阅读说明：本技术 一种有机化合物以及使用其的电子元件和电子装置 (Organic compound, and electronic element and electronic device using same ) 是由 马林楠 南朋 金荣国 李应文 于 2021-09-09 设计创作，主要内容包括：本申请属于有机材料领域,涉及一种有机化合物以及使用其的电子元件和电子装置,所述有机化合物具有如化学式1所示的结构,所述有机化合物应用于有机电致发光器件中,可显著改善器件的性能。(This application is inThe field of organic materials relates to an organic compound, and an electronic element and an electronic device using the organic compound, wherein the organic compound has a structure shown in chemical formula 1, and the organic compound is applied to an organic electroluminescent device and can remarkably improve the performance of the device.)

1. An organic compound having a structure represented by formula 1:

in formula 1, A is selected from adamantyl, norbornyl or cyclohexyl;

Ar₁selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂is selected fromWherein X is selected from C (R)₄R₅)、N(R₆)、O、S、Si(R₇R₈)，Represents a chemical bond;

R₄、R₅、R₆、R₇、R₈the same or different, and each independently selected from hydrogen, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, aryl with 7-17 carbon atoms substituted by alkyl with 1-5 carbon atoms, and heteroaryl with 3-12 carbon atoms; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-15 membered ring;

R₁、R₂and R₃The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 3-12 carbon atoms, and trialkylsilyl group with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₃Represents R₃Number of (2), n₁And n₂Each independently selected from 0, 1,2, 3 or 4, n₃Selected from 0, 1,2, 3,4 or 5; and when n is₁When greater than 1, any two R₁The same or different; when n is₂When greater than 1, any two R₂The same or different; when n is₃When greater than 1, any two R₃The same or different;

L₁and L₂The same or different, and each independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;

L₁、L₂、Ar₁wherein the substituents are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms.

2. The organic compound according to claim 1, wherein the structure of the organic compound is represented by formula 1:

in formula 1, A is selected from adamantyl, norbornyl or cyclohexyl;

Ar₁selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂is selected fromWherein X is selected from C (R)₄R₅)、N(R₆)、O、S、Si(R₇R₈)，Represents a chemical bond;

R₄、R₅、R₆、R₇、R₈the same or different, and each independently selected from the group consisting of C1-5 alkyl, C6-12 aryl, C7-17 aryl substituted by C1-5 alkyl, and C3-12 heteroaryl; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-15 membered ring;

R₁、R₂and R₃The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 3-12 carbon atoms, and trialkylsilyl group with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₃Represents R₃Number of (2), n₁And n₂Each independently selected from 0, 1,2, 3 or 4, n₃Selected from 0, 1,2, 3,4 or 5; and when n is₁When greater than 1, any two R₁The same or different; when n is₂When greater than 1, any two R₂The same or different; when n is₃When greater than 1, any two R₃The same or different;

L₁and L₂The same or different, and each independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;

L₁、L₂、Ar₁wherein the substituents are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms.

3. The organic compound according to claim 1 or 2, wherein Ar is Ar₁Selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and aryl groups having 5 to 20 carbon atomsSubstituted or unsubstituted heteroaryl.

4. The organic compound according to claim 1 or 2, wherein Ar is Ar₁Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylfuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthryl;

preferably, Ar₁Each substituent in (1) is independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl.

5. The organic compound according to claim 1 or 2, wherein L₁And L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 10 to 20 carbon atoms;

preferably, L₁And L₂Each substituent in (1) is independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl.

6. The organic compound according to claim 1 or 2, wherein L₁And L₂Each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V having one or more substituents, aThe substituents are each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl; when the number of the substituents is more than 1, the substituents may be the same or different.

7. The organic compound according to claim 1 or 2, wherein R₁、R₂And R₃Each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl, dibenzofuranyl, dibenzothiophenyl.

8. The organic compound according to claim 1 or 2, wherein R₄、R₅、R₆、R₇、R₈Each independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyrimidinyl, pyridinyl; or, R₄And R₅Forming a fluorene ring; or, R₇And R₈Forming a fluorene ring;

preferably, R₄、R₅、R₆、R₇、R₈Each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyrimidinyl, pyridinyl; or, R₄And R₅Forming a fluorene ring; or, R₇And R₈A fluorene ring is formed.

