CN113004289A - Organic compound, and electronic element and electronic device using same - Google Patents

Organic compound, and electronic element and electronic device using same Download PDF

Info

Publication number
CN113004289A
CN113004289A CN202110236134.3A CN202110236134A CN113004289A CN 113004289 A CN113004289 A CN 113004289A CN 202110236134 A CN202110236134 A CN 202110236134A CN 113004289 A CN113004289 A CN 113004289A
Authority
CN
China
Prior art keywords
group
carbon atoms
substituted
unsubstituted
independently selected
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN202110236134.3A
Other languages
Chinese (zh)
Other versions
CN113004289B (en
Inventor
马天天
杨雷
徐先彬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shaanxi Lighte Optoelectronics Material Co Ltd
Original Assignee
Shaanxi Lighte Optoelectronics Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shaanxi Lighte Optoelectronics Material Co Ltd filed Critical Shaanxi Lighte Optoelectronics Material Co Ltd
Publication of CN113004289A publication Critical patent/CN113004289A/en
Application granted granted Critical
Publication of CN113004289B publication Critical patent/CN113004289B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present application relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound has a structure formed by fusing formula 1 and formula 2 as shown in the specification, and represents a connection point of formula 1 and formula 2. The organic compounds of the present application can improve the performance of electronic components.
Figure DDA0002960227850000011
。

