CN113105462B - Organic compound, and electronic element and electronic device using same - Google Patents

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

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CN113105462B
CN113105462B CN202110313722.2A CN202110313722A CN113105462B CN 113105462 B CN113105462 B CN 113105462B CN 202110313722 A CN202110313722 A CN 202110313722A CN 113105462 B CN113105462 B CN 113105462B
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CN113105462A (en
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贾志艳
郭炯
金荣国
李应文
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Shaanxi Lighte Optoelectronics Material Co Ltd
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Abstract

The application relates to an organic compound, the structure of which is shown in formula 1, and when the organic compound is used as a hole adjusting layer material of an electronic element, the organic compound can reduce driving voltage, improve the luminous efficiency of the device and prolong the service life of the device.
Figure DDA0002990959990000011

Description

Organic compound, and electronic element and electronic device using same
Technical Field
The application belongs to the technical field of organic materials, and particularly provides an organic compound, and an electronic element and an electronic device using the organic compound.
Background
The organic electroluminescent device technology is considered as a next generation display and illumination technology due to the advantages of active light emission, high luminous efficiency, low power consumption, lightness, thinness, high response speed, large visual angle and the like. The organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a luminescent layer, an electron transport layer, a hole blocking layer, an electron injection layer, a cathode and the like. Electrons and holes are injected from the cathode and the anode, respectively, and then recombined in the light emitting layer through the electron transport layer and the hole transport layer to form excitons, which return to the ground state to emit light.
Although the OLED has been widely used, due to the scarcity of excellent transmission materials, efficient light emitting materials and injection materials, the properties of the OLED device, such as light emitting efficiency and service life, are still to be further improved compared with the application requirements of the product.
Disclosure of Invention
An object of the present application is to provide an organic compound which can be used in an electronic element to improve light-emitting properties and a lifetime of the electronic element, and an electronic element and an electronic device using the same.
In order to achieve the above object, a first aspect of the present application provides an organic compound having a structure represented by chemical formula 1:
Figure BDA0002990959970000011
wherein R is1Selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted cycloalkyl with 3-10 carbon atoms;
R2、R3、R4and R5Are identical or different from one another and are each independently selected from the group A or
Figure BDA0002990959970000012
And R is2、R3、R4And R5Is selected from
Figure BDA0002990959970000013
Wherein the content of the first and second substances,
Figure BDA0002990959970000014
represents a chemical bond;
the group A is selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms, an aryl group with 6-12 carbon atoms, a heteroaryl group with 3-12 carbon atoms and a trialkylsilyl group with 3-12 carbon atoms;
n2～n5with ntIs represented by R2～R5With RtIs represented by t is a variable and is an arbitrary integer of 2 to 5, ntRepresents a substituent RtThe number of (2); when t is 2, 3 or 5, ntSelected from 0, 1,2, 3; when t is 4, ntSelected from 0, 1,2, 3, 4; when n istWhen greater than 1, any two RtThe same or different;
L1and L are 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;
Ar1and Ar2The same or different from each other, and each is 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;
the R is1、L1、L、Ar1And Ar2Wherein the substituents are independently selected from deuterium, cyano, halogen group, alkyl group having 1-10 carbon atoms, aryl group having 6-20 carbon atoms, heteroaryl group having 3-20 carbon atoms, and trialkylsilyl group having 3-12 carbon atoms; optionally, at Ar1And Ar2Any two adjacent substituents form a 3-15 membered saturated or unsaturated ring.
A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode;
the functional layer comprises an organic compound provided in the first aspect of the present application;
preferably, the functional layer includes a hole-adjusting layer containing the organic compound;
preferably, the functional layer includes a hole transport layer containing the organic compound.
A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application; preferably, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
The organic compound has a structure containing two carbazole condensed rings, has a larger rigid planar structure, can greatly improve the hole mobility of the material, and simultaneously, the arylamine and the two carbazole structures are connected in a specific position, so that the material has a better spatial configuration, the crystallization tendency among material molecules is reduced, and the film forming property of the material is improved. And secondly, the organic electroluminescent material has a shallow LUMO energy level and a high T1 energy level, can well block electrons or excitons, and improves the recombination rate of holes and electrons. Therefore, the organic compound can be used as a second hole transport layer (an electron blocking layer) in a red light device, can effectively balance charge transport, reduce the voltage of the device, and improve the current efficiency and the service life of the device.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of a first electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
Description of the reference numerals
100. Anode 200, cathode 300, functional layer 310, hole injection layer
320. First hole transport layer 321, second hole transport layer 322, hole adjustment layer 330, organic light emitting layer
340. Electron transport layer 350, electron injection layer 360, photoelectric conversion layer 400, first electronic device
500. Second electronic device
Detailed Description
The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.