9. The organic compound according to claim 1 or 2, wherein Ar is Ar₂Selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl; when the number of the substituents is more than 1, the substituents may be the same or different.

10. The organic compound according to claim 1 or 2, wherein Ar is Ar₂Selected from the group consisting of:

11. the organic compound of claim 1 or 2, wherein a is selected from the group consisting of:

12. the organic compound according to claim 1 or 2, wherein the organic compound is selected from one or more of the following compounds:

13. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to any one of claims 1 to 12.

14. The electronic element according to claim 13, wherein the functional layer comprises an electron blocking layer containing the organic compound;

preferably, the electronic element is an organic electroluminescent device.

15. An electronic device comprising the electronic component of claim 13 or 14.

Technical Field

The application belongs to the technical field of organic materials, and particularly provides an organic compound, and an electronic element and an electronic device using the organic compound.

Background

With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.

Taking an organic electroluminescent device as an example, the organic electroluminescent device generally comprises an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.

Disclosure of Invention

An object of the present application is to provide an organic compound which can be used in an electronic element to improve voltage characteristics, light emission efficiency, and a service life of the electronic element, and an electronic element and an electronic device using the same.

In order to achieve the above object, the present application provides, in a first aspect, an organic compound having a structure represented by formula 1:

in formula 1, A is selected from adamantyl, norbornyl or cyclohexyl;

Ar₁selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂is selected fromWherein X is selected from C (R)₄R₅)、N(R₆)、O、S、Si(R₇R₈)，Represents a chemical bond;

R₄、R₅、R₆、R₇、R₈the same or different, and each independently selected from hydrogen, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, aryl with 7-17 carbon atoms substituted by alkyl with 1-5 carbon atoms, and heteroaryl with 3-12 carbon atoms; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-15 membered ring;

R₁、R₂and R₃The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 3-12 carbon atoms, and trialkylsilyl group with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₃Represents R₃Number of (2), n₁And n₂Each independently selected from 0, 1,2, 3 or 4, n₃Selected from 0, 1,2, 3,4 or 5; and when n is₁When greater than 1, any two R₁The same or different; when n is₂When greater than 1, any two R₂The same or different; when n is₃When greater than 1, any two R₃The same or different;

L₁and L₂The same or different, each independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;

L₁、L₂、Ar₁wherein the substituents are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms.

Alternatively, R₄、R₅、R₆、R₇、R₈The same or different, and each independently selected from the group consisting of C1-5 alkyl, C6-12 aryl, C7-17 aryl substituted by C1-5 alkyl, and C3-12 heteroaryl; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-15 membered ring.

A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound as provided in the first aspect of the present application.

A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

The organic compound is a triarylamine structure simultaneously comprising 1, 8-diphenyl naphthalene group, cycloparaffin and dibenzo five-membered ring, in the structure, the 1, 8-diphenyl naphthalene group has better electronic blocking capability, the triarylamine can increase the conjugation of molecules in the structure, effectively improve the efficiency and enhance the film forming performance of the molecules, in addition, the cycloparaffin structure with large steric hindrance effectively improves the stacking effect of the molecules, integrally increases the rigidity and the thermal stability of the molecules, and further improves the service life of the organic electroluminescent device.

Additional features and advantages of the present application will be described in detail in the detailed description which follows.

Drawings

The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application.

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

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

Description of the reference numerals

100. Anode 200, cathode 300, functional layer 310, hole injection layer

321. Hole transport layer 322, electron blocking layer 330, organic light emitting layer 341, hole blocking layer

340. Electron transport layer 350, electron injection layer 400, first electronic device

Detailed Description

The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.

The terms "the" and "said" are used to indicate the presence of one or more elements/components/etc.; the terms "comprising," "including," and "containing" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.