Description

Organic compound, and electronic element and electronic device using same
Technical Field
The present invention relates to the field of organic material technology, and in particular, to an organic compound, and an electronic element and an electronic device using the same.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
Taking an organic electroluminescent device as an example, the organic electroluminescent device generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the organic light emitting layer under the action of the electric field, holes on the anode side also move to the light emitting layer, the electrons and the holes are combined in the organic light emitting layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the organic light emitting layer emits light outwards.
The prior art discloses materials that can be used to produce light-emitting layers in organic electroluminescent devices. However, there is still a need to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide an organic compound that can be used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an electronic element and an electronic device using the same.
In order to achieve the above object, a first aspect of the present application provides an organic compound having a structure formed by fusing formula 1 with formula 2 as follows:
Figure BDA0002960227830000011
wherein formula 1 is fused to formula 2, and represents the point of attachment of formula 1 fused to formula 2;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L1、L2and L3The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
R1、R2and R3The same or different, and each is independently selected from deuterium, halogen group, alkyl group with 1-10 carbon atoms, naphthenic group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, aryl group with 6-30 carbon atoms and heteroaryl group with 3-30 carbon atoms;
n1represents R1Number of (2), n1Is 0, 1,2, 3 or 4, n1When greater than 1, any two R1The same or different;
n2represents R2Number of (2), n2Is 0, 1 or 2, n2When greater than 1, any two R2The same or different;
n3represents R3Number of (2), n3Is 0, 1,2, 3 or 4, n3When greater than 1, any two R3The same or different;
Ar1、Ar2and L1、L2And L3Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 9 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms.
A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to the first aspect of the present application;
preferably, the functional layer includes an organic light emitting layer including the organic compound;
more preferably, the organic light emitting layer includes a host material and a guest material, and the host material includes the organic compound.
A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.
The organic compound provided by the application is respectively connected with triazinyl and diphenyl fluorenyl through nitrogen atoms of indolocarbazole, and has a molecular structure shown by triazine-indolocarbazole-diphenyl fluorene; the molecular structure of the organic compound has high electron mobility and exciton energy transmission efficiency, and is suitable for being used as a main body material of a light-emitting layer in an organic electroluminescent device; the introduction of the large-volume functional group diphenyl fluorene group can promote the amorphous state of the molecular stack and further enhance the stability of the material structure, so that the service life of the device can be effectively prolonged when the material with the molecular structure is applied to a device light-emitting layer.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural diagram of an electronic device according to another 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 first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 341. a hole blocking layer; 340. an electron transport layer; 350. an electron injection layer; 400. a first electronic device; 500. a second electronic device.
Detailed Description
The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.
A first aspect of the present application provides an organic compound having a structure formed by fusing formula 1 as follows with formula 2:
Figure BDA0002960227830000031
wherein formula 1 is fused to formula 2, and represents the point of attachment of formula 1 fused to formula 2;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L1、L2and L3The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
R1、R2and R3The same or different, and each is independently selected from deuterium, halogen group, alkyl group with 1-10 carbon atoms, naphthenic group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, aryl group with 6-30 carbon atoms and heteroaryl group with 3-30 carbon atoms;
n1represents R1Number of (2), n1Is 0, 1,2, 3 or 4, n1When greater than 1, any two R1The same or different;
n2represents R2Number of (2), n2Is 0, 1 or 2, n2When greater than 1, any two R2The same or different;
n3represents R3Number of (2), n3Is 0, 1,2, 3 or 4, n3When greater than 1, any two R3The same or different;
Ar1、Ar2and L1、L2And L3Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 9 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, and a trialkylsilyl group having 3 to 12 carbon atoms.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups.
For example,
Figure BDA0002960227830000032
wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc as the substituent may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 9 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms or a triarylsilyl group having 18 to 24 carbon atoms. In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if Ar1Selected from the group consisting of substituted aryl groups having 30 carbon atoms, all of the carbon atoms of the aryl group and substituents thereon are 30.
In the present application, L1、L2、Ar1、Ar2、Ar3、R1、R2、R3The number of carbon atoms of (b) means all the number of carbon atoms. For example: l is1In the case of a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12. For example: ar (Ar)1Is composed of
Figure BDA0002960227830000041
The number of carbon atoms is 7; l is1Is composed of
Figure BDA0002960227830000042
The number of carbon atoms is 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g.Phenyl) or polycyclic aryl, in other words, the aryl can be monocyclic aryl, fused ring aryl, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. Wherein the aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. In the present application, examples of aryl groups may include, but are not limited to, phenyl, naphthyl, anthracenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
Figure BDA0002960227830000043
and the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 13. For example, the number of carbon atoms may be 6, 12, 13, 14, 15, 18, 20, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18. Specific examples of substituted aryl groups in the present application include, but are not limited to: phenyl-substituted naphthyl, naphthyl-substituted phenyl, phenyl-substituted biphenyl, dibenzothienyl-substituted phenyl, carbazolyl-substituted phenyl, phenanthrolinyl-substituted phenyl, and the like.
In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracenyl, biphenyl, fluorenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenothiazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The term "heteroaryl" as used herein may contain from 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be from 3 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 3 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 12 to 20. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, specific examples of the heteroaryl group as the substituent include, but are not limited to: pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may be a straight chain alkyl group or a branched alkyl group. Specifically, the alkyl group having 1 to 10 carbon atoms may be a straight-chain alkyl group having 1 to 10 carbon atoms or a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may be fluorine, chlorine, bromine, iodine.
