CN115490655B - Organic compound, organic electroluminescent device and electronic device - Google Patents

Organic compound, organic electroluminescent device and electronic device Download PDF

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CN115490655B
CN115490655B CN202210173126.3A CN202210173126A CN115490655B CN 115490655 B CN115490655 B CN 115490655B CN 202210173126 A CN202210173126 A CN 202210173126A CN 115490655 B CN115490655 B CN 115490655B
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CN115490655A (en
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杨敏
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Material Science Co Ltd
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Abstract

The application belongs to the technical field of organic materials, and provides an organic compound, and the structure of the organic compound is shown as a formula 1. The application also provides an organic electroluminescent device and an electronic device comprising the organic compound. The organic compound can be used as an electron transport layer material or an organic electroluminescent layer material, so that the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency can be improved to a certain extent.

Description

Organic compound, organic electroluminescent device and electronic device
Technical Field
The present disclosure relates to the field of organic materials, and in particular, to an organic compound, an organic electroluminescent device, and an electronic device.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
At present, for a red light organic electroluminescent device, there are still problems of reduced luminous efficiency, shortened service life and the like, thereby resulting in reduced device performance. Therefore, organic materials have to solve these efficiency or lifetime problems, and there is a continuous need to develop new materials for organic light emitting devices that are highly efficient, long-lived, and suitable for mass production.
It should be noted that the information disclosed in the foregoing background section is only for enhancing understanding of the background of the present application and thus may include information that does not form the prior art that is already known to those of ordinary skill in the art.
Disclosure of Invention
The present application aims to overcome the defects in the prior art, and provides an organic compound, an organic electroluminescent device and an electronic device containing the same, which can improve luminous efficiency and prolong service life of the device.
To achieve the above object, the first aspect of the present application provides an organic compound having a structure represented by formula 1:
wherein Y has a structure represented by formula 2, and the structure represented by formula 3 is fused at any two adjacent positions in formula 2, and represents a point of connection where formula 2 and formula 3 are fused with each other;
each R is 4 The same or different, are each independently selected from hydrogen, deuterium, halogen groups, alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 20 carbon atomsAnd heteroaryl groups having 3 to 20 carbon atoms;
each R is 4 Each of the substituents is independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a phenyl group;
L 1 、L 2 and L 3 The same or different, are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
each Ar is the same or different and is independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
each R is 5 The same or different, each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms;
n 1 Representation ofNumber n of (n) 1 Selected from 0, 1 or 2;
n 2 representation ofNumber n of (n) 2 Selected from 1 or 2;
n 4 r represents 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
optionally, any two adjacent R 4 Forming a ring;
n 5 r represents 5 Number n of (n) 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8, when n 5 When the number is greater than 1, any two R 5 The same or different;
optionally, any two adjacent R 5 Forming a ring;
L 1 、L 2 、L 3 and Ar are the same or different,each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms;
optionally, in Ar, any two adjacent substituents form a ring.
A second aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound of the first aspect of the present application.
A second aspect of the present application provides an electronic device comprising an organic electroluminescent device according to the second aspect of the present application.
Through the technical scheme, the organic compound contains an anthracene structure, the structure has higher triplet state energy level and wider energy gap, wherein the anthracene ring has higher fluorescence quantum yield and easy modification, and the conjugated system of the compound is changed by introducing dibenzofuranyl into molecules, so that the light-emitting wavelength is changed. The tetramethyl cyclohexane group is condensed on the dibenzofuran ring to change the spatial arrangement of the compound, reduce the molecular stacking effect and the molecular crystallization capability, and improve the film forming property of the compound, thereby further improving the service life of the device. When the organic compound is used as an electron transport layer material, the compound molecules are connected with heteroaryl groups, so that the electron transport capacity of the structure is improved, the electron mobility is improved, the carrier transport is balanced, and the organic compound is suitable for an electron transport layer. When the organic compound is used as a host material of a light emitting layer (especially, a blue host material), device performance can be significantly improved.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate embodiments consistent with the application and together with the description, serve to explain the principles of the application.