In a first aspect of the present application, there is provided an organic compound having a structure represented by formula 1:

in formula 1, A is selected from adamantyl, norbornyl or cyclohexyl;

Ar₁selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₂is selected fromWherein X is selected from C (R)₄R₅)、N(R₆)、O、S、Si(R₇R₈)，Represents a chemical bond;

R₄、R₅、R₆、R₇、R₈the same or different, and each independently selected from hydrogen, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, aryl with 7-17 carbon atoms substituted by alkyl with 1-5 carbon atoms, and heteroaryl with 3-12 carbon atoms; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-to 15-membered ring, for example, a cyclopentyl group, a cyclohexyl group, a fluorene ring, etc.;

R₁、R₂and R₃The same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl group with 1-5 carbon atoms, aryl group with 6-12 carbon atoms, heteroaryl group with 3-12 carbon atoms, and trialkylsilyl group with 3-12 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₃Represents R₃Number of (2), n₁And n₂Each independently selected from 0, 1,2, 3Or 4, n₃Selected from 0, 1,2, 3,4 and 5; and when n is₁When greater than 1, any two R₁The same or different; when n is₂When greater than 1, any two R₂The same or different; when n is₃When greater than 1, any two R₃The same or different;

L₁and L₂The same or different, each independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;

L₁、L₂、Ar₁wherein the substituents are the same or different and are independently selected from deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, heteroaryl groups having 3 to 12 carbon atoms, and trialkylsilyl groups having 3 to 12 carbon atoms.

Alternatively, R₄、R₅、R₆、R₇、R₈The same or different, and each independently selected from the group consisting of C1-5 alkyl, C6-12 aryl, C7-17 aryl substituted by C1-5 alkyl, and C3-12 heteroaryl; or, R₄And R₅Forming a saturated or unsaturated 3-15 membered ring; or, R₇And R₈Forming a saturated or unsaturated 3-15 membered ring.

In the present application, a is an unsubstituted adamantyl group, an unsubstituted norbornyl group, or an unsubstituted cyclohexane group.

In the present application, it is preferred that,Included

as used herein, the recitations "each … … independently" and "… … independently" and "… … independently selected from" are interchangeable and are to be understood in a broad sense to mean that the same may be expressed in different groups between the same symbolsMay also mean that the particular options expressed between the same symbols do not affect each other in the same group. For example,') "Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.

In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, a trialkylsilyl group, an alkyl group, an aryl group or a heteroaryl group.

In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L₂Selected from substituted arylene groups having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12. For example: ar (Ar)₁Is composed ofThe number of carbon atoms is 10; l is₂Is composed ofThe number of carbon atoms is 12. In addition, A is represented by Ar₁Group (c) attached to when Ar₁When unsubstituted aryl (heteroaryl) group is present, A is directly attached to the aryl (heteroaryl) group, when Ar is₁In the case of a substituted aryl (heteroaryl) radical (the substituent being Rc), Ar₁May be attached to an aromatic hydrocarbon (heteroaromatic hydrocarbon)) The substituent Rc may be bonded to the above-mentioned group, and is preferably directly bonded to an aryl (heteroaryl) group. An "unsubstituted aryl (heteroaryl) group" means an unsubstituted aryl or unsubstituted heteroaryl group, and a "substituted aryl (heteroaryl) group" means a substituted aryl or substituted heteroaryl group.

In the present application, "alkyl" may include straight chain alkyl or branched chain alkyl. Alkyl groups may have 1 to 5 carbon atoms, and numerical ranges such as "1 to 5" refer herein to each integer in the given range; for example, "alkyl group of 1 to 5 carbon atoms" means an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, and specific examples include, but are not limited to, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, and pentyl group.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.

In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms are substituted with a group such as deuterium atom, halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.

In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and the N-phenylcarbazolyl and the N-pyridylcarbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.

In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.

In the present application, the number of carbon atoms of the aryl group as the substituent may be 6 to 12, for example, the number of carbon atoms may be 6, 7, 8, 9,10, 11, 12, and specific examples of the aryl group as the substituent include, but are not limited to, phenyl, naphthyl, biphenyl, and the like.

In the present application, the number of carbon atoms of the heteroaryl group as the substituent may be 3 to 12, for example, the number of carbon atoms may be 3,4, 5, 6, 7, 8, 9,10, 11, 12, and specific examples of the heteroaryl group as the substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl.

