CN117510480A - Organic compound, organic electroluminescent device and electronic device - Google Patents

Organic compound, organic electroluminescent device and electronic device Download PDF

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CN117510480A
CN117510480A CN202311443863.1A CN202311443863A CN117510480A CN 117510480 A CN117510480 A CN 117510480A CN 202311443863 A CN202311443863 A CN 202311443863A CN 117510480 A CN117510480 A CN 117510480A
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王亚龙
杨敏
魏成
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Shaanxi Lighte Optoelectronics Material Co Ltd
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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 is used as the main material of the organic light-emitting layer, can effectively reduce the driving voltage of the organic electroluminescent device, improve the light-emitting efficiency and prolong the service life of the organic electroluminescent device.

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
Since 1987, organic light-emitting diodes (OLEDs) have become a well-known next-generation flat panel display technology. OLEDs are self-luminescent devices in which when charges (electrons and holes) are injected into an organic film between an anode and a cathode, the electrons and holes recombine to form excitons and transfer energy to a light-emitting molecule, thereby exciting electrons to transition from a ground state to an excited state, and the excited state energy is deactivated by radiation to emit light. OLEDs have the advantages of self-luminescence, low driving voltage, light weight, wide luminous visual angle, high response speed, bending and folding performances, low energy consumption, large-area production and the like, so that the OLEDs have wide application prospects in the fields of information display and solid-state illumination. The traditional organic fluorescent material can only emit light by using 25% singlet excitons formed by electric excitation, and the internal quantum efficiency of the device is low (25% at maximum). External quantum efficiency is generally lower than 5%, and there is a great gap from the efficiency of phosphorescent devices. The phosphorescent material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%.
The prior art discloses host materials that can be used to prepare organic light-emitting layers in organic electroluminescent devices. However, there is still a need to continue to develop new materials to further improve the performance of organic electroluminescent devices.
Disclosure of Invention
The present application aims to overcome the defects in the prior art, and provide an organic compound, an organic electroluminescent device and an electronic device comprising the same, wherein the organic compound can reduce driving voltage, 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 is selected from O or S;
L 1 and L 2 Identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, orA substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
X 1 、X 2 and X 3 Identical or different and are each independently selected from N or C (H), and X 1 、X 2 And X 3 At least one of which is N;
R 1 、R 2 、R 3 and R is 4 The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
R 5 selected from aryl groups with 6-30 carbon atoms or heteroaryl groups with 3-30 carbon atoms;
R a and R is b The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
n a r represents a Number n of (2) a Selected from 0, 1,2, 3 or 4, when n a When the number is greater than 1, each R a The same or different;
n b r represents b Number n of (2) b Selected from 0, 1,2 or 3, when n b When the number is greater than 1, each R b The same or different;
L 1 、L 2 、Ar 1 and Ar is a group 2 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, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms.
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 third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
The structures of the organic compounds of the present application include dibenzofuranyl and triazinyl heteroaryl groups with benzofuran/benzothiophene. And the 1-position of benzofuran/benzothiophene is linked to the dibenzofuranyl group. The three groups have a specific connection mode, can improve the carrier transmission characteristic and the energy transfer characteristic of the compound, can effectively improve the luminous efficiency of a device when being used as a main material of an organic luminous layer, and meanwhile, the organic compound has good thermal stability and improves the service life to a certain extent.
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 hole transport layer; 322. a light emission adjustment layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. an electronic device.
Specific embodiments thereof have been shown by way of example in the drawings and will herein be described in more detail. These drawings and the written description are not intended to limit the scope of the inventive concepts in any way, but to illustrate the concepts of the present application to those skilled in the art by reference to specific embodiments.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
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 is selected from O or S;
L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
X 1 、X 2 and X 3 Identical or different and are each independently selected from N or C (H), andX 1 、X 2 and X 3 At least one of which is N;
R 1 、R 2 、R 3 and R is 4 The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
R 5 selected from aryl groups with 6-30 carbon atoms or heteroaryl groups with 3-30 carbon atoms;
R a and R is b The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
n a r represents a Number n of (2) a Selected from 0, 1,2, 3 or 4, when n a When the number is greater than 1, each R a The same or different;
n b r represents b Number n of (2) b Selected from 0, 1,2 or 3, when n b When the number is greater than 1, each R b The same or different;
L 1 、L 2 、Ar 1 and Ar is a group 2 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, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms.
