Organic compounds, electronic elements, and electronic devices

Abstract

The present application relates to an organic compound, an electronic element, and an electronic device. The organic compound provided by the present application has a structure shown in formula I, and the application of the organic compound to an electronic element can significantly improve the performance of the device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence, and more specifically to an organic compound, electronic component, and electronic device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are considered next-generation display and lighting technologies due to their advantages such as active light emission, high luminous efficiency, low power consumption, light weight, thinness, fast response speed, and wide viewing angle. OLEDs consist of an anode, a hole injection layer, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, and a cathode. Electrons and holes are injected from the cathode and anode, respectively, and then recombine in the organic light-emitting layer through the electron transport layer and hole transport layer to form excitons. These excitons return to the ground state and emit light. The material used for the hole transport layer typically has a low highest occupied molecular orbital (HOMO) value, resulting in a low T1 value. During device operation, excitons generated in the organic light-emitting layer transfer to the hole transport layer, causing charge imbalance within the organic light-emitting layer. This leads to light emission within the hole transport layer or at its interface, ultimately resulting in decreased color purity, reduced efficiency, and shorter lifetime.

[0003] Currently, to improve device efficiency and lifespan, there is an urgent need for luminescent adjustment layer materials with high T1 values ​​and wide bandgap. However, the reported luminescent adjustment layer materials generally have small molecular weights and low glass transition temperatures. During repeated charge-discharge cycles, these materials are prone to crystallization, which disrupts the uniformity of the film and affects its lifespan. Therefore, developing stable and efficient luminescent adjustment layer materials to improve charge mobility, reduce driving voltage, increase device luminous efficiency, and extend device lifespan has significant practical application value. Summary of the Invention

[0004] The purpose of this application is to provide an organic compound, electronic component, and electronic device, wherein using the organic compound in an organic electroluminescent device can improve the performance of the device.

[0005] A first aspect of this application provides an organic compound having the structure shown in Formula I:

[0006]

[0007] Where X is taken from O or S;

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

[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, or 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 with 3 to 20 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, 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 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 aforementioned organic compound.

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

[0014] The organic compound of this application uses dibenzofuran or dibenzothiophene as the parent core, with two substituents in one benzene ring. Both substituents are selected from unsubstituted or deuterated methyl groups, while an aromatic amine group is directly attached to the other benzene ring. The unsubstituted or deuterated methyl group forms a hyperconjugation effect with the attached benzene ring, increasing the electron cloud density of the benzene ring. Furthermore, since the methyl or trideuterated methyl group is relatively small, introducing two groups into the same benzene ring of the aromatic amine in the compound not only finely adjusts the spatial configuration of the molecular structure but also effectively regulates the intermolecular distance, maintaining a certain distance between molecules. This results in higher mobility for the compound and reduces localized crystallization degradation caused by intermolecular stacking after film formation, thus optimizing the film-forming properties of the compound. When the compound of this application is used as a light-emitting adjustment layer in an organic electroluminescent device, it exhibits low voltage, good efficiency, and long lifetime device characteristics. Attached Figure Description

[0015] 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.

[0016] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0017] Figure 2 This is a schematic diagram of a first electronic device according to one embodiment of this application.

[0018] Figure 3This is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0019] Figure 4 This is a schematic diagram of a second electronic device according to one embodiment of this application.

[0020] Explanation of reference numerals in the attached figures

[0021] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0022] 320, Hole transport layer; 321, Luminescence adjustment layer; 330, Organic light-emitting layer; 340, Electron transport layer

[0023] 350, electron injection layer 360, photoelectric conversion layer 400, first electronic device 500, second electronic device Detailed Implementation

[0024] 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 to make this application more comprehensive and complete, and to 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.

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

[0026]

[0027] Where X is taken from O or S;

[0028] R1 and R2 may be the same or different, and each is independently selected from methyl or trideuterated methyl;

[0029] 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, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0030] 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 20 carbon atoms.

[0031] The substituents in L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, 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 with 3 to 20 carbon atoms.

