WO2023045729A1 - Nitrogen-containing compound, electronic component, and electronic apparatus - Google Patents

Abstract

The present application relates to a nitrogen-containing compound, an electronic component comprising same, and an electronic apparatus. The nitrogen-containing compound of the present application comprises a fluorenyl group, and benzocycloalkyl having rich electron density is introduced to a fluorenyl group 9 position. The nitrogen-containing compound is applied to an organic electroluminescent device, so that the performance of the device can be significantly improved.

Description

Nitrogen-containing compounds and electronic components and electronic devices

This application claims the priority of the Chinese patent application with application number CN202111136883.5 submitted on September 27, 2021, and the entire disclosure of the Chinese patent application is incorporated in this application by reference.

technical field

The application belongs to the technical field of organic materials, and in particular relates to a nitrogen-containing compound and electronic components and electronic devices containing the same.

Background technique

With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components generally include a cathode and an anode oppositely arranged, and a functional layer arranged 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 located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode that are stacked in sequence. 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 electroluminescent layer, and the holes on the anode side also move to the light-emitting layer, and the electrons and holes combine in the electroluminescent layer. Excitons are formed, and the excitons release energy outwards in an excited state, thereby making the electroluminescent layer emit light.

In the prior art, light-emitting layer materials that can be used in the preparation of organic electroluminescent devices are disclosed. However, compared with the application requirements of products, the performance, lifespan or efficiency of electronic components needs to be further improved. Therefore, it is still necessary to continue to develop new materials to further improve the performance of electronic components.

Contents of the invention

In view of the above-mentioned problems existing in the prior art, the purpose of the present application is to provide a nitrogen-containing compound and electronic components and electronic devices containing it. The nitrogen-containing compound can be used in organic electroluminescence devices to improve the performance of the devices.

According to the first aspect of the present application, a nitrogen-containing compound is provided, which has a structure represented by formula 1:

Wherein, Ring A is a 5-7 membered aliphatic ring;

One of _Y1 and _Y2 is

The other is selected from hydrogen, a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms; and when Y ₁ is hydrogen, L ₃ not a single key;

L ₁ , L ₂ , L ₃ and L ₄ are the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, arylene group with 3-30 carbon atoms substituted or unsubstituted heteroarylene;

Each _R1 and _R2 are the same or different from each other, and are independently selected from deuterium, an alkyl group with 1-12 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, and an alkyl group with 6-30 carbon atoms. Aryl, heteroaryl with 3-30 carbon atoms, alkoxy with 1-12 carbon atoms, haloalkyl with 1-12 carbon atoms, deuterated alkyl with 1-12 carbon atoms , Trialkylsilyl and triphenylsilyl groups with 3-12 carbon atoms;

Each _R is selected from deuterium or an alkyl group with 1-4 carbon atoms;

n ₁ represents the number of R ₁ , n ₁ is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n ₁ is greater than 1, any two R ₁ are the same or different, optionally, any Two adjacent R ₁ form a ring;

n ₂ represents the number of R ₂ , n ₂ is selected from 0, 1, 2 or 3; when n ₂ is greater than 1, any two R ₂ are the same or different;

n ₃ represents the number of R ₃ , n ₃ is selected from 0, 1, 2, 3, 4, 5 or 6; when n ₃ is greater than 1, any two R ₃ are the same or different;

Ar ₁ and Ar ₂ are the same or different from each other, and each is independently selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;

The substituents of L ₁ , L ₂ , L ₃ , L ₄ , Y ₁ , Y ₂ , Ar ₁ and Ar ₂ are the same or different, and are each independently selected from deuterium, cyano, nitro, halogen, hydroxyl, Alkyl with 1-12 carbon atoms, alkoxy with 1-12 carbon atoms, haloalkyl with 1-12 carbon atoms, deuterated alkyl with 1-12 carbon atoms, Cycloalkyl with 3-12 carbon atoms, heterocycloalkyl with 2-12 carbon atoms, aralkyl with 7-20 carbon atoms, heteroaralkyl with 2-20 carbon atoms, Aryl group with 6-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, alkoxy group with 1-12 carbon atoms, alkylthio group with 1-12 carbon atoms, 3-20 carbon atoms 12 trialkylsilyl groups, triphenylsilyl groups, aryloxy groups with 6-20 carbon atoms, and arylthio groups with 6-20 carbon atoms;

Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring.

According to the 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 includes the nitrogen-containing compound mentioned above.

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

The nitrogen-containing compound of the present application contains a fluorenyl group, and a benzocycloalkyl group with a rich electron cloud density is introduced into the 9-position of the fluorenyl group. The core structure has excellent hole transport ability and stereo characteristics, and holes are introduced into the core structure. The transport group-arylamine structure further greatly improves the hole transport efficiency of the compound. When the nitrogen-containing compound of the present application is used in the first hole transport layer or the second hole transport layer (i.e. hole adjustment layer) of an electronic component (such as an organic electroluminescence device), the electronic component has high luminous efficiency . In addition, the 9-position disubstituted fluorenyl group has better spatial characteristics and can avoid overlapping between molecular layers. Therefore, the thermal stability of the compound is improved, and the use in the functional layer of electronic components can increase the service life of the device.

Description of drawings

The accompanying drawings are used to provide a further understanding of the present application, and constitute a part of the description, together with the following specific embodiments, are used to explain the present application, but do not constitute a limitation to the present application.

Fig. 1 is a schematic structural view of an organic electroluminescence device according to an embodiment of the present application.