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 formula (f), the naphthyl group represented by formula (f) is attached to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) -formula (f-10).
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 side benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formula (X '-1) -formula (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 formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means includes any of the possible linkages as shown in formula (Y-1) -formula (Y-7).
In the present application, L 1 、L 2 、R 1 、R 2 、R 3 、R 4 、R 5 、Ar 1 、Ar 2 、R a And R is b Refers to all carbon number. 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 (Ar) 1 Is thatThe number of carbon atoms is 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 alkyl groups 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 carbon-carbon bonds, a monocyclic aryl group and a condensed ring aryl group connected by carbon-carbon bonds, two or more condensed ring aryl groups connected by carbon-carbon bonds. That is, unless otherwise indicated, two or more aromatic groups linked by carbon-carbon bonds may also be considered aryl groups herein. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. 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, triphenylene, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,Radicals, spirobifluorenyl radicals, and the like. 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, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 18, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 15. For example, in the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may also be 6,7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 or 30 carbon atoms, although other numbers are possible and are not explicitly recited herein. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals, as well as unsubstituted aryl radicals.
In the present application, terphenyl includes
In the present application, the arylene group refers to a divalent group formed by further losing one hydrogen atom of the 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 linked by 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" herein 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 12 to 24, 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, reference to heteroarylene means a divalent group formed by further losing one hydrogen atom from the heteroaryl group.
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 organic compound is selected from structures represented by any one of formulas a to P below:
in some embodiments of the present application, L 1 And L 2 And are identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
In some embodiments of the present application, L 1 And L 2 And are identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or 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 and are each independently selected from single bonds, having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 1 carbon atoms6. 17 or 18, or a substituted or unsubstituted arylene group having 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
Alternatively, 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 aryl group having 6 to 12 carbon atoms.
In other embodiments of the present application, L 1 And L 2 And are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazole group.
Alternatively, L 1 And L 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 or phenyl.
In some embodiments of the present application, L 1 And L 2 Identical or different, and are each independently selected from a single bond, a substituted or unsubstituted group V, wherein the unsubstituted group V is 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 Identical or different and are each independently selected from the group consisting of single bonds 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 or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
Alternatively, 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 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.
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, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.
Alternatively, 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 group, cyano group, alkyl group having 1 to 5 carbon atoms or aryl group having 6 to 12 carbon atoms.
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 substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.
Alternatively, 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 or phenyl.
Alternatively, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the group consisting of:
specifically, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the group consisting of:
in some embodiments of the present application,identical or different and are each independently selected from the group consisting of:
in particular, the method comprises the steps of,identical or different and are each independently selected from the group consisting of: />
In some embodiments of the present application, R 1 、R 2 、R 3 And R is 4 And are the same or different and are each independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 5 carbon atoms, or phenyl.
R 5 Selected from aryl groups having 6 to 20 carbon atoms.
Further alternatively, R 5 Selected from phenyl, naphthyl, biphenyl or terphenyl.
In other embodiments of the present application, R 1 、R 2 、R 3 And R is 4 And are the same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms, or phenyl groups.
In other embodiments of the present application, R 5 Selected from the group consisting of:
specifically, R 1 、R 2 、R 3 And R is 4 The same or different and are each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In some embodiments of the present application, R 5 Selected from the group consisting of:
in some embodiments of the present application, R 5 Selected from phenyl, naphthyl, biphenyl or terphenyl; r is R 1 、R 2 、R 3 And R is 4 Are hydrogen or deuterium.
In some embodiments of the present application, R a And R is b And are the same or different and are each independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms.
Alternatively, R a And R is b The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl or terphenyl.
In some embodiments of the present application, n a And n b All 0.
In the present application, "X 1 、X 2 And X 3 In (a) and (b)At least one of N' means X 1 、X 2 And X 3 Any one of which is N; alternatively, X 1 、X 2 And X 3 Any two of which are N; alternatively, X 1 、X 2 And X 3 Are all N.
Alternatively, X 1 Is N, X 2 And X 3 C (H); or X 2 Is N, X 1 And X 3 C (H); or X 3 Is N, X 1 And X 2 C (H); or X 1 And X 2 Is N, X 3 C (H); or X 1 And X 3 Is N, X 2 C (H); or X 2 And X 3 Is N, X 1 C (H); or X 1 、X 2 And X 3 Are all N.
