CN114075215B - Organic compound, organic electroluminescent device comprising same and electronic device - Google Patents

Organic compound, organic electroluminescent device comprising same and electronic device Download PDF

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CN114075215B
CN114075215B CN202110647816.3A CN202110647816A CN114075215B CN 114075215 B CN114075215 B CN 114075215B CN 202110647816 A CN202110647816 A CN 202110647816A CN 114075215 B CN114075215 B CN 114075215B
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CN114075215A (en
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马天天
杨敏
杨雷
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application provides an organic compound, an organic electroluminescent device and an electronic device containing the same, and belongs to the field of organic electroluminescence. The structure of the organic compound is shown as formula 1, and the organic compound is applied to an organic electroluminescent device, so that the performance of the organic electroluminescent device can be remarkably improved.
Figure DDA0003109899320000011

Description

Organic compound, organic electroluminescent device comprising same and electronic device
Technical Field
The application relates to the technical field of organic electroluminescence, in particular to an organic compound, an organic electroluminescent device comprising the same and an electronic device.
Background
Along 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 becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of 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, it generally includes 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 cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at 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 to release energy outwards, so that the electroluminescent layer emits light outwards.
At present, for a red light organic electroluminescent device, there are still problems of reduced luminous efficiency, shortened service life and the like, thereby resulting in reduced device performance. Therefore, organic materials have to solve these efficiency or lifetime problems, and there is a continuous need to develop new materials for organic light emitting devices that are highly efficient, long-lived, and suitable for mass production.
It should be noted that the information disclosed in the foregoing background section is only for enhancing understanding of the background of the present application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The present application aims to overcome the defects in the prior art, and provides an organic compound, an organic electroluminescent device and an electronic device containing the same, which can improve luminous efficiency and prolong service life of the device.
In order to achieve the purpose of the invention, the application adopts the following technical scheme:
according to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
Figure BDA0003109899300000011
wherein X is selected from O or S;
L、L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L 3 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 each group is independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
each R is 1 、R 2 、R 3 And R is 4 Are independently selected from deuterium and halogenA group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0, 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 Represents a substituent R 3 Number n of (n) 3 Selected from 0, 1 or 2, when n 3 When the number is greater than 1, any two R 3 The same or different;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 0, 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
said L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, and alkoxy group having 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring.
The application uses a special carbazole condensed ring derivative structure as a core, and combines with triarylamine groups, so that molecules have high hole mobility, proper T1 energy level (triplet state energy level) and stable chemical structure. The organic compound is suitable for being used as a main material of an organic electroluminescent device, and can improve the performance of the organic electroluminescent device.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer 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 comprising the organic electroluminescent device described above.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device of 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; 321. a hole transport layer; 322. a hole assist 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.
Specific embodiments thereof have been shown by way of example in the drawings and will herein be described in more detail. These drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but to illustrate the concepts of the present application to those skilled in the art by reference to specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may 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 the 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 present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, 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 present application. One skilled in the relevant art will recognize, however, that the aspects of the application can be practiced without one or more of the specific details, or with other methods, components, materials, etc. In other instances, well-known structures, materials, or operations are not shown or described in detail to avoid obscuring the main technical idea of the present application.
The application provides an organic compound, wherein the structural general formula of the organic compound is shown as formula 1:
Figure BDA0003109899300000031
wherein X is selected from O or S;
L、L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L 3 a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
each R is 1 、R 2 、R 3 And R is 4 Are independently selected from deuterium, halogen groups, and cyanoA group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 The same or different;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0, 1 or 2, when n 2 When the number is greater than 1, any two R 2 The same or different;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 0, 1 or 2, when n 3 When the number is greater than 1, any two R 3 The same or different;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 0, 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
said L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuteroalkyl group having 1 to 10 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, and alkoxy group having 1 to 10 carbon atoms;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a ring.
In this application, the description that "each independently selected from" and "each independently selected from" are used interchangeably and should be construed broadly to mean that specific items expressed between the same symbols in different groups do not affect each other, or that specific items expressed between the same symbols in the same groups do not affect each other. For example, "
Figure BDA0003109899300000032
Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on 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 each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having a substituent Rc. Wherein Rc, the substituent mentioned above, may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuteroalkyl group having 1 to 10 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms.
