CN116143703A - Organic compound, and electronic component and electronic device including the same - Google Patents

Organic compound, and electronic component and electronic device including the same Download PDF

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CN116143703A
CN116143703A CN202310181809.8A CN202310181809A CN116143703A CN 116143703 A CN116143703 A CN 116143703A CN 202310181809 A CN202310181809 A CN 202310181809A CN 116143703 A CN116143703 A CN 116143703A
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张林伟
张鹤鸣
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Shaanxi Lighte Optoelectronics Material Co Ltd
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • Y02E10/00—Energy generation through renewable energy sources
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    • Y02E10/549—Organic PV cells

Abstract

The present application relates to an organic compound, and an electronic component and an electronic device including the same. The structural formula of the organic compound of the present application comprisesThe structure shown in the formula I can be used for remarkably improving the performance of an organic electroluminescent device by applying the organic compound to the organic electroluminescent device.
Figure DDA0004104161330000011

Description

Organic compound, and electronic component and electronic device including the same
Technical Field
The application belongs to the technical field of organic materials, and particularly relates to an organic compound, an electronic element comprising the same and an electronic device.
Background
At present, research on organic electroluminescent materials has been widely conducted in academia and industry, and a great number of organic electroluminescent materials with excellent properties have been developed. In general, the direction of the future organic electroluminescent devices is to develop white light devices and full-color display devices with high efficiency, long lifetime and low cost, but the industrialization process of the technology still faces a number of key problems. Therefore, the compound is designed and searched to be a stable and efficient compound which is used as a novel material of the organic electroluminescent device to overcome the defects of the organic electroluminescent device in the practical application process, and is an important point in the research work of the material of the organic electroluminescent device and a research trend in the future. 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.
In general, the electron transport material has poor stability and low transport efficiency, and when used in an organic electroluminescent device, the electron transport material cannot truly balance hole electron transport, so that the luminous efficiency of the device is reduced, and the service life of the device is shortened.
At present, although a large number of organic electroluminescent materials with excellent performance have been developed, it is still necessary to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
In view of the foregoing problems of the prior art, an object of the present application is to provide an organic compound, an electronic component and an electronic device including the same, which can be used in an electronic component to improve performance of the electronic component.
A first aspect of the present application provides an organic compound having a structure represented by formula I:
Figure BDA0004104161300000011
wherein X is 1 、X 2 And X 3 Each independently is C (H) or N, and X 1 -X 3 At least one of which is N;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
R 1 and R is 2 Identical or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms; or any two adjacent R 1 Are connected to each other to form a ring, or any two adjacent R 2 Are connected with each other to form a ring;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
Ar 1 、Ar 2 、L、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, deuterated aryl group with 6-12 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms; optionally Ar 1 Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring; optionally Ar 2 Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring.
A second aspect of the present application provides an electronic component comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
A third aspect of the present application provides an electronic device comprising the electronic component of the second aspect.
The organic compound takes a specific condensed spiro structure as a core structure, and the structure has a large conjugated system and simultaneously has larger rigidity and higher carrier transmission efficiency. Further, by introducing a substituted electron-deficient nitrogen-containing six-membered heteroaryl group at one side of the spiro structure, the formed organic compound has higher electron transfer characteristics or hole blocking characteristics, and when the organic compound is applied to an organic electroluminescent device, the prepared organic electroluminescent device has good photoelectric properties, and the luminous efficiency and the service life of the device are improved.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
321. Hole transport layer 322, hole assist layer 330, organic light emitting layer 340, electron transport layer
350. Electron injection layer 400 and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many 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 exemplary 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 a first aspect, the present application provides an organic compound having a structure represented by formula I:
Figure BDA0004104161300000021
wherein X is 1 、X 2 And X 3 Each independently is C (H) or N, and X 1 -X 3 At least one of which is N;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
R 1 and R is 2 Identical or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms; or any two adjacent R 1 Are connected to each other to form a ring, or any two adjacent R 2 Are connected with each other to form a ring;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
Ar 1 、Ar 2 、L、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, deuterated aryl group with 6-12 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms; optionally Ar 1 In (a) and (b)Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring; optionally Ar 2 Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: any two adjacent substituents form a ring, and any two adjacent substituents each independently exist, and do not form a ring. Any two adjacent atoms can include two substituents on the same atom, and can also include two adjacent atoms with one substituent respectively; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated spiro 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.
