阅读说明：本技术 一种有机化合物及包含其的电子元件和电子装置 (Organic compound, electronic element containing organic compound and electronic device ) 是由 岳娜 华正伸 李应文 于 2021-05-07 设计创作，主要内容包括：本申请提供一种有机化合物及其电子元件和电子装置,属于有机电致发光技术领域。所述有机化合物的结构式由化学式1所示的结构组成,该有机化合物具有优异的光电性能,可以提高器件的发光效率和使用寿命,并能够降低工作电压。(The application provides an organic compound, an electronic element and an electronic device thereof, belonging to the technical field of organic electroluminescence. The organic compound has a structural formula shown in chemical formula 1, has excellent photoelectric properties, can improve the luminous efficiency and the service life of a device, and can reduce the working voltage.)

1. An organic compound, wherein the structural general formula of the organic compound is shown in chemical formula 1:

wherein the content of the first and second substances,represents a chemical bond of a compound represented by the formula,

R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉the same or different from each other, and each independently selected from the group consisting of a structure represented by chemical formula 2, hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms, and R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉Any one of them is selected from the structures shown in chemical formula 2; optionally, R₅And R₆The substituted or unsubstituted benzene rings are formed by mutual connection, and the substituent on the benzene rings is selected from a structure shown in a chemical formula 2, deuterium, a halogen group, a cyano group, an alkyl group with 1-10 carbon atoms, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms or a trialkylsilyl group with 3-12 carbon atoms;

L、L₁and L₂The same or different from each other, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar₁and Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl group having 6 to 40 carbon atoms, aryl group having 3 to 30 carbon atomsSubstituted or unsubstituted heteroaryl;

the L, L₁、L₂、Ar₁And Ar₂Wherein the substituents are the same or different and are each 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, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or a triphenylsilyl group; optionally, Ar₁Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring; optionally, Ar₂Any two adjacent substituents in (b) form a saturated or unsaturated 3-to 15-membered ring.

2. The organic compound of claim 1, wherein R is₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉Are the same or different from each other, and are each independently selected from the group consisting of a structure represented by chemical formula 2, hydrogen, deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group, dibenzofuranyl group, dibenzothienyl group, or trimethylsilyl group, and R is₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉Any one of them is selected from the structures shown in chemical formula 2; optionally, R₅And R₆And (b) connecting the two to form a substituted or unsubstituted benzene ring, wherein the substituent on the benzene ring is selected from the structure shown in chemical formula 2, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or trimethylsilyl.

3. The organic compound of claim 1, wherein said L, L₁And L₂The same or different, and each independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

4. The organic compound of claim 1, wherein said L, L₁And L₂The same or different from each other, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;

optionally, said L, L₁And L₂The substituents in (a) are the same or different from each other and each is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl or naphthyl.

5. The organic compound of claim 1, wherein said L, L₁And L₂Are identical or different from each other and are each independently selected from a single bond or 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, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, or naphthyl; when the number of the substituents on V is more than 1, the substituents may be the same or different.

6. The organic compound of claim 1, wherein said L, L₁And L₂Are the same or different from each other and are each independently selected from the group consisting of a single bond or the following groups:

7. the organic compound of claim 1, wherein the Ar is₁And Ar₂The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms or substituted or unsubstituted heteroaryl with 12-20 carbon atoms

Preferably, Ar is₁And Ar₂The substituent groups in the formula (I) are respectively and independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms, trimethylsilyl and triphenylsilyl; optionally, in Ar₁Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring; optionally, in Ar₂Any two adjacent substituents in (b) form a saturated or unsaturated 5-13 membered ring.

8. The organic compound of claim 1, wherein the Ar is₁And Ar₂Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;

preferably, Ar is₁And Ar₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, trimethylsilyl and triphenylsilyl; optionally, in Ar₁Any two adjacent substituents of (a) form a fluorene ring; optionally, in Ar₂Any two adjacent substituents in (a) form a fluorene ring.

9. The organic compound of claim 1, wherein the Ar is₁And Ar₂Each independently selected from 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, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, trimethylsilyl, or triphenylsilyl; when the number of substituents on W is greater than 1, the substituents may be the same or different.

