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 I. 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 same. 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 L1 is selected from phenylene, deuterium-substituted phenylene, and phenyl-substituted phenylene;

[0008] Ar1 is selected from phenyl, deuterium-substituted phenyl, naphthyl, deuterium-substituted naphthyl, biphenyl, deuterium-substituted biphenyl;

[0009] X is selected from O, S or N(R1);

[0010] R1 is selected from an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms;

[0011] L, L2 and L3 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, and a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms;

[0012] Ar2 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0013] The substituents in L, L2, L3 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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;

[0014] Each R is independently selected from deuterium, a halogen group, a cyano group, 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0015] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n is greater than 1, any two Rs are the same or different.

[0016] 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.

[0017] A third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect of the present application.

[0018] The parent core of the compound of the present application is dimethylfluorenyl The 3rd position of the dimethylfluorenyl is connected to an aromatic amine substituted with a heteroaromatic ring, and the 5th position is connected to a specific aromatic group (biphenyl, naphthyl-substituted phenyl, terphenyl). On the one hand, the connection of the aromatic amine substituted with a heteroaromatic ring to the 3rd position of the dimethylfluorenyl can increase the degree of molecular conjugation, effectively improve the transmission efficiency of the compound, and make the compound have a high Tg, so when the OLED device is driven, it can prevent the compound from crystallizing, thereby increasing the service life of the device; and the specific aromatic group at the 5th position makes the twist angle between the molecules larger, so that while basically maintaining the morphology of the molecules themselves, it can effectively reduce the interaction between the molecules, enhance the amorphous state of the material, and improve the film-forming properties of the material. Using this material in the second hole transport layer of an organic electroluminescent device can effectively enhance the device efficiency and increase the device life.

[0019] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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.

[0021] Figure 1 It is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of the present application.

[0022] Figure 2 It is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0023] Figure 3 It is a schematic structural diagram of a photoelectric conversion device according to one embodiment of the present application.

[0024] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0025] Description of Reference Numerals

[0026] 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, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device DETAILED DESCRIPTION

[0027] 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.

[0028] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

[0029]

[0030] wherein L1 is selected from phenylene, deuterium-substituted phenylene, and phenyl-substituted phenylene;

[0031] Ar1 is selected from phenyl, deuterium-substituted phenyl, naphthyl, deuterium-substituted naphthyl, biphenyl, deuterium-substituted biphenyl;

[0032] X is selected from O, S or N(R1);

[0033] R1 is selected from an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms;

[0034] L, L2 and L3 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, and a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms;

[0035] Ar2 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0036] The substituents in L, L2, L3 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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;

[0037] Each R is independently selected from deuterium, a halogen group, a cyano group, 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0038] n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n is greater than 1, any two Rs are the same or different.

[0039] In this application, the descriptions used in the phrases "each ... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They 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.

[0040] 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 deuterated alkyl group, a halogenated alkyl group, an aryl group, a heteroaryl group, etc.

[0041] 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.

[0042] 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, Spirobifluorenyl In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0043] In the present application, terphenyl includes

[0044] In the present application, the fluorenyl group may be substituted by one or more substituents. When the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0045] 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.

[0046] 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.

[0047] 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, -CN, 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.

[0048] 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.

[0049] 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.

[0050] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may 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.

[0051] In the present application, D represents deuteration.

[0052] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0053] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0054] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0055] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0056] 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):

[0057]

[0058] 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):

[0059]

[0060] In some embodiments of the present application, the organic compound has a structure shown in the following formula II, formula I-II or I-III:

[0061]

[0062] In some embodiments of the present application, R1 is selected from an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms.

[0063] In some embodiments of the present application, R1 is selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl.

[0064] In some embodiments of the present application, L1 is selected from the group consisting of the following groups:

[0065]

[0066] Optionally, L1 is selected from the group consisting of:

[0067]

[0068] In some embodiments of the present application, Ar1 is selected from the group consisting of the following groups:

[0069]

[0070] In some embodiments of the present application, Ar1 is selected from the group consisting of the following groups:

[0071]

[0072] In some embodiments of the present application, Selected from the group consisting of:

[0073]

[0074] In some embodiments of the present application, Selected from the group consisting of:

[0075]

[0076]

[0077] In some embodiments of the present application, L, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms. For example, L, L2 and L3 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, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0078] Optionally, the substituents in L, L2 and L3 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0079] In some embodiments of the present application, L, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiophenylene, or a substituted or unsubstituted carbazolylene.

[0080] Optionally, the substituents in L, L2 and L3 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0081] Optionally, L and L3 are each independently selected from a single bond or the group consisting of:

[0082]

[0083] Optionally, L and L3 are each independently selected from a single bond or the group consisting of:

[0084]

[0085] Optionally, L2 is selected from the group consisting of:

[0086]

[0087] Optionally, L2 is selected from the group consisting of:

[0088]

[0089] In some embodiments of the present application, Ar2 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar2 is selected from substituted or unsubstituted aryl groups 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 substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0090] Optionally, the substituents in 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.

[0091] Optionally, Ar2 is 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 dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0092] Optionally, the substituents in Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0093] Optionally, Ar2 is selected from the group consisting of:

[0094]

[0095] Further optionally, Ar2 is selected from the group consisting of the following groups:

[0096]

[0097] Optionally, Each is independently selected from the group consisting of:

[0098]

[0099] Optionally, Each is independently selected from the group consisting of:

[0100]

[0101] In some embodiments of the present application, each R is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

[0102] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] 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.

[0111] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.

[0112] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0113] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0114] 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.

[0115] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1 As 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 350 and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute a hole transport layer 320.

[0116] 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 (indium tin oxide) (ITO) as an anode is included.

[0117] 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:

[0118]

[0119]

[0120] In a specific embodiment, the first hole transport layer 321 is HT-5.

[0121] In another specific embodiment, the second hole transport layer 322 is the compound of the present application.

[0122] 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.

[0123] 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 RH-01

[0124] 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,

[0125]

[0126] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is RD-01

[0127] In the present application, the hole blocking layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more hole blocking materials. In a more specific embodiment, the material of the hole blocking layer 340 is HB-01

[0128] Optionally, the electron transport layer 350 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., and 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 350 is composed of ET-21 and LiQ.

[0129]

[0130] 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.

[0131] 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:

[0132]

[0133] In a specific embodiment of the present application, the hole injection layer 310 is PD-01.

[0134] Alternatively, if Figure 1 As shown, an electron injection layer 360 is further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 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 360 includes Yb.

[0135] 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.

[0136] 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 370, an electron transport layer 350 and a cathode 200 which are stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0137] 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.

[0138] In a third aspect, the present application provides an electronic device, comprising the electronic component provided in the second aspect of the present application.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] The compounds whose synthesis methods are not mentioned in this application are raw materials obtained from commercial channels.

[0143] Synthesis example

[0144] 1. Synthesis of IMa1-1

[0145]

[0146] (1) Methyl 2-iodo-4-chlorobenzoate (20.00 g, 67.46 mmol), 2-(4-biphenyl)phenylboronic acid (18.49 g, 67.46 mmol), potassium carbonate (18.65 g, 134.91 mmol), tetrabutylammonium bromide (2.17 g, 6.75 mmol), toluene (120 mL), ethanol (40 mL) and deionized water (40 mL) were added to a three-necked flask and stirred for 15 min under nitrogen protection. Tetrakis(triphenylphosphine)palladium (0.78 g, 0.67 mmol) was added and the temperature was raised to 75°C-80°C and stirred for 25 h. The reaction solution was cooled to room temperature and washed with water several times until neutral and then dried with anhydrous magnesium sulfate. The organic phase was decompressed to remove the solvent and then boiled with ethanol to obtain a white solid IMa1-a1 (18.14 g, yield 67.42%).

[0147]

[0148] (2) IMa1-a1 (18 g, 45.13 mmol) and dry tetrahydrofuran (144 mL) were added to a three-necked flask. Under nitrogen protection, a tetrahydrofuran solution of methylmagnesium chloride (2 mol / L; 45.13 mL, 90.25 mmol) was slowly added dropwise. The system released heat during the addition and the reaction was stirred at room temperature for 12 h. After the reaction was completed, the reaction solution was slowly poured into a 1 mol / L HCl aqueous solution while stirring to quench the reaction, and extracted with dichloromethane. The organic phase was separated and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a colorless oil IM a1-b1 (16.5 g, yield 91.67%).

[0149]

[0150] (3) IMa1-b1 (16.00 g, 40.11 mmol) and dichloroethane (160 mL) were added to a three-necked flask and stirred to dissolve. Under nitrogen protection, methanesulfonic acid (15.42 g, 160.43 mmol) was added dropwise. The system was exothermic and stirred at room temperature for about 8 h. The reaction solution was washed with water several times until neutral and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was passed through a chromatography column (eluent: n-heptane) to obtain an off-white solid IMa1-1 (11.28 g, yield 73.83%).

[0151] IMa1-X listed in Table 1 was synthesized by referring to the method of IMa1-1, except that raw material 1 was used instead of 2-(1-naphthyl)phenylboronic acid in step (1). The main raw materials used, the intermediates synthesized and the yield of the last step are shown in Table 1.

[0152] Table 1

[0153]

[0154]

[0155] 2. Synthesis of IMa2-1:

[0156]

[0157] (1) IMa1-1 (6.00 g, 15.75 mmol), bipyralidin (4.00 g, 15.75 mmol), tris(dibenzylideneacetone)dipalladium (0.14 g, 0.16 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.75 g, 1.58 mmol), potassium acetate (3.10 g, 31.50 mmol) and 1,4-dioxane (60 mL) were added to a three-necked round-bottom flask, heated to 80°C under nitrogen protection, and stirred for 4 h; then cooled to room temperature, the reaction solution was washed with water and dried with magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using a toluene system to obtain solid IMa2-a1 (5.35 g, yield 71.89%).

[0158]

[0159] (2) IMa2-a1 (5.00 g, 10.58 mmol), 4-chlorobromobenzene (2.03 g, 10.58 mmol), potassium carbonate (2.93 g, 21.17 mmol), tetrabutylammonium bromide (0.34 g, 1.06 mmol), toluene (30 mL), ethanol (10 mL) and deionized water (10 mL) were added to a three-necked flask, stirred for 15 min under nitrogen protection, and then tetrakis(triphenylphosphine)palladium (0.12 g, 0.11 mmol) was added and the temperature was raised to 75°C to 80°C and stirred for 6 h; the reaction solution was cooled to room temperature and washed with water several times until neutral, and then dried with anhydrous magnesium sulfate, the organic phase was decompressed to remove the solvent, and then recrystallized with dichloromethane / n-heptane to obtain a white solid IMa2-1 (3.10 g, yield 64.1%).

[0160] Other IMa2-X were synthesized by referring to the synthesis method of IMa2-1, except that raw material 2 was used instead of IMa1-1 in step (1), and raw material 3 was used instead of 4-chlorobromobenzene. The main raw materials used, the synthesized IMa2-X and the yield of the last step are shown in Table 2.

[0161] Table 2

[0162]

[0163]

[0164] Synthesis Example 1: Synthesis of Compound 15

[0165]

[0166] IMa1-a1 (5.00 g, 13.13 mmol), N-[1,1'-biphenyl]-4-yl-3-dibenzofuranamine (4.4 g, 13.13 mmol), tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.11 g, 0.26 mmol) and sodium tert-butoxide (1.89 g, 19.69 mmol) was added to toluene (50 mL), heated to 108 ° C under nitrogen protection, stirred for 3 h, and then cooled to room temperature. The reaction solution was washed with water and separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtering, the filtrate was decompressed to remove the solvent; the crude product was recrystallized and purified using toluene to obtain compound 15 (6.08 g, yield 68.13%) as a white solid; mass spectrum (m / z) = 680.86 [M+H] + .

[0167] NMR data of compound 15: 1 H-NMR (400MHz, CDCl3) δppm7.78-7.74(m,2H),7.52-7.46(m,4H),7.35-7.12(m,16H),7.02(d,1H),6. 99(d,1H),6.96(s,1H),6.95(s,1H),6.76(d,1H),6.61(d,1H),6.52(d,2H),6.48(d,1H),1.45(s,6H).

[0168] The compounds listed in Table 3 were synthesized by referring to the method of compound 15, except that raw material 4 was used instead of IMa1-1, and raw material 5 was used instead of N-[1,1'-biphenyl]-4-yl-3-dibenzofuranamine. The main raw materials used, the synthesized compounds, their yields and mass spectra are shown in Table 3.

[0169] Table 3

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] NMR data of some compounds

[0176] NMR data of compound 97: 1H-NMR(400MHz,CD2Cl2)δppm7.95(s,2H),7.86(d,1H),7.83(d,1H),7.64(s,1H),7.53(d,4H),7.44-7.33(m,7H),7.30-7.22(m,3H) ,7.16-7.12(m,3H),7.09(d,1H),7.03(d,1H),7.01(s,1H),6.83(d,1H),6.71(d,1H),6.69(d,2H),6.59-6.53(m,2H),1.45(s,6H).

[0177] Example of fabrication and evaluation of organic electroluminescent devices

[0178] Embodiment 1:

[0179] The anode was prepared by the following process: The ITO / Ag / ITO substrate is cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and is prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0180] Compound PD-01 was vacuum-deposited on the experimental substrate (anode) to form a layer with a thickness of hole injection layer.

[0181] Compound HT-5 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.

[0182] Compound 15 is vacuum evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer is

[0183] On the second hole transport layer, compound RH-01 and compound RD-01 were co-evaporated at an evaporation rate ratio of 95:5 to form a layer with a thickness of of an organic light-emitting layer.

[0184] Compound HB-01 is vacuum-deposited on the organic light-emitting layer to form a layer with a thickness of Then, on the hole blocking layer, the compound ET-21 and LiQ were mixed at a 1:1 evaporation rate ratio and evaporated to form a layer 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, 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.

[0185] In addition, a compound CP-01 is vacuum-deposited on the cathode to form a layer having a thickness of A cathode protection layer (CPL) is formed to complete the production of the organic electroluminescent device.

[0186] Embodiment 2~embodiment 29:

[0187] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound in Table 5 was used instead of Compound 15 in Example 1 when preparing the second hole transport layer.

[0188] Comparative Example 1 to Comparative Example 3:

[0189] An organic electroluminescent device was prepared in the same manner as in Example 1, except that Compounds A to D in Table 4 were used instead of Compound 15 in Example 1 when preparing the second hole transport layer.

[0190] When preparing the organic electroluminescent device, the structures of the materials used in the comparative examples and the examples are as follows:

[0191] The main material structures used in the above embodiments and comparative examples are shown in Table 4 below:

[0192] Table 4

[0193]

[0194] The performance of the organic electroluminescent devices prepared in Examples 1 to 29 and Comparative Examples 1 to 4 was tested. Specifically, at 10 mA / cm 2 The IVL performance (driving voltage, current efficiency) of the device was tested under the conditions of T95 device life at 15mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 5 below.

[0195] Table 5

[0196]

[0197]

[0198] Referring to Table 5 above, it can be seen that, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the performance of the organic electroluminescent devices of Examples 1 to 29 is greatly improved, with the current efficiency increased by at least 13.6% and the T95 lifespan increased by at least 10.1%.

[0199] It can be seen from the device results in Table 5 above that the lifespan and efficiency of the organic electroluminescent devices of Examples 1 to 29 are significantly improved compared with those of the organic electroluminescent devices of the comparative example. This is mainly because the electron-withdrawing effect of the heteroatom makes the dibenzoheteroaromatic ring more stable than the fluorene ring; at the same time, the lone pair of electrons on the central N atom of the triarylamine is offset toward the heteroaryl plane to form a stable conjugated structure, thereby improving the mobility of the molecule, more effectively improving the transmission efficiency of the compound, and thus improving the service life of the device.

[0200] The embodiments of the compounds using terphenyl and naphthyl-substituted phenyl at the 5-position are more efficient than the embodiments of the compounds using biphenyl at the 5-position. The main reason is that terphenyl and naphthyl-substituted phenyl can better compete with aromatic amine for space on both sides of dimethylfluorene, resulting in a larger twisting angle between molecules, thereby reducing the π-π stacking effect between the molecules of the compound, facilitating the transmission of excitons, obtaining excellent mobility, and further effectively improving the efficiency of the device.

[0201] 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.

[0202] 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 L1 is selected from phenylene, deuterium-substituted phenylene, and phenyl-substituted phenylene; Ar1 is selected from phenyl, deuterium-substituted phenyl, naphthyl, deuterium-substituted naphthyl, biphenyl, deuterium-substituted biphenyl; X is selected from O, S or N(R1); R1 is selected from an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; L, L2 and L3 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, and a substituted or unsubstituted heteroarylene group having 6 to 30 carbon atoms; Ar2 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L, L2, L3 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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; Each R is independently selected from deuterium, a halogen group, a cyano group, 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; n represents the number of R, and n is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when n is greater than 1, any two Rs are the same or different.

2. The organic compound according to claim 1, wherein R1 is selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl.

3. The organic compound according to claim 1, wherein Ar1 is selected from the group consisting of:

4. The organic compound according to claim 1, wherein L, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; Optionally, the substituents in L, L2 and L3 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

5. The organic compound according to claim 1, wherein L, L2 and L3 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; Optionally, the substituents in L, L2 and L3 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

6. The organic compound according to claim 1, wherein Ar2 is 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; Optionally, the substituents in 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.

7. The organic compound according to claim 1, wherein Ar2 is 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 dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

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

9. The organic compound according to claim 1, wherein Each R is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.

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

11. 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 10.

12. The electronic component according to claim 11, wherein The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound; Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device; Optionally, the organic electroluminescent device is a red organic electroluminescent device.

13. An electronic device, characterized in that The electronic device comprises the electronic component according to claim 11 or 12.

Images