CN113493455B - Organic compound, electronic component, and electronic device - Google Patents

Organic compound, electronic component, and electronic device Download PDF

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CN113493455B
CN113493455B CN202110757597.4A CN202110757597A CN113493455B CN 113493455 B CN113493455 B CN 113493455B CN 202110757597 A CN202110757597 A CN 202110757597A CN 113493455 B CN113493455 B CN 113493455B
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岳娜
李应文
李昕轩
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Material Science Co Ltd
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Abstract

The invention belongs to the technical field of organic materials, and provides an organic compound, an electronic element and an electronic device, wherein the organic compound has a structure shown in a formula 1: wherein L is selected from single bond, substituted or unsubstituted arylene group with 6-25 carbon atoms, and substituted or unsubstituted heteroarylene group with 5-25 carbon atoms; ar (Ar) 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. The organic compound of the present invention can improve the performance of electronic components.
Figure DDA0003147728640000011

Description

Organic compound, electronic component, and electronic device
Technical Field
The present application relates to the technical field of organic materials, and in particular, to an organic compound, an electronic component, and an electronic device.
Background
With the development of electronic technology and the advancement of material science, the range of applications of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components, such as organic electroluminescent devices or photoelectric conversion devices, generally comprise a cathode and an anode, which are arranged opposite each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
For example, when the electronic component is an organic electroluminescent device, it generally includes an anode, a hole transport layer, an organic light emitting layer as an energy conversion layer, an electron transport layer, and a cathode, which are sequentially stacked. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the organic light-emitting layer under the action of the electric field, holes at the anode side also move to the organic light-emitting layer, the electrons and the holes are combined in the organic light-emitting layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the organic light-emitting layer emits light outwards.
CN108084195a discloses a biscarbazole fused ring compound used in an organic light emitting device, which has characteristics of low driving voltage and high luminous efficiency when applied to an organic light emitting layer according to the publication, but is not suitable for a hole transporting material.
Disclosure of Invention
The invention provides an organic compound, an electronic component and an electronic device, wherein the organic compound can improve the performance of the electronic component.
In order to achieve the purpose of the invention, the application adopts the following technical scheme:
a first aspect of the present invention provides an organic compound having a structure represented by formula 1:
Figure GDA0004006485130000011
L、L 1 、L 2 the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;
L、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, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-15 carbon atoms and heteroaryl with 5-15 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring.
Another aspect of the present invention is to provide an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises an organic compound according to any one of the above.
A further aspect of the present invention provides an electronic device comprising the electronic element described above.
The organic compound provided by the invention is used for condensing carbazole compounds, so that the carbazole compounds have a larger conjugated system and a stronger intramolecular electron transfer capability in molecules, have higher thermal stability, and reduce the easy formation of agglomeration of conventional carbazole compounds in a solid phase. In addition, the benzene ring is condensed on the same benzene ring of the carbazole group and is combined with N atom of carbazole to be condensed to form an azabenzene part, the formed three six-membered rings are condensed with each other, the rigidity of the structure is increased, the thermal stability of the derivative is improved, molecular aggregation is reduced, and the triarylamine group is connected with the condensed ring structure, so that the charge of a dispersed material is facilitated, the coplanarity of molecules is reduced, the formed organic compound is easier to form a film, the glass transition temperature of a product is improved, the product is not easy to crystallize, the conductivity of the material is effectively enhanced, and the generation and the transmission of holes are facilitated. The organic compound is used in an organic electroluminescent device, so that the service life and the luminous efficiency of the organic electroluminescent device are obviously improved, and the working voltage is reduced to a certain extent.
Drawings
The above and other features and advantages of the present application will become more apparent by describing in detail exemplary embodiments thereof with reference to the attached drawings.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of an electronic device according to another embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. and a second electronic device.
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.
In a first aspect, the present application provides an organic compound having a structure represented by formula 1:
Figure GDA0004006485130000021
/>
L、L 1 、L 2 the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 25 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl groups having 5 to 30 carbon atoms;
L、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, halogen group, cyano, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, trialkylsilyl with 3-12 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-15 carbon atoms and heteroaryl with 5-15 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated ring.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event may or may not occur, and that the description includes instances where such event may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring.
