Organic compound, and electronic component and electronic device using same

Abstract

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

Description

Organic compounds and electronic components and devices using them

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese patent application No. CN202411204905.0, filed on August 29, 2024, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] Organic light-emitting diodes (OLEDs) are devices fabricated by depositing a layer of organic material between two metal electrodes through spin coating or vacuum evaporation. The structure and light-emitting principle of OLEDs are quite simple. A monochrome OLED device has an anode and a cathode at both ends, with several stacked layers of organic functional material sandwiched in between, forming the organic light-emitting layer. By applying current to both ends of the device, the organic light-emitting layer emits light; different materials emit different colors: white light is generally needed for illumination, while red, green, and blue light are typically required for displays. This device is self-emissive, requiring no additional backlight or excitation light, giving it unique advantages in both display and lighting applications. After more than a decade of rapid development, OLEDs have already established a significant market presence and continue to grow rapidly, considered by the industry as the fourth generation of display technology after LCD.

[0005] The most significant challenges in existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. With the increasing size of displays, the driving voltage also rises. Research on improving the performance of OLEDs includes reducing the driving voltage, increasing luminous efficiency, and extending lifespan. To enhance OLED performance, the device structure design incorporates multiple organic functional layers in addition to the traditional anode, cathode, and luminescent layer, forming a complete device. To further improve efficiency and lifespan and balance hole injection and transport, a light-adjusting layer is added between the organic luminescent layer and the hole transport layer. This layer typically exhibits high hole mobility and low ionization potential, making it a crucial component of organic light-emitting diodes. Continued research and development of new light-adjusting layer materials are necessary to further improve the performance of organic light-emitting diodes. Summary of the Invention

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

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

[0008] Where X is selected from C(R1R2), N(R3), O or S;

[0009] R1, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring.

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

[0011] 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 heteroaryl groups with 3 to 30 carbon atoms;

[0012] Ar1 is selected from substituted or unsubstituted aryl groups with 10 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0013] The substituents in L1, L2, and Ar1 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, trialkylsilyl with 3 to 12 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterylaryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0014] Each R is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms.

[0015] The substituents in R may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.

[0016] m is the number of R, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R are the same or different; or any two adjacent R form a saturated or unsaturated 3 to 15-membered ring.

[0017] A second aspect of this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the organic compound described in the first aspect.

[0018] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0019] The compound designed in this application contains a 2,5-disubstituted phenylarylamine as its core structure. The key feature of this structure is the attachment of an aromatic ring substituent to the ortho position of the arylamine group on the benzene ring. This structure effectively enhances the molecular spatial distortion, resulting in an asymmetric molecule that improves film formation properties during vapor deposition, enhances the thickness uniformity of organic functional films, and thus significantly improves device lifetime. Simultaneously, an ortho-biphenyl group is attached to the meta position (para position of the aryl substituent) of the arylamine group. This distorted terphenyl structure links the power-conducting biphenyl group to the arylamine group via the meta position, minimizing the overlap area between the HOMO and LUMO orbitals of the smaller molecule, thereby increasing the molecular energy density (E). g The energy levels and T1 energy level can be improved, thereby increasing the luminous efficiency and further improving the lifetime. In addition, the selection of a dibenzo-pentacyclic planar structure with high carrier mobility can improve the electron blocking effect of the device and improve the luminous efficiency of the device.

[0020] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0021] 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.

[0022] Figure 1 is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0023] Figure 2 is a schematic diagram of a first electronic device according to one embodiment of this application.

[0024] Figure 3 is a schematic diagram of the structure of a photoelectric conversion device according to one embodiment of this application.

[0025] Figure 4 is a schematic diagram of a second electronic device according to one embodiment of this application.

[0026] Explanation of reference numerals in the attached figures: 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. Detailed Implementation

[0027] 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.

[0028] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0029] Where X is selected from C(R1R2), N(R3), O or S;

[0030] R1, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring.

[0031] Ar is selected from aryl groups having 6 to 12 carbon atoms;

[0032] 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 heteroaryl groups with 3 to 30 carbon atoms;

[0033] Ar1 is selected from substituted or unsubstituted aryl groups with 10 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0034] The substituents in L1, L2, and Ar1 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, trialkylsilyl with 3 to 12 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterylaryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms;

[0035] Each R is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms.

[0036] The substituents in R may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms.

[0037] m is the number of R, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R are the same or different; or any two adjacent R form a saturated or unsaturated 3 to 15-membered ring.

[0038] "Any two adjacent substituents" can include two substituents on the same atom, or one substituent on each of two adjacent atoms; wherein, when two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to; when one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring.

