Organic compound, and electronic element and electronic device using same

Abstract

The present application relates to an organic compound, and an electronic element and an electronic device using the same. The organic compound has a structure as shown in a formula 1, and when the organic compound is applied to an organic electroluminescent device, the performance of the device can be remarkably improved. # imgabs0 #

Description

Technical Field

[0001] The present application relates to the field of organic electroluminescence, and in particular, to an organic compound and an electronic component and an electronic device using the same. Background Art

[0002] Organic electroluminescent devices (OLEDs) are devices made by depositing a layer of organic material between two metal electrodes via spin coating or vacuum evaporation. The device structure and light-emitting principle of OLEDs are simple. A single-color OLED device has an anode and a cathode at either end, sandwiched between several layers of stacked organic functional materials, forming the device's organic light-emitting layer. By injecting current into the device's terminals, the organic light-emitting layer emits light, with different materials emitting different colors: white light is generally required for lighting, while red, green, and blue are generally required for displays. These devices are self-luminous and do not require additional backlighting or excitation light, offering unique advantages for both display and lighting applications. After nearly a decade of rapid development, OLEDs have established a significant market share and continue to grow rapidly. They are considered by the industry to be the fourth generation of display technology after LCD.

[0003] The primary challenges facing existing organic electroluminescent devices (OLEDs) lie in their lifespan and efficiency. As displays expand in size, driving voltages also increase. Research into improving the performance of OLED devices involves reducing driving voltage, increasing luminous efficiency, and extending device lifespan. To enhance OLED device performance, device designs incorporate, in addition to the traditional anode, cathode, and light-emitting layer, a variety of organic functional layers to form a complete device. To further improve device efficiency and lifespan and balance hole injection and transport, a luminescence adjustment layer (LAL) is added between the organic light-emitting layer and the hole transport layer. LALs typically possess high hole mobility and low ionization potential and are crucial components of OLEDs. Continuing research and development of new LAL materials is necessary to further enhance the performance of OLEDs. Summary of the Invention

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

[0005] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0006]

[0007] wherein X is selected from C(R1R2), N(R3), O or S;

[0008] R1, R2 and R3 are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring;

[0009] Ar is selected from an aromatic group having 6 to 12 carbon atoms;

[0010] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar1 is selected from a substituted or unsubstituted aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0012] The substituents in L1, L2 and Ar1 are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0013] Each R is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0014] The substituents in R are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0015] 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 Rs are the same or different; or any two adjacent Rs form a saturated or unsaturated 3-15 membered ring.

[0016] A second aspect of the present application provides an electronic component, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.

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

[0018] The compound designed in this application contains 2,5-disubstituted phenyl aromatic amine as the mother core structure. The structural characteristics of this structure are: the aromatic ring substituent is connected to the ortho position of the aromatic amine group on the benzene ring, and this structure can effectively improve the spatial distortion of the molecule. The resulting asymmetric structure molecule can improve the film forming properties of the material during vapor deposition and improve the thickness uniformity of the organic functional film, thereby greatly improving the life of the device; at the same time, the ortho-biphenyl is connected to the meta position of the aromatic amine group (the para position of the aromatic substituent). This twisted terphenyl structure connects the power-supplying biphenyl group to the aromatic amine group through the meta position, which can reduce the spatial overlap area of ​​the HOMO orbital and the LUMO orbital of the smaller molecule, thereby improving the E of the molecule. g energy level and T1 energy level, thereby further improving the lifespan while improving the luminous efficiency; in addition, selecting a dibenzopentacyclic planar structure with high carrier mobility can enhance the electron blocking effect of the device and improve the luminous efficiency of the device.

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

[0020] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

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

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

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

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

[0025] Description of Reference Numerals

[0026] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, hole blocking layer; 350, electron transport layer; 360, electron injection layer; 370, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. DETAILED DESCRIPTION

[0027] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of 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 concepts of the 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 provide a full understanding of the embodiments of the present application.

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

[0029]

[0030] wherein X is selected from C(R1R2), N(R3), O or S;

[0031] R1, R2 and R3 are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring;

[0032] Ar is selected from an aromatic group having 6 to 12 carbon atoms;

[0033] L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a heteroarylene group having 3 to 30 carbon atoms;

[0034] Ar1 is selected from a substituted or unsubstituted aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0035] The substituents in L1, L2 and Ar1 are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0036] Each R is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0037] The substituents in R are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0038] 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 Rs are the same or different; or any two adjacent Rs form a saturated or unsaturated 3-15 membered ring.

[0039] “Any two adjacent substituents” may include two substituents on the same atom, or one substituent each on two adjacent atoms; when two substituents are on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly connected; when two adjacent atoms each have one substituent, the two substituents may be fused into a ring.

[0040] In this application, the descriptions used in this application are interchangeable with "each ... independently is" and "... are respectively independently" and "... are each independently" and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, " Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0041] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group or an unsubstituted aryl group having the substituent Rc. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0042] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group with 12 carbon atoms, the total number of carbon atoms in the arylene group and its substituents is 12.

[0043] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by a carbon-carbon bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon bond, two or more condensed ring aryl groups connected by a carbon-carbon bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon bond can also be considered as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. For example, in the present application, biphenyl, terphenyl etc. are aryl. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, In the present application, the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.

[0044] In this application, terphenyl includes

[0045] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0046] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are substituted by groups such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, etc. It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to a total number of carbon atoms in the aryl group and the substituents.

[0047] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and 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 multiple aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto. In the present application, the heteroarylene group refers to a divalent group formed by further losing a hydrogen atom from a heteroaryl group.

[0048] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, a deuterated alkyl group, etc. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, a phenyl-substituted dibenzofuranyl group, a phenyl-substituted dibenzothienyl group, a phenyl-substituted pyridyl group, etc. It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0049] In the present application, the number of carbon atoms of the aryl group 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 the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, and naphthyl.

[0050] In the present application, the number of carbon atoms of the heteroaryl group 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 the heteroaryl group as a substituent include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, quinolyl, quinazolinyl, quinoxalinyl, and isoquinolyl.

[0051] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

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

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

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

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

[0056] In this application, a non-positioned connecting bond refers to a single bond extending from the ring system. This means that one end of the link can be connected to any position in the ring system that the link passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0057]

[0058] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0059]

[0060] In some embodiments of the present application, the organic compound of the present application is selected from the structure shown in the following formula I-1, formula I-2, formula I-3, formula I-4, formula I-5 or formula I-6:

[0061]

[0062]

[0063] In some embodiments of the present application, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trideuteromethyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; or any two R form a benzene ring, a naphthalene ring or a phenanthrene ring.

[0064] In some embodiments of the present application, R1, R2 and R3 are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; or R1 and R2 form a fluorene ring.

[0065] In some embodiments of the present application, Ar1 is selected from a substituted or unsubstituted aryl group having 10 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. For example, Ar1 is selected from a substituted or unsubstituted aryl group having 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0066] Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

[0067] In some embodiments of the present application, Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0068] Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

[0069] In some embodiments of the present application, Ar1 is selected from the group consisting of:

[0070]

[0071] In some embodiments of the present application, Ar1 is selected from the group consisting of:

[0072]

[0073] In some embodiments of the present application, Ar is selected from the group consisting of:

[0074]

[0075] In some embodiments of the present application, Ar is selected from the group consisting of:

[0076]

[0077] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms. For example, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0078] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuteromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a deuterated phenyl group.

[0079] In some embodiments of the present application, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group.

[0080] Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuteromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

[0081] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0082]

[0083] In some embodiments of the present application, L1 and L2 are the same or different, and are each independently selected from a single bond or the group consisting of the following groups:

[0084]

[0085] In some embodiments of the present application, Selected from the group consisting of:

[0086]

[0087] In some embodiments of the present application, Selected from the group consisting of:

[0088]

[0089]

[0090] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect, the present application provides an electronic component comprising an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0104] Optionally, the functional layer includes a hole transport layer, and the hole transport layer contains the organic compound.

[0105] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device.

[0106] Optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0107] Further optionally, the hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer, wherein the second hole transport layer contains the organic compound of the present application.

[0108] In one embodiment, the electronic component is an organic electroluminescent device. Figure 1 As shown, the organic electroluminescent device may include a stacked anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330, an electron transport layer 350, and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0109] Optionally, the anode 100 includes the following anode materials, preferably materials with a large 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) is included as the anode.

[0110] 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 make special provisions for this. For example, the material of the first hole transport layer is selected from the group consisting of the following compounds:

[0111]

[0112] In one specific embodiment, the first hole transport layer 321 is HT-1.

[0113] In another embodiment, the second hole transport layer 322 is the compound of the present application.

[0114] Optionally, the second hole transport layer 322 is also called a hole adjustment layer, an electron blocking layer, a hole auxiliary layer, a hole buffer layer, a luminescence auxiliary layer or a luminescence adjustment layer.

[0115] Alternatively, the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a host material and a guest material. Alternatively, the organic light-emitting layer 330 may be composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may 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.

[0116] The main material of the organic light-emitting layer 330 can be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and this application does not impose any special restrictions on this. The main material can be a single main material or a mixed main material. In one embodiment of the present application, the main material of the organic light-emitting layer 330 is

[0117] The guest material of the organic light-emitting layer 330 can be selected according to the prior art, for example, it can be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, etc. Specific examples of the guest material include, but are not limited to,

[0118]

[0119] In one embodiment of the present application, the guest material of the organic light emitting layer 330 is

[0120] In the present application, the hole blocking layer 340 may be a single layer structure or a multilayer structure, and may include one or more hole blocking materials. In a more specific embodiment, the material of the hole blocking layer 340 is

[0121] Optionally, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials. The electron transport material can generally include a metal complex or / and a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include but are not limited to 1,10-phenanthroline compounds such as Bphen, NBphen, ET-20, BimiBphen, or an anthracene compound, triazine or pyrimidine compound containing a hetero-nitrogen aromatic group as shown below. In one embodiment of the present application, the electron transport layer 350 is composed of ET-20 and LiQ.

[0122]

[0123] In the present application, cathode 200 may include a cathode material having a small work function that 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 containing magnesium and silver is used as the cathode.

[0124] Alternatively, as Figure 1 As shown, a hole injection layer 310 is further provided 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 may be made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. For example, the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:

[0125]

[0126] In a specific embodiment of the present application, the hole injection layer 310 is HT-1 and NDP.

[0127] Alternatively, as Figure 1 As shown, an electron injection layer 360 is further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic substance. For example, the electron injection layer 360 includes Yb.

[0128] According to another embodiment, the electronic component is a photoelectric conversion device. Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 arranged opposite to each other, and a functional layer 300 arranged between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in the present application.

[0129] According to a specific embodiment, Figure 3 As shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 370, an electron transport layer 350 and a cathode 200 stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0130] Alternatively, the photoelectric conversion device may be a solar cell, in particular an organic thin-film solar cell. For example, in one embodiment of the present application, the solar cell comprises an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked in sequence, wherein the hole transport layer comprises the organic compound of the present application.

[0131] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

[0132] According to one embodiment, Figure 2 As shown, the electronic device is a first electronic device 400, which includes the above-mentioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0133] According to another embodiment, Figure 4 As shown, the electronic device is a second electronic device 500, which includes the above-mentioned photoelectric conversion device. The second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0134] The synthesis method of the organic compound of the present application is specifically described below with reference to synthesis examples, but the present application is not limited thereto.

[0135] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0136] Synthesis example

[0137] 1. Synthesis of intermediate IM a1-1

[0138]

[0139] (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 under nitrogen for 15 min. Bis(triphenylphosphine)palladium dichloride (0.44 g, 0.63 mmol) was added and the temperature was raised to 75°C to 80°C and stirred for 5 h. The reaction solution was cooled to room temperature and washed with water several times until neutral and then dried over anhydrous magnesium sulfate. The organic phase was decompressed to remove the solvent and then washed with ethanol to obtain a white solid IM a1-a (14.50 g, yield 66.95%).

[0140]

[0141] (2) The intermediate IM a1-a (10.00 g, 29.10 mmol), phenylboric 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 under nitrogen for 15 min. Bis(triphenylphosphine)palladium dichloride (0.20 g, 0.29 mmol) was added and the temperature was raised to 75°C to 80°C and stirred for 6 h. The reaction solution was cooled to room temperature and washed with water several times until neutral and then dried over anhydrous magnesium sulfate. The organic phase was decompressed to remove the solvent and then washed with ethanol to obtain a white solid IM a1-a1 (7.10 g, yield 71.56%).

[0142] The other IM a1-X listed in