Organic compound and electronic component and electronic device using the same

Abstract

The present invention relates to an organic compound and an electronic component and an electronic device using the same. The organic compound has a structure shown in Formula I, and the organic compound is applied to an organic electroluminescent device to significantly improve the performance of the device.

Description

Technical Field

[0001] The present application relates to the 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.

[0003] Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode which are stacked in sequence. When voltage is applied between 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, which are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward. Summary of the invention

[0004] 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.

[0005] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0006]

[0007] wherein R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 18 carbon atoms, or R1 and R2 and the carbon atom to which they are connected together form a saturated or unsaturated 3 to 15-membered ring;

[0008] Each R is independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0009] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5 or 6;

[0010] 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;

[0011] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] The substituents in L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0013] 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.

[0014] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0015] The parent nucleus of the compound of the present application is a fluorenyl group, and a 3-phenyl group substituted with phenyl groups at positions 1 and 2 is connected to the same benzene ring of the fluorenyl group. and aromatic amine; this special connection mode, on the one hand, the two substituents on the same benzene ring of the fluorenyl group can greatly enhance the spatial configuration ability of the molecule, increase the glass transition temperature of the material, and improve the film-forming property of the material; on the other hand, the aromatic amine and the phenyl substituted by the 1,2 phenyl group are connected to the same benzene ring of the fluorenyl group. This connection mode expands the conjugated region of the molecule, so that the compound has suitable HOMO and LUMO energy levels and has a higher hole mobility. Using the compound of the present application as a hole transport material can improve the carrier balance in the light-emitting layer, broaden the carrier recombination region, and improve the device efficiency and life.

[0016] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] 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.

[0018] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0019] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0020] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0021] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0022] Description of Reference Numerals

[0023] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. DETAILED DESCRIPTION

[0024] 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.

[0025] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0026]

[0027] wherein R1 and R2 are the same or different and are independently selected from an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 18 carbon atoms, or R1 and R2 and the carbon atom to which they are connected together form a saturated or unsaturated 3 to 15-membered ring;

[0028] Each R is independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0029] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5 or 6;

[0030] 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;

[0031] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0032] The substituents in L1, L2, Ar1 and Ar2 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0033] 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.

[0034] 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 cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0035] 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.

[0036] 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.

[0037] 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, cycloalkyl groups, halogenated alkyl groups, deuterated alkyl groups, etc. Specific examples of aryl groups substituted with heteroaryl groups include, but are not limited to, phenyl groups substituted with dibenzofuranyl groups, phenyl groups substituted with dibenzothiophene groups, phenyl groups substituted with pyridine 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.

[0038] 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 connected 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.

[0039] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, deuterated alkyl 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0044] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0045] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0046] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0047] In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentane, cyclohexane, and adamantane.

[0048] 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):

[0049]

[0050] 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):

[0051]

[0052] In some embodiments of the present application, R1 and R2 are the same or different and are independently selected from methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl or biphenyl, or R1 and R2 and the carbon atom to which they are connected together form a cyclopentane group. Cyclohexane or fluorene ring

[0053] In some embodiments of the present application, the organic compound has a structure shown in Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6, Formula 7, Formula 8, Formula 9, Formula 10, Formula 11 or Formula 12:

[0054]

[0055] In some embodiments of the present application, each R is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0056] 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, or a substituted or unsubstituted heteroarylene group having 5 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, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0057] 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.

[0058] 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.

[0059] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0060] 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:

[0061]

[0062] Optionally, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0063]

[0064] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. 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, 10, 20, 21, 22, 23, 24 or 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0065] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0066] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted cyclopentanespirofluorene, substituted or unsubstituted cyclohexanespirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0067] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl or phenyl.

[0068] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0069]

[0070]

[0071] Further optionally, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0072]

[0073] In some embodiments of the present application, The same or different, and each independently selected from the group consisting of the following groups:

[0074]

[0075] Optionally, The same or different, and each independently selected from the group consisting of the following groups:

[0076]

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

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] 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.

[0089] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.

[0090] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0091] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0092] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer contains the organic compound of the present application.

[0093] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1As shown, the organic electroluminescent device may include a stacked anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 340 and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.

[0094] Optionally, the anode 100 includes the following anode materials, which are preferably materials with a large work function that facilitate 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 are not limited thereto. Preferably, a transparent electrode including indium tin oxide (indiumtin oxide) (ITO) as an anode is included.

[0095] Optionally, the hole transport layer 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 this application does not make special provisions for this. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0096]

[0097] In a specific embodiment, the first hole transport layer 321 is HT-1.

[0098] In another specific embodiment, the second hole transport layer 322 is the compound of the present application.