In the present application, the term "substituted or unsubstituted" means that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc), and if there is a substituent, the number of substituents may be one or plural. For example, "substituted or unsubstituted aryl" refers to an aryl or unsubstituted aryl having one or more substituents Rc. Wherein the above substituent, i.e., rc, may be, for example, deuterium, halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl, etc. When two substituents Rc are attached to the same atom, the two substituents Rc may be present independently or attached to each other to form a ring with the atom; when two adjacent substituents Rc are present on a functional group, the adjacent two substituents Rc may be present independently or fused to the functional group to which they are attached to form a ring.
In this application, the descriptions used herein of the manner in which each … … is independently selected from the group consisting of "and" … … is independently selected from the group consisting of "and" … … is independently selected from the group consisting of "are interchangeable, and are to be understood in a broad sense, which may 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, "
Figure GDA0004006485130000031
Wherein each q is independently selected from 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; formula Q-2 represents that each benzene ring of biphenyl has Q substituents R'.The number q of R ' substituents 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 mutually influenced.
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 or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein. Wherein, the aryl does not contain hetero atoms such as B, N, O, S, P, si and the like. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,
Figure GDA0004006485130000032
A base, etc.
In the present application, a substituted aryl group may be one in which one or more hydrogen atoms in the aryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, and the like. Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like. Specific examples of heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophenyl substituted phenyl, pyridine substituted phenyl, and 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 substituents being 18.
In the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof containing at least one heteroatom in the ring, which may be at least one of B, O, N, P, si and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include, but are not limited to, 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, phenanthroline, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl is heteroaryl groups of a polycyclic ring system type which are connected in a conjugated manner through carbon-carbon bonds.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, 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, non-positional connection means a single bond extending from a ring system
Figure GDA0004006485130000041
Which means that one end of the bond can be attached to any position in the ring system through which the bond extends, the other end being attached to a compound moleculeThe rest.
For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
Figure GDA0004006485130000042
As another example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
Figure GDA0004006485130000043
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
Figure GDA0004006485130000044
Figure GDA0004006485130000051
In the present application, cycloalkyl groups having 3 to 10 carbon atoms may be used as substituents for aryl groups, heteroaryl groups, and specific examples thereof include, but are not limited to, cyclopentyl groups, cyclohexyl groups, adamantyl groups, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight chain alkyl group having 1 to 10 carbon atoms and a branched chain alkyl group having 3 to 10 carbon atoms, and specific examples of the alkyl group having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like, and the number of carbon atoms may be 1,2, 3,4, 5, 6, 7, 8, 9, and 10, for example.
In this application, halogen may include fluorine, chlorine, bromine, iodine.
In the present application, the aryl group having 6 to 15 carbon atoms as a substituent may have 6 (for example, phenyl), 10 (for example, naphthalene), 12 (for example, biphenyl), 13 (for example, fluorenyl), 15, and the like.
In the present application, the heteroaryl group having 5 to 15 carbon atoms as a substituent may have 5 (for example, pyridyl group), 12 (for example, dibenzothienyl group or dibenzofuranyl group), and the like.
In the present application, the structure of formula 1 is understood to be an arylamine group
Figure GDA0004006485130000052
The linkage L of (B) may be in a form which is complementary to the structure in brackets->
Figure GDA0004006485130000053
Ligation is by any of the 11 sites shown.
In some embodiments, the organic compound has a structure selected from the group consisting of:
Figure GDA0004006485130000054
Figure GDA0004006485130000061
optionally L, L 1 、L 2 Identical or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 20 carbon atomsA base. Specifically L, L 1 、L 2 And each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Optionally L, L 1 、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, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazole group.
In one embodiment, L is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene. L (L) 1 、L 2 And are the same or different 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.
Optionally L, L 1 And L 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms.
Optionally L, L 1 、L 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridinyl.
In a preferred embodiment, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 18 carbon atoms, which further increases the lifetime and external quantum efficiency of the device.
