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 马林楠 于 2021-01-20 设计创作，主要内容包括：本申请涉及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。本发明的有机电致发光材料,分子内包含金刚烷基团与吲哚并咔唑衍生物的结构,增加共轭体系的电子密度,进而提高了有机化合物的空穴传导效率并且降低有机电致发光的驱动压力。将本发明的有机电致发光材料应用于有机电致发光器件的功能层时,能够显著改善有机电致发光器件的性能。(The application relates to an organic compound, an electronic element and an electronic device thereof, belonging to the technical field of organic electroluminescence. The organic electroluminescent material of the invention contains the structures of adamantyl groups and indolocarbazole derivatives in molecules, increases the electron density of a conjugated system, further improves the hole conduction efficiency of organic compounds and reduces the driving pressure of organic electroluminescence. When the organic electroluminescent material is applied to the functional layer of the organic electroluminescent device, the performance of the organic electroluminescent device can be obviously improved.)

1. An organic compound having a structural formula consisting of structures represented by chemical formula 1, chemical formula 2, and chemical formula 3:

wherein, represents a connection point where chemical formula 1 is connected to chemical formula 2, a connection point where chemical formula 1 is fused to chemical formula 3;

R₁、R₂、R₃and R₄The same or different from each other, and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms;

R₁、R₂、R₃、R₄with R_iIs represented by n₁～n₄With n_iIs represented by n_iRepresents R_iI is a variable, represents 1,2, 3 and 4, and when i is 2, 3 and 4, n_iSelected from 0, 1,2, 3 or 4; when i is 1, ni is selected from 0, 1,2 or 3; and when n is_iWhen greater than 1, any two n_iThe same or different;

l is 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;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

the substituents in L and Ar are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl with 3-12 carbon atoms, aryl with 6-12 carbon atoms, trimethylsilyl, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, cycloalkyl with 3-10 carbon atoms and alkoxy with 1-10 carbon atoms.

2. The organic compound of claim 1, wherein the organic compound has a structure as shown below:

3. the organic compound according to claim 1, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms;

preferably, the substituents in L are selected from deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl.

4. The organic compound of claim 1, wherein L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted benzoquinoxalylene group, a substituted or unsubstituted dibenzoquinoxalylene group;

preferably, the substituents in L are selected from deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl.

5. An organic compound according to claim 1, wherein L is selected from the group consisting of a single bond, a substituted or unsubstituted group P, and unsubstituted group P is selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group P has one or more substituents selected from the group consisting of: deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl; when the number of substituents in the group P is more than 1, the substituents may be the same or different.

6. The organic compound of claim 1, wherein L is selected from the group consisting of a single bond or the following group:

7. the organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms;

preferably, the substituents in Ar are selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothienyl, phenyl, naphthyl, carbazolyl, fluorenyl.

8. The organic compound of claim 1, wherein Ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinoxalyl, substituted or unsubstituted benzoquinolyl;

preferably, the substituents in Ar are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, carbazolyl, fluorenyl.

9. An organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted group T selected from the group consisting of:

the substituted group T has one or more substituents, and the substituents in the group T are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, carbazolyl, fluorenyl.

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

11. an organic compound according to claim 1, wherein R is₁、R₂、R₃、R₄Identical or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl.

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

13. 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 12;

preferably, the functional layer includes a light emitting layer including the organic compound.

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

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

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

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

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

Opto-electronic devices using organic materials are becoming increasingly popular for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, and therefore organic photovoltaic devices have the potential to be more cost-advantageous than inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for specific applications, such as fabrication on flexible substrates. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials may have performance advantages over traditional materials. For example, the wavelength at which the organic light-emitting layer emits light can generally be easily tuned with appropriate dopants.

In the prior art, US20160260908a1, KR102048609B1, etc. disclose materials that can prepare a light emitting layer in an organic electroluminescent device. However, there is still a need to develop new materials to further improve the performance of electronic components.