In the present application, specific examples of the trialkylsilyl group having 3 to 12 carbon atoms include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.
In the present application, specific examples of the cycloalkyl group having 3 to 9 carbon atoms include, but are not limited to: cyclopentyl, cyclohexyl, norbornyl, and the like.
Specific examples of deuterated alkyl groups having 1 to 10 carbon atoms in the present application include, but are not limited to: trideuteromethyl.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
Figure BDA0002960227830000051
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is attached to other positions of the molecule through two non-positional linkages through the bicyclic ring, which are meant to include any of the possible attachments as shown in formulas (f-1) to (f-10).
Figure BDA0002960227830000052
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning thereof includes any of the possible attachment means as shown in the formulas (X '-1) -formula (X' -4).
Figure BDA0002960227830000061
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring via an delocalized linking bond, and the meaning thereof includes any of the possible linking means as shown in the formulas (Y-1) to (Y-7).
Figure BDA0002960227830000062
In one embodiment of the present application, the formula 2 in the organic compound may be selected from one of the following formulae 2a, 2b, 2c, 2d, 2e, 2f, 2 g:
Figure BDA0002960227830000063
Figure BDA0002960227830000071
the connection points in formula 1 and formula 2 are numbered as shown below, two connection points in formula 1 are numbered as 1 and 2, respectively, and four connection points in formula 2 are numbered as 1 ', 2', 3 'and 4', respectively.
Figure BDA0002960227830000072
The connection relationship between the connection points in the structures shown in formulas 1 and 2 is shown in the following table 1:
TABLE 1
Figure BDA0002960227830000073
In one embodiment of the present application, Ar is1And Ar2Each independently selected from the group consisting of substituted or unsubstituted aryl groups of 6 to 20, substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms;
optionally, the Ar is1And Ar2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, and a deuterated alkyl group having 1 to 5 carbon atoms.
Specifically, Ar is1And Ar2Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluorine, cyano, methyl,Ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, norbornyl, cyclohexane, trimethylsilyl.
In one embodiment, Ar is1And Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
In another specific embodiment of the present application, Ar is1And Ar2Each independently selected from substituted or unsubstituted groups V1Said unsubstituted group V1Selected from the group consisting of:
Figure BDA0002960227830000081
wherein the content of the first and second substances,
Figure BDA0002960227830000082
represents a chemical bond; substituted radicals V1Has one or more substituents thereon, each of which is independently selected from deuterium, fluorine, cyano, methyl, trifluoromethyl, trideuteromethyl, ethyl, n-propyl, tert-butyl, phenyl, naphthyl, biphenyl, trimethylsilyl, cyclohexyl, norbornyl; when V is1When the number of the substituents is more than 1, the substituents may be the same or different.
In further embodiments, the Ar is1And Ar2Each independently selected from the group consisting of:
Figure BDA0002960227830000083
in one embodiment of the present application, L is1And L2Each independently selected from a single bond and 6 carbon atoms-15 of a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;
optionally, said L1And L2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
Specifically, the L1And L2Specific examples of the substituent in (1) include, but are not limited to: deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
In one embodiment of the present application, L is1And L2Each 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, and a substituted or unsubstituted carbazolyl group.
In another specific embodiment, said L1And L2Each independently selected from a single bond or a substituted or unsubstituted group M1The unsubstituted radical M1Selected from the group consisting of:
Figure BDA0002960227830000091
wherein the content of the first and second substances,
Figure BDA0002960227830000092
represents a chemical bond; substituted radicals M1Having one or more substituents thereon, substituted radicals M1The substituents on (A) are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl; when the group M1When the number of the substituents is more than 1, the substituents may be the same or different.
In further embodiments, said L is1And L2Each independently selected from a single bond or the group consisting of:
Figure BDA0002960227830000093
in a preferred embodiment of the present application, L is3Is a single bond.
In one embodiment of the present application, R is1、R2、R3Each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
Specifically, R1、R2、R3Each independently selected from deuterium, phenyl, naphthyl.
In a preferred embodiment of the present application, n in the organic compound1Is 0; n is2Is 0, n3Is 0.
In one embodiment of the present application, the compound is selected from the group consisting of:
Figure BDA0002960227830000101
Figure BDA0002960227830000111
Figure BDA0002960227830000121
Figure BDA0002960227830000131
Figure BDA0002960227830000141
Figure BDA0002960227830000151
Figure BDA0002960227830000161
the synthesis method of the organic compound provided herein is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the organic compound of the present application in combination with the preparation method provided in the synthesis examples section of the present application. In other words, the synthetic examples section of the present application illustratively provides methods for the preparation of organic compounds, and the starting materials employed can be obtained commercially or by methods well known in the art. All organic compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the organic compounds will not be described in detail herein, and those skilled in the art should not be construed as limiting the present application.
A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to the first aspect of the present application;
the organic compounds provided herein can be used to form at least one organic film layer in a functional layer to improve efficiency and lifetime characteristics of an electronic component.
In one embodiment, the functional layer comprises an organic light emitting layer comprising the organic compound. In one embodiment, the organic light emitting layer comprises a host material and a guest material, and further the host material comprises an organic compound of the present application.
In one embodiment according to the application, the electronic component is an organic electroluminescent device, for example a green device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, anode 100 includes an anode material that preferably facilitates hole injection to functionA material with a large work function in the layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds. In one embodiment of the present application, the first hole transport layer 321 may be HT-01; in one embodiment of the present application, the second hole transport layer 322 may be HT-02.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. The host material of the organic light emitting layer may contain the organic compound of the present application. In some embodiments, 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 combined in the organic light emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in this application. In one embodiment of the present application, the host material of the organic light emitting layer 330 may be an organic compound of the present application.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In some embodiments of the present application, the first and second electrodes are,