In the present application, a "substituted" functional group may be substituted with one or more substituents of Rc described above; when two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a ring with the atom; when two adjacent substituents Rc are present on a functional group, the adjacent two substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event may, but need not, occur, and that the description includes instances where the event occurs or does not. For example, "optionally, two adjacent substituents are x to form a ring; by "is meant that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 1 When there are 2 or more substituents and any adjacent substituents form a ring, the ring formed is a saturated ring or an unsaturated ring, and the number of carbon atoms is 5 to 13, for example: fluorene ring, benzene ring, naphthalene ring, cyclopentane, cyclohexane, adamantane, and the like.
In the present application, "optionally, in Ar 1 、Ar 2 In which any two adjacent substituents form a ring with each other means that the ring is formed in Ar 1 Or Ar 2 Any two adjacent substituents may or may not form a ring. For example, when Ar 1 When two adjacent substituents form a ring, the number of carbon atoms of the ring is 5-13, and the ring may be saturated or unsaturated. For example: cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, fluorene ring, and the like, but is not limited thereto.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is selected from a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms. For example: ar is
Figure BDA0003109899300000041
The number of carbon atoms is 7; l is->
Figure BDA0003109899300000042
The number of carbon atoms is 12.
In the present application, "hetero" means that at least 1 hetero atom such as B, N, O, S, P, si or Se is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, in this application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Furthermore, alkyl groups 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 this application cycloalkyl refers to saturated hydrocarbons containing alicyclic structures, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-10 carbon atoms, a numerical range such as "3 to 10" referring to each integer in the given range; for example, "3 to 10 carbon atoms" refers to cycloalkyl groups 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 may be substituted or unsubstituted. Examples of cycloalkyl groups are cyclopentylalkyl, cyclohexenyl, adamantyl.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Wherein the fused ring aryl groups may include, for example, bicyclic fused aryl groups (e.g., naphthyl), tricyclic Condensed aryl (e.g., phenanthryl, fluorenyl, anthracyl), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl, triphenylene, pyrenyl, benzofluoranthryl,
Figure BDA0003109899300000051
A base, etc.
In this application, a "substituted or unsubstituted aryl" may contain from 6 to 40 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 30, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 25, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 12. For example, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 12, 13, 14, 15, 18, 20, 24, 25, 28, 29, 30, 40, although other numbers are possible and are not listed herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, alkoxy group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of aryl groups as substituents include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4 or 5 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may 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, dibenzothiophenyl, 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 thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds.
In this application, a "substituted or unsubstituted heteroaryl" may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 24, in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 20, in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 5 to 12. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, although other numbers are also possible and are not listed here.
In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group 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 of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: pyridyl, carbazolyl, dibenzofuranyl, dibenzothienyl.
In the present application, halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, trimethylsilyl group, triethylsilyl group and the like.
In the present application, specific examples of the haloalkyl group having 1 to 10 carbon atoms include, but are not limited to, trifluoromethyl.
In the present application, non-positional connection means a single bond extending from a ring system
Figure BDA0003109899300000061
It means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
Figure BDA0003109899300000062
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formula (X '-1) -formula (X' -4).
Figure BDA0003109899300000063
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In one embodiment of the present application, n 1 ，n 2 ，n 3 ，n 4 All 0.
L, L in one embodiment of the present application 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally, the L, L 1 、L 2 Each substituent of (a) is independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms.
Specifically, the L, L 1 、L 2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In another embodiment of the present application L, L 1 、L 2 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 fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazole group.
In a specific embodiment of the present application, L is selected from a single bond or phenylene.
Optionally, L is selected from the group consisting of a single bond or:
Figure BDA0003109899300000071
in a specific embodiment of the present application, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted group V, the unsubstituted group V being selected from the group consisting of:
Figure BDA0003109899300000072
wherein,,
Figure BDA0003109899300000073
represents a chemical bond; the substituted group V has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of V is greater than 1, the substituents may be the same or different.