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

reference sign

100. Anode 200. Cathode 300. Functional layer 310. Hole injection layer

320. Hole transport layer 321. First hole transport layer 322. Second hole transport layer 330. Organic light-emitting layer

340, hole blocking layer 350, electron transport layer 360, electron injection layer 400, electronic device

Detailed ways

Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these examples are provided so that this application will be thorough and complete and will fully convey the concept of example embodiments communicated 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 application.

In a first aspect, the application provides a nitrogen-containing compound having a structure represented by formula 1:

Wherein, Ring A is a 5-7 membered aliphatic ring,

One of _Y1 and _Y2 is

The other is selected from hydrogen, a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms; and when Y ₁ is hydrogen, L ₃ not a single key;

L ₁ , L ₂ , L ₃ and L ₄ are the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, arylene group with 3-30 carbon atoms substituted or unsubstituted heteroarylene;

Each _R1 and _R2 are the same or different from each other, and are independently selected from deuterium, an alkyl group with 1-12 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, and an alkyl group with 6-30 carbon atoms. Aryl, heteroaryl with 3-30 carbon atoms, alkoxy with 1-12 carbon atoms, haloalkyl with 1-12 carbon atoms, deuterated alkyl with 1-12 carbon atoms , Trialkylsilyl or triphenylsilyl with 3-12 carbon atoms;

Each _R3 is independently selected from deuterium or an alkyl group with 1-4 carbon atoms;

n ₁ represents the number of R ₁ , n ₁ is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n ₁ is greater than 1, any two R ₁ are the same or different, optionally, any Two adjacent R ₁ form a ring;

n ₂ represents the number of R ₂ , n ₂ is selected from 0, 1, 2 or 3; when n ₂ is greater than 1, any two R ₂ are the same or different;

n ₃ represents the number of R ₃ , n ₃ is selected from 0, 1, 2, 3, 4, 5 or 6; when n ₃ is greater than 1, any two R ₃ are the same or different;

Ar ₁ and Ar ₂ are the same or different from each other, and each is independently selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;

The substituents in L ₁ , L ₂ , L ₃ , L ₄ , Y ₁ , Y ₂ , Ar ₁ and Ar ₂ are the same or different, and are independently selected from deuterium, cyano, nitro, halogen, and hydroxyl , an alkyl group with 1-12 carbon atoms, an alkoxy group with 1-12 carbon atoms, a haloalkyl group with 1-12 carbon atoms, a deuterated alkyl group with 1-12 carbon atoms, a carbon atom Cycloalkyl group with 3-12 carbon atoms, heterocycloalkyl group with 2-12 carbon atoms, aralkyl group with 7-20 carbon atoms, heteroaralkyl group with 2-20 carbon atoms, carbon atom Aryl group with 6-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, alkoxy group with 1-12 carbon atoms, alkylthio group with 1-12 carbon atoms, 3 carbon atoms -12 trialkylsilyl groups, triphenylsilyl groups, aryloxy groups with 6-20 carbon atoms, and arylthio groups with 6-20 carbon atoms;

Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring.

In this application, the terms "optional" and "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that these two substituents may or may not form a ring, including: the situation where two adjacent substituents form a ring and two A situation where adjacent substituents do not form a ring. For another example, "optionally, any two adjacent substituents in Ar ₂ form a saturated or unsaturated 5-13 membered ring" means that any two adjacent substituents in Ar ₂ can be connected to each other to form The 5- to 13-membered ring, or any two adjacent substituents in Ar ₂ may also exist independently. "Any two adjacent" may include two substituents on the same atom, and may also include one substituent on two adjacent atoms; wherein, when there are two substituents on the same atom, the two Two substituents can form a saturated or unsaturated spiro ring with the atom they are connected together; when two adjacent atoms have a substituent respectively, the two substituents can be fused to form a ring.

The "ring" in the present application includes saturated ring (ie aliphatic ring), unsaturated ring; saturated ring means cycloalkyl, heterocycloalkyl, unsaturated ring means cycloalkenyl, heterocycloalkenyl, aryl and heterocycloalkenyl Aryl. In the present application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl group. The 5-13 membered rings in this application are for example but not limited to: cyclopentane, cyclohexane, benzene ring, indene ring, adamantane, fluorene ring, naphthalene ring and the like. A 5-13 membered ring refers to a ring system formed by 5-13 ring atoms. For example, fluorene ring belongs to 13-membered ring, cyclohexane belongs to 6-membered ring, and adamantane belongs to 10-membered ring.

In the present application, the fluorenyl group may be substituted by one or two substituents, wherein any two adjacent substituents may combine with each other to form a substituted or unsubstituted spiro ring structure. Where the above fluorenyl groups are substituted, the substituted fluorenyl groups may be:

etc., but not limited to this.

In this application, the descriptions of "each...independently" and "...independently" and "...independently selected from" are interchangeable, and should be understood in a broad sense, which can mean In different groups, the specific options expressed by the same symbols do not affect each other, and it can also mean that in the same group, the specific options expressed by the same symbols do not affect each other. For example,"

Wherein, each q is independently 0, 1, 2 or 3, each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", and 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 means that there are q substituents R" on each benzene ring of biphenyl, and the R on the two benzene rings The number q of "substituents may be the same or different, each R" may be the same or different, and the options of each R" do not affect each other.

In the present application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. Wherein the above-mentioned substituent, ie Rc, can be, for example, deuterium, halogen group, cyano group, heteroaryl group, aryl group, trialkylsilyl group, alkyl group, haloalkyl group, cycloalkyl group and the like. The number of substitutions can be one or more.