10. The organic compound of claim 1, wherein the Ar is₁And Ar₂Each independently selected from the group consisting of:

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

12. an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer containing the organic compound according to any one of claims 1 to 11;

preferably, the functional layer includes a hole-adjusting layer including the organic compound.

13. The electronic component according to claim 12, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device;

preferably, the organic electroluminescent device is a red organic electroluminescent device.

14. An electronic device, characterized by comprising the electronic component of claim 12 or 13.

Technical Field

The application relates to the technical field of organic electroluminescence, in particular to an organic compound, an electronic element comprising the organic compound and an electronic device comprising the organic compound.

Background

The organic electroluminescent material is a thin film device prepared from an organic photoelectric functional material and capable of emitting light under the excitation of an electric field. At present, the OLED has been widely used in the fields of mobile phones, computers, lighting, etc. due to its advantages of high brightness, fast response, wide adaptability, etc.

The organic electroluminescent device needs different organic functional materials besides an electrode material film layer, and the semi-conducting property of the organic functional materials is due to shifted pi bonds in material molecules, wherein the shifted valence and conduction properties are formed by the pi bonds or inverted pi bond orbitals, the overlapping of the pi bonds or the inverted pi bond orbitals respectively generates a highest occupied orbital (HOMO) and a Lowest Unoccupied Molecular Orbital (LUMO), and charge transfer is generated through intermolecular transition.

In order to improve the brightness, efficiency and lifetime of organic electroluminescent devices, a multilayer structure is generally used, including: hole injection layer, hole transport layer, light emitting layer, electron transport layer, and the like. These organic layers have the function of increasing the efficiency of carrier (hole and electron) injection between the interfaces of the layers, balancing the ability of the carriers to be transported between the layers, and thus increasing the brightness and efficiency of the device.

The continuous improvement of the performance of the organic electroluminescent device requires not only the innovation of the structure and the manufacturing process of the organic electroluminescent device but also the continuous research and innovation of the organic electro-optical functional material. At present, the performance of organic electroluminescent devices is improved mainly by changing organic functional materials, and there is a need to continuously develop new materials to further improve the performance of organic electroluminescent devices, so as to obtain lower driving voltage of the devices, higher luminous efficiency of the devices and longer service life of the devices.

It is to be noted that the information disclosed in the above background section is only for enhancement of understanding of the background of the present application and therefore may include information that does not constitute prior art known to a person of ordinary skill in the art.

Disclosure of Invention

The present application aims to overcome the above-mentioned deficiencies in the prior art and provide an organic compound having a general structural formula shown in chemical formula 1:

wherein the content of the first and second substances,represents a chemical bond of a compound represented by the formula,

R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉the same or different from each other, and each independently selected from the group consisting of a structure represented by chemical formula 2, hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、 R₉Any one of them is selected from the structures shown in chemical formula 2; optionally, R₅And R₆The substituted or unsubstituted benzene rings are formed by mutual connection, and the substituent on the benzene rings is selected from a structure shown in a chemical formula 2, deuterium, a halogen group, a cyano group, an alkyl group with 1-10 carbon atoms, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms or a trialkylsilyl group with 3-12 carbon atoms;

L、L₁and L₂Are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a group having 6 to 30 carbon atomsA substituted or unsubstituted heteroarylene group of 3 to 30;

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;

the L, L₁、L₂、Ar₁And Ar₂Wherein the substituents are the same or different and are each 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, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or a triphenylsilyl group; optionally, Ar₁Any two adjacent substituents in (a) form a saturated or unsaturated 3-to 15-membered ring; optionally, Ar₂Any two adjacent substituents in (b) form a saturated or unsaturated 3-to 15-membered ring.

The fluorene derivative is adopted as a main body structure, the fluorene structure has a high triplet state energy level, and the fluorene derivative has hole transmission capacity, the triarylamine compound is connected to the fluorene derivative, so that the charge of a dispersed material is facilitated, and adamantane is directly connected to fluorene, so that the degree of freedom among molecules is increased, the coplanarity of the molecules is effectively reduced, the stacking degree among the molecules is reduced, and further, the organic compound is not easy to crystallize or aggregate during film formation, and the fluorene derivative can have a more stable amorphous state, so that the material has the advantages of low voltage, high efficiency and long service life in a device.