[0039] 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.

[0040] 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 substituent, i.e., Rc, can be, for example, deuterium, halogen group, cyano, alkyl, trialkylsilyl, haloalkyl, deuterated alkyl, cycloalkyl, aryl, deuterated aryl, heteroaryl, etc.

[0041] 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.

[0042] 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.

[0043] In this application, terphenyl includes

[0044] 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.

[0045] In this application, the substituted aryl group can be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen groups, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteralkyl, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiopheneyl-substituted phenyl, pyridyl-substituted phenyl, etc. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituents is 18.

[0046] 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 linked by carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused 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.

[0047] 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.

[0048] In this application, the number of carbon atoms in the aryl group used as a substituent can be 6 to 12, for example, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, or 12. Specific examples of aryl groups used as substituents include, but are not limited to, phenyl, biphenyl, and naphthyl.

[0049] In this application, the number of carbon atoms in the heteroaryl group used as a substituent can be 3 to 12, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. Specific examples of heteroaryl groups used as substituents include, but are not limited to, pyridinyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolinyl, quinazolinyl, quinoxalinyl, and isoquinolinyl.

[0050] 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.

[0051] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0052] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0053] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0054] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0055] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This indicates that one end of the linker can be connected to any position in the ring system it traverses, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule via two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0056] 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.

[0057] In some embodiments of this application, the organic compounds are selected from the structures shown in Formula I-1, Formula I-2, Formula I-3, Formula I-4, Formula I-5, or Formula I-6:

[0058] In equations I-1 to I-6, L1, L2, Ar, R, and m are as defined in equation 1.

[0059] In some embodiments of this application, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl; or any two Rs form a benzene ring, naphthyl ring or phenanthrene ring.

[0060] In some embodiments of this application, R1, R2, and R3 may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl; or R1 and R2 form a fluorene ring.

[0061] In some embodiments of this application, Ar1 is selected from substituted or unsubstituted aryl groups having 10 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, Ar1 is selected from substituted or unsubstituted aryl groups having 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18 carbon atoms.

[0062] Optionally, the substituents in Ar1 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterylalkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterylaryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

[0063] In some embodiments of this application, Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl.

[0064] Optionally, the substituents in Ar1 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

[0065] In some embodiments of this application, Ar1 is selected from the group consisting of:

[0066] In some embodiments of this application, Ar1 is selected from the group consisting of:

[0067] In some embodiments of this application, Ar is selected from the group consisting of:

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

[0069] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with a single bond and 6 to 18 carbon atoms. For example, L1 and L2 are each independently selected from substituted or unsubstituted aryl groups with a single bond and 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0070] 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, alkyl, phenyl or deuterated phenyl with 1 to 5 carbon atoms.

[0071] In some embodiments of this application, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0072] 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, phenyl or deuterated phenyl.

[0073] 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:

[0074] 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:

[0075] In some embodiments of this application, Selected from the group consisting of the following groups:

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

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

[0078] In a second aspect, this application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains an organic compound of the first aspect of this application.

[0079] Optionally, the functional layer includes a hole transport layer, which contains the organic compound.

[0080] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0081] Optionally, the organic electroluminescent device is a red-light organic electroluminescent device.

[0082] 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.

[0083] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, an electron transport layer 350, and a cathode 200 stacked together. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0084] 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.

[0085] 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:

[0086] In one specific implementation, the first hole transport layer 321 is HT-1.

[0087] In another specific embodiment, the second hole transport layer 322 is an organic compound of this application.

[0088] Optionally, the second hole transport layer 322 may also be referred to as a hole adjustment layer, electron blocking layer, hole auxiliary layer, hole buffer layer, light emission auxiliary layer, or light emission adjustment layer.

[0089] 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.

[0090] 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 p-RH. and n-RH

[0091] 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,

[0092] In one embodiment of this application, the guest material of the organic light-emitting layer 330 is RD.

[0093] In this application, the hole blocking layer 340 can be a single-layer structure or a multi-layer structure, and it can include one or more hole blocking materials. In a more specific embodiment, the material of the hole blocking layer 340 is HB-1.

[0094] 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 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 350 is composed of ET-20 and LiQ.

[0095] 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.

[0096] Optionally, as shown in Figure 1, a hole injection layer 310 is further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. For example, the compounds contained in the hole injection layer 310 are selected from the group consisting of the following compounds:

[0097] In one specific embodiment of this application, the hole injection layer 310 is HT-1 and NDP.

[0098] Optionally, as shown in Figure 1, an electron injection layer 360 is further disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 360 includes Yb.

