CN117466912A - Organic compound, organic electroluminescent device and electronic device - Google Patents

Organic compound, organic electroluminescent device and electronic device Download PDF

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CN117466912A
CN117466912A CN202310005537.6A CN202310005537A CN117466912A CN 117466912 A CN117466912 A CN 117466912A CN 202310005537 A CN202310005537 A CN 202310005537A CN 117466912 A CN117466912 A CN 117466912A
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carbon atoms
substituted
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马天天
杨雷
冯震
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescence device using the same and an electronic device.

Description

Organic compound, organic electroluminescent device and electronic device
Technical Field
The present disclosure relates to the field of organic compounds, and more particularly, to an organic compound, and an organic electroluminescent device and an electronic device including the same.
Background
With the development of electronic technology and the advancement of material science, the range of applications of electronic components for realizing electroluminescence 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 organic light emitting layer, a hole transport layer between the organic light emitting layer and the anode, and an electron transport layer between the organic light emitting layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light emitting layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the organic light-emitting layer under the action of the electric field, holes at the anode side also move to the organic 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 to release energy outwards, so that the organic light-emitting layer emits light outwards.
The prior art discloses host materials that can be used to prepare organic light emitting layers in organic electroluminescent devices. However, there remains a need to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
In order to solve the above problems, an object of the present application is to provide an organic compound, which can improve the performance of an organic electroluminescent device and an electronic apparatus, for example, reduce the driving voltage of the device, and increase the efficiency and lifetime of the device, and an organic electroluminescent device and an electronic apparatus including the organic compound.
According to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
wherein one of X and Y is O and the other is
L 1 And L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 、Ar 2 and Ar is a group 3 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
L 1 、L 2 、Ar 1 、Ar 2 and Ar is a group 3 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms;
each R is 1 And R is 2 And are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms and a haloaryl group having 5 to 18 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
n 1 r represents 1 Number n of (n) 1 Selected from 0, 1 or 2, and when n 1 When the number is greater than 1, each R 1 The same or different;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4, and when n 2 When the number is greater than 1, each R 2 The same or different.
According to a second aspect of the present application, there is provided an organic electroluminescent device 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.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
The core structure in the organic compound is a group formed by simultaneously fusing an oxazole group and a benzofuran group on a phenyl group in a specific way, and the group and a triazine group are combined to obtain a novel compound of the application; such structures have high aromatic conjugation effects, bring about high electron mobility, and thus have good energy transfer characteristics, more suitable energy level characteristics, and high molecular structural stability. When the compound is applied to an organic light-emitting layer in an organic electroluminescent device, the driving voltage and the light-emitting efficiency of the device can be effectively improved, and meanwhile, the good service life characteristic is maintained.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
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 the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
320. First hole transport layer 330, second hole transport layer 340, organic light emitting layer 350, and electron transport layer
360. Electron injection layer 400 and electronic device
Detailed Description
In view of the foregoing problems of the prior art, it is an object of the present invention to provide an organic compound, which can improve the performance of an organic electroluminescent device and an electronic apparatus, for example, reduce the driving voltage of the device, and increase the efficiency and lifetime of the device, and an organic electroluminescent device and an electronic apparatus including the same.
According to a first aspect of the present application, there is provided an organic compound having a structure as shown in formula 1:
wherein one of X and Y is O and the other is
L 1 And L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 、Ar 2 and Ar is a group 3 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
L 1 、L 2 、Ar 1 、Ar 2 and Ar is a group 3 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms;
each R is 1 And R is 2 And are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 6 to 20 carbon atoms and a haloaryl group having 5 to 18 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
n 1 r represents 1 Is set in the number of (3),n 1 selected from 0, 1 or 2, and when n 1 When the number is greater than 1, each R 1 The same or different;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4, and when n 2 When the number is greater than 1, each R 2 The same or different.
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, ""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 aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, cyano, halogen, alkyl, haloalkyl, deuterated alkyl, aryl, deuterated aryl, haloaryl, heteroaryl, cycloalkyl, or the like. The number of substitutions 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, substituted or unsubstituted functionalityThe number of carbon atoms of a group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. 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. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, spirobifluorenyl radicals, and the like. As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, terphenyl includesAnd->
In the present application, the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, for example, a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, 30, 31, 32, 33, 35, 36, 37, 38, 39, or 40. 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 20 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 12 carbon atoms.
