Organic compound, and electronic element and electronic device using same

Abstract

The present invention relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound has a structure as shown in a formula 1, and when the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, and in particular to an organic compound and an electronic component and an electronic device using the organic compound. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Such electronic components usually include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode. When voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward 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 outward.

[0003] Generally speaking, in the host material / dopant system, the selection of the host material is crucial because the host material has an important influence on the efficiency and life of the light-emitting device. The host material with excellent performance should have a suitable molecular weight, a high glass transition temperature and thermal decomposition temperature, high electrochemical stability and good interface contact with the adjacent functional layer materials. For blue light host materials, the material is required to have good carrier transport ability and a suitable triplet energy level to ensure that energy can be effectively transferred from the host material to the guest material during the light-emitting process, thereby achieving higher device efficiency.

[0004] The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the invention

[0005] The purpose of the present application is to provide an organic compound and an electronic component and an electronic device using the same. The organic compound is used in an organic electroluminescent device to improve the performance of the device.

[0006] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0007]

[0008] Wherein, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from a structure represented by Formula 2 or Formula 3;

[0009] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0010] The substituents in Ar1, Ar2, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

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

[0012] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n is greater than 1, any two R are the same or different;

[0013] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3 or 4, when n1 is greater than 1, any two R1 are the same or different;

[0014] n2 represents the number of R2, n2 is selected from 0, 1, 2, 3, 4 or 5, when n2 is greater than 1, any two R2 are the same or different;

[0015] n3 represents the number of R3, n3 is selected from 0, 1, 2, 3, 4 or 5, when n3 is greater than 1, any two R3 are the same or different;

[0016] n4 represents the number of R4, n4 is selected from 0, 1, 2, 3 or 4, when n4 is greater than 1, any two R4 are the same or different;

[0017] n5 represents the number of R5, n5 is selected from 0, 1, 2, 3 or 4, when n5 is greater than 1, any two R5 are the same or different;

[0018] n6 represents the number of R6, and n6 is selected from 0, 1, 2, 3, 4 or 5. When n6 is greater than 1, any two R6 are the same or different.

[0019] A second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

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

[0021] The compound structure of the present application contains 10,10-diphenyl-10H-dibenzooxasilane, carbazole and triazine groups. On the one hand, the molecular distortion of 10,10-diphenyl-10H-dibenzooxasilane is relatively large, which gives the compound a higher glass transition temperature, allowing the compound to form a better amorphous film, and the oxygen atom has two pairs of lone pairs of electrons, which can enhance the electron transport performance of 10,10-diphenyl-10H-dibenzooxasilane; on the other hand, 10,10-diphenyl-10H-dibenzooxasilane gives the compound higher rigidity, which can inhibit non-radiative attenuation in the electroluminescence process and improve the luminous efficiency; in addition, the triazine group substituted by carbazole can ensure that the entire molecule has a higher first excited triplet energy level, which meets the energy level requirements of the blue phosphorescent host material. When the compound of the present application is used as an electron transport material in a hybrid blue light host material, the energy transfer efficiency from the host material to the blue light doping material can be improved, and non-radiative attenuation can be suppressed, thereby improving the efficiency of the device; and the higher glass transition temperature of the compound can ensure that the light-emitting layer forms a good amorphous film, and the film morphology of the device is not easy to change during long-term operation, thereby improving the life of the device.

[0022] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0024] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0025] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0026] Description of Reference Numerals

[0027] 100, anode 200, cathode 300, functional layer 310, hole injection layer 321, hole transport layer

[0028] 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0029] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed 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, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0030] In a first aspect, the present application provides an organic compound having a structure shown in Formula 1:

[0031]

[0032] Wherein, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from a structure represented by Formula 2 or Formula 3;

[0033] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0034] The substituents in Ar1, Ar2, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms;

[0035] R, R1, R2, R3, R4, R5 and R6 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms;

[0036] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n is greater than 1, any two R are the same or different;

[0037] n1 represents the number of R1, n1 is selected from 0, 1, 2, 3 or 4, when n1 is greater than 1, any two R1 are the same or different;

[0038] n2 represents the number of R2, n2 is selected from 0, 1, 2, 3, 4 or 5, when n2 is greater than 1, any two R2 are the same or different;

[0039] n3 represents the number of R3, n3 is selected from 0, 1, 2, 3, 4 or 5, when n3 is greater than 1, any two R3 are the same or different;

[0040] n4 represents the number of R4, n4 is selected from 0, 1, 2, 3 or 4, when n4 is greater than 1, any two R4 are the same or different;

[0041] n5 represents the number of R5, n5 is selected from 0, 1, 2, 3 or 4, when n5 is greater than 1, any two R5 are the same or different;

[0042] n6 represents the number of R6, and n6 is selected from 0, 1, 2, 3, 4 or 5. When n6 is greater than 1, any two R6 are the same or different.

