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.

Description

Technical Field

[0001] 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

[0002] Organic light-emitting diode (OLED) technology is considered a next-generation display and lighting technology due to its advantages such as active light emission, high luminous efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. An OLED consists of a substrate, an anode, a hole injection layer, a hole transport layer and an electron blocking layer, an organic light-emitting layer, an electron transport layer and a hole blocking layer, an electron injection layer, and a cathode. When a voltage is applied to the anode and cathode, an electric field is generated. Under the influence of this electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes recombine in the organic light-emitting layer to form excitons. These excitons, in an excited state, release energy and return to the ground state, thus causing the organic light-emitting layer to emit light.

[0003] Currently reported organic hole transport materials generally have small molecular weights and low glass transition temperatures. During use, repeated charging and discharging can easily lead to crystallization, disrupting the uniformity of the thin film and thus affecting the material's lifespan. Therefore, developing stable and efficient organic hole transport materials to improve charge mobility, reduce driving voltage, increase device luminous efficiency, and extend device lifespan has significant practical application value.

[0004] While existing technologies disclose materials that can be used in organic electroluminescent devices, it remains necessary to continue developing new materials to further improve the performance of electronic components. Summary of the Invention

[0005] 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.

[0006] A first aspect of this application provides an organic compound having the structure shown in Formula I:

[0007]

[0008] R is selected from alkyl groups having 1 to 10 carbon atoms;

[0009] t is the number of R, which can be selected from 1, 2 or 3. When t is greater than 1, any two R are the same or different.

[0010] Ar3 is selected from aryl groups having 6 to 12 carbon atoms;

[0011] Ar is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;

[0012] The substituents in Ar are each independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, halomethyl groups with 1 to 10 carbon atoms, deuterated methyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, or deuterated aryl groups with 6 to 12 carbon atoms.

[0013] 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.

[0014] 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 with 3 to 30 carbon atoms.

[0015] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 3 to 20 carbon atoms;

[0016] Each R1 and each R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 3 to 12 carbon atoms;

[0017] m is the number of R1s, and m can be selected from 0, 1, 2, 3 or 4. When m is greater than 1, any two R1s are the same or different.

[0018] n is the number of R2s, and n can be selected from 0, 1 or 2. When n is 2, any two R2s are the same or different.

[0019] 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 aforementioned organic compound.

[0020] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0021] This application describes a compound with carbazole as the parent core, with an alkyl-substituted aryl group attached to the carbazole at position 1 and an aromatic amine directly attached to position 3, serving as a hole transport layer material. This structure generates significant steric hindrance, effectively reducing intermolecular forces while largely maintaining the molecular morphology, enhancing the amorphous state of the material, improving its film-forming properties, and resulting in moderate mobility and good lifetime. Furthermore, the alkyl-substituted aryl group at position 1 improves the structural stereochemistry and lateral resistivity, thus enhancing device capacitance and lifetime. Therefore, using this material as a hole transport layer in organic electroluminescent devices can effectively regulate the material's mobility, enhance device efficiency, and maintain device lifetime.

[0022] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0023] 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.

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

[0025] Figure 2 This is a schematic diagram of a first electronic device according to one embodiment of this application.

[0026] Figure 3 This is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0027] Figure 4 This is a schematic diagram of a second electronic device according to one embodiment of this application.

[0028] Explanation of reference numerals in the attached figures

[0029] 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

[0030] 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.

[0031] In a first aspect, this application provides an organic compound having the structure shown in Formula I:

[0032]

[0033] R is selected from alkyl groups having 1 to 10 carbon atoms;

[0034] t is the number of R, which can be selected from 1, 2 or 3. When t is greater than 1, any two R are the same or different.

[0035] Ar3 is selected from aryl groups having 6 to 12 carbon atoms;

[0036] Ar is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms;

[0037] The substituents in Ar are each independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, halomethyl groups with 1 to 10 carbon atoms, deuterated methyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, or deuterated aryl groups with 6 to 12 carbon atoms.

[0038] 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.

[0039] 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 with 3 to 30 carbon atoms.

[0040] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 3 to 20 carbon atoms;

[0041] Each R1 and each R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 3 to 12 carbon atoms;

[0042] m is the number of R1s, and m can be selected from 0, 1, 2, 3 or 4. When m is greater than 1, any two R1s are the same or different.