In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently" are interchangeable, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,
Figure BDA0004104161300000031
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 group having a substituent Rc or an aryl group having no substituent. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl or the like. The number of substituents may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3,4, 5, 6, etc.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms.
The hydrogen atoms in the structures of the compounds of the present application include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
"D" in the structural formula of the compound of the present application represents deuteration.
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. That is, unless otherwise indicated, two or more aromatic groups linked by carbon-carbon bonds may also be considered aryl groups herein. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,
Figure BDA0004104161300000032
A base, etc.
As used herein, "arylene" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.
In the present application, terphenyl includes
Figure BDA0004104161300000041
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group may be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.
In this application, the fluorenyl group may be substituted with 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be:
Figure BDA0004104161300000042
and the like, but is not limited thereto.
In the present application, as L, L 1 、L 2 、Ar 1 And Ar is a group 2 Aryl groups of substituents of (a) such as, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.
In the present application heteroaryl means a monovalent aromatic ring or derivative thereof containing 1,2, 3,4, 5 or 6 heteroatoms in the ring, which may be one or more 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, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, reference to heteroarylene refers to a divalent or multivalent radical formed by the further loss of one or more hydrogen atoms from the heteroaryl group.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may be selected from 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 12 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 12 carbon atoms.
In the present application, as L, L 1 、L 2 、Ar 1 And Ar is a group 2 Heteroaryl groups of substituents of (a) such as, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl.
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, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
Specific examples of deuterated aryl groups herein include, but are not limited to, deuterated phenyl groups.
In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered ring. By 3-15 membered ring is meant a cyclic group having 3-15 ring atoms. The 3-15 membered ring is, for example, cyclopentane, cyclohexane, fluorene ring, benzene ring, etc.
In the present application,
Figure BDA0004104161300000051
refers to chemical bonds that interconnect other groups.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring system
Figure BDA0004104161300000052
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 BDA0004104161300000053
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 BDA0004104161300000054
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means includes any of the possible linkages as shown in formula (Y-1) -formula (Y-7).
Figure BDA0004104161300000055
Alternatively, X 1 -X 3 Two or three of which are N.
Alternatively, X 1 Selected from N, X 2 Selected from C or N, X 3 Selected from N.
Alternatively, X 1 Selected from N, X 3 Selected from C or N, X 2 Selected from N.
Alternatively, formula I is selected from structures represented by formulas I-1 through I-3 below:
Figure BDA0004104161300000061
alternatively, formula I is selected from the structures shown in formulas I-a through I-l below:
Figure BDA0004104161300000062
in one embodiment of the present application, R 1 、R 2 And R is 3 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, or phenyl.
In the present applicationIn one embodiment of (1), ar 1 And Ar is a group 2 And are identical or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 Each of the substituents in (a) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, deuterated phenyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 12 to 18 carbon atoms; optionally in Ar 1 、Ar 2 Any two adjacent substituents form a 5-13 membered ring.
Alternatively, ar 1 And Ar is a group 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 BDA0004104161300000071
wherein the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl.
Alternatively, ar 1 And Ar is a group 2 Each independently selected from the group consisting of:
Figure BDA0004104161300000072
further alternatively, ar 1 And Ar is a group 2 Each independently selected from the following groups:
Figure BDA0004104161300000073
/>
Figure BDA0004104161300000081
in some embodiments, L, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 14 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, or 14 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Optionally, the L, L 1 And L 2 Each substituent of (2) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, deuterated phenyl, aryl having 6 carbon atoms or heteroaryl having 5 to 12 carbon atoms.
