Organic compounds, electronic components and electronic devices containing the same

Abstract

This application belongs to the technical field of organic materials, and provides an organic compound, an electronic component and an electronic device containing the same. The structure of the organic compound is shown in Chemical Formula 1. The organic compound of this application is used in an organic electroluminescent device and can effectively improve the performance of the device.

Description

Technical Field

[0001] 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 including the same. Background Art

[0002] An organic electroluminescent device, also known as an organic light-emitting diode, refers to the phenomenon that an organic light-emitting material emits light under the action of an electric field and is excited by an electric current. It is a process of converting electrical energy into light energy. Compared with inorganic light-emitting materials, an organic electroluminescent diode (OLED) has the advantages of active light emission, a large optical path range, a low driving voltage, high brightness, high efficiency, low energy consumption, and a simple manufacturing process. Due to these advantages, organic light-emitting materials and devices have become one of the very popular research topics in the scientific community and the industrial community.

[0003] An organic electroluminescent device generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer, and a cathode that are sequentially stacked. When a voltage is applied between the anode and the cathode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light externally.

[0004] In the prior art, CN110662750A, WO2020152043A1, etc. disclose luminescent layer materials that can be prepared in organic electroluminescent devices. However, it is still necessary to continue researching and developing new materials to further improve the performance of electronic components.

[0005] The above information in the background art part of the application is only used to enhance the understanding of the background of the present application. Therefore, it may include information that does not constitute the prior art known to those of ordinary skill in the art. Summary of the Invention

[0006] The purpose of the present application is to provide an organic compound, an electronic component, and an electronic device including the same. The organic compound is used in an organic electroluminescent device and can improve the performance of the device.

[0007] To achieve the above invention purpose, the present application adopts the following technical solutions:

[0008] The first aspect of the present application provides an organic compound, whose structure is shown in Chemical Formula 1:

[0009]

[0010] Among them, A1, A2, A3, and A4 are the same or different, and each independently selected from a benzene ring, a pyridine ring, a fused aromatic ring having 10 to 18 ring carbon atoms, or a fused heteroaromatic ring having 7 to 12 ring carbon atoms;

[0011] R1, R2, R3, R4, R5, and R6 are the same or different, and each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an arylamino group having 12 to 24 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 15 carbon atoms;

[0012] The substituents in R1, R2, R3, R4, R5, and R6 are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms;

[0013] n1 to n6 are represented by n t R1 to R6 are represented by R t t is a variable representing any integer from 1 to 6, n t represents the number of substituents R t When t is 1, 2, 3, or 4, n t is selected from 1, 2, 3, 4, 5, 6, 7; when t is 5, n t is selected from 1, 2, 3, 4; when t is 6, n t is selected from 1, 2, 3, 4, 5; when n t is greater than 1, any two R t are the same or different;

[0014] L is selected from a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms;

[0015] The substituents in L are selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms, a phenyl group;

[0016] X is selected from a single bond, C(R7R8), Si(R9R 10 ), O, S, N(R 11 );

[0017] R7, R8, R9, R 10 and R 11 are the same or different, and each independently selected from an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms.

[0018] The organic compound of the present application has a planar structure formed by the condensation of nitrogen and boron as linking groups. The alternating conjugation and strong rigidity of this planar structure can cause a high excited-state oscillator strength. In addition, the nitrogen in this planar structure is connected to the meta-position of the same benzene as the fluorene or xanthene group, which can adjust the intermolecular force and reduce the concentration quenching effect on the basis of maintaining the original molecular conjugation and oscillator strength of this structure, effectively improving the current efficiency of the device. At the same time, due to the large spatial volume and excellent chemical stability of the fluorene-based or xanthene-based group, it can effectively protect the relatively highly active light-emitting center (i.e., this planar structure), making the molecule have good thermal stability and improving the lifetime of the device. Therefore, using the organic compound of the present application as the blue light-emitting guest material in the light-emitting layer of an organic electroluminescent device can effectively improve the efficiency and lifetime of the device.

[0019] The second aspect of the present application provides an electronic component, including an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound described in the first aspect.

[0020] The third aspect of the present application provides an electronic device, including the electronic component described in the second aspect of the present application.

[0021] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Description of the Drawings

[0022] The drawings are used to provide a further understanding of the present application and constitute a part of the specification. Together with the following specific implementation, they are used to explain the present application, but do not constitute a limitation to the present application.

[0023] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0024] Figure 2 It is a schematic structural diagram of a first electronic device according to an embodiment of the present application.