In some embodiments of the present application, the organic compound is selected from the group consisting of the compounds as set forth in claim 9.
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.
In another embodiment of the present application, the organic electroluminescent device may be, for example, a red organic electroluminescent device.
In another embodiment of the present application, the functional layer comprises an organic light emitting layer comprising the organic compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, a light emission adjustment layer 322, an organic light emitting layer 330, an electron transport layer 340, 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 metals and oxides such as 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 this application, hole transport layer 321 may comprise one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and in one embodiment, hole transport layer 321 is composed of an organic compound HT-1.
In the present application, the light emission adjusting layer 322 may include one or more materials, which may be selected from carbazole multimers or other types of compounds, and the present application is not particularly limited. In one embodiment, the luminescence-adjustment layer 322 is composed of the compound HT-2.
Alternatively, the emission adjustment layer is also referred to as a hole buffer layer, a hole adjustment layer, an electron blocking layer, an emission buffer layer, or a second hole transport layer.
In this application, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, 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 340 is comprised of a combination of compound LiQ and compound ET-1.
In this application, the organic light emitting 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 light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light-emitting layer 330 may be a metal chelate compound, bisstyryl derivative, aromatic amine derivative, dibenzofuran derivative or other type of material, and in one embodiment, the host material of the organic light-emitting layer is composed of the organic compound and the compound PAnd the components are combined together.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. In one embodiment, the guest material consists of compound RD-1.
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 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. In some embodiments of the present application, hole injection layer 310 may be composed of compound PD and compound HT-1.
In one embodiment, as shown in fig. 1, an electron injection layer 350 may also be provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. In one embodiment, the electron injection layer 350 may include ytterbium (Yb).
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 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.
Synthesis of intermediate A-1:
to a dry 500mL round bottom flask under nitrogen was added 3-phenylbenzofuran (10 g,51.48 mmol) and dichloromethane (100 mL), NBS (N-bromosuccinimide) (9.16 g,51.48 mmol) with stirring at room temperature and maintained at stirring for 8h; deionized water (200 mL) was then added to the reaction mixture, and the mixture was stirred for 15 minutes, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give intermediate A-1 (8.01 g, yield 57%).
Synthesis of intermediate C-1:
adding an intermediate A-1 (10 g,36.61 mmol) into a tetrahydrofuran (100 mL) solution, cooling the mixed solution to-78 ℃, dropwise adding an n-butyllithium n-hexane solution (2.81 g,43.93mmol,22mL,2 mol/L), keeping the temperature for 30min, dropwise adding trimethyl borate (5.70 g,54.91 mmol), keeping the temperature for 1h, heating to room temperature, stirring overnight, adding dilute hydrochloric acid (2 mol/L) for neutralization, washing the reaction solution to neutrality, separating an organic phase, adding anhydrous magnesium sulfate for drying, filtering, and removing the solvent from the filtrate under reduced pressure; the crude product was recrystallized from n-heptane to give intermediate C-1 (5.22 g, yield 60%).
Synthesis of intermediate D-1:
/>
to a 250mL three-necked flask under nitrogen atmosphere, intermediate C-1 (10 g,42.00 mmol), SM-1 (11.82 g,42.00 mmol), tetrakis (triphenylphosphine) palladium (0.49 g,0.42 mmol), anhydrous potassium carbonate (11.60 g,84.00 mmol), tetrabutylammonium bromide (0.13 g,0.42 mmol), toluene (80 mL), anhydrous ethanol (40 mL) and deionized water (20 mL) were added sequentially, stirring and heating were turned on, and the temperature was raised to reflux for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded intermediate D-1 (9.12 g, 55% yield).
Referring to the synthesis method of intermediate D-1, in the following Table 1, SM-X was substituted for intermediate SM-1, and intermediate D-X in the following Table was synthesized:
TABLE 1
/>
Synthesis of intermediate E-1:
to a 250mL three-necked flask under nitrogen atmosphere, was added intermediate D-1 (10.00 g,25.32 mmol) dissolved in 1, 4-dioxane (100 mL), followed by tris (dibenzylideneacetone) dipalladium (0.23 g,0.25 mmol), potassium acetate (4.97 g,50.65 mmol), pinacol biborate (6.43 g,25.32 mmol), x-phos (2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl, 0.12g,0.25 mmol), and the mixture was heated to reflux with stirring. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded intermediate E-1 (9.24 g, 75% yield).