In some embodiments, L, L 1 And L 2 And are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophene group, and a substituted or unsubstituted dibenzofuran group.
Optionally L, L 1 And L 2 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl or naphthyl.
In some embodiments, L, L 1 And L 2 Identical or different and are each independently selected from the group consisting of single bonds or:
Figure BDA0004104161300000082
/>
Figure BDA0004104161300000091
in some embodiments, L, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
Figure BDA0004104161300000092
in some embodiments of the present invention, in some embodiments,
Figure BDA0004104161300000093
each independently selected from the group consisting of:
Figure BDA0004104161300000094
/>
Figure BDA0004104161300000101
optionally, the organic compound is selected from the group consisting of the following compounds.
Figure BDA0004104161300000102
/>
Figure BDA0004104161300000111
/>
Figure BDA0004104161300000121
/>
Figure BDA0004104161300000131
/>
Figure BDA0004104161300000141
/>
Figure BDA0004104161300000151
/>
Figure BDA0004104161300000161
/>
Figure BDA0004104161300000171
/>
Figure BDA0004104161300000181
/>
Figure BDA0004104161300000191
/>
Figure BDA0004104161300000201
In a second aspect, the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described herein.
Optionally, the electronic component is an organic electroluminescent device.
In one embodiment of the present application, the structure of the organic electroluminescent device is shown in fig. 1, and includes an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes an electron transport layer 340, the electron transport layer 340 comprising an organic compound as described herein.
Alternatively, the functional layer 300 includes a hole transport layer 321 between the anode and the organic light emitting layer. The hole transporting material may be selected from triarylamine compounds or other types of compounds, and may be selected by those skilled in the art with reference to the prior art. For example, the hole transport layer 321 is made of a material selected from the group consisting of the following compounds.
Figure BDA0004104161300000211
In one embodiment of the present application, the material of hole transport layer 321 comprises NPB.
In one embodiment of the present application, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a hole auxiliary layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
In this application, anode 100 includes an anode material that is optionally 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 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. Optionally, a transparent electrode comprising Indium Tin Oxide (ITO) as anode is included.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 is selected from, for example, the following compounds or any combination thereof;
Figure BDA0004104161300000212
Figure BDA0004104161300000221
in one embodiment of the present application, hole injection layer 310 is comprised of HAT-CN.
Optionally, electron blocking layer 322 includes one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds, as not particularly limited in this application. For example, in some embodiments of the present application, electron blocking layer 322 is formed from compound EB-1
Figure BDA0004104161300000222
Composition is prepared.
Optionally, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting 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 host material of the organic light emitting layer 330 may include a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. The host material of the organic light emitting layer 330 may be one compound, a combination of two or more compounds.
In one embodiment of the present application, the host material of the organic light emitting layer 330 is BH-1
Figure BDA0004104161300000223
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. Guest materials are also known as doping materials or dopants. Specific examples of such dopants include but are not limited to,
Figure BDA0004104161300000224
Figure BDA0004104161300000231
in some embodiments of the present application, the guest material of the organic light emitting layer 330 is BD-1.
In this application, cathode 200 includes 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, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, electron injection layer 350 comprises Yb.
A third aspect of the present application provides an electronic device comprising an electronic component as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic method of the organic compound of the present application is specifically described below with reference to synthetic examples, but the present application is not limited thereto.
Synthesis example
1. Synthesis of intermediates
1. Synthesis of intermediate IM a1-dX
Taking IM a1-d1 as an example, the synthesis of IM a1-dX is described:
Figure BDA0004104161300000232
(1) 1, 8-Dilithium naphthalene (120 g,856.90 mmol) and diethyl ether were added into a three-necked flask, the system was cooled to-10 ℃ to 10 ℃, rhodium tetracarbonyl dichloride (333.14 g,856.90 mmol) was added, the reaction was carried out at-10 ℃ to 10 ℃ for 2 hours, the reaction was naturally carried out at room temperature for 6 hours, the reaction solution was extracted with ethyl acetate and water, the organic phase was dried with anhydrous magnesium sulfate, the organic layer was concentrated under reduced pressure to obtain a crude product, and the crude product was crystallized with dichloromethane/n-heptane to obtain a white solid IM a1-a0 (37.5 g, yield 31.0%).