[0043] n is the number of R2s, and n can be selected from 0, 1 or 2. When n is 2, any two R2s are the same or different.

[0044] In this application, the descriptive phrases "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.

[0045] 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.

[0046] 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.

[0047] 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. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0048] 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, dibenzothiophene-substituted phenyl, pyridine-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.

[0049] 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, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc. In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0050] 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, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, etc. 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.

[0051] 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.

[0052] In this application, the number of carbon atoms in the heteroaryl group used 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 used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0053] 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.

[0054] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0055] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0056] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0057] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0058] 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 connect to any position in the ring system it traverses, and the other end connects 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 through 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.

[0059]

[0060] 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.

[0061]

[0062] In some embodiments of this application, each R1 and each R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl.

[0063] In some embodiments of this application, each R is selected from 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.

[0064] In some embodiments of this application, Ar is selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

[0065] Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, phenyl or deuterated phenyl.

[0066] In some embodiments of this application, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.

[0067] Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, or deuterated phenyl.

[0068] In some embodiments of this application, Ar is selected from the group consisting of:

[0069]

[0070] In some embodiments of this application, Ar is selected from the group consisting of:

[0071]

[0072] In some embodiments of this application, Ar3 is selected from the group consisting of:

[0073]

[0074] In some embodiments of this application, Ar3 is selected from the group consisting of:

[0075]

[0076] In some embodiments of this application, Selected from the group consisting of the following groups:

[0077]

[0078] In some embodiments of this application, Selected from the group consisting of the following groups:

[0079]

[0080] 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 aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. For example, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted aryl groups with 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0081] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, phenyl or deuterated phenyl.

[0082] In some embodiments of this application, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoleyl.

[0083] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, or deuterated phenyl.

[0084] 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:

[0085]

[0086] 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:

[0087]

[0088] 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 having 12 to 24 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, 10, 20, 21, 22, 23, 24, or 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.

[0089] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.

[0090] 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 fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl;

[0091] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, trifluoromethyl, phenyl, deuterated phenyl or naphthyl, and when the number of said substituents is greater than 1, the substituents may be the same or different.

[0092] 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:

[0093]

[0094] 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:

[0095]

[0096] 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:

[0097]

[0098]

[0099] 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:

[0100]

[0101]

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

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114] Secondly, 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 the organic compound of this application.

[0115] Optionally, the functional layer includes a hole transport layer, which contains the organic compound.

[0116] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0117] Optionally, the organic electroluminescent device is a red-light organic electroluminescent device.

[0118] 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 the organic compound of this application.

[0119] In one embodiment, the electronic component is an organic electroluminescent device. For example... 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 340, and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0120] 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.

[0121] 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:

[0122]

[0123]

[0124] In one specific embodiment, the first hole transport layer 321 is HT-20; the second hole transport layer 322 is the compound of this application.

[0125] 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.

[0126] 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 RH.

[0127] 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,

[0128]

[0129] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is RD.

[0130] Optionally, the electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically include metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complex material may be selected from, for example, LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative may 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 heteronitrogenous aryl groups as shown below. In one embodiment of this application, the electron transport layer 340 is composed of ET-18 and LiQ.

[0131]

[0132]

[0133] 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.

[0134] Optionally, such as Figure 1 As shown, 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:

[0135]

[0136] In one specific embodiment of this application, the hole injection layer 310 is PD-1 and HT-20.

[0137] Optionally, such as Figure 1 As shown, 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.

[0138] In another implementation, the electronic component is a photoelectric conversion device. For example... 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 contains the organic compound provided in this application.

[0139] According to a specific implementation method, such as Figure 3 As shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are stacked sequentially. Optionally, the hole transport layer 320 contains the organic compound of this application.

[0140] 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.

[0141] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0142] According to one implementation method, such as Figure 2 As shown, the electronic device is a first electronic device 400, which includes the aforementioned 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, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0143] According to another implementation method, such as Figure 4 As shown, 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 photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0144] 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.