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.
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 electroluminescent layer; 350. an electron transport layer; 360. an electron injection layer; 370. an organic capping layer; 400. an electronic device.
Specific embodiments thereof have been shown by way of example in the drawings and will herein be described in more detail. These drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but to illustrate the concepts of the present application to those skilled in the art by reference to specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
The first aspect of the present application provides an organic compound, wherein the structure of the organic compound is shown in formula 1:
wherein Y has a structure represented by formula 2, and the structure represented by formula 3 is condensed at any two adjacent positions in formula 2, and represents formulas 2 and 2
A point of attachment fused to each other of formula 3;
each R is 4 The same or different, each independently selected from the group consisting of hydrogen, deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms;
each R is 4 Each of the substituents is independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a phenyl group;
L 1 、L 2 and L 3 The same or different, are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Each Ar is the same or different and is independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
each R is 5 The same or different, each independently selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, and an alkyl group having 1 to 10 carbon atoms;
n 1 representation ofNumber n of (n) 1 Selected from 0, 1 or 2;
n 2 representation ofNumber n of (n) 2 Selected from 1 or 2;
n 4 r represents 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
optionally, any two adjacent R 4 Forming a ring;
n 5 r represents 5 Number n of (n) 5 Selected from 1, 2, 3, 4, 5, 6, 7 or 8, when n 5 When the number is greater than 1, any two R 5 The same or different;
optionally, any two adjacent R 5 Forming a ring;
L 1 、L 2 、L 3 and Ar are the same or different and are each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, and an alkoxy group having 1 to 10 carbon atoms;
Optionally, in Ar, any two adjacent substituents form a ring.
In the present application,represented by the parent nucleus anthracene, respectively linked to n 1 Personal->
In the present application,represented by the parent nucleus anthracene, respectively linked to n 2 Personal->
In the present application, the ring refers to a saturated or unsaturated ring such as cyclohexane, cyclopentane, adamantane, benzene ring, naphthalene ring, phenanthrene ring, fluorene ring, etc., but is not limited thereto.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, two adjacent substituents form a ring; by "is meant that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In this application, the descriptions used herein of the manner in which each … … is independently "and" … … is independently "and" … … is independently selected from "are interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the 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, non-positional connection means a single bond extending from a 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 phenanthryl group represented by the formula (X') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
In the present application, R 4 、R 5 、L 1 、L 2 、L 3 And the number of carbon atoms of Ar refer to all the numbers of carbon atoms. For example, if L 1 Selected from the group consisting of substituted arylene groups having 12 carbon atoms, then the arylene groups and all of the substituents thereon have 12 carbon atoms. For example: ar isIts carbon isAn atomic number of 7; l (L) 1 Is->The number of carbon atoms is 12.
In the present application, "hetero" means that at least 1 heteroatom such as B, N, O, S, se, si or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, in this application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Alternatively, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In this application cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. Cycloalkyl groups may have 3 to 10 carbon atoms, in this application, numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "5 to 10 carbon atoms" means that 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms may be contained. Alternatively, specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the like.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. I.e.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, tetrabiphenyl, pentabiphenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. The "substituted or unsubstituted aryl" herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 25, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 12. For example, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25, 30, although other numbers are possible and are not listed here. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
As used herein, arylene refers to a divalent group formed by the further loss of one hydrogen atom from an aryl group.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, or the like.
It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and its substituents being 18.
In the present application, specific examples of aryl groups as substituents include, but are not limited to: phenyl, naphthyl, anthryl, phenanthryl, dimethylfluorenyl, biphenyl, and the like.