[0025] Figure 3 It is a schematic structural diagram of a second electronic device according to an embodiment of the present application.

[0026] Description of the Reference Numerals

[0027] 100, Anode; 200, Cathode; 300, Functional Layer; 310, Hole Injection Layer

[0028] 321, Hole Transport Layer; 322, Electron Blocking Layer; 330, Organic Light-Emitting Layer; 341, Hole Blocking Layer

[0029] 340, Electron transport layer 350, Electron injection layer 400, First electronic device 500, Second electronic device Detailed implementation manners

[0030] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more complete and comprehensive, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The features, structures, or characteristics described 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 the embodiments of this application.

[0031] In the figures, for clarity, the thickness of regions and layers may be exaggerated. The same reference numerals in the figures denote the same or similar structures, and thus their detailed descriptions will be omitted.

[0032] The features, structures, or characteristics described 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 the embodiments of this application.

[0033] In a first aspect of the present application, an organic compound is provided, and its structure is shown in Chemical Formula 1:

[0034]

[0035] Wherein, A1, A2, A3, and A4 are the same or different, and each independently selected from a benzene ring, a pyridine ring, a fused aromatic ring having 10 to 18 ring carbon atoms, or a fused heteroaromatic ring having 7 to 12 ring carbon atoms;

[0036] R1, R2, R3, R4, R5, and R6 are the same or different, and each independently selected from hydrogen, deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an arylamino group having 12 to 24 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a heteroaryl group having 3 to 15 carbon atoms;

[0037] The substituents in R1, R2, R3, R4, R5, and R6 are the same or different, and each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 5 carbon atoms;

[0038] n1 to n6 are represented by n t and R1 to R6 are represented by R tIt is represented that t is a variable, representing any integer from 1 to 6, and n t represents the substituent R t the number of; when t is 1, 2, 3 or 4, n t is selected from 1, 2, 3, 4, 5, 6, 7; when t is 5, n t is selected from 1, 2, 3, 4; when t is 6, n t is selected from 1, 2, 3, 4, 5; when n t is greater than 1, any two Rs t are the same or different;

[0039] L is selected from a single bond or a substituted or unsubstituted arylene group with 6 to 12 carbon atoms;

[0040] The substituents in L are selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, and phenyl groups;

[0041] X is selected from a single bond, C(R7R8), Si(R9R 10 ), O, S, N(R 11 );

[0042] R7, R8, R9, R 10 and R 11 are the same or different, and each is independently selected from alkyl groups with 1 to 5 carbon atoms and aryl groups with 6 to 12 carbon atoms.

[0043] In this application, the description methods "each... is independently", "each... is separately and independently", and "each... is independently selected from" can be interchanged and should be understood in a broad sense. It can either mean that among different groups, the specific options expressed between the same symbols do not affect each other, or it can mean that within the same group, the specific options expressed between the same symbols do not affect each other. For example, " wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine", which means that in formula Q-1, there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options for each R" do not affect each other; in formula Q-2, each benzene ring of the biphenyl has q substituents R", the number q of the R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options for each R" do not affect each other.

[0044] In the present application, a term such as "substituted or unsubstituted" means that the functional group described after this term may or may not have a substituent (hereinafter, for the sake of convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means an aryl having a substituent Rc or an unsubstituted aryl. Among them, the above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, an arylamino group, an alkoxy group, a trialkylsilyl group, a triphenylsilyl group, an aryl group, a heteroaryl group, etc.

[0045] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the carbon atoms. For example, if R1 is a substituted arylene group having 12 carbon atoms, then the total number of carbon atoms of the arylene group and its substituents is 12.

[0046] In the present application, an aryl group refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. An aryl group can be a monocyclic aryl group (such as a phenyl group) or a polycyclic aryl group. In other words, an aryl group can be a monocyclic aryl group, a fused polycyclic aryl group, two or more monocyclic aryl groups conjugated through carbon-carbon bonds, a monocyclic aryl group and a fused polycyclic aryl group conjugated through carbon-carbon bonds, or two or more fused polycyclic aryl groups conjugated through carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups conjugated through carbon-carbon bonds can also be regarded as the aryl groups in the present application. Among them, the fused polycyclic aryl group can include, for example, a bicyclic fused aryl group (such as a naphthyl group), a tricyclic fused aryl group (such as a phenanthryl group, a fluorenyl group, an anthryl group), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, a biphenyl group, a terphenyl group, etc. are aryl groups. Examples of aryl groups can include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a benzo[9,10]phenanthryl group, etc. In the present application, the arylene group involved refers to a divalent group formed by an aryl group further losing one hydrogen atom.