The terms "the" and "said" are used to indicate the presence of one or more elements/components/etc.; the terms "comprises," "comprising," and "including" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.
In a first aspect, the present application provides an organic compound having a structure represented by chemical formula 1:
Figure BDA0002990959970000031
wherein R is1Selected from substituted or unsubstituted aryl with 6-30 carbon atoms, substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted cycloalkyl with 3-10 carbon atoms;
R2、R3、R4and R5Are identical or different from one another and are each independently selected from the group A or
Figure BDA0002990959970000032
And R is2、R3、R4And R5Is selected from
Figure BDA0002990959970000033
Wherein, the first and the second end of the pipe are connected with each other,
Figure BDA0002990959970000034
represents a chemical bond;
the group A is selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms, an aryl group with 6-12 carbon atoms, a heteroaryl group with 3-12 carbon atoms and a trialkylsilyl group with 3-12 carbon atoms;
n2～n5with ntIs represented by R2～R5With RtIs represented by t is a variable and is an arbitrary integer of 2 to 5, ntRepresents a substituent RtThe number of (2); when t is 2, 3 or 5, ntSelected from 0, 1,2, 3; when t is 4, ntSelected from 0, 1,2, 3, 4; when n istWhen greater than 1, any two RtThe same or different;
L1and L are 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;
Ar1and Ar2Are the same or different from each other and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted aryl group having 3 to 30 carbon atomsThe heteroaryl group of (a);
the R is1、L1、L、Ar1And Ar2Wherein the substituents are independently selected from deuterium, cyano, halogen group, alkyl group having 1-10 carbon atoms, aryl group having 6-20 carbon atoms, heteroaryl group having 3-20 carbon atoms, and trialkylsilyl group having 3-12 carbon atoms; optionally, in Ar1And Ar2In (b), any two adjacent substituents form a 3-15 membered saturated or unsaturated ring, for example, any two adjacent substituents form a cyclopentyl group, a cyclohexyl group, etc.
In this application, "optionally, at Ar1And Ar2Wherein any two adjacent substituents form a 3-15 membered ring "means that in Ar1And Ar2Any two adjacent substituents may or may not form a 3-15 membered ring.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,') "
Figure BDA0002990959970000035
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having a substituent Rc. Wherein Rc as the substituent may be, for example, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trimethylsilyl group, an arylsilyl group having 8 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, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms or a phosphinyloxy group having 6 to 18 carbon atoms. In the present application, a "substituted" functional group may be substituted with one or 2 or more substituents in the above Rc; when two substituents Rc are attached to the same atom, these two substituents Rc may be independently present or attached to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent two substituents Rc may exist independently or may form a ring fused with the functional group to which they are attached. Optionally, any two of the substituents described above in this application may be linked to each other to form, together with the atoms to which they are attached, a 3-15 membered saturated or 3-15 membered unsaturated ring.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12. For example: l is
Figure BDA0002990959970000041
The number of carbon atoms is 12. As another example, Ar1Is composed of
Figure BDA0002990959970000042
The number of carbon atoms is 10.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, P, Si or Se or the like is included in one functional group and the remaining atoms are carbon and hydrogen.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, and numerical ranges such as "1 to 10" refer herein to each integer in the given range; for example, "alkyl of 1 to 10 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms.
Preferably, 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, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
Figure BDA0002990959970000043
and the like. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 20, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 15. For example, the number of carbon atoms in the aryl group can be 6, 12, 13, 14, 15, 18, 20, 24, 25, 30, or other numbers, as described hereinAre not listed any more. In the present application, biphenyl is understood to mean phenyl-substituted aryl radicals and also unsubstituted aryl radicals.
In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, the substituted aryl group may be an aryl group in which one or two or more hydrogen atoms are substituted with a group such as a deuterium atom, a halogen group, a cyano group, a tert-butyl group, a trifluoromethyl group, a heteroaryl group, a trimethylsilyl 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 in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.