In this application, fluorenyl groups may be substituted and two substituents may combine with each other to form a spiro structure, specific examples include, but are not limited to, the following structures:
in the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, which may be at least one of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-aryl carbazolyl (such as N-phenyl carbazolyl) and N-heteroaryl carbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds. The "substituted or unsubstituted heteroaryl" of this application may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3 to 27, in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 3 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted heteroaryl may be 12 to 20. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18 or 20, although other numbers are possible and are not listed here.
In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like.
It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, specific examples of heteroaryl groups as substituents include, but are not limited to: dibenzofuranyl, dibenzothiophenyl, carbazolyl, N-phenylcarbazolyl, and the like.
In the present application, halogen groups may include fluorine, iodine, bromine, chlorine, and the like.
In some embodiments of the present application, the structure of the organic compound of formula 1 is selected from the structures of formula 1-1, formula 1-2, formula 1-3, or formula 1-4:
wherein in the formulae 1-2 and 1-3, each L 1 The Ar is the same or different.
In some embodiments of the present application, L 1 、L 2 And L 3 Identical or different, are each independently selected from the group consisting of a single bond, a substituted or unsubstituted sub-group having 6 to 18 carbon atoms Aryl, and substituted or unsubstituted heteroarylene having 5 to 20 carbon atoms.
Alternatively, L 1 、L 2 And L 3 And are the same or different and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atoms.
Optionally, the L 1 、L 2 And L 3 The substituents in (a) are the same or different and are each independently selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, biphenyl groups, and phenyl groups.
Specifically, the L 1 、L 2 And L 3 The substituents in (a) are the same or different and are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, biphenyl, and phenyl.
In some embodiments of the present application, L 1 、L 2 And L 3 The same or different are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalinylene group, a substituted or unsubstituted benzo [ f ] ]Quinoxalinyl, substituted or unsubstituted triazinylene, and substituted or unsubstituted:
alternatively, L 2 Selected from the group consisting of single bond, phenylene, naphthylene, biphenylene, pyridylene, fluorenylene, dibenzofuranylene,dibenzothiophenylene, carbazolylene or benzimidazole.
In some embodiments of the present application, L 1 、L 2 And L 3 The groups are the same or different and are each independently selected from a single bond, a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more than two substituents, the substituents in the substituted group W are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, biphenyl, and phenyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.
Alternatively, L 1 、L 2 And L 3 The same or different, each independently selected from the group consisting of a single bond or:
in some embodiments of the present application, ar is selected from the group consisting of a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having from 3 to 27 carbon atoms.
Optionally, the substituents in Ar are the same or different and are each independently selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms;
optionally, in Ar, any two adjacent substituents form a saturated or unsaturated ring having 5 to 13 carbon atoms.
Specifically, the substituents in Ar are the same or different and are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, adamantyl, phenyl, naphthyl and biphenyl.
In some embodiments of the present application, ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzo [ f ] quinoxalinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted:
Optionally, in Ar, any two adjacent substituents form a fluorene ring.
In some embodiments of the present application, ar is selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein,,represents a chemical bond; the substituted group V contains one or more substituents, each of which is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl; and is also provided withWhen the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Optionally, ar is selected from the group consisting of:
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in some embodiments of the present application, each R 4 The same or different, are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
Alternatively, each R 4 The substituents of (a) are selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl; optionally, any two adjacent R 4 Forming a benzene ring.
In some embodiments of the present application, each R 4 The same or different, each independently selected from the group consisting of fluorine, cyano, methyl, and:
in some embodiments of the present application, each R 5 The same or different, each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl.
In some embodiments of the present application, the Y is selected from the group consisting of:
optionally, Y is selected from the group consisting of:
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in some embodiments of the present application, the organic compound is selected from the group consisting of:
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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.
A second aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound of the first aspect of the present application.
For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains an organic compound provided in the first aspect of the present application.
According to some embodiments, the organic electroluminescent device may be, for example, a top-emitting organic electroluminescent device.
According to some embodiments, the organic electroluminescent device may be, for example, a blue organic electroluminescent device.