Alternatively, L 1 、L 2 Each independently selected from the group consisting of:
Figure BDA0003109899300000074
in one embodiment of the present application, L 3 Selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally, the L 3 Each substituent of (a) is independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms.
Specifically, the L 3 Specific examples of substituents include, but are not limited to: deuterium, fluorine, cyanoMethyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In another embodiment of the present application, L 3 Each independently selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, and substituted or unsubstituted carbazole.
In a specific embodiment of the present application, L 3 Each independently selected from the group consisting of substituted or unsubstituted groups H selected from the group consisting of:
Figure BDA0003109899300000081
wherein,,
Figure BDA0003109899300000082
represents a chemical bond; the substituted group H has one or more substituents thereon, each of which is independently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the number of substituents of H is greater than 1, the substituents may be the same or different.
Optionally, the L 3 Is selected from the group consisting of:
Figure BDA0003109899300000083
in one embodiment of the present application, ar 1 、Ar 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
Optionally, the Ar 1 、Ar 2 Each substituent of (a) is independently selected from deuterium, halogen group, cyano group, alkyl group having 1-5 carbon atoms, cycloalkyl group having 5-10 carbon atoms, aryl group having 6-20 carbon atoms, A triphenylsilyl group, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, and a deuterated alkyl group having 1 to 5 carbon atoms.
Optionally in Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 ring carbon atoms. For example, in Ar 1 、Ar 2 Any two adjacent substituents form a cyclohexane, cyclopentane, adamantane, phenyl, naphthalene or fluorene ring.
Specifically, the Ar 1 、Ar 2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, tridentate methyl.
In another embodiment of the present application, ar 1 、Ar 2 Each independently 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 2,3 benzofluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
Optionally, the Ar 1 、Ar 2 Each of the substituents of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, tridentate methyl;
optionally in Ar 1 、Ar 2 Any two adjacent substituents form a fluorene ring
Figure BDA0003109899300000091
In a specific embodiment of the present application, the Ar 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups W, wherein unsubstituted groups W are selected from the group consisting of:
Figure BDA0003109899300000092
wherein,,
Figure BDA0003109899300000093
represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, adamantyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, tridentate methyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
Alternatively, ar 1 、Ar 2 Each independently selected from the group consisting of:
Figure BDA0003109899300000094
Figure BDA0003109899300000101
optionally, the organic compound is selected from the group consisting of:
Figure BDA0003109899300000102
/>
Figure BDA0003109899300000111
/>
Figure BDA0003109899300000121
/>
Figure BDA0003109899300000131
/>
Figure BDA0003109899300000141
/>
Figure BDA0003109899300000151
/>
Figure BDA0003109899300000161
/>
Figure BDA0003109899300000171
/>
Figure BDA0003109899300000181
/>
Figure BDA0003109899300000191
/>
Figure BDA0003109899300000201
/>
Figure BDA0003109899300000211
/>
Figure BDA0003109899300000221
/>
Figure BDA0003109899300000231
/>
Figure BDA0003109899300000241
/>
Figure BDA0003109899300000251
/>
Figure BDA0003109899300000261
/>
Figure BDA0003109899300000271
the present application also provides an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and at least one functional layer interposed between the anode and the cathode, the functional layer comprising the organic compound of the present application.
In one specific embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device of the present application includes an anode 100, a cathode 200, and at least one functional layer 300 interposed between the anode layer and the cathode layer, the functional layer 300 including a hole injection layer 310, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330, an electron transport layer 350, and an electron injection layer 360.
Optionally, a hole blocking layer 340 may be disposed between the organic electroluminescent layer 330 and the electron transport layer 350. The organic electroluminescent layer 330 may contain the organic compound described in the first aspect of the present application.
Alternatively, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadiumChromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in one embodiment of the present application, hole transport layer 321 consists of HT-01.
Alternatively, the hole auxiliary layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, in one embodiment of the present application, hole assist layer 322 is comprised of HT-02.
Alternatively, the organic electroluminescent layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Alternatively, the organic electroluminescent layer 330 is composed of a host material and a guest material, and holes and electrons injected into the organic electroluminescent layer 330 may be recombined at the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
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 are not particularly limited herein.