[0032] In this application, It refers to a chemical bond that is attached to other substituents or bonding sites.

[0033] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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.

[0034] 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, haloalkyl, trialkylsilyl, deuteralkyl, aryl, heteroaryl, etc. The number of substituents Rc can be one or more. When two substituents Rc are attached to the same atom, these two substituents Rc can exist independently or be connected to each other to form a ring with the atom; when two adjacent substituents Rc exist on a functional group, the adjacent substituents Rc can exist independently or fuse with the functional group to which they are attached to form a ring.

[0035] 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.

[0036] 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 as 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, fluorene, 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, spirodifluorene, etc., are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, spirodifluorenyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, triphenylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0037] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0038] 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, alkyl, haloalkyl, deuteralkyl, trialkylsilyl, aryl, heteroaryl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-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.

[0039] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing at least one heteroatom, where the heteroatom can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings linked by carbon-carbon bonds, and 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.

[0040] 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.

[0041] 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, alkyl, haloalkyl, deuteralkyl, trialkylsilyl, aryl, and heteroaryl. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl and phenyl-substituted dibenzothiopheneyl. 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.

[0042] In this application, specific examples of aryl groups that are substituents in L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, biphenyl, and naphthyl groups.

[0043] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0044] In this application, specific examples of heteroaryl groups that serve as substituents in L1, L2, Ar1, and Ar2 include, but are not limited to, pyridinyl, pyrimidinyl, carbazoyl, dibenzofuranyl, and dibenzothiopheneyl.

[0045] In this application, the number of carbon atoms in alkyl groups having 1 to 10 carbon atoms 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, 3,7-dimethyloctyl, etc.

[0046] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0047] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0048] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0049] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0050] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0051] 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 linkages that span the bicyclic ring. This means that any possible connection mode is shown in equations (f-1) to (f-10).

[0052]

[0053] For example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0054]

[0055] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0056]

[0057] In some embodiments, the organic compound shown in Formula 1 is selected from the structures shown in Formula 2-1, Formula 2-2, Formula 2-3, Formula 2-4, Formula 2-5, or Formula 2-6:

[0058]

[0059] The definitions of L1, L2, Ar1, and Ar2 are the same as in Equation I.

[0060] In some embodiments, one of R1 and R2 is methyl and the other is trideuterated methyl.

[0061] In the compounds of this application, when one of R1 and R2 is methyl and the other is trideuterated methyl, these two alkyl substituents interact with the aromatic amine nitrogen atom attached to the benzene ring on the other side of the parent nucleus, effectively balancing the overall charge distribution of the molecule. This ensures improved carrier mobility while also giving the compound better chemical stability. When the compounds of this application are used as the light-emitting auxiliary layer of a device, the device's lifespan can be effectively extended.

[0062] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0063] In some embodiments, the substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups with 1 to 5 carbon atoms, deuteralkyl groups with 1 to 5 carbon atoms, trialkylsilyl groups with 3 to 9 carbon atoms, alkyl groups with 1 to 5 carbon atoms, or phenyl groups.

[0064] In some embodiments, 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, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, and substituted or unsubstituted carbazolyl.

[0065] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0066] In some embodiments, 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:

[0067]

[0068] In some embodiments, 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:

[0069]

[0070]

[0071] In some embodiments, 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 20 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 having 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.

[0072] In some embodiments, the substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups with 1 to 5 carbon atoms, deuteralkyl groups with 1 to 5 carbon atoms, trialkylsilyl groups with 3 to 9 carbon atoms, alkyl groups with 1 to 5 carbon atoms, or aryl groups with 6 to 12 carbon atoms.

[0073] In some embodiments, 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 anthracene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoleyl.

[0074] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl or naphthyl.