According to a second aspect of the present application, there is provided an electronic component comprising an anode, a cathode, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound described above.

According to a third aspect of the present application, there is provided an electronic device including the above electronic component.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.

Drawings

The accompanying drawings 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.

In the drawings:

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

Fig. 2 is a schematic structural diagram of an 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; 320. a hole transport layer; 330. a hole-adjusting layer; 340. an organic electroluminescent layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.

Detailed Description

Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.

In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.

The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application. One skilled in the relevant art will recognize, however, that the subject matter of the present application can be practiced without one or more of the specific details, or with other methods, components, materials, and so forth. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical ideas of the application.

The application provides an organic compound, the structural general formula of which is shown in chemical formula 1:

wherein the content of the first and second substances,represents a chemical bond of a compound represented by the formula,

R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉the same or different from each other, and each independently selected from the group consisting of a structure represented by chemical formula 2, hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a trialkylsilyl group having 3 to 12 carbon atoms, and R₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、 R₉Any one of them is selected from the structures shown in chemical formula 2; optionally, R₅And R₆The substituted or unsubstituted benzene rings are formed by mutual connection, and the substituent on the benzene rings is selected from a structure shown in a chemical formula 2, deuterium, a halogen group, a cyano group, an alkyl group with 1-10 carbon atoms, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms or a trialkylsilyl group with 3-12 carbon atoms;

L、L₁and L₂The same or different from each other, and each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 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;

the L, L₁、L₂、Ar₁And Ar₂Wherein the substituents are the same or different and are each 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, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or a triphenylsilyl group; optionally, Ar₁Any two adjacent substituents in (a) form a saturated or unsaturated 3-to 15-membered ring; optionally, Ar₂Any two adjacent substituents in (b) form a saturated or unsaturated 3-to 15-membered ring.

In this application, "optionally, R₅And R₆The mutual connection to form a benzene ring' means that R₅And R₆Benzene rings may or may not be formed.

In the present application, the description "… … 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 options expressed between the same symbols do not affect each other in different groups, or that the specific options 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 Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein the substituent Rc is, for 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, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or a triphenylsilyl group, and optionally, any two of the substituents are connected to each other so as to form a 3 to 15-membered saturated or unsaturated ring together with the atoms to which they are bonded. In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, the two substituents Rc may be independently present or may be attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are 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 isThe number of carbon atoms is 10; l isThe number of carbon atoms is 12.

In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, P, Si or Se or the like is included in one functional group and the remaining atoms are carbon and hydrogen.

In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms.

Preferably, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.

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 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. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,and the like. The "aryl" group herein may have 6 to 40 carbon atoms, in some embodiments, the number of carbon atoms in the aryl group may be 6 to 30, in some embodiments, the number of carbon atoms in the aryl group may be 6 to 25, in other embodiments, the number of carbon atoms in the aryl group may be 6 to 20, and in other embodiments, the number of carbon atoms in the aryl group may be 6 to 12. 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, or 30, 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, the substituted aryl group may be an aryl group in which one or two or more hydrogen atoms are substituted with a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, or 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 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 of 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, anthracyl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.

In the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, 6, or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se, and S, or derivatives 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 thiophenyl, furanyl, 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, benzofurazolyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazyl), 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 the N-aryl carbazolyl and the N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. As used herein, a "heteroaryl" group 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 20, in some embodiments the number of carbon atoms in the heteroaryl group may be from 5 to 18, in other embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 12, and in other embodiments the number of carbon atoms in the heteroaryl group may be from 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 15, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.

In this application, reference to heteroarylene means a divalent radical 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 two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trimethylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, 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: pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl.

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, trimethylsilyl group, triethylsilyl group, and the like.

The "ring" in the present application includes saturated rings, unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.

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 phenyl ring on one side, and the meaning of the dibenzofuranyl group includes any of the possible attachments as 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, the R is₁、R₂、R₃、R₄、R₅、R₆、R₇、R₈、R₉Are the same or different from each other, and are each independently selected from the group consisting of a structure represented by chemical formula 2, hydrogen, deuterium, fluorine, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group, dibenzofuranyl group, dibenzothienyl group, or trimethylsilyl group, and R is₁、R₂、R₃、 R₄、R₅、R₆、R₇、R₈、R₉Any one of them is selected from the structures shown in chemical formula 2; optionally, R₅And R₆And (b) connecting the two to form a substituted or unsubstituted benzene ring, wherein the substituent on the benzene ring is selected from the structure shown in chemical formula 2, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or trimethylsilyl.