Disclosure of Invention

The present disclosure is directed to overcoming the above-mentioned deficiencies in the prior art and providing an organic compound, an electronic device and an electronic apparatus including the same, which can improve the light emitting efficiency and prolong the lifetime of the device.

In order to achieve the purpose of the invention, the following technical scheme is adopted in the application:

according to a first aspect of the present application, there is provided an organic compound having a structural formula consisting of structures represented by chemical formula 1, chemical formula 2, and chemical formula 3:

wherein, represents a connection point where chemical formula 1 is connected to chemical formula 2, a connection point where chemical formula 1 is fused to chemical formula 3;

R₁、R₂、R₃and R₄The same or different from each other, and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 3 to 12 carbon atoms;

R₁、R₂、R₃、R₄with R_iIs represented by n₁～n₄With n_iIs represented by n_iRepresents R_iI is a variable, represents 1,2, 3 and 4, and when i is 2, 3 and 4, n_iSelected from 0, 1,2, 3 or 4; when i is 1, ni is selected from 0, 1,2 or 3; and when n is_iWhen greater than 1, any two n_iThe same or different;

l is 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;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

the substituents in L and Ar are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl with 3-12 carbon atoms, aryl with 6-12 carbon atoms, trimethylsilyl, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, cycloalkyl with 3-10 carbon atoms and alkoxy with 1-10 carbon atoms.

The structure of the compound is mainly that an adamantyl group is combined with an indolocarbazole derivative, the indolocarbazole group and the carbazole group are fused to form a core group, and when the indolocarbazole derivative is used as a main material of an organic light-emitting layer, due to the large electron cloud density of the indolocarbazole derivative, the hole mobility of the light-emitting layer is improved, balance of electrons and holes in the organic light-emitting layer is facilitated, the light-emitting efficiency of an electroluminescent device is improved, and the driving voltage of the organic electroluminescent device is reduced. The adamantyl groups have larger space volume and higher rigidity, and can reduce the interaction force among conjugated structures and reduce the accumulation among molecules, thereby improving the current efficiency. The adamantane is combined with the indolocarbazole derivative, the degree of freedom among molecules is increased, the compound is not easy to crystallize in an amorphous state and is more stable, the compound is bonded with a carbazole group, the molecular symmetry is reduced, the film-forming property of the compound in the application is improved, and the current efficiency and the luminous efficiency are improved.

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 disclosure.

Drawings

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

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; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic electroluminescent layer; 340. a hole blocking 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 disclosure.

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 major technical ideas of the application.

The present application provides an organic compound having a structural formula consisting of structures represented by chemical formula 1, chemical formula 2, and chemical formula 3:

wherein, represents a connection point where chemical formula 1 is connected to chemical formula 2, a connection point where chemical formula 1 is fused to chemical formula 3;

R₁、R₂、R₃and R₄Identical or different from each other, and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, cyano,A heteroaryl group having 3 to 12 carbon atoms;

R₁、R₂、R₃、R₄with R_iIs represented by n₁～n₄With n_iIs represented by n_iRepresents R_iI is a variable, represents 1,2, 3 and 4, and when i is 2, 3 and 4, n_iSelected from 0, 1,2, 3 or 4; when i is 1, ni is selected from 0, 1,2 or 3; and when n is_iWhen greater than 1, any two n_iThe same or different;

l is 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;

ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms or substituted or unsubstituted heteroaryl with 3-30 carbon atoms;

the substituents in L and Ar are the same or different and are independently selected from deuterium, halogen, cyano, heteroaryl with 3-12 carbon atoms, aryl with 6-12 carbon atoms, trimethylsilyl, alkyl with 1-5 carbon atoms, halogenated alkyl with 1-5 carbon atoms, cycloalkyl with 3-10 carbon atoms and alkoxy with 1-10 carbon atoms.