In the present application, "plurality" means 2 or more, such as 2, 3, 4, 5, 6, etc.

In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms. For example, if L ₁ is a substituted arylene group with 12 carbon atoms, all the carbon atoms of the arylene group and the substituents thereon are 12.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocycle. The aryl group can be a single-ring aryl group (such as phenyl) or a polycyclic aryl group, in other words, the aryl group can be a single-ring aryl group, a condensed ring aryl group, two or more single-ring aryl groups connected by carbon-carbon bond conjugation. Cyclic aryl groups, single-ring aryl groups and condensed-ring aryl groups connected through carbon-carbon bond conjugation, and two or more fused-ring aryl groups connected through carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bond conjugation can also be regarded as an aryl group in the present application. Wherein, the fused ring aryl group may include, for example, a bicyclic fused aryl group (such as naphthyl), a tricyclic fused aryl group (such as a phenanthrenyl, a 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, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthene base,

Base etc. In the present application, the arylene group referred to refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

In this application, the terphenyl group includes

In this application, 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 with 18 carbon atoms refers to the aryl group and the substituent The total number of carbon atoms is 18.

In the present application, the substituted or unsubstituted aryl group may have 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6-30 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with a carbon number of 6-30. 25 substituted or unsubstituted aryl groups, in other embodiments, substituted or unsubstituted aryl groups are substituted or unsubstituted aryl groups with 6-18 carbon atoms, in other embodiments, substituted or unsubstituted aryl groups The aryl group is a substituted or unsubstituted aryl group with 6-15 carbon atoms.

In the present application, aryl groups as substituents of L ₁ , L ₂ , L ₃ , L ₄ , Y ₁ , Y ₂ , Ar ₁ and Ar ₂ are, for example but not limited to, phenyl, naphthyl, anthracenyl, phenanthrene Base, biphenyl, fluorenyl, dimethylfluorenyl, etc.

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. The 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 a plurality of aromatic ring systems connected by carbon-carbon bond conjugation, and any aromatic The ring system is an aromatic single ring or an aromatic fused ring. Exemplary, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, Acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyridine Azinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silfluorenyl, dibenzofuryl and N-phenylcarbazole group, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without being limited thereto.

In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 , 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30. In some embodiments, a substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 5-30, and in other embodiments, a substituted or unsubstituted heteroaryl is a total carbon A substituted or unsubstituted heteroaryl group with 12-18 atoms. In other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5-18. Another In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with 5-12 total carbon atoms.

In the present application, heteroaryl as substituents of L ₁ , L ₂ , L ₃ , L ₄ , Y ₁ , Y ₂ , Ar ₁ and Ar ₂ are, for example, but not limited to, pyridyl, carbazolyl, dibenzo Thienyl, dibenzofuryl.

In the present application, the substituted heteroaryl group can be one or more than two hydrogen atoms in the heteroaryl group replaced by such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, alkyl group , cycloalkyl, haloalkyl and other groups are substituted. 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, the alkyl group having 1-12 carbon atoms may include straight-chain alkyl groups having 1-12 carbon atoms and branched-chain alkyl groups having 3-12 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, normal Propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, etc.

In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

In the present application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, and the like.

In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

In the present application, the number of carbon atoms of the cycloalkyl group having 3-12 carbon atoms may be 3, 4, 5, 6, 7, 8, 10, 11 or 12, for example. Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

In this application, a non-positioning linkage refers to a single bond protruding from the ring system

It means that one end of the link can be connected to any position in the ring system that the bond runs through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is connected to other positions of the molecule through two unpositioned linkages that run through the bicyclic ring, and the meanings represented include the formula (f -1) to any possible connection shown in formula (f-10).

For another example, as shown in the following formula (X'), the dibenzofuryl group represented by the formula (X') is connected to other positions of the molecule through an unpositioned link extending from the middle of a benzene ring on one side, The meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4).

In this application, the nitrogen-containing compound has a structure as shown in formula 1-1 or 1-2:

In some embodiments of the present application, Ring A is a 5-7 membered saturated aliphatic ring.

Further, ring A is cyclopentane or cyclohexane.

In some embodiments of the present application, in formula 1

Has the structure shown in any one of formula (2-1) to (2-4):

In some embodiments of the present application, in formula 1

Has the structure shown in any one of formula (2-5) to (2-12):

In some embodiments, any two adjacent R ₁ form a benzene ring.

Optionally, Ar ₁ and Ar ₂ are the same or different, and each is independently selected from a substituted or unsubstituted aryl group with 6-25 carbon atoms, a substituted or unsubstituted heteroaryl group with 12-18 carbon atoms base.

Optionally, Ar ₁ and Ar ₂ are each independently selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, A substituted or unsubstituted aryl group having 22, 23, 24, 25 or 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

Optionally, the substituents in Ar ₁ and Ar ₂ are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-4 carbon atoms, and haloalkane with 1-4 carbon atoms group, a deuterated alkyl group with 1-4 carbon atoms, a cycloalkyl group with 5-10 carbon atoms, an aryl group with 6-12 carbon atoms, a heteroaryl group with 5-12 carbon atoms, A trialkylsilyl or triphenylsilyl group with 3-8 carbon atoms; optionally, any two adjacent substituents in _Ar1 form a saturated or unsaturated 5-13 membered ring; optionally Alternatively, any two adjacent substituents in Ar ₂ form a saturated or unsaturated 5-13 membered ring.