In one embodiment of the present application, the functional layer comprises an organic electroluminescent layer comprising the organic compound.
In another embodiment of the present application, the functional layer comprises an electron transport layer comprising the organic compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200, which are sequentially stacked.
In one embodiment, anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. The anode material specifically comprises: 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 oxidation Examples of the material include ZnO: al and SnO 2 : sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Also preferably, a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. In one embodiment, the first hole transport layer 321 consists of the compound HT-1; in another embodiment, the first hole transport layer 321 is composed of the compound HT-20.
In one embodiment, second hole transport layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers or other types of compounds, as not particularly limited herein. In one embodiment, second hole transport layer 322 is comprised of compound HT-19.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 may be specifically selected from any one or a combination of any two or more of the compounds shown below:
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In this application, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may further include a material selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited herein. In one embodiment, electron transport layer 350 is comprised of a combination of compounds ET-2 and LiQ; in another embodiment, the electron transport layer 350 is composed of a compound LiQ and an organic compound of the present application.
In this application, the organic electroluminescent layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic electroluminescent layer 330 is composed of a host material and a guest material, and holes injected into the organic electroluminescent layer 330 and electrons injected into the organic electroluminescent layer 330 may be combined at the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic electroluminescent layer 330 may be a metal chelating compound, bisstyryl derivative, aromatic amine derivative, dibenzofuran derivative or other types of materials, and in one embodiment, the host material of the organic electroluminescent layer 330 is composed of the organic compound of the present application; in another embodiment, the host material of the organic electroluminescent layer consists of the compound BH-01.
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. In one embodiment, the guest material is compound BD-01.
In one embodiment, the cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. In particular, specific examples of cathode materials 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; multilayer materials such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. Preferably, a metal electrode containing silver and magnesium is used as the cathode.
In this application, as shown in fig. 1, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
In some embodiments of the present application, hole injection layer 310 may be composed of F4-TCNQ.
In one embodiment, as shown in fig. 1, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. Electron injection layer 360 may include, but is not limited to, the following compounds:
in one embodiment, the electron injection layer 360 may include ytterbium (Yb); in another embodiment, the electron injection layer 360 may include a compound LiQ.
In one embodiment, as shown in FIG. 1, an organic overlayer 370 may also be provided on the cathode 200, the organic overlayer 370 comprising the compound CP-05.
A third aspect of the present application provides an electronic device comprising the organic electroluminescent device provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is an electronic device 400, and the electronic device 400 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 synthesis method of the nitrogen-containing compound of the present application is specifically described below with reference to synthesis 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.
Synthesis of intermediate A-1
To a 500mL round bottom flask that was dried and replaced with nitrogen was added 9, 10-dibromoanthracene (33.1 g,98.4 mmol), phenylboronic acid (10.0 g,82.0 mmol), tetrakis (triphenylphosphine) palladium (1.9 g,1.6 mmol), tetrabutylammonium bromide (5.3 g,16.4 mmol), potassium carbonate (22.7 g,164.0 mmol), toluene (160 mL), ethanol (40 mL), deionized water (40 mL), and the temperature was raised to 75-80℃with stirring for 8h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using dichloromethane/n-heptane in a volume ratio of 1:6 as mobile phase to give intermediate A-1 (15.5 g; 57%) as white crystals.
Synthesis of intermediate A-X
Using the same method as for synthesizing intermediate A-1, reactant A in the following table was used in place of phenylboronic acid to synthesize intermediate A-X in the following table 1, and the structures, product structures and yields of reactant A are shown in Table 1.
TABLE 1
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Synthesis of intermediate C-1
To a dried and nitrogen-purged round bottom flask was added compound SM1 (50.0 g,176.55 mmol), 5-chloro-2-fluorophenylboronic acid (SM 2) (30.78 g,176.55 mmol), tetrakis (triphenylphosphine) palladium (2.04 g,1.76 mmol), tetrabutylammonium bromide (0.56 g,1.76 mmol), potassium carbonate (36.6 g,264.83 mmol), toluene (400 mL), ethanol (200 mL), deionized water (100 mL), and the mixture was warmed to 78 ℃ with stirring for 8h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using methylene chloride/n-heptane as mobile phase to give intermediate B-1 (35.85 g; 61%).
