阅读说明：本技术 一种含氮化合物以及使用其的电子元件和电子装置 (Nitrogen-containing compound, and electronic element and electronic device using same ) 是由 马天天 杨敏 南朋 于 2020-10-21 设计创作，主要内容包括：本申请属于有机材料技术领域,具体涉及一种含氮化合物以及使用其的电子元件和电子装置,该有机化合物具有式F-1所示的结构。将本申请的化合物作为电子阻挡层用于制备有机电致发光器件时,能够有效的延长有机电致发光器件的寿命,并一定程度上改善发光效率或驱动电压。(The application belongs to the technical field of organic materials, and particularly relates to a nitrogen-containing compound, and an electronic element and an electronic device using the nitrogen-containing compound, wherein the organic compound has a structure shown in a formula F-1. When the compound is used as an electron blocking layer for preparing an organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency or the driving voltage can be improved to a certain extent.)

1. A nitrogen-containing compound selected from the group consisting of compounds represented by the following formulae:

wherein Ar is₃Selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

Ar₃the substituents of (a) are selected from deuterium, halogen groups, cyano, phenyl;

l is selected from a single bond, substituted or unsubstituted phenylene;

L₁selected from single bonds, substituted or unsubstituted phenylene;

L₂selected from single bonds;

Ar₁selected from substituted or unsubstitutedSubstituted or unsubstitutedSubstituted or unsubstituted

Ar₂Selected from substituted or unsubstitutedSubstituted or unsubstituted

R₅Selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

n₁represents R₅Number of (2), n₁Is 0, 1,2, 3,4 or 5;

L、L₁、Ar₁、Ar₂、R₅the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a halogenated alkyl group having 1 to 10 carbon atoms.

2. A nitrogen-containing compound selected from the group consisting of compounds represented by the following formulae:

Ar₃selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

Ar₃the substituents of (a) are selected from deuterium, halogen groups, cyano, phenyl;

l is selected from single bonds;

L₁selected from single bonds, substituted or unsubstituted phenylene;

L₂selected from single bonds;

Ar₁selected from substituted or unsubstituted

Ar₂Substituted or unsubstitutedSubstituted or unsubstituted

R₅Selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

n₁represents R₅Number of (2), n₁Is 0, 1,2, 3,4 or 5;

L、L₁、Ar₁、Ar₂、R₅the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a halogenated alkyl group having 1 to 10 carbon atoms.

3. A nitrogen-containing compound selected from the group consisting of compounds represented by the following formulae:

Ar₃selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms;

Ar₃the substituents of (a) are selected from deuterium, halogen groups, cyano, phenyl;

l is selected from single bonds;

L₁selected from substituted or unsubstitutedA substituted phenylene group;

L₂selected from single bonds;

Ar₁selected from substituted or unsubstitutedSubstituted or unsubstitutedSubstituted or unsubstitutedSubstituted or unsubstituted

Ar₂Selected from substituted or unsubstituted

R₅Selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

n₁represents R₅Number of (2), n₁Is 0, 1,2, 3,4 or 5;

L、L₁、Ar₁、Ar₂、R₅the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a halogenated alkyl group having 1 to 10 carbon atoms.

4. A nitrogen-containing compound selected from the group consisting of:

5. 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 the nitrogen-containing compound according to any one of claims 1 to 4;

preferably, the functional layer comprises an electron blocking layer comprising the nitrogen-containing compound.

6. The electronic component according to claim 5, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.

7. The electronic component according to claim 5, wherein the electronic component is an organic electroluminescent device; the organic electroluminescent device is a green device.

8. An electronic device comprising the electronic component according to any one of claims 5 to 7.

Technical Field

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

At present, the problems of reduced luminous efficiency, shortened service life and the like exist in the using process of an organic electroluminescent device, so that the performance of the organic electroluminescent device is reduced.

Disclosure of Invention

In view of the above problems in the prior art, an object of the present invention is to provide a nitrogen-containing compound that can be used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an electronic component and an electronic apparatus using the same.