In one embodiment of the present application, said L, L₁And L₂The same or different, and each independently selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

In one embodiment of the present application, said L, L₁And L₂The same or different from each other, and each is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;

optionally, said L, L₁And L₂The substituents in (a) are the same or different from each other and each is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl or naphthyl.

In one embodiment of the present application, said L, L₁And L₂Are identical or different from each other and are each independently selected from a single bond or 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, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, or naphthyl; when the number of the substituents on V is more than 1, the substituents may be the same or different.

In bookIn one embodiment of the 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 or the following groups:

in one embodiment of the present application, the Ar₁And Ar₂The same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms

Preferably, Ar is₁And Ar₂The substituent groups in the formula (I) are respectively and independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, aryl with 6-12 carbon atoms, heteroaryl with 3-12 carbon atoms, trimethylsilyl and triphenylsilyl; optionally, in Ar₁Any two adjacent substituents of (a) form a saturated or unsaturated 5-13 membered ring; optionally, in Ar₂Any two adjacent substituents in (b) form a saturated or unsaturated 5-13 membered ring.

In one embodiment of the present application, the Ar₁And Ar₂Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl;

preferably, Ar is₁And Ar₂Wherein the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, trimethylsilyl and triphenylsilyl; optionally, in Ar₁Any two adjacent substituents of (a) form a fluorene ring; optionally, in Ar₂Any two adjacent substituents in (a) form a fluorene ring.

In one embodiment of the present application, aAr is described₁And Ar₂Each independently selected from 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, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, carbazolyl, trimethylsilyl or trisphenylsilyl; when the number of substituents on W is greater than 1, the substituents may be the same or different.

In one embodiment of the present application, the Ar₁And Ar₂Each independently selected from the group consisting of:

alternatively, the organic compound is selected from the group formed by, but not limited to:

the application also provides an electronic component for realizing photoelectric conversion or electro-optical conversion. The electronic component includes an anode and a cathode disposed opposite to each other, and at least one functional layer interposed between the anode and the cathode, the functional layer containing an organic compound of the present application.

Optionally, the functional layer comprises a hole-adjusting layer comprising the organic compound.

Optionally, the electronic element described herein is an organic electroluminescent device or a photoelectric conversion device, and further optionally, the organic electroluminescent device is a red organic electroluminescent device.

In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, where the functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a hole adjustment layer 330, an organic electroluminescent layer 340, an electron transport layer 350, and an electron injection layer 360; a hole injection layer 310, a hole transport layer 320, a hole adjusting layer 330, an organic electroluminescent layer 340, an electron transport layer 350, and an electron injection layer 360 may be sequentially formed on the anode 100. The hole adjusting layer 330 may contain an organic compound as described herein.

Optionally, the anode 100 comprises an anode material, which is 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 [3,4-9 (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 320 may include one or more hole transport materials, and the hole transport materials may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not specifically limited herein. By way of example, in one embodiment of the present application, the hole transport layer 320 is composed of the compound NPB.

Alternatively, the hole adjusting layer 330 is composed of an organic compound provided herein. The fluorene derivative is adopted as a main body structure, the fluorene structure has a high triplet state energy level, and has the capacity of hole transmission and electron transmission, wherein condensed rings are formed on the fluorene structure, so that a large rigid plane can be formed, the stability of the material is improved, meanwhile, the triarylamine compound is connected on the fluorene derivative, the charge of a dispersed material is facilitated, the coplanarity of molecules is reduced, the product is easier to form a film, the molecular weight of the product is increased, the glass transition temperature of the product is improved, the product is difficult to crystallize, and meanwhile, functional groups such as dibenzofuran, spirobifluorene and dibenzothiophene are introduced on aromatic amine. The conductivity of the material can be effectively enhanced, and the generation and the transmission of holes are more facilitated.