[0075] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0076]

[0077]

[0078] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the group consisting of:

[0079]

[0080]

[0081]

[0082] In some specific implementations... They may be the same or different, and each is independently selected from the group consisting of the following groups:

[0083]

[0084]

[0085] In some preferred embodiments, Ar1 and Ar2 may be the same or different, and at least one of them is selected from substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted carbazoleyl; optionally, the substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0086] Furthermore, when at least one of Ar1 and Ar2 in the compound of this application is selected from structures including dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, diphenylfluorenyl, spirodifluorenyl, carbazoleyl, and N-phenylcarbazoleyl, the carrier transport capability of the compound can be further improved, which is beneficial to the optimization and improvement of the device luminescence efficiency.

[0087] Specifically, Ar1 and Ar2 may be the same or different, and one of them is independently selected from the group consisting of the following groups:

[0088]

[0089] Another group is selected from the following groups:

[0090]

[0091]

[0092] In some more specific implementations, Selected from the group consisting of the following groups:

[0093]

[0094]

[0095] In some preferred embodiments, the organic compound shown in Formula 1 is selected from the structures shown in Formula 3-1, Formula 3-2, Formula 3-3, Formula 3-4, Formula 3-5, or Formula 3-6:

[0096]

[0097]

[0098] The definitions of X, R1, R2, L1, L2, Ar1, and Ar2 are the same as in Equation I.

[0099] Specifically, the organic compound may be selected from the group consisting of the following compounds:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] 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.

[0110] Optionally, the functional layer includes a light-emitting adjustment layer, which contains the organic compounds of this application.

[0111] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0112] In this application, the organic electroluminescent device may be a blue organic electroluminescent device, a red organic electroluminescent device, or a green organic electroluminescent device.

[0113] Alternatively, the organic electroluminescent device may be a red-light organic electroluminescent device.

[0114] In one embodiment, the electronic component is an organic electroluminescent device, such as... Figure 1 As shown, the organic electroluminescent device may include an anode 100, a hole transport layer 320, a light-emitting adjustment layer 321, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200 stacked together.

[0115] 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.

[0116] 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 otherwise. For example, the material of the hole transport layer may be selected from the group consisting of the following compounds:

[0117]

[0118]

[0119] In one specific embodiment, the hole transport layer 320 is compound HT-1.

[0120] In one specific embodiment, the light-emitting adjustment layer 321 is a compound of this application.

[0121] 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.

[0122] 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 restrictions on this. The host material can be a single host material or a mixture of host materials.

[0123] In one specific embodiment, the main material of the organic light-emitting layer 330 is RH-1.

[0124] 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:

[0125]

[0126]

[0127] In one specific embodiment, the guest material of the organic light-emitting layer 330 is RD-1.

[0128] Optionally, the electron transport layer 350 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 contain metal complexes or / 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-1, and BimiBphen, or anthracene compounds, triazine compounds, or pyrimidine compounds containing heteroazoyl groups as shown below. Specific examples of the nitrogen-containing heterocyclic derivatives used for the electron transport material include, but are not limited to:

[0129]

[0130] In one specific embodiment, the electron transport layer 340 is composed of ET-1 and LiQ.

[0131] 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.

[0132] Optionally, such as Figure 1 As shown, a hole injection layer 310 is further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. 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:

[0133]

[0134] In one specific embodiment, the hole injection layer 310 is composed of HT-1 and PD-1.

[0135] 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 ytterbium (Yb).

[0136] Optionally, the cathode 200 also has a cathode protection layer.

[0137] In one specific embodiment, the cathode protection layer comprises compound CP-1.

[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 IMA-1:

[0148]

[0149] A mixture of 3,4-dimethylphenylboronic acid (30 g, 200 mmol), 2-bromo-6-iodophenol (59.8 g, 200 mmol), tetrakis(triphenylphosphine)palladium (2.3 g, 2 mmol), potassium carbonate (55.2 g, 400 mmol), 180 mL toluene, 90 mL ethanol, and 30 mL water was degassed and purged with nitrogen, then heated at 75 °C for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give IMA-1 (30.5 g, yield: 55%).

[0150] IMA-X in Table 1 was prepared using the same method as IMA-1, except that 3,4-dimethylphenylboronic acid was replaced with raw material 1 and 2-bromo-6-iodophenol was replaced with raw material 2. The main raw materials used, the intermediates synthesized and their yields are listed in Table 1.

