conversion device. For an organic electroluminescent device, its functional layer may include an organic light-emitting layer as an energy conversion layer; for a photoelectric conversion device, its 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 can 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 other colored organic electroluminescent devices. Electroluminescent devices.

As shown in FIG. 1 , the organic electroluminescent device includes 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 includes the nitrogen-containing compound provided in the present application.

Optionally, the functional layer 300 includes a hole injection layer 310 , and the hole injection layer 310 is disposed on the surface of the anode 100 close to the organic light-emitting layer 330 .

Optionally, the functional layer 300 includes a hole transport layer 321 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 sandwiched between the hole transport layer 321 and the anode 100 .

In a specific embodiment, the hole injection layer 310 includes the nitrogen-containing compound provided in the present application. 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 adjustment 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 another specific embodiment, the hole transport layer 321 contains the nitrogen-containing compound provided in the present application, so as to improve the hole transport ability in the organic electroluminescence device, thereby improving the luminous efficiency of the organic electroluminescence device, and Reduce the driving voltage of organic electroluminescent devices. Optionally, the hole transport layer 321 may be composed of the nitrogen-containing compound of the present application.

Optionally, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); Combined metals and oxides such as ZnO:Al or _SnO2 :Sb; or conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene ](PEDT), polypyrrole and polyaniline, but not limited thereto. It is preferable to include a transparent electrode comprising indium tin oxide (ITO) as an anode.

Optionally, 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. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the organic light-emitting layer 330. Host material, the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

The host material of the organic light-emitting layer 330 may be metal chelate compounds, bis-styryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not specifically limited in this 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 are not specially made in this application. limit. In one embodiment of the present application, the guest material of the organic light-emitting layer 330 may be BD-01.

Optionally, the cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/ Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca, but not limited thereto. Preferably, a metal electrode comprising an Mg-Ag alloy is included as the cathode.

Optionally, as shown in FIG. 1 , an electron transport layer 340 may also be disposed between the cathode 200 and the organic light-emitting layer 330 . The electron transport layer 340 may be a single-layer structure or a multi-layer structure, which may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline Derivatives or other electron transport materials, which are not specifically 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 also be disposed between the anode 100 and the organic light-emitting layer 330 to enhance the ability of injecting holes into the organic light-emitting layer 330 . The electron blocking layer 322 can 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 also be disposed between the cathode 200 and the electron transport layer 340 to enhance the capability of injecting electrons into the electron transport layer 340 . The electron injection layer 350 may include inorganic materials such as alkali metal sulfide and alkali metal halide, or may include a complex compound of alkali metal and organic matter. 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. As shown in FIG. 3 , the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a function disposed between the anode 100 and the cathode 200 Layer 300; the functional layer 300 includes the nitrogen-containing compound provided in this application. The functional layer includes a photoelectric conversion layer 360 as an energy conversion layer.

Optionally, the nitrogen-containing compound provided in the present application can be used to form at least one organic thin layer in the functional layer 300 to improve the performance of the photoelectric conversion device, especially the open circuit voltage of the photoelectric conversion device or the photoelectric conversion device. Conversion efficiency.

Optionally, 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. Wherein, the hole transport layer 321 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided by the present application and other materials.

Optionally, the functional layer 300 includes a hole injection layer, and the hole injection layer includes 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 serving as an energy conversion layer, an electron transport layer 340 and a cathode that are stacked in sequence. 200.

Alternatively, the photoelectric conversion device may be a solar cell, especially 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 that are stacked in sequence, wherein the hole transport layer 321 The nitrogen-containing compounds of the present application are included.

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 , which are sequentially stacked and arranged as an energy source. The photoelectric conversion layer 360 , the electron transport layer 340 and the cathode 200 of the conversion layer. The hole injection layer contains the nitrogen-containing compound of the present application.

The present application also provides an electronic device, which includes the above-mentioned electronic components.