The organic electroluminescent layer 340 may be composed of a single light emitting material, or may include a host material and a guest material. Alternatively, the organic electroluminescent layer 340 may be composed of a host material and a guest material, and holes and electrons injected into the organic light emitting layer 340 may be combined in the organic light emitting layer 340 to form excitons, which transfer energy to the host material and transfer energy to the guest material, so that the guest material can emit light.

The host material of the organic electroluminescent layer 340 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 this application. In one embodiment of the present application, the host material of the organic electroluminescent layer 340 may be CBP.

The guest material of the organic electroluminescent layer 340 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 this application. For example, in one embodiment of the present application, the guest material of the organic light emitting layer 340 may be Ir (piq)₂(acac)。

The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. From the perspective of molecular design, the compound forms an electron-deficient large conjugated plane structure, has the advantages of asymmetric structure and larger steric hindrance, and can reduce intermolecular cohesion and reduce crystallization tendency, thereby improving electron transmission rate. In one embodiment of the present application, the electron transport layer 350 may be composed of ET-06 and LiQ.

Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multi-layer materials such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂and/Ca, but not limited thereto. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.

Optionally, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. 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. In one embodiment of the present application, the hole injection layer 310 may be composed of F4-TCNQ.

Optionally, an electron injection layer 360 may be further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include 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. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).

The application also provides an electronic device, which comprises the electronic element.

For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, and the first electronic device 400 includes any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device. The electronic device may be 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. Since the first electronic device 400 has the organic electroluminescent device, the same advantages are obtained, and the description of the present application is omitted.

The present application will be described in detail below with reference to examples, but the following description is intended to explain the present application, and not to limit the scope of the present application in any way.

Synthetic examples

One skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare a number of other compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully accomplished by those skilled in the art by modification, such as appropriate protection of interfering groups, by the use of other known reagents other than those described herein, or by some routine modification of reaction conditions.

In the synthesis examples described below, all temperatures are in degrees celsius unless otherwise stated. Some of the reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company and Alfa Chemical Company, and some of the intermediates that could not be purchased directly were prepared by simple reaction of commercially available starting materials and were used without further purification unless otherwise stated. The other conventional reagents were purchased from Shantou Wen Long chemical reagent factory, Guangdong Guanghua chemical reagent factory, Guangzhou chemical reagent factory, Tianjin Haojian Yunyu chemical Co., Ltd, Tianjin Shucheng chemical reagent factory, Wuhan Xin Huayuan science and technology development Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, and Qingdao Kaolingyi factory. The anhydrous solvent such as anhydrous tetrahydrofuran, dioxane, toluene, diethyl ether, etc. is obtained by refluxing and drying the metal sodium. The reactions in the various synthesis examples were generally carried out under a positive pressure of nitrogen or argon, or by placing a drying tube over an anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask was closed with a suitable rubber stopper, and the substrate was injected into the reaction flask via a syringe. The individual glassware used was dried.

During purification, the chromatographic column is a silica gel column, and the silica gel (100-200 meshes) is purchased from Qingdao oceanic plants.

In each synthesis example, the conditions for measuring low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage rod HPLC-M (column model: Zorbax SB-C18, 2.1X 30mm, 3.5 μ M, 6min, flow rate 0.6 mL/min. mobile phase: 5% -95% (acetonitrile containing 0.1% formic acid) in (water containing 0.1% formic acid) ratio, using electrospray ionization (ESI), at 210nm/254nm, with UV detection.

Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CDCl at room temperature₃As solvent (in ppm) with TMS (0ppm)As a reference standard. When multiple peaks occur, the following abbreviations will be used: s (singleton), d (doublet), t (triplet), m (multiplet).

The target compounds were detected by UV at 210nm/254nm using Agilent 1260pre-HPLC or Calesep pump 250pre-HPLC (column model: NOVASEP 50/80mm DAC).

Preparation example 1: synthesis of Compound 1

1. Synthesis of intermediate SA 2-1

A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb-shaped condenser was purged with nitrogen (0.100L/min) for 15min, and then reactants SA 1-1(16.0g, 88.79mmol), tetradecyltrimethylammonium chloride (3.89g, 13.32mmol) and an aqueous solution of ammonium bromide (30 wt%, 21.75g, 221.9mmol) were added thereto. Stirring and heating to 75 ℃, adding potassium bromate (16.31g, 97.67mmol), keeping the temperature for reaction for 3h, and cooling to room temperature after the reaction is finished. 20% aqueous sodium sulfite solution was added, and after filtration, the cake was washed with water and dried, the intermediate SA 2-1 was obtained as a yellow solid (20.0g, yield 87%).