In one embodiment, L is selected from the group consisting of a single bond and:
Figure GDA0004006485130000062
optionally, L is selected from the group consisting of a single bond and:
Figure GDA0004006485130000063
Figure GDA0004006485130000071
preferably, L is selected from the group consisting of:
Figure GDA0004006485130000072
in one embodiment, L 1 And L 2 Each independently selected from the group consisting of a single bond and:
Figure GDA0004006485130000073
alternatively, L 1 、L 2 Each independently selected from the group consisting of a single bond and:
Figure GDA0004006485130000074
in one embodiment, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted dibenzofuranA group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group.
Alternatively, ar 1 And Ar is a group 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, fluoroalkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms; optionally, any two adjacent substituents form a 5-13 membered saturated or unsaturated ring.
Alternatively, ar 1 And Ar is a group 2 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl; optionally, any two adjacent substituents form a fluorene ring, cyclohexane or cyclopentane.
Alternatively, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted groups Z selected from the group consisting of:
Figure GDA0004006485130000081
the substituted group Z has one or more than two substituents, and the substituents are independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, cyclohexyl and cyclopentyl; when the number of substituents is greater than 1, the substituents may be the same or different, optionally any two adjacent substituents form a fluorene ring, cyclopentane, cyclohexane.
Alternatively, ar 1 、Ar 2 Each independently selected from the group consisting of:
Figure GDA0004006485130000082
optionally, a，Ar 1 、Ar 2 Each independently selected from the group consisting of:
Figure GDA0004006485130000083
/>
Figure GDA0004006485130000091
optionally, the organic compound is selected from the group consisting of:
Figure GDA0004006485130000092
/>
Figure GDA0004006485130000101
/>
Figure GDA0004006485130000111
/>
Figure GDA0004006485130000121
/>
Figure GDA0004006485130000131
/>
Figure GDA0004006485130000141
/>
Figure GDA0004006485130000151
/>
Figure GDA0004006485130000161
/>
Figure GDA0004006485130000171
/>
Figure GDA0004006485130000181
the method for synthesizing the organic compound provided herein is not particularly limited, and a person skilled in the art can determine a suitable synthesis method according to the preparation method of the organic compound binding synthesis example of the present application. In other words, the synthesis examples section of the present application illustratively provides a process for the preparation of organic compounds, the starting materials employed being commercially available or obtainable by methods well known in the art. All of the organic compounds provided herein can be obtained by one skilled in the art according to the preparation methods of these exemplary synthesis examples, 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.
In a second aspect, the present application provides an electronic component comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
Optionally, the functional layer includes a hole transport layer comprising an organic compound provided herein. The hole transport layer may be composed of an organic compound provided herein, or may be composed of an organic compound provided herein and other materials. The hole transport layer may be one layer, or may be two or more layers.
According to one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
The organic compound can be applied to the hole transport layer 321 of the organic electroluminescent device to prolong the service life of the organic electroluminescent device, and has higher luminous efficiency and lower working voltage.
In this application, anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
Optionally, an electron blocking layer 322 is disposed between the hole transporting layer 321 and the organic light emitting layer 330, where the electron blocking layer 322 can effectively block the electron carrier from being transported to the anode 100, so as to protect the hole transporting layer 321 material, and the electron blocking layer material may be TCTA.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. In a specific embodiment, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
Alternatively, 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 are not particularly limited in this application. For example, the host material may be CBP, α, β -ADN. Organic compoundThe guest material of the 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, and is not particularly limited herein, and for example, the guest material may be Ir (MDQ) 2 (acac)、Ir(dmpq) 3 、BD-1。
Alternatively, the electron transport layer 340 may be a single layer structure or a multi-layer structure, which 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 TPBi and LiQ.
In this application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. A metal electrode containing magnesium and silver is preferably included as a cathode.
Optionally, 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. 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. For example, the material of hole injection layer 310 may be selected from m-MTDATA, HAT-CN, 1T-NATA, or 2T-NATA.
Optionally, 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. The electron injection layer 350 may include an inorganic material such as alkali metal sulfide, alkali metal halide, yb, etc., or may include a complex of alkali metal and organic matter. For example, the electron injection layer 350 may include LiQ or Yb.