In the present application, "' indicates a connection point of formula 1 to formula 2 and a connection point of formula 1 to formula 3 fused thereto" means that formula 2 is connected to any one of connection sites in formula 1 through a connection site, and formula 3 is connected to any two adjacent sites in formula 1 through a connection site.

In the present application, the ring refers to a saturated or unsaturated ring such as cyclohexane, cyclopentane, a 6 to 12 membered aromatic ring or a 5 to 12 membered heteroaromatic ring, etc., but is not limited thereto.

In the present application, the description that "… … is independently" and "… … is independently" and "… … is independently selected from" is used interchangeably and should be understood broadly to mean that the particular items expressed between the same symbols in different groups do not affect each other or that the particular items expressed between the same symbols in the same groups do not affect each otherInfluence. 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 is, for example, deuterium, halogen, cyano, heteroaryl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, and optionally, any two of the substituents may be mutually connected 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, 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 the arylene group and all carbons on the substituent thereofThe atomic number is 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. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.

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. Further, the alkyl group may be substituted or unsubstituted.

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 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, numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "3 to 10 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Cycloalkyl groups can also be divided into monocyclic one having only one ring, bicyclic one having two rings, or polycyclic one having three or more rings. Cycloalkyl groups can also be divided into spirocyclic rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and two or more rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted. For example, cyclohexane.

In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of 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, phenanthrenyl, pyrenyl,and the like. The "aryl" group herein may have 6 to 30 carbon atoms, in some embodiments 6 to 20 carbon atoms, and in other embodiments 6 to 12 carbon atoms. 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, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atom, halogen, cyano, tert-butyl, heteroaryl, alkyl, cycloalkyl, alkoxy, and the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.

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

In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The "heteroaryl" groups herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 3 to 12. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.

In this application, 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 more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl 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, specific examples of the heteroaryl group as the substituent include, but are not limited to: pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl.

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).

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

In the present application, halogen may be fluorine, chlorine, bromine, iodine.

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

In the present application, the organic compound has a structure as shown below:

in one embodiment of the present application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms;

preferably, the substituents in L are selected from deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl.

In one embodiment of the present application, L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted benzoquinoxalylene group, a substituted or unsubstituted dibenzoquinoxalylene group;

preferably, the substituents in L are selected from deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl.

In one embodiment of the present application, L is selected from a single bond, a substituted or unsubstituted group P, the unsubstituted group P being selected from the group consisting of:

wherein the content of the first and second substances,represents a chemical bond; the substituted group P has one or more substituents selected from the group consisting of: deuterium, fluoro, cyano, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, biphenyl, methyl, ethyl, n-propyl, isopropyl, tert-butyl; when the number of substituents in the group P is more than 1, the substituents may be the same or different.

In one embodiment of the present application, L is selected from a single bond or the group consisting of:

in one embodiment of the present application, Ar is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms;

preferably, the substituents in Ar are selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothienyl, phenyl, naphthyl, carbazolyl, fluorenyl.

In one embodiment of the present application, Ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted benzoquinolyl;

preferably, the substituents in Ar are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, carbazolyl, fluorenyl.

In one embodiment of the present application, Ar is selected from a substituted or unsubstituted group T selected from the group consisting of:

the substituted group T has one or more substituents, and the substituents in the group T are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, phenyl, naphthyl, carbazolyl, fluorenyl.

In one embodiment of the present application, Ar is selected from the group consisting of:

in one embodiment of the present application, R₁、R₂、R₃、R₄Identical or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl.

In one embodiment of the present application, the organic compound is selected from the group formed by:

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.

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, an organic electroluminescent layer 330, a hole blocking layer 340, an electron transport layer 350, and an electron injection layer 360; the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322; the hole injection layer 310, the hole transport layer 320, the organic electroluminescent layer 330, the hole blocking layer 340, the electron transport layer 350, and the electron injection layer 360 may be sequentially formed on the anode 100, and the organic electroluminescent layer 330 may contain an organic compound described in the first aspect of the present application, and preferably at least one of the compounds 1 to 104.