In the present application, as the aryl group as the substituent, specific examples include, but are not limited to: phenyl, naphthyl, anthracyl, phenanthryl, dimethylfluorenyl, biphenyl, carbazolyl, and the like.
In the present application, heteroaryl refers to a monovalent aromatic ring containing 1,2, 3,4, 5, 6, or 7 heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se, and S, or derivatives thereof. The heteroaryl group can be monocyclic heteroaryl or polycyclic heteroaryl, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems which are connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, 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. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. The "heteroaryl" group herein may contain 3 to 30 carbon atoms, in some embodiments the number of carbon atoms in the heteroaryl group may be 5 to 24, in other embodiments the number of carbon atoms in the heteroaryl group may be 3 to 20, and in other embodiments the number of carbon atoms in the heteroaryl group may be 3 to 15. For example, the number of carbon atoms may be 3,4, 5, 7, 12, 13, 15, 18, 20, 24, 25 or 30, and of course, other numbers may be used, which are not listed here.
In this application, reference to heteroarylene means a divalent radical formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trimethylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, specific examples of the heteroaryl group as the substituent include, but are not limited to: pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
Figure BDA0002990959970000051
It means that one end of the connecting key can be connected to the one through which the key passesAt any position in the ring system, the other end is attached to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) and the formula (f-10) includes any possible connection mode shown in the formula (f-1) and the formula (f-10).
Figure BDA0002990959970000052
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, and the meaning thereof includes any of the possible attachment means as shown in the formulas (X '-1) -formula (X' -4).
Figure BDA0002990959970000061
The meaning of the connection or substitution is the same as that of the connection or substitution, and will not be described further.
In one embodiment of the present application, the organic compound has a structure as shown below:
Figure BDA0002990959970000062
in one embodiment of the present application, the group a is selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, quinolinyl, isoquinolinyl, dibenzothienyl, dibenzofuranyl, carbazolyl, trimethylsilyl.
In one embodiment of this application, R is1Selected from substituted or unsubstituted aryl with 6-15 carbon atoms, substituted or unsubstituted heteroaryl with 5-12 carbon atoms, and substituted or unsubstituted aryl with 3-10 carbon atomsSubstituted cycloalkyl groups.
In one embodiment of the present application, R is1Selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
Figure BDA0002990959970000063
wherein the content of the first and second substances,
Figure BDA0002990959970000064
represents a bond, and when group W is substituted with one or more substituents, each of said substituents is independently selected from: deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl.
In one embodiment of the present application, R is1Selected from the group consisting of:
Figure BDA0002990959970000065
in one embodiment of the present application, Ar is1And Ar2The same or different from each other, and each is 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 18 carbon atoms;
optionally, the Ar is1And Ar2Wherein the substituents are the same or different from each other and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, pyridyl, phenyl, naphthyl, biphenyl, carbazolyl, optionally, at Ar1And Ar2Wherein any two adjacent substituents form a fluorene ring.
In one embodiment of the present application, Ar is1And Ar2Are the same or different from each other, and are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstitutedSubstituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
In one embodiment of the present application, Ar is1And Ar2Identical to or different from each other and each independently selected from the group V, which is unsubstituted or substituted, selected from the group consisting of:
Figure BDA0002990959970000071
wherein the content of the first and second substances,
Figure BDA0002990959970000072
represents a chemical bond; when the group V is substituted with one or more substituents, each of the substituents is independently selected from: deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, pyridyl, phenyl, naphthyl, biphenyl, carbazolyl.
In a specific embodiment of the present application, Ar1And Ar2Are the same or different from each other and are each independently selected from the group consisting of:
Figure BDA0002990959970000073
in one embodiment of the present application, L and L1The same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms;
in one embodiment of the present application, L and L1The same or different, and each is 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;
optionally, the L and L1Wherein the substituents are the same or differentAnd each is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl.
In one embodiment of the present application, L and L1Identical or different and are each independently selected from a single bond or a substituted or unsubstituted group T selected from the group consisting of:
Figure BDA0002990959970000081
when said group T is substituted with one or more substituents, the substituents of group T are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl.