To a dried and nitrogen-substituted round bottom flask was added intermediate B-1 (30 g,90.13 mmol), potassium carbonate (37.37 g,270.4 mmol), N-methylpyrrolidone (300 mL), stirring at 160℃for 2 hours under nitrogen protection, then removing the solvent under reduced pressure, and the crude product obtained was boiled and washed with deionized water and ethanol, dried and purified by silica gel column chromatography using methylene chloride/N-heptane as mobile phase to give intermediate C-1 (15.51 g; 55%).
Synthesis of intermediate B-X and intermediate C-X
Using the same method as for the synthesis of intermediate B-1, compound SM-N in the following table was used in place of compound SM1 and compound SM-P in the following table was used in place of compound SM2, intermediates B-X and C-X in the following table 2 were synthesized, and the structures and total yields of compound SM-N, compound SM-P, intermediate B-X and intermediate C-X are listed in Table 2.
TABLE 2
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Synthesis of intermediate D-1
To a dried and nitrogen-purged round bottom flask was added C-1 (10 g,31.96 mmol), pinacol biborate (9.74 g,38.36 mmol), tris (dibenzylideneacetone) dipalladium (0.29 g,0.32 mmol), X-phos (cas: 564483-18-7,0.26g,0.64 mmol), potassium acetate (9.39 g,95.89 mmol), 1, 4-dioxane (100 mL), and the mixture was warmed to 80℃with stirring for 8h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase to give intermediate D-1 (7.45; 70%).
Synthesis of intermediate D-X
The same procedure as for the synthesis of intermediate D-1 was used, except that intermediate C-X in Table 3 was used in place of C-1, and intermediate D-X in the following table was synthesized, and the structure of intermediate C-X, the structure of intermediate D-X and the yield are shown in Table 3.
TABLE 3 Table 3
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Synthesis of intermediate E-1
To a dried and nitrogen-purged round bottom flask was added D-1 (10.0 g,24.73 mmol), p-chlorobenzeneboronic acid (33.87 g,24.73 mmol), tetrakis (triphenylphosphine) palladium (0.29 g,0.25 mmol), tetrabutylammonium bromide (0.079 g,0.25 mmol), potassium carbonate (5.13 g,37.09 mmol), toluene (80 mL), ethanol (40 mL), deionized water (20 mL), and the mixture was warmed to 78℃with stirring for 8h; then the reaction mixture was cooled to room temperature, deionized water (200 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the crude product obtained was purified by column chromatography on silica gel using dichloromethane/n-heptane as mobile phase to give intermediate E-1 (6.50 g; 66%).
Synthesis of intermediate E-X
The same procedure as for the synthesis of intermediate E-1 was used, except that D-1 was replaced with intermediate D-X in Table 4, p-chlorobenzoic acid was replaced with raw material R, and intermediate E-X in the following Table was synthesized, and the structures and yields of intermediate D-X, compound R and intermediate E-X are shown in Table 4.
TABLE 4 Table 4
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Synthesis of Compound 1
Intermediate A-1 (10 g,30.01 mmol), intermediate D-1 (12.13 g,30.01 mmol), palladium acetate (0.06 g,0.3 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.25 g,0.6 mmol) and potassium carbonate (8.30 g,60.02 mmol) were added to toluene (80 mL), absolute ethanol (40 mL) and deionized water (20 mL), heated to 80℃under nitrogen protection, stirred for 2h and then cooled to room temperature, the reaction solution was dried using water washing, magnesium sulfate was added, and the filtrate was filtered and the solvent was removed under reduced pressure; the crude product was purified by recrystallization using a methylene chloride/n-heptane system to give compound 1 (11.15 g, yield 70%).
