阅读说明：本技术 有机化合物及包含其的电子元件和电子装置 (Organic compound, and electronic element and electronic device comprising same ) 是由 岳娜 李昕轩 李应文 于 2021-09-29 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。本申请的化合物包含甲基茚和芳胺基团,能有效提高材料的热稳定性、成膜性能、载流子迁移率。本申请化合物应用于有机电致发光器件可以提高器件的发光效率和寿命。(The application provides an organic compound, an electronic element and an electronic device thereof, belonging to the technical field of organic electroluminescence. The compound contains methyl indene and arylamine groups, and can effectively improve the thermal stability, film-forming property and carrier mobility of the material. The application of the compound in an organic electroluminescent device can improve the luminous efficiency and the service life of the device.)

1. An organic compound, characterized in that the organic compound has a structure as shown in formula 1:

L、L₁、L₂the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar₁、Ar₂are the same or different and are each independently selected from C6-33, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

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, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms; optionally, Ar₁、Ar₂Wherein any two adjacent substituents form a substituted or unsubstituted 5-15 membered ring, and the substituents of the 5-15 membered ring are selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a haloalkyl group having 1 to 6 carbon atoms;

R₁、R₂the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂The number of (2); n is₁Selected from 0, 1,2, 3 or 4, n₁When greater than 1, any two R₁The same or different; n is₂Selected from 0, 1,2 or 3, n₂When greater than 1, any two R₂The same or different.

2. The organic compound of claim 1, wherein said L₁、L₂L are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atoms;

alternatively, L₁、L₂The substituents in L are the same or different and are independently selected from deuterium, halogen group, cyano, trimethylsilyl group and alkyl with 1-4 carbon atomsA halogenated alkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group or a pyridyl group.

3. The organic compound of claim 1, wherein said L₁、L₂And L are each independently selected from 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 phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridinylene group, or a subunit group formed by connecting two or three of the foregoing subunits by a single bond;

optionally, said L₁、L₂And the substituents in L are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, or pyridyl.

4. The organic compound of claim 1, wherein said L₁、L₂And L are each independently selected from the group consisting of a single bond or the following groups:

5. the organic compound of claim 1, wherein the Ar is₁And Ar₂The same or different, and are respectively and independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms or substituted or unsubstituted heteroaryl with 5-18 carbon atoms;

optionallyAr is said₁And Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and a deuterated alkyl group having 1 to 4 carbon atoms; optionally, Ar₁And Ar₂Any two adjacent substituents form a substituted or unsubstituted 5-13 membered saturated or unsaturated ring, and the substituents of the 5-13 membered saturated or unsaturated ring are selected from alkyl groups having 1 to 4 carbon atoms.

6. 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 terphenyl, 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 pyridyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorene ]]Substituted or unsubstituted spiro [ cyclohexane-1, 9' -fluorene]Substituted or unsubstituted spiro [ adamantane-1, 9' -fluorene]A group;

optionally, the Ar is₁And Ar₂Wherein the substituents are each independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, or pyridyl.

7. 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, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, or pyridyl; when the number of substituents on W is greater than 1, the substituents may be the same or different.

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

9. the organic compound of claim 1, wherein R is₁And R₂Each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, or pyridyl.

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

11. an electronic component comprising an anode, a cathode, and a functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound according to any one of claims 1 to 10.

12. The electronic element according to claim 11, wherein the electronic element is selected from an organic electroluminescent device or a photoelectric conversion device;

optionally, the functional layer comprises a hole transport layer comprising the organic compound;

optionally, the organic electroluminescent device is a red organic electroluminescent device or a green organic electroluminescent device.

13. The electronic component of claim 12, wherein the electronic component is selected from organic electroluminescent devices, wherein the hole transport layer comprises a first hole transport layer and a second hole transport layer in a stacked arrangement, and wherein the first hole transport layer is closer to the anode than the second hole transport layer, and wherein the second hole transport layer comprises the organic compound.

14. An electronic device, characterized in that it comprises an electronic component according to any one of claims 11-13.