Figure BDA0004104161300000233
(2) 2-bromo-4-chloroiodobenzene (80.00 g,252.09 mmol), phenylboronic acid (30.74 g,252.09 mmol), potassium carbonate (69.68 g,504.18 mmol), tetrabutylammonium bromide (8.13 g,25.21 mmol), toluene (400 mL), ethanol (240 mL) and deionized water (160 mL) were added to a three-necked flask, stirred under nitrogen for 15min, tetrakis (triphenylphosphine) palladium (2.91 g,2.52 mmol) was added and warmed to 75℃to 80℃and stirred for 24 hours; the reaction solution was cooled to room temperature, washed with water several times to neutrality, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, followed by recrystallization from methylene chloride/n-heptane to give IM a1-a1 (35.6 g, yield 52.8%) as a white solid.
Figure BDA0004104161300000241
(3) IM a1-a1 (34.0 g,127.08 mmol) and THF (204 mL) are added into a 500mL round bottom flask, the system is cooled to-90 ℃ to-78 ℃, n-butyllithium (2 mol/L;76.25mL,152.50 mmol) tetrahydrofuran solution is added dropwise, the reaction is carried out for 1h at-90 ℃ to-78 ℃, then IM a1-a0 (35.62 g,127.08 mmol) is dissolved by THF (142 mL) and then slowly added dropwise into the reaction system, the reaction is carried out for 1h at-78 ℃ to-90 ℃, and then the reaction is naturally carried out to room temperature and stirred for 6h; water (200 mL) was added to the reaction system to terminate the reaction, and extraction was performed with ethyl acetate and water, and the organic layer was concentrated under reduced pressure to give a crude product, which was recrystallized from acetonitrile to give IM a1-b1 (33.5 g, yield 56.2%).
Figure BDA0004104161300000242
(4) IM a1-b1 (33.0 g,70.37 mmol) was placed in a 500mL round bottom flask with acetic acid (330 mL), sulfuric acid (98 wt%,1 mL), the temperature was raised to 75℃for 3h, solid precipitation was carried out as the reaction proceeded, the system was cooled to room temperature after the reaction was completed, then filtration was carried out, the filter cake was rinsed with water and ethanol multiple times to obtain a crude product, and the crude product was crystallized with dichloromethane/n-heptane to obtain IM a1-c1 (29.3 g, yield 92.3%).
Figure BDA0004104161300000243
(5) IM a1-c1 (29.0 g,64.31 mmol), pinacol biborate (16.33 g,64.31 mmol), tris (dibenzylideneacetone) dipalladium (0.64 g,0.59 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.61 g,1.29 mmol), potassium acetate (12.62 g,128.61 mmol) and 1, 4-dioxane (290 mL) were added to a three-necked round bottom flask, heated to 80℃under nitrogen and stirred for 4h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a toluene system to give solid IM a1-d1 (26.1 g, yield 74.8%).
Referring to the synthesis method of IM a1-d1, other IM a1-dX listed in Table 1 was synthesized, except that raw material 1 was used in place of 2-bromo-4-chloroiodobenzene in step (2), raw material 2 was used in place of phenylboronic acid in step (2), raw material 3 was used in place of IM a1-a1 in step (3), and the main raw materials used and the synthesized IM a1-dX were as shown in Table 1, with the final step yields.