[0145] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0146] Synthesis example

[0147] 1. Synthesis of intermediate Sub-a1:

[0148]

[0149] In a 250 mL three-necked flask, 11.0 g (39.2 mmol) of 4-bromo-2-chloro-9H-carbazole, 11.0 mL (98 mmol) of iodobenzene, 7.5 g (39.4 mmol) of cuprous iodide (CuI), 5.2 mL (43.3 mmol) of trans-1,2-cyclohexanediane, and 16.6 g (17.3 mmol) of potassium phosphate (K3PO4) were dissolved in 100 mL of 1,4-dioxane. The mixture was stirred and heated to reflux under nitrogen protection for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, and the product was extracted with distilled water and dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent and recrystallized from methanol to give compound Sub-a1 (12.0 g, yield 71.5%).

[0150] The intermediate Sub-ax (x is 2 to 9) shown in Table 1 was prepared by referring to the synthesis method of intermediate Sub-al, except that reactant A was used instead of iodobenzene. The main raw materials used, the intermediates synthesized and their yields are shown in Table 1.

[0151] Table 1

[0152]

[0153]

[0154]

[0155] 2. Synthesis of intermediate Sub-b1:

[0156]

[0157] Sub-a1 (12.0 g, 33.65 mmol), 4-tert-butylphenylboronic acid (6.0 g, 33.70 mmol), bis(triphenylphosphine)palladium dichloride (Pd(pph3)2Cl2) (0.24 g, 0.34 mmol), potassium carbonate (K2CO3) (11.6 g, 83.93 mmol), ethylene glycol dimethyl ether (DME) (96 mL), and H2O (24 mL) were added to a three-necked flask. The mixture was stirred and heated to 70 °C under nitrogen protection and reacted for 10 h. The reaction mixture was then cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to obtain Sub-b1 (9 g, yield 65.3%).

[0158] The intermediate Sub-bx (x is 2 to 20) shown in Table 2 was prepared by referring to the synthesis method of intermediate Sub-bl. The difference is that reactant Sub-ax was used instead of Sub-a1, and reactant B was used instead of 4-tert-butylphenylboronic acid. The main raw materials used, the intermediates synthesized and their yields are shown in Table 2.

[0159] Table 2

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] 3. Synthesis of intermediate Sub-c1:

[0166]

[0167] 2-Amino-9,9-dimethylfluorene (12 g, 57.3 mmol), 4-bromobiphenyl (13.4 g, 57.5 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.53 g, 0.58 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.55 g, 1.15 mmol), sodium tert-butoxide (tBuONa) (8.27 g, 86.06 mmol), and toluene (PhMe) (100 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 110 °C with stirring and reacted for 4 h. The reaction mixture was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using toluene, and then purified by recrystallization using toluene / n-heptane to give a white solid Sub-c1 (15 g, yield 72.5%).

[0168] The intermediate Sub-cx (x is 2 to 22) shown in Table 3 was prepared by referring to the synthesis method of intermediate Sub-cl. The difference is that reactant C was used instead of 2-amino-9,9-dimethylfluorene, and reactant D was used instead of 4-bromobiphenyl. The main raw materials used, the intermediates synthesized and their yields are shown in Table 3.

[0169] Table 3

[0170]

[0171]

[0172]

[0173]

[0174] Synthesis Example 1: Synthesis of Compound 7

[0175]

[0176] Sub-b1 (9 g, 21.95 mmol), Sub-c1 (8.3 g, 22.96 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3) (0.2 g, 0.22 mmol), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (S-phos) (0.18 g, 0.43 mmol), sodium tert-butoxide (tBuONa) (3.2 g, 33.30 mmol), and toluene (Ph Me (80 mL) was added to a round-bottom flask under nitrogen protection, and the mixture was heated to 110 °C with stirring and reacted for 3 h. The reaction solution was cooled to room temperature, washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography with toluene, and then purified by recrystallization with toluene / n-heptane to give compound 7 (10 g, yield 62.0%) as a white solid. Mass spectrometry (m / z) = 735.37 [M+H] + .

[0177] The compounds shown in Table 4 were prepared using the same synthetic method as compound 7, except that reactant E was used instead of intermediate Sub-b1 and reactant F was used instead of Sub-c1. The main raw materials used, the synthesized compounds, and their yields are shown in Table 4.