According to an 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 above-mentioned organic electroluminescence device. The electronic device may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, and the like. Since the electronic device has the above-mentioned organic electroluminescence device, it has the same beneficial effects, which will not be repeated here.

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-mentioned photoelectric conversion device. The electronic device may be, for example, a solar power generation device, a light detector, a fingerprint identification device, an optical module, a CCD camera, or other types of electronic devices. Since the electronic device has the above-mentioned photoelectric conversion device, it has the same beneficial effect, which is not repeated here.

Hereinafter, the present application will be further described in detail through examples. However, the following examples are merely illustrative of the present application, and do not limit the present application.

Synthesis of Intermediates:

To a dry and nitrogen purged round bottom flask was added 1-bromo-2-iodo-3-chlorobenzene (50.0 g, 157.5 mmol), phenylboronic acid (19.2 g, 157.5 mmol), tetrakis(triphenylphosphine) Palladium (9.1 g, 7.8 mmol), tetrabutylammonium bromide (2.5 g, 7.8 mmol), potassium carbonate (65.2 g, 472.6 mmol), toluene (400 mL), ethanol (200 mL), deionized water (100 mL), The temperature was raised to 75°C under stirring and kept for 8 h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirred for 15 minutes, the organic phase was separated, anhydrous magnesium sulfate was added to dry, and the solvent was removed under reduced pressure; the obtained The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as mobile phase to obtain SM-D (35.8 g, yield 85%).

Into a round-bottomed flask that was dried and replaced with nitrogen, SM-D (35.8 g, 133.8 mmol) and tetrahydrofuran (400 mL) were added, and the temperature was lowered to minus 78 °C, and n-butyllithium (12.8 g, 200.7 mmol) was added dropwise. After the addition was completed, the temperature was kept at minus 78° C. for 30 minutes, and then trimethyl borate (41.7 g, 401.4 mmol) was added dropwise. The temperature was raised to room temperature and stirred for 12 h, and then an aqueous hydrochloric acid solution was added to adjust the pH to neutral. The obtained reaction solution was filtered to obtain a crude product, and the crude product was recrystallized from n-heptane (600 mL) to obtain SM-D-1 (19.6 g, yield 63%).

With reference to the synthetic method of intermediate SM-D, in the following table 1, reactant Q replaces phenylboronic acid to synthesize the intermediate shown in table 1 below:

Table 1: Synthesis of some intermediates

With reference to the synthetic method of intermediate SM-D, in the following table 2, reactant N replaces 1-bromo-2-iodo-3-chlorobenzene, and reactant M replaces phenylboronic acid to synthesize the intermediate shown in table 2 below:

Table 2: Synthesis of some intermediates

With reference to the synthesis method of intermediate SM-D-1, the intermediate (reactant) in the following table 3 replaces SM-D, and the intermediate shown in the following table 3 is synthesized:

Table 3: Synthesis of some intermediates

To a dry and nitrogen purged round-bottomed flask was added SM-D-1 (5.0 g, 26.0 mmol), 2,4-dichloronitrobenzene (6.1 g, 26.0 mmol), tetrakis(triphenylphosphine) Palladium (0.6 g, 0.5 mmol), tetrabutylammonium bromide (0.4 g, 1.3 mmol), potassium carbonate (10.8 g, 78.1 mmol), toluene (40 mL), ethanol (20 mL), deionized water (10 mL), The temperature was raised to 78°C under stirring and kept for 8 h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirred for 15 minutes, the organic phase was separated, anhydrous magnesium sulfate was added to dry, and the solvent was removed under reduced pressure; the obtained The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as mobile phase to obtain IM-A-1 (6.3 g; yield 70%).

In a round-bottomed flask that was dried and replaced with nitrogen, IMA-1 (5.0g 14.5mmol), triphenylphosphine (9.5g 36.3mmol), o-dichlorobenzene (40mL) were added, and the temperature was raised to 160 ° C under stirring, The reaction was carried out for 6 h; the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as the mobile phase to obtain IM-B-1 (2.7 g, the yield was 60 %).

