WO2021170008A1

WO2021170008A1 - Nitrogen-containing compound, electronic component, and electronic device

Info

Publication number: WO2021170008A1
Application number: PCT/CN2021/077730
Authority: WO
Inventors: 马天天; 肖蛟; 马占耿; 李昕轩; 喻超
Original assignee: 陕西莱特光电材料股份有限公司
Priority date: 2020-02-28
Filing date: 2021-02-24
Publication date: 2021-09-02

Abstract

The present application relates to the technical field of organic materials, and provides a nitrogen-containing compound, an electronic component, and an electronic device. The nitrogen-containing compound has a structure shown in formula (I). The nitrogen-containing compound can improve the performance of the electronic component.

Description

Nitrogen-containing compounds, electronic components and electronic devices

Cross-references to related applications

This application requires a Chinese patent application filed on February 28, 2020 with an application number of CN202010130395.2, a Chinese patent application filed on August 5, 2020 with an application number of CN202010777056.3, and a Chinese patent application filed on February 28, 2020. The priority of the Chinese patent application with the application number CN202010131346.0 and the Chinese patent application with the application number CN202011308317.3 filed on November 20, 2020, the content of the above-mentioned Chinese patent application is cited here as a part of this application.

Technical field

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

Background technique

With the development of electronic technology and the advancement of material science, the application range of electronic components used to realize electroluminescence or photoelectric conversion has become more and more extensive. Such electronic components usually include a cathode and an anode arranged oppositely, 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 between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.

For example, when the electronic element is an organic electroluminescence device, it generally includes an anode, a hole transport layer, an electroluminescence layer as an energy conversion layer, an electron transport layer, and a cathode that are stacked in sequence. When 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, the holes on the anode side also move to the light emitting layer, and the electrons and holes are combined in the electroluminescent layer. Excitons are formed, and the excitons are in an excited state to release energy to the outside, so that the electroluminescent layer emits light to the outside.

In electronic components that realize electroluminescence or photoelectric conversion, the hole transport performance of the film layer between the anode and the energy conversion layer has an important influence on the performance of the electronic components. For example, CN110467536A, KR1020130086757A, CN110183333A, etc. disclose materials that can prepare hole transport layers in organic electroluminescent devices. However, it is still necessary to continue to develop new materials to further improve the performance of electronic components.

The above-mentioned information described in the background section is only used to enhance the understanding of the background of the application, and therefore it may include information that does not constitute the prior art known to those of ordinary skill in the art.

Summary of the invention

The purpose of this application is to provide a nitrogen-containing compound, an electronic component and an electronic device to improve the performance of the electronic component and the electronic device. In order to achieve the above-mentioned purpose of the invention, this application adopts the following technical solutions:

The first aspect of the present application provides a nitrogen-containing compound, the structure of the nitrogen-containing compound is shown in formula I:

Wherein, L is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 6-30 carbon atoms; the substituents in L are each independently selected from: deuterium , Halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, and those with 1-10 carbon atoms Haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkyl with 3-12 carbon atoms Silicon-based

Ar ₁ , Ar ₂ , and Ar ₃ are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms The substituents in Ar ₁ , Ar ₂ , and Ar ₃ are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and the number of carbon atoms is 3-18 heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and those with 1-10 carbon atoms Alkoxy group, alkylthio group having 1-10 carbon atoms, trialkylsilyl group having 3-12 carbon atoms;

In Ar ₁ , Ar ₂ , Ar ₃ and L, when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form a 5- to 13-membered saturation with the atoms to which they are connected together. Or unsaturated ring;

R ₁ and R ₂ are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkoxy groups with 1-10 carbon atoms, and 1 carbon atoms -10 alkylthio group, trialkylsilyl group with 3-12 carbon atoms;

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

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.

The second aspect of the present application provides an electronic component, which includes an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; wherein, the functional layer includes the first The nitrogen-containing compound described in the aspect. According to one embodiment, the electronic component is an organic electroluminescent device. According to another embodiment, the electronic component is a photoelectric conversion device.

A third aspect of the present application provides an electronic device, which includes the electronic component described in the second aspect of the present application.

Description of the drawings

The above-mentioned and other features and advantages of the present application will become more apparent by describing in detail the exemplary 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 diagram of the structure of a photoelectric conversion device according to an embodiment of the present application.

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

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

Description of Reference Signs

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, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device.

Detailed ways

The specific implementation of the present application will be described in detail below with reference to the accompanying drawings. It should be understood that the specific implementations described here are only used to illustrate and explain the application, and are not used to limit the application.

In the first aspect, this application provides a nitrogen-containing compound, the structure of which is shown in formula I:

In this application, the term "optionally" means that the event or environment described later can but need not occur, and the description includes occasions where the event or environment occurs or does not occur. For example, "optionally, two substituents ×× form a ring" means that these two substituents can form a ring but do not necessarily form a ring, including: the situation where two substituents form a ring and two substituents do not form a ring Scene.

In this application, the descriptions "each... are independently" and "... are independently" and "... are independently selected from" are interchangeable, and should be understood in a broad sense, which can mean either In different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that the specific options expressed between the same symbols do not affect each other in the same group. E.g,"

Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine", and its meaning is: formula Q-1 represents 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 R on two benzene rings The number q of "substituents can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

In this application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In other words, the aryl group can be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups conjugated by a carbon-carbon bond, through A monocyclic aryl group and a fused ring aryl group conjugated by carbon-carbon bonds, and two or more fused ring aryl groups conjugated by a carbon-carbon bond. That is, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as aryl groups in the present application. Among them, the aryl group does not contain heteroatoms such as B, N, O, S, P, and Si. For example, in this application, biphenyl, terphenyl, etc. are aryl groups. 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 and so on.

In this application, the substituted aryl group can be one or more hydrogen atoms in the aryl group, such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, ring Alkyl, alkoxy, alkylthio and other groups are substituted. Specific examples of heteroaryl substituted aryl include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothienyl substituted phenyl, pyridyl substituted phenyl, carbazolyl substituted phenyl, etc. . It should be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to an aryl group and a substituted group. The total number of carbon atoms of the group is 18.

In this application, a heteroaryl group refers to a monovalent aromatic ring containing at least one heteroatom in the ring or a derivative thereof. The heteroatom may be at least one of B, O, N, P, Si, and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, the heteroaryl group can be a single aromatic ring system or multiple aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic The ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazine Azinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophene Thienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silylfluorenyl, dibenzofuranyl and N-phenylcarbazole Group, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., but not limited thereto. Among them, thienyl, furanyl, phenanthrolinyl, etc. are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are polycyclic rings conjugated through carbon-carbon bonds. System type of heteroaryl.

In this application, the substituted heteroaryl group may be one or more hydrogen atoms in the heteroaryl group, such as deuterium atom, halogen group, -CN, aryl group, heteroaryl group, trialkylsilyl group, alkyl group. , Cycloalkyl, alkoxy, alkylthio and other groups are substituted. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

In this application, the non-positioned connecting bond refers to the 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 penetrates, 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 non-positional linkages that penetrate the bicyclic ring, and the meaning represented by the formula (f) -1) Any possible connection mode shown in formula (f-10).

For another example, as shown in the following formula (X'), the phenanthryl group represented by the formula (X') is connected to other positions of the molecule through a non-localized bond extending from the middle of the benzene ring on one side, which represents The meaning of includes any possible connection modes shown in formula (X'-1) to formula (X'-4).

The non-positional substituent in this application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R'represented by the formula (Y) is connected to the quinoline ring through a non-localized linkage, and the meaning represented by it includes formulas (Y-1) to Any possible connection mode shown in formula (Y-7).

In this application, a cycloalkyl group with 3-10 carbon atoms can be used as a substituent of an aryl group and a heteroaryl group, and specific examples thereof include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl and the like.

In this 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. The number of carbon atoms may be 1, for example. 2, 3, 4, 5, 6, 7, 8, 9, 10, specific examples of alkyl groups having 1-10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-propyl Butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc.

In this application, halogen may include fluorine, chlorine, bromine, and iodine.

In the present application, the number of carbon atoms of the alkoxy group having 1-10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkoxy group include but It is not limited to methoxy, ethoxy, n-propoxy and the like.

In this application, the haloalkyl group can be, for example, a fluoroalkyl group, and the number of carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples include, but are not limited to, trifluoromethyl base.