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

Alternatively, the hole transport layer 320 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds, which are not specifically limited herein. For example, in one embodiment of the present application, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322, the first hole transport layer 321 is composed of a compound NPB, and the second hole transport layer 322 is composed of a compound PAPB.

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

In one embodiment of the present application, the host material of the organic electroluminescent layer 330 is composed of the organic compound provided herein and RH — N; in another embodiment of the present application, the host material of the organic electroluminescent layer 330 is composed of the organic compound provided herein and RH — P. The organic compound structure provided by the application is mainly characterized in that an adamantyl group is combined with an indolocarbazole derivative, the indole group and the carbazole group are fused to form a core group, and when the indolocarbazole derivative is used as a main body material of an organic light-emitting layer, due to the large electron cloud density of the indolocarbazole derivative, the hole mobility of the light-emitting layer is improved, the balance of electrons and holes in the organic light-emitting layer is facilitated, the light-emitting efficiency of electroluminescence is improved, and the driving pressure of the organic electroluminescence is reduced. The adamantyl groups have larger space volume and higher rigidity, and can reduce the interaction force among conjugated structures and reduce the accumulation among molecules, thereby improving the current efficiency. The adamantane is combined with the indolocarbazole derivative, the degree of freedom among molecules is increased, the compound is not easy to crystallize in an amorphous state and is more stable, the compound is bonded with a carbazole group, the molecular symmetry is reduced, the film-forming property of the compound in the application is improved, the efficiency is improved, and the organic luminescent material is effectively protected.

The guest material of the organic electroluminescent 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. For example, in one embodiment of the present application, the guest material of the organic light emitting layer 330 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, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, 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 a multilayer material such as LiF/Al, Liq/Al, LiO₂Al, LiF/Ca, LiF/Al and BaF₂But not limited thereto,/Ca. A metal electrode comprising silver and magnesium is preferably included as the cathode 200.

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. For example, in one embodiment of the present application, the hole injection layer 310 is comprised of HAT-CN; in another embodiment of the present application, the hole injection layer 310 is also comprised 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. For example, in one embodiment of the present application, the electron injection layer 360 is LiQ.

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

Synthetic examples

One skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare many other compounds of the invention, and that other methods for preparing the compounds of the invention are considered to be within the scope of the invention. For example, the synthesis of those non-exemplified compounds according to the present invention 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 in addition to those described herein, or by some routine modification of reaction conditions. In addition, the reactions disclosed herein or known reaction conditions are also recognized as being applicable to the preparation of other compounds of the present invention.

Synthesis of Compound 1

Compound 1 was synthesized by the following synthetic route

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirrer, a thermometer and a spherical condenser for replacement for 15min, adding 1, 5-dibromo-2-chloro-4-fluorobenzene (0.20mol, 58.6g) (reactant A-1), 3-bromocarbazole (0.20mol, 50g) (reactant A-2) and DMF (500mL), slowly adding cesium carbonate (0.6mol, 195.5g), starting stirring, heating to 175-185 ℃ for reaction for 6h, and cooling to room temperature after the reaction is finished. Extracting and separating an organic phase by using dichloromethane, 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; column chromatography with eluent EA: Hept ═ 1:10 afforded intermediate I-1(42.0g, 53%) as a white solid.

Referring to the reaction route of intermediate I-1, intermediate II-1, intermediate III-1, intermediate IV-1 and intermediate V-1 were prepared by substituting reactant a-1, reactant B-1, reactant C-1 for 1, 5-dibromo-2-chloro-4-fluorobenzene (reactant a-1), reactant a-2, reactant B-2, reactant C-2, reactant D-2 for 3-bromocarbazole (reactant a-2), wherein the number, structure, synthesis yield, etc. of each intermediate are shown in table 1.

TABLE 1

(2) Synthesis of intermediate I-2

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring device, a thermometer and a spherical condenser tube for replacement for 15min, adding intermediate I-1(0.175mol, 90.2g), allyl chloride [1, 3-bis (2, 6-diisopropylbenzene) imidazole-2-yl ] palladium (0.0035mol, 2.1g), potassium carbonate (0.525mol, 72.5g) and DMAc (800mL), starting stirring, heating to 125-phase 135 ℃, reacting for 12h, and cooling to room temperature after the reaction is finished. Extracting and separating an organic phase by using dichloromethane, 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; column chromatography with eluent DCM: Hept ═ 1:4 gave intermediate I-2(56.9g, 75%) as a white solid.

Referring to the reaction route of intermediate I-2, intermediate II-2, intermediate III-2, intermediate IV-2 and intermediate V-2 were prepared by substituting intermediate II-2, intermediate III-1, intermediate IV-1 and intermediate V-1 for intermediate I-1, wherein the number, structure, synthesis yields, etc. of each intermediate are shown in Table 2.

TABLE 2

(3) Synthesis of intermediate I-3

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 I-2(0.131mol, 56.9g), 2-nitrophenylboronic acid (0.131mol, 21.9g) (reactant A-3), potassium carbonate (0.262mol, 36.2g), tetrakis (triphenylphosphine) palladium (0.001mol, 1.5g), TBAB (0.0026mol, 0.84g) were added, and a mixed solvent of toluene (300mL), ethanol (150mL), and water (100mL) was added. Stirring is started, reflux reaction is carried out for 12 hours, and after the reaction is finished, the reaction is 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; column chromatography with eluent DCM: Hept ═ 1:5 gave intermediate I-3(53.0g, 85%) as a white solid.

Referring to the reaction route of intermediate I-3, intermediate II-2, intermediate III-2, intermediate IV-2 and intermediate V-2 were substituted for intermediate I-2, reactant A-3, reactant B-3 were substituted for 2-nitrophenylboronic acid (reactant A-3) to prepare intermediate II-3, intermediate III-3, intermediate IV-3 and intermediate V-3, wherein the numbering, structure, synthesis yields, etc. of each intermediate are shown in Table 3.

TABLE 3

(4) Synthesis of intermediate I-4

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a constant-pressure dropping funnel for replacement for 15min, adding a tetrahydrofuran solution (50mL) containing magnesium strips (3.2g, 0.133mol) and 1, 2-dibromoethane (0.2g), starting stirring, cooling to 0 ℃ to-10 ℃, dropping a tetrahydrofuran solution (400mL) containing an intermediate I-3(53.0g, 0.111mol), raising the temperature to room temperature after the dropping is finished, stirring for 3h, removing residual magnesium strips, distilling under reduced pressure to remove tetrahydrofuran to obtain a solid, adding a solvent dichloromethane (100mL), slowly dropping a dichloromethane (100mL) solution containing 1-bromoadamantane (23.66g, 0.111mol) at room temperature under the protection of nitrogen, refluxing for 2h, cooling to room temperature, adding the reaction liquid into 2mol/L hydrochloric acid, separating an organic phase, extracting an aqueous phase with n-heptane, combining organic phases, washing with water, drying with magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate I-4(36.5g, 62%) as a colorless oil.

Referring to the reaction route of intermediate I-4, intermediate II-4, intermediate III-4, intermediate IV-4 and intermediate V-4 were prepared by substituting intermediate II-3, intermediate III-3, intermediate IV-3 and intermediate V-3 for intermediate I-3, wherein the number, structure, synthesis yields, etc. of each intermediate are shown in Table 4.