Into a round-bottomed flask that was dried and purged with nitrogen, was added IM-B-1 (5.0 g, 16.0 mmol), iodobenzene (3.3 g, 16.3 mmol), cuprous iodide (0.61 g, 3.2 mmol), potassium carbonate (4.9 g, 35.2 mmol), 1,10-phenanthroline (1.2 g, 6.4 mmol), 18-crown-6 (0.4 g, 1.6 mmol), N,N-dimethylformamide (50 mL), The temperature was raised to 160 °C under stirring and kept for 8 h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, and stirred for 15 minutes, the organic phase was separated, and anhydrous magnesium sulfate was added to dry, and the solvent was removed under reduced pressure; the obtained The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as mobile phase to obtain IM-C-1 (4.9 g, yield 80%).

Referring to the synthesis method of IM-A-1, in Table 4 below, 2,4-dichloronitrobenzene is replaced by raw material A, and SM-D-1 is replaced by SM-X. The intermediates shown in Table 4 below were synthesized:

Table 4: Synthesis of some intermediates

With reference to the synthetic method of IM-B-1, in the following table 5, the raw material B replaces IM-A-1, and synthesizes the intermediate shown in the following table 5:

Table 5: Synthesis of some intermediates

With reference to the synthetic method of IM-C-1, in the following table 6, raw material C replaces IM-B-1, and synthesizes the intermediate shown in table 6 below:

Table 6: Synthesis of some intermediates

To a round-bottomed flask that was dried and purged with nitrogen, p-chlorophenylboronic acid (4.0 g, 25.7 mmol), IM-C-1 (5.0 g, 12.9 mmol), tetrakis(triphenylphosphine) palladium (0.3 g, 0.3 mmol) were added mmol), tetrabutylammonium bromide (0.18g, 0.6mmol), potassium carbonate (5.3g, 38.6mmol), toluene (40mL), ethanol (20mL), deionized water (10mL), and the temperature was raised to 75% under stirring ℃ for 8 h; then the reaction mixture was lowered to room temperature, deionized water (100 mL) was added, stirred for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was used in dichloromethane /n-heptane (volume ratio 1:3) was used as the mobile phase for purification by silica gel column chromatography to obtain IM-D-1 (5.6 g, yield 80%).

With reference to the synthetic method of IM-D-1, in the following table 7, raw material D replaces IM-C-1, SM-D replaces p-chlorobenzene boronic acid, and synthesizes the intermediate in the following table 7:

Table 7: Synthesis of some intermediates

To a dry and nitrogen purged round bottom flask was added biphenyl-2-boronic acid (51.6 g, 260.4 mmol), 2,4-dichloronitrobenzene (50.0 g, 260.4 mmol), tetrakis(triphenylphosphine) ) palladium (15.0 g, 13.0 mmol), tetrabutylammonium bromide (4.2 g, 13.0 mmol), potassium carbonate (107.9 g, 781.3 mmol), toluene (400 mL), ethanol (200 mL), deionized water (100 mL) , the temperature was raised to 75°C under stirring, and kept for 8 h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirred for 15 minutes, the organic phase was separated, and anhydrous magnesium sulfate was added to dry, and the solvent was removed under reduced pressure; The obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as a mobile phase to obtain IM-O-1 (56.5 g; yield 70%).

Into a round-bottomed flask that was dried and replaced with nitrogen, IM-O-1 (56.5 g, 182.4 mmol), triphenylphosphine (119.6 g, 456.0 mmol), o-dichlorobenzene (400 mL) were added, and the temperature was raised under stirring conditions. To 160 ° C, the reaction was carried out for 6 h; then silica gel was added to it to volatilize the liquid therein, and then dichloromethane/n-heptane (volume ratio 1:3) was used as the mobile phase for purification by silica gel column chromatography to obtain IM-P-1 ( 30.4 g, 60% yield).