[0099] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined 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 guest material, thereby enabling the guest material to emit light.

[0100] The main material of the organic light-emitting layer 330 can 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 on this. The main material can be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is CBP.

[0101] The guest material of the organic light-emitting layer 330 can be selected according 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 guest material include, but are not limited to,

[0102]

[0103] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is Ir(piq)2(acac).

[0104] 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, 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. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-21, BimiBphen, 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-20 and LiQ.

[0105]

[0106]

[0107] 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.

[0108] Alternatively, if Figure 1As shown, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of injecting holes into the first 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 special restrictions on this. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0109]

[0110] In a specific embodiment of the present application, the hole injection layer 310 is m-MTDATA.

[0111] Alternatively, if Figure 1 As shown, an electron injection layer 350 is further 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. For example, the electron injection layer 350 includes LiQ.

[0112] According to another embodiment, the electronic component is a photoelectric conversion device. Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.

[0113] According to a specific implementation mode, Figure 3 As shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 which are stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0114] Optionally, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, in one embodiment of the present application, the solar cell comprises an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer and a cathode stacked in sequence, wherein the hole transport layer comprises the organic compound of the present application.

[0115] In a third aspect, the present application provides an electronic device, comprising the electronic component provided in the second aspect of the present application.

[0116] According to one embodiment, Figure 2As 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, such as but not limited to a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0117] According to another embodiment, Figure 4 As shown, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 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.

[0118] The synthesis method of the organic compound of the present application is specifically described below in conjunction with synthesis examples, but the present application is not limited thereto.

[0119] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0120] Synthesis example

[0121] 1. Synthesis of IM aI:

[0122]

[0123] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and 3-chloro-2-bromo-1-iodobenzene (100.0 g, 315.1 mmol), phenylboric acid (80.68 g, 661.7 mmol), bis(triphenyl)palladium dichloride (Pd(PPh3)2Cl2, 2.21 g, 3.15 mmol) and potassium carbonate (K2CO3, 130.65 g, 945.33 mmol) were added in sequence, and a mixed solvent of dimethylol ether (DME, 800 mL) and water (200 mL) was added. Stirring was started, the temperature was raised to 75°C to 78°C for reaction for 56 hours, and after the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM a-1 (66.74 g, yield 80%).

[0124] 2. Synthesis of IM a-II:

[0125]

[0126] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 min, and IM aI (66.7 g, 251.9 mmol), biboric acid pinacol ester (70.22 g, 277.1 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 2.31 g, 2.5 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 2.40 g, 5.0 mmol), potassium acetate (49.43 g, 503.87 mmol) and 1,4-dioxane (660 mL) were added in sequence. Stirring was started, the temperature was raised to 92°C to 100°C for reaction for 6 h, and after the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM a-II (73.60 g, yield 82%).

[0127] 3. Synthesis of IM a-III:

[0128]

[0129] Nitrogen (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser for replacement for 15 minutes, and IM a-II (73.60 g, 206.58 mmol), reactant A (63.55 g, 206.58 mmol), bis(triphenyl)palladium dichloride (Pd(Ph3P)2Cl2, 0.725 g, 2.06 mmol) and potassium carbonate (71.38 g, 516.46 mmol) were added in sequence, and a mixed solvent of dimethylol ether (736 mL) and water (147.2 mL) was added. Stirring was started, the temperature was raised to 75°C to 78°C for reaction for 12 hours, and after the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM a-III (66.09 g, yield 72%).

[0130] The intermediates listed in Table 1 were synthesized by referring to the method of IM a-III, wherein the main reagents and the synthesized intermediate IM a-II remained unchanged, except that the raw materials listed in the raw material 1 column were used instead of reactant A, and the yields are shown in Table 1.

[0131] Table 1

[0132]

[0133]

[0134] Synthesis Example 1: Synthesis of Compound 2

[0135]

[0136] Nitrogen (0.200 L / min) was introduced into a three-necked flask equipped with mechanical stirring, a thermometer and a spherical condenser for replacement for 15 min, and IMj-III (15 g, 32.82 mmol), 4-aminobiphenyl (5.55 g, 32.82 mmol), tris(dibenzylideneacetone)dipalladium (0.15 g, 0.16 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.16 g, 0.33 mmol), sodium tert-butoxide (t-BuONa, 4.73 g, 49.23 mmol) and toluene (PhMe, 150 mL) were added in sequence. The reaction was refluxed at 105°C to 110°C for 3 h. After the reaction was completed, the mixture was cooled to room temperature. The organic phase was washed with water, and then anhydrous magnesium sulfate was added to dry the organic phase. After filtering, the filtrate was distilled under reduced pressure to remove the solvent; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM 2-1 (15.48 g, yield 76%).