Referring to the synthesis method of intermediate SA 2-1, intermediates shown in Table 1 below were synthesized, wherein reactants SA 1-X (X is 2) were substituted for reactants SA 1-1, and intermediates SA 2-X (X is 2) shown in Table 1 below were synthesized.

TABLE 1

2. Synthesis of intermediate SA4-1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a dropping funnel for replacement for 15min, adding an intermediate SA 2-1(19.7g, 76.03mmol) and tetrahydrofuran (125mL), starting stirring, uniformly stirring, reducing the temperature of the system to-78 ℃ by using liquid nitrogen, dropping n-butyl lithium (7.30g, 114.05mmol) after the temperature is stabilized, preserving the temperature for 1h at-78 ℃ after dropping, diluting a reactant SA 3-1(16.40g, 76.03mmol) by using tetrahydrofuran (33mL) (the ratio is 1: 2), dropping into the system, preserving the temperature for 1h at-78 ℃ after dropping, naturally heating to 25 ℃ and stirring for 12 h. After completion of the reaction, the reaction mixture was poured into water (200mL), stirred for 10min, and then dichloromethane (250mL) was added to conduct extraction 2 times, the organic phases were combined, dried over anhydrous magnesium sulfate, and passed through a silica gel funnel (1: 2), and then the filtrate was evaporated to dryness to obtain intermediate SA4-1 (19.2g, yield 63.8%).

Referring to the synthesis of intermediate SA4-1, intermediates shown in Table 2 below were synthesized, wherein reactant SAY-X (X is 1-2 or 4-6, Y is 1 or 2) or intermediate SAY-X (X is 2, Y is 2) was substituted for intermediate SA 2-1, and intermediate SA 4-X (X is 2-7) shown in Table 2 below was synthesized.

TABLE 2

3. Synthesis of intermediate A1-2

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser for replacement for 15min, adding intermediate SA 4-2(24.6g, 77.74mmol), bromine (13.68g, 85.51mmol), tetrakis (triphenylphosphine) palladium (0.90g, 0.78mmol), potassium carbonate (16.09g, 116.61mmol), 2-dichloro-1, 3-cyclohexyl-4, 5-imidazolidinedione (28.47g, 85.51mmol) and THF (123mL), heating to reflux, and stirring for reaction for 6 h; after the reaction is finished, cooling to room temperature, adding DCM (1000mL) for extraction, collecting an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by column chromatography on silica gel followed by recrystallization from dichloromethane/n-heptane to yield intermediate A1-2 as a white solid (19.46g, 66% yield).

Referring to the synthesis of intermediate A1-2, the intermediates shown in Table 3 below were synthesized, wherein reactant SA 4-X (X is 1 or 3-7) was substituted for intermediate SA 4-2, to synthesize intermediate A1-X (X is 1 or 3-7) shown in Table 3 below.

TABLE 3

4. Synthesis of intermediate A2-1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser for replacement for 15min, adding intermediate A1-1(19.0g, 48.06mmol), reactant SA 5-1(6.44g, 52.87mmol), tetrakis (triphenylphosphine) palladium (0.55g, 0.48mmol), potassium carbonate (9.95g, 72.09mmol), 2-dichloro-1, 3-cyclohexyl-4, 5-imidazolidinedione (16.02g, 48.06mmol) and THF (95mL), heating to reflux, and stirring for reaction for 6 h; after the reaction is finished, cooling to room temperature, adding DCM (1000mL) for extraction, collecting an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by column chromatography on silica gel followed by recrystallization from dichloromethane/n-heptane to yield intermediate A2-1 as a white solid (14.67g, 67% yield).

Referring to the synthesis of intermediate A2-1, the intermediates shown in Table 4 below were synthesized, wherein intermediate A1-X (X is 4-7) was substituted for intermediate A1-1, SA 5-1 or SA 5-2 was substituted for SA-5-1 to synthesize intermediate A2-X (X is 4-10) shown in Table 4 below.