In order to achieve the above object, the present application provides, in a first aspect, a nitrogen-containing compound having a structure represented by formula F-1:

wherein the content of the first and second substances,represents a chemical bond;

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

Ar₁and Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

Ar₃selected from substituted or unsubstituted aryl with 6-20 carbon atoms;

R₁、R₂、R₃and R₄Are the same or different from each other and are each independently selected from hydrogen or a group of the formula F-2, and R₁、R₂、R₃And R₄One of them is a group represented by the formula F-2;

R₅selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

n₁represents R₅Number of (2), n₁Is 0, 1,2, 3,4 or 5;

L、L₁、L₂、Ar₁、Ar₂、R₅the substituents are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group with 3-20 carbon atoms, an aryl group with 6-20 carbon atoms optionally substituted by 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl or tert-butyl, a trialkylsilyl group with 3-12 carbon atoms, a triarylsilyl group with 18-24 carbon atoms, an alkyl group with 1-10 carbon atoms, a haloalkyl group with 1-10 carbon atoms, an alkenyl group with 2-6 carbon atoms, an alkynyl group with 2-6 carbon atoms, a carbon atomCycloalkyl with the sub-number of 3-10, heterocycloalkyl with the carbon number of 2-10, cycloalkenyl with the carbon number of 5-10, heterocycloalkenyl with the carbon number of 4-10, alkoxy with the carbon number of 1-10, alkylthio with the carbon number of 1-10, aryloxy with the carbon number of 6-18, arylthio with the carbon number of 6-18 and phosphinyloxy with the carbon number of 6-18;

Ar₃the substituent(s) is selected from deuterium, a halogen group, cyano, phenyl.

In a second aspect, the present application provides an electronic component containing the nitrogen-containing compound according to the first aspect of the present application.

A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.

The nitrogen-containing compound has a molecular structure in which a carbazole derivative is used as a core and is bonded to an aromatic amine compound. The molecular structure can improve the stability and the hole transmission performance of the whole molecule through the synergistic effect of the nucleus and the surrounding hole transmission elements. The arylamine structure in the nitrogen-containing compound can improve the transmission efficiency of holes in a device, and blocks electrons in a light-emitting layer to realize the maximum recombination of carriers; the introduction of the electron-rich carbazole structure enables the structure to have a large rigid plane, and the group is relatively stable; meanwhile, by introducing an aromatic substituent group into the 4 th position of carbazole, the adjustment of material intermolecular stacking can be realized, the glass transition temperature of the compound is effectively improved, and the compound is not easy to crystallize, so that the material performance is improved. When the nitrogen-containing compound is used as an electron blocking layer for preparing an organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency or the driving voltage can be improved to a certain extent.

Drawings

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.

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

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

Description of the reference numerals

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

Detailed Description

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.

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

wherein the content of the first and second substances,represents a chemical bond;

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

Ar₁and Ar₂The aryl groups are the same or different and are respectively and independently selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms;

Ar₃selected from substituted or unsubstituted aryl with 6-20 carbon atoms;

R₁、R₂、R₃and R₄Are the same or different from each other and are each independently selected from hydrogen or a group of the formula F-2, and R₁、R₂、R₃And R₄One of them is a group represented by the formula F-2;

R₅selected from deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

n₁represents R₅Number of (2), n₁Is 0, 1,2, 3,4 or 5;

L、L₁、L₂、Ar₁、Ar₂、Ar₃、R₅the substituents of (A) are independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents independently selected from deuterium, fluorine, cyano, methyl, tert-butyl, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms and a phosphinyloxy group having 6 to 18 carbon atoms;

Ar₃the substituent(s) is selected from deuterium, a halogen group, cyano, phenyl.

In the present application, the "aryl group having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, cyano and methyl" means that the aryl group may be substituted with one or more of deuterium, fluorine, cyano and methyl, or may not be substituted with deuterium, fluorine, cyano and methyl, and when the number of substituents on the aryl group is 2 or more, the substituents may be the same or different.

Preferably, n₁Is 1.