In some embodiments, Ar _{and Ar} are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted Substituted pyrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro[cyclopentane-1,9'-fluorenyl], substituted or unsubstituted spiro [Cyclohexane-1,9'-fluorenyl]yl, substituted or unsubstituted spiro[adamantan-1,9'-fluorenyl]yl, or substituted or unsubstituted groups selected from the following groups:

Optionally, the substituents in Ar _{and Ar} are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl Cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazole base.

In some embodiments, Ar _{and Ar} are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of:

The substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, cyclopentyl, Cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, phenyl, naphthyl, pyridyl, dibenzofuryl, dibenzothienyl or carbazolyl, and when the group When the number of substituents above W is greater than 1, each substituent is the same or different.

In a specific embodiment, Ar ₁ and Ar ₂ are each independently selected from the group consisting of the following groups:

Optionally, Ar _{and Ar} are each independently selected from the following groups:

In some embodiments, L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from a single bond, a substituted or unsubstituted arylene group with 6-18 carbon atoms, an arylene group with 12-18 carbon atoms Substituted or unsubstituted heteroarylene.

In some embodiments, L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from single bonds, substituted or unsubstituted arylenes with 6, 10, 12, 13, 14, 15, 18 carbon atoms A group, a substituted or unsubstituted heteroarylene group having 12, 16 or 18 carbon atoms.

Optionally, the substituents in L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, alkyl with 3-8 carbon atoms Trialkylsilyl group, fluoroalkyl group with 1-4 carbon atoms, aryl group with 6-12 carbon atoms or heteroaryl group with 5-12 carbon atoms.

Optionally, L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene , substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted carba Azolyl, or a subunit group formed by connecting two or three of the above subunits through a single bond.

In the compound of the present application, when Y ₁ is hydrogen, L ₃ is not a single bond.

Optionally, the substituents in L ₁ , L ₂ , L ₃ and L ₄ are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, Trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or pyridyl.

In some embodiments, L ₁ , L ₂ , L ₃ and L ₄ are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted group Q; wherein, the unsubstituted group Q is selected from the following The group consisting of:

The substituted group Q has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, and when the group When the number of substituents in Q is greater than 1, each substituent is the same or different.

In a specific embodiment, L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from single bonds or the following groups:

In some embodiments, L ₃ is a single bond, phenylene, or naphthylene.

Further, L ₃ is selected from a single bond or the following groups:

In some embodiments, L ₄ is a single bond, phenylene, or naphthylene.

Further, L ₄ is selected from a single bond or the following groups:

In a specific embodiment, one of Y ₁ and Y ₂ is

The other is selected from hydrogen, a substituted or unsubstituted aryl group with 6-25 carbon atoms, a substituted or unsubstituted heteroaryl group with 12-18 carbon atoms; and when Y ₁ is hydrogen, L ₃ Not a single key.

Optionally, the substituents in _Y1 and _Y2 are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-4 carbon atoms, haloalkane with 1-4 carbon atoms group, a deuterated alkyl group with 1-4 carbon atoms, a cycloalkyl group with 5-10 carbon atoms, an aryl group with 6-12 carbon atoms, a heteroaryl group with 5-12 carbon atoms, or A trialkylsilyl group with 3-8 carbon atoms.

In a specific embodiment, one of Y ₁ and Y ₂ is

The other is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl , substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl; and when Y ₁ is hydrogen, L ₃ is not a single bond.

Optionally, the substituents in Y _{and Y} are the same or different, and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuteromethyl, cyclopentyl , cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl .

In one embodiment, Y _is

_Y2 is selected from hydrogen.

In some embodiments, _Y2 is

_Y is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl, substituted or Unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl.

In some embodiments, each R _{and R} are the same or different from each other and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuteromethyl, cyclopentyl , cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuryl, dibenzothienyl or carbazolyl.

In some embodiments, n ₁ is 0.

In some embodiments, _n2 is 0.

In some embodiments, Y ₁ or Y ₂ is

and

selected from the group consisting of:

In some embodiments,

selected from the group consisting of:

In some embodiments, _Y2 is

In the structure shown, Y _is selected from the group consisting of the following groups:

In some more specific embodiments, _Y2 is

and is selected from the group consisting of the following structures:

_Y is selected from the group consisting of hydrogen or the following groups:

In a specific embodiment, Y ₂ is hydrogen, Y ₁ is

and is selected from the group consisting of:

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

In a second aspect, the present application provides an electronic component, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer contains the nitrogen-containing compound described in the first aspect of the present application.

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 lifespan and other characteristics of the device.

Optionally, the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound of the present application. Wherein, the hole transport layer can be composed of the nitrogen-containing compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials.

In one embodiment, the electronic component is an organic electroluminescent device, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is opposite to the The second hole transport layer is closer to the anode, wherein the second hole transport layer includes the nitrogen-containing compound.

According to a specific embodiment, the electronic component is an organic electroluminescent device. As shown in FIG. 1 , an organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, and an electron transport layer that are sequentially stacked. 350 , electron injection layer 360 and cathode 200 .

Optionally, a hole blocking layer 340 is disposed between the organic light emitting layer 330 and the electron transport layer 350 .

Optionally, the anode 100 includes the following anode material, which is optionally a material with a large work function (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 their alloys; 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 SnO ₂ :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. Optionally include a transparent electrode comprising indium tin oxide (ITO) as the anode.

In the present application, the first hole transport layer 321 may include one or more hole transport materials, and the first hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds , specifically can be selected from the following compounds or any combination thereof:

In one embodiment, the first hole transport layer 321 is composed of NPB.

Optionally, the second hole transport layer 322 can be selected from various triarylamine compounds, which is not particularly limited in this application. In one embodiment, the second hole transport layer 322 is composed of the compound of the present application.