Alternatively, as shown in fig. 1, the hole injection layer 310, the hole transport layer 321, the electron blocking layer 322, the organic light emitting layer 330, the electron transport layer 340, and the electron injection layer 350 constitute the functional layer 300.
According to another embodiment, the electronic component is 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 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises an organic compound provided herein.
Alternatively, the functional layer 300 includes a hole transport layer 321, and the hole transport layer 321 includes an organic compound of the present application. The hole transport layer 321 may be formed of an organic compound provided herein, or may be formed of an organic compound provided herein and other materials.
Alternatively, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 321, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Alternatively, the photoelectric conversion device may be a solar cell, in particular, 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 photoelectric conversion layer, an electron transport layer, and a cathode, which are sequentially stacked, wherein the hole transport layer includes an organic compound of the present application.
In a third aspect, the present application also provides an electronic device comprising an electronic element according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, including the organic electroluminescent device described above. 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, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting device, an optical module, etc.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, including the above-mentioned photoelectric conversion device. The second electronic device 500 may be a solar power generation device, a light detector, a fingerprint identification device, a light module, a CCD camera, or other type of electronic device.
The present application is further illustrated below with reference to examples.
1. Synthesis of intermediate IM-1-X
1. Synthesis of intermediate IM-1-1
Figure GDA0004006485130000201
At N 2 Under an atmosphere, starting material SA-1-1 (127 g,549.57 mmol), 25wt% sulfuric acid (127 mL) and hydrazoic acid (23.65 g,549.57 mmol) were added and stirred at 50℃for 3 hours. After the completion of the reaction, 60mL of a 20wt% aqueous potassium carbonate solution was added for neutralization, and anhydrous MgSO was used after washing 4 The organic layer was dried, and the solvent was collected and purified by passing through a column to give intermediate IM-1-1-a (21.6 g, yield 15.9%) and intermediate IM-1-1-b (17.6 g, yield 13.1%) respectively.
2. Referring to a method for synthesizing the intermediate IM-1-1, the intermediate IM-1-X shown in Table 1 below was synthesized, wherein the raw material SA-1-X was used in place of SA-1-1, and the intermediate IM-1-X shown in Table 1 below was synthesized.
TABLE 1
Figure GDA0004006485130000202
2. Synthesis of intermediate IM-2-Y
1. Synthesis of intermediate IM-2-1
Figure GDA0004006485130000211
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, intermediate IM-1-1-a (17.5 g,71.11 mmol) was added, and after completion of the reaction, SA-2-1 (16.9 g,71.11 mmol), tris (dibenzylideneacetone) dipalladium (0.65 g), X-phos (0.68 g), sodium t-butoxide (10.2 g) and toluene (144 mL) were heated to 105-110℃and stirred for 2h and cooled to room temperature. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and recrystallization purification of the crude product using methylene chloride/n-heptane system afforded intermediate IM-2-1 (18.0 g, 71.0% yield).
2. Referring to the method for synthesizing intermediate IM-2-1, intermediate IM-2-Y shown in Table 2 below was synthesized, wherein intermediate IM-1-X (wherein IM-1-5 was purchased directly) was substituted for intermediate IM-1-1-a, and reactant SA-2-Z was substituted for reactant SA-2-1, and intermediate IM-2-Y shown in Table 2 below was synthesized.
TABLE 2
Figure GDA0004006485130000212
3. Synthesis of intermediate IM-3-Y
1. Synthesis of intermediate IM-3-1
Figure GDA0004006485130000213
A three-necked flask equipped with a mechanical stirrer, a thermometer and a bulb condenser was purged with nitrogen (0.100L/min) for 15 minutes, and then intermediate IM-2-1 (17.8 g,49.91 mmol), palladium acetate (5.61 g), tricyclohexylfluoroborate (18.38 g), cesium carbonate (65.05 g) and N, N-dimethylacetamide (178 mL) were added. Stirring is started, reflux reaction is carried out for 2h under heating, and after the reaction is finished, the mixture is cooled to room temperature. Extracting the reaction liquid with chloroform, separating an organic phase, drying the organic phase by using anhydrous magnesium sulfate, filtering, and then decompressing and distilling filtrate to remove a solvent to obtain a crude product; the crude product was purified by silica gel column chromatography to give intermediate IM-3-1 (8.47 g, yield 53.0%).