Into a round-bottomed flask that was dried and purged with nitrogen, was added IM-P-1 (5.0 g, 17.9 mmol), p-chloroiodobenzene (4.4 g, 18.3 mmol), cuprous iodide (0.7 g, 3.6 mmol), Potassium carbonate (5.5g, 39.6mmol), 1,10-phenanthroline (1.3g, 7.2mmol), 18-crown-6 (0.5g, 1.8mmol), N,N-dimethylformamide (30mL) ), heated to 160°C under stirring, and kept for 8h; then the reaction mixture was lowered to room temperature, deionized water (200 mL) was added, stirred for 15 minutes, the organic phase was separated, anhydrous magnesium sulfate was added to dry, and the solvent was removed under reduced pressure; The obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (volume ratio 1:3) as a mobile phase to obtain IM-Q-1 (5.2 g, yield 75%).

With reference to the same method of IM-O-1, in the following table 8, raw material O replaces 2,4-dichloronitrobenzene, and SM-M replaces biphenyl-2-boronic acid to synthesize the intermediate of table 8 below:

Table 8: Synthesis of some intermediates

With reference to the same method of IM-P-1, the raw material P in the following table 9 replaces IM-O-1, and the intermediate shown in the following table 9 is synthesized:

Table 9: Synthesis of some intermediates

With reference to the synthetic method of IM-Q-1, in the following table 10, raw material Q replaces IM-P-1, and raw material N replaces p-chloroiodobenzene to synthesize the intermediate shown in table 10 below:

Table 10: Synthesis of some intermediates

IM-C-1 (5.0 g, 12.9 mmol), SM-1 (diphenylamine) (4.4 g, 25.8 mmol), and tris(dibenzylideneacetone)dipalladium (0.2 g, 0.25 mmol) were put into the reaction flask , 2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl (0.21 g, 0.5 mmol), sodium tert-butoxide (4.9 g, 51.6 mmol) and toluene solvent (50 mL), under nitrogen protection The temperature was raised to 110° C., and the mixture was heated under reflux and stirred for 8 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed three times with dichloromethane (50 mL) and water (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered. After filtration, the filtrate was passed through a short silica gel column and removed under reduced pressure. Solvent, the crude product was purified by recrystallization using dichloromethane/n-heptane system (volume ratio 1:3) to obtain compound 49 (6.3 g, 75%).

Referring to the synthesis method of compound 49, in Table 11 below, SM-Y was used to replace SM-1 (diphenylamine), and IM-X was used to replace IM-C-1. The compounds shown in Table 11 below were synthesized:

Table 11: Synthesis of some compounds

The above synthetic compounds were subjected to mass spectrometry analysis, and the mass spectral data of each compound were obtained as shown in Table 12 below:

Table 12: Mass Spectrometry Data for Some 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

NMR analysis was performed on the above-mentioned synthetic compounds, and the NMR data of each compound were obtained as shown in Table 13 below:

Table 13: Mass Spectrometry Data for Some Compounds

Preparation and Evaluation of Organic Electroluminescent Devices

Example 1: Preparation of blue organic electroluminescent device

The anode is prepared by the following process: the thickness is

The ITO substrate (manufactured by Corning) was cut into a size of 40mm×40mm×0.7mm, and a photolithography process was used to prepare it into an experimental substrate with patterns of cathodes, anodes and insulating layers. Ultraviolet ozone and O ₂ :N ₂ plasma were used for Surface treatment to increase the work function of the anode (experimental substrate) and remove scum.

Compound 49 and F4-TCNQ were co-evaporated on the experimental substrate (anode) at a mass ratio of 97%: 3% to form a thickness of

The hole injection layer (HIL) of , and compound 49 is evaporated on the hole injection layer to form a thickness of

The hole transport layer (HTL).

EB-01 was vacuum evaporated on the hole transport layer to form a thickness of

electron blocking layer.