Synthesis of Compound X
Using the same method as the synthesis of Compound 1, intermediate A-X in Table 5 below was substituted for intermediate A-1, and intermediate D-X was substituted for intermediate D-1 to synthesize Compound X in the following table, and the structures and yields of intermediate D-X, intermediate A-X and Compound X are shown in Table 5.
TABLE 5
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Synthesis of Compound 619
To a dried and nitrogen-purged 100mL round bottom flask was added intermediate A-1 (10 g,30.0 mmol), intermediate E-1 (11.95 g,30.01 mmol), tetrakis (triphenylphosphine) palladium (0.35 g,0.3 mmol), tetrabutylammonium bromide (0.10 g,0.3 mmol), potassium carbonate (6.22 g,45.01 mmol), toluene (80 mL), ethanol (40 mL), deionized water (20 mL), and the mixture was warmed to 80℃with stirring for 12h; then the reaction mixture was cooled to room temperature, deionized water (20 mL) was added, stirring was performed for 20 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a mobile phase, followed by recrystallization purification using n-heptane/toluene as a solvent, to obtain a white crystalline compound 619 (10.38 g, 57%).
Synthesis of Compound Y
Using the same method as for the synthesis of compound 619, intermediate A-X in Table 6 below was substituted for intermediate A-1, intermediate E-X was substituted for intermediate E-1, and compound Y in the following table was synthesized, and the structures and yields of intermediate A-X, intermediate E-X and compound Y are shown in Table 6.
TABLE 6
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Synthesis of compound 653:
2-bromo-9, 10-diphenylanthracene (10 g,24.42 mmol), intermediate D-1 (9.88 g,24.42 mmol), palladium acetate (0.05 g,0.24 mmol), 2-dicyclohexylphosphorus-2 ',4',6' -triisopropylbiphenyl (0.20 g,0.49 mmol) and potassium carbonate (6.75 g,48.85 mmol) were added to toluene (80 mL), absolute ethanol (40 mL) and deionized water (20 mL), heated to 80℃under nitrogen protection, stirred for 2 hours and then cooled to room temperature, the reaction solution was dried using water washing, magnesium sulfate was added, and the filtrate was removed under reduced pressure after filtration; the crude product was purified by recrystallization from a methylene chloride/n-heptane system to give compound 653 (9.78 g, yield 66%).
Synthesis of Compound Z
Using the same method as the synthesis of compound 653, the following Table 7 shows that reactant A replaces 2-bromo-9, 10-diphenylanthracene, intermediate D-X replaces D-1 to synthesize compound Z in the following Table, and the structure of intermediate D-X, the structure of reactant A, and the structure and yield of compound Z are shown in Table 7.
TABLE 7
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Synthesis of Compound 658
To a 100mL round bottom flask that was dried and replaced with nitrogen was added 2-bromo-9, 10-diphenylanthracene (10.0 g,24.47 mmol), E-1 (9.75 g,24.47 mmol), tetrakis (triphenylphosphine) palladium (0.29 g,0.24 mmol), tetrabutylammonium bromide (0.08 g,0.24 mmol), potassium carbonate (5.07 g,36.72 mmol), toluene (80 mL), ethanol (40 mL), deionized water (20 mL), and the mixture was warmed to 78℃with stirring and maintained for 12h; then the reaction mixture was cooled to room temperature, deionized water (20 mL) was added, stirring was performed for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a mobile phase, followed by recrystallization purification using methylene chloride/n-heptane as a solvent to obtain compound 658 (9.53 g, 57%).
Synthesis of Compound W
Using the same method as for the synthesis of compound 658, compound W in Table 8 was synthesized with reactant A in place of 2-bromo-9, 10-diphenylanthracene and reactant B in place of intermediate E-1, and the structures of reactant A, reactant B, compound W and yields are listed in Table 8.