TABLE 4

(5) Synthesis of intermediate I-4

Introducing nitrogen (0.100L/min) into a three-neck flask equipped with mechanical stirring, thermometer and spherical condenser for 15min, adding intermediate I-4(0.068mol, 36.5g) and PPh₃(0.17mol, 44.59g) and dichlorobenzene (300mL), the mixture was stirred under reflux for 5 hours, and after completion of the reaction, the mixture was cooled to room temperature. Extracting and separating an organic phase by using dichloromethane and deionized 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 column chromatography on silica gel using a dichloromethane/n-heptane system to yield intermediate I (16.0g, 51%) as a white solid.

Intermediate II, intermediate III, intermediate IV and intermediate V were prepared by substituting intermediate II-4, intermediate III-4, intermediate IV-4 and intermediate V-4 for intermediate I-4 with reference to the reaction scheme for intermediate I, wherein the numbering, structure, synthesis yields, etc. of each intermediate are shown in Table 5.

TABLE 5

(6) Synthesis of Compound 1

Introducing nitrogen (0.100L/min) into a three-neck flask provided with a mechanical stirring thermometer and a spherical condenser tube for replacement for 15min, adding an intermediate I (16g, 0.034mol), 4-bromobiphenyl (7.9g, 0.034mol) (a reactant A-4) and toluene (130mL), starting stirring, refluxing for 30min, cooling to 70-80 ℃, adding tris (dibenzylideneacetone) dipalladium (0.3g, 0.0003mol), 2-dicyclohexylphosphonium-2 ',6' -dimethoxybiphenyl (0.272g, 0.0006mol) and sodium tert-butoxide (4.9g, 0.051mol), heating to 105-110 ℃ for reaction for 3h, and cooling to room temperature after the reaction is finished. Extracting with toluene to separate organic phase, washing with water to neutralityDrying the organic phase with anhydrous magnesium sulfate, filtering, and distilling the filtrate under reduced pressure to remove the solvent; the crude product was purified by recrystallization from toluene to give compound 1 as a white solid (16.9g, 81%). LC-MS (ESI): 617.29[ M + H ] M/z]⁺。

Referring to the reaction scheme of Compound 1, reactant A-4, reactant B-4, reactant C-4, reactant D-4, reactant E-4, reactant F-4, reactant G-4, reactant H-4, reactant I-4, reactant J-4, reactant K-4, reactant L-4, reactant M-4, reactant N-4, reactant O-4, reactant P-4, reactant Q-4, reactant R-4, reactant S-4, reactant T-4, reactant U-4, reactant V-4, reactant W-4 and reactant X-4 are used in place of reactant A-4, and intermediate I, intermediate II, intermediate III, etc. are used in place of reactant A-4, Intermediates IV and V the following compounds were prepared in place of intermediate I, and the number, structure, characterization, synthesis yields, and the like of each compound are shown in table 6.

TABLE 6

Part of the compound NMR data are shown in Table 7 below

TABLE 7

Preparation and performance evaluation of organic electroluminescent device

Example 1

Red organic electroluminescent device

Will have a thickness ofThe anode ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), 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:N₂Plasma is used for surface treatment to increase the work function of an anode (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 ofA Hole Injection Layer (HIL); and vacuum evaporating NPB compound on the hole injection layer to form a layer with a thickness ofA first hole transport layer (HTL 1). Vacuum evaporating PAPB on the first hole transport layer to form a layer with a thickness ofAnd a second hole transport layer (HTL 2).

On the second hole transport layer (HTL2), RH-N: compound 1: ir (piq)₂(acac) at 50%: 50%: 3% of the total amount of the components are co-evaporated to form a film with a thickness ofRed light emitting layer (EML).

ET-06 (structural formula shown below) and LiQ (structural formula shown below) are mixed in a weight ratio of 1:1 and can be formed by a vacuum evaporation processA thick Electron Transport Layer (ETL). Subsequently, LiQ was evaporated on the electron transport layer to form a thickness ofElectron Injection Layer (EIL).