TABLE 1
Figure BDA0004104161300000244
/>
Figure BDA0004104161300000251
2. Synthesis of intermediate IM a1-d-bX
The synthesis of IM a1-d-bX is illustrated with IM a1-d-b 1:
Figure BDA0004104161300000252
(1) IM a1-d1 (5.50 g,10.14 mmol), 4-chlorobromobenzene (1.94 g,10.14 mmol), potassium carbonate (2.80 g,20.28 mmol), tetrabutylammonium bromide (0.65 g,2.03 mmol), toluene (45 mL), ethanol (15 mL) and deionized water (15 mL) were added to a three-necked flask, stirred under nitrogen for 15min, then tetrakis (triphenylphosphine) palladium (0.12 g,0.10 mmol) was added and the temperature was raised to 75℃to 80℃and stirred for 6h; the reaction solution was cooled to room temperature, washed with water several times to neutrality, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized from methylene chloride/n-heptane to give IM a1-d-a1 (3.65 g, yield 68.3%) as a white solid.
Figure BDA0004104161300000261
(2) IM a1-d-a1 (3.5 g,6.64 mmol), pinacol biborate (1.69 g,6.64 mmol), tris (dibenzylideneacetone) dipalladium (0.06 g,0.07 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.06 g,0.13 mmol), potassium acetate (1.30 g,13.28 mmol) and 1, 4-dioxane (40 mL) were added to a three-necked round bottom flask, heated to 80℃under nitrogen and stirred for 4h; cooling to room temperature, washing the reaction solution with water, adding magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was purified by recrystallization using a toluene system to give solid IM a1-d-b1 (2.85 g, yield 69.4%).
Other IM a1-d-bX was synthesized by referring to the synthesis method of IM a1-d-b1, except that starting material 4 was used in place of IM a1-dX in step (1), starting material 5 was used in place of 4-chlorobromobenzene, and the main starting materials used and the synthesized IM a1-d-bX and final step yields are shown in Table 2.
TABLE 2
Figure BDA0004104161300000262
/>
Figure BDA0004104161300000271
3. Synthesis of intermediate IM a1-X
Taking IM a1-1 as an illustration of the synthesis of IM a1-X
Figure BDA0004104161300000272
IM a1-d1 (20.00 g,36.87 mmol), cyanuric chloride (6.80 g,36.87 mmol), potassium carbonate (10.19 g,73.73 mmol), tetrabutylammonium bromide (1.19 g,3.69 mmol), toluene (104 mL), ethanol (26 mL) and deionized water (26 mL) were added to a three-necked flask, stirred under nitrogen for 15min, then tetrakis (triphenylphosphine) palladium (0.43 g,0.37 mmol) was added and the temperature was raised to 75℃to 80℃and stirred for 5 h; the reaction solution was cooled to room temperature, washed with water several times to neutrality, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, followed by recrystallization from dichloroethane/n-heptane to give IM a1-1 as a white solid (12.15 g, yield 58.4%).
Other IM a1-X was synthesized with reference to the synthesis of IM a1-1, except that starting material 5 was used in place of IM a1-d1, starting materials 5 and IM a1-X and their yields are shown in Table 3.
TABLE 3 Table 3
Figure BDA0004104161300000273
/>
Figure BDA0004104161300000281
/>
Figure BDA0004104161300000291
/>
Figure BDA0004104161300000301
Synthesis of Compounds
Synthesis example 1: synthesis of Compound 1-1
Figure BDA0004104161300000302
(1) IM a1-1 (12 g,21.26 mmol), 4-fluorobenzeneboronic acid (1.89 g,21.26 mmol), potassium carbonate (5.88 g,42.52 mmol), tetrabutylammonium bromide (0.69 g,2.13 mmol), toluene (64 mL), ethanol (24 mL) and deionized water (24 mL) were added to a three-necked flask, stirred under nitrogen for 15min, and then tetrakis (triphenylphosphine) palladium (0.25 g,0.21 mmol) was added and heated to 75℃to 80℃and stirred for 8 hours; the reaction solution was cooled to room temperature, washed with water several times to neutrality, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, and recrystallized from methylene chloride/n-heptane to give IMA1-a1 (8.2 g, yield 61.8%) as a white solid.