In one embodiment of the present application, a red organic electroluminescent device, organic electroluminescent layer 330, comprises an organic compound as described herein, RH-N, and a guestMaterial Ir (piq) 2 (acac)。
The electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in this application. For example, in one embodiment of the present application, electron transport layer 350 may be composed of ET-01 and LiQ.
Optionally, a hole blocking layer 340 is provided between the organic electroluminescent layer 330 and the electron transport layer 350. The hole blocking layer may include one or more hole blocking materials, which are not particularly limited in this application.
Alternatively, the cathode 200 includes a cathode material that is a material having 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 multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. A metal electrode containing silver and magnesium is preferably included as a cathode.
Optionally, a hole injection layer 310 may also be provided 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. In one embodiment of the present application, hole injection layer 310 may be composed of PtPC.
Optionally, an electron injection layer 360 may also be provided 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, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 360 may include ytterbium (Yb).
The application also provides an electronic device comprising the organic electroluminescent device.
For example, as shown in fig. 2, the electronic device provided in the present application is a first electronic device 400, where 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 type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc. Since the first electronic device 400 has the above-mentioned organic electroluminescent device, the first electronic device has the same beneficial effects, and the description thereof is omitted herein.
The present application will be described in detail below in connection with examples, but the following description is intended to explain the present application and is not intended to limit the scope of the present application in any way.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many other compounds of the present application, and that other methods for preparing compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those compounds not exemplified in accordance with the present application may be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. In addition, the inverse compounds disclosed herein are synthesized.
Synthesis of intermediate a 1-1:
Figure BDA0003109899300000291
12H-benzofuran [3,2-a ] carbazole (32.5 g;126.2 mmol), 2-chloro-3-fluoronitrobenzene (22.2; 126.2 mmol), cesium carbonate (25.4 g;126.2 mmol) and dry DMSO (300 mL) were added to a nitrogen-protected round-bottomed flask and allowed to react for 20H at 100℃with stirring; the reaction mixture was cooled to room temperature, the mixture was extracted with toluene, the organic phase was collected, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by silica gel column chromatography using toluene/n-heptane as eluent gave intermediate a1-1 (30.7 g; 59%)
Referring to the synthesis of intermediate a1-1, using reactant A of Table 1 below in place of 12H-benzofuran [3,2-a ] carbazole, the intermediate compounds shown in the following table were synthesized:
TABLE 1
Figure BDA0003109899300000292
Synthesis of intermediate a 1-2:
Figure BDA0003109899300000301
adding the intermediate a1-1 (35.5 g;86.0 mmol), cesium carbonate (84.1 g;258 mmol) and DMAC (500 mL) into a round-bottomed flask, stirring and heating to 140 ℃ under nitrogen protection, dividing water for half an hour, then reducing the temperature to 80 ℃ and adding tricyclohexylphosphine fluoroborate (4.8 g;12.9 mmol) and palladium acetate (1.5 g;6.9 mmol), stirring and heating to 140 ℃ for reaction for 16 hours; the reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; purification of the crude product by column chromatography on silica gel using methylene chloride/n-heptane as eluent gives intermediate a1-2 (17.2 g; 53%).
Referring to the synthesis of intermediate a1-2, using reactant C in Table 2 below in place of intermediate a1-1, the intermediate compounds shown in Table 2 below were synthesized:
TABLE 2
Figure BDA0003109899300000302
Synthesis of intermediate a 1:
Figure BDA0003109899300000303
/>
intermediate a1-2 (23.6 g;62.7 mmol), triphenylphosphine (41.1 g;156.8 mmol), o-dichlorobenzene (250 mL) were added to the flask, heated to 175℃under nitrogen and stirred for 36 hours; cooling to room temperature, washing the reaction solution with water, separating the solution, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under high temperature and reduced pressure to obtain crude product; purification of the crude product by silica gel column chromatography using a dichloromethane/n-heptane system afforded intermediate a1 (15.1 g, 70%) as a white solid.