Referring to the synthesis method of intermediate E-1, intermediate D-X shown in Table 2 below was synthesized in place of intermediate D-1:
TABLE 2
/>
Synthesis of Compound 7:
to a 250mL three-necked flask under nitrogen atmosphere, intermediate E-1 (10.00 g,20.54 mmol), SN-1 (5.50 g,20.54 mmol), tetrakis (triphenylphosphine) palladium (0.23 g,0.21 mmol), anhydrous potassium carbonate (5.67 g,41.09 mmol), tetrabutylammonium bromide (0.06 g,0.21 mmol), toluene (80 mL), anhydrous ethanol (40 mL) and deionized water (20 mL) were sequentially added, stirring and heating were turned on, and the mixture was warmed to reflux for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded compound 7 (8.87 g, 73% yield).
Referring to the synthesis of compound 7, the following compounds shown in Table 3 were synthesized with E-X substituting for intermediate E-1 and SN-X substituting for SN-1 in Table 3 below:
TABLE 3 Table 3
/>
/>
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Mass spectrometry analysis was performed on the compounds synthesized above, resulting in the data shown in table 4 below:
TABLE 4 Table 4
Compounds of formula (I) Mass spectral data Compounds of formula (I) Mass spectral data
Compound 7 m/z＝592.2[M+H] + Compound 12 m/z＝668.2[M+H] +
Compound 5 m/z＝592.2[M+H] + Compound 13 m/z＝668.2[M+H] +
Compound 20 m/z＝668.2[M+H] + Compound 23 m/z＝642.2[M+H] +
Compound 36 m/z＝592.2[M+H] + Compound 38 m/z＝668.2[M+H] +
Compound 59 m/z＝592.2[M+H] + Compound 63 m/z＝668.2[M+H] +
Compound 206 m/z＝608.2[M+H] + Compound 208 m/z＝668.2[M+H] +
Compound 47 m/z＝668.2[M+H] + Compound 39 m/z＝668.2[M+H] +
Compound 35 m/z＝592.2[M+H] + Compound 29 m/z＝758.2[M+H] +
Compound 209 m/z＝602.3[M+H] + Compound 210 m/z＝704.3[M+H] +
The nuclear magnetic data of some compounds are shown in table 5 below:
TABLE 5
Example 1: preparation of red organic electroluminescent device
By the followingThe process for preparing the device comprises the steps of forming a thin film on the ITO/Ag/ITOOn the experimental 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 can be used for cleaning the surface of the experimental substrate to remove impurities and greasy dirt on the surface of the experimental substrate.
The compound HT-1 and PD are co-evaporated on an experimental substrate at an evaporation rate ratio of 98 percent to 2 percent to form a film with the thickness ofThen evaporating a compound HT-1 on the hole injection layer to form a layer having a thickness +.>Is provided.
Evaporating a compound HT-2 on the hole transport layer to form a film having a thickness ofIs provided.
On the luminescence adjusting layer, compound P (P-type doped body), compound 7 (N-type doped body) and RD-1 are co-evaporated at the evaporation rate ratio of 60 percent to 40 percent to 2 percent to form the light-emitting diode with the thickness ofIs provided.
On the organic light-emitting layer, the compound ET-1 and LiQ are co-evaporated at the evaporation rate ratio of 50% to form a film with the thickness ofIs provided.
Evaporating Yb on the electron transport layer to form a layer of thicknessElectron injection layer of (a); then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10% to 90% to form a film having a thickness of +.>Is provided.
Finally, the compound CP-1 is evaporated on the cathode to form a film with the thickness ofThereby completing the preparation of the red organic electroluminescent device. />
Examples 2 to 18
An organic electroluminescent device was prepared by the same method as in example 1, except that in preparing the organic light-emitting layer, compound 7 was replaced with the compound in table 7 below.
Comparative examples 1 to 3
An organic electroluminescent device was prepared by the same method as in example 1, except that in preparing the organic light emitting layer, compound 7 was replaced with compound a, compound B or compound C in table 6 below.