[0151] Table 1

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] (2) Synthesis of IM B-1:

[0159]

[0160] A mixture of IMA-1 (30 g, 108 mmol), palladium acetate (2.4 g, 10.8 mmol), 3-nitropyridine (1.3 g, 10.8 mmol), tert-butyl peroxybenzoate (44.1 g, 226.8 mmol), 150 mL hexafluorobenzene, and 100 mL dimethylformamide was degassed and purged with nitrogen. The mixture was heated to 150 °C and reacted for 24 h. After the reaction was complete, the reaction solution was cooled to room temperature. The organic layer was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain IM B-1 (13.4 g, yield: 45%).

[0161] IMA-X in Table 2 was prepared using the same method as IMA-1, except that IMA-X was used instead of IMA-1. The main raw materials used, the intermediates synthesized and their yields are listed in Table 2.

[0162] Table 2

[0163]

[0164]

[0165]

[0166] (3) Synthesis of IM C-1:

[0167]

[0168] IMA-38 (20.9 g, 68 mmol) and 400 mL of acetic acid were added to a 1000 mL three-necked flask, followed by the addition of 74.8 mmol of H2O2 (30 wt% aqueous H2O2 solution, 8.5 g). The mixture was stirred at room temperature for 6 h. Acetic acid was removed by vacuum concentration, and the acetic acid was separated by silica gel chromatography to obtain IM C-1 (13.4 g, yield: 61%).

[0169] IM CX in Table 3 was prepared using the same method as IM C-1, except that IMA-Y was used instead of IMA-38. The main raw materials used, the intermediates synthesized and their yields are listed in Table 3.

[0170] Table 3

[0171]

[0172]

[0173]

[0174]

[0175] (4) Synthesis of IM D-1:

[0176]

[0177] IM C-1 (9.7 g, 30 mmol) was dissolved in 30 mL of dichloromethane, and 30 mmol of trifluoromethanesulfonic acid was slowly added. The mixture was stirred overnight at room temperature. Then, 24 mL of water and 3 mL of pyridine were added, and the mixture was stirred for another 1 h. The reaction was then quenched with water. The mixture was extracted twice with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure and then separated by silica gel chromatography to obtain IM D-1 (5.7 g, yield: 65%).

[0178] IM DX in Table 4 was synthesized using the same method as IM D-1, except that IM CX was used instead of IMC-1. The main raw materials used, the intermediates synthesized and their yields are listed in Table 4.

[0179] Table 4

[0180]

[0181]

[0182]

[0183]

[0184] Synthesis Example 1: Synthesis of Compound 2

[0185]

[0186] IM B-1 (9.94 g, 36.14 mmol), di(4-biphenyl)amine (11.6 g, 36.14 mmol), tris(dibenzylacetone)dipalladium (0.34 g, 0.36 mmol), S-Phos (0.30 g, 0.72 mmol), and sodium tert-butoxide (5.22 g, 54.22 mmol) were added to 80 mL of toluene. The mixture was heated to 108 °C under nitrogen protection and stirred for 2 h. After the reaction was complete, the mixture was cooled to room temperature, washed with water until neutral, dried over magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from a toluene / n-heptane mixture (V / V = 1:3) to give a white solid compound (12.11 g, yield: 65%). Mass spectrometry (m / z) = 516.23 [M+H] + .

[0187] Compound X in Table 5 was prepared using the same method as compound 2, except that IM B-1 was replaced with IM BX or IMD-X, and di(4-biphenyl)amine was replaced with starting material 3. The main starting materials used, the synthesized compounds, their yields, and mass spectra are listed in Table 5.

[0188] Table 5

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200] The NMR data of some compounds are shown in Table 6:

[0201] Table 6

[0202]

[0203] Fabrication and evaluation of organic electroluminescent devices

[0204] Example 1: Red Organic Electroluminescent Device

[0205] The anode is prepared through the following process: [The anode thickness is...] On the ITO / Ag / ITO experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0206] On the anode substrate, compounds HT-1 and PD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0207] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0208] Compound 2 is deposited on the hole transport layer to form a thickness of [thickness value missing]. The light-emitting adjustment layer.