Mixing magnesium (Mg) and silver (Ag) at a rate of 1:9, vacuum-evaporating on the Electron Injection Layer (EIL) to form a layer with a thickness ofThe cathode 200.

Further, a layer having a thickness ofCP-05 (structural formula is shown below), and a capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device.

Wherein F4-TCNQ, NPB, PAPB, RH-N, Ir (piq)₂(acac), ET-06, LiQ, CP-05, Compound A, Compound B, Compound C, Compound RH-P, Compound D, Compound E, and Compound F have the following structural formulas:

TABLE 8

Examples 2 to 17

A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compounds shown in table 9 were used instead of compound 1 in forming the light emitting layer (EML).

Example 18

In addition to example 1, RH-N in example 1, Compound X, Ir, (piq) was added to form an organic light-emitting layer by changing the material of the light-emitting layer₂(acac) 50%: 50%: 3% (vapor deposition)Rate) of vapor deposition into the compound X, RH-P, Ir (piq)₂(acac) was co-evaporated at a ratio of 50%: 50%: 3% (evaporation rate) to form a film with a thickness of 50% by weightRed organic light emitting layer (EML).

Examples 19 to 25

A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compounds shown in table 9 were used instead of the compound 70 in forming the light-emitting layer (EML).

Comparative example 1

A red organic electroluminescent device was produced in the same manner as in example 1, except that the compound a was used instead of the compound 1 to form an emission layer (EML).

Comparative example 2

A red organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound B was used instead of the compound 1 to form an emission layer (EML).

Comparative example 3

A red organic electroluminescent device was produced in the same manner as in example 1, except that the compound C was used instead of the compound 1 to form an emission layer (EML).

Comparative example 4

A light-emitting layer (EML) was formed using the compound RH — P instead of the compound 1, and a red organic electroluminescent device was fabricated in the same manner as in example 1.

Comparative example 5

A red organic electroluminescent device was fabricated in the same manner as in example 18, except that the compound D was used instead of the compound 70 to form an emission layer (EML).

Comparative example 6

A red organic electroluminescent device was fabricated in the same manner as in example 18, except that the compound E was used instead of the compound 70 to form an emission layer (EML).

Comparative example 7

A red organic electroluminescent device was fabricated in the same manner as in example 18, except that the compound E was used instead of the compound 70 to form an emission layer (EML).

Wherein IVL (Current, Voltage, Brightness) data contrast, T95 lifetime is 20mA/cm²Test results at current density.

Table 9: performance test results of red organic electroluminescent device

From the results of the above table 9, it is understood that the voltage of the organic electroluminescent devices of examples 1 to 17, which are compounds of the light emitting layer, is reduced by 0.12V, the current efficiency (Cd/a) is improved by at least 14.29%, the external quantum efficiency is improved by at least 15.38%, the lifetime is improved by at least 8.25%, and the maximum lifetime can be improved by at least 146h, compared with the devices of comparative examples 1 to 4, which correspond to known compounds. Examples 18 to 25 of the compounds as the light-emitting layer showed a decrease in voltage of 0.25V, an increase in luminous efficiency (Cd/A) of at least 18.15%, an increase in external quantum efficiency of at least 18.15%, an increase in lifetime of at least 11.25%, and a maximum lifetime of at least 122h, as compared with comparative examples 4 to 7 of the devices corresponding to known compounds. Therefore, the compound has the characteristics of improving both the luminous efficiency and the service life. From the above data, it is clear that the use of the organic compound of the present application as the light-emitting layer of the electronic element significantly improves the light-emitting efficiency (Cd/a), the External Quantum Efficiency (EQE), and the lifetime (T95) of the electronic element. Therefore, the organic electroluminescent device with high luminous efficiency and long service life can be prepared by using the organic compound in the organic electroluminescent layer.

It should be understood that this application is not intended to limit the application to the details of construction and the arrangement of components set forth in the specification. The application is capable of other embodiments and of being practiced and carried out in various ways. 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.