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

In the present application, the number of carbon atoms of the aryl group as a substituent is 6-20 or 6-18, and the number of carbon atoms may be 6, 10, 12, 14, 18, 20, etc., for example. Specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, phenanthryl, and the like.

In the present application, the number of carbon atoms of the heteroaryl group as a substituent is 3-20 or 3-18, and the number of carbon atoms may be 3, 4, 5, 7, 8, 9, 12, 18, etc., for example. Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.

In this application, Ar ₁ , Ar ₂ and Ar ₃ can each independently be selected from the group consisting of the groups represented by the following chemical formula i-1 to chemical formula i-14:

Among them, M _{1 is} selected from a single bond or

G ₁ to G ₅ are each independently selected from N or C(F ₁ ), and _{at least one of G 1} to G ₅ is selected from N; when _{two or more of G 1} to G ₅ are selected from C(F ₁ ) , Any two F _{1 are the} same or different;

G ₆ to G ₁₃ are each independently selected from N or C(F ₂ ), and _{at least one of G 6} to G ₁₃ is selected from N; when _{two or more of G 6} to G ₁₃ are selected from C(F ₂ ) , Any two F _{2 are the} same or different;

G ₁₄ to G ₂₃ are each independently selected from N or C(F ₃ ), and _{at least one of G 14} to G ₂₃ is selected from N; when _{two or more of G 14} to G ₂₃ are selected from C(F ₃ ) , Any two F _{3 are the} same or different;

H _{1 is} selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, alkyl groups having 1 to 10 carbon atoms, and those having 1 to 10 carbon atoms A halogenated alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;

H ₂ to H ₉ and H ₂₁ are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, and alkane having 1 to 10 carbon atoms Group, halogenated alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, carbon Heteroaryl groups with 3 to 18 atoms;

H ₁₀ to H ₂₀ and F ₁ to F ₃ are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl groups having 3 to 12 carbon atoms, and 1 to carbon atoms 10 alkyl groups, halogenated alkyl groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkyl sulfides having 1 to 10 carbon atoms Group, aryl group having 6 to 18 carbon atoms, heteroaryl group having 3 to 18 carbon atoms;

h ₁ ～h ₂₁ are represented by h _k , H ₁ ～H ₂₁ are represented by H _k , k is a variable, representing any integer from 1 to 21, and h _k is the number of substituents H _k ; wherein, when k is selected from 5 Or when 17, h _{k is} selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, h _{k is} selected from 1, 2, 3 or 4; when k is selected When 1, 3, 4, 6, 9 or 14, h _{k is} selected from 1, 2, 3, 4 or 5; when k is 13, h _{k is} selected from 1, 2, 3, 4, 5 or 6; When k is selected from 10 or 19, h _{k is} selected from 1, 2, 3, 4, 5, 6 or 7; when k is 20, h _{k is} selected from 1, 2, 3, 4, 5, 6, 7 Or 8; when k is 11, h _{k is} selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when h _{k is} greater than 1, any two H _{k are the} same or different;

K _{1 is} selected from O, S, Se, N (H ₂₂ ), C (H ₂₃ H ₂₄ ), Si (H ₂₃ H ₂₄ ); wherein, H ₂₂ , H ₂₃ , and H ₂₄ are each independently selected from: carbon atoms An aryl group having 6 to 18, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above H ₂₃ and H ₂₄ are connected to each other to form a 5- to 13-membered saturated or unsaturated ring with the atoms they are commonly connected to;

K _{2 is} selected from a single bond, O, S, Se, N (H ₂₅ ), C (H ₂₆ H ₂₇ ), Si (H ₂₆ H ₂₇ ); wherein, H ₂₅ , H ₂₆ , and H ₂₇ are each independently selected from : C6-C18 aryl group, C3-C18 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, or the above H ₂₆ and H ₂₇ are connected to each other to form a 5- to 13-membered saturated or unsaturated ring with the atoms to which they are commonly connected.

In chemical formulas i-10 and i-11, when K ₂ represents a single bond, the specific structures of chemical formulas i-10 and i-11 are as follows:

In the above _{two groups of H 23} and H ₂₄ , and the above H ₂₆ and H ₂₇ , the ring formed by connecting the two groups in each group may be a 5-13 membered saturated or unsaturated ring. Optionally, _{in the two groups of H 23} and H ₂₄ , H ₂₆ and H ₂₇ , the ring formed by connecting the two groups in each group may be a 5-13 membered saturated aliphatic ring or an aromatic ring. According to one embodiment, the _{two groups of H 23} and H ₂₄ , H ₂₆ and H ₂₇ can respectively form a saturated aliphatic monocyclic ring of 5-8 members or an aromatic ring of 10-13 members. For example, in chemical formula i-10, when K ₂ and M ₁ are both single bonds, H ₁₉ is hydrogen, h ₁₉ =7, K ₁ is C (H ₂₃ H ₂₄ ), and H ₂₃ and H ₂₄ are connected to each other to When they form a 5-membered saturated aliphatic monocyclic ring together with the atoms (C) they are connected to together, the chemical formula i-10 is

Similarly, the chemical formula i-10 can also be

That is, H ₂₃ and H ₂₄ are connected to each other to form a 13-membered aromatic ring with the atoms to which they are commonly connected.

In chemical formula i-13 and chemical formula i-14, F ₂ to F ₃ can be _{represented by F x} , where x is a variable and represents 2 or 3. For example, when x is 2, F _x refers to F ₂ . It should be appreciated that, when not connected to the positioning linkage C (F _x) a, C (F _x) in the absence of F _x. For example, in chemical formula i-13, when

When connected to G ₁₂ , G ₁₂ can only represent C atom, that is, the structure of chemical formula i-13 is:

According to the first embodiment, the structure of the nitrogen-containing compound is shown in Chemical Formula 1:

In Chemical Formula 1, L is selected from the group shown in Chemical Formula 1-1;

R ₁ and R ₂ are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, number of carbon atoms Cycloalkyl groups of 3-10, aryl groups of 6-20 carbon atoms, heteroaryl groups of 3-20 carbon atoms, alkoxy groups of 1-10 carbon atoms, 1- 10 alkylthio groups, trialkylsilyl groups with 3-12 carbon atoms;

R _{3 is} selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;

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 or 4, when n _{3 is} greater than 1, any two R _{3 are the} same or different;

Ar ₁ , Ar ₂ , and Ar ₃ are the same or different from each other, each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ；

The substituents in Ar ₁ , Ar ₂ , and Ar ₃ are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3-18 carbon atom Heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and alkoxy groups with 1-10 carbon atoms , Alkylthio groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms; in Ar ₁ , Ar ₂ , and Ar ₃ , when there are two substituents on the same atom, Optionally, two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms to which they are commonly connected.

In the first embodiment, the nitrogen-containing compound having the structure shown in Chemical Formula 1 includes two aromatic amine groups connected to each other through a benzene ring, and one of the aromatic amine groups includes an adamantane spiro-bound fluorenyl group , This structure design makes the electron cloud density distribution more reasonable, so that the compound has a high hole mobility. In addition, one of the four aromatic substituents in the diaromatic amine structure is a fluorenyl group spiro-coated with adamantane, which improves the asymmetry of the overall molecular structure. The asymmetric structure brings low crystallinity and good film-forming ability. . When the nitrogen-containing compound is applied to the hole transport layer of the light-emitting layer of an organic electroluminescence device, the efficiency and lifetime of the device can be improved.

In the first embodiment, the structure of the nitrogen-containing compound can be selected from the group consisting of chemical formula 1-A to chemical formula 1-D:

in,

The specific structure can be as follows:

Optionally,

for

In Chemical Formula 1, when Ar ₁ , Ar ₂ and Ar ₃ have substituents, the number of substituents may be one or two or more (ie one or more); when the number of substituents is two or more, the substitution The base can be the same or different. In an exemplary embodiment, in Ar ₁ , Ar ₂ , and Ar ₃ , there are two substituents on the same atom, and the two substituents are connected to each other to form a 5-13 member with the atom to which they are connected together. The saturated aliphatic ring or aromatic ring (including aromatic ring, heteroaromatic ring).

In Chemical Formula 1, optionally, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, substituted or unsubstituted carbon atoms having 4 to 25 Heteroaryl. For example, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25 substituted or unsubstituted aryl groups, or selected from 4, 5, 8, 9, 11, 12, 16, 18, 20, 21, 22, 23, 24, 25 substituted or unsubstituted heteroaryl.