In one embodiment of the present application, L and L1The same or different and each is independently selected from the group consisting of a single bond or the following groups:
Figure BDA0002990959970000082
in one embodiment of the present application, the organic compound is selected from the following organic compounds:
Figure BDA0002990959970000083
Figure BDA0002990959970000091
Figure BDA0002990959970000101
Figure BDA0002990959970000111
Figure BDA0002990959970000121
Figure BDA0002990959970000131
Figure BDA0002990959970000141
Figure BDA0002990959970000151
Figure BDA0002990959970000161
Figure BDA0002990959970000171
a second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound as provided in the first aspect of the present application.
In a preferred embodiment of the present application, the functional layer includes a hole-adjusting layer containing the organic compound.
In another preferred embodiment of the present application, the functional layer comprises a first hole transport layer 320, which contains the organic compound.
In one embodiment of the present application, the electronic component is an organic electroluminescent device or a photoelectric conversion device.
In one embodiment of the present application, the electronic component is an organic electroluminescent device, for example a red light device.
In one embodiment of the present application, the electronic component may be an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a second hole transport layer 321, a hole adjusting layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, the anode 100 comprises an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer 300. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the second hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. For example, the second hole transport layer 321 may be composed of a compound NPB.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 330 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfer energy to the dopant material, thereby enabling the dopant material to emit light. The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which is not particularly limited in the present application. Is provided withThe doping material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. For example, the organic light-emitting layer contains CBP and Ir (piq)2(acac)。
Alternatively, 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, which may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In one embodiment of the present application, the electron transport layer 340 may be composed of ET-06 and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the second hole transport layer 321 to enhance the ability to inject holes into the second hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as Yb, an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 350 may contain Yb.
According to another embodiment, the electronic component may be a photoelectric conversion device. As shown in fig. 3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 including an organic compound provided herein, disposed between the anode 100 and the cathode 200.
According to a specific embodiment, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a second hole transport layer 320, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, and particularly may be an organic thin film solar cell. For example, in one embodiment of the present application, a solar cell may include an anode, a hole transport layer, a hole adjusting layer, an organic light emitting layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole adjusting layer includes an organic compound of the present application.
A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned electronic components. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
In another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation apparatus, a light detector, a fingerprint recognition apparatus, a light module, a CCD camera, or other types of electronic devices.
The following will specifically explain the method for synthesizing the organic compound of the present application by referring to the synthesis examples, but the present disclosure is not limited thereto.
Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
Analytical detection of intermediates and compounds in this application uses an ICP-7700 mass spectrometer and an M5000 element analyzer.
Synthesis example of organic Compound
Figure BDA0002990959970000191
A1L three-necked flask was charged with 1-bromo-5-chloro-2-iodo-3-nitrobenzene (50g, 138mmol), 2-chlorophenylboronic acid (21.6g, 138mmol), tetrakis (triphenylphosphine) palladium (3.2g, 2.8mmol), tetrahydrofuran (90 mL), and a 40 wt% aqueous solution of tripotassium phosphate (73.1g, 345mmol), and the mixture was refluxed under nitrogen for 8 hours. After cooling to room temperature, washing with water three times, finally extracting once with saturated aqueous ammonium chloride solution, combining the organic phases, drying with anhydrous magnesium sulfate, and concentrating by rotary evaporation. The obtained solid was recrystallized from ethanol to obtain 30.2g of 2-bromo-2 ', 4-dichloro-6-nitro-1, 1' -biphenyl (intermediate-M-1) (yield 63%).
intermediate-M-X of table 1 was synthesized in the same manner as intermediate-M-1, except that SM-a-X was used instead of 1-bromo-5-chloro-2-iodo-3-nitrobenzene and SM-B-X was used instead of 2-chlorophenylboronic acid, to prepare intermediate-M-X.
TABLE 1
Figure BDA0002990959970000192
Figure BDA0002990959970000201
Figure BDA0002990959970000202
A500 mL three-necked flask was charged with intermediate-M-1 (30.2g, 87mmol), triphenylphosphine (57.1g, 217.5mmol) and o-dichlorobenzene (150 mL), and the reaction mixture was stirred at 150 ℃ for 18 hours. O-dichlorobenzene was distilled under reduced pressure, and the residue was subjected to silica gel column using toluene as an eluent, to obtain 22.8g of 4-bromo-2, 5-dichloro-9H-carbazole (intermediate-N-1) (yield 83%).