On the electron blocking layer, BH-01 and BD-01 were co-evaporated in a mass ratio of 98%: 2% to form a thickness of

The blue light-emitting layer (EML).

ET-06 and LiQ were vapor-deposited at a film thickness ratio of 1:1 to form

Thick electron transport layer (ETL), Yb was evaporated on the electron transport layer to form a thickness of

Then, magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer with a film thickness ratio of 1:9 to form a thickness of

the cathode.

In addition, the thickness of the vapor deposition on the above-mentioned cathode is

of CP-5 to form an organic capping layer (CPL), thereby completing the fabrication of the organic light-emitting device.

Example 2-23

An organic electroluminescent device was fabricated by the same method as in Example 1, except that the compounds shown in the (HIL/HTL) column of Table 14 below were substituted for Compound 49 in forming the hole injection layer/hole transport layer.

Comparative Example 1

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound A-1 was used instead of Compound 49 when forming the hole injection layer/hole transport layer.

Comparative Example 2

An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A-2 was used instead of Compound 49 when forming the hole injection layer/hole transport layer.

Comparative Example 3

An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A-3 was used instead of Compound 49 when forming the hole injection layer/hole transport layer.

Comparative Example 4

An organic electroluminescent device was fabricated by the same method as in Example 1, except that Compound A-4 was used instead of Compound 49 when forming the hole injection layer/hole transport layer.

The material structures used in the above examples and comparative examples are as follows:

For the organic electroluminescent device prepared as above, the formation test was carried out under the condition of 20 mA/cm ² , and the test results are shown in Table 14.

Table 14: Performance test results of organic electroluminescent devices

From the results in Table 14, it can be seen that Examples 1-23 as the nitrogen-containing compounds of the hole injection layer and hole transport layer, and Comparative Examples 1-4 of the devices corresponding to the known compounds, the nitrogen-containing compounds used in the present application The above organic electroluminescent devices prepared as hole injection layer and hole transport layer materials have improved luminous efficiency (Cd/A) by at least 13.51%, external quantum efficiency EQE (%) by at least 13.49%, and lifetime by at least 6.81% %.

It should be understood that this application does not limit its application to the detailed structure and arrangement of components presented in this specification. The application is capable of other embodiments, of being implemented and of being carried out in various ways. The foregoing variations and modifications fall within the scope of the present application. It is to 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 in the text and/or drawings. All of these different combinations constitute various alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known to carry out the application, and will enable those skilled in the art to utilize the application.

Claims (12)

1. A nitrogen-containing compound, characterized in that the structure of the nitrogen-containing compound is shown in formula 1:

   

   R ₁ to R ₇ are the same or different, and are each independently selected from hydrogen, deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, cycloalkyl group having 3-20 carbon atoms, formula 2 the group shown;

   Each R is independently selected from _deuterium , halogen group, cyano group, heteroaryl group with 3-18 carbon atoms, aryl group with 6-18 carbon atoms, halogenated group with 6-20 carbon atoms Aryl, trialkylsilyl with 3-12 carbon atoms, triarylsilyl with 18-24 carbon atoms, alkyl group with 1-10 carbon atoms, alkyl halide with 1-10 carbon atoms group, a cycloalkyl group with 3-10 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, or a group represented by formula 2;

   n represents the number of R ₈ , selected from 0, 1, 2, 3, 4 or 5; when n>1, any two R ₈ are the same or different;

   Ar ₃ is selected from substituted or unsubstituted aryl groups with 6-12 carbon atoms;

   Each of L, L ₁ , L ₂ is the same or different, and is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, and a substituted or unsubstituted group with 6-30 carbon atoms the heteroarylene;

   Each Ar ₁ and Ar ₂ are the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 6-24 carbon atoms;

   Wherein, at least 2 of R ₁ -R ₈ are selected from the groups shown in formula 2; when formula 1 contains multiple groups shown in formula 2, any two Ls are the same or different, and any two Ls are the same or different. L ₁ are the same or different, any two L ₂ are the same or different, any two Ar ₁ are the same or different, any two Ar ₂ are the same or different;