In the present application, the fluorenyl group may be substituted with 1 or more substituents, wherein any two adjacent substituents may be bonded to each other to form a ring structure. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: 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, 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, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be selected from 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, 38, 39 or 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having from 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having from 12 to 18 carbon atoms.
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. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, 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 and the like.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
Specific examples of deuterated alkyl groups herein include, but are not limited to, tridentate methyl.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3,4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt 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 the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
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 formulas (X '-1) to (X' -4).
In some embodiments of the present application, X is O and Y is
In other embodiments of the present application, X isY is O.
In some embodiments of the present application, the organic compound is selected from compounds represented by formula a or formula B:
in some embodiments of the present application, the organic compound is selected from the group consisting of compounds represented by formulas 1-1, 1-2, 1-3, or 1-4:
in some embodiments of the present application, the organic compound is selected from the group consisting of compounds represented by formula A1, formula A2, formula A3, formula A4, formula A5, formula A6, formula B1, formula B2, formula B3, formula B4, formula B5, or formula B6:
in some embodiments of the present application, 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 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Optionally, the 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 having 1 to 5 carbon atoms or phenyl group.
Further alternatively, L 1 And L 2 The same or different, are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms
In some embodiments of the present application, L 1 And L 2 Identical or different, each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstitutedUnsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene.
Optionally, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, L 1 And L 2 The same or different, are each independently selected from a single bond, a substituted or unsubstituted group V, the unsubstituted group V being selected from the group consisting of:
wherein,represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Specifically, L 1 And L 2 The same or different, each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
Optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected fromDeuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, deuterated alkyl group having 1 to 5 carbon atoms, pentadeuterated phenyl group or phenyl group.
In other embodiments of the present application, ar 1 And Ar is a group 2 The same or different are respectively and independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl and substituted or unsubstituted dibenzothienyl.
Optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.
In some embodiments of the present application, ar 1 And Ar is a group 2 The same or different, are each independently selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
wherein,represents a chemical bond; the substituted group W has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on the group W is more than 1, the substituents are the same or different.
Alternatively, ar 1 And Ar is a group 2 The same or different, each independently selected from the group consisting of:
specifically, ar 1 And Ar is a group 2 The same or different, each independently selected from the group consisting of:
in some embodiments of the present application, ar 3 Selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.
Optionally, the Ar 3 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, pentadeuterated phenyl or phenyl.
In some embodiments of the present application, ar 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl.
Optionally, the Ar 3 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.
Specifically, ar 3 Selected from the group consisting of:
in some embodiments of the present application,and->Each independently selected from the group consisting of:
in particular, the method comprises the steps of,and->Each independently selected from the group consisting of:
/>
in some embodiments of the present application, in formula 1Selected from the group consisting of:
/>
/>
specifically, in formula 1Selected from the group consisting of:
/>
in some embodiments of the present application, R 1 And R is 2 Identical or different, each independently of the others is deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, n 1 And n 2 All 0.
In some embodiments of the present application, the organic compound is selected from the group consisting of the compounds as set forth in claim 11.
According to a second aspect of the present application, there is provided an organic electroluminescent device 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 an organic compound of the present application.
In some embodiments of the present application, the organic electroluminescent device is a red organic electroluminescent device.
In other embodiments of the present application, the organic electroluminescent device is a green organic electroluminescent device.
As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are sequentially stacked.
Alternatively, the 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. A transparent electrode including Indium Tin Oxide (ITO) as an anode is preferable.
Alternatively, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art will be able to select from the prior art, and this application is not particularly limited. In some embodiments of the present application, first hole transport layer 320 is HT-24 and second hole transport layer 330 is HT-23 or HT-25.
Optionally, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
/>
in some embodiments of the present application, hole injection layer 310 is comprised of PD and HT-24.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting layer material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 340 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 340 and electrons injected into the organic light emitting layer 340 may be recombined at the organic light emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the dopant material, thereby enabling the dopant material to emit light.
The host material of the organic light emitting layer 340 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application.
In one embodiment of the present application, the organic light emitting layer 340 comprises the organic compound of the present application.
Alternatively, the organic compound of the present application is used as a host material (electronic type host material) of the organic light emitting layer 340.
In some embodiments of the present application, the hole-type host material of the organic light emitting layer 340 isOr->
The guest material of the organic light emitting layer 340 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 in this application. Guest materials are also known as doping materials or dopants.