Referring to the synthesis of intermediate a1, the following reactant D in Table 3 was substituted for intermediates a1-2 to synthesize the intermediates shown in Table 3 below:
TABLE 3 Table 3
Figure BDA0003109899300000304
Figure BDA0003109899300000311
synthesisofSM-a-1:
Figure BDA0003109899300000312
intermediate a1 (5.0 g;14.5 mmol), p-bromoiodobenzene (4.9 g;17.4 mmol), tris (dibenzylideneacetone) dipalladium (0.27 g;0.29 mmol), tri-tert-butylphosphine (0.12 g;0.58 mmol), sodium tert-butoxide (2.09 g;21.8 mmol) and xylene (100 mL) were added to a round bottom flask and reacted under nitrogen at 135℃for 16 h with stirring; cooling to room temperature, washing the reaction solution with water, separating the reaction solution, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purificationofthecrudeproductbysilicagelcolumnchromatographyusingdichloromethane/n-heptaneaseluentgaveSM-A-1(3.6g,55%)
referringtothesynthesisofSM-a-1,thefollowingintermediatecompoundshownintable4wassynthesizedusingreactanteinsteadofintermediatea1andreactantfinsteadofp-bromoiodobenzeneintable4below:
TABLE 4 Table 4
Figure BDA0003109899300000313
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Figure BDA0003109899300000321
/>
Figure BDA0003109899300000331
Synthesis of SM-B-1:
Figure BDA0003109899300000332
into the reaction flask were charged 3-aminodibenzofuran (5 g,27.3 mmol), SM1 (8.4 g,27.3 mmol), tris (dibenzylideneacetone) dipalladium (0.25 g,0.27 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.26 g,0.55 mmol), sodium t-butoxide (3.9 g,41.9 mmol) and toluene solvent (50 mL), and the mixture was heated to 110℃under nitrogen atmosphere and stirred under reflux for 8 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane (50 mL) and water (50 mL) and washed with water 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give SM-B-1 (7.1 g, yield 63%).
Referring to the synthesis of intermediate SM-B-1, using reactant W instead of 3-aminodibenzofuran and reactant Q instead of SM1 in table 5 below, the intermediate compound SM-B-X shown in table 5 below was synthesized:
TABLE 5
Figure BDA0003109899300000341
Synthesis of Compound A-1:
Figure BDA0003109899300000342
SM-A-1(5g,10.0mmol),diphenylamine(1.7g,10.0mmol),tris(dibenzylideneacetone)dipalladium(0.09g,0.1mmol),2-dicyclohexylphosphine-2',6'-dimethoxy-biphenyl(0.08g,0.2mmol),sodiumt-butoxide(1.4g,15.0mmol)andtoluenesolvent(100mL)werechargedintothereactionflask,andthemixturewasheatedto110℃undernitrogenatmosphere,andheatedunderrefluxwithstirringfor8hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water and washed with water 3 times, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was removed under reduced pressure, and the crude product was purified by recrystallization using a dichloromethane/n-heptane system to give A1 (4.1 g, yield 70%).