In Chemical Formula 1, optionally, _{the substituents in Ar 1} , Ar ₂ , and Ar ₃ are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and 1 to 4 haloalkyl, carbon 5-10 cycloalkyl, carbon 6-15 aryl, carbon 5-12 heteroaryl, carbon 1-4 alkoxy Group, alkylthio group having 1 to 4 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms. Specific examples of the substituents in Ar ₁ , Ar ₂ , and Ar ₃ include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, Cyclohexyl, phenyl, naphthyl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, methoxy, ethoxy, methylthio, ethylthio, trimethyl Silicon-based, trifluoromethyl, etc.

In Chemical Formula 1, optionally, Ar ₁ is a substituted or unsubstituted group Z ₁ , Ar ₂ is a substituted or unsubstituted group Z ₂ , and Ar ₃ is a substituted or unsubstituted group Z ₃ , where The substituted groups Z ₁ , Z ₂ and Z ₃ are each independently selected from the group consisting of:

The substituted group Z ₁ , the substituted group Z ₂ and the substituted group Z ₃ each independently have one or two or more substituents, and the substituents are independently selected from: deuterium, cyano, fluorine, carbon number It is an alkyl group having 1-4, a haloalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, an alkoxy group having 1-4 carbon atoms, and 1-4 carbon atoms The alkylthio group, the trialkylsilyl group with 3-7 carbon atoms. When the number of substituents is two or more, any two substituents are the same or different. For example, specific examples of substituents include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, methylthio, ethoxy Group, trimethylsilyl, trifluoromethyl, etc.

In Chemical Formula 1, optionally, Ar ₁ , Ar ₂ and Ar ₃ may each independently be selected from the group consisting of the following groups:

In Chemical Formula 1, optionally, Ar ₂ and Ar ₃ are each independently selected from the group consisting of the following groups:

In Chemical Formula 1, optionally, Ar _{1 is} selected from the group consisting of the following groups:

In Chemical Formula 1, optionally, Ar _{1 is} selected from an aryl group having 6-15 carbon atoms or a heteroaryl group having 5-18 carbon atoms.

Further optionally, Ar _{1 is} selected from aryl groups having 6-14 carbon atoms or heteroaryl groups having 8-12 carbon atoms.

In Chemical Formula 1, optionally, R ₁ and R ₂ are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, carbon atom Cycloalkyl groups with 5-10 carbon atoms, aryl groups with 6-15 carbon atoms, heteroaryl groups with 3-15 carbon atoms, alkoxy groups with 1-4 carbon atoms, 1 carbon atoms -4 alkylthio group, trialkylsilyl group having 3-7 carbon atoms.

Further optionally, R ₁ and R ₂ are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, and 6-12 aryl, carbon 3-12 heteroaryl, carbon 1-4 alkoxy, carbon 1-4 alkylthio, carbon 3-7 The trialkylsilyl group. Specific examples of R ₁ and R ₂ respectively include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, naphthalene Group, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, methoxy, ethoxy, methylthio, ethylthio, trimethylsilyl.

In Chemical Formula 1, optionally, n _{1 is} selected from 0, 1 or 2, and n _{2 is} selected from 0 or 1. Further optionally, n ₁ +n ₂ ≤2.

In chemical formula 1, optionally, R _{3 is} selected from deuterium, fluorine, cyano, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkyl groups having 1 to 4 carbon atoms. An oxy group, an alkylthio group having 1 to 4 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms. Specific examples of R ₃ include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio , Trimethylsilyl, trifluoromethyl.

In Chemical Formula 1, optionally, n _{3 is} selected from 0, 1, or 2.

In the first embodiment, optionally, the nitrogen-containing compound may be selected from the group consisting of the following compounds:

According to the second embodiment, the structure of the nitrogen-containing compound is shown in Chemical Formula 2:

In chemical formula 2, L is selected from substituted or unsubstituted groups Q with 7-30 carbon atoms, and group Q is selected from: bicyclic fused arylene, tricyclic fused arylene, and bicyclic fused heteroarylene One of aryl and tricyclic fused heteroarylene, or selected from: monocyclic arylene, monocyclic heteroarylene, bicyclic fused arylene, tricyclic fused arylene, bicyclic fused Optionally at least two groups in the heteroarylene group and the tricyclic fused heteroarylene group are connected to each other by a single bond to form a divalent group;

The substituted group Q means that the group Q has one or more substituents, and the substituents are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms , Heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;

Ar ₁ , Ar ₂ and Ar _{3 are the} same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ；

The substituents in Ar ₁ , Ar ₂ and Ar ₃ are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3-18 carbon atom Heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and alkoxy groups with 1-10 carbon atoms , Alkylthio groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms;

In Ar ₁ , Ar ₂ , Ar ₃ and substituted groups Q, when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form 5- 13-membered saturated or unsaturated ring;

R ₁ and R _{2 are the} same or different, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, number of carbon atoms Cycloalkyl groups of 3-10, aryl groups of 6-20 carbon atoms, heteroaryl groups of 3-20 carbon atoms, alkoxy groups of 1-10 carbon atoms, 1- 10 alkylthio groups, trialkylsilyl groups with 3-12 carbon atoms;

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

n ₂ represents the number of substituents 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.

In the second embodiment, in the nitrogen-containing compound with the structure shown in Chemical Formula 2, an adamantane spiro-bound fluorenyl group is combined with a triarylamine, wherein the adamantane spiro-bound fluorenyl group has electron-rich properties and strong rigidity , This group has a high hole mobility; when it is combined with triarylamine, a material suitable for the hole transport layer of organic electroluminescent devices can be obtained; and the nitrogen-containing compounds of the present application also exist and The central triaromatic amine is another triaromatic amine group bound by a group such as biphenyl or terphenyl (ie, L in Chemical Formula 1), where L has an appropriate conjugation range (for hole transport materials) ), while further improving the hole mobility, reducing the symmetry of the molecule, increasing the degree of freedom of the molecular structure, so that the material can exist more stably in the amorphous state; for example, the nitrogen-containing compound is applied to organic electricity In the case of electroluminescent devices, a more uniform and Joule-resistant film can be formed, which improves the luminous efficiency of the device and prolongs the life of the device.

Specifically, the structure of the nitrogen-containing compound shown in Chemical Formula 2 is selected from the group consisting of Chemical Formula 2-1 to Chemical Formula 2-4:

In Chemical Formula 2, optionally, R ₁ and R _{2 are the} same or different, and are independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and 1 to 4 carbon atoms Halogenated alkyl groups, cycloalkyl groups having 5-10 carbon atoms, aryl groups having 6-15 carbon atoms, heteroaryl groups having 5-10 carbon atoms, alkoxy groups having 1-4 carbon atoms, The alkylthio group having 1 to 4 carbon atoms, and the trialkylsilyl group having 3 to 7 carbon atoms. Optionally, n _{1 is} selected from 0, 1 or 2, and n _{2 is} selected from 0 or 1.

In the group Q of the present application, the expression "optionally at least two groups selected from: monocyclic arylene..." can be understood to include at least two of the same group, and may also include different groups. At least two in the group. For example, when the group Q is a group formed by two or three of the same group through a single bond, and the same group is a phenylene group, Q can be a biphenylene group or a terphenylene group; For example, when the group Q is a group formed by two different groups through a single bond, and the two groups are phenylene and dibenzofuranyl, Q is

In Chemical Formula 2, when the structure of L includes a fused aromatic ring or a fused heteroaromatic ring, the number of benzene rings connected to each other in a fused manner does not exceed 3. Such L has a more suitable conjugation range, such as conjugated with Compared with more benzene rings fused to each other in a larger range (for example, four benzene rings fused to each other), the L of the present application can avoid the energy band from being too narrow, making the nitrogen-containing compound suitable as a hole transport material and improving Device performance.

In Chemical Formula 2, the number of carbon atoms of L is, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26 , 27, 28, 29, 30.

Optionally, L is selected from substituted or unsubstituted groups Q with 8-25 carbon atoms. Also optionally, L is selected from substituted or unsubstituted groups Q with 10-25 carbon atoms.

Optionally, the substituents in the substituted group Q are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, carbon An alkoxy group having 1 to 4 atoms, an alkylthio group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, and a phenyl group.

Optionally, the number of substituents in the substituted group Q is not more than 2.

In an exemplary embodiment, L is the following group substituted: a bicyclic fused arylene group, a tricyclic fused arylene group, a bicyclic fused heteroarylene group, or a tricyclic fused heteroarylene group, And the substituent is phenyl.