   The substituents in each of L, L ₁ , L ₂ , Ar ₁ and Ar ₂ are independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3-20 carbon atoms, optionally replaced by 0, 1, 2, 3, 4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl aryl group with 6-20 carbon atoms, and 3- Trialkylsilyl group of 12, triarylsilyl group of carbon number 18-24, alkyl group of carbon number of 1-10, haloalkyl group of carbon number of 1-10, carbon number of 2-6 alkenyl, alkynyl with 2-6 carbon atoms, cycloalkyl with 3-10 carbon atoms, heterocycloalkyl with 2-10 carbon atoms, cycloalkene with 5-10 carbon atoms base, heterocycloalkenyl with 4-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, aryloxy with 6-18 carbon atoms , an arylthio group with a carbon number of 6-18, a phosphineoxy group with a carbon number of 6-18;

   The substituents in Ar ₃ are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.
2. The nitrogen-containing compound according to claim 1, wherein the Ar ₃ is selected from the group consisting of phenyl, naphthyl, and biphenyl.
3. The nitrogen-containing compound according to claim 1, wherein at most one of R ₁ to R ₄ is selected from the group shown in formula 2, and at most one of R ₅ to R ₇ is selected from the group shown in formula 2 group, when n>1, at most one of each R ₈ is a group represented by formula 2.
4. The nitrogen-containing compound according to claim 1, wherein each of L, L ₁ and L ₂ are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted alkane having 6-15 carbon atoms Aryl, substituted or unsubstituted heteroarylene with 12-20 carbon atoms;

   Preferably, the substituents in each of L, L ₁ and L ₂ are the same or different, and are independently selected from deuterium, halogen groups, alkyl groups with 1-5 carbon atoms, and 6- 12 aryl.
5. The nitrogen-containing compound according to claim 1, wherein each of L, L ₁ and L ₂ is the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted phenylene naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dimethylfluorenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolylidene, substituted or unsubstituted N-phenylcarbazolylidene;

   Preferably, the substituents in each of L, L ₁ and L ₂ are the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl base, phenyl, naphthyl, biphenyl, phenanthryl.
6. The nitrogen-containing compound according to claim 1, wherein each L, L ₁ and L ₂ are the same or different, and each is independently selected from a single bond or a substituted or unsubstituted group W; an unsubstituted group W is selected from the group consisting of:

   

   in,

   

   Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, and phenanthrenyl; when the number of substituents in group W is greater than 1, the substituents are the same or different.
7. The nitrogen-containing compound according to claim 1, wherein each Ar ₁ and Ar ₂ are the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, 12-20 substituted or unsubstituted heteroaryl;

   Preferably, the substituents in each of Ar ₁ and Ar ₂ are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-5 carbon atoms, aryl group with 6-20 carbon atoms , Heteroaryl with 12-18 carbon atoms.
8. The nitrogen-containing compound according to claim 1, wherein each Ar ₁ and Ar ₂ are the same or different, and are independently selected from substituted or unsubstituted groups V; the unsubstituted groups V are selected from the following groups The group consists of:

   

   

   in,

   

   Represents a chemical bond; the substituted group V has one or more substituents, each of which is independently selected from: deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl , tert-butyl, phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl; when the number of substituents in group V is greater than 1, the substituents are the same or different.
9. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:

   

   

   

   

   

   

   

   

   

   

   
10. An electronic component, characterized in that it comprises an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode;

    The functional layer comprises the nitrogen-containing compound of any one of claims 1-9;

    Preferably, the functional layer includes a hole injection layer, and the hole injection layer includes the nitrogen-containing compound;

    Preferably, the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound.
11. The electronic component according to claim 10, wherein the electronic component is an organic electroluminescence device or a solar cell.
12. An electronic device, characterized by comprising the electronic component according to claim 10 or 11.

Images