the organic electroluminescent device is a green light device, and the guest materials of the organic luminescent layer 330 are GH-p and Ir (ppy)3And (4) forming.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In an exemplary embodiment of the present application, the electron transport layer 340 may be composed of ET-01 and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having 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 multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 may be composed of metal LiQ.
The organic electroluminescent device of the present application is optionally a green device.
Alternatively, a hole blocking layer 341 may be further disposed between the organic light emitting layer 330 and the electron transport layer 340.
A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
According to another embodiment, as shown in fig. 3, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.
Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
Analytical detection of intermediates and compounds in this application uses an ICP-7700 mass spectrometer.
The following will specifically explain the method for synthesizing the organic compound of the present application with reference to the synthesis examples.
The compounds of the present application were synthesized using the following methods.
(1) Synthesis of intermediate IM-a 1:
Figure BDA0002960227830000181
adding 2-bromo-9, 9-diphenylfluorene (20.0 g; 50.3mmol), indolo [2,3-a ] carbazole (14.2 g; 55.4mmol), tris (dibenzylideneacetone) dipalladium (0.9 g; 1.0mmol), tri-tert-butylphosphine (0.4 g; 2.0mmol), sodium tert-butoxide (7.3 g; 75.5mmol) and xylene (200mL) into a round-bottomed flask, and stirring at 140 ℃ for reaction for 8 hours under the protection of nitrogen; cooling to room temperature, washing the reaction liquid with water, separating liquid, drying an organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using dichloromethane/n-heptane as eluent to give intermediate IM-a1(21.8 g; 76%) as a white solid.
Referring to the procedure for intermediate IM-a1, the intermediate compounds shown in table 2 below were synthesized using reactant a in table 1 below instead of 2-bromo-9, 9-diphenylfluorene and reactant B in place of indolo [2,3-a ] carbazole:
TABLE 2
Figure BDA0002960227830000182
Figure BDA0002960227830000191
Figure BDA0002960227830000201
(2) Synthesis of compound a 1:
Figure BDA0002960227830000211
adding the intermediate IM-a1(5.0 g; 8.7mmol) and dimethylformamide (50mL) into a round-bottom flask, adding sodium hydride (0.2 g; 8.7mmol) under the protection of nitrogen at 0 ℃, and stirring for 1 hour under the condition of heat preservation; then adding 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.5 g; 13.1mmol) into the reaction solution in batches, keeping the temperature and stirring for 1 hour, then heating to 25 ℃, and stirring for reaction for 12 hours; adding a large amount of deionized water into the reaction solution, filtering, leaching the obtained solid with water and ethanol in sequence, and drying to obtain a crude product; the crude product was purified by column chromatography on silica gel using dichloromethane/n-heptane as eluent, followed by recrystallization of the resulting product using a toluene/n-heptane system to give compound A1 as a white solid (4.5 g; 64%).
Referring to the synthesis of compound a1, the compounds shown in table 3 below were synthesized using reactant C instead of intermediate IM-a1 and reactant D instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine in table 3 below:
TABLE 3
Figure BDA0002960227830000212
Figure BDA0002960227830000221
Figure BDA0002960227830000231
Figure BDA0002960227830000241
Figure BDA0002960227830000251
The mass spectra data for the compounds in table 4 are as follows:
TABLE 4
Figure BDA0002960227830000252
Figure BDA0002960227830000261
Part of the compound NMR data are shown in Table 5 below
TABLE 5
Figure BDA0002960227830000262
Device embodiments
The green organic light-emitting device was fabricated using the following method:
example 1: green organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
Figure BDA0002960227830000263
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002960227830000264
And HT-01 is vapor-deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of
Figure BDA0002960227830000265
The first hole transport layer of (1).
Vacuum evaporating HT-02 on the first hole transport layer to a thickness of
Figure BDA0002960227830000266
The second hole transport layer of (1).
On the second hole transport layer, compound a 1: GH-p: ir (ppy)3In a ratio of 50%: 45%: 5% by mass of the mixture is subjected to co-evaporation to form a film with a thickness of
Figure BDA0002960227830000267
Green emitting layer (EML).
ET-01 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002960227830000268
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002960227830000269
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA00029602278300002610
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA00029602278300002611
Forming an organic capping layer (CPL) to complete the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.
Example 2 example 30
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the light-emitting layer, compounds shown in table 6 below were used in place of compound a 1.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound I was used instead of the compound a1 in forming the light-emitting layer.
Comparative example 2
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound II was used instead of the compound a1 in forming the light-emitting layer.
Comparative example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound III was used instead of the compound a1 in forming the light-emitting layer.
The material structures used in the above examples and comparative examples are as follows:
Figure BDA0002960227830000271
for the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions shown in table 6 below:
TABLE 6
Figure BDA0002960227830000281
As can be seen from the data in table 6, the performance of the devices in examples 1-30 is improved by at least 12.11% and the lifetime is improved by at least 27.22% compared to those in comparative examples 1-3 in the present application, which are shown in examples 1-30.
Compared with comparative example 3, the organic compound provided by the application has the advantages that the stability of the molecular structure of the organic compound can be improved by introducing the large steric hindrance group diphenylfluorene, so that the service life of a device can be greatly prolonged.
Therefore, when the novel compound is used for preparing a green organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be effectively improved, the voltage can be reduced, and the service life of the organic electroluminescent device can be prolonged.
The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application. It should be noted that the various features described in the above embodiments may be combined in any suitable manner without departing from the scope of the invention.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.