2. Referring to a method for synthesizing the intermediate IM-3-1, the intermediate IM-3-X shown in Table 3 below was synthesized, wherein intermediate IM-2-X was used in place of intermediate IM-2-1, and intermediate IM-3-X shown in Table 3 below was synthesized.
TABLE 3 Table 3
Figure GDA0004006485130000221
4. Synthesis of intermediate IM-4-X
1. Synthesis of intermediate IM-4-1
Figure GDA0004006485130000222
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was purged with nitrogen (0.100L/min) for 15min, then intermediate IM-3-1 (17.8 g,55.59 mmol), pinacol biborate (14.12 g,55.59 mmol), potassium acetate (8.18 g), x-Phos (0.53 g), tris (dibenzylideneacetone) dipalladium (0.51 g) and 1, 4-dioxane (144 mL) were sequentially added, and the mixture was heated to 75-85℃to reflux for 3h, followed by cooling to room temperature after the completion of the reaction. The reaction solution was extracted, the organic phase was dried over anhydrous magnesium sulfate, the solvent was removed from the filtrate under reduced pressure after filtration, and the crude product was recrystallized and purified using a toluene system and filtered to give intermediate IM-4-1 (14.54 g, 71.2%).
2. Referring to the synthesis method of the intermediate IM-4-1, the intermediate IM-4-X shown in Table 4 below was synthesized, wherein intermediate IM-3-X was used in place of intermediate IM-3-1, and the intermediate IM-4-X shown in Table 4 below was synthesized.
TABLE 4 Table 4
Figure GDA0004006485130000231
5. Synthesis of intermediate IM-5-Z
1. Synthesis of intermediate IM-5-1
Figure GDA0004006485130000232
A three-necked flask equipped with a mechanical stirrer, thermometer and bulb condenser was purged with nitrogen (0.100L/min) for 15min, intermediate IM-4-1 (14.30 g,38.94 mmol), reactant SA-4-1 (7.45 g,38.94 mmol), palladium acetate (0.087 g), potassium carbonate (8.06 g), s-phos (0.32 g), toluene (84 mL), absolute ethanol (28 mL) and deionized water (28 mL) were added; stirring and heating are started, the temperature is increased to 70-80 ℃, the reflux reaction is carried out for 4 hours, and the reaction is cooled to room temperature after the reaction is finished. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and recrystallization purification of the crude product using methylene chloride/n-heptane system afforded solid intermediate IM-5-1 (9.45 g, 69.0%).
2. Referring to the synthesis method of IM-5-1, IM-5-Z shown in Table 5 below was synthesized, in which intermediate IM-4-X was used in place of IM-4-1 and reactant SA-4-Y was used in place of reactant SA-4-1, and IM-5-Z shown in Table 5 below was synthesized.
TABLE 5
Figure GDA0004006485130000233
Figure GDA0004006485130000241
6. Synthesis of intermediate IM-6-X
1. Synthesis of intermediate IM-6-1
Figure GDA0004006485130000242
To a three-necked flask equipped with a mechanical stirrer, thermometer and bulb condenser was introduced nitrogen (0.100L/min) to replace for 15min, and reactant SA-5-1 (7.5 g,28.5 mmol), reactant SA-6-1 (4.46 g,28.5 mmol), tetrakis (triphenylphosphine) palladium (0.33 g), potassium carbonate (5.90 g), TBAB (0.18 g), toluene (48 mL), absolute ethanol (16 mL) and deionized water (16 mL) were added; stirring and heating are started, the temperature is increased to 70-80 ℃, the reflux reaction is carried out for 4 hours, and the reaction is cooled to room temperature after the reaction is finished. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and recrystallization purification of the crude product using methylene chloride/n-heptane system afforded solid intermediate IM-6-1 (5.13 g, 61.0% yield).
2. Referring to the method for synthesizing intermediate IM-6-1, intermediate IM-6-X shown in Table 6 below was synthesized, wherein reactant SA-5-Y was substituted for reactant SA-5-1, reactant SA-6-Z was substituted for reactant SA-6-1, and intermediate IM-6-X shown in Table 6 below was synthesized.