The compound provided by this application has very high hole transport efficiency, which can improve the hole transport efficiency of hole transport layer 320; the organic compound provided by this application is a monoarylamine compound, which can improve the second hole transport layer 322 and organic The energy level difference between the light emitting layers 330 enables the second hole transport layer 322 to achieve a certain electron blocking effect and improve the lifetime of the organic electroluminescent device. On the other hand, the organic compound provided by the present application can have a suitable HOMO energy level, so that the HOMO energy levels between the second hole transport layer 322 and the first hole transport layer 321 are all small, and the first hole transport layer can be improved. The injection efficiency of the hole transport layer 321 is improved, and the driving voltage of the organic electroluminescence device is reduced.

Optionally, a hole injection layer 310 is also provided between the anode 100 and the first hole transport layer 321 to enhance the capability of injecting holes into the first hole transport layer 321 . The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;

In one embodiment of the present application, the hole injection layer 310 is composed of HAT-CN.

Optionally, the organic light-emitting layer 330 may consist 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 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, bistyryl derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials, which are not particularly limited in this application. The host material is divided into a single host material and a mixed host material. Wherein, the mixed host material includes HT-type host material and ET-type host material. Specifically, the host material is such as but not limited to,

In one embodiment, the host material may be GH-1.

The guest material of the organic light-emitting layer 330 may be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials, which are not specified in this application. limit. Guest materials are also called dopant materials or dopants. According to the emission type, it can be divided into fluorescent dopant and phosphorescent dopant. The dopant may be selected from a red phosphorescent dopant, a green phosphorescent dopant or a blue phosphorescent dopant. Among them, specific examples of guest materials include, but are not limited to,

In one embodiment, the guest material may be Ir(ppy) ₃ .

Optionally, a hole blocking layer 340 is further disposed between the organic light emitting layer 330 and the electron transport layer 350 to prevent holes from diffusing to the electron transport layer 350 . The hole blocking layer material can be a triarylamine compound. In one embodiment, the hole blocking layer material is HB-1.

The electron transport layer 350 can be a single-layer structure or a multilayer structure, which can include one or more electron transport materials, and the electron transport material can be selected from but not limited to, ET-1, LiQ, benzimidazole derivatives , oxadiazole derivatives, quinoxaline derivatives or other electron-transporting materials are not particularly limited in this application. The material of the electron transport layer 350 includes but not limited to the following compounds:

In one embodiment of the present application, the electron transport layer 350 is composed of ET-1 and LiQ.

In the present application, the cathode 200 may include a cathode material, which is a material with a small work function that facilitates injection of electrons into the functional layer. Specific examples of cathode materials 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 multilayer materials such as LiF/Al , Liq/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

Optionally, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350 . The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic compounds. For example, the electron injection layer 360 is Yb.

According to a specific embodiment, the organic electroluminescence device is a red light device or a green light device.

The third aspect of the present application provides an electronic device, including the organic electroluminescent device described in the second aspect of the present application.

According to an implementation manner, as shown in FIG. 2 , the provided electronic device is an electronic device 400 including the above-mentioned organic electroluminescence device. The electronic device 400 may be, for example, a display device, an illumination 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 lights, optical modules, and the like.

The synthesis method of the nitrogen-containing compound of the present application will be specifically described below in conjunction with the synthesis examples, but the present application is not limited thereby.

Synthetic example

Those skilled in the art will recognize that the chemical reactions described in this application can be used to suitably prepare many of the organic compounds of this application, and that other methods for preparing the compounds of this application are considered to be within the scope of this application Inside. For example, the synthesis of non-exemplified compounds according to the present application can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by using other known reagents in addition to those described in this application, or by incorporating Reaction conditions with some routine modifications. The compounds of the synthetic methods not mentioned in this application are all raw material products obtained through commercial channels.

1. Synthesis of intermediate TM-a-1

The raw material SM1 (20g, 74.8mmol), tetrahydrofuran (200mL) was added to the flask, and under nitrogen protection, at -80°C to -90°C with stirring, n-butyllithium (THF solution, 37.4mL, 74.8 mmol), the temperature of the dropping process was maintained at -80°C to -90°C, and the temperature was kept at -80°C to -90°C under stirring for 1h, and a tetrahydrofuran solution of 9-fluorenone (13.4g, 74.8mmol) was added dropwise under stirring, After dripping and keeping warm for 1 hour, the temperature was naturally raised to room temperature; the reaction liquid was washed with water, separated, the organic phase was washed with water and then dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; Purification by silica gel column chromatography gave white solid TM-a-1 (17.1 g; yield 62%). LC-MS (ESI, pos.ion) m/z = 369.2 [M+H] ⁺ .

Synthesize the intermediates listed in Table 1 with reference to the method of TM-a-1, the difference is that reactant A is used to replace 9-fluorenone, and reactant B is used to replace raw material SM1, the main raw materials used and the corresponding synthesized intermediates The structures and yields are shown in Table 1.

Table 1

2. Synthesis of intermediate TM-a-2

TM-a-1 (17.1g, 46.4mmol), pyridine (11g, 139.2mmol), dichloromethane (171mL) were added to the flask, and trifluoromethanesulfonic anhydride was added dropwise at 0°C under nitrogen protection (16.9g, 60.3mmol), dripping and keeping warm for 2h; the reaction solution was washed with water, separated, the organic phase was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product; the crude product was obtained using dichloromethane/n-heptyl The alkane system was purified by silica gel column chromatography to obtain a white solid TM-a-2 (15.1 g, yield 65%).