The material structures used in the above examples and comparative examples are shown in table 6 below:
TABLE 6
Performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 18 and comparative examples 1 to 3, specifically at 10mA/cm 2 Under the condition of testing IVL performance of the device, T 95 The service life of the device is 20mA/cm 2 The test results are shown in table 7 below.
TABLE 7
As can be seen from table 7 above, examples 1 to 18, in which the compounds of the present application were used as the organic light-emitting layer host materials, had a voltage drop of at least 0.24V, a current efficiency of at least 32.7%, and a device lifetime of at least 18.5% as compared with comparative examples 1 to 3. Therefore, the organic compound is used for the organic light-emitting layer of the organic electroluminescent device, can reduce the device voltage, and can improve the light-emitting efficiency and T of the organic electroluminescent device 95 And (5) service life.

Claims (12)

1. An organic compound, characterized in that the structure of the organic compound is shown as formula 1:
wherein Y is selected from O or S;
L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
X 1 、X 2 and X 3 Identical or different and are each independently selected from N or C (H), and X 1 、X 2 And X 3 At least one of which is N;
R 1 、R 2 、R 3 and R is 4 The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
R 5 selected from the group consisting of carbon atomsAryl groups of 6 to 30 or heteroaryl groups of 3 to 30 carbon atoms;
R a and R is b The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms or heteroaryl groups having 3 to 30 carbon atoms;
n a r represents a Number n of (2) a Selected from 0, 1,2, 3 or 4, when n a When the number is greater than 1, each R a The same or different;
n b r represents b Number n of (2) b Selected from 0, 1,2 or 3, when n b When the number is greater than 1, each R b The same or different;
L 1 、L 2 、Ar 1 and Ar is a group 2 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, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms or cycloalkyl having 3 to 10 carbon atoms.
2. The organic compound according to claim 1, wherein L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms;
alternatively, 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 aryl group having 6 to 12 carbon atoms.
3. The organic compound according to claim 1, wherein L 1 And L 2 And are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, and a substituted or unsubstitutedSubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, or substituted or unsubstituted carbazolylene;
alternatively, L 1 And L 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 or phenyl.
4. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms;
alternatively, 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 group, cyano group, alkyl group having 1 to 5 carbon atoms or aryl group having 6 to 12 carbon atoms.
5. The organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group;
alternatively, 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 or phenyl.
6. The organic compound according to claim 1, wherein,identical or different and are each independently selected from the group consisting of:
7. the organic compound according to claim 1, wherein R 1 、R 2 、R 3 And R is 4 The same or different and are each independently selected from hydrogen, deuterium, cyano, halogen groups, alkyl groups having 1 to 5 carbon atoms or phenyl groups;
R 5 selected from the group consisting of:
8. the organic compound according to claim 1, wherein n a And n b All 0.
9. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
10. 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 9.
11. The organic electroluminescent device of claim 10, wherein the functional layer comprises an organic light-emitting layer comprising the organic compound.
12. Electronic device, characterized in that it comprises an organic electroluminescent device as claimed in claim 10 or 11.
CN202311443863.1A 2023-11-01 2023-11-01 Organic compound, organic electroluminescent device and electronic device Pending CN117510480A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110317195A (en) * 2018-03-29 2019-10-11 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN110799499A (en) * 2017-06-30 2020-02-14 株式会社斗山 Organic compound and organic electroluminescent element comprising same
CN111018847A (en) * 2019-10-31 2020-04-17 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic component, and electronic device
CN111303134A (en) * 2020-03-25 2020-06-19 烟台显华化工科技有限公司 Organic light-emitting material and organic electroluminescent device
CN116640126A (en) * 2023-05-29 2023-08-25 长春海谱润斯科技股份有限公司 Organic electroluminescent compound and organic electroluminescent device thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110799499A (en) * 2017-06-30 2020-02-14 株式会社斗山 Organic compound and organic electroluminescent element comprising same
CN110317195A (en) * 2018-03-29 2019-10-11 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN111018847A (en) * 2019-10-31 2020-04-17 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic component, and electronic device
CN111303134A (en) * 2020-03-25 2020-06-19 烟台显华化工科技有限公司 Organic light-emitting material and organic electroluminescent device
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