TABLE 6
Figure GDA0004006485130000251
7. Synthesis of intermediate IM-7-Y
1. Synthesis of intermediate IM-7-1
Figure GDA0004006485130000252
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, intermediate IM-3-1 (9.3 g,29.05 mmol), reaction product SA-7-1 (4.92 g,29.05 mmol), tris (dibenzylideneacetone) dipalladium (0.27 g), X-phos (0.28 g), sodium t-butoxide (4.19 g) and toluene (93 mL) were added, and the mixture was heated to 105-110℃for 1h with stirring, and after the completion of the reaction, the mixture was cooled to room temperature. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and recrystallization purification of the crude product using methylene chloride/n-heptane system afforded solid intermediate IM-7-1 (8.42 g, 70.9% yield).
2. Referring to the synthesis method of the intermediate IM-7-1, the intermediate IM-7-Z shown in Table 7 below was synthesized, wherein intermediate IM-3-X or IM-5-Z was used in place of intermediate IM-3-1, and reactant SA-7-W was used in place of reactant SA-7-1, and intermediate IM-7-X shown in Table 7 below was synthesized.
TABLE 7
Figure GDA0004006485130000253
Figure GDA0004006485130000261
/>
Figure GDA0004006485130000271
Synthesis example 1
Figure GDA0004006485130000272
A three-necked flask equipped with a mechanical stirrer, a thermometer and a spherical condenser was charged with nitrogen (0.100L/min) for 15min for replacement, intermediate IM-7-1 (7.5 g,18.36 mmol), reaction product SA-8-1 (4.28 g,18.36 mmol), tris (dibenzylideneacetone) dipalladium (0.17 g), s-phos (0.22 g), sodium t-butoxide (2.65 g) and toluene (64 mL) were added, and the mixture was heated to 105-110℃for 2h with stirring, and after the completion of the reaction, the mixture was cooled to room temperature. Extraction, water washing, combining the organic phases, drying over anhydrous magnesium sulfate, filtering to remove the solvent, and recrystallization purification of the crude product using methylene chloride/n-heptane system gave solid compound 21 (6.90 g, 67.0% yield), mass spectrum: m/z=561.23 [ m+h] + 。
Compound X was synthesized by the synthesis method of reference compound 21, wherein intermediate IM-7-Z was used in place of IM-7-1, reactant SA-8-Y (or IM-6-X) was used in place of reactant SA-8-1, and the main raw materials, synthesized compounds, and the yields and mass spectrum characterization results thereof were shown in table 8.
TABLE 8
Figure GDA0004006485130000273
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Figure GDA0004006485130000281
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Figure GDA0004006485130000291
Figure GDA0004006485130000301
/>
Organic electroluminescent device fabrication and evaluation
Example 1
An organic electroluminescent device was prepared by the following procedure: cutting a substrate plated with ITO/Ag/ITO (5 nm/100nm/5 nm) electrode into a size of 40mm×40mm×0.7mm, preparing an experimental substrate having a cathode, an anode and an insulating layer pattern by photolithography, and using ultraviolet ozone and O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum evaporating compound HAT-CN on experimental substrate (anode) to form a film with thickness of
Figure GDA0004006485130000302
A Hole Injection Layer (HIL); then vacuum evaporating compound 21 on the hole injection layer to form a layer with a thickness +.>
Figure GDA0004006485130000303
A Hole Transport Layer (HTL).
Evaporating compound TCTA as Electron Blocking Layer (EBL) on Hole Transport Layer (HTL) with thickness of
Figure GDA0004006485130000304
Vapor plating BD-1 containing compound alpha, beta-ADN as main body on Electron Blocking Layer (EBL) and doping 2% by weight to form a film with a thickness of
Figure GDA0004006485130000305
An organic light emitting layer (EML).