In another exemplary embodiment, the group Q is composed of a phenylene group and a bicyclic fused arylene group, a tricyclic fused arylene group, a bicyclic fused heteroarylene group, and a tricyclic fused heteroarylene group. A divalent group formed by one of the groups.

In an exemplary embodiment, in Ar ₁ , Ar ₂ , Ar ₃ and the substituted group Q, there are two substituents on the same atom, and the two substituents are connected to each other to connect with them. Together they form a 5-13 membered saturated aliphatic ring or aromatic ring (including aromatic ring and heteroaromatic ring).

In chemical formula 2, optionally, L is selected from the group consisting of the groups shown in chemical formula j-1 to chemical formula j-9:

Among them, M _{2 is} selected from a single bond or

Q ₁ to Q ₅ are each independently selected from N or C(F ₄ ), and _{at least one of Q 1} to Q ₅ is selected from N; when _{two or more of Q 1} to Q ₅ are selected from C(F ₄ ) , Any two F _{4 are the} same or different;

Q ₆ to Q ₁₃ are each independently selected from N or C(F ₅ ), and _{at least one of Q 6} to Q ₁₃ is selected from N; when _{two or more of Q 6} to Q ₁₃ are selected from C(F ₅ ) , Any two F _{5s are the} same or different;

Q ₁₄ to Q ₂₃ are each independently selected from N or C(F ₆ ), and _{at least one of Q 14} to Q ₂₃ is selected from N; when _{two or more of Q 14} to Q ₂₃ are selected from C(F ₆ ) , Any two F _{6 are the} same or different;

E ₁ to E ₁₀ and F ₄ to F ₆ are each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, heteroaryl with 3 to 10 carbon atoms, and 6 to 12 carbon atoms Aryl group, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms , C1-C10 alkoxy group, C1-C10 alkylthio group;

E ₁ ～E ₁₀ are represented by E _r , e ₁ ～e ₁₀ are represented by e _r , where r represents a variable and is selected from any integer from 1 to 10; when r is selected from 1, 2, 3, 4, 5 or 10 When _{r is} selected from 1, 2, 3 or 4; when r is selected from 6 or 8, e _{r is} selected from 1, 2, 3, 4, 5 or 6; when r is 9, e _{r is} selected from 1 , 2, 3, 4, 5, 6 or 7; when er is 7, e _{r is} selected from 1, 2, 3, 4, 5, 6, 7 or 8; and when e _{r is} greater than 1, any two E _{r is the} same or not the same;

K _{3 is} selected from O, S, Se, N (E ₁₁ ), C (E ₁₂ E ₁₃ ), Si (E ₁₂ E ₁₃ ); wherein, E ₁₁ , E ₁₂ , and E ₁₃ are each independently selected from: carbon atoms An aryl group having 6 to 12, a heteroaryl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, or the above E ₁₂ and E ₁₃ are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms they are connected to together;

K _{4 is} selected from single bond, O, S, Se, N (E ₁₄ ), C (E ₁₅ E ₁₆ ), Si (E ₁₅ E ₁₆ ); wherein, E ₁₄ , E ₁₅ , and E ₁₆ are each independently selected from : C6-C12 aryl group, C3-C10 heteroaryl group, C1-C10 alkyl group, C3-C10 cycloalkyl group, or the above E ₁₅ and E ₁₆ are connected to each other to form a 5-13 membered saturated or unsaturated ring with the atoms to which they are commonly connected.

In chemical formulas j-5 and j-6, when K ₄ represents a single bond, the specific structures of chemical formulas j-5 and j-6 are as follows:

In the above _{two groups of E 12} and E ₁₃ , and the above E ₁₅ and E ₁₆ , the ring formed by connecting the two groups in each group may be a 5-13 membered saturated or unsaturated ring. Optionally, _{in the two groups of E 12} and E ₁₃ , E ₁₅ and E ₁₆ , the ring formed by connecting the two groups in each group is a 5-13 membered saturated aliphatic ring or aromatic ring. For example, the _{two groups of E 12} and E ₁₃ , and the above-mentioned E ₁₅ and E ₁₆ can respectively form a saturated aliphatic monocyclic ring of 5-8 members or an aromatic ring of 10-13 members. For example, in the chemical formula j-5, when K ₄ and M ₂ are both single bonds, E ₈ is hydrogen, e ₈ =6, K ₃ is C (E ₁₂ E ₁₃ ), and E ₁₂ and E ₁₃ are connected to each other to When the atoms connected with them form a 5-membered saturated aliphatic monocyclic ring, the chemical formula j-5 is

Similarly, the chemical formula j-5 can also be

In the chemical formula j-7 and the chemical formula j-9, F ₄ to F ₆ can be _{represented by F x} , where x is a variable and represents 4, 5, or 6. For example, when x is 4, F _x refers to F ₄ . It should be appreciated that, when not connected to the positioning linkage C (F _x) a, C (F _x) in the absence of F _x. For example, in the chemical formula j-8, when

When connected to Q ₈ , Q ₈ can only represent C atom, that is, the structure of chemical formula j-8 is:

In Chemical Formula 2, optionally, L is selected from a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the group consisting of the following groups:

The substituted group Q has one or more than two substituents, and the substituents are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, 5- 10 cycloalkyl, carbon 1-4 alkoxy, carbon 1-4 fluoroalkyl, carbon 1-4 alkylthio, carbon 3-7 The trialkylsilyl, phenyl, naphthyl.

In Chemical Formula 2, optionally, L is selected from the group consisting of the following groups:

Optionally, L is selected from the group consisting of the following groups:

Optionally, the structure of L is

In Chemical Formula 2, optionally, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, and substituted or unsubstituted carbon atoms having 5-25 Heteroaryl. For example, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from carbon atoms of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25 substituted or unsubstituted aryl, or selected from carbon atoms of 5, 8, 9, 11, 12, 16, 18, 20, 21, 22, 23, 24, 25 Substituted or unsubstituted heteroaryl.

In Chemical Formula 2, optionally, _{the substituents in Ar 1} , Ar ₂ and Ar ₃ are each independently selected from: deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, 1 to 1 4 haloalkyl, carbon 5-10 cycloalkyl, carbon 1-4 alkoxy, carbon 1-4 alkylthio, carbon 3-7 three Alkylsilyl. Specific examples of the substituents in Ar ₁ , Ar ₂ , and Ar ₃ include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, Cyclohexyl, phenyl, naphthyl, pyridyl, methoxy, ethoxy, methylthio, ethylthio, trimethylsilyl, trifluoromethyl, etc.

In Chemical Formula 2, optionally, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from substituted or unsubstituted group Z, wherein the unsubstituted group Z is selected from the group consisting of the following groups:

The substituted group Z has one or more substituents, and the substituents are each independently selected from: deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, alkyl halide with 1-4 carbon atoms Group, carbon atoms of 5-10 cycloalkyl, carbon atoms of 1-4 alkoxy, carbon atoms of 1-4 alkylthio, carbon atoms of 3-7 trialkylsilyl; when substituted When the number of groups is greater than 1, the substituents are the same or different. For example, specific examples of substituents include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, methoxy, methylsulfide Group, ethoxy group, trimethylsilyl, ethyldimethylsilyl, trifluoromethyl, etc.

In Chemical Formula 2, optionally, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from the group consisting of the following groups:

Further optionally, Ar ₁ , Ar ₂ and Ar ₃ are each independently selected from the group consisting of the following groups:

In the second embodiment, optionally, the nitrogen-containing compound is selected from the group consisting of the following compounds:

The application does not specifically limit the synthesis method of the nitrogen-containing compound provided, and those skilled in the art can determine a suitable synthesis method according to the preparation method of the nitrogen-containing compound provided in the application in combination with the synthesis example. In other words, the synthesis example part of the present application exemplarily provides a method for preparing nitrogen-containing compounds, and the raw materials used can be obtained by commercially available or well-known methods in the art. Those skilled in the art can obtain all the nitrogen-containing compounds provided in this application according to the preparation methods of these exemplary synthesis examples. All specific preparation methods for preparing the nitrogen-containing compounds will not be described in detail here. Limitations of the invention.

In a second aspect, the present application provides an electronic component. The electronic component includes an anode and a cathode disposed oppositely, and a functional layer provided between the anode and the cathode; the functional layer includes the nitrogen-containing Compound.