TABLE 8
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Mass spectrometry analysis was performed on the compounds synthesized above, resulting in the data shown in table 9 below:
TABLE 9
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The nuclear magnetic data of some compounds are shown in table 10 below.
Table 10
Example 1
The anode was prepared by the following procedure: will be of the thickness ofThe ITO substrate (manufactured by Corning) was cut into a size of 40 mm. Times.40 mm. Times.0.7 mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by a photolithography step, and an ultraviolet ozone and O were used 2 ：N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum deposition of F4-TCNQ on an experimental substrate (anode) to form a thickness ofIs deposited on the Hole Injection Layer (HIL) by vacuum evaporation of the compound HT-1 to form a layer having a thickness +.>A first Hole Transport Layer (HTL).
Evaporating a compound HT-19 as a second hole transport layer (EBL) on the HTL to a thickness of
BD-01 was doped simultaneously with Compound 1 as a main component at a film thickness ratio of 100:3 on the EBL to form a film having a thickness ofAn organic electroluminescent layer (EML).
The ET-2 and LiQ were vapor deposited on the EML at a film thickness 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 magnesium (Mg) and silver (Ag) are mixed at 1: film thickness ratio of 9 was deposited on the electron injection layer by vacuum evaporation to a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAnd (3) forming an organic capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Examples 2 to 45
An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound shown in table 12 below was substituted for the compound 1 at the time of forming the organic electroluminescent layer.
Comparative example 1
An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound a shown in table 11 below was substituted for the compound 1 at the time of forming the organic electroluminescent layer.
Comparative example 2
An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound B shown in table 11 below was substituted for the compound 1 at the time of forming the organic electroluminescent layer.
Comparative example 3
An organic electroluminescent device was fabricated by the same method as in example 1, except that compound C shown in table 11 below was substituted for compound 1 at the time of forming an organic electroluminescent layer.
The material structures used in the above examples and comparative examples are shown in table 11 below:
TABLE 11
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The device performance was analyzed under the conditions and the results are shown in table 12.
Table 12
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From the results of Table 12, it is understood that examples 1 to 45 using the organic compound of the present application as a light-emitting host material and comparative examples 1 to 3 using the known compound as a light-emitting host material, the driving of the above-mentioned organic electroluminescent device produced using the organic compound of the present application as an organic electroluminescent layer, the current efficiency (Cd/A) was improved by at least 12.6%, and the lifetime was improved by at least 15.6%.
Example 46
The anode was prepared by the following procedure: will be of the thickness ofThe ITO substrate (manufactured by Corning) was cut into a size of 40 mm. Times.40 mm. Times.0.7 mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by a photolithography step, and an ultraviolet ozone and O were used 2 ：N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum evaporating F4-TCNQ on experimental substrate (anode) to obtain a thickness ofIs formed by vapor deposition of HT-20 on a Hole Injection Layer (HIL) to a thickness of +.>Is a first hole transport layer (HTL 1).
Vacuum evaporating compound HT-19 on the first hole transport layer to form a film having a thickness ofIs a second hole transport layer (HTL 2).
On the second hole transport layer, BH-01:BD-01 was co-deposited at a deposition rate ratio of 97:3%, to form a layer having a thickness ofBlue organic electroluminescent layer (EML).
Compound 114 and LiQ were mixed in a weight ratio of 1:1 and evaporated to formA thick Electron Transport Layer (ETL), liQ is evaporated on the electron transport layer to form a thickness +.>Then mixing magnesium (Mg) and silver (Ag) at a vapor deposition rate of 1:9, vacuum evaporating on the electron injection layer to form a film with a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAnd an organic capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.
Examples 47 to 61
An organic electroluminescent device was fabricated by the same method as in example 46, except that the compound shown in table 14 below was substituted for the compound 1 at the time of forming the electron transport layer.
Comparative examples 4 to 5
An organic electroluminescent device was fabricated by the same method as in example 46, except that compound D, compound E and compound F shown in table 13 were used instead of compound 1, respectively, in the formation of the electron transport layer.