Synthesize the intermediates listed in Table 2 with reference to the method of TM-a-2. The difference is that TM-a-1 is replaced by reactant E. The main raw materials used and the corresponding synthetic intermediate structures and yields are shown in Table 2. shown.

Table 2

3. Synthesis of intermediate TM-a-3

TM-a-2 (15g, 29.96mmol), m-chlorophenylboronic acid (5.14g, 32.96mmol), tetrakis (triphenylphosphine) palladium (0.34g, 0.30mmol), potassium phosphate (9.04g, 65.9mmol) and 1,4-dioxane (150mL) were added to the flask, and stirred under reflux at 120°C for 8 hours under nitrogen protection; when the temperature was lowered to room temperature, the reaction solution was washed with water, separated, and the organic phase was washed with water and then washed with anhydrous Dry over magnesium sulfate, and remove the solvent under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane/n-heptane system to obtain a white solid TM-a-3 (8.05 g, yield 58%). LC-MS (ESI, pos.ion) m/z = 463.2 [M+H] ⁺ .

Synthesis of raw material SM-BH:

Pass nitrogen (0.100L/min) into the three-neck flask equipped with mechanical stirring, thermometer and spherical condenser for replacement for 15min, then add the raw materials SM-SS (11.50g, 45.68mmol) and pinacol borate (11.60g , 45.68mmol), potassium acetate (6.72g, 68.52mmol), x-Phos (0.43g, 0.91mmol), tris(dibenzylideneacetone)dipalladium (0.42g, 0.46mmol) and 1,4-dioxo Hexacyclic (155mL), heated to 75°C-85°C for 3h under reflux, after the reaction, cooled to room temperature. The reaction solution was extracted, the organic phase was dried with anhydrous magnesium sulfate, the solvent was removed from the filtrate under reduced pressure after filtration, the crude product was recrystallized and purified with toluene system, and the raw material SM-BH (9.59 g, yield 70%) was obtained by filtration.

Synthesize the intermediates listed in Table 3 with reference to the method of TM-a-3, the difference is that TM-a-2 is replaced by raw material C, m-chlorophenylboronic acid is replaced by raw material D, the main raw materials used and the corresponding synthetic intermediates The structure and yield of the body are shown in Table 3.

table 3

4. Synthesis of intermediate TM-a-4

Under nitrogen protection conditions, the intermediate TM-c-3 (6g, 12.96mmol), 4-chlorophenylboronic acid (2.43g, 15.55mmol) and tetrakis (triphenylphosphine) palladium (0.15g, 0.013mmol), Potassium carbonate (3.5g, 25.92mmol) and tetrabutylammonium bromide (2.09g, 6.48mmol) were dissolved in tetrahydrofuran (48mL) and water (12mL), heated to 60°C, stirred for 24h, and then cooled to room temperature, the reaction solution Wash with deionized water, extract with dichloromethane, separate the organic phase, wash with water, dry with anhydrous magnesium sulfate, remove the solvent under reduced pressure to obtain the crude product; the crude product is purified by silica gel column chromatography using dichloromethane/n-heptane system to obtain Intermediate TM-a-4 (3.49 g; yield 50%).

Intermediate TM-b-4 was synthesized with reference to the synthetic method of intermediate TM-a-4, except that 5-chloronaphthaleneboronic acid was used instead of 4-chlorophenylboronic acid to obtain TM-b-4 (3.67g, yield 48 %). The reaction formula is as follows:

5. Compound synthesis

Synthesis of Compound 106:

Under nitrogen protection conditions, TM-a-3 (7.5g, 16.19mmol), N-[1,1'-biphenyl-4-yl]-9,9-dimethyl-9H-fluorene-2- Amine (5.85g, 16.19mmol) and tris(dibenzylideneacetone)dipalladium (0.148g, 0.16mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.131g, 0.32mmol) and sodium tert-butoxide (2.33g, 24.29mmol) were heated to 108°C, stirred for 3h, then lowered to room temperature, the reaction solution was washed with acid water, separated, and the organic phase was washed with water and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using dichloromethane/n-heptane system to obtain white solid compound 106 (6.37 g, yield 50%). LC-MS (ESI, pos.ion) m/z = 788.4 [M+H] ⁺ .

The compounds in Table 4 below were prepared according to the synthesis method of compound 106, except that starting material 1 was used instead of TM-a-3, and starting material 2 was used instead of N-[1,1'-biphenyl-4-yl]-9,9 -Dimethyl-9H-fluoren-2-amine. The raw materials used, the number of the compound and its structure, synthesis yield, and mass spectrometry data are shown in Table 4.

Table 4

The NMR data of the compound are as follows:

Compound 2: ¹ H-NMR (400MHz, CDCl ₂ ): 7.83-7.81(d, 2H), 7.55-7.40(m, 16H), 7.09(t, 3H), 6.82(d, 2H), 6.78(d, 3H), 6.67(d, 1H), 6.52-6.48(m, 6H), 1.93-1.82(m, 2H), 1.73-1.62(m, 2H), 1.46(d, 12H).

Compound 106: ¹ H-NMR (400MHz, CDCl ₂ ): 7.83(d, 3H), 7.55-7.38(m, 11H), 7.13-7.05(m, 6H), 6.79(d, 2H), 6.70-6.58( m, 7H), 6.40-6.37 (m, 2H), 1.74-1.61 (m, 10H), 1.46 (d, 12H).