The intermediate-N-X of Table 2 was synthesized in the same manner as the intermediate-N-1, except that intermediate-M-X was used instead of intermediate-M-1 to prepare intermediate-N-X.
TABLE 2
Figure BDA0002990959970000203
Figure BDA0002990959970000204
Into a 500mL three-necked flask, intermediates-N-1 (22.8g, 72.3mmol), 1- (4,4,5, 5-tetramethyl-1, 3, 2-d-dioxanaphthalen-2-yl) -9H-carbazole (21.1g, 72.3mmol), and K were charged2CO3(20.1g, 144.6mmol) and THF/H2After O (200mL/100mL), Pd (PPh) was charged at 40 ℃3)4(0.42g, 0.36mmol), and the mixture was stirred at 80 ℃ for 12 hours under a nitrogen atmosphere. The reaction is stopped and the temperature is reduced to room temperature, the reaction solution is washed for three times, organic phases are combined, dried by anhydrous magnesium sulfate, filtered, evaporated and concentrated. Finally, 2',5' -dichloro-9H, 9'H-1,4' -bifonazole (intermediate-Z-1) was isolated using column chromatography (n-hexane: ethyl acetate ═ 3:1(v/v) (23.7g, 81% yield).
intermediate-Z-X of Table 3 was synthesized in the same manner as intermediate-Z-1, except that intermediate-N-X was used instead of intermediate-N-1 and NY-X was used instead of NY-1 to prepare intermediate-Z-X.
TABLE 3
Figure BDA0002990959970000211
Figure BDA0002990959970000212
In a 500mL three-neck flaskintermediate-Z-1 (23.7g, 59.1mmol), Cu powder (0.38g, 5.91mmol) and K2CO3(8.17g, 59.1mmol) and nitro nitrogen (250mL) were mixed. The temperature was raised to 190 ℃ under nitrogen atmosphere, and the reaction was stirred for 12 hours. After the reaction is finished, the temperature is brought to room temperature, the mixture is washed for three times, organic phases are combined, anhydrous magnesium sulfate is used for drying and dewatering, filtering is carried out, and the nitro nitrogen is removed through reduced pressure distillation. Finally, intermediate-a-1 (11.3g, yield: 52%) was isolated using column chromatography (n-heptane: dichloromethane ═ 3:1 (v/v).
The intermediates A-X of Table 4 were synthesized using the same procedure as for the synthesis of intermediate-A-1, except that intermediate-Z-X was used instead of intermediate-Z-1 to give intermediate-A-X.
TABLE 4
Figure BDA0002990959970000213
Figure BDA0002990959970000221
intermediate-A-1 (11.3g, 30.97mmol), bromobenzene (5.84g, 37.17mmol), Cu powder (0.20g, 3.1mmol) and K2CO3(4.28g, 30.97mmol) and nitro nitrogen (200mL) were placed in a 500mL three-necked flask. Stirring at 190 ℃ for 12 hours under the protection of nitrogen. After the reaction was completed, the temperature was lowered to room temperature, the mixture was washed with water three times, and then the organic layer was separated using MgSO4Drying to remove water, filtering, and distilling under reduced pressure to remove nitro nitrogen. Chromatography column separation gave intermediate-B-1 (10.1g, 74%).
intermediate-B-X of Table 5 was synthesized using the same procedure as for intermediate-B-1, except that intermediate-A-X was used instead of intermediate-A-1 and NZ-X was used instead of NZ-1 to prepare intermediate-B-X.
TABLE 5
Figure BDA0002990959970000222
Figure BDA0002990959970000231
Figure BDA0002990959970000232
NM-1(20g, 106mmol), M-1(10.4g, 112mmol), and 200mL of toluene were placed in a 500mL three-necked flask under nitrogen. Heating to 70 deg.C, adding sodium tert-butoxide (15.2g, 158mmol), X-Phos (0.88g, 2.12mmol) and Pd in sequence2(dba)3(0.98g, 1.06mmol), and the reaction was refluxed at elevated temperature for 1 hour. Cooling to room temperature, washing with water for three times, drying with anhydrous magnesium sulfate, filtering, and concentrating. Column chromatography gave intermediate-D-1 (22.6g, 86.9%).
intermediate-D-X of Table 6 was synthesized in the same manner as intermediate-D-1 except that intermediate NM-1 was replaced with NM-X and intermediate-1 was replaced with M-X to prepare intermediate-D-X.
TABLE 6
Figure BDA0002990959970000233
Figure BDA0002990959970000241
Figure BDA0002990959970000242
Into a 250mL three-necked flask were charged intermediate-B-1 (10g, 22.7mmol) and 2-fluorobenzeneboronic acid (33.3g, 23.8mmol), K2CO3(7.9g, 56.8mmol) and THF/H2After O (80mL/40mL), Pd (PPh) was placed at 40 ℃3)4(0.13g, 0.11mmol), and the mixture was stirred at 80 ℃ for 12 hours under a nitrogen atmosphere. The reaction is stopped and the temperature is reduced to room temperature, the reaction solution is washed for three times, organic phases are combined, dried by anhydrous magnesium sulfate, filtered, evaporated and concentrated. Finally, theColumn chromatography (n-hexane: ethyl acetate: 3:1 (v/v)) was used to isolate intermediate-E-1 (9.4g, 82.3% yield).
Consistent with the synthesis method of the intermediate-E-1, only the intermediate-B-X is used for replacing the intermediate-B-1, and YM-X is used for replacing YM-1 to obtain the intermediate-E-X.
TABLE 7
Figure BDA0002990959970000243
Figure BDA0002990959970000251
Figure BDA0002990959970000252
intermediate-B-1 (4.2g, 9.5mmol), intermediate-D-1 (2.4g, 9.5mmol), and 40mL of toluene were placed in a 100mL three-necked flask under nitrogen. The temperature was raised to 70 ℃ and sodium tert-butoxide (1.4g, 14.3mmol), S-Phos (0.09g, 0.19mmol) and Pd were added in this order2(dba)3(0.08g, 0.01mmol), and the reaction was refluxed at elevated temperature for 2 hours. Cooling to room temperature, washing with water for three times, drying with anhydrous magnesium sulfate, filtering, and concentrating. Chromatography on a column and n-heptane recrystallisation gave compound 1(4.3g, 69.5%). The mass spectrum is as follows: 650.3[ M + H ] M/z]+。
Compound X in Table 8 was synthesized in the same manner as Compound 1 except that Compound X was prepared by substituting intermediate-B-X for intermediate-B-1, intermediate-D-X or intermediate-E-X for intermediate-D-1.
TABLE 8
Figure BDA0002990959970000253
Figure BDA0002990959970000261
Figure BDA0002990959970000271
Figure BDA0002990959970000281
Wherein, the nuclear magnetic data of the compound 1 is as follows:
1H-NMR(CDCl3,400MHz):8.22(d,2H),8.00-7.93(d,3H),7.71-7.50(m,15H),7.48-7.23(m,10H),6.86(s,1H)
the nuclear magnetic data for compound 8 is:
1H-NMR(CDCl3,400MHz):8.22(d,2H),8.04-7.95(d,2H),7.77(d,1H),7.68-7.64(m,7H),7.51-7.49(m,10H),7.42-7.33(m,6H),6.95(s,1H),1.72(s,6H).
the nuclear magnetic data for compound 15 is:
1H-NMR(CDCl3,400MHz):8.22(d,2H),8.02(d,1H),7.82(d,1H),7.70-7.60(m,3H),7.58-7.10(m,19H),6.89(s,1H).
preparation examples of devices
Example 1:
the anode was prepared by the following procedure: will have a thickness of
Figure BDA0002990959970000282
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2：N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002990959970000283
And a Hole Injection Layer (HIL) of (a) and vapor-plating on the hole injection layerNPB formed to a thickness of
Figure BDA0002990959970000284
The hole transport layer of (1).
Compound 1 was vacuum-deposited on the hole transport layer to a thickness of
Figure BDA0002990959970000285
The hole adjusting layer of (1).
On the hole-adjusting layer, a CBP, Ir (piq)2(acac) Co-deposition was carried out at a film thickness ratio of 100:3 to a thickness of
Figure BDA0002990959970000286
The red light emitting layer (R-EML).