In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. 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 R_x). For example, "substituted or unsubstituted aryl" means having a substituent R_xOr an unsubstituted aryl group. Wherein the above-mentioned substituent is R_xFor example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms optionally substituted with 0, 1,2, 3,4 or 5 substituents selected from deuterium, fluorine, cyano, methyl, tert-butyl, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a cycloalkenyl group having 5 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and an alkylthio group having 6 carbon atomsAn aryloxy group of 18, an arylthio group having 6 to 18 carbon atoms, a phosphinyloxy group having 6 to 18 carbon atoms; when two substituents R are attached to the same atom_xWhen two substituents R are present_xMay be independently present or attached to each other to form a ring with said atom; when two adjacent substituents R are present on the functional group_xWhen adjacent substituents R_xMay be present independently or may be fused to form a ring with the functional group to which it is attached.

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 L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12. For example: ar (Ar)₁Is composed ofThe number of carbon atoms is 7; l isThe number of carbon atoms is 12.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic 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 the aryl group may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10] phenanthryl, pyrenyl, benzofluoranthenyl, mesityl, and the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 13. For example, in the present application, the number of carbon atoms of the aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, 31, 32, 33, 34, 35, 36 or 40, and of course, the number of carbon atoms may be other numbers, which are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.

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

In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracenyl, phenanthrenyl, dimethylfluorenyl, biphenyl, diphenylfluorenyl, spirobifluorenyl, and the like.

In the present application, the fluorenyl group may be substituted and two substituents may be combined with each other to form a spiro structure, specific examples including, but not limited to, the following structures:

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. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The term "heteroaryl" as used herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.

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, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, N-phenylcarbazolyl, 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, specific examples of the heteroaryl group as the substituent include, but are not limited to: dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, phenanthrolinyl, and the like.

In the present application, "any two adjacent R_jIn a ring, "optionally adjacent" may include two R's on the same atom_jIt may also include two adjacent atoms each having an R_j(ii) a Wherein when there are two R on the same atom_jWhen two R are present_jMay form a saturated or unsaturated ring with the atom to which it is commonly attached; when two adjacent atoms have one R on each atom_jTwo of these R_jMay be fused to form a ring. Similarly, any two adjacent substituents forming a ring have the same explanation, and are not described in detail in this application.

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 (X), naphthyl represented by the formula (X) 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 (X-1) to the formula (X-10) comprises any possible connecting mode shown in the formula (X-1).

As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).

An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, in the following formula (Y), the substituent R group represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes shown by the formulas (Y-1) to (Y-7).

In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, and 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.

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

In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.

In the present application, specific examples of triaryl silicon groups having 18 to 24 carbon atoms include, but are not limited to: triphenylsilyl, and the like.

In the present application, specific examples of the cycloalkyl group having 3 to 20 carbon atoms include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.

Optionally, the nitrogen-containing compound is selected from compounds represented by the following chemical formula:

in one embodiment of the present application, said L, L₁And L₂The groups are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 25 carbon atoms.

Optionally, said L, L₁And L₂The groups are the same or different and are each 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 12 to 20 carbon atoms.

Optionally, said L, L₁And L₂The substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.

Specifically, the L, L₁And L₂The substituents of (a) are the same or different and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, etc.

In another embodiment of the present application, said L, L₁And L₂Are the same or different from each other and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dimethylfluorenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted diphenylene groupSubstituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted N-phenylcarbazole ylidene.

Preferably, said L, L₁And L₂The substituents of (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl.

In one embodiment of the present application, Ar is₃The aryl is selected from substituted or unsubstituted aryl with 6-12 carbon atoms.

Preferably, Ar is₃Selected from unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl.

In one embodiment of the present application, said L, L₁、L₂Each independently selected from a single bond or a substituted or unsubstituted group 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 independently selected from: deuterium, cyano, halogen group, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, anthracyl; when the number of substituents of the group W is more than 1, the substituents may be the same or different.

Optionally, said L, L₁、L₂Each independently selected from a single bond or the group consisting of:

in one embodiment of the present application, Ar₁And Ar₂The aryl groups are the same or different and are independently selected from substituted or unsubstituted aryl groups having 6 to 36 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 25 carbon atoms.

Preferably, Ar₁And Ar₂The aryl group is the same or different and is independently selected from substituted or unsubstituted aryl groups having 6 to 33 carbon atoms and substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms.