Fabrication and evaluation of organic electroluminescent devices:

Embodiment 1: the preparation of green organic electroluminescent device

The anode was prepared by the following process: the thickness of ITO was

The ITO substrate is cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and it is prepared into an experimental substrate with an anode and an insulating layer pattern by using a photolithography process, and ultraviolet ozone and O ₂ can be used : N ₂ plasma for surface treatment to increase the work function of the anode, and use organic solvents to clean the surface of the ITO substrate to remove impurities and oil on the surface of the ITO substrate.

HAT-CN was vacuum evaporated on the experimental substrate (anode) to form a thickness of

The hole injection layer (HIL), and then vacuum-evaporated NPB on the hole injection layer to form a thickness of

the first hole transport layer.

Compound 2 is vacuum evaporated on the first hole transport layer to form a thickness of

the second hole transport layer. Then on the second hole transport layer, the compound GH-1:Ir(ppy) ₃ is co-evaporated with a film thickness ratio of 90%:10%, forming a thickness of

organic light-emitting layer (EML, green light-emitting layer).

Compound HB-1 is vacuum evaporated on the organic light-emitting layer to form a thickness of

hole blocking layer. Then on the hole blocking layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form

Thick electron transport layer (ETL). Evaporate Yb on the electron transport layer to form a thickness of

Electron injection layer (EIL), then magnesium (Mg) and silver (Ag) are mixed at a deposition rate of 1:9, and vacuum evaporated on the electron injection layer to form a thickness of

of the cathode.

In addition, CP-1 was vacuum evaporated on the above-mentioned cathode to form a thickness of

The cover layer (CPL) of the green organic electroluminescent device is thus completed.

Examples 2-30

An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compounds in Table 5 were used instead of Compound 2 used in Example 1 when forming the second hole transport layer.

Comparative example 1-4

An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compounds A to D (structures are shown below) were used instead of Compound 2 used in Example 1 when forming the second hole transport layer.

Wherein, when preparing the organic electroluminescent devices of the above embodiments and comparative examples, the structural formulas of the main materials used are as follows.

The green organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-4 were tested for performance, specifically the IVL performance of the device was tested under the condition of 10mA/cm ² , and the lifetime of the _T95 device was 20mA/cm ² The test was carried out under certain conditions, and the test results are shown in Table 5.

Table 5 Green organic electroluminescent device performance test results

Referring to Table 5, it can be seen that the compounds described in this application are used as the second hole transport layer material in Examples 1-30, and the green organic electroluminescent devices prepared have the characteristics of low operating voltage, high efficiency and long life.

Specifically, compared with Examples 1-30 and Comparative Examples 1-4, the driving voltage of the device is reduced by at least 0.1V, the luminous efficiency is increased by at least 13.3%, and the T ₉₅ lifetime is increased by at least 15.9%.

Compared with the compound of the present application, the aryl group at the 9-position of the fluorenyl group in compound A lacks a fused cycloalkyl group, and the benzocycloalkyl group in compound B is not connected to the 9-fluorenyl group, and the hole transport ability of the two is insufficient; compound C In the middle benzocyclobutane, the ring tension of the compound is relatively large, and the thermal stability is insufficient, resulting in a decrease in device life; compound D contains two aromatic amine structures, and the HOMO energy level is too shallow, resulting in insufficient luminous efficiency and life of the device.

Those of ordinary skill in the art can understand that the above-mentioned implementation modes are specific examples for realizing the present application, and in practical applications, various changes can be made to it in form and details without departing from the spirit and spirit of the present application. scope.

Claims (14)

1. A nitrogen-containing compound, characterized in that the nitrogen-containing compound has a structure represented by formula 1:

   

   Wherein, Ring A is a 5-7 membered aliphatic ring;

   One of _Y1 and _Y2 is

   

   The other is selected from hydrogen, a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms; and when Y ₁ is hydrogen, L ₃ not a single key;

   L ₁ , L ₂ , L ₃ and L ₄ are the same or different from each other, and each is independently selected from a single bond, a substituted or unsubstituted arylene group with 6-30 carbon atoms, arylene group with 3-30 carbon atoms substituted or unsubstituted heteroarylene;

   Each _R1 and _R2 are the same or different from each other, and are independently selected from deuterium, an alkyl group with 1-12 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, and an alkyl group with 6-30 carbon atoms. Aryl, heteroaryl with 3-30 carbon atoms, alkoxy with 1-12 carbon atoms, haloalkyl with 1-12 carbon atoms, deuterated alkyl with 1-12 carbon atoms , Trialkylsilyl and triphenylsilyl groups with 3-12 carbon atoms;

   Each _R3 is independently selected from deuterium or an alkyl group with 1-4 carbon atoms;

   n ₁ represents the number of R ₁ , n ₁ is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n ₁ is greater than 1, any two R ₁ are the same or different, optionally, any Two adjacent R ₁ form a ring;

   n ₂ represents the number of R ₂ , n ₂ is selected from 0, 1, 2 or 3; when n ₂ is greater than 1, any two R ₂ are the same or different;

   n ₃ represents the number of R ₃ , n ₃ is selected from 0, 1, 2, 3, 4, 5 or 6; when n ₃ is greater than 1, any two R ₃ are the same or different;

   Ar ₁ and Ar ₂ are the same or different from each other, and each is independently selected from a substituted or unsubstituted aryl group with 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-30 carbon atoms;