Claims (12)

1. An organic compound having a structure formed by fusing formula 1 with formula 2 as follows:
Figure FDA0002960227820000011
wherein formula 1 is fused to formula 2, and represents the point of attachment of formula 1 fused to formula 2;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
L1、L2and L3The same or different, and each is independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms, substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
R1、R2and R3The same or different, and each is independently selected from deuterium, halogen group, alkyl group with 1-10 carbon atoms, naphthenic group with 3-10 carbon atoms, alkoxy group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, aryl group with 6-12 carbon atoms and heteroaryl group with 3-20 carbon atoms;
n1represents R1Number of (2), n1Is 0, 1,2, 3 or 4, n1When greater than 1, any two R1The same or different;
n2represents R2Number of (2), n2Is 0, 1 or 2, n2When greater than 1, any two R2The same or different;
n3represents R3Number of (2), n3Is 0, 1,2, 3 or 4, n3When greater than 1, any two R3The same or different;
Ar1、Ar2and L1、L2And L3Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 9 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a C1-C-10 alkylthio groups, trialkylsilyl groups having 3 to 12 carbon atoms.
2. The organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms;
preferably, Ar is1And Ar2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, a trialkylsilyl group having 3 to 6 carbon atoms, and a deuterated alkyl group having 1 to 5 carbon atoms.
3. The organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl;
preferably, Ar is1And Ar2Each substituent in (1) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, phenyl, adamantyl, cyclohexane, trimethylsilyl.
4. The organic compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from substituted or unsubstituted groups V1Said unsubstituted group V1Selected from the group consisting of:
Figure FDA0002960227820000021
wherein the content of the first and second substances,
Figure FDA0002960227820000022
represents a chemical bond; substituted radicals V1Has one or more substituents thereon, each of which is independently selected from deuterium, fluorine, cyano, methyl, trifluoromethyl, trideuteromethyl, ethyl, n-propyl, tert-butyl, phenyl, naphthyl, biphenyl, trimethylsilyl, cyclohexyl, norbornyl; when V is1When the number of the substituents is more than 1, the substituents may be the same or different.
5. The organic compound of claim 1, wherein L is1And L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;
preferably, said L1And L2Wherein the substituents are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, and an aryl group having 6 to 12 carbon atoms.
6. The organic compound of claim 1, wherein L is1And L2Each 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, and a substituted or unsubstituted carbazolyl group;
preferably, said L1And L2Wherein the substituents are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, and biphenyl.
7. The organic compound of claim 1, wherein L is1And L2Each independently selected from a single bond or a substituted or unsubstituted group M1The unsubstituted radical M1Selected from the group consisting of:
Figure FDA0002960227820000023
wherein the content of the first and second substances,
Figure FDA0002960227820000024
represents a chemical bond; substituted radicals M1Having one or more substituents thereon, substituted radicals M1The substituents on (A) are independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl; when the group M1When the number of the substituents is more than 1, the substituents may be the same or different.
8. The organic compound of claim 1, wherein L is3Selected from single bonds.
9. The organic compound of claim 1, wherein the compound is selected from the group consisting of:
Figure FDA0002960227820000031
Figure FDA0002960227820000041
Figure FDA0002960227820000051
Figure FDA0002960227820000061
Figure FDA0002960227820000071
Figure FDA0002960227820000081
Figure FDA0002960227820000091
10. an electronic component comprising an anode and a cathode which are disposed opposite to each other, and a functional layer which is provided between the anode and the cathode and contains the organic compound according to any one of claims 1 to 9;
preferably, the functional layer includes an organic light emitting layer including the organic compound;
more preferably, the organic light emitting layer includes a host material and a guest material, and the host material includes the organic compound.
11. The electronic element according to claim 10, wherein the electronic element is an organic electroluminescent device;
preferably, the organic electroluminescent device is a green organic electroluminescent device.
12. An electronic device, characterized by comprising the electronic component of claim 10 or 11.
CN202110236134.3A 2021-02-09 2021-03-03 Organic compound, and electronic element and electronic device using same Active CN113004289B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN202110181975 2021-02-09
CN2021101819759 2021-02-09