[0099] In another embodiment, the electronic component is a photoelectric conversion device. As shown in FIG3, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in this application.

[0100] According to one specific embodiment, as shown in FIG3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 370, an electron transport layer 350, and a cathode 200 stacked sequentially. Optionally, the hole transport layer 320 comprises the organic compound of this application.

[0101] 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.

[0102] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0103] According to one embodiment, as shown in FIG2, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0104] In another embodiment, as shown in FIG4, the electronic device is a second electronic device 500, which includes the aforementioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a photosensor, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0105] The following examples illustrate the synthesis methods of the organic compounds in this application, but this application is not limited in any way.

[0106] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0107] Synthesis example

[0108] 1. Synthesis of intermediate IM a1-1

[0109] (1) 4-bromo-3-chloroiodobenzene (20.00 g, 63.03 mmol), 2-biphenylboronic acid (12.48 g, 63.03 mmol), potassium carbonate (17.42 g, 126.06 mmol), toluene (100 mL), ethanol (60 mL) and water (40 mL) were added to a three-necked flask and stirred for 15 min under nitrogen protection. Bis(triphenylphosphine)palladium dichloride (0.44 g, 0.63 mmol) was added and the temperature was raised to 75 to 80 °C and stirred for 5 h. After cooling the reaction solution to room temperature, it was washed with water several times until neutral and then dried with anhydrous magnesium sulfate. The organic phase was depressurized to remove the solvent and then washed with ethanol to obtain a white solid IM a1-a (14.50 g, yield 66.95%).

[0110] (2) The intermediate IM a1-a (10.00 g, 29.10 mmol), phenylboronic acid (3.55 g, 67.46 mmol), potassium carbonate (8.04 g, 58.21 mmol), toluene (50 mL), ethanol (30 mL) and water (20 mL) were added to a three-necked flask and stirred for 15 min under nitrogen protection. Bis(triphenylphosphine)palladium dichloride (0.20 g, 0.29 mmol) was added and the temperature was raised to 75 to 80 °C and stirred for 6 h. After cooling the reaction solution to room temperature, it was washed with water several times until neutral and then dried with anhydrous magnesium sulfate. The organic phase was depressurized to remove the solvent and then washed with ethanol to obtain a white solid IM a1-1 (7.10 g, yield 71.56%).

[0111] Other IM a1-X listed in Table 1 were synthesized using the same method as IM a1-1. The difference is that raw material 1 was used instead of phenylboronic acid in step (2) above. The main raw materials used, the synthesis of IM a1-X, and the yield of the last step are shown in Table 1.

[0112] Table 1

[0113] Synthesis Example 1: Synthesis of Compound 5

[0114] The following substances were added: IM a1-1 (6.00 g, 17.60 mmol), N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluorene-3-amine (6.36 g, 17.60 mmol), sodium tert-butoxide (2.54 g, 26.40 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.14 g, 0.35 mmol), and tris(dibenzylideneacetone)dipalladium (0.16 g, ... 0.18 mmol) was added to toluene (60 mL), heated to 108 °C under nitrogen protection, stirred for 3 h, and then cooled to room temperature. The reaction solution was washed with water and separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from toluene to give compound 5 (7.60 g, yield 64.85%) as a white solid. Mass spectrometry (m / z) = 666.3 [M+H] + .

[0115] The compounds listed in Table 2 were synthesized using the same method as compound 5, except that starting material 2 was used instead of IM a1-X and starting material 3 was used instead of N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluorene-3-amine. The main starting materials used, the synthesized compounds, their yields, and mass spectrometry results are shown in Table 2.

[0116] Table 2

[0117] NMR data of compound 5

[0118] 1 H-NMR (400MHz, CDCl3): 7.62(d,1H),7.45-6.90(m,27H),6.82(s,1H),6.77(s,1H),6.38(d,1H),6.21(d,2H),1.27(s,6H).

[0119] NMR data of compound 167

[0120] 1 H-NMR (400MHz, CDCl3):7.55(d,1H),7.48(d,2H),7.44-7.28(m,12H),7.28-6.76(m,19H),6.56(s,1H),6.16(d,2H),1.27(s,6H).

[0121] NMR data of compound 229

[0122] 1 H-NMR(400MHz, CDCl3):7.63(s,1H),7.59(d,1H),7.25-7.17(m,27H),7.05-6 .80(m,7H),6.75(s,1H),6.56(s,2H),6.32(s,1H),6.25(d,1H),1.28(s,6H).