Figure BDA0004104161300000303
(2) IMA1-a1 (8.0 g,12.82 mmol), 4-fluorobenzeneboronic acid (1.79 g,12.82 mmol), potassium carbonate (3.54 g,25.64 mmol), tetrabutylammonium bromide (0.41 g,0.1.28 mmol), toluene (64 mL), ethanol (16 mL) and deionized water (16 mL) were added to a triple solutionIn the neck flask, stirring for 15min under the protection of nitrogen, adding tetrakis (triphenylphosphine) palladium (0.15 g,0.13 mmol) and heating to 75-80 ℃ and stirring for 12 h; the reaction solution was cooled to room temperature, washed with water several times to neutrality, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and toluene was used to slurry to obtain a white solid, namely, compound 1-1 (5.6 g, yield 63.9%). Mass spectrometry: m/z=684.2 [ m+h ]] + ；
The compounds listed in Table 4 were synthesized by referring to the method for the compound 1-1, except that IM a1-1 in the step (1) was replaced with the raw material 6, 4-fluorobenzeneboronic acid in the step (1) was replaced with the raw material 7, 4-fluorobenzeneboronic acid in the step (2) was replaced with the raw material 8, and the main raw materials used, the synthesized compounds and the final step yields and mass spectrum results thereof were shown in Table 4.
TABLE 4 Table 4
Figure BDA0004104161300000304
/>
Figure BDA0004104161300000311
/>
Figure BDA0004104161300000321
/>
Figure BDA0004104161300000331
/>
Figure BDA0004104161300000341
/>
Figure BDA0004104161300000351
The compound nuclear magnetic data are shown in table 5:
TABLE 5
Figure BDA0004104161300000352
Example 1
The embodiment provides an organic electroluminescent device, which is prepared by the following steps:
the anode was prepared by the following procedure: the material coated with three layers of ITO/Ag/ITO (thickness is
Figure BDA0004104161300000361
The ITO substrate of (C) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a photolithography step was used to prepare an experimental substrate having cathode, anode and insulating layer patterns, and ultraviolet ozone and O were used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum vapor deposition of HAT-CN on experimental substrate (anode) to form a thickness of
Figure BDA0004104161300000362
Is then vacuum evaporated on the hole injection layer to form NPB with a thickness of +.>
Figure BDA0004104161300000363
Is provided.
Vacuum evaporating EB-1 on the hole transport layer to form a film with a thickness of
Figure BDA0004104161300000364
Is a barrier to electrons.
Next, on the electron blocking layer, compound BH-1 (doping host) and compound BD-1 (doping guest) were mixed in 98%: co-evaporation is carried out at a ratio of 2% to form a film with a thickness of
Figure BDA0004104161300000365
Is (EML)
In the light-emitting layerIn the above process, the compound 1-1 and LiQ are mixed in a thickness ratio of 1:1 and vapor deposited to form
Figure BDA0004104161300000366
A thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>
Figure BDA0004104161300000367
Then magnesium (Mg) and silver (Ag) are mixed in a vapor deposition rate ratio of 1:10, and vacuum vapor deposited on the electron injection layer to form a film having a thickness of +.>
Figure BDA0004104161300000368
Is provided.
In addition, the thickness of the vacuum evaporation on the cathode is
Figure BDA0004104161300000369
And thus the green organic electroluminescent device is manufactured.
Example 2-example 35:
an organic electroluminescent device was prepared by the same method as in example 1, except that the compound 1-1 in example 1 was replaced with the compound in table 1 when preparing an electron transport layer.
Comparative example 1-comparative example 3
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound 1-1 in example 1 was replaced with the compound in table 1 when preparing an electron transport layer.
Wherein, in preparing the organic electroluminescent device, the structures of the respective materials used in the comparative example and the examples are as follows:
the main material structures used in the above examples and comparative examples are shown in table 6.