[0043] In this application, the descriptions "each independently selected from" and "respectively independently selected from" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by 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, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of 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 of each R" do not affect each other.

[0044] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl or non-substituted aryl having a substituent Rc. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a triphenylsilyl group, a deuterated alkyl 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 the total number of carbon atoms. For example, if L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0046] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, and two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include a dicyclic condensed aryl (e.g., naphthyl), a tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0047] In the present application, the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, halogenated alkyl groups, deuterated alkyl groups, triphenylsilyl groups, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl groups, dibenzothiophene-substituted phenyl groups, pyridine-substituted phenyl groups, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having 18 carbon atoms refers to the total number of carbon atoms in the aryl group and the substituents being 18.

[0048] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0049] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are substituted by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, halogenated alkyl groups, deuterated alkyl groups, triphenylsilyl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl groups, phenyl-substituted dibenzothienyl groups, phenyl-substituted pyridyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0050] In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0051] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. Specific examples of the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0052] In the present application, the carbon number of the alkyl group having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group 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, and the like.

[0053] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0054] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0055] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0056] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0057] In this application, an unpositioned connecting bond refers to a single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0058]

[0059] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0060]

[0061] In some embodiments of the present application, the organic compound is selected from the structure shown in the following formula I, formula II, formula III, formula IV or formula V:

[0062]

[0063] In some embodiments of the present application, R, R1, R2, R3, R4, R5 and R6 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, trifluoromethyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0064] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms. For example, L1 and L2 are 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 or 18 carbon atoms.

[0065] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

[0066] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

[0067] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0068] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:

[0069]

[0070] Optionally, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0071]

[0072] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 24 carbon atoms, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from the structure represented by Formula 2 or Formula 3. For example, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms, or a structure shown in Formula 2 or 3, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2 or 3.

[0073] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, triphenylsilyl, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

[0074] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted silanyl group, or a structure shown in Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from the structure shown in Formula 2 or Formula 3.

[0075] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, triphenylsilyl or phenyl.

[0076] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0077]

[0078]

[0079] and at least one of Ar1 and Ar2 is selected from

[0080] In some embodiments of the present application, Ar1 is selected from the group consisting of the following groups:

[0081]

[0082] Ar2 is selected from

[0083] Further optionally, Ar1 is selected from the group consisting of the following groups:

[0084]

[0085]

[0086] Ar2 is selected from the group consisting of:

[0087]

[0088] In some embodiments of the present application, Selected from the group consisting of:

[0089]

[0090] Selected from

[0091] In some embodiments of the present application, Selected from the group consisting of:

[0092]

[0093]

[0094] Selected from the group consisting of:

[0095]

[0096] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect, the present application provides an electronic component, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0104] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound described in the present application.

[0105] Optionally, the electronic component is an organic electroluminescent device.

[0106] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1 As 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 which are stacked in sequence.

[0107] In a specific embodiment, the organic electroluminescent device is a blue organic electroluminescent device.

[0108] Optionally, the anode 100 includes the following anode material, which is optionally a material with a large work function that facilitates 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); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0109] Optionally, the hole transport layer 321 includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and those skilled in the art can select them with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of the following compounds:

[0110]

[0111]

[0112] In one specific embodiment, the hole transport layer 321 is HT-39.

[0113] Optionally, the electron blocking layer 322 includes one or more electron blocking materials, and the electron blocking material can be selected from carbazole polymers or other types of compounds, which are not specifically limited in the present application. In a specific embodiment, the electron blocking layer 330 is SiCzCz.

[0114] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a main material and a doping material. Optionally, the organic light-emitting layer 330 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.

[0115] The main material of the organic light-emitting layer 330 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special restrictions thereon. The main material may be a single main material or a mixed main material.

[0116] In one embodiment of the present application, the main material of the organic light-emitting layer 330 is a compound SiCzCz and the organic compounds of the present application.