referringtothesynthesisofcompoundA1,thecompoundsshownintable6belowweresynthesizedusingreactantXinsteadofSM-a-1andreactantyinsteadofdiphenylamineintable6below:
TABLE 6
Figure BDA0003109899300000351
/>
Figure BDA0003109899300000361
/>
Figure BDA0003109899300000371
/>
Figure BDA0003109899300000381
/>
Figure BDA0003109899300000391
/>
Figure BDA0003109899300000401
/>
Figure BDA0003109899300000411
/>
Figure BDA0003109899300000421
The partial compound spectra data are shown in Table 7 below
TABLE 7
A1 m/z＝588.2[M+H] + A3 m/z＝638.2[M+H] +
A15 m/z＝714.3[M+H] + A23 m/z＝738.3[M+H] +
A37 m/z＝714.3[M+H] + A55 m/z＝829.3[M+H] +
A63 m/z＝829.3[M+H] + A69 m/z＝780.3[M+H] +
A78 m/z＝830.3[M+H] + A85 m/z＝846.3[M+H] +
A91 m/z＝756.2[M+H] + B4 m/z＝664.2[M+H] +
B33 m/z＝878.3[M+H] + B46 m/z＝866.3[M+H] +
B75 m/z＝856.3[M+H] + C4 m/z＝678.2[M+H] +
C19 m/z＝770.2[M+H] + C42 m/z＝856.3[M+H] +
D1 m/z＝638.2[M+H] + D10 m/z＝688.3[M+H] +
D13 m/z＝664.2[M+H] + D20 m/z＝780.3[M+H] +
D41 m/z＝826.3[M+H] + D42 m/z＝764.3[M+H] +
D43 m/z＝776.4[M+H] + D44 m/z＝681.3[M+H] +
D45 m/z＝846.3[M+H] + D46 m/z＝782.2[M+H] +
D47 m/z＝804.3[M+H] + A56 m/z＝816.3[M+H] +
D38 m/z＝820.2[M+H] + D48 m/z＝862.2[M+H] +
D49 m/z＝790.3[M+H] +
The nuclear magnetic data of a part of the compounds are shown in Table 8 below
TABLE 8
Figure BDA0003109899300000422
Preparation and performance evaluation of organic electroluminescent devices
Example 1
Red organic electroluminescent device
Example 1
The ITO thickness is equal to
Figure BDA0003109899300000423
Is cut into a size of 40mm by 0.7mm, and a test substrate having a cathode, an anode and an insulating layer pattern is prepared by using a photolithography process, and ultraviolet ozone and O are used 2 :N 2 The plasma is surface treated to remove surface particles and to increase the work function of the anode.
PtPC is vacuum evaporated on a substrate by PVD method to form a film with a thickness of
Figure BDA0003109899300000424
Is vapor-deposited with HT-01 to form a layer with a thickness of +.>
Figure BDA0003109899300000426
Is provided.
Vapor deposition thickness on hole transport layer
Figure BDA0003109899300000425
HT-02, a hole assist layer formed.
On the hole-assist layer(s),compound A1: compound RH-N: ir (piq) 2 (acac) at 49%:49%: co-evaporation is carried out at a ratio of 2% (evaporation rate) to form
Figure BDA0003109899300000435
An organic electroluminescent layer (red light-emitting layer).
Mixing ET-01 and LiQ in a weight ratio of 1:1 and evaporating to form
Figure BDA0003109899300000433
A thick electron transport layer, yb is evaporated on the electron transport layer to form +.>
Figure BDA0003109899300000436
Then magnesium and silver are mixed with 1:10, vacuum vapor deposition on the electron injection layer to form + >
Figure BDA0003109899300000432
Is provided.
Vapor deposition on the cathode
Figure BDA0003109899300000434
And forming an organic coating layer (CPL) on the CP-01 with the thickness to finish the manufacture of the organic light-emitting device.
Examples 2 to 31:
in forming the red light-emitting layer, an organic electroluminescent device was fabricated by the same method as in example 29, except that the compound A1 in example 1 was replaced with the compound shown in table 10.
Comparative example 1:
referring to table 10, an organic electroluminescent device was prepared in the same manner as in example 1, substituting compound 1 for compound A1 in example 1.
Comparative example 2:
referring to table 10, an organic electroluminescent device was prepared in the same manner as in example 1, substituting compound 2 for compound A1 in example 1.
In examples 2 to 31 and comparative examples 1 to 2, the structural formulas of the respective materials used are shown in the following Table 9:
TABLE 9
Figure BDA0003109899300000431
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The IVL performance of the device was analyzed under the conditions of T95 lifetime at 15mA/cm 2 The results are shown in Table 10 below:
table 10
Figure BDA0003109899300000441
As can be seen from table 10 above, when the compounds in this application were used as the hole-type host materials in the red-light bi-host materials, the current efficiency was improved by at least 13.5% and the lifetime was improved by at least 24.6% as compared to comparative examples 1-2.
When the compound in the present application is used as a hole-type host material in a red-light bi-host material, the device has improved efficiency and lifetime compared to comparative example 1; the reason for this may be that the compound in the present application has higher hole mobility than the compound 1, thereby improving the carrier recombination efficiency. Compared with comparative example 2, the lifetime of the organic electroluminescent device is obviously improved when the compound is used as the organic electroluminescent device, and the reason is probably that the compound is more stable in the molecular structure of the parent nucleus.