[0178] Table 4

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] NMR data for some intermediates and compounds are shown in Table 5 below:

[0185] Table 5

[0186]

[0187] Example 1: Red Organic Electroluminescent Device

[0188] The device is fabricated through the following process: [The following is a process with thicknesses sequentially defined as follows:] On the ITO / Ag / ITO substrate, surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents were also used to clean the surface of the experimental substrate to remove impurities and oil stains from the ITO substrate surface.

[0189] On the experimental substrate, PD-1 and HT-20 were co-deposited at a deposition rate ratio of 2%:98% to form a thickness of [missing information]. Hole injection layer.

[0190] Compound HT-20 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The first hole transport layer.

[0191] Compound 7 is deposited on the first hole transport layer to form a thickness of Second hole transport layer

[0192] On the second hole transport layer, compounds RH and RD were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0193] On the organic light-emitting layer, compound ET-18 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form a layer with a thickness of [thickness value missing]. The electron transport layer.

[0194] Yb is deposited on the electrotransmission layer to form a thickness of An electron-injected layer was formed; then, magnesium (Mg) and silver (Ag) were co-deposited onto the electron-injected layer at a deposition rate ratio of 1:9 to form a layer with a thickness of [missing information]. The cathode.

[0195] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. The cathode capping layer is used to complete the fabrication of the red organic electroluminescent device.

[0196] Examples 2-24

[0197] Except that when fabricating the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1, with the compounds listed in Table 6 below used instead of compound 6 in Example 1.

[0198] Comparative Examples 1-3

[0199] Except that when fabricating the second hole transport layer, compound A, compound B, and compound C were used instead of compound 7 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0200] The compounds used in preparing the devices of the above embodiments and comparative examples have the following structures:

[0201]

[0202] The performance of the red organic electroluminescent devices prepared in Examples 1-24 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 6:

[0203] Table 6

[0204]

[0205] As can be seen from Table 6 above, when the compound of the present invention is used as the second hole transport layer material of a red organic electroluminescent device, the current efficiency is increased by at least 12.82% and the lifetime is increased by at least 11.54% compared with Comparative Examples 1 to 3.

[0206] 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 I: R is selected from alkyl groups having 1 to 10 carbon atoms; t is the number of R, which can be selected from 1, 2 or 3. When t is greater than 1, any two R are the same or different. Ar3 is selected from aryl groups having 6 to 12 carbon atoms; Ar is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; The substituents in Ar are each independently selected from deuterium, halogen groups, cyano, alkyl groups with 1 to 10 carbon atoms, halomethyl groups with 1 to 10 carbon atoms, deuterated methyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, or deuterated aryl groups with 6 to 12 carbon atoms. 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 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, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 3 to 20 carbon atoms; Each R1 and each R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, trimethylsilyl, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 3 to 12 carbon atoms; m is the number of R1s, and m can be selected from 0, 1, 2, 3 or 4. When m is greater than 1, any two R1s are the same or different. n is the number of R2s, and n can be selected from 0, 1 or 2. When n is 2, any two R2s are either the same or different.

2. The organic compound according to claim 1, wherein, Each R1 and each R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl.

3. The organic compound according to claim 1, wherein, Each R is selected from 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.

4. The organic compound according to claim 1, wherein, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl; Optionally, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, or deuterated phenyl.

5. The organic compound according to claim 1, wherein, Ar3 is selected from the group consisting of the following groups:

6. The organic compound according to claim 1, wherein, Selected from the group consisting of the following groups:

7. 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, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, phenyl or deuterated phenyl.

8. The organic compound according to claim 1, wherein, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl. Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, phenyl, or deuterated phenyl.

9. The organic compound according to claim 1, 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:

10. The organic compound according to claim 1, 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 with 12 to 24 carbon atoms. Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, or deuterated aryl with 6 to 12 carbon atoms.

11. The organic compound according to claim 1, 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 fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, trifluoromethyl, phenyl, deuterated phenyl or naphthyl, and when the number of said substituents is greater than 1, the substituents may be the same or different.

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

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

14. 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 13; Optionally, the functional layer includes a hole transport layer, the hole transport layer containing the organic compound; Further optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

15. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 14.

Images