Specific examples of green phosphorescent dopants for green organic electroluminescent devices include but are not limited to,
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specific examples of red phosphorescent dopants for red organic electroluminescent devices include but are not limited to,
in a more specific embodiment, the host material of the organic light emitting layer 340 is an organic compound and RH-P of the present application, and the guest material is RD.
In another more specific embodiment, the host material of the organic light emitting layer 340 is an organic compound and GH-P of the present application, and the guest material is GD.
The electron transport layer 350 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from but not limited to ET-01, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited in comparison. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:
in some embodiments of the present application, electron transport layer 350 is comprised of ET-1 and LiQ.
In this 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 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.
In some embodiments of the present application, the electron injection layer 360 may include ytterbium (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.
All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
The synthetic method of the organic compound provided in the present application is not particularly limited, and a person skilled in the art can determine a suitable synthetic method from the preparation method provided in the organic compound in combination with the preparation example section of the present application. All organic compounds provided herein can be obtained by one skilled in the art from these exemplary preparation methods, and all specific preparation methods for preparing the organic compounds are not described in detail herein, and should not be construed as limiting the present application.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare a number of organic compounds of the present application, and that other methods for preparing compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those compounds not exemplified in accordance with the present application may be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
Synthesis of intermediates a 1-o:
3-bromo-2-chlorodibenzofuran (15.0 g;53.3 mmol), cuprous iodide (1.0 g;5.3 mmol), 8-hydroxyquinaldine (1.7 g;10.7 mmol), tetrabutylammonium hydroxide (41.5 g;159.8 mmol), dimethyl sulfoxide (150 mL) and deionized water (200 mL) were added to a round-bottomed flask containing nitrogen protection, and the mixture was heated to 125℃to 130℃with stirring, and reacted for 36 hours; cooling to room temperature, adding dichloromethane (500 mL) and deionized water (500 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product obtained was purified by silica gel column chromatography using methylene chloride/n-heptane system to give intermediate a1-o (8.4 g; yield: 72%) as a white solid
Referring to the synthesis of intermediates a1-o, reactant A in Table 1 below was substituted for 3-bromo-2-chlorodibenzofuran to synthesize the intermediates shown in Table 1 below:
TABLE 1
Synthesis of intermediates a 1-c:
intermediate a1-o (8.1 g;37.2 mmol), benzylamine (8.0 g;74.3 mmol), 2, 6-tetramethylpiperidine oxide (11.6 g;74.3 mmol), ammonium persulfate (17.0 g;74.3 mmol) and acetonitrile (70 mL) were added to a round bottom flask containing nitrogen protection and reacted at 50℃to 55℃for 72 hours with stirring; cooling to room temperature, adding dichloromethane (150 mL) and deionized water (200 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a solvent to give intermediate a1-c (5.0 g; yield: 42%) as a white solid.
Referring to the synthesis method of the intermediates a1 to c, the following reactant B in table 2 was substituted for the intermediates a1 to o, and reactant N was substituted for benzylamine, to synthesize the intermediates shown in table 2 below:
TABLE 2
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Synthesis of intermediates a 1-b:
intermediate a1-c (4.9 g;15.3 mmol), pinacol biborate (5.8 g;23.0 mmol), tris (dibenzylideneacetone) dipalladium (0.1 g;0.2 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.1 g;0.3 mmol), potassium acetate (2.3 g;23.0 mmol) and 1, 4-dioxane (50 mL) were added to a round bottom flask containing nitrogen protection and reacted at 100℃to 105℃for 24 hours with stirring; cooling to room temperature, adding dichloromethane (100 mL) and deionized water (150 mL) into the reaction solution, separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a solvent to give intermediate a1-b (4.7 g; yield: 75%) as a white solid.
Referring to the synthesis of intermediates a1-b, the following intermediates shown in Table 3 were synthesized with reactant C in place of intermediates a1-C in Table 3 below:
TABLE 3 Table 3
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Synthesis of Compound A1-1:
intermediate a1-b (4.5 g;10.9 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.1 g;11.5 mmol), tetrakis triphenylphosphine palladium (0.3 g;0.2 mmol), potassium carbonate (3.0 g;21.9 mmol), tetrabutylammonium bromide (0.7 g;2.2 mmol), toluene (40 mL), ethanol (10 mL) and deionized water (10 mL) were added to a round bottom flask containing nitrogen protection, heated to 75℃to 80℃and reacted with stirring for 16 hours; cooling the reaction solution to room temperature, adding deionized water (80 mL), separating the solution, washing an organic phase with water, drying the organic phase with anhydrous magnesium sulfate, and removing the solvent under reduced pressure; the crude product was purified by silica gel column chromatography using toluene/n-heptane solvent system, followed by recrystallization purification using toluene/n-heptane solvent system to give compound A1-1 (3.8 g; yield: 67%) as a white solid.