[0047] In the present application, a substituted aryl group can be one or more hydrogen atoms in the aryl group being replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, etc. Specific examples of a heteroaryl-substituted aryl group include, but are not limited to, a phenyl group substituted with a dibenzofuranyl group, a phenyl group substituted with a dibenzothiophenyl group, a phenyl group substituted with a carbazolyl group, etc. It should be understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0048] In the present application, the aryl group as a substituent includes, for example but not limited to, a phenyl group, a biphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, an anthryl group, a phenanthryl group.

[0049] In the present application, a heteroaryl refers to a monovalent aromatic ring or its derivative containing at least one heteroatom in the ring, and the heteroatom can be at least one of B, O, N, P, Si, Se, and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. In other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems conjugated through carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuryl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, etc., without limitation. Among them, thienyl, furyl, phenanthrolinyl, etc. are heteroaryls of the single aromatic ring system type, and N-phenylcarbazolyl, N-pyridylcarbazolyl are heteroaryls of the polycyclic system type conjugated through carbon-carbon bonds. In the present application, the sub-heteroaryl involved refers to a divalent group formed by further removing one hydrogen atom from the heteroaryl.

[0050] In the present application, the substituted heteroaryl can be one or more than two hydrogen atoms in the heteroaryl being substituted by groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, etc. Specific examples of the aryl-substituted heteroaryl include, but are not limited to, phenyl-substituted dibenzofuryl, phenyl-substituted dibenzothienyl, phenyl-substituted carbazolyl, etc. It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0051] In the present application, the heteroaryl as a substituent is, for example but not limited to, carbazolyl, dibenzofuryl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, quinoline, isoquinoline.

[0052] In the present application, the non-positioned connecting bond refers to a single bond extending from the ring system It indicates that one end of the connecting bond can be connected to any position in the ring system penetrated by the bond, and the other end is connected to the rest of the compound molecule.

[0053] For example, as shown in formula (f) below, the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positioned connecting bonds penetrating the bicyclic ring, and the meaning it represents includes any possible connection mode shown in formulas (f-1) to (f-10).

[0054]

[0055] For another example, as shown in formula (X') below, the phenanthryl group represented by formula (X') is connected to other positions of the molecule through a non-positioned connecting bond extending from the middle of one benzene ring, and the meaning it represents includes any possible connection mode shown in formulas (X'-1) to (X'-4).

[0056]

[0057] The non-positioned substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be connected at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioned connecting bond, and the meaning it represents includes any possible connection mode shown in formulas (Y-1) to (Y-7).

[0058]

[0059] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0060] In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 5, 6, 7, 8, 9, 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

[0061] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.

[0062] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl, trifluoroethyl.

[0063] In the present application, specific examples of the deuterated alkyl group include, but are not limited to, trideuteriomethyl.

[0064] In this application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0065] In this application, specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, and the like.

[0066] In this application, specific examples of the arylamino group include, but are not limited to, diphenylamino, dinaphthylamino, dibenzylanilino, and the like.

[0067] In one embodiment of this application, A1, A2, A3, and A4 are each independently selected from a benzene ring a pyridine ring a naphthalene ring a 1,2,3,4-tetrahydronaphthalene ring dibenzodioxin a fluorene ring a phenanthrene ring a benzo[a]phenanthrene ring dibenzofuran dibenzothiophene carbazole benzimidazole

[0068] In one embodiment of this application, R1, R2, R3, R4, R5, and R6 are each independently selected from hydrogen, deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an arylamino group having 12 to 20 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, trimethylsilyl, triphenylsilyl, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 5 to 12 carbon atoms.

[0069] Optionally, the substituents in R1, R2, R3, R4, R5, and R6 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, and tert-butyl.

[0070] In one embodiment of this application, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

[0071] Optionally, the substituents in L are selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, and phenyl.

[0072] Further optionally, R1, R2, R3, R4, R5, and R6 are each independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, deuterium, fluorine, cyano, trideuteriomethyl, cyclohexyl, adamantyl, trifluoromethyl, diphenylamino, methoxy, trimethylsilyl, triphenylsilyl, phenyl, and deuterium-substituted phenyl Fluorine-substituted phenyl Naphthyl, biphenyl, carbazolyl.