Optionally, the Ar is₁And Ar₂The substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 18 carbon atoms, and a heteroaryl group having 12 to 18 carbon atoms.

Specifically, Ar is₁And Ar₂Substituents of (a) include, but are not limited to, deuterium, fluoro, cyano, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, and the like.

In one embodiment of the present application, Ar is₁And Ar₂Each independently selected from 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 thereon, each independently selected from: deuterium, cyano, halogen group, methyl, ethyl, N-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, phenanthryl, anthracyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl; when the number of substituents of the group V is more than 1, the substituents may be the same or different.

Optionally, the Ar is₁And Ar₂Selected from the group consisting of:

in the present application, optionally, the nitrogen-containing compound is selected from the compounds as set forth in claim 4.

The synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present application illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the present application.

In a second aspect, the present invention provides an electronic component comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the nitrogen-containing compound according to the first aspect of the present invention.

The nitrogen-containing compound provided by the application has better hole transport performance and stability, can be used as an electron blocking layer material of the organic electroluminescent device, and can be used for forming at least one organic film layer in a functional layer when being used for an electronic element so as to improve the efficiency characteristic and the service life characteristic of the electronic element.

Optionally, the functional layer comprises an electron blocking layer comprising a compound provided herein. The electron blocking layer may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.

In one embodiment, the hole transport layer is adjacent to the electron blocking layer and closer to the anode than to the electron blocking layer.

Preferably, the electron blocking layer comprises a compound of the present application and the organic electroluminescent device is a green device.

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 hole transport layer 321, an electron blocking layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

In the present application, the anode 100 includes an anode material, which is preferably a material having a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); 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. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.

According to an embodiment, the hole transport layer 321 may include an inorganic doping material to improve the hole transport capability of the hole transport layer 321.

Alternatively, the hole transport layer 321 includes one or more hole transport materials, and the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited in this application. For example, the hole transport layer 321 may be composed of a compound NPB.

According to a more specific embodiment, the organic electroluminescent device is a green device and the electron blocking layer 322 contains the nitrogen-containing compound of the present application.

Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. In one embodiment, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.

The host material of the organic light emitting layer 330 may be carbazole-based derivatives, metal chelate-based compounds, bis-styryl-based derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials, which are not particularly limited in this application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be GH-n1 and GH-n 2.

The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, a metal complex, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (ppy)₃And the like.

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-01 and LiQ.

In the present application, the specific structures of EB-01, GH-n1, GH-n2, ET-01, and other compounds are shown in the following examples, and are not described herein again.

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

According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises a nitrogen-containing compound as provided herein.

According to an exemplary embodiment, as shown in fig. 3, the functional layer 300 includes an electron blocking layer 322, and the electron blocking layer 322 includes the nitrogen-containing compound of the present application. The electron blocking layer 322 may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.

According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, an electron blocking layer 322, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.

Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked.

A third aspect of the present application provides an electronic device comprising the electronic component according to 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.

In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.

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

In the following, several specific embodiments are exemplarily provided to further explain and illustrate the present application. However, the following examples are merely illustrative of the present application and do not limit the present application.

Synthesis example

Synthesis of intermediates

To a dry and nitrogen-purged round-bottom flask, 1-bromo-2-iodo-3-chlorobenzene (50.0g,157.5mmol), phenylboronic acid (19.2g,157.5mmol), tetrakis (triphenylphosphine) palladium (9.1g,7.8mmol), tetrabutylammonium bromide (2.5g,7.8mmol), potassium carbonate (65.2g,472.6mmol), toluene (400mL), ethanol (200mL), deionized water (100mL) were added, and the mixture was heated to 75 ℃ with stirring and held for 8 h; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using dichloromethane/n-heptane (1:3) as a mobile phase to obtain intermediate SM-D (35.8g, yield 85%).

To a dried nitrogen-substituted round-bottomed flask, SM-D (35.8g,133.8mmol) and tetrahydrofuran (400mL) were added, the temperature was reduced to-78 ℃ and n-butyllithium (12.8g,200.7mmol) was added dropwise, after the addition, the temperature was maintained at-78 ℃ for 30min, trimethyl borate (41.7g,401.4mmol) was added dropwise, and after the addition, the temperature was maintained at-78 ℃ for 30 min. Heating to room temperature, stirring for 12h, and adding hydrochloric acid aqueous solution to adjust the pH to be neutral. The resulting reaction was filtered to give a crude product, which was recrystallized from n-heptane (600mL) to give intermediate SM-D-1(19.6g, 63% yield).

Referring to the synthesis of intermediate SM-D, the intermediates shown in table 1 below were synthesized as reactant Q in the following table in place of phenylboronic acid:

TABLE 1

Referring to the intermediate SM-D synthesis method, the intermediates shown in table 2 below were synthesized with reactant N instead of 1-bromo-2-iodo-3-chlorobenzene and reactant M instead of phenylboronic acid:

TABLE 2

Referring to the intermediate SM-D-1 synthesis procedure, the intermediates in the following Table (reactants) were substituted for SM-D to synthesize the intermediates shown in Table 3 below:

TABLE 3

To a dry and nitrogen-purged round-bottom flask, biphenyl-2-boronic acid (51.6g,260.4mmol),2, 4-dichloronitrobenzene (50.0g,260.4mmol), tetrakis (triphenylphosphine) palladium (15.0g,13.0mmol), tetrabutylammonium bromide (4.2g,13.0mmol), potassium carbonate (107.9g,781.3mmol), toluene (400mL), ethanol (200mL), deionized water (100mL) were added, and the mixture was heated to 75 ℃ with stirring and held for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain intermediate A-1(56.5 g; yield 70%).

To a dry nitrogen-purged round-bottom flask, intermediate A-1(56.5g,182.4mmol), triphenylphosphine (119.6g,456.0mmol) and o-dichlorobenzene (400mL) were added, and the mixture was heated to 160 ℃ with stirring and reacted for 6 hours; and then, silica gel was added thereto to volatilize the liquid therein, followed by silica gel column chromatography purification using dichloromethane/n-heptane (1:3) as a mobile phase to obtain intermediate B-1(30.4g, yield 60%).

Adding an intermediate B-1(30.4g,109.5mmol), iodobenzene (22.7.0g,111.6mmol), cuprous iodide (4.2g,21.8mmol), potassium carbonate (33.3g,240.8mmol), 1, 10-phenanthroline (7.9g,43.8mmol), 18-crown ether-6 (2.9g,10.9mmol), N, N, -dimethylformamide (300mL) into a dried and nitrogen-replaced round-bottom flask, and heating to 160 ℃ under a stirring condition for 8 hours; then cooling the reaction mixture to room temperature, adding deionized water (200mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain intermediate C-1(30.9g, yield 80%).

The intermediates in Table 4 below were synthesized by following the same procedure as for the synthesis of intermediate A-1, substituting reactant A for 2, 4-dichloronitrobenzene and SM-D-X for biphenyl-2-boronic acid in the following table:

TABLE 4

Referring to the synthesis of intermediate B-1, the intermediates in table 5 below were synthesized by substituting reactant B in the following table for intermediate a-1:

TABLE 5

The intermediates in Table 6 below were synthesized by following the same procedure as for the synthesis of intermediate C-1, substituting reactant C for intermediate B-1 in the following table:

TABLE 6

To a dry and nitrogen-purged round-bottom flask, p-chlorobenzoic acid (2.19g,14.13mmol), intermediate C-1(5.0g,14.13mmol), tetrakis (triphenylphosphine) palladium (0.82g,0.70mmol), tetrabutylammonium bromide (0.23g,0.71mmol), potassium carbonate (3.90g,28.26mmol), toluene (40mL), ethanol (20mL), deionized water (10mL) were added, and the temperature was raised to 75 ℃ with stirring and held for 8 h; then cooling the reaction mixture to room temperature, adding deionized water (100mL), stirring for 15 minutes, separating an organic phase, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane (1:3) as a mobile phase to obtain intermediate D-1(4.6g, yield 75%).