Referring to the synthesis of compound A1-1, replacing intermediate A1-b with reactant D in Table 4, replacing 2-chloro-4, 6-diphenyl-1, 3, 5-triazine with reactant E, the compounds shown in Table 4 below were synthesized:
TABLE 4 Table 4
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Mass spectrum data of a part of the compounds are shown in the following table 5
TABLE 5
The nuclear magnetic data of some compounds are shown in Table 6 below
TABLE 6
Preparation of organic electroluminescent device
Example 1: preparation of green organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnOn the ITO/Ag/ITO substrate, ultraviolet ozone and O are used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent is used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate.
On the experimental substrate (anode), PD: HT-24 was set at 2%: co-evaporation is carried out at an evaporation rate ratio of 98% to form a film with a thickness ofIs then vacuum evaporated onto the hole injection layer to form HT-24 with a thickness of +.>Is provided.
Vacuum evaporating compound HT-23 on the first hole transport layer to form a film having a thickness ofIs provided.
On the second hole transport layer, compound A1-1: GH-P: GD at 47%:47%: co-evaporation is carried out at an evaporation rate of 6% to form a film with a thickness ofAn organic light-emitting layer (green light-emitting layer).
On the organic light-emitting layer, mixing and evaporating the compounds ET-1 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness ofThereby completing the manufacture of the green organic electroluminescent device.
Examples 2 to 23
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound in table 7 below (collectively referred to as "compound X") was used instead of the compound A1-1 in example 1 in the preparation of the light-emitting layer.
Comparative examples 1 to 4
An organic electroluminescent device was fabricated by the same method as in example 1, except that compound I, compound II, compound III and compound IV were used in place of compound A1-1 in example 1, respectively, in the fabrication of the light-emitting layer.
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The green organic electroluminescent devices prepared in examples 1 to 23 and comparative examples 1 to 4 were subjected to performance test, in particular, at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 15mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 7.
TABLE 7
Referring to table 7 above, it is understood that when the compounds of the present application were used as host materials for green organic electroluminescent devices, the current efficiency of the devices was improved by at least 12.8% and the T95 lifetime was improved by at least 14.7% as compared to comparative examples 1 to 4.
When the organic compound is used as a luminescent layer material in a green organic electroluminescent device, compared with the compound I and the compound III, the organic compound has relatively lower driving voltage and higher efficiency, and the reason is probably that the direct connection mode between triazine and a rigid parent nucleus structure in the organic compound of the application enables a molecular structure to have a larger conjugation range. In contrast, the organic compounds of the present application have higher efficiency in the case of a close driving voltage than the compounds II and IV, and may be due to the higher first triplet energy level of the molecular structure due to the specific inter-group fusion manner of the core structure. In particular, the performance is optimal when the triazine group is attached to a benzene ring containing a fused oxazole.
Example 24: preparation of red organic electroluminescent device
The anode pretreatment is carried out by the following steps: at the thickness ofSequentially isOn the ITO/Ag/ITO substrate, ultraviolet ozone and O are used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent is used for cleaning the surface of the ITO/Ag/ITO substrate to remove impurities and greasy dirt on the surface of the substrate.
On the experimental substrate (anode), PD: HT-24 was set at 2%: co-evaporation is carried out at an evaporation rate ratio of 98% to form a film with a thickness ofIs formed into a thickness of HT-24 by vacuum evaporation on the Hole Injection Layer (HIL)Is provided.
Vacuum evaporating compound HT-25 on the first hole transport layer to form a film having a thickness ofIs provided.
On the second hole transport layer, RH-P: compounds A1-21:RD were combined at 49%: the vapor deposition rate ratio of 49 percent to 2 percent is used for co-vapor deposition to form the film with the thickness ofAn organic light-emitting layer (red light-emitting layer).
On the organic light-emitting layer, mixing and evaporating the compounds ET-1 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Electron Injection Layer (EIL) of (a), then evaporating magnesium (Mg) and silver (Ag) at a vapor deposition rate of 1:9Mixing, vacuum evaporating on the electron injection layer to form a film with a thickness +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness ofThereby completing the fabrication of the red organic electroluminescent device.