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

According to one embodiment, the electronic component may be an organic electroluminescent device. As shown in FIG. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, and a second hole transport layer 322 (also referred to as an "electron blocking layer"), which are sequentially stacked and arranged as an energy conversion layer. The organic light emitting layer 330, the electron transport layer 340, and the cathode 200 are formed. Among them, the first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320. According to a specific embodiment, the nitrogen-containing compound provided in the present application can be applied to the first hole transport layer 321. According to another specific embodiment, the nitrogen-containing compound provided in the present application can be applied to the second hole transport layer 322.

Optionally, the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided in the present application and other materials. For example, the nitrogen-containing compound shown in Chemical Formula 1 is applied to the first hole transport layer 321, and the material of the second hole transport layer 322 can be selected from carbazole polymers or other types of compounds, which is not particularly limited in this application. For example, it can be composed of the compound TCTA. For another example, the nitrogen-containing compound shown in Chemical Formula 2 is applied to the second hole transport layer 322 of the organic electroluminescence device, and the material of the first hole transport layer 321 may be NPB, for example.

Optionally, the anode 100 includes the following anode material, which is preferably a material with a large work function (work function) that facilitates injection of holes 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 conductive 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 containing indium tin oxide (ITO) as an anode.

In this application, 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 host material, the host material transfers energy to the guest material, so that the guest material can emit light.

The host material of the organic light-emitting layer 330 may be, for example, a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, etc., which are not particularly limited in this application. For example, the host material of the organic light emitting layer 330 may be α, β-ADN, CBP, or PVK. The guest material of the organic light-emitting layer 330 may be, for example, 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, and this application does not make any special considerations to this. limits. For example, the guest material of the organic light emitting layer 330 may be TBPe or Ir(piq) ₂ (acac).

Optionally, the electron transport layer 340 may have a single-layer structure or a multilayer structure, which may include one or more electron-transporting materials. The electron-transporting materials may be selected from, but not limited to, benzimidazole derivatives, oxacin Diazole derivatives, quinoxaline derivatives or other electron transport materials. For example, the electron transport layer 340 may be composed of TPBi and LiQ, or composed of TPO and LiQ.

Optionally, as shown in FIG. 1, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the hole transport layer. 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. For example, the hole injection layer 310 may be composed of HAT-CN.

Optionally, as shown in FIG. 1, an electron injection layer 350 may be further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides, alkali metal halides, and Yb, or may include complexes of alkali metals and organic substances. For example, the electron injection layer 350 may include LiQ or Yb.

Optionally, the cathode 200 includes the following 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: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF/Al, Liq/ Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca, but not limited thereto. It is preferable to include a metal electrode containing silver and magnesium as a cathode.

Optionally, as shown in FIG. 1, the hole injection layer 310, the first hole transport layer 321, the second hole transport layer 322, the organic light emitting layer 330, the electron transport layer 340, and the electron injection layer 350 constitute the functional layer 300 .

Optionally, the organic electroluminescent device is a blue light device or a red light device.

According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in FIG. 2, 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 the present application.

Optionally, as shown in FIG. 2, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the nitrogen-containing compound of the present application. Wherein, the hole transport layer 320 may be composed of the nitrogen-containing compound provided in the present application, or may be composed of the nitrogen-containing compound provided in the present application and other materials.

Optionally, the hole transport layer 320 may further include inorganic doping materials to improve the hole transport performance of the hole transport layer 320.

Optionally, as shown in FIG. 2, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200 that are sequentially stacked.

Optionally, the photoelectric conversion device may be a solar cell, especially an organic thin film solar cell. In a specific embodiment, the solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer contains the nitrogen-containing compound of the present application.

In a third aspect, the present application provides an electronic device, which includes the above-mentioned electronic component.

According to one embodiment, as shown in FIG. 3, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, light modules, etc.

According to another embodiment, as shown in FIG. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the aforementioned photoelectric conversion device. The second electronic device 500 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.

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

1. Synthesis of raw materials A to D

1. Synthesis of raw material A:

Under the protection of nitrogen, add 2-bromo-4-fluoro-1-iodobenzene (30g, 0.1mol) and p-chlorophenylboronic acid (17.2g, 0.11mol) into a 500mL three-necked flask, then add 180mL of toluene and 120mL of ethanol , Water 120mL, Pd(pph ₃ ) ₄ (1.15g, 0.001mol), TBAB (3.22g, 0.1mol), potassium carbonate (27.642g, 0.2mol), heated to reflux, reacted for 4h, the reaction is complete, and then cooled to At room temperature, the reaction solution was washed with water and dried with magnesium sulfate. After filtration, the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using toluene to obtain a white solid material A (19.41 g, yield 68%).

2. Synthesis of raw material B:

Under the protection of nitrogen, add 4-bromo-3-iodoanisole (31.29g, 0.1mol) and p-chlorophenylboronic acid (17.2g, 0.11mol) into a 500mL three-necked flask, then add 180mL of toluene and 120mL of ethanol. Water 120mL, Pd(pph ₃ ) ₄ (1.15g, 0.001mol), TBAB (3.22g, 0.1mol), potassium carbonate (27.642g, 0.2mol), heated to reflux, reacted for 4h, the reaction is complete, and then cooled to room temperature The reaction solution was washed with water and then dried by adding magnesium sulfate. After filtration, the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified with toluene to obtain a white solid material B (20.83 g, yield 70%).

3. Synthesis of raw materials C and D

The raw materials C and D were synthesized by referring to the method of raw material A, except that 2-bromo-4-fluoro-1-iodobenzene was replaced with each raw material I, so that raw materials C and D were obtained accordingly. The specific structure of raw material I, the structure of raw materials C and D, and the yield are shown in Table 1.

Table 1

2. Synthesis of Intermediate 1-A-X

Take Intermediate 1-A-1 as an example to illustrate the synthesis of Intermediate 1-A-X.

1. Synthesis of Intermediate 1-A-1

(1) Under the protection of nitrogen, weigh out 2-bromo-4-chlorobiphenyl (142g, 530mmol) and THF (852mL) in a 2L three-necked round bottom flask and dissolve it at -80℃ to -90℃ until it becomes clear Measure n-BuLi (254.75mL, concentration of 2.5mol/L) into the reaction system slowly and dropwise. After reacting at -80°C to -90°C for 50 minutes, weigh the adamantanone (63.78g, 42.45). mmol), after dissolving adamantanone with THF (260mL), add it dropwise to the reaction system slowly, and react at a constant temperature at -80°C to -90°C for 1 hour. After the reaction is over, naturally warm to room temperature and react Pour 5wt% hydrochloric acid to pH<7, stir thoroughly, add dichloromethane (DCM) for extraction, combine the organic phases, wash with water until neutral, dry with anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure. The obtained oily substance was added to a flask with n-heptane, heated to reflux to a clear solution, and recrystallized at -20°C to obtain a white intermediate 1A (122 g, yield 68%).

(2) Under the protection of nitrogen, weigh out Intermediate 1A (122g, 360mmol), weigh out glacial acetic acid (1.5L), and stir at 55°C. After the raw materials are completely dissolved, add concentrated sulfuric acid (3.08mL, Concentration is 98%), continue to heat up to 60°C, stir for 30 minutes, wait for the reaction solution to cool down to room temperature naturally, pour 2L of deionized water, stir well and filter, rinse the filter cake with deionized water until it is neutral, and put it Bake the material in a vacuum drying oven at 60℃ for 1h, dissolve it with DCM, add anhydrous sodium sulfate and dry for 30min, filter and remove the solvent under reduced pressure, add n-heptane, recrystallize the crude product at -20℃, filter After drying the material in a vacuum drying oven, intermediate 1A-1 (104.8 g, yield 91%) was obtained.

2. Synthesis of other intermediates 1-A-X

Refer to the synthesis method of intermediate 1-A-1 to synthesize each intermediate 1-A-X in Table 2 respectively. The difference is that each raw material II is used instead of 2-bromo-4'-chlorobiphenyl. Among them, the main raw materials used, the corresponding intermediate structure, and the total yield of the intermediate synthesis are shown in Table 2.

Table 2

3. Synthesis of Intermediate 1-B-X

Take Intermediate 1-B-1 as an example to illustrate the synthesis of Intermediate 1-B-X.