Using the same procedure as for the synthesis of intermediate D-1, reactant D in the following table replaces intermediate C-1, SM-D replaces p-chlorobenzeneboronic acid, and the intermediates in table 7 below are synthesized:

TABLE 7

The intermediate C-2(10g, 14.1mmol), SM-1 (diphenylamine) (2.4g, 14.1mmol), tris (dibenzylideneacetone) dipalladium (0.1g, 0.1mmol), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.1g, 0.3mmol), sodium tert-butoxide (2.0g, 21.2mmol) and toluene solvent (100mL) were charged into a reaction flask, heated to 110 ℃ under nitrogen protection, heated to reflux and stirred for 8 h. After the reaction solution was cooled to room temperature, the reaction solution was extracted and washed with dichloromethane (50mL) and water (50mL) 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, after which the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system (1:3) to give compound 1(4.8g, yield 70%).

Referring to the synthesis of compound 1, in the following table SM-Y is substituted for SM-1 (diphenylamine), and intermediate C-X/D-X is substituted for intermediate C-1. The compounds in table 8 below were synthesized:

TABLE 8

Compound characterization

Mass spectrometry analysis of the above synthesized compounds gave the data shown in table 9 below.

TABLE 9

Compound numbering	Mass spectrum [ M + H]+	Compound numbering	Mass spectrum [ M + H]+	Compound numbering	Mass spectrum [ M + H]+
						1	487.3	2	537.3	4	563.3
7	577.3	11	593.3	74	537.3
						76	563.3	186	639.3	190	653.3
191	669.3	197	689.3	245	639.3
						246	653.3	314	653.3	378	613.3
386	669.3	443	679.3	488	639.3
						491	653.3	734	603.3	1007	719.3
1028	613.3	1161	639.3	1187	729.3
						1235	689.3	1242	715.3	1243	745.3
1244	765.3	1249	765.3	1250	714.3
						1251	837.4	1252	573.3	1253	555.2
1254	703.3	1255	729.3	1256	728.3
						1257	727.3	1258	663.3	1259	704.3
1260	667.3

The nuclear magnetic data for some of the compounds and intermediates are shown in table 10 below:

watch 10

Device embodiments

Example 1: green organic electroluminescent device

The anode was prepared by the following procedure: the thickness of ITO is set asWas 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 deposited on the hole injection layer to form a thickness ofThe hole transport layer of (1).

Compound 1 was vacuum-deposited on the hole transport layer to a thickness ofThe electron blocking layer of (1).

In electronOn the barrier layer, GH-n 1: GH-n 2: ir (ppy)₃In a ratio of 50%: 45%: 5% (evaporation rate) of vapor deposition to form a film having a thickness ofGreen organic light emitting layer (EML).

ET-06 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to formA thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness ofAnd then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness ofThe cathode of (1).

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

Example 2 example 40

In forming the electron blocking layer, an organic electroluminescent device was produced in the same manner as in example 1, except that the compound shown in table 12 was used instead of the compound 1 in example 1.

Comparative example 1

In forming the electron blocking layer, an organic electroluminescent device was produced in the same manner as in example 1, except that compound a shown in table 11 was used instead of compound 1 in example 1.

Comparative example 2

In forming the electron blocking layer, an organic electroluminescent device was produced in the same manner as in example 1, except that compound B shown in table 11 was used instead of compound 1 in example 1.

Comparative example 3

In forming the electron blocking layer, an organic electroluminescent device was produced in the same manner as in example 1, except that compound C shown in table 11 was used instead of compound 1 in example 1.

Comparative example 4

In forming the electron blocking layer, an organic electroluminescent device was produced in the same manner as in example 1, except that compound D shown in table 11 was used instead of compound 1 in example 1.

In examples 1 to 40 and comparative examples 1 to 4, the structural formula of each material used is shown in the following Table 11:

TABLE 11

For the organic electroluminescent device prepared as above, at 20mA/cm²The device performance was analyzed under the conditions shown in table 12 below:

table 12:

from the results shown in Table 12, it is understood that the driving voltage of the organic electroluminescent devices prepared by using the compounds used in the present application as the electron blocking layer was reduced by at least 0.18V, the current efficiency was improved by at least 22.7%, the external quantum efficiency was improved by at least 22.6%, and the lifetime was improved by at least 9.69% in examples 1 to 40 in which the compounds used as the electron blocking layer were compared with comparative examples 1 to 4 in which the known compounds A, B, C, and D were used.

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.