Examples 25 to 31
An organic electroluminescent device was produced by the same method as in example 1, except that the compounds in the following table 8 (collectively referred to as "compound X") were used instead of the compounds A1 to 21 in example 1 in producing the light-emitting layer.
Comparative examples 5 to 6
An organic electroluminescent device was fabricated by the same method as in example 1, except that compound v and compound vi were used in place of the compounds A1 to 21 in example 20, respectively, in fabricating a light-emitting layer.
Wherein, in preparing each example and comparative example, the main compound used has the following structure:
performance test was performed on the red organic electroluminescent devices prepared in examples 24 to 31 and comparative examples 4 and 5, specifically at 10mA/cm 2 IVL performance of the device under the condition of (1) and lifetime of the T95 device at 15mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 8.
TABLE 8
When the organic compound is used as a light-emitting layer material in a red organic electroluminescent device, the current efficiency is improved by at least 19.0%, the lifetime is improved by at least 11.1%, and the driving voltage is reduced by at least 0.13V as compared with comparative examples 5 and 6.
Compared with the compound V, when the organic compound is used for a main material layer of a light-emitting layer of an organic electroluminescent device, the device has obviously lower driving voltage, higher efficiency and longer T95 service life, and possibly because triazine serving as an electron transport group has higher aromatic conjugation effect and photoelectric stability compared with pyrimidine.
Compared with the compound VI, when the organic compound is used for the main material layer of the luminous layer of the organic electroluminescent device, the device can have higher luminous efficiency under the condition of keeping lower driving voltage; the reason for this is probably that the specific way of fusion between specific groups of the core structure of the organic compounds of the present application results in a higher first triplet energy level of the compound, while the LUMO energy level is more matched to the adjacent layers.

Claims (13)

1. An organic compound, characterized in that the organic compound has a structure as shown in formula 1:
wherein one of X and Y is O and the other is-n=;
L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 、Ar 2 and Ar is a group 3 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
L 1 、L 2 、Ar 1 、Ar 2 and Ar is a group 3 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms and cycloalkyl having 3 to 10 carbon atoms;
each R is 1 And R is 2 And are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a halogenated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
n 1 r represents 1 Number n of (n) 1 Selected from 0, 1 or 2, and when n 1 When the number is greater than 1, each R 1 The same or different;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1,2, 3 or 4, and when n 2 When the number is greater than 1, each R 2 The same or different.
2. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of compounds represented by formula 1-1, formula 1-2, formula 1-3, and formula 1-4:
3. the organic compound according to claim 1, wherein L 1 And L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-20 carbon atoms and substituted or unsubstituted heteroarylene with 12-20 carbon atoms;
optionally, the 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 having 1 to 5 carbon atoms or phenyl group.
4. The organic compound according to claim 1, wherein L 1 And L 2 The same or different is respectively and independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted dibenzofuranylene and substituted or unsubstituted dibenzothiophenylene;
optionally, the L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
5. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 12-24 carbon atoms;
optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, halogenated alkyl groups with 1 to 5 carbon atoms, deuterated alkyl groups with 1 to 5 carbon atoms, pentadeuterated phenyl groups or phenyl groups.
6. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different, are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstitutedUnsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl;
optionally, the Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.
7. The organic compound according to claim 1, wherein Ar 3 A substituted or unsubstituted aryl group having 6 to 12 carbon atoms;
optionally, the Ar 3 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, pentadeuterated phenyl or phenyl.
8. The organic compound according to claim 1, wherein Ar 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted biphenyl;
optionally, the Ar 3 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.
9. The organic compound according to claim 1, wherein,and->Each independently selected from the group consisting of:
10. the organic compound according to claim 1, wherein in formula 1Selected from the group consisting of:
11. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
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12. the organic electroluminescent device is characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode;
the functional layer contains the organic compound according to any one of claims 1 to 11;
optionally, the functional layer comprises an organic light emitting layer; the organic light-emitting layer contains the organic compound;
optionally, the organic electroluminescent device is a green/red organic electroluminescent device.
13. An electronic device comprising the organic electroluminescent device as claimed in claim 12.
CN202310005537.6A 2022-12-23 2023-01-04 Organic compound, organic electroluminescent device and electronic device Pending CN117466912A (en)

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