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

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 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. The organic electroluminescent device needs different organic functional materials besides an electrode material film layer, and the semiconducting property of the organic functional materials is that shifted pi bonds in material molecules, and pi bond or inverted pi bond orbitals form shifted atomic valence and conduction performance, and the overlapping of the pi bonds or the inverted pi bond orbitals respectively generates highest occupied orbitals (HOMO) and Lowest Unoccupied Molecular Orbitals (LUMO), so that charge transmission is generated through intermolecular hopping.

In the structure of the organic light-emitting device, the electron blocking layer is used for blocking electrons transmitted by the organic light-emitting layer, so that the electrons and holes can be effectively compounded in the organic light-emitting layer; meanwhile, the electron blocking layer can also block excitons diffused from the organic light emitting layer, so that triplet state quenching of the excitons is reduced, and the light emitting efficiency of the organic electroluminescent device is further ensured. The compound of the electron blocking layer has a relatively high LUMO value, which can effectively block the transport and diffusion of electrons and excitons from the organic light emitting layer toward the anode.

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 an organic electroluminescent device is improved by changing an organic functional material, and the capabilities of reducing the driving voltage of the device, improving the luminous efficiency of the device and prolonging the service life of the device are required.

Content of application

An object of the present application is to overcome the above-mentioned disadvantages of the prior art, and to provide an organic compound, wherein the organic compound has a structure shown in chemical formula 1:

L、L₁、L₂the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar₁、Ar₂the same or different, and each is independently selected from substituted or unsubstituted aryl with 6-33 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

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, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms; optionally, Ar₁、Ar₂Any two adjacent substituents form a substituted or unsubstituted 5-15 membered ring, and the substituents of the 5-15 membered ring are selected from alkyl with 1-6 carbon atoms and haloalkyl with 1-6 carbon atoms;

R₁、R₂the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₁Selected from 0, 1,2, 3 or 4, n₁When greater than 1, any two R₁The same or different; n is₂Selected from 0, 1,2 or 3, n₂When greater than 1, any two R₂The same or different.

Two indene groups in the compound are fused in the same direction to form a larger rigid plane, so that the thermal stability and the membrane stability of the material can be effectively improved, meanwhile, a methyl indene structure has stable carrier mobility, and meanwhile, an aromatic amine group is connected to one side of a fused ring, so that the charge of the material can be dispersed, the coplanarity of molecules can be reduced, the HOMO energy level of the compound can be adjusted, and the hole transmission can be facilitated. Tetramethyl on the condensed ring is substituted, so that the stereo characteristic of a parent nucleus is improved, intermolecular pi-pi stacking can be effectively reduced, the product is not easy to crystallize and is easier to form a film, the thermal stability of the material is improved, the molecular agglomeration is reduced, and the material has the advantages of low voltage and high efficiency in devices. The invention provides a second hole transport layer material with high mobility, which can be applied to an organic electroluminescent device, and the compound can effectively reduce the driving voltage, improve the photoelectric conversion efficiency of the device and prolong the service life of the device.

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

Further, the functional layer includes a hole transport layer including the organic compound.

Further, the electronic element is an organic electroluminescent device or a photoelectric conversion device.

Further, the hole transport layer includes a first hole transport layer and a second hole transport layer which are stacked, and the first hole transport layer is closer to the anode than the second hole transport layer, and the second hole transport layer includes the organic compound.

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 above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached 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 some embodiments of the present application.

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

The reference numerals of the main elements in the figures are explained as follows:

100. an anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport 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

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 present application provides an organic compound, wherein the organic compound has a structure as shown in chemical formula 1:

L、L₁、L₂are the same or different and are each independently selected from the group consisting of single bondsA substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

Ar₁、Ar₂the same or different, and each is independently selected from substituted or unsubstituted aryl with 6-33 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

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, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms; optionally, Ar₁、Ar₂Wherein any two adjacent substituents form a substituted or unsubstituted 5-15 membered ring, and the substituents of the 5-15 membered ring are selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and a haloalkyl group having 1 to 6 carbon atoms;

R₁、R₂the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;

n₁represents R₁Number of (2), n₂Represents R₂Number of (2), n₁Selected from 0, 1,2, 3 or 4, n₁When greater than 1, any two R₁The same or different; n is₂Selected from 0, 1,2 or 3, n₂When greater than 1, any two R₂The same or different.

In some embodiments, the R is₁、R₂Each independently selected from hydrogen, deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pyridyl, carbazolyl, dibenzofuranylDibenzothienyl, dimethylfluorenyl.