ET-06 and LiQ were formed by vapor deposition at a film thickness ratio of 1:1
Figure BDA0002990959970000287
A thick Electron Transport Layer (ETL) formed by depositing Yb on the electron transport layer
Figure BDA0002990959970000288
Then magnesium (Mg) and silver (Ag) were vacuum-evaporated on the Electron Injection Layer (EIL) at a film thickness ratio of 1:9 to form an EIL having a thickness of
Figure BDA0002990959970000289
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA00029909599700002810
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Examples 2 to 22
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the hole-adjusting layer, compounds in table 9 below were used instead of compound 1.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a was used instead of compound 1 in forming the hole-adjusting layer.
Comparative example 2
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound B was used instead of compound 1 in forming the hole-adjusting layer.
Comparative example 3
An organic electroluminescent device was produced in the same manner as in example 1, except that compound C was used instead of compound 1 in forming the hole-adjusting layer.
The structures of the compounds used in the above examples and comparative examples are as follows:
Figure BDA0002990959970000291
for the organic electroluminescent device prepared as above, at 20mA/cm2The device performance was analyzed under the conditions shown in table 9 below:
TABLE 9
Figure BDA0002990959970000301
From the results in Table 9, it is understood that in examples 1 to 22 in which the compounds were used as the hole-adjusting layer, the voltage of the organic electroluminescent device prepared by using the compounds used in the present application as the hole-adjusting layer was reduced by at least 5.9%, the current efficiency (Cd/A) was improved by at least 18.2%, and the lifetime was improved by at least 10.5%, as compared with comparative examples 1 to 3 in which known compounds were used.
The preferred embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications can be made to the technical solution of the present application within the technical idea of the present application, and these simple modifications are all within the protection scope of the present application.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.

Claims (10)

1. An organic compound having a structure represented by chemical formula 1:
Figure FDA0003598312710000011
wherein R is1Selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
Figure FDA0003598312710000012
wherein the content of the first and second substances,
Figure FDA0003598312710000013
represents a chemical bond, when the group W is substituted with one or more substituents, each independently selected from: deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl;
R2、R3、R4and R5Are identical or different from one another and are each independently selected from the group A or
Figure FDA0003598312710000014
And R is2、R3、R4And R5Is selected from
Figure FDA0003598312710000015
Wherein the content of the first and second substances,
Figure FDA0003598312710000016
represents a chemical bond;
the group A is selected from deuterium, a halogen group, a cyano group, an alkyl group with 1-5 carbon atoms and an aryl group with 6-12 carbon atoms;
n2～n5with ntIs represented by R2～R5With RtIs represented by t is a variable and is an arbitrary integer of 2 to 5, ntRepresents a substituent RtThe number of (2); when t is 2, 3 or 5, ntSelected from 0, 1,2, 3; when t is 4, ntSelected from 0, 1,2, 3, 4; when n istWhen greater than 1, any two RtThe same or different;
l and L1The same or different, and each is 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 and L1The substituents in (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl;
Ar1and Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms;
Ar1and Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, optionally, in Ar1And Ar2Any two adjacent substituents form a fluorene ring.
2. An organic compound according to claim 1, characterized in that the group a is selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
3. The organic compound of claim 1, wherein Ar is Ar1And Ar2The same or different from each other, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
4. The organic compound of claim 1, wherein Ar is Ar1And Ar2Identical to or different from each other and each independently selected from the group V, which is unsubstituted or substituted, selected from the group consisting of:
Figure FDA0003598312710000021
wherein the content of the first and second substances,
Figure FDA0003598312710000022
represents a chemical bond; when the group V is substituted with one or more substituents, each of the substituents is independently selected from: deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.
5. An organic compound, wherein the organic compound is selected from the group consisting of:
Figure FDA0003598312710000023
Figure FDA0003598312710000031
Figure FDA0003598312710000041
Figure FDA0003598312710000051
Figure FDA0003598312710000061
Figure FDA0003598312710000071
Figure FDA0003598312710000081
Figure FDA0003598312710000091
Figure FDA0003598312710000101
Figure FDA0003598312710000111
6. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode;
the functional layer comprises an organic compound according to any one of claims 1 to 5.
7. The electronic component according to claim 6, wherein the functional layer comprises a hole-adjusting layer containing the organic compound.
8. The electronic component according to claim 6, wherein the functional layer comprises a hole transport layer containing the organic compound.
9. An electronic device comprising the electronic component according to any one of claims 6 to 8.
10. The electronic device according to claim 9, wherein the electronic element is an organic electroluminescent device or a photoelectric conversion device.
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