1. Synthesis of Intermediate 1-B-1

Under the protection of nitrogen, the intermediate 1A-1 (104.8g, 326.6mmol), 4-aminobiphenyl (58g, 342.9mmol), tris(dibenzylideneacetone) two palladium (2.99g, 3.26mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (2.68g, 6.53mmol) and sodium tert-butoxide (47.08g, 489.9mmol) were added to toluene (800mL), heated to reflux (105- 108°C), stirred for 0.5h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered, and the filtrate was reduced under reduced pressure to remove the solvent; the crude product was recrystallized and purified with toluene to obtain a white solid intermediate lB-1 ( 100.75g, yield 68%).

2. Synthesis of other intermediates 1-B-X

Refer to the synthesis method of intermediate 1-B-1 to synthesize each intermediate 1-B-X in Table 3, the difference is that each intermediate 1-A-X is adjusted, and each raw material III is used instead of 2-aminobiphenyl. Among them, the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 3.

table 3

Fourth, the synthesis of intermediate 1-C-X

Take the intermediate 1-C-1 as an example to illustrate the synthesis of the intermediate 1-C-X.

1. Synthesis of Intermediate 1-C-1

Under the protection of nitrogen, the intermediate 1B-1 (100.75g, 222.09mmol), p-chlorobromobenzene (59.42g, 310.36mmol), tris(dibenzylideneacetone)dipalladium (2.033g, 2.22mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (1.82g, 4.44mmol) and sodium tert-butoxide (32.015g, 333.14mmol) were added to toluene (800mL), heated to reflux (105- 108°C), stirred for 1h; then cooled to room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified with toluene to obtain a white solid intermediate lC-1 (86g) , The yield is 68.6%).

2. Synthesis of other intermediates 1-C-X

Refer to the synthesis method of intermediate 1-C-1 to synthesize each intermediate 1-C-X in Table 4, the difference is that each intermediate 1-B-X is adjusted, and the raw material IV is used instead of p-chlorobromobenzene. Among them, the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 4.

Table 4

5. Synthesis of Intermediate 1-D-X:

Take the intermediate 1-D-1 as an example to illustrate the synthesis of the intermediate 1-D-X.

1. Synthesis of Intermediate 1-D-1

Under the protection of nitrogen, the intermediate 1B-1 (100.75g, 222.09mmol), 4'-chloro-4-bromobiphenyl (59.42g, 222.09mmol), tris(dibenzylideneacetone)dipalladium (2.033g) , 2.22mmol), 2-dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (1.82g, 4.44mmol) and sodium tert-butoxide (32.015g, 333.14mmol) were added to toluene (800mL), Heat to reflux (105-108°C), stir for 1h; then cool to room temperature, wash the reaction solution with water and add magnesium sulfate to dry, filter and remove the solvent from the filtrate under reduced pressure; use toluene to recrystallize and purify the crude product to obtain a white solid intermediate Body 1-D-1 (91 g, yield 64%).

2. Synthesis of other intermediates 1-D-X

Refer to the synthesis method of intermediate 1-D-1 to synthesize each intermediate 1-D-X in Table 5, the difference is that each intermediate 1-B-X is adjusted, and raw material V is used instead of p-chlorobromobenzene. Among them, the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 5.

table 5

6. Synthesis of Intermediate 2-A-X

Take the intermediate 2-A-1 as an example to illustrate the synthesis of the intermediate 2-A-X.

1. Synthesis of Intermediate 2-A-1

Under the protection of nitrogen, aniline (19.557g, 210mmol), 2-bromonaphthalene (41.41g, 200mmol), tris(dibenzylideneacetone)dipalladium (1.83g, 2mmol), 2-dicyclohexylphosphorus-2 ',6'-Dimethoxybiphenyl (1.64g, 4mmol) and sodium tert-butoxide (28.83g, 300mmol) were added to toluene (320mL), heated to reflux (105-108℃), stirred for 1h; then cooled After reaching room temperature, the reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was filtered to remove the solvent under reduced pressure; the crude product was purified by recrystallization using toluene to obtain Intermediate 2-A-1 (28.946 g, yield 66%).

2. Synthesis of other intermediates 2-A-X

Refer to the synthesis method of intermediate 2-A-1 to synthesize each intermediate 2-A-X in Table 6. The difference is that the raw material VI is used instead of aniline, and the raw material VII is used instead of 2-bromonaphthalene. Among them, the main raw materials used, the corresponding intermediate structures, and the synthesis yield results are shown in Table 6.

Table 6

Seven, compound synthesis

Synthesis Example 1: Synthesis of Compound A61:

Under the protection of nitrogen, Intermediate 1C-1 (64g, 113mmol), Intermediate 2-A-2 (27.8g, 113mmol), Tris(dibenzylideneacetone)dipalladium (1.03g, 1.1mmol), 2 -Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (0.93g, 2.2mmol) and sodium tert-butoxide (16.3g, 170mmol) were added to toluene (640mL) and heated to reflux (105-108) ℃), stirred for 1h; then cooled to room temperature, the reaction solution was washed with water and then dried by adding magnesium sulfate, filtered and the filtrate was filtered to remove the solvent under reduced pressure; the crude product was recrystallized and purified with toluene to obtain a white solid compound A61 (52.62g, yield 60%), mass spectrum: m/z=773.4[M+H] ⁺ . The nuclear magnetic data of compound A61, ¹ H NMR (400MHz, CD ₂ Cl ₂ ): 8.04 (d, 1H), 7.90 (s, 1H), 7.78-7.75 (m, 4H), 7.56 (m, 5H), 7.48- 7.39 (m, 8H), 7.37-7.20 (m, 8H), 7.12-6.90 (m, 7H), 2.91 (d, 2H), 2.61 (d, 2H), 2.16 (s, 1H), 1.90 (s, 3H), 1.77 (d, 2H), 1.69 (d, 2H), 1.60 (s, 2H) ppm.

Synthesis examples 2 to 36

Refer to the synthesis method of compound A61 to synthesize other compounds. The difference is that each intermediate 1-C-X is adjusted, and each intermediate 2-A-X is adjusted. Among them, the main raw materials used and the corresponding compound structure, synthesis yield, and mass spectrum results are shown in Table 7.

Table 7

The nuclear magnetic data of compound A239, ¹ H NMR (400MHz, CD ₂ Cl ₂ ): 8.30 (d, 1H), 8.03 (s, 1H), 8.00-7.85 (m, 3H), 7.75 (d, 1H), 7.65- 7.54(m,7H), 7.37-7.20(m,8H), 7.10-6.90(m,9H), 2.90(d,2H), 2.62(d,2H), 2.16(s,1H), 1.90(s, 3H), 1.77 (d, 2H), 1.69 (d, 2H), 1.60 (s, 2H) ppm.

Synthesis Example 37: Synthesis of Compound B1

Under the protection of nitrogen, the intermediate 1D-1 (64g, 100mmol), intermediate 2-A-2 (24.53g, 100mmol), tris(dibenzylideneacetone) two palladium (0.915g, 1mmol), 2- Dicyclohexylphosphorus-2',6'-dimethoxybiphenyl (0.82g, 2mmol) and sodium tert-butoxide (14.415g, 150mmol) were added to toluene (640mL) and heated to reflux (105-108℃) Then, it was cooled to room temperature. The reaction solution was washed with water and dried by adding magnesium sulfate. After filtration, the filtrate was filtered to remove the solvent under reduced pressure. The crude product was recrystallized and purified with toluene to obtain a white solid compound B1 (54.344g, yield 64%). ). Mass spectrum: m/z=849.4 [M+H] ⁺ . The nuclear magnetic data of compound B1 are: ¹ H NMR (CDCl ₃ , 400 Hz): 8.09 (d, 1H), 7.91 (s, 1H), 7.75-7.70 (m, 4H), 7.60-7.53 (m, 13H), 7.46 -7.24(m, 15H), 7.18-7.05(m, 4H), 2.91(d, 2H), 2.61(d, 2H), 2.16(s, 1H), 1.90(s, 3H), 1.77(d, 2H) ), 1.69(d, 2H), 1.60(s, 2H) ppm.

Synthesis examples 38 to 94

Refer to the synthesis method of compound B1 to synthesize the compounds listed in Table 8. The difference is that each intermediate 1-D-X is adjusted, and each intermediate 2-A-X is adjusted. Among them, the main raw materials used and corresponding compound structures, synthesis yields, and mass spectrometry characterization results are shown in Table 8.