In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.

Specific examples of the trialkylsilyl group herein include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.

In the present application, the spirofluorenyl group may be a spirobifluorenyl group.

As used herein, an delocalized linkage refers to a single bond extending from a ring systemIt means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.

For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).

As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the dibenzofuranyl group represented by formula (X '-1) to formula (X' -4) includes any of the possible attachment means shown in formulas (X '-1) to (X' -4).

The meaning of the connection or substitution is the same as that of the connection or substitution, and will not be described further.

In one embodiment of the present application, Ar₁Selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 5-20 carbon atoms. For example, Ar₁Selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

Alternatively, Ar₁Wherein the substituent is selected from deuterium, cyano, fluorine, alkyl with 1-5 carbon atoms, trimethylsilyl, aryl with 6-12 carbon atoms and heteroaryl with 5-12 carbon atoms.

Alternatively, Ar₁Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylfuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyl, and substituted or unsubstituted phenanthryl.

Preferably, Ar₁Each substituent in (1) is independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl.

In the present application, unsubstituted carbazolyl groups include

Alternatively, Ar₁Selected from the group consisting of substituted or unsubstituted groups Q selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group Q has one or two or more substituents therein, each of which is independently selected from: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl; when the number of substituents of Q is more than 1, the substituents may be the same or different.

Alternatively, Ar₁Selected from the group consisting of:

further optionally, Ar₁Selected from the group consisting of:

in one embodiment of the present application, L₁And L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 10 to 20 carbon atoms.For example, L₁And L₂Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

Preferably, L₁And L₂Each substituent in (1) is independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl.

Alternatively, L₁And L₂Each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted fluorenylene group.

Preferably, L₁And L₂Each substituent in (1) is independently selected from deuterium, cyano, fluoro, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl.

Alternatively, L₁And L₂Each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group V has one or more substituents therein, each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl; when the number of the substituents of V is more than 1, the substituents may be the same or different.

Alternatively, L₁And L₂Each independently selected from the group consisting of a single bond, the following groups:

further optionally, L₁And L₂Each independently selected from the group consisting of a single bond, the following groups:

in one embodiment of the present application, R₁、R₂And R₃Each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl, dibenzofuranyl, dibenzothiophenyl.

Alternatively, R₄、R₅、R₆、R₇、R₈Each independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyrimidinyl, pyridinyl; or, R₄And R₅Forming a fluorene ringOr, R₇And R₈Forming a fluorene ring

Preferably, R₄、R₅、R₆、R₇、R₈Each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyrimidinyl, pyridinyl; or, R₄And R₅Forming a fluorene ring; or, R₇And R₈A fluorene ring is formed.

Alternatively, Ar₂Selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted dibenzothiophenylUnsubstituted fluorenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted silafluorenyl group, substituted or unsubstituted spirofluorenyl group.

Preferably, Ar₂Each substituent in (1) is independently selected from deuterium, cyano, fluoro, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl.

Alternatively, Ar₂Selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group W has one or two or more substituents each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, trimethylsilyl; when the number of substituents of W is more than 1, the substituents may be the same or different.

Alternatively, Ar₂Selected from the group consisting of:

further optionally, Ar₂Selected from the group consisting of:

alternatively, a is selected from the group consisting of:

optionally, the organic compound is selected from the following organic compounds:

a second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound provided in the first aspect of the present application.

In a specific embodiment, the functional layer comprises an electron blocking layer containing the organic compound. Optionally, the electronic element is an organic electroluminescent device.

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

In one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO₂Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.

Alternatively, the hole transport layer 321 may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds, which are not specifically limited in this application. For example, the hole transport layer 321 may be NPB.

Alternatively, the electron blocking layer 322 may be composed of the organic compound provided herein, or may be composed of the organic compound provided herein together with other materials selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other compounds conventionally employed in electron blocking layers by those skilled in the art. For example, the electron blocking layer may be an organic compound of the present application.

Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, or may include a host material and a dopant material. Alternatively, the organic light emitting layer 330 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfer energy to the dopant material, thereby enabling the dopant material to emit light.