The application uses a special carbazole condensed ring derivative structure as a core, and combines with triarylamine groups, so that molecules have high hole mobility, proper T1 energy level (triplet state energy level) and stable chemical structure; the material is suitable for being used as a cavity type main body material in a red light double main body material, so that the red light device has improved luminous efficiency and service life.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the application following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the application pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.

Claims (8)

1. An organic compound having a structure represented by formula 1:
Figure FDA0004213606940000011
wherein X is selected from O or S;
l is selected from a single bond, a substituted or unsubstituted phenylene group;
L 1 、L 2 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 fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazole group;
said L, L 1 、L 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
L 3 selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene;
the L is 3 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
Ar 1 、Ar 2 each independently 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 phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and combinations thereof Unsubstituted dibenzothienyl;
the Ar is as follows 1 、Ar 2 Each of the substituents of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, tridentate methyl;
each R is 1 、R 2 、R 3 And R is 4 Each independently selected from deuterium, halogen group, cyano, aryl group having 6-20 carbon atoms, heteroaryl group having 5-20 carbon atoms, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms;
n 1 represents a substituent R 1 Number n of (n) 1 Selected from 0;
n 2 represents a substituent R 2 Number n of (n) 2 Selected from 0;
n 3 represents a substituent R 3 Number n of (n) 3 Selected from 0;
n 4 represents a substituent R 4 Number n of (n) 4 Selected from 0.
2. The organic compound according to claim 1, wherein L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted group V, the unsubstituted group V being selected from the group consisting of:
Figure FDA0004213606940000012
Figure FDA0004213606940000021
wherein,,
Figure FDA0004213606940000022
represents a chemical bond; the substituted group V has one or more substituents thereon, each of the substituentsIndependently selected from deuterium, cyano, fluoro, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the number of substituents of V is greater than 1, the substituents may be the same or different.
3. An organic compound having a structure represented by formula 1:
Figure FDA0004213606940000023
wherein X is selected from O or S;
l is selected from a single bond, a substituted or unsubstituted phenylene group;
L 1 、L 2 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 fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazole group;
said L, L 1 、L 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
L 3 selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene;
the L is 3 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl;
the Ar is as follows 1 、Ar 2 Each independently selected from the group consisting of substituted or unsubstituted groups W, wherein unsubstituted groups W are selected from the group consisting of:
Figure FDA0004213606940000024
Figure FDA0004213606940000031
wherein,,
Figure FDA0004213606940000032
represents a chemical bond; the substituted group W has one or more substituents thereon, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, triphenylsilyl, trimethylsilyl, trifluoromethyl, tridentate methyl; when the number of substituents of W is greater than 1, each substituent is the same or different.
4. An organic compound, wherein the organic compound is selected from the group consisting of:
Figure FDA0004213606940000033
Figure FDA0004213606940000041
Figure FDA0004213606940000051
Figure FDA0004213606940000061
Figure FDA0004213606940000071
Figure FDA0004213606940000081
Figure FDA0004213606940000091
Figure FDA0004213606940000101
/>
Figure FDA0004213606940000111
/>
Figure FDA0004213606940000121
/>
Figure FDA0004213606940000131
/>
Figure FDA0004213606940000141
/>
Figure FDA0004213606940000151
/>
Figure FDA0004213606940000161
/>
Figure FDA0004213606940000171
/>
Figure FDA0004213606940000181
5. an organic electroluminescent device, characterized in that it comprises an anode, a cathode, and at least one functional layer between the anode and the cathode, the functional layer comprising the organic compound according to any one of claims 1 to 4.
6. The organic electroluminescent device of claim 5, wherein the functional layer comprises an organic electroluminescent layer comprising the organic compound.
7. The organic electroluminescent device of claim 5, wherein the organic electroluminescent device is a red organic electroluminescent device.
8. An electronic device comprising the organic electroluminescent device as claimed in any one of claims 5 to 7.
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