   The substituents in L ₁ , L ₂ , L ₃ , L ₄ , Y ₁ , Y ₂ , Ar ₁ and Ar ₂ are the same or different, and are independently selected from deuterium, cyano, nitro, halogen, and hydroxyl , an alkyl group with 1-12 carbon atoms, an alkoxy group with 1-12 carbon atoms, a haloalkyl group with 1-12 carbon atoms, a deuterated alkyl group with 1-12 carbon atoms, a carbon atom Cycloalkyl group with 3-12 carbon atoms, heterocycloalkyl group with 2-12 carbon atoms, aralkyl group with 7-20 carbon atoms, heteroaralkyl group with 2-20 carbon atoms, carbon atom Aryl group with 6-20 carbon atoms, heteroaryl group with 3-20 carbon atoms, alkoxy group with 1-12 carbon atoms, alkylthio group with 1-12 carbon atoms, 3 carbon atoms -12 trialkylsilyl groups, triphenylsilyl groups, aryloxy groups with 6-20 carbon atoms or arylthio groups with 6-20 carbon atoms;

   Optionally, in Ar ₁ and Ar ₂ , any two adjacent substituents form a ring.
2. The nitrogen-containing compound according to claim 1, wherein, in formula 1

   

   Has the structure shown in any one of formula (2-1) to (2-4):

   
3. The nitrogen-containing compound according to claim 1, wherein, Ar ₁ and Ar ₂ are the same or different, and are each independently selected from substituted or unsubstituted aryl groups with 6-25 carbon atoms, 12-25 carbon atoms 18 substituted or unsubstituted heteroaryl;

   Optionally, the substituents in Ar ₁ and Ar ₂ are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-4 carbon atoms, and haloalkane with 1-4 carbon atoms group, a deuterated alkyl group with 1-4 carbon atoms, a cycloalkyl group with 5-10 carbon atoms, an aryl group with 6-12 carbon atoms, a heteroaryl group with 5-12 carbon atoms, A trialkylsilyl or triphenylsilyl group with 3-8 carbon atoms; optionally, any two adjacent substituents in _Ar1 form a saturated or unsaturated 5-13 membered ring; optionally Alternatively, any two adjacent substituents in Ar ₂ form a saturated or unsaturated 5-13 membered ring.
4. The nitrogen-containing compound according to claim 1, wherein Ar _{and Ar} are each independently selected from a substituted or unsubstituted group W, and the unsubstituted group W is selected from the group consisting of the following groups:

   

   The substituted group W has one or more substituents, and the substituents are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, triphenylsilyl, trifluoromethyl, cyclopentyl, Cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, adamantyl, phenyl, naphthyl, pyridyl, dibenzofuryl, dibenzothienyl or carbazolyl, and when the group When the number of substituents above W is greater than 1, each substituent is the same or different.
5. The nitrogen-containing compound according to claim 1, wherein L ₁ , L ₂ , L ₃ and L ₄ are the same or different from each other, and are each independently selected from a single bond, substituted or unsubstituted with a carbon number of 6-18 Arylene, substituted or unsubstituted heteroarylene with 12-18 carbon atoms;

   Optionally, the substituents in L ₁ , L ₂ , L ₃ and L ₄ are each independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, alkyl with 3-8 carbon atoms Trialkylsilyl group, fluoroalkyl group with 1-4 carbon atoms, aryl group with 6-12 carbon atoms or heteroaryl group with 5-12 carbon atoms.
6. The nitrogen-containing compound according to claim 1, wherein L ₁ , L ₂ , L ₃ and L ₄ are the same or different from each other, and are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted Substituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted dibenzothienylene, substituted or unsubstituted The dibenzofurylene group, substituted or unsubstituted carbazolyl group, or a subunit group formed by connecting two or three of the above subunits through a single bond;

   Optionally, the substituents in L ₁ , L ₂ , L ₃ and L ₄ are the same or different, and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, Trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl or pyridyl.
7. The nitrogen-containing compound according to claim 1, wherein, one of Y ₁ and Y ₂ is

   

   The other is selected from hydrogen, a substituted or unsubstituted aryl group with 6-25 carbon atoms, a substituted or unsubstituted heteroaryl group with 12-18 carbon atoms; and when Y ₁ is hydrogen, L ₃ not a single key;

   Optionally, the substituents in _Y1 and _Y2 are the same or different, and are each independently selected from deuterium, cyano, halogen, alkyl with 1-4 carbon atoms, haloalkane with 1-4 carbon atoms group, deuterated alkyl group with 1-4 carbon atoms, cycloalkyl group with 5-10 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 5-12 carbon atoms or carbon A trialkylsilyl group with 3-8 atoms.
8. The nitrogen-containing compound according to claim 1, wherein, one of Y ₁ and Y ₂ is

   

   The other is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl , substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl; and when Y ₁ is hydrogen, L ₃ is not a single bond;

   Optionally, the substituents in Y _{and Y} are the same or different, and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuteromethyl, cyclopentyl , cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl .
9. The nitrogen-containing compound according to claim 1, wherein Y ₁ or Y ₂ is

   

   and

   

   selected from the group consisting of:

   

   
10. The nitrogen-containing compound according to claim 1, wherein Y ₁ or Y ₂ is

    

    and

    

    selected from the group consisting of:

    
11. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:

    

    

    

    

    

    

    

    

    

    

    
12. An electronic component, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; it is characterized in that the functional layer comprises the nitrogen-containing compound.
13. The electronic component according to claim 12, wherein the functional layer comprises a hole transport layer comprising the nitrogen-containing compound;

    Optionally, the electronic component is an organic electroluminescent device, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is opposite to the second hole transport layer. The hole transport layer is closer to the anode, wherein the second hole transport layer comprises the nitrogen-containing compound.
14. An electronic device comprising the electronic component according to claim 12 or 13.

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