The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be BH-01.

The doping material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the doping material of the organic light emitting layer 330 may be BD-01.

The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of ET-06 and LiQ.

In the present application, the cathode 200 may comprise a cathode material that is a material with small outgassing that facilitates electron injection into the functional layerA material of work. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.

Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be F4-TCNQ.

Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may be Yb.

Alternatively, as shown in fig. 1, a hole blocking layer 341 may or may not be disposed between the organic light emitting layer 330 and the electron transporting layer 340, and the material of the hole blocking layer 341 is well known in the art and will not be described herein again.

A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.

The following will specifically explain the method for synthesizing the organic compound of the present application by referring to the synthesis examples, but the present application is not limited thereto.

Compounds of synthetic methods not mentioned in this application are all commercially available starting products.

Synthetic examples

Synthesis of intermediate IM A-X

In N₂To a 1000mL three-necked flask, 8-phenyl-1-naphthalene boronic acid (100g, 0.403mol), p-bromoiodobenzene (103.7g, 0.366mol), and K were added under protection₂CO₃(101.3g，0.733mol)、TBAB(2.3g，0.007mol)、Pd(PPh₃)₄(4.2g, 0.004mol), PhMe (600mL), EtOH (200mL) and H₂O (100mL), refluxing and stirring at 80 ℃ for 12h, stopping the reaction, cooling the reaction solution to room temperature, extracting with deionized water/toluene, washing the organic phase to neutrality with water, adding anhydrous magnesium sulfate to remove water, filtering, concentrating the filtrate, and adding dichloromethaneThe eluent was passed through a column (1: 5) with n-heptane (v/v) to give IM A-1 as a white solid (117.9g, 90% yield).

IM A-X shown in Table 1 (X is 2 or 3) was synthesized by referring to the method of IM A-1, except that the starting material 1 was used in place of p-bromoiodobenzene. Wherein, the raw material 1, the synthesized intermediate and the yield thereof are shown in table 1.

TABLE 1

Synthesis of intermediate IM B-Y

In N₂Under protection, 1-adamantanol (100g, 0.656mol), bromobenzene (103.2g, 0.656mol) and dichloromethane (800mL) are added into a round-bottom flask, the temperature is reduced to 0-5 ℃, trifluoromethanesulfonic acid (147.8g, 0.985mol) is added dropwise, the reaction is stopped after stirring at constant temperature for 3h, deionized water (600mL) is added into the reaction liquid to be neutral, dichloromethane (100mL) is added for extraction, organic phases are combined, anhydrous magnesium sulfate is added for dehydration, the mixture is concentrated after filtration, and the obtained crude product is purified by silica gel column chromatography by using n-heptane as an eluent to obtain white solid IM B-1(106.2g, yield 55.4%).

IM B-Y was synthesized by reference to the procedure for IM B-1, except that starting material 2 was used instead of 1-adamantanol and starting material 3 was used instead of bromobenzene. The main raw materials used, the intermediates synthesized and the yields thereof are shown in table 2.

TABLE 2

Synthesis of intermediate IM C1-2 and intermediate IM C2-2

In N₂Under protection, stirring 2,2' -bisbromobenzene (100g, 320mmol) and THF (500mL) in a 1000mL three-necked bottle for dissolving, reducing the reaction temperature to-78 ℃, dropwise adding n-butyl lithium (280mL, 2.5M, 710mmol), reacting for 1h, adding phenyltrichlorosilane (130mL, 800mmol), slowly raising the temperature to normal temperature, stirring for reacting for 12h, extracting the reaction solution with dichloromethane and water after the reaction is stopped, washing the organic phase to neutrality with water, drying with sodium sulfate, and passing through a column with dichloromethane as an eluentThe post-column solution was concentrated, recrystallized from dichloromethane to n-heptane (v/v) at 1: 4, and filtered to obtain IM C1-1(46.8g, yield 50%).