TABLE 4

5. Synthesis of intermediate A3-1

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then added with intermediate A2-1 (14.5g, 31.84mmol), pinacol diboron diborate (8.09g, 31.84mmol) (reactant SA 6-1), tris (dibenzylideneacetone) dipalladium (0.29g, 0.32mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.3g, 0.67mmol), potassium acetate (4.69g, 47.76mmol) and 1, 4-dioxane (87mL), heated to 80 ℃ and stirred for 3.5h, and after completion of the reaction, cooled to room temperature. Extracting reaction liquid, collecting an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by recrystallization from toluene to give intermediate A3-1 as a solid (12.5g, yield 78.2%).

Referring to the synthesis method of intermediate A3-1, intermediates shown in Table 5 below were synthesized, wherein intermediates 1-X (X is 2 or 3) or intermediates A2-X (X is 4 to 9) were substituted for intermediate A2-1, and intermediates A3-X (X is 2 to 9) shown in Table 5 below were synthesized.

TABLE 5

6. Synthesis of intermediate A4-1

A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then intermediate A3-1 (11.90g, 23.68mmol), reactant SA 7-1(5.66g, 23.68mmol), potassium carbonate (4.90g, 35.52mmol), tetrakis (triphenylphosphine) palladium (0.27g, 0.24mmol), tetrabutylammonium bromide (0.13g, 0.47mmol) and a mixed solvent of THF (72mL) and water (24mL) were added. Stirring is started, reflux reaction is carried out for 7 hours, and after the reaction is finished, the reaction is cooled to room temperature. The organic phases were separated by extraction with DCM (800mL), the organic phases were combined, the organic phases were dried over anhydrous magnesium sulphate, the filtrate was filtered and the solvent was distilled off under reduced pressure, the crude product was purified by column chromatography on silica gel using n-heptane as the mobile phase, followed by purification by recrystallization using dichloromethane/n-heptane system to give intermediate a4-1 as a white solid (7.5g, 65% yield).

Referring to the synthesis of intermediate A4-1, intermediates shown in Table 6 below were synthesized, wherein intermediate A3-X (X: 2-9) was substituted for intermediate A3-1 and reactant SA 7-X (X: 2-11) was substituted for reactant SA 7-1, to synthesize intermediates A4-X (X: 2-15) shown in Table 6 below.

TABLE 6

7. Synthesis of intermediate A5-1

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then added with intermediate A2-1 (7.50g, 16.47mmol), 4-aminobiphenyl (2.79g, 16.47mmol) (reactant SA 8-1), toluene solvent (75mL), sodium tert-butoxide (2.37g, 24.70mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.16g, 0.3293mmol) and tris (dibenzylideneacetone) dipalladium (0.16g, 0.1647mmol), heated to 108 ℃ and stirred for 1h to stop the reaction, and the reaction mixture was cooled to room temperature. Extracting and separating an organic phase by using toluene, washing the organic phase to be neutral by using water, drying the organic phase by using anhydrous magnesium sulfate, filtering, and then distilling and concentrating the filtrate under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to yield intermediate A5-1 as a white solid (7.08g, 82% yield).

Referring to the synthesis of intermediate A5-1, intermediates shown in Table 7 below were synthesized, wherein intermediate A1-X (X is 2-3), intermediate A2-X (X is 4-10), or intermediate A4-X (X is 2-15) or instead of intermediate A2-1, reactant SA 8-X (X is 1-22) instead of reactant SA 8-1, and intermediate A5-X (X is 2-33) shown in Table 7 below was synthesized.

TABLE 7

8. Synthesis of Compound 262

A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, and then, intermediate A5-1 (6.7g, 12.32mmol), 4-bromobiphenyl (2.87g, 12.32mmol) (reactant SA 9-1), toluene solvent (67mL), sodium tert-butoxide (1.78g, 18.48mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.10g, 0.2464mmol) and tris (dibenzylideneacetone) dipalladium (0.11g, 0.1232mmol) were added thereto, followed by heating to 108 ℃ and stirring for 2h to stop the reaction, and the reaction mixture was cooled to room temperature. Extracting and separating an organic phase by using toluene, washing the organic phase to be neutral by using water, drying the organic phase by using anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by recrystallization from toluene system to obtain compound 262 as a white solid (5.24g, yield 61.1%), ms spectrum (m/z): 696.4[ M + H ] +.