Table 8

Among them, the nuclear magnetic data of compound B184: ¹ H NMR (CDCl ₃ , 400Hz): 8.10 (d, 1H), 7.98 (s, 1H), 7.91 (d, 1H), 7.80 (m, 4H), 7.68-7.40 ( m, 12H), 7.34-7.26 (m, 13H), 7.10-6.92 (d, 4H), 2.90 (d, 2H), 2.63 (d, 2H), 2.17 (s, 1H), 1.89 (s, 3H) , 1.77 (d, 2H), 1.70 (d, 2H), 1.60 (s, 2H) ppm.

The nuclear magnetic data of compound B220: ¹ H NMR (CDCl ₃ , 400Hz): 8.36 (d, 1H), 8.05 (d, 2H), 7.96 (s, 1H), 7.88 (m, 2H), 7.78-7.68 (m, 8H),7.65-7.25(m,13H),7.16-7.08(d,5H),6.96-6.90(m,3H),6.87(d,2H), 6.83(d,2H),6.78(d,1H) , 2.91(d, 2H), 2.62(d, 2H), 2.16(s, 1H), 1.90(s, 3H), 1.78(d, 2H), 1.70(d, 2H), 1.60(s, 2H) ppm .

The nuclear magnetic data of compound B280: ¹ H NMR (CDCl ₃ , 400Hz): 8.03-7.91 (m, 5H), 7.86-7.80 (m, 3H), 7.76-7.61 (m, 8H), 7.58-7.45 (m, 4H) ), 7.27-7.10 (m, 9H), 2.92 (d, 2H), 2.624 (d, 2H), 2.18 (s, 1H), 1.91 (s, 3H), 1.78 (d, 2H), 1.71 (d, 2H), 1.60 (s, 2H) ppm.

Preparation and evaluation of organic electroluminescent devices

Example 1

The substrate containing the light reflection layer plated with metallic Ag and the ITO anode (thickness 15nm) was cut into a size of 40mm×40mm×0.7mm, and the photolithography process was used to prepare it into an experiment with a pattern of cathode, anode and insulating layer The substrate (luminescent pixel size is 3mm×3mm), using ultraviolet ozone and O ₂ :N ₂ plasma for surface treatment to increase the work function of the anode (experimental substrate) and remove scum;

Evaporate HAT-CN with a thickness of 10 nm on the anode to form a hole injection layer (HIL);

Next, compound A61 is vapor-deposited on the hole injection layer to form a hole transport layer (HTL) with a thickness of 100 nm;

Vacuum evaporate TCTA on the above hole transport layer to form an electron blocking layer (EBL) with a thickness of 15 nm;

Α, β-ADN was vapor-deposited on the above electron blocking layer, and TBPe was used as a dopant at 3% (weight ratio) to form a light-emitting layer (EML) with a thickness of 20 nm;

TPO and LiQ were vapor-deposited on the light-emitting layer at a weight ratio of 1:1 to form a 28nm electron transport layer (ETL);

Ytterbium (Yb) is vapor-deposited on the above electron transport layer to form an electron injection layer (EIL) with a thickness of 1.5 nm;

Then, on the electron injection layer, magnesium (Mg) and silver (Ag) were vapor-deposited in a weight ratio of 1:10 to form a cathode with a thickness of 12 nm;

Finally, N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-biphenyl-4 with a thickness of 65nm was deposited on the above cathode. 4'-Diamine (DNTPD), as the organic cover layer (CPL). The vapor-deposited device is encapsulated with ultraviolet curable resin in a nitrogen glove box.

Among them, when preparing organic electroluminescent devices, the main material structures used are as follows:

Examples 2～36

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 9 were used instead of Compound A61 of Example 1 when forming the hole transport layer (HTL). For example, in Example 2, compound A65 was used to fabricate an organic electroluminescent device, and in Example 3, compound A63 was used to fabricate an organic electroluminescent device, and the devices of Examples 4 to 36 were sequentially prepared in this order.

Comparative examples 1 to 3

Except that NPB, Compound D1 and Compound D2 were used instead of Compound A61 of Example 1 when forming the hole transport layer (HTL), an organic electroluminescence device was fabricated in the same manner as in Example 1. Among them, the structures of NPB, compound D1 and compound D2 are as follows:

The performance (IVL and lifetime) of the organic electroluminescent devices of the foregoing examples and comparative examples were analyzed, and the results are shown in Table 9. Among them, the driving voltage, luminous efficiency, external quantum efficiency, and color coordinates are ^{tested at a constant current density of 10 mA/cm 2} , and the lifetime of the T95 device is tested at a constant current density of 15 mA/cm ² .

Table 9

The current efficiency of the organic electroluminescent devices in Examples 1 to 36 is at least 9.5% higher than the highest current efficiency (5.59Cd/A) in Comparative Examples 1 to 3; the external quantum of the organic electroluminescent devices in Examples 1 to 36 The efficiency is improved by at least 9.6% compared with the highest external quantum efficiency (11.5%) in Comparative Examples 1 to 3; the T95 lifetime of the organic electroluminescent devices of Examples 1 to 36 is the highest (202h) than the T95 lifetime of Comparative Examples 1 to 3 This is an increase of at least 38.6%. Compared with Comparative Examples 2 and 3, when the driving voltages of Examples 1 to 36 are basically unchanged, the efficiency and life span have been greatly improved.

Example 37

The organic electroluminescence device was prepared by the following process: the anode ITO substrate (thickness 15nm) plated with the Ag alloy light reflection layer was cut into a size of 40mm×40mm×0.7mm, and the photolithography process was used to prepare it to have a cathode, The anode and the experimental substrate with the insulating layer pattern _{are surface treated with ultraviolet ozone and O 2} :N ₂ plasma to increase the work function of the anode (experimental substrate) and remove scum.

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

The hole injection layer (HIL);

The compound NPB is vacuum-evaporated on the hole injection layer to form a thickness of

The first hole transport layer (HTL1).

The compound B1 was evaporated on the first hole transport layer (HTL1) as the second hole transport material (HTL2) with a thickness of

PVK (poly(9-vinylcarbazole, CAS number; 25067-59-8) is vapor-deposited on the second hole transport layer, doped with Ir(piq) ₂ (acac) with a film thickness ratio of 3%, The formation thickness is

Organic light emitting layer (EML).

On the organic light-emitting layer (EML), TPBi and LiQ doped with a film thickness ratio of 1:1 are deposited as the electron transport layer (ETL), and the thickness is

Evaporation on the electron transport layer (ETL)

The Yb serves as the electron injection layer (EIL).

The electron injection layer (EIL) is vapor-deposited with silver (Ag) and magnesium (Mg) doped with a film thickness ratio of 9:1 as the cathode, and the thickness is

The compound CP-1 is vapor-deposited on the cathode as an organic covering layer (CPL) with a thickness of

The vapor-deposited device is encapsulated with ultraviolet-curing resin in a nitrogen glove box.

Among them, in the preparation of organic electroluminescent devices, the structure of the main materials used is as follows:

Examples 38～94

The organic electroluminescence device was fabricated in the same manner as in Example 37, except that the compounds listed in Table 10 were used instead of the compound B1 of Example 37 when forming the second hole transport material (HTL2).

Comparative examples 5-8

Except that Compound D3, Compound D4, Compound D5, and Compound D6 were used to replace Compound B1 of Example 37 when forming the second hole transport material (HTL2), an organic electroluminescence device was fabricated using the same method as Example 37. Among them, the structures of compound D3, compound D4, compound D5 and compound D6 are as follows:

Performance tests were performed on the organic electroluminescent devices prepared in the foregoing Examples 37-94 and Comparative Examples 5-8. The results are shown in Table 10. The driving voltage, efficiency, and color coordinates are at a constant current density of 10 mA/cm ² The T95 device life is tested at a constant current density of 20 mA/cm ² .

Table 10

Referring to the results of Table 10, compared with the organic electroluminescent devices of Comparative Examples 5-8, the organic electroluminescent devices obtained in Examples 37 to 94 have the characteristics of high efficiency and long life when the color coordinate CIEx is equivalent. . Specifically, the current efficiency of the organic electroluminescent devices of Examples 37 to 94 is 30.3Cd/A to 34.6Cd/A, which is at least 7.1% higher than the highest (28.3Cd/A) in the devices of Comparative Examples 5 to 8 The T95 device lifetime of the organic electroluminescent devices in Examples 37-94 is 470h-510h, which is at least 17.2% higher than the highest (420h) in the devices of Comparative Examples 5-8. In addition, the driving voltage of the organic electroluminescent devices in Examples 37 to 94 was 3.51V to 3.78V, which was at least 0.11V lower than the lowest driving voltage (3.89V) of the devices in Comparative Examples 5 to 8.

It can be seen that the nitrogen-containing compound of the present application is used as a hole transport material, so that the organic electroluminescent device can further improve the efficiency and lifetime of the device while ensuring a lower driving voltage.

Claims

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

Wherein, L is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 6-30 carbon atoms; the substituents in L are each independently selected from: deuterium , Halogen groups, cyano groups, aryl groups with 6-12 carbon atoms, heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, and those with 1-10 carbon atoms Haloalkyl, cycloalkyl with 3-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkylthio with 1-10 carbon atoms, trialkyl with 3-12 carbon atoms Silicon-based

Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms The substituents in Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and the number of carbon atoms is 3-18 heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and those with 1-10 carbon atoms Alkoxy group, alkylthio group having 1-10 carbon atoms, trialkylsilyl group having 3-12 carbon atoms;

In Ar 1 , Ar 2 , Ar 3 and L, when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form a 5- to 13-membered saturation with the atoms to which they are connected together. Or unsaturated ring;

R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, carbon atom Cycloalkyl groups with 3-10 carbon atoms, aryl groups with 6-20 carbon atoms, heteroaryl groups with 3-20 carbon atoms, alkoxy groups with 1-10 carbon atoms, and 1 carbon atoms -10 alkylthio group, trialkylsilyl group with 3-12 carbon atoms;

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

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.
The nitrogen-containing compound according to claim 1, wherein the structure of the nitrogen-containing compound is as shown in chemical formula 1:

Wherein, L is selected from the group shown in chemical formula 1-1;

R 1 and R 2 are the same or different from each other, and are each independently selected from: deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, number of carbon atoms Cycloalkyl groups of 3-10, aryl groups of 6-20 carbon atoms, heteroaryl groups of 3-20 carbon atoms, alkoxy groups of 1-10 carbon atoms, 1- 10 alkylthio groups, trialkylsilyl groups with 3-12 carbon atoms;

R 3 is selected from deuterium, halogen group, cyano group, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;

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

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 or 4, when n 3 is greater than 1, any two R 3 are the same or different;

Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

The substituents in Ar 1 , Ar 2 , and Ar 3 are the same or different from each other, and are each independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6-20 carbon atoms, and those with 3-18 carbon atoms Heteroaryl groups, alkyl groups having 1-10 carbon atoms, haloalkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, alkoxy groups having 1-10 carbon atoms, Alkylthio with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms; in Ar 1 , Ar 2 , and Ar 3 , when there are two substituents on the same atom, any Optionally, two substituents are connected to each other to form a 5-13 membered saturated or unsaturated ring together with the atoms to which they are commonly connected.
The nitrogen-containing compound according to claim 1, wherein the structure of the nitrogen-containing compound is as shown in chemical formula 2:

Wherein, L is selected from substituted or unsubstituted group Q with 7-30 carbon atoms, group Q is selected from: bicyclic fused arylene, tricyclic fused arylene, bicyclic fused heteroarylene And one of the tricyclic fused heteroarylene groups, or selected from: monocyclic arylene, monocyclic heteroarylene, bicyclic fused arylene, tricyclic fused arylene, bicyclic fused arylene Optionally at least two groups in a heteroaryl group and a tricyclic fused heteroarylene group are connected to each other via a single bond to form a divalent group;

The substituted group Q means that the group Q has one or more substituents, and the substituents are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-12 carbon atoms , Heteroaryl groups with 3-10 carbon atoms, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, number of carbon atoms Is an alkoxy group having 1-10, an alkylthio group having 1-10 carbon atoms, and a trialkylsilyl group having 3-12 carbon atoms;

Ar 1 , Ar 2 and Ar 3 are the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms ；

The substituents in Ar 1 , Ar 2 and Ar 3 are the same or different, and are each independently selected from: deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, 3-18 carbon atom Heteroaryl groups, alkyl groups with 1-10 carbon atoms, haloalkyl groups with 1-10 carbon atoms, cycloalkyl groups with 3-10 carbon atoms, and alkoxy groups with 1-10 carbon atoms , Alkylthio groups with 1-10 carbon atoms, trialkylsilyl groups with 3-12 carbon atoms;

In Ar 1 , Ar 2 , Ar 3 and substituted groups Q, when there are two substituents on the same atom, optionally, the two substituents are connected to each other to form 5- 13-membered saturated or unsaturated ring;

R 1 and R 2 are the same or different, and are independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, haloalkyl group with 1-10 carbon atoms, and the number of carbon atoms is 3-10 cycloalkyl, carbon 6-20 aryl, carbon 3-20 heteroaryl, carbon 1-10 alkoxy, carbon 1-10 The alkylthio group, the trialkylsilyl group with 3-12 carbon atoms;

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

n 2 represents the number of substituents 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.
The nitrogen-containing compound according to claim 2, wherein Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and 4 to 4 carbon atoms. 25 substituted or unsubstituted heteroaryl.
The nitrogen-containing compound according to claim 2, wherein Ar 1 is a substituted or unsubstituted group Z 1 , Ar 2 is a substituted or unsubstituted group Z 2 , and Ar 3 is a substituted or unsubstituted group Group Z 3 , wherein the unsubstituted groups Z 1 , Z 2 and Z 3 are each independently selected from the group consisting of:

The substituted groups Z 1 , Z 2 and Z 3 each independently have one or two or more substituents, and the substituents are independently selected from: deuterium, cyano, fluorine, alkyl with 1 to 4 carbon atoms, Haloalkyl groups with 1-4 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, alkoxy groups with 1-4 carbon atoms, alkylthio groups with 1-4 carbon atoms, carbon atoms It is a 3-7 trialkylsilyl group.
The nitrogen-containing compound according to claim 2, wherein Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of:
The nitrogen-containing compound according to claim 2, wherein R 1 and R 2 are each independently selected from the group consisting of deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. 4 haloalkyl, carbon 5-10 cycloalkyl, carbon 6-15 aryl, carbon 3-15 heteroaryl, carbon 1-4 alkoxy Group, alkylthio group having 1 to 4 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms.
The nitrogen-containing compound according to claim 2, wherein R 3 is selected from the group consisting of deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, carbon atom An alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, and a trialkylsilyl group having 3 to 7 carbon atoms.
The nitrogen-containing compound according to claim 2, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:
The nitrogen-containing compound according to claim 3, wherein R 1 and R 2 are the same or different, and are independently selected from the group consisting of deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, carbon A haloalkyl group having 1 to 4 atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 10 carbon atoms, and a carbon number of 1 -4 alkoxy, carbon 1-4 alkylthio, carbon 3-7 trialkylsilyl.
The nitrogen-containing compound according to claim 3, wherein L is selected from substituted or unsubstituted groups Q with 8-25 carbon atoms.
The nitrogen-containing compound according to claim 3 or 11, wherein the substituent in the substituted group Q is selected from the group consisting of deuterium, fluorine, cyano, alkyl with 1 to 4 carbon atoms, and It is a 5-10 cycloalkyl group, a carbon number of 1-4 alkoxy group, a carbon number of 1-4 alkylthio group, a carbon number of 3-7 trialkylsilyl, and a phenyl group.
The nitrogen-containing compound according to claim 3, wherein L is selected from the group consisting of the following groups:
The nitrogen-containing compound according to claim 3, wherein Ar 1 , Ar 2 and Ar 3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and 5 to 5 carbon atoms. 25 substituted or unsubstituted heteroaryl.
The nitrogen-containing compound according to claim 3 or 14, wherein the substituents in Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of deuterium, fluorine, cyano, and carbon atoms of 1 to 4 Alkyl groups, haloalkyl groups having 1 to 4 carbon atoms, cycloalkyl groups having 5 to 10 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, alkylthio groups having 1 to 4 carbon atoms, A trialkylsilyl group having 3-7 carbon atoms.
The nitrogen-containing compound according to claim 3, wherein Ar 1 , Ar 2 and Ar 3 are each independently selected from the group consisting of the following groups:
The nitrogen-containing compound according to claim 3, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:
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 one described in any one of claims 1-17 Nitrogen-containing compounds.
The electronic component according to claim 18, wherein the functional layer includes a hole transport layer, and the hole transport layer includes the nitrogen-containing compound.
The electronic component according to claim 18 or 19, wherein the electronic component is an organic electroluminescence device or a photoelectric conversion device.
An electronic device, characterized by comprising the electronic component according to any one of claims 18-20.