[0073] Optionally, in Chemical Formula 1 selected from the group consisting of the following structures:

[0074]

[0075] wherein represents a chemical bond.

[0076] Optionally, R7, R8, R9, R 10 and R 11 are each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl.

[0077] Optionally, the organic compound is selected from the group consisting of the following compounds:

[0078]

[0079]

[0080]

[0081]

[0082]

[0083] The 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 contains the organic compound provided in the first aspect of the present application.

[0084] In a specific embodiment, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.

[0085] Optionally, the electronic component is an organic electroluminescent device.

[0086] Preferably, the organic light-emitting layer contains a guest material, and the guest material contains the organic compound.

[0087] Optionally, the organic electroluminescent device is a blue light device or a green light device.

[0088] In a specific embodiment, the electronic component is an organic electroluminescent device. As Figure 1 shown, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200 that are sequentially stacked.

[0089] Optionally, the anode 100 includes the following anode materials, which are preferably materials with a large work function (work function) that contribute to hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO∶Al or SnO2∶Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0090] Optionally, the hole transport layer 321 can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and this application does not make special limitations thereto. For example, the hole transport layer 321 can be HT-01.

[0091] Optionally, the electron blocking layer 322 can be composed of the organic compounds provided by this application or jointly composed of the organic compounds provided by this application and other materials. The electron blocking layer is selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. For example, the electron blocking layer can be HT-02.

[0092] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting material or can include a host material and a dopant material. Optionally, the organic light-emitting layer 330 is composed of a host material and a dopant material. The holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0093] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, and this application does not make special limitations thereto. In one embodiment of this application, the host material of the organic light-emitting layer 330 can be BH-01.

[0094] The dopant material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or its derivative, a compound having a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials, and this application does not make special limitations thereto. In one embodiment of this application, the dopant material of the organic light-emitting layer 330 can be the organic compound of this application.

[0095] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. In an embodiment of the present application, the electron transport layer 340 can be composed of ET-01 and LiQ.

[0096] In the present application, the cathode 200 can include a cathode material, which is a material with a small work function that helps electrons to be injected 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 their alloys; or multi-layer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode containing magnesium and silver is included as the cathode.

[0097] Optionally, as Figure 1 shown, a hole injection layer 310 can also be provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, and the present application does not make special restrictions on this. For example, the hole injection layer 310 can be F4-TCNQ.

[0098] Optionally, as Figure 1 shown, an electron injection layer 350 can 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 can include inorganic materials such as alkali metal sulfides and alkali metal halides, or can include complexes of alkali metals and organic substances. For example, the electron injection layer 350 can be Yb.

[0099] The third aspect of the present application provides an electronic device, including the electronic component provided by the second aspect of the present application.

[0100] According to an embodiment, as Figure 2 shown, the electronic device is a first electronic device 400, and the first electronic device 400 includes the above-mentioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices. For example, it can include, but is not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0101] According to another embodiment, as Figure 3As shown, the electronic device is the second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0102] The following combines synthesis examples to specifically illustrate the synthesis method of the organic compounds of the present application, but the present application is not limited thereby.

[0103] Compounds for which the synthesis method is not mentioned in the present application are all raw material products obtained through commercial channels.

[0104] Synthesis Example: Compound Synthesis

[0105] The intermediate secondary amine compounds required in the synthesis examples were synthesized using the following general method 1 or method 2:

[0106] Method 1:

[0107]

[0108] Method 2:

[0109]

[0110] 1. Synthesis of Intermediate III:

[0111]

[0112] Zinc chloride (27.5 g, 201.9 mmol) and tetrahydrofuran (800 mL) were added to a nitrogen-protected round-bottom flask, and the temperature was lowered to -5°C to 0°C under stirring; a tetrahydrofuran solution (151 mL, 151.4 mmol) of cyclohexylmagnesium chloride (1 M) was slowly added dropwise, and after stirring at a constant temperature for 0.5 h, the temperature was raised to 20°C to 25°C; 1,3-dibromo-2-chloro-5-iodobenzene (40 g, 100.9 mmol), tris(dibenzylideneacetone)dipalladium (4.6 g, 5.0 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (4.1 g, 10.1 mmol) were added to the reaction solution, and the reaction was stirred for 24 h; the reaction solution was poured into an aqueous potassium carbonate solution, extracted with dichloromethane, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure; the obtained crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the solvent to obtain Intermediate III (30.1 g, yield 85%).

[0113] Referring to the synthesis method of Intermediate III, Intermediate IV in Table 1 was synthesized, except that the raw material 1 in Table 1 was used instead of cyclohexylmagnesium chloride.