Publications (2)

Publication Number Publication Date
CN113004289A true CN113004289A (en) 2021-06-22
CN113004289B CN113004289B (en) 2022-03-29

Family

ID=76404030

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110236134.3A Active CN113004289B (en) 2021-02-09 2021-03-03 Organic compound, and electronic element and electronic device using same

Country Status (1)

Country Link
CN (1) CN113004289B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114437081A (en) * 2020-11-04 2022-05-06 三星Sdi株式会社 Compound for organic optoelectronic device, composition for organic optoelectronic device, and display device
WO2023273356A1 (en) * 2021-06-30 2023-01-05 南京高光半导体材料有限公司 Compound containing carbazole and carbazole derivative, and organic electroluminescent device
WO2023277645A1 (en) * 2021-07-01 2023-01-05 Samsung Display Co., Ltd. Organic molecules for optoelectronic devices

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108440537A (en) * 2018-04-18 2018-08-24 石家庄诚志永华显示材料有限公司 Carbazole derivates, material and organic electroluminescence device comprising the carbazole derivates
CN109928974A (en) * 2017-12-15 2019-06-25 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN110294703A (en) * 2018-03-21 2019-10-01 三星Sdi株式会社 Composition, organic electro-optic device and display device for organic electro-optic device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109928974A (en) * 2017-12-15 2019-06-25 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN110294703A (en) * 2018-03-21 2019-10-01 三星Sdi株式会社 Composition, organic electro-optic device and display device for organic electro-optic device
CN108440537A (en) * 2018-04-18 2018-08-24 石家庄诚志永华显示材料有限公司 Carbazole derivates, material and organic electroluminescence device comprising the carbazole derivates

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114437081A (en) * 2020-11-04 2022-05-06 三星Sdi株式会社 Compound for organic optoelectronic device, composition for organic optoelectronic device, and display device
CN114437081B (en) * 2020-11-04 2024-06-18 三星Sdi株式会社 Compound for organic optoelectronic device, composition for organic optoelectronic device, and display device
WO2023273356A1 (en) * 2021-06-30 2023-01-05 南京高光半导体材料有限公司 Compound containing carbazole and carbazole derivative, and organic electroluminescent device
WO2023277645A1 (en) * 2021-07-01 2023-01-05 Samsung Display Co., Ltd. Organic molecules for optoelectronic devices

Also Published As

Publication number Publication date
CN113004289B (en) 2022-03-29

Similar Documents

Publication Publication Date Title
CN112110825B (en) Arylamine compound, electronic element using arylamine compound and electronic device
CN112110849B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN111909043B (en) Nitrogen-containing compound, electronic component, and electronic device
CN111454197B (en) Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN111777517B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN111848501B (en) Nitrogen-containing compound, and electronic element and electronic device using same
CN113004289B (en) Organic compound, and electronic element and electronic device using same
CN113233987B (en) Nitrogen-containing compound, electronic element comprising same and electronic device
CN112300055A (en) Nitrogen-containing compound, electronic component, and electronic device
CN112142674B (en) Organic compound, and electronic element and electronic device using same
CN113121408B (en) Nitrogen-containing compound, electronic component, and electronic device
CN113582997A (en) Nitrogen-containing compound, electronic component, and electronic device
CN111153880A (en) Nitrogen-containing compound, electronic component, and electronic device
WO2022068292A1 (en) Organic compound, and electronic element and electronic device using same
CN112375083B (en) Organic compound, and organic electroluminescent device and electronic device using same
CN113735861A (en) Organic compound, and electronic element and electronic device using same
CN114315836A (en) Organic compound, organic electroluminescent device comprising organic compound and electronic device comprising organic compound
CN114057705B (en) Nitrogen-containing compound, and electronic element and electronic device comprising same
CN112939976B (en) Organic compound, and electronic element and electronic device using same
CN112321595B (en) Compound, electronic element and electronic device
CN114920750A (en) Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN115521214B (en) Organic compound, and electronic component and electronic device including the same
CN115504989B (en) Organic compound, electronic component, and electronic device
CN113666832B (en) Organic compound, and electronic element and electronic device using same
CN117603209A (en) Organic compound, organic electroluminescent device and electronic device comprising the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant