Organic compound, and electronic element and electronic device using same

Abstract

The present application relates to an organic compound, and an electronic element and an electronic device using same. The organic compound has a structure as represented by formula 1. When the organic compound is applied to an organic electroluminescent device, the performance of the device can be significantly improved.

Description

Organic compounds and electronic components and devices using them

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese patent application No. CN202410798695.6, filed on June 19, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This application relates to the field of organic electroluminescence technology, and more specifically, to an organic compound and electronic components and devices using the same. Background Technology

[0004] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists 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.

[0005] Taking organic light-emitting diodes (OLEDs) as an example, they generally include an anode, a hole transport layer, an organic light-emitting layer (OLED) serving as an energy conversion layer, an electron transport layer, and a cathode, stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side move towards the OLED, and holes on the anode side also move towards the OLED. Electrons and holes combine in the OLED to form excitons, which release energy in an excited state, thus causing the OLED to emit light. Although existing technologies disclose materials that can be used in organic light-emitting diodes, it is still necessary to continue developing new materials to further improve the performance of electronic components. Summary of the Invention

[0006] The purpose of this application is to provide an organic compound and electronic components and devices using the same, wherein using the organic compound in an organic electroluminescent device can improve the device's performance.

[0007] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0008] R1 and R2 may be the same or different, and each is independently selected from methyl or phenyl;

[0009] L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0010] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S with 3 to 30 carbon atoms.

[0011] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups containing O or S with 3 to 20 carbon atoms.

[0012] A second aspect of this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic compound described in the first aspect of this application.

[0013] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0014] The compound presented in this application is formed with a 2-fluorenyl-1-phenylnaphthalene core and a triarylamine attached to the phenyl group of the core. On one hand, the fluorenyl group at position 2 and the aromatic amine at position 1 form a spherical stereostructure, regulating the molecular configuration and providing steric hindrance to the overall molecular structure, preventing intermolecular stacking and resulting in better film-forming properties, thus improving lifetime. On the other hand, the strong conjugation effect between the core and the triarylamine via phenyl bonding enhances the local electron cloud density, allowing the material to maintain high hole mobility while possessing deep HOMO energy levels, thereby improving the hole transport capability and ultimately enhancing the luminous efficiency of the device. Using this material as the hole transport layer in organic electroluminescent devices can effectively enhance device efficiency and extend device lifetime.

[0015] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0016] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0017] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0018] Figure 2 is a schematic diagram of a first electronic device according to one embodiment of this application.

[0019] Figure 3 is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0020] Figure 4 is a schematic diagram of a second electronic device according to one embodiment of this application.

[0021] Explanation of reference numerals in the attached figures: 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 Implementation

[0022] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0023] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0024] R1 and R2 may be the same or different, and each is independently selected from methyl or phenyl;

[0025] L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0026] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S with 3 to 30 carbon atoms.

[0027] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups containing O or S with 3 to 20 carbon atoms.

[0028] In this application, the descriptive terms "each independently selected from" and "separately independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. 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. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0029] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, halogen groups, cyano, alkyl, trialkylsilyl, haloalkyl, cycloalkyl, aryl, heteroaryl, etc.

[0030] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0031] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in this application, biphenyl, terphenyl, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthraceneyl, etc. In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0032] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiopheneyl-substituted phenyl, pyridyl-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0033] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom. The heteroatom can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner. Any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolel, benzothiopheneyl, dibenzothiopheneyl, thiophenothiopheneyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiazinyl, silfluorenyl, dibenzofuranyl, etc. In this application, the heteroaryl group refers to a divalent group formed by the further loss of a hydrogen atom from a heteroaryl group. In this application, a heteroaryl group containing O or S refers to a monovalent aromatic ring or its derivative containing at least one O or S atom, such as benzofuranyl, benzothiophenyl, dibenzofuranyl or dibenzothiophenyl.

[0034] In this application, the substituted heteroaryl group can be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups containing O or S, trialkylsilyl groups, alkyl groups, haloalkyl groups, deuteryl groups, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl groups and phenyl-substituted dibenzothiophenyl groups. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0035] In this application, the aryl group used as a substituent can have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, naphthyl, and anthraceneyl groups. base.

[0036] In this application, the number of carbon atoms in the O- or S-containing heteroaryl group that serves 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, or 20. Specific examples of heteroaryl groups that serve as substituents include, but are not limited to, benzofuranyl, benzothiophenyl, dibenzofuranyl, and dibenzothiophenyl.

[0037] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups 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, and 3,7-dimethyloctyl.

[0038] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0039] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0040] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0041] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0042] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can be connected to any position in the ring system it traverses, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule via two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0043] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0044] In some embodiments of this application, the organic compound has the structure shown in Formulas I-1 to I-36:

[0045] The definitions of L1, L2, Ar1, and Ar2 in Equations I-1 to I-36 are the same as those in Equation 1.

[0046] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with a single bond and 6 to 18 carbon atoms. For example, L1 and L2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with a single bond and 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0047] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, or phenyl.

[0048] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0049] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0050] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0051] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0052] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S having 12 to 18 carbon atoms. For example, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0053] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl containing O or S with 5 to 12 carbon atoms.

[0054] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted triphenylene.

[0055] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

[0056] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted groups V; wherein the unsubstituted group V is selected from the group consisting of:

[0057] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0058] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0059] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0060] In some embodiments of this application, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0061] In some embodiments of this application, They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0062] Specifically, the organic compounds in this application are selected from the group consisting of the following compounds:

[0063] In a second aspect, this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains an organic compound of the first aspect of this application.

[0064] Optionally, the functional layer includes a hole transport layer, which contains the organic compound.

[0065] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0066] Optionally, the organic electroluminescent device is a red-light organic electroluminescent device.

[0067] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is closer to the anode than the second hole transport layer, and the second hole transport layer contains an organic compound of the first aspect of this application.

[0068] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1, the organic electroluminescent device may include an 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 stacked together. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0069] Optionally, the anode 100 comprises an anode material, preferably one with a high work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0070] Optionally, the hole transport layer includes one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not specify any particular type of material. For example, the material of the first hole transport layer may be selected from the group consisting of the following compounds:

[0071] In one specific embodiment, the first hole transport layer 321 is HT-1; the second hole transport layer 322 is an organic compound of this application.

[0072] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or it 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. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. 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.

[0073] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials; this application does not impose any special limitations on this. The host material can be a single host material or a mixture of host materials. In one embodiment of this application, the host material of the organic light-emitting layer 330 is a compound. and compounds

[0074] The guest material of the organic light-emitting layer 330 can be selected with reference to existing technologies, such as iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0075] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is...

[0076] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material can be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered or five-membered ring skeleton, a fused aromatic ring compound with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, 1,10-phenanthroline compounds such as Bphen, NBphen, ET-20, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazo aryl groups as shown below.

[0077] In one embodiment of this application, the electron transport layer 340 is composed of ET-20 and LiQ.

[0078] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection 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 alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Preferably, a metal electrode comprising magnesium and silver is included as the cathode.

[0079] Optionally, as shown in Figure 1, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0080] In one specific embodiment of this application, the hole injection layer 310 is HT-1 and P-dopant.

[0081] Optionally, as shown in Figure 1, an electron injection layer 350 is further disposed 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 complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes Yb.

[0082] In another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG3, 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 contains the organic compound provided in this application.

[0083] According to one specific embodiment, as shown in FIG3, 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 stacked sequentially. Optionally, the hole transport layer 320 comprises the organic compound of this application.

[0084] Optionally, the photoelectric conversion device can be a solar cell, especially an organic thin-film solar cell. For example, in one embodiment of this application, the solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked sequentially, wherein the hole transport layer contains the organic compound of this application.

[0085] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0086] According to one embodiment, as shown in FIG2, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0087] In another embodiment, as shown in FIG4, the electronic device is a second electronic device 500, which includes the aforementioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a photosensor, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0088] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0089] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0090] Synthesis example

[0091] 1. Synthesis of intermediate IM A-1:

[0092] Nitrogen gas (0.100 L / min) was bubbled into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, the following raw materials were added sequentially: 2-bromo-9-methyl-9-phenyl-9H-fluorene (100.00 g, 298.29 mmol), pinacol diborate (114.97 g, 447.44 mmol), tris(dibenzylacetone)dipalladium (2.73 g, 2.98 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (2.84 g, 14.64 mmol), and potassium acetate (64.31 g, 656.25 mmol). Isopropyl acetate (800 mL) was added as a solvent. The stirring was started, and the temperature was raised to 89 °C for 12 h. After the reaction was completed, the mixture was cooled to room temperature. The reaction solution was washed with water, extracted with dichloromethane, and the organic phase was separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain intermediate IMA-1 (58.16 g, yield 51%).

[0093] The intermediates IM AX (X is 2 to 4) listed in Table 1 were synthesized using the same method as intermediate IMA-1, except that reactant a was used instead of 2-bromo-9-methyl-9-phenyl-9H-fluorene. The main raw materials used, the structures of the synthesized intermediates and their yields are shown in Table 1.

[0094] Table 1

[0095] 2. Synthesis of intermediate IM B-1:

[0096] Nitrogen gas (0.100 L / min) was bubbled through a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, the following raw materials were added sequentially: 1-bromo-2-iodonaphthalene (100 g, 300.3 mmol), 9,9-dimethylfluorene-2-boronic acid (71.51 g, 300.3 mmol), bis(triphenyl)palladium dichloride (Pd(PPh3)2Cl2) (1.05 g, 1.50 mmol), and potassium carbonate (103.77 g, 750.84 mmol). A mixed solvent of ethylene glycol dimethyl ether (DME) (800 mL) and water (200 mL) was added. Stirring was started, and the temperature was raised to 70-75 °C for 12 h. After the reaction was complete, the mixture was cooled to room temperature. The reaction solution was washed with water, extracted with dichloromethane, and the organic phase was separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate, IM B-1 (65.96 g, yield 55%).

[0097] The intermediates IM BX (X is 2 to 8) listed in Table 2 were synthesized using the same method as intermediate IM B-1, except that reactant b was used instead of 9,9-dimethylfluorene-2-boronic acid. The main raw materials used, the structure of the synthesized intermediates and their yields are shown in Table 2.

[0098] Table 2

[0099] 3. Synthesis of intermediate IM B-9

[0100] Nitrogen gas (0.100 L / min) was bubbled into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, the following raw materials were added sequentially: 1-bromo-2-iodonaphthalene (100 g, 300.3 mmol), IMA-2 (126.3 g, 330.4 mmol), bis(triphenyl)palladium dichloride (Pd(PPh3)2Cl2) (0.42 g, 3.0 mmol), and potassium carbonate (526.99 g, 750.82 mmol). A mixed solvent of toluene (800 mL), ethanol (400 mL), and water (200 mL) was added. The stirring was started, and the temperature was raised to 75 °C for 15 h. After the reaction was complete, the mixture was cooled to room temperature. The reaction solution was washed with water, extracted with dichloromethane, and the organic phase was separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation of the filtrate. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid intermediate, IM B-9 (65.12 gg, yield 47%).

[0101] The intermediates IM BX (X is 10 to 12) listed in Table 3 were synthesized using the same method as intermediate IM B-9, except that reactant c was used instead of IM A-2. The main raw materials used, the structure of the synthesized intermediates and their yields are shown in Table 3.

[0102] Table 3

[0103] 4. Synthesis of intermediate IM C-1:

[0104] Nitrogen gas (0.100 L / min) was bubbled through a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, IM B-1 (65 g, 162.77 mmol), 4-chloroboric acid (25.45 g, 162.77 mmol), bis(triphenyl)palladium dichloride (Pd(PPh3)2Cl2, 0.57 g, 0.81 mmol), and potassium carbonate (56.24 g, 406.93 mmol) were added sequentially, along with a mixed solvent of toluene (520 mL) and water (130 mL). The stirring was started, and the temperature was raised to 75–78 °C for 8 h. After the reaction was complete, the mixture was cooled to room temperature. After washing the reaction solution with water, the organic phase was separated and dried with anhydrous magnesium sulfate. After filtration, the filtrate was distilled under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using n-heptane. The crude product was then purified by recrystallization using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate IM C-1 (45.59 g, yield 65%).

[0105] The intermediates listed in Table 4, IM CX (X is 2 to 36), were synthesized using the same method as intermediate IM C-1, except that IM BX was used instead of IM B-1 and reactant d was used instead of 4-chlorophenylboronic acid. The main raw materials used, the structures of the synthesized intermediates and their yields are shown in Table 4.

[0106] Table 4

[0107] Synthesis Example 1. Synthesis of Compound 36

[0108] (1) Synthesis of intermediate IM 36-1

[0109] Nitrogen gas (0.200 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser for 15 min to purge the flask. Then, intermediate IM C-1 (20.00 g, 46.41 mmol), 4-aminobiphenyl (7.85 g, 46.41 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3) (0.42 g, 0.46 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos) (0.44 g, 0.93 mmol), sodium tert-butoxide (6.69 g, 69.61 mmol), and toluene (160 mL) were added sequentially. The mixture was refluxed at 105 to 110 °C for 4 h. After the reaction was completed, the mixture was cooled to room temperature. After washing the organic phase with water, anhydrous magnesium sulfate was added to dry the organic phase. After filtration, 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, and then purified by recrystallization using a toluene / n-heptane solvent system to obtain a white solid product IM 36-1 (19.1 g, yield 73%).

[0110] (2) Synthesis of compound 36

[0111] Nitrogen gas (0.100 L / min) was introduced into a three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser to purge the flask for 15 min. Then, IM 36-1 (10.00 g, 17.74 mmol), 4-bromobiphenyl (4.14 g, 17.74 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.16 g, 0.18 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (S-Phos, 0.15 g, 0.35 mmol), sodium tert-butoxide (2.56 g, 26.61 mmol), and toluene (80 mL) were added sequentially. The mixture was refluxed at 105-110 °C for 6 h. After the reaction was completed, the mixture was cooled to room temperature. After washing the organic phase with water, the mixture was separated, and anhydrous magnesium sulfate was added to dry the organic phase. The filtrate was filtered, and the solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system, followed by recrystallization using a toluene / n-heptane solvent system to give a white solid compound 36 (6.48 g, yield 51%). Mass spectrometry (m / z) = 716.32 [M+H] + .

[0112] The compounds listed in Table 5 were synthesized using the same method as compound 36, with the following differences: intermediate IM CX was used instead of intermediate IM C-1, reactant e was used instead of 4-aminobiphenyl, and reactant f was used instead of 4-bromobiphenyl. The main raw materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 5.

[0113] Table 5

[0114] NMR data for some compounds are shown in Table 5.

[0115] Table 5

[0116] Example 1: Red Organic Electroluminescent Device

[0117] Anodizing pretreatment is performed through the following process: The thickness is sequentially... The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (height). Surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode. The surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0118] On the aforementioned experimental substrate, compounds HT-1 and P-dopant were co-deposited at a deposition rate ratio of 97%:3% to form a thickness of [missing information]. Hole injection layer.

[0119] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The first hole transport layer.

[0120] Compound 36 is deposited on the first hole transport layer to form a thickness of The second hole transport layer.

[0121] On the second hole transport layer, compounds P, N, and R-dopant were co-deposited at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0122] On the organic light-emitting layer, compound ET-20 and LiQ were co-deposited at a 50%:50% evaporation rate ratio to form a layer with a thickness of [missing information]. The electron transport layer.

[0123] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed; then, magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate ratio of 10%:90% to form a layer with a thickness of [missing information]. The cathode.

[0124] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The cathode capping layer is then used to complete the fabrication of the red organic electroluminescent device.

[0125] Examples 2 to 37:

[0126] The organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 6 was used instead of compound 36 in Example 1 when preparing the second hole transport layer.

[0127] Comparative Examples 1 to 3:

[0128] Except that compounds A, B, C, and D were used to replace compound 36 in Example 1 when preparing the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1.

[0129] The structures of the compounds used in preparing the devices of the above embodiments and comparative examples are listed below:

[0130] The performance of the green organic electroluminescent devices prepared in Examples 1-37 and Comparative Examples 1-6 was tested, specifically at 15 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 Test T under the conditions 95 Device lifespan, test results are shown in Table 6 below.

[0131] Table 6

[0132] Referring to Table 6 above, it can be seen that when the compound of this application is used as the second hole transport layer of a red organic light-emitting device, the device performance can be significantly improved. Specifically, compared with the organic light-emitting devices of Comparative Examples 1-4, the current efficiency of the organic light-emitting devices of Examples 1-37 using the compound of this application as the second hole transport layer is improved by at least 10.81%. 95 Lifespan increased by at least 15.06%.

[0133] The preferred embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: R1 and R2 may be the same or different, and each is independently selected from methyl or phenyl; L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S with 3 to 30 carbon atoms. The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, deuteralkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups containing O or S with 3 to 20 carbon atoms.

2. The organic compound according to claim 1, wherein, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms; Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, or phenyl.

3. The organic compound according to claim 1 or 2, wherein, L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

4. The organic compound according to any one of claims 1 to 3, wherein, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

5. The organic compound according to any one of claims 1 to 4, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups containing O or S with 12 to 18 carbon atoms. Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, or heteroaryl containing O or S with 5 to 12 carbon atoms.

6. The organic compound according to any one of claims 1 to 5, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triphenylene; Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.

7. The organic compound according to any one of claims 1 to 6, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of the following groups:

8. The organic compound according to any one of claims 1 to 7, wherein, They may be the same or different, and each is independently selected from the group consisting of the following groups:

9. The organic compound according to any one of claims 1 to 8, wherein, The organic compound is selected from the group consisting of the following compounds:

10. An electronic component, characterized in that, The electronic component includes 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 an organic compound as described in any one of claims 1 to 9.

11. The electronic component according to claim 10, wherein, The functional layer includes a hole transport layer, and the hole transport layer contains 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-light organic electroluminescent device.

12. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 10 or 11.

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