[0117] The doping material of the organic light emitting layer 330 can be selected with reference to the prior art, for example, it can be selected from iridium (III) organic metal complex, platinum (II) organic metal complex, ruthenium (II) complex, etc. Specific examples of the doped material include, but are not limited to,

[0118]

[0119]

[0120] In one embodiment of the present application, the doping material of the organic light-emitting layer 330 is BD.

[0121] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials, and the electron transport material can generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc., and specific examples include but are not limited to ET-21, Bphen, NBphen, DBimiBphen, BimiBphen and other 1,10-phenanthroline compounds, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below. In one embodiment of the present application, the electron transport layer 340 is composed of ET-21 and LiQ.

[0122]

[0123] In the present application, cathode 200 may include a cathode material, which is a material with a small work function that helps inject electrons into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.

[0124] Alternatively, if Figure 1 As shown, a hole injection layer 310 may 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 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0125]

[0126] In a specific embodiment of the present application, the hole injection layer 310 is HAT-CN.

[0127] Alternatively, if Figure 1 As shown, an electron injection layer 350 is also 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 inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of alkali metals and organic matter. In a specific embodiment of the present application, the electron injection layer 350 is Yb.

[0128] A third aspect of the present application provides an electronic device, comprising the electronic component provided by the second aspect of the present application.

[0129] According to one embodiment, Figure 2 As 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, including but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc. The following is a specific description of the synthesis method of the organic compound of the present application in conjunction with the synthesis example, but the present application is not limited thereto.

[0130] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0131] Synthesis example: intermediate synthesis

[0132] 1. Synthesis of Sub-a1:

[0133]

[0134] Under nitrogen atmosphere, RM-1 (CAS: 2251736-11-3, 30.10 g, 70 mmol) and tetrahydrofuran (dried, 250 mL) were added to a 500 mL three-necked flask, the system was cooled to -78 ° C, n-butyl lithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise, and after the addition was completed, the mixture was stirred at -78 ° C for 1 h; trimethyl borate (10.91 g, 05mmol), and after the addition was completed, the temperature was kept at -78°C for 1h, and then the system was allowed to warm up to room temperature naturally; dilute hydrochloric acid (2M, 58mL) was added dropwise to the reaction solution and stirred for 30min; dichloromethane extraction (100mL×3 times) was performed, and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product; the crude product was slurried with n-heptane and filtered to obtain a white solid Sub-a1 (16.0g, yield 58%).

[0135] Sub-a2 to Sub-a10 listed in Table 1 were synthesized by referring to the synthesis method of Sub-a1, except that reactant A was used instead of RM-1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1.

[0136] Table 1

[0137]

[0138]

[0139] 2. Synthesis of Sub-b1:

[0140]

[0141] Under nitrogen atmosphere, RM-2 (CAS: 24209-95-8, 23.64 g, 75 mmol), Sub-a1 (19.72 g, 50 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (240 mL) and deionized water (60 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to 65°C to 70°C for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was recrystallized from toluene to obtain a white solid Sub-b1 (16.60 g, yield 53%).

[0142] Sub-b2 to Sub-b5 listed in Table 2 were synthesized by referring to the synthesis method of Sub-b1, except that reactant B was used instead of RM-2, and reactant C was used instead of Sub-a1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 2.

[0143] Table 2

[0144]

[0145] Synthesis Example 1: Synthesis of Compound 2:

[0146]

[0147] Under nitrogen atmosphere, Sub-d1 (12.58 g, 20 mmol), 4-biphenylboronic acid (4.36 g, 22 mmol), palladium acetate (Pd(OAc)2, 0.045 g, 0.2 mmol), 2-dicyclohexylphosphine-2', 4', 6'triisopropylbiphenyl (XPhos, 0.19 g, 0.4 mmol), anhydrous potassium carbonate (5.53 g, 40 mmol), toluene (120 mL), tetrahydrofuran (30 mL) and deionized water (30 mL) were added to a 500 mL three-necked flask in sequence, and stirring and heating were started. The temperature was raised to reflux reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid compound 2 (10.1 g, yield 68%), mass spectrum (m / z) = 747.25 [M+H]+ .

[0148] The compounds listed in Table 3 were synthesized by referring to the synthesis method of compound 2, except that reactant D was used instead of Sub-b1, and reactant E was used instead of 4-biphenylboronic acid. The main raw materials used, the synthesized compounds, their mass spectra and yields are shown in Table 3.