The material structures used in the above examples and comparative examples are shown in the following table:
TABLE 13
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For the organic electroluminescent device prepared as above, the temperature was 10mA/cm 2 The photoelectric properties of the device were analyzed under the condition of 20mA/cm 2 The device lifetime performance was analyzed under the conditions of (a) and the results are shown in table 14.
TABLE 14
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As can be seen from the data in table 14, when examples 46 to 61 were compared with comparative examples 4 to 5 and the other layers of the device were the same, the current efficiency was improved by at least 10.3% and the lifetime was improved by at least 14.5% when the organic compound of the present application was used as an electron transport material, compared with the compound D and the compound E.
Therefore, when the organic compound is used as an electron transport layer for preparing an organic electroluminescent device, the service life of the organic electroluminescent device can be effectively prolonged, and the luminous efficiency or the driving voltage can be improved to a certain extent.
Other embodiments of the present application will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of the application following, in general, the principles of the application and including such departures from the present disclosure as come within known or customary practice within the art to which the application pertains. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the application being indicated by the following claims.
It is to be understood that the present application is not limited to the precise arrangements and instrumentalities shown in the drawings, which have been described above, and that various modifications and changes may be effected without departing from the scope thereof. The scope of the application is limited only by the appended claims.

Claims (10)

1. An organic compound, characterized in that the structure of the organic compound is shown in formula 1:
wherein Y has a structure shown in formula 2, and the structure shown in formula 3 is condensed at any two adjacent positions in formula 2, and the structure is represented by a connection point where formula 2 and formula 3 are condensed with each other;
each R is 4 The same or different, each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, and substituted or unsubstituted phenyl;
each R is 4 The substituents of (a) are selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl;
L 1 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 triazinylene group, and a substituted or unsubstituted carbazolylene group;
L 2 and L 3 The same or different are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;
L 1 、L 2 And L 3 The substituents in (a) are the same or different and are each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, biphenyl, and phenyl;
ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted:
ar is the same or different and is each independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl;
each R is 5 The same or different are respectively and independently selected from hydrogen or deuterium;
n 1 representation ofNumber n of (n) 1 Selected from 0, 1 or 2;
n 2 representation ofNumber n of (n) 2 Selected from 1 or 2;
n 4 r represents 4 Number n of (n) 4 Selected from 1, 2 or 3, when n 4 When the number is greater than 1, any two R 4 The same or different;
n 5 r represents 5 Number n of (n) 5 Selected from 1, 2, 34, 5, 6, 7 or 8, when n 5 When the number is greater than 1, any two R 5 The same or different.
2. The organic compound according to claim 1, wherein the structure of the organic compound represented by formula 1 is selected from the structures represented by formulas 1-1, 1-2, 1-3 or 1-4:
wherein in the formulae 1-2 and 1-3, each L 1 The Ar is the same or different.
3. The organic compound according to claim 1, wherein Ar is selected from the group consisting of substituted or unsubstituted groups V, unsubstituted groups V being selected from the group consisting of:
wherein,,represents a chemical bond; the substituted group V contains one or more substituents, each of which is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl; and when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
4. The organic compound according to claim 1, wherein Y is selected from the group consisting of:
5. the organic compound according to claim 1, wherein Y is selected from the group consisting of:
6. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
7. an organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound according to any one of claims 1 to 6.
8. The organic electroluminescent device of claim 7, wherein the functional layer comprises an organic electroluminescent layer comprising the organic compound.
9. The organic electroluminescent device of claim 7, wherein the functional layer comprises an electron transport layer comprising the organic compound.
10. An electronic device comprising an organic electroluminescent device as claimed in any one of claims 7 to 9.
CN202210173126.3A 2022-02-24 2022-02-24 Organic compound, organic electroluminescent device and electronic device Active CN115490655B (en)

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