[0209] On the light-emitting adjustment layer, compounds RH-1 and RD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer.

[0210] On the red light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. An electron transport layer is formed; Yb is deposited on the electron transport layer to form a thickness of [missing information]. An electron-injected layer is formed. Magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate of 10%:90% to form a layer with a thickness of [missing information]. The cathode.

[0211] 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.

[0212] Examples 2 to 58:

[0213] Except that, when preparing the light-emitting adjustment layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 7 was used instead of compound 2 in Example 1.

[0214] Comparative Examples 1 to 6:

[0215] Except that, when preparing the light-emitting adjustment layer, compounds A, B, C, D, E, and F were used to replace compound 2 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0216] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0217]

[0218] The organic electroluminescent devices prepared in Examples 1-58 and Comparative Examples 1-6 were subjected to performance tests, specifically at 10 mA / cm². 2 The IVL performance (operating voltage, current efficiency, and color coordinates) of the device was tested under the following conditions. 95 Device lifetime is 20 mA / cm 2 The test was conducted under the specified conditions, and the test results are shown in Table 7 below.

[0219] Table 7

[0220]

[0221]

[0222]

[0223] Referring to Table 7 above, in Examples 1-58, using the compounds of this application as the luminescence adjustment layer material, compared with Comparative Examples 1-6, the voltage was reduced by at least 0.21V, the luminous efficiency was increased by at least 11.8%, and the device lifetime was increased by at least 16.3%. It is evident that using the organic compounds of this application in the luminescence adjustment layer of organic electroluminescent devices can reduce the device voltage and improve the luminous efficiency and lifetime of the organic electroluminescent devices. 95 life.

[0224] Compared with the devices of compounds A and C, the efficiency of the embodiments of this application is significantly improved. This may be because, in compounds A and C, the same benzene ring to which the aromatic amine is attached has an unsubstituted or deuterated methyl substituent, which reduces the rotational degree of freedom of the aromatic amine group, reduces the configurational adjustment ability of the compound, and thus leads to a decrease in charge mobility, thereby resulting in a decrease in the luminous efficiency of the device.

[0225] Compared with the devices of compounds B and D, the embodiments of this application show a significant improvement in luminous efficiency and lifetime. This may be because when fluorene and carbazole are used as the parent nucleus, the molecular LUMO energy level is too shallow and the carrier mobility is too fast. When applied to the luminescence adjustment layer of the device, it will cause a large roll-off, and the charge accumulation will accelerate the device degradation, thereby leading to a decrease in device performance.

[0226] Compared with the device of compound E, the efficiency and lifetime of the embodiments of this application are significantly improved. This may be because there is only one methyl substituent on the dibenzothiophene core of compound E, which has a weaker electron-donating effect and configuration regulation ability. Therefore, the charge mobility and film-forming properties of compound E are inferior to those of the compound of this application.

[0227] Compared with the device based on compound F, the efficiency of the embodiments in this application is significantly improved. This may be because there is a phenylene group between the aromatic amine and the dibenzofuran core in compound F. The presence of the phenylene group changes the overall conjugation range of the molecule, thereby reducing the mobility.

[0228] The preferred embodiments of this application have been described in detail above. 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: Where X is taken from O or S; R1 and R2 may be the same or different, and each is independently selected from methyl or trideuterated methyl; 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, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted carbazolyl. The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl; 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 anthraquinone, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl or naphthyl.

2. 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:

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

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

5. An electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode, characterized in that, The functional layer comprises any one of the organic compounds according to claims 1 to 4.

6. The electronic component according to claim 5, wherein, The functional layer includes a light-emitting adjustment layer; The electronic component is an organic electroluminescent device or a photoelectric conversion device.

7. An electronic device, characterized in that, Includes the electronic components described in claim 5 or 6.

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