[0149] Table 3

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] Compound 32 NMR: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm8.76(s,2H),8.18-8.08(m,7H),8.01( d,1H),7.65(d,4H),7.60(d,4H),7.57-7.43(m,8H),7.40-7.20(m,11H),6.96(t,1H).

[0157] Example 1: Blue organic electroluminescent device

[0158] First, the anode pretreatment is carried out through the following process: The ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (height), and surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate was also cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0159] HAT-CN was vacuum-deposited on the experimental substrate (anode) to form a of the hole injection layer.

[0160] HT-39 was vacuum-deposited on the hole injection layer to form a layer with a thickness of hole transport layer.

[0161] SiCzCz is vacuum evaporated on the hole transport layer to form a layer with a thickness of electron blocking layer.

[0162] Compound 2: SiCzCz: BD is co-evaporated at an evaporation rate ratio of 60:27:13 to form a film with a thickness of of an organic light-emitting layer.

[0163] On the organic light emitting layer, compound ET-21 and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of The electron transport layer is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, aluminum (Al) is vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.

[0164] In addition, the thickness of the vacuum evaporation layer on the cathode is CP-1, thereby completing the manufacture of blue organic electroluminescent devices.

[0165] Embodiments 2 to 32

[0166] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound shown in Table 4 below was used instead of Compound 2 in Example 1 when preparing the light-emitting layer.

[0167] Comparative Examples 1 to 4

[0168] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B, compound C and compound D were used to replace compound 1 in Example 1 when preparing the light-emitting layer.

[0169] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

[0170]

[0171]

[0172] The performance of the blue organic electroluminescent devices prepared in Examples 1 to 32 and Comparative Examples 1 to 4 was tested. Specifically, the voltage, efficiency and life characteristics of the devices were tested at a brightness of 1000 nit. The test results are shown in Table 4.

[0173] Table 4

[0174]

[0175] According to the results in Table 4, the current efficiency of Examples 1 to 32 using the organic compounds of the present invention as the mixed host material in the blue organic electroluminescent device is improved by at least 12.14% and the T95 life is improved by at least 13.4% compared with Comparative Examples 1 to 4 corresponding to the devices using the known compounds.

[0176] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings; however, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, a variety of simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the protection scope of the present application.

[0177] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: Wherein, Ar1 and Ar2 are the same or different and are independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from a structure represented by Formula 2 or Formula 3; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; The substituents in Ar1, Ar2, L1 and L2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; R, R1, R2, R3, R4, R5 and R6 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 3 to 12 carbon atoms; n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8. When n is greater than 1, any two R are the same or different; n1 represents the number of R1, n1 is selected from 0, 1, 2, 3 or 4, when n1 is greater than 1, any two R1 are the same or different; n2 represents the number of R2, n2 is selected from 0, 1, 2, 3, 4 or 5, when n2 is greater than 1, any two R2 are the same or different; n3 represents the number of R3, n3 is selected from 0, 1, 2, 3, 4 or 5, when n3 is greater than 1, any two R3 are the same or different; n4 represents the number of R4, n4 is selected from 0, 1, 2, 3 or 4, when n4 is greater than 1, any two R4 are the same or different; n5 represents the number of R5, n5 is selected from 0, 1, 2, 3 or 4, when n5 is greater than 1, any two R5 are the same or different; n6 represents the number of R6, and n6 is selected from 0, 1, 2, 3, 4 or 5. When n6 is greater than 1, any two R6 are the same or different.

2. The organic compound according to claim 1, wherein R, R1, R2, R3, R4, R5 and R6 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, trifluoromethyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

3. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms; Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, or a phenyl group.

4. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

5. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from a structure represented by Formula 2 or Formula 3; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, triphenylsilyl, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

6. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted silyl group, or a structure represented by Formula 2 or Formula 3, and at least one of Ar1 and Ar2 is selected from a structure represented by Formula 2 or Formula 3; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, triphenylsilyl or phenyl.

7. The organic compound according to claim 1, wherein Ar1 is selected from the group consisting of: Ar2 is selected from 8. The organic compound according to claim 1, wherein The organic compound is selected from the group consisting of the following compounds:

9. An electronic component, characterized in that The electronic component comprises an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound according to any one of claims 1 to 8.

10. The electronic component according to claim 9, wherein The functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the organic compound; Optionally, the electronic component is an organic electroluminescent device.

11. An electronic device, characterized in that The electronic device comprises the electronic component according to claim 9 or 10.

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