In some embodiments, n is₁Is 0, n₂Is 0.

In the present application, the description "independently selected" and "independently selected" are used interchangeably and should be understood in a broad sense, which means that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other. For example,') "Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, 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 Rc as the substituent may be, for example, deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms. 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, these two substituents Rc may be independently present or 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 the group consisting of substituted C12 arylene, then all of the C12 arylene groups and substituents thereon are 12 and L isThe number of carbon atoms is 12.

In the present application, "alkyl" may include straight chain alkyl groups, branched chain alkyl groups. The alkyl group may have a specified number of carbon atoms, for example, an alkyl group having 1 to 10 carbon atoms. In the present application, numerical ranges such as "1 to 10" when used to define the number of carbon atoms, refer to each integer in the given range, including alkyl groups having 1,2, 3,4, 5, 6, 7, 8, 9, or 10 carbon atoms; for example, "an alkyl group having 1 to 5 carbon atoms" means an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH)₃) Ethyl group (Et, -CH)₂CH₃) N-propyl (n-Pr, -CH)₂CH₂CH₃) Isopropyl group (i-Pr, -CH (CH)₃)₂) N-butyl (n-Bu, -CH)₂CH₂CH₂CH₃) Isobutyl (i-Bu, -CH)₂CH(CH₃)₂) Sec-butyl (s-Bu, -CH (CH)₃)CH₂CH₃) Tert-butyl (t-Bu, -C (CH)₃)₃) Pentyl, etc.

In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3 to 10 carbon atoms, and numerical ranges such as "3 to 10" refer to each integer in the given range, including cycloalkyl groups having 3,4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples of cycloalkyl groups include, but are not limited to, for example, cyclohexyl, cyclopentyl, or adamantyl.

In this application, aryl refers to derivativesOptional functional groups or substituents from aromatic carbocyclic rings. 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. 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.

In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25, 30 or 33. In some embodiments, a substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 33 carbon atoms, in other embodiments a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, in other embodiments a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, and in other embodiments a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.

In this application, as L₁、L₂、L、Ar₁、Ar₂Aryl groups of substituents of (1) such as, but not limited to, phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl.

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 a group in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, or 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, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure, and specific examples include, but are not limited to, the following structures:

in the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, or 6 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. Illustratively, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto.

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

In this application, as L₁、L₂、L、Ar₁、Ar₂Examples of heteroaryl groups as substituents of (a) are, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl.

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, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.

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

"ring" in this application includes saturated rings (i.e., aliphatic rings), unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl, unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl. In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 5-15 membered ring in this application is for example but not limited to: cyclopentane, cyclohexane, benzene ring, indene ring, adamantane, fluorene ring, 9H-xanthene ring, naphthalene ring, etc. A5-to 10-membered ring refers to a ring system formed from 5-10 ring atoms. For example, the fluorene ring belongs to the 13-membered ring, cyclohexane belongs to the 6-membered ring, and adamantane belongs to the 10-membered ring.

In this application, 5-10 membered aliphatic rings such as, but not limited to, cyclopentane, cyclohexane, adamantane.

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.

As used herein, an delocalized linkage refers to a single bond extending from a ring systemIt means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule. For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).

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

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

In some embodiments of the present application, the L₁、L₂L are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 12 carbon atomsAnd (4) an aryl group.

Alternatively, L₁、L₂And the substituents in L are the same or different and are each independently selected from deuterium, a halogen group, cyano, trimethylsilyl, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, phenyl, naphthyl or pyridyl.

In some embodiments of the present application, the L₁、L₂And L is each independently selected from 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 phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridinylene group, or a subunit group formed by connecting two or three of the foregoing subunits by a single bond.

Optionally, said L₁、L₂And the substituents in L are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, or pyridyl.

In some embodiments, the L is₁、L₂Each 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, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, or pyridyl; when the number of the substituents of V is largeIn 1, each substituent is the same or different.

In the present application, a plurality means 2 or more.

Optionally, said L₁、L₂And L are each independently selected from the group consisting of a single bond or the following groups:

in some embodiments, L is a single bond. The compound in which L is a single bond has a shallower HOMO level, and is more suitable as a hole assist layer (electron blocking layer) of a red organic electroluminescent device.

In some embodiments, L is selected from the group consisting of:

in some embodiments, L is selected from a single bond or the group consisting of:

in some embodiments of the present application, the Ar is₁And 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 5 to 18 carbon atoms.

Optionally, the Ar is₁And Ar₂Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and a deuterated alkyl group having 1 to 4 carbon atoms; optionally, Ar₁And Ar₂Wherein any two adjacent substituents form a substituted or unsubstituted 5-13 membered saturated or unsaturated ringAnd the substituent of the 5-13 membered saturated or unsaturated ring is selected from alkyl with 1-4 carbon atoms.

In some embodiments of the present application, the Ar is₁And Ar₂Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, 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 pyridyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted spiro [ cyclopentane-1, 9' -fluorene ]]Substituted or unsubstituted spiro [ cyclohexane-1, 9' -fluorene]Substituted or unsubstituted spiro [ adamantane-1, 9' -fluorene]And (4) a base.

Optionally, the Ar is₁And Ar₂Wherein the substituents are each independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, or pyridyl.

Optionally, the Ar is₁And Ar₂Each independently selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group W has one or more substituents thereon, each independently selected from: deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl, carbazolyl, or pyridyl; when the number of substituents on W is more than1, each substituent is the same or different.

Further optionally, the Ar₁And Ar₂Each independently selected from the group consisting of:

in some embodiments of the present application, the R is₁And R₂Each independently selected from deuterium, cyano, fluoro, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, or pyridyl.

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 which are oppositely disposed, and a functional layer interposed between the anode and the cathode, the functional layer containing the organic compound of the present application.

The compounds provided herein can be used to form at least one organic film layer in a functional layer to improve voltage characteristics, efficiency characteristics, or lifetime characteristics of an electronic component.

Optionally, the functional layer comprises a hole transport layer comprising said organic compound in order to improve the transport of holes between the anode and the energy conversion layer.

The electronic element of the present application may be an organic electroluminescent device or a photoelectric conversion device. For an organic electroluminescent device, its functional layers may include an organic light-emitting layer as an energy conversion layer; for a photoelectric conversion device, the functional layer may include a photoelectric conversion layer as an energy conversion layer.

According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be, for example, a red organic electroluminescent device, a blue organic electroluminescent device, a green organic electroluminescent device, a yellow organic electroluminescent device, a white organic electroluminescent device, or an organic electroluminescent device of other colors.

As shown in fig. 1, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound as provided herein.

Alternatively, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 is disposed between the organic light emitting layer 330 and the anode 100. Hole transport layer 320 can include compounds of the present application.

In a specific embodiment, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 (also referred to as a hole adjusting layer or an electron blocking layer) stacked in sequence, wherein the first hole transport layer 321 is closer to the anode 100 than the second hole transport layer 322. Optionally, the second hole transport layer comprises an organic compound of the present application.

In the present application, the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, and specifically may be selected from the compounds shown below, or any combination thereof.

In one embodiment, the first hole transport layer material can be TAPC (i.e., HT-7), and the second hole transport layer 322 can be comprised of the compounds provided herein.

On one hand, the compound provided by the application has high hole transport efficiency, and can improve the hole transport efficiency of the hole transport layer 320; on the other hand, the organic compound provided by the application avoids forming a plurality of triarylamine structures, and further avoids the situation that the LUMO energy level of the organic compound is too shallow, which can improve the energy level difference between the second hole transport layer 322 and the organic light emitting layer 330, so that the second hole transport layer 322 can realize a certain electron blocking effect, and the service life of the organic electroluminescent device is prolonged. On the other hand, the organic compound provided by the present application can have a suitable HOMO level, so that the HOMO levels between the second hole transport layer 322 and the first hole transport layer 321 are both small, and thus, the injection efficiency of the first hole transport layer 321 can be improved, and the driving voltage of the organic electroluminescent device can be reduced.

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. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light. The guest material is also referred to as a dopant material or dopant. They can be classified into fluorescent dopants and phosphorescent dopants according to the type of light emission. The dopant may be selected from a red phosphorescent dopant, a green phosphorescent dopant, or a blue dopant. Specific examples of the red phosphorescent dopant include, but are not limited to,

specific examples of the green phosphorescent dopant include but are not limited to,

specific examples of the blue light dopant include but are not limited to,

in one embodiment, the guest material may be Ir (piq)₂(acac)。

The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. 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, or other materials, which is not particularly limited in the present application. The host material is divided into a single host material and a mixed host material. Wherein the hybrid host material comprises an HT-type host material and an ET-type host material. Specifically, the single host material is, for example, but not limited to, a green host material:

red light host material:

the HT-type host material in the hybrid host material, such as but not limited to,

the ET-type host material may be, for example but not limited to,

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

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 a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. Preferably, a metal electrode comprising an Mg-Ag alloy is included as a cathode.

Optionally, the functional layer 300 may further include a hole injection layer 310, and the hole injection layer 310 is disposed on a surface of the anode 100 near the organic light emitting layer 330. Specifically, the hole injection layer 310 is sandwiched between the hole transport layer 320 and the anode 100. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and the like, which are not particularly limited in the present application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;

in one embodiment, the hole injection layer 310 may be F4-TCNQ.

Alternatively, as shown in fig. 1, an electron transport layer 340 may be further disposed between the cathode 200 and the organic light emitting layer 330. 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, and the electron transport material may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application, and the materials of the electron transport layer 340 include, but are not limited to, the following compounds:

in a specific embodiment, the material of the electron transport layer may include BCP and LiQ.

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. The electron injection layer material can be selected from Yb, LiF, NaCl, CsF and Li₂O、BaO、LiQ、NaCl、CsF、Li₂O、Cs₂CO₃One or more of Na, Li, Ca and Al.

In a specific embodiment, the electron-electron injecting material is Yb.

According to another embodiment, the electronic component may be a photoelectric conversion device, which may include an anode 100 and a cathode 200 oppositely disposed, and a functional layer 300 disposed between the anode 100 and the cathode 200, as shown in fig. 3; the functional layer 300 comprises an organic compound as provided herein. Among them, the functional layer includes a photoelectric conversion layer 360 as an energy conversion layer.

The organic compound provided herein may be used to form at least one organic thin layer in the functional layer 300 to improve the photoelectric conversion device performance, particularly to increase the open circuit voltage of the photoelectric conversion device or to increase the photoelectric conversion efficiency of the photoelectric conversion device.

Alternatively, the functional layer 300 includes a hole transport layer 320, and the hole transport layer 320 includes the organic compound of the present application.

According to a specific embodiment, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked. Wherein the hole transport layer 320 comprises the organic compound of the present application.

Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell.

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

According to one embodiment, as shown in fig. 2, the electronic device provided by the present application is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The electronic device 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.

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.

The present invention will be described in further detail below with reference to examples. However, the following examples are merely illustrative of the present invention and are not intended to limit the present invention.

Synthetic examples

Those skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare a wide variety of organic 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, and some of the intermediates that could not be purchased directly were prepared by simple reactions from commercially available starting materials and were used without further purification unless otherwise stated. The rest of the conventional reagents were purchased from Shang Wen Long chemical plant, Guangdong Guanghua chemical plant, Guangzhou chemical plant, Tianjin Shuichun chemical plant, Wuhan Xin Huayuan scientific and technological development Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, Qingdao Kaiyaku chemical plant, etc.

During purification, the chromatographic column is a silica gel column, and 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: ratio of 5% -95% (acetonitrile containing 0.1% formic acid) in (water containing 0.1% formic acid)), using electrospray ionization (ESI), at 210nm/254nm, with UV detection.

Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CDCl at room temperature₃、CD₂Cl₂TMS (0ppm) was used as a reference standard for the solvent (in ppm). When multiple peaks occur, the following abbreviations will be used: s (singleton), d (doublet), t (triplet), m (multiplet).

Intermediate synthesis:

in N₂Next, SA-1-1(30.0g,159.55mmol) as a starting material, SA-2-1(45.33g,132.96mmol) as a starting material, TBAB (0.86g,2.66mmol) as a starting material, potassium carbonate (27.53g,199.44mmol), tetrakis (triphenylphosphine) palladium (1.54g,1.33mmol), THF (180mL) and water (60mL) were added to a three-necked flask, and the mixture was stirred at elevated temperature to reflux, after 24 hours of reaction, the reaction was terminated, the organic layer was washed with water 3 times and extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure, followed by purification by column chromatography to give intermediate IM A-1-1(29.61g, yield 62.33%).

Referring to the synthesis method of intermediate IM A-1-1, intermediate IM A-1-X shown in Table 1 below was synthesized, wherein SA-2-X was used instead of SA-2-1, and reacted with SA-1-1 to synthesize intermediate IM A-1-X (X is a number) shown in Table 1 below.

TABLE 1

In N₂Next, IM A-1-1(29.30g,82.02mmol) and dry THF (300mL) were added to a three-necked flask, cooled to 0 deg.C, and CH was added dropwise₃MgBr (methyl magnesium bromide in THF, 12mL,98.42mmol), after addition, was heated to reflux and reacted for 6h, the organic layer was washed with water and extracted with DCM, and recrystallized from n-heptane/DCM to afford IMA-3-1(17.35g, 62.33% yield).

The intermediates IM A-3-X shown in Table 2 below were synthesized by referring to the synthesis method of the intermediate IM A-3-1, wherein the intermediate IM A-1-X (X is a number) was substituted for the intermediate IM A-1-1, and the intermediates IM A-3-X (X is a number) shown in Table 2 below were synthesized.

TABLE 2

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, sequentially adding an intermediate IM A-3-1(15.50g,45.68mmol), pinacol diboron (11.60g,45.68mmol) (a reactant SA-3-1), potassium acetate (6.72g, 68.52mmol), x-Phos (0.43g, 0.9136mmol), tris (dibenzylideneacetone) dipalladium (0.42g, 0.46mmol) and 1, 4-dioxane (155mL), heating to 75-85 ℃, refluxing for 3h, and cooling to room temperature after the reaction is finished. The reaction solution was extracted, the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was freed of the solvent under reduced pressure, the crude product was purified by recrystallization from toluene system, and filtered to give intermediate IM A-4-1(12.33g, yield 69.88%).

The intermediate IM A-4-X shown in Table 3 below was synthesized by referring to the synthesis method of the intermediate IM A-4-1, wherein the intermediate IM A-3-X was used in place of the intermediate IM A-3-1 to synthesize the intermediate IMA-4-X (X is a number) shown in Table 3 below.

TABLE 3

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 IM A-4-1(11.38g, 29.46mmol), reactant SA-4-1(7.02g, 29.46mmol), palladium acetate (0.066g, 0.2946mmol), potassium carbonate (6.10g, 44.19mmol), s-Phos (0.2419g, 0.5892mmol), toluene (69mL), absolute ethanol (22mL) and deionized water (22 mL); stirring and heating are started, reflux reaction is carried out for 4 hours when the temperature rises to 70-80 ℃, and cooling is carried out to room temperature after the reaction is finished. Extraction, washing with water, combining the organic phases, drying over anhydrous magnesium sulphate, concentrating the filtrate under reduced pressure and purifying the crude product by recrystallisation of the residue from a dichloromethane/n-heptane system gave solid intermediate IM A-5-1(7.79g, yield 71.33%).

Intermediate IM A-5-X shown in Table 4 below was synthesized by reference to the synthesis of intermediate IM A-5-1, wherein intermediate IM A-4-X was substituted for intermediate IM A-4-1 and reactant SA-4-X was substituted for reactant SA-4-1, to synthesize intermediate IMA-5-X (X is a number) as shown in Table 4 below.

TABLE 4

Adding intermediates IMA-3-1(6.89g,20.31mmol), SA-5-1(3.44g,20.31mmol), tris (dibenzylideneacetone) dipalladium (0.19g,0.203mmol), 2-dicyclohexyl phosphorus-2 ', 4 ', 6 ' -triisopropyl biphenyl (0.19g,0.406mmol) and sodium tert-butoxide (2.93g,30.47mmol) into toluene (56mL), heating to 108 ℃ under the protection of nitrogen, stirring for 1h, cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate, drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a dichloromethane/n-heptane system to yield the intermediate IMA-6-1 as a white-like solid (6.07g, 69.88% yield).

The intermediate IMA-6-X was synthesized with reference to the synthetic method of the intermediate IMA-6-1, except that IMA-Y-X (Y is 3 or 5) was used in place of IMA-3-1 and SA-5-X was used in place of SA-5-1, and the produced IMA-6-X and the yield thereof were as shown in Table 5 below.

TABLE 5

(II) compound synthesis:

synthesis example 1:

adding the intermediates IMA-6-1(4.78g,11.21mmol), SA-6-1(2.61g,11.21mmol), tris (dibenzylideneacetone) dipalladium (0.10g,0.1121mmol), 2-dicyclohexyl phosphorus-2 ', 6' -dimethoxy biphenyl (0.092g,0.2242mmol) and sodium tert-butoxide (1.62g,16.82mmol) into toluene (40mL), heating to 108 ℃ under the protection of nitrogen, and stirring for 2 h; then cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a toluene/n-heptane system to give compound 1 as a white solid (4.25g, yield 65.33%). LC-MS (ESI, pos.ion) M/z 580.3[ M + H ═ M]⁺. Synthesis examples 2 to 28:

compound X was synthesized in the same manner as in the synthesis of Compound 1 except that IMA-6-X was used in place of IM A-6-1 and SA-6-X was used as the starting material in place of SA-6-1, and the compounds thus obtained were as shown in Table 6 below.

TABLE 6

The nuclear magnetic data for some of the compounds are shown in table 7:

TABLE 7

Preparation and performance evaluation of organic electroluminescent device

Example 1

Red 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:N₂Plasma treating the surface to increaseThe sum of the work functions of the anode (experimental substrate) scavenges.

F4-TCNQ was vacuum-evaporated onto an experimental substrate (anode) to a thickness ofAnd TAPC is vapor-deposited on the hole injection layer to a thickness ofThe first hole transport layer of (1).

Vacuum evaporating compound 1 on the first hole transport layer to a thickness ofThe second hole transport layer of (1).

On the second hole transporting layer, RH-1: Ir (piq)₂(acac) reaction at a rate of 1: co-evaporation was carried out at a film thickness ratio of 0.03 to give a film having a thickness ofThe red light emitting layer (R-EML).

BCP and LiQ are mixed according to the weight ratio of 1:1 and are evaporated on the red light emitting layer to form the red light emitting diodeA thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layerAnd 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 is set toForming an organic capping layer (CPL).

Examples 2 to 28

Organic electroluminescent devices were fabricated by the same method as example 1, except that compounds shown in table 9 below were each substituted for compound 1 in forming the second hole transport layer.

Comparative examples 1 to 3

An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, and compound C shown in table 9 below were each substituted for compound 1 in forming the second hole transport layer.

The main material structures used in the above examples and comparative examples are shown in table 8 below:

TABLE 8

For the organic electroluminescent device prepared as above, at 20mA/cm²The device performance was analyzed under the conditions of (1), and the results are shown in table 9 below.

TABLE 9

From the results in table 9 above, it can be seen that, in examples 1 to 28 using the organic compound of the present application as a hole transport layer, compared with device comparative examples 1 to 3 corresponding to known compounds, the driving voltage of the organic electroluminescent device prepared using the organic compound of the present invention as a hole transport layer is reduced by at least 0.15V, the luminous efficiency (Cd/a) is improved by at least 15.4%, and the device lifetime can be improved by at least 17.2%.

The compound has such excellent carrier transmission characteristics, two indeno groups are adopted in the structure of the compound to carry out equidirectional condensation, a bisindeno derivative structure has stable carrier migration, four methyl substituents are added on a compound parent nucleus and are connected with one arylamine group, intermolecular pi-pi stacking is reduced, film forming property is improved, and the material has the advantages of high efficiency and long service life in devices. Two indenyl groups are condensed through conjugated double bonds, so that the hole mobility of a parent nucleus can be improved, four adjacent methyl groups are mutually influenced, the film forming property of the compound can be improved, the steric hindrance between the methyl groups is moderate, and the reduction of the stability of a connecting bond caused by the close proximity of a plurality of large steric hindrance groups is avoided. In the comparative compounds A and C, two indenyl groups are reversely condensed, and the electron density distribution is relatively dispersed, so that the hole transmission efficiency is insufficient, and in the comparative compound B, the steric hindrance between four adjacent phenyl groups is too large, so that the stability of the compound is reduced, and the efficiency and the service life of the device are obviously reduced.

The foregoing variations and modifications are within the scope of the present application. It will be understood that the application 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.