TABLE 6
Figure BDA00041041613000003610
/>
Figure BDA0004104161300000371
The green organic electroluminescent devices prepared in examples 1 to 35 and comparative examples 1 to 3 were subjected to performance test, particularly at 10mA/cm 2 IVL data (operating voltage, external quantum efficiency, color coordinates) of the device, T 95 Life at 15mA/cm 2 The test results are shown in table 7 below.
TABLE 7 results of Performance test of blue organic electroluminescent devices
Figure BDA0004104161300000372
/>
Figure BDA0004104161300000381
Referring to Table 7 above, it can be seen that the organic electroluminescent devices of examples 1 to 35 have significantly improved performance over the organic electroluminescent devices of comparative examples 1 to 3. Mainly characterized in that the working voltage of the device is slightly reduced, the external quantum efficiency is at least improved by 15.7%, and T 95 The lifetime is improved by at least 16.9%. It can be seen that the application of the organic compound to the electron transport layer of the organic electroluminescent device can significantly improve the external quantum efficiency and T of the organic electroluminescent device 95 And (5) service life.
The preferred embodiments of the present application have been described in detail above, but the present application is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solutions of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application.

Claims (11)

1. An organic compound, characterized in that the organic compound has a structure represented by formula I:
Figure FDA0004104161280000011
wherein X is 1 、X 2 And X 3 Each independently is C (H) or N, and X 1 -X 3 At least one of which is N;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
R 1 and R is 2 Identical or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms; or any two adjacent R 1 Are connected to each other to form a ring, or any two adjacent R 2 Are connected with each other to form a ring;
n 1 r represents 1 And is selected from 0, 1,2, 3 or 4; when n is 1 When the number is greater than 1, any two R 1 The same or different;
n 2 r represents 2 And is selected from 0, 1,2, 3 or 4; when n is 2 When the number is greater than 1, any two R 2 The same or different;
Ar 1 、Ar 2 、L、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, deuterated aryl group with 6-12 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms; optionally Ar 1 Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring; optionally Ar 2 Any two adjacent substituents of (a) form a saturated or unsaturated 3-15 membered ring.
2. The organic compound according to claim 1, X 1 ～X 3 Two or three of which are N.
3. The organic compound according to claim 1, wherein R 1 、R 2 And R is 3 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, or phenyl.
4.Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms;
alternatively, ar 1 And Ar is a group 2 Each of the substituents in (a) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, deuterated phenyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 12 to 18 carbon atoms; optionally in Ar 1 、Ar 2 Any two adjacent substituents form a 5-13 membered ring.
5. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 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 FDA0004104161280000012
/>
Figure FDA0004104161280000021
wherein the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl.
6. The organic compound according to claim 1, wherein L, L 1 And L 2 And are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophene group, and a substituted or unsubstituted dibenzofuran group;
optionally L, L 1 And L 2 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, deuterated phenyl, phenyl or naphthyl.
7. The organic compound according to claim 1,
Figure FDA0004104161280000022
each independently selected from the group consisting of:
Figure FDA0004104161280000023
8. the organic compound according to claim 1, which is selected from the group consisting of:
Figure FDA0004104161280000031
/>
Figure FDA0004104161280000041
/>
Figure FDA0004104161280000051
/>
Figure FDA0004104161280000061
/>
Figure FDA0004104161280000071
/>
Figure FDA0004104161280000081
/>
Figure FDA0004104161280000091
/>
Figure FDA0004104161280000101
/>
Figure FDA0004104161280000111
/>
Figure FDA0004104161280000121
/>
Figure FDA0004104161280000131
9. an electronic component comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; characterized in that the functional layer comprises an organic compound according to any one of claims 1 to 8;
optionally, the electronic component is an organic electroluminescent device.
10. The electronic component of claim 9, wherein the functional layer comprises an electron transport layer comprising the organic compound.
11. Electronic device, characterized in that it comprises an electronic component according to claim 9 or 10.
CN202310181809.8A 2023-02-28 2023-02-28 Organic compound, and electronic component and electronic device including the same Pending CN116143703A (en)

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