[0114] Table 1

[0115]

[0116] 2. Synthesis of Intermediate b1-1:

[0117]

[0118] Add 2,3-dichlorobromobenzene (2.94 g, 13.0 mmol), diphenylamine (2.0 g, 11.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.2 g, 0.2 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.2 g, 0.5 mmol), sodium tert-butoxide (1.7 g, 17.7 mmol) and toluene (30 mL) into a round-bottom flask under nitrogen protection. Heat the mixture to 105 °C - 110 °C under stirring and react for 4 h. Cool the reaction solution to room temperature, wash it with water, separate the organic phase, dry it with anhydrous magnesium sulfate, and remove the solvent under reduced pressure. Purify the obtained crude product by silica gel column chromatography using dichloromethane / n-heptane to obtain the intermediate b1-1 as a white solid (2.6 g, yield 70%).

[0119] Synthesize the intermediates listed in Table 2 by referring to the method of intermediate b1-1, with the difference that raw material 2 is used instead of 2,3-dichlorobromobenzene and raw material 3 is used instead of diphenylamine. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0120] Table 2

[0121]

[0122] 3. Synthesis of Intermediate b1

[0123]

[0124] Add intermediate b1-1 (1.57 g, 5.0 mmol), 3-(9-phenyl-9H-fluoren-9-yl)diphenylamine (2.25 g, 5.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.1 g, 0.1 mmol), 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (0.1 g, 0.2 mmol), sodium tert-butoxide (0.7 g, 7.5 mmol) and toluene (20 mL) into a round-bottom flask under nitrogen protection. Heat the mixture to 105 °C - 110 °C under stirring and react for 12 h. Cool the reaction solution to room temperature, wash it with water, separate the organic phase, dry it with anhydrous magnesium sulfate, and remove the solvent under reduced pressure. Purify the obtained crude product by silica gel column chromatography using dichloromethane / n-heptane to obtain the intermediate b1 as a white solid (2.92 g, yield 85%).

[0125] Synthesize the intermediates listed in Table 3 according to the method of intermediate b1, except that raw material 4 is used instead of intermediate b1-1, and raw material 5 is used instead of 3-(9-phenyl-9H-fluoren-9-yl)diphenylamine. Among them, the main raw materials used, the synthesized intermediates and their yields are shown in Table 3.

[0126] Table 3

[0127]

[0128]

[0129] 4. Synthesis of Compound II-1:

[0130]

[0131] Add intermediate b1 (3.0 g, 4.4 mmol) and tert-butylbenzene (100 mL) to a round-bottom flask under nitrogen protection, and cool to -60 °C to -65 °C under stirring; slowly dropwise add a pentane solution of tert-butyllithium (1.3 M) (4.0 mL, 5.2 mmol). After the addition is complete, warm to 55 °C to 60 °C and keep warm for 2 h; cool to -50 °C to -55 °C, and dropwise add boron tribromide (1.3 g, 5.2 mmol) to the reaction solution. Warm to 20 °C to 25 °C and keep warm for 1 h; cool to -5 °C to 0 °C, add diisopropylethylamine (1.1 g, 8.7 mmol) to the reaction solution, warm to 120 °C to 125 °C, and stir and react for 16 h; cool the reaction solution to room temperature, add water and dichloromethane to it, separate the organic phase, dry it with anhydrous magnesium sulfate, and remove the solvent under reduced pressure; the obtained crude product is purified by silica gel column chromatography using dichloromethane / n-heptane as the solvent, and then recrystallized and purified using toluene / n-heptane as the solvent to obtain white solid Compound II-1 (0.46 g, yield 17%), and the mass spectrum (m / z) = 661.3 [M+H] + ;

[0132] NMR data: 1 1H-NMR (400 MHz, CD2Cl2): 9.01 (d, 2H), 7.72 - 7.68 (m, 6H), 7.57 (t, 2H), 7.45 - 7.40 (m, 4H), 7.37 (d, 4H), 7.33 - 7.19 (m, 11H), 6.80 (d, 2H), 6.12 (s, 2H).

[0133] Synthesize the compounds listed in Table 4 according to the method of Compound II-1, except that raw material 6 is used instead of intermediate b1. Among them, the main raw materials used, the synthesized compounds and their yields, and mass spectra are shown in Table 4.