On the organic light emitting layer (EML), TPBi and LiQ are mixed in a weight ratio of 1:1 and evaporated to form an Electron Transport Layer (ETL) with a thickness of
Figure GDA0004006485130000306
In electron transferVapor deposition on transport layer (ETL)
Figure GDA0004006485130000307
As an Electron Injection Layer (EIL), then magnesium (Mg) and silver (Ag) were mixed at 1:9, vacuum evaporating on the electron injection layer as cathode with thickness of +.>
Figure GDA0004006485130000308
Evaporating compound CP-1 as organic coating layer (CPL) on cathode with thickness of
Figure GDA0004006485130000309
The evaporated device was encapsulated with an ultraviolet hardening resin in a nitrogen glove box.
Examples 2 to 21
In the above device structure, an organic electroluminescent device was manufactured in the same manner as in example 1, except that the compound 21 described in table 10 was replaced with the compound for the Hole Transport Layer (HTL).
Comparative examples 1 to 4
In comparative examples 1 to 4, organic electroluminescent devices were manufactured in the same manner as in example 1, except that the compound a, the compound B, the compound C, and the compound D were used as the material of the Hole Transport Layer (HTL) instead of the compound 21, respectively.
The structural formulas of HAT-CN, alpha, beta-AND, TCTA, liQ, TPBi, CP-1, BD-1, compound A, compound B, compound C and compound D are shown in table 9.
TABLE 9
Figure GDA00040064851300003010
/>
Figure GDA0004006485130000311
The properties of the organic electroluminescent device thus prepared are shown in Table 10, whichThe voltage, efficiency and color coordinates are at a constant current density of 10mA/cm 2 Test under constant current density of 20mA/cm for T95 device lifetime 2 The test is performed below.
Table 10
Figure GDA0004006485130000312
Figure GDA0004006485130000321
/>
Referring to the results of table 10, it was found that the organic electroluminescent devices obtained in examples 1 to 21 generally have long life and high luminous efficiency when the color coordinates CIEy were in the vicinity of 0.051, as compared with the organic electroluminescent devices in comparative examples 1 to 4. Wherein, the external quantum efficiency of the organic electroluminescent device of example 1-example 21 is improved by more than 7% compared with the external quantum efficiency of the comparative example; the life of the organic electroluminescent device T95 is prolonged by at least 14% compared with the comparative example. At the same time, the driving voltage is reduced by more than 0.2V. In short, the organic compound is applied to a Hole Transport Layer (HTL) of an organic electroluminescent device, so that the service life and external quantum efficiency of the organic electroluminescent device are obviously improved, and the working voltage is reduced to a certain extent.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.

Claims (11)

1. An organic compound having a structure represented by formula 1:
Figure FDA0004189512160000011
L、L 1 、L 2 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 pyridylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazole group;
L、L 1 、L 2 each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridinyl;
Ar 1 and Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted phenanthryl;
Ar 1 and Ar is a group 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, trimethylsilyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl.
2. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
Figure FDA0004189512160000012
/>
3. the organic compound according to claim 1, wherein L is selected from the group consisting of a single bond and:
Figure FDA0004189512160000021
4. the organic compound according to claim 1, wherein L 1 And L 2 Each independently selected from the group consisting of a single bond and:
Figure FDA0004189512160000022
5. the organic compound according to claim 1, wherein Ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted groups Z selected from the group consisting of:
Figure FDA0004189512160000023
the substituted group Z has one or more than two substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, cyclohexyl and cyclopentyl; when the number of substituents is greater than 1, the substituents may be the same or different.
6. The organic compound according to claim 1, wherein Ar 1 、Ar 2 Each independently selected from the group consisting of:
Figure FDA0004189512160000024
/>
Figure FDA0004189512160000031
7. the organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
Figure FDA0004189512160000032
/>
Figure FDA0004189512160000041
/>
Figure FDA0004189512160000051
/>
Figure FDA0004189512160000061
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Figure FDA0004189512160000081
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Figure FDA0004189512160000091
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Figure FDA0004189512160000101
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Figure FDA0004189512160000111
8. an electronic component, characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer contains the organic compound according to any one of claims 1 to 7.
9. The electronic component according to claim 8, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
10. The electronic component according to claim 8, wherein the functional layer includes a hole transport layer, the hole transport layer containing the organic compound.
11. An electronic device comprising the electronic component of any one of claims 8-10.
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