[0123] Example 1: Red Organic Electroluminescent Device

[0124] First, perform anodizing pretreatment through the following process: The thickness is sequentially... The ITO / Ag / ITO substrate was cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (height). Surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode. The surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0125] On the aforementioned substrate, compound HT-1 and NDP were co-deposited at a deposition rate ratio of 97%:3% to form a layer with a thickness of [missing information]. Hole injection layer.

[0126] Compound HT-1 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The first hole transport layer.

[0127] Compound 5 is deposited on the first hole transport layer to form a thickness of The second hole transport layer.

[0128] On the second hole transport layer, compounds p-RH, n-RH, and RD were co-deposited at a deposition rate ratio of 63%:37%:2% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0129] Compound HB-1 was deposited on the organic light-emitting layer to form a thickness of [missing information]. Hole-blocking layer.

[0130] Compound ET-20 and LiQ were co-deposited on the hole-blocking layer at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. The electron transport layer.

[0131] Yb is deposited on the electron transport layer to form a thickness of An electron-injected layer is formed; then, magnesium (Mg) and silver (Ag) are co-deposited on the electron-injected layer at a deposition rate ratio of 10%:90% to form a layer with a thickness of [missing information]. The cathode.

[0132] 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.

[0133] Examples 2 to 37:

[0134] Except that, when preparing the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 3 was used instead of compound 5 in Example 1.

[0135] Comparative Examples 1 to 4:

[0136] Except that, when preparing the second hole transport layer, the organic electroluminescent device was prepared using the same method as in Example 1, except that the compound in Table 3 was used instead of compound 5 in Example 1.

[0137] The compounds used in preparing the devices of the above embodiments and comparative examples are shown below:

[0138] The performance of the red organic electroluminescent devices prepared in Examples 1-37 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the condition of 30 mA / cm. 2 The lifespan of the T95 device was tested under the following conditions, and the test results are shown in Table 3 below.

[0139] Table 3

[0140] As can be seen from Table 3 above, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the performance of the organic electroluminescent devices of Examples 1 to 37 has been greatly improved, mainly in that the luminous efficiency has been increased by at least 13.6% and the T95 lifetime has been increased by at least 13.8%.

[0141] 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.

[0142] It should also be noted that the various specific technical features described in the above embodiments can be combined in any suitable manner without contradiction. In order to avoid unnecessary repetition, this application will not describe the various possible combinations separately.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula 1: Where X is selected from C(R1R2), N(R3), O or S; R1, R2, and R3 may be the same or different, and each is independently selected from alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring. Ar is selected from aryl groups having 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 heteroaryl groups with 3 to 30 carbon atoms; Ar1 is selected from substituted or unsubstituted aryl groups with 10 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms; The substituents in L1, L2, and Ar1 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, trialkylsilyl with 3 to 12 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterylaryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms; Each R is selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms. The substituents in R may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or heteroaryl with 3 to 20 carbon atoms. m is the number of R, and m is selected from 0, 1, 2, 3, 4, 5, 6 or 7. When m is greater than 1, any two R are the same or different; or any two adjacent R form a saturated or unsaturated 3 to 15-membered ring.

2. The organic compound according to claim 1, wherein, Each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiopheneyl or carbazoleyl; or any two Rs form a benzene ring, naphthyl ring or phenanthrene ring.

3. The organic compound according to claim 1 or 2, wherein, Ar1 is selected from substituted or unsubstituted aryl groups with 10 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms; Optionally, the substituents in Ar1 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trialkylsilyl with 3 to 6 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterylalkyl with 1 to 5 carbon atoms, alkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterylaryl with 6 to 12 carbon atoms, or heteroaryl with 5 to 12 carbon atoms.

4. The organic compound according to any one of claims 1 to 3, wherein, Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoyl. Optionally, the substituents in Ar1 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

5. The organic compound according to any one of claims 1 to 4, wherein, Ar1 is selected from the group consisting of the following groups:

6. The organic compound according to any one of claims 1 to 5, wherein, Ar is selected from the group consisting of the following groups:

7. The organic compound according to any one of claims 1 to 6, wherein, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms; Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, alkyl, phenyl or deuterated phenyl with 1 to 5 carbon atoms.

8. The organic compound according to any one of claims 1 to 7, wherein, L1 and L2 may be the same or different, and each is independently selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuterated methyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

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

10. The organic compound according to any one of claims 1 to 9, wherein, R1, R2, and R3 may be the same or different, and each is independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl; or R1 and R2 form a fluorene ring.

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

12. 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 11.

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

14. An electronic device, characterized in that, The electronic device includes the electronic components as described in claim 12 or 13.

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