In N₂Under protection, IM C1-1(46.8g, 160mmol) and THF (300mL) were stirred and dissolved in a 500mL three-necked flask, the reaction temperature was lowered to-78 ℃, n-butyllithium (140.8mL, 2.5M, 352mmol) was added dropwise, after 1h of reaction, 3-bromoaniline (55g, 320mmol) was added, the temperature was slowly raised to room temperature, the reaction was stirred for 12h, after the reaction was stopped, the reaction mixture was extracted with dichloromethane and water, the organic phase was washed with water to neutrality, dried with sodium sulfate, passed through a column using dichloromethane as eluent, the post-column solution was concentrated, recrystallized from ethyl acetate to n-heptane (v/v) at 1: 10, and after filtration, IM C1-2(22.5g, yield 41%) was obtained.

IM C2-2 was synthesized by reference to the procedure of IM C1-2, except that 2-bromoaniline was used instead of 3-bromoaniline, wherein the main starting materials used, the intermediates synthesized, and their yields are shown in Table 3.

TABLE 3

Synthesis of intermediate IM C3-2

In N₂Under protection, 9-diphenyl-9H-9-silafluorene (27g, 80.8mmol) was dissolved in 300mL chloroform, the mixture was placed at 0 ℃ and stirred well, bromine (12.9g, 80.8mmol) was added dropwise to the mixture, then the temperature was gradually raised to room temperature, the reaction was stopped after 8H at room temperature, water was added to quench, the organic phase was washed three times with water, dried over sodium sulfate, recrystallized with ethanol, and filtered to give IM C3-1(23.6g, 71% yield).

In N₂Under protection, IM C3-1(24.8g, 60mmol) was dissolved in 100mL THF, Cu (0.2g, 5 mol%) was added, the reaction was stirred at 110 ℃ for 12h, after completion of the reaction, extraction was performed with dichloromethane and water, the organic phase was washed three times with water, dried over sodium sulfate, filtered, and then eluted with ethyl acetate/n-heptane (v/v) ═ 1: 10 to give IM C3-2(17g, 81% yield).

Synthesis of intermediate IM C4-2

In N₂Under protection, 3-chloro-2-iodoaniline (25.3g, 100mmol), chloroneboronic acid (15.6g, 100mmol), potassium carbonate (27.6g, 200mmol), TBAB (1.29g, 4mmol), Pd (PPh)₃)₄(2.31g, 2mmol), toluene (150mL), ethanol (75mL) and water (25mL) were charged in a 500mL three-necked flask, reacted at 80 ℃ for 12 hours, then extracted with toluene and water, the organic phase was washed with water to neutrality, dried over anhydrous sodium sulfate, washed with toluene as an eluent, passed through a silica gel column, concentrated, and recrystallized with dichloromethane: n-heptane (v/v) ═ 1: 5 to give IM C4-1(21.9g, 91% yield).

In N₂Under protection, IM C4-1(21.9g, 92mmol) and THF (160mL) are stirred and dissolved in a 25mL three-necked bottle, the reaction temperature is reduced to-78 ℃, n-butyl lithium (80.9mL, 2.5M, 202.4mmol) is added dropwise, after 1h of reaction, diphenyldichlorosilane (46.6g, 184mmol) is added, the temperature is slowly raised to the normal temperature, the reaction is stirred for 12h, after the reaction is stopped, the reaction solution is extracted by dichloromethane and water, the organic phase is washed to be neutral by water, dried by sodium sulfate, and passes through a column by dichloromethane serving as eluent, after the column is concentratedThe resulting solution was recrystallized from ethyl acetate and n-heptane (v/v) at a ratio of 1: 20, and filtered to obtain IM C4-2(12.4g, yield 38.5%).

Synthesis of intermediate IM C-Z

In N₂Under protection, adding IM A-1(0.056mol, 20g), IM C1-2(0.056mol, 19.57g) and toluene (160mL) into a 250mL three-neck round-bottom flask, refluxing and stirring at 108 ℃ for 30min, cooling to 70-80 ℃, adding t-BuONa (0.112mol, 10.76g), x-Phos (0.001mol, 0.53g) and Pd₂(dba)₃(0.0005mol, 0.4576g), after the temperature of the system is stable, the reaction is stopped after refluxing for 4h, after the reaction solution is cooled to room temperature, 100mL of deionized water is added, extraction is carried out with toluene/water, the organic phase is washed to neutrality with water, anhydrous magnesium sulfate is added for water removal, concentration is carried out after filtration, and silica gel column is passed through with an eluent of dichloromethane to n-heptane (v/v) ═ 1: 4, so as to obtain white solid IM C-1(29.9g, yield 85%).