[0134] Table 4

[0135]

[0136]

[0137] Preparation and Evaluation of Organic Electroluminescent Devices

[0138] Example 1 Blue Organic Electroluminescent Device

[0139] The anode was prepared through the following process: An ITO substrate (manufactured by Corning) with a thickness of was cut into a size of 40 mm × 40 mm × 0.7 mm, and through a photolithography process, it was fabricated into an experimental substrate with patterns of cathode, anode, and insulating layer. Surface treatment was carried out using ultraviolet ozone and O2∶N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0140] F4-TCNQ was vacuum-evaporated on the experimental substrate (anode) to form a hole injection layer (HIL) with a thickness of , and HT-01 was evaporated on the hole injection layer to form a hole transport layer with a thickness of .

[0141] HT-02 was vacuum-evaporated on the hole transport layer to form an electron blocking layer with a thickness of .

[0142] On the electron blocking layer, BH-01 and Compound I-1 were co-evaporated at an evaporation ratio of 95%∶5% to form a blue emitting layer (EML) with a thickness of .

[0143] ET-01 and LiQ were mixed at a weight ratio of 1∶1 and evaporated to form an electron transport layer (ETL) with a thickness of , LiQ was evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of , and then magnesium (Mg) and silver (Ag) were mixed at an evaporation ratio of 1∶9 and vacuum-evaporated on the electron injection layer to form a cathode with a thickness of .

[0144] In addition, CP-1 with a thickness of was evaporated on the above-mentioned cathode to form an organic capping layer (CPL), thus completing the fabrication of the organic electroluminescent device.

[0145] Examples 2 - 8

[0146] Except that when forming the emitting layer, the compounds shown in Table 6 below were used instead of Compound I-1, the organic electroluminescent device was fabricated using the same method as in Example 1.

[0147] Comparative Examples 1 to 5

[0148] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Compound A, Compound B, Compound C, Compound D, and Compound E were used instead of Compound I-1 when forming the light-emitting layer.

[0149] The materials and structures used in the above examples and comparative examples are shown in the following table:

[0150] Table 5

[0151]

[0152]

[0153] For the organic electroluminescent device thus obtained, the device performance was analyzed under the condition of 20 mA / cm 2 , and the results are shown in Table 6:

[0154] Table 6

[0155]

[0156] As can be seen from the above table, in Examples 1 to 8, the compounds of the present application were used as the blue light host materials in the light-emitting layer of the blue organic electroluminescent device. Compared with Comparative Examples 1 to 5, the current efficiency was increased by at least 17.2%, and the lifetime was increased by at least 10%.

[0157] Therefore, when the organic compounds of the present application are used to prepare blue organic electroluminescent devices, the luminous efficiency of the organic electroluminescent devices can be effectively improved and their lifetimes can be extended.

Claims

1. An organic compound, wherein, The structure of the organic compound is shown in Chemical Formula 1: Wherein, A1, A2, A3 and A4 are the same or different, and each independently selected from a benzene ring, a naphthalene ring, a 1,2,3,4-tetrahydronaphthalene ring; R1, R2, R3, R4, R5 and R6 are the same or different, and each independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, deuterium, fluorine, cyano, trideuteromethyl, cyclohexyl, adamantyl, trifluoromethyl, methoxy, trimethylsilyl, phenyl, deuterium-substituted phenyl; n1 to n6 are represented by n t ; R1 to R6 are represented by R t ; t is a variable representing any integer from 1 to 6, and n t represents the number of substituents R t ; when t is 1, 2, 3 or 4, n t is selected from 1, 2, 3, 4; when t is 5, n t is selected from 1, 2, 3, 4; when t is 6, n t is selected from 1, 2, 3, 4, 5; when n t is greater than 1, any two R t may be the same or different; L is selected from a single bond, an unsubstituted phenylene group; X is selected from a single bond, C(R7R8), Si(R9R 10 ), O, S, N(R 11 ); R7, R8, R9, R 10 and R 11 are the same or different and each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl.

2. The organic compound according to claim 1, wherein, in Chemical Formula 1 selected from the group consisting of the following structures: Among them, represents a chemical bond.

3. The organic compound according to claim 1, wherein, The organic compound is selected from the group consisting of the following compounds:

4. 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; Among them, The functional layer contains the organic compound according to any one of claims 1 to 3.

5. The electronic component according to claim 4, wherein, The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the organic compound.

6. The electronic component according to claim 4, wherein, The organic light-emitting layer contains a guest material, and the guest material contains the organic compound.

7. An electronic device, comprising the electronic component according to any one of claims 4 to 6.

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