Referring to the synthesis of compound 262, except that intermediate A5-X (X is 2 to 28) was used instead of intermediate A5-1 and reactant SA 9-X (X is 1 to 21) was used instead of reactant SA 9-1, the compounds shown in Table 8 below were synthesized.

TABLE 8

Part of the compound NMR data are shown in Table 9 below

TABLE 9

Preparation and performance evaluation of organic electroluminescent device

Example 1

Red organic electroluminescent device

Will have a thickness ofThe anode 100ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and prepared into an experimental substrate having a cathode 200, an anode 100 and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O₂:N₂The plasma is used for surface treatment to increase the work function of the anode 100 (experimental substrate), and an organic solvent is used for cleaning the surface of the ITO substrate to remove scum and oil stains on the surface of the ITO substrate.

A compound F4-TCNQ (structural formula shown below) was vacuum evaporated onto an experimental substrate to a thickness ofHole injection layer 310 (HIL); and a compound NPB (structural formula is shown below) is vacuum-evaporated over the hole injection layer 310 to form a film having a thickness ofHole transport layer 320 (HTL).

A compound 262 is vacuum evaporated on the hole transport layer 320(HTL) to a thickness ofThe hole adjusting layer 330.

On the hole-adjusting layer 330, CBP (structural formula shown below) and Ir (piq)₂(acac) (structural formula below) in 97%: 3% of the total amount of the components are co-evaporated to form a film with a thickness ofRed light emitting layer 340 (R-EML).

ET-06 and LiQ are mixed according to the weight ratio of 1:1 and formed by evaporationA thick electron transport layer 350(ETL), followed by evaporation of Yb onto the electron transport layer to a thickness ofElectron injection layer 360 (EIL).

Magnesium (Mg) and silver (Ag) were deposited on the electron injection layer by vacuum deposition at a film thickness ratio of 1:9 to form a layer having a thickness ofThe cathode 200.

Further, a protective layer is deposited on the cathode 200 to a thickness ofForming a capping layer (CPL), thereby completing the fabrication of the organic light emitting device.

Wherein F4-TCNQ, NPB, Ir (piq)₂(acac), CBP, ET-06, LiQ, CP-05, Compound A, Compound B, Compound C have the structural formulas shown in Table 10 below:

watch 10

Examples 2 to 33

A red organic electroluminescent device was produced in the same manner as in example 1, except that in forming the hole-adjusting layer, the compounds shown in table 11 were used instead of the compound 262.

Comparative example 1

A red organic electroluminescent device was produced in the same manner as in example 1, using compound a instead of compound 262.

Comparative example 2

A red organic electroluminescent device was produced in the same manner as in example 1, using compound B instead of compound 262.

For the organic electroluminescent device prepared as above, IVL data was at 10mA/cm²The life was 20mA/cm²The results of the test at the current density are shown in Table 11.

TABLE 11 Performance test results of red organic electroluminescent devices

From the results in Table 11, it is understood that the OLED devices having the compound as the organic electroluminescent layer have improved properties in the organic electroluminescent devices prepared in examples 1 to 33 as compared with the comparative examples. Among them, examples 1 to 33 of the compound as the hole-adjusting layer reduced the driving voltage of the organic electroluminescent device by at least 9.7%, improved the current efficiency (Cd/a) by at least 13.4%, improved the power efficiency (lm/W) by at least 12.1%, improved the external quantum efficiency by at least 14%, improved the lifetime by at least 9%, and improved the maximum lifetime by 68 hours, as compared with comparative examples 1 to 2 of the device corresponding to the compound in the prior art. From the above data, it is clear that the use of the organic compound of the present application as an electron blocking layer of an electronic device significantly improves both the luminous efficiency (Cd/a) and the lifetime (T95) of the electronic device.

The foregoing variations and modifications are within the scope of the present application. It should be understood that the present application as disclosed and defined in this specification extends to all alternative combinations of two or more of the individual features mentioned or evident from the text and/or drawings. All of these different combinations constitute a number of alternative aspects of the present application. The embodiments described in this specification illustrate the best mode known for carrying out the application and will enable those skilled in the art to make and use the application.