The IM C-Z listed in Table 4 was synthesized by reference to the procedure for IM C-1, except that feed 4 was used in place of IM A-1 and feed 5 was used in place of IM C1-2. The main raw materials used, the intermediates synthesized, and the yields thereof are shown in table 4.

TABLE 4

Synthesis of Compound X

In N₂Adding IM B-1(8.85g, 30.4mmol), IM C-1(19.08g, 30.4mmol) and toluene (100mL) into a 250mL three-neck round-bottom flask, refluxing and stirring at 108 ℃, dissolving the solution until the solution is clear, cooling to 70-80 ℃, adding sodium tert-butoxide (4.4g, 45.7mmol), s-Phos (0.25g, 0.61mmol) and Pd₂(dba)₃(0.28g, 0.330mmol), carrying out reflux reaction for 6h, stopping the reaction, cooling the reaction temperature to room temperature, extracting the reaction solution by using toluene and deionized water, washing the reaction solution to be neutral by water, adding anhydrous magnesium sulfate to remove water, passing the reaction solution through a column by using ethyl acetate and n-heptane (v/v) ═ 1: 10 as an eluent, concentrating the liquid after the column, recrystallizing the liquid by using toluene and n-heptane, and filtering to obtain a white solid compound 2(21.7g, yield 85%); mass spectrum (M/z) 838.38[ M + H [ ]]⁺。

The compounds shown in Table 5 were synthesized by the method of reference to Compound 2, except that starting material 6 was used in place of IM B-1 and starting material 7 was used in place of IM C-1. The main raw materials used, the synthesized compounds and their yields, mass spectra are shown in table 5:

TABLE 5

The nuclear magnetic data for some of the compounds are as follows:

device embodiments

Example 1: blue organic electroluminescent device

The anode was prepared by the following procedure: will have a thickness ofThe ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O₂∶N₂The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.

F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness ofAnd NPB is vapor-deposited on the hole injection layer to form a thickness ofA Hole Transport Layer (HTL).

The compound 2 of the present application was vacuum-deposited on the hole transport layer to a thickness ofElectron Blocking Layer (EBL).

On the electron blocking layer, BH-01 and BD-01 are evaporated together at a film thickness ratio of 98% to 2% to form a film with a thickness ofBlue light emitting layer (EML).

ET-06 and LiQ are formed by evaporation with a film thickness ratio of 1: 1A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layerThen magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer at a film thickness ratio of 1: 9 to form an Electron Injection Layer (EIL) having a thickness ofThe cathode of (1).

The thickness of the vapor deposition on the cathode is set toForming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.

Examples 2 to 78

An organic electroluminescent device was fabricated using the same method as example 1, except that compounds shown in table 7 below were each substituted for compound 2 in forming the electron blocking layer.

Comparative examples 1 to 4

An organic electroluminescent device was fabricated by the same method as in example 1, except that compound a, compound B, compound C, and compound D were used instead of compound 2, respectively, in forming the electron blocking layer.

The main material structures used in the above examples and comparative examples are shown in table 6 below:

TABLE 6

For the organic electroluminescent device prepared as above, at 20mA/cm²The device performance was analyzed under the conditions shown in table 7 below:

TABLE 7

From the results in table 7, it is known that the driving voltage of the organic electroluminescent device prepared by using the compound used in the present invention as the electron blocking layer is reduced by at least 0.17V, the luminous efficiency (Cd/a) is improved by at least 13.36%, the external quantum efficiency is improved by at least 13.42%, the lifetime is improved by at least 6%, and the lifetime can be improved by at most 82h in examples 1 to 78 of the compound used as the electron blocking layer, compared with the device comparative examples 1 to 4 corresponding to the known compound.

The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application.

It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.

In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.