[0137]

[0138] Into a three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser, nitrogen (0.100 L / min) was introduced for replacement for 15 min, and IM 2-1 (15 g, 25.43 mmol), 4-bromobiphenyl (5.93 g, 25.43 mmol), tris(dibenzylideneacetone)dipalladium (0.116 g, 0.13 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (S-Phos, 0.11 g, 0.25 mmol), sodium tert-butoxide (3.67 g, 38.15 mmol) and toluene (150 mL) were added in sequence. The mixture was refluxed at 105°C to 110°C for 6 h. After the reaction was completed, the mixture was cooled to room temperature. After washing the organic phase with water, the organic phase was separated, anhydrous magnesium sulfate was added to dry the organic phase, and the filtrate was filtered and the solvent was removed by distillation under reduced pressure; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid compound 1 (8.49 g, yield 47%). Mass spectrum (m / z) = 742.3 [M+H] + .

[0139] The compounds listed in Table 2 were synthesized by referring to the method of compound 2, except that raw material 2 was used instead of IMj-III, raw material 3 was used instead of 4-aminobiphenyl, and raw material 4 was used instead of 4-bromobiphenyl. The main raw materials used, the synthesized compounds, and their final step yields and mass spectra are shown in Table 2.

[0140] Table 2

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] The NMR data of some compounds are shown in Table 3 below

[0148] Table 3

[0149]

[0150]

[0151] Example of fabrication and evaluation of organic electroluminescent devices

[0152] Example 1: Preparation of red organic electroluminescent device

[0153] The anode was prepared by the following process: The ITO / Ag / ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness), and a photolithography process was used to prepare it into an experimental substrate with an anode and an insulating layer pattern. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode 1, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0154] m-MTDATA was vacuum-deposited on the experimental substrate to form a layer with a thickness of hole injection layer.

[0155] HT-1 was vacuum-deposited on the hole injection layer to form a layer with a thickness of The first hole transport layer is formed by a plurality of holes.

[0156] Compound 2 is evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is formed by a plurality of holes.

[0157] On the second hole transport layer, CBP and Ir(piq)2(acac) were evaporated at an evaporation rate ratio of 100:2 to form a layer with a thickness of of an organic light-emitting layer.

[0158] On the organic light emitting layer, ET-20 and LiQ were evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of LiQ is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a layer with a thickness of cathode.

[0159] In addition, compound CP-1 is evaporated on the cathode to form a layer with a thickness of A covering layer is formed, thereby completing the manufacture of the organic light-emitting device.

[0160] Embodiments 2 to 34

[0161] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound in Table 4 was used instead of Compound 2 when forming the second hole transport layer.

[0162] Comparative Example 1-Comparative Example 3

[0163] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound A, compound B, and compound C were used instead of compound 2 when forming the second hole transport layer.

[0164] Among them, when preparing the devices of the above embodiments and comparative examples, the structures of the compounds used are as follows:

[0165]

[0166]

[0167] The performance of the red organic electroluminescent devices prepared in Examples 1 to 34 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of 20mA / cm 2 The T95 life was tested under the conditions of , and the test results are shown in Table 4 below.

[0168] Table 4

[0169]

[0170]

[0171] Referring to Table 4 above, it can be seen that when the compound of the present invention is used in the second hole transport layer of the red organic electroluminescent device, the device performance can be greatly improved. Specifically, compared with the organic electroluminescent devices of Comparative Examples 1 to 3, the current efficiency of the organic electroluminescent devices of Examples 1 to 34 is at least improved by 12.4%, and the T95 life is at least improved by 11%.

[0172] 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.

[0173] 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 I: wherein R1 and R2 are the same or different and are independently selected from methyl or phenyl, or R1 and R2 and the carbon atom to which they are commonly connected form a fluorene ring; each R is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; n represents the number of R, and n is selected from 0; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group; The substituents in L1 and L2 are each independently selected from deuterium or phenyl; Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, methyl or phenyl.

2. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the group consisting of:

3. The organic compound according to claim 1, wherein The same or different, and each independently selected from the group consisting of the following groups:

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

5. 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 4.

6. The electronic component according to claim 5, wherein The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

7. The electronic component according to claim 6, wherein: The electronic component is an organic electroluminescent device or a photoelectric conversion device.

8. The electronic component according to claim 7, wherein: The organic electroluminescent device is a red organic electroluminescent device.

9. An electronic device, characterized in that The electronic device includes the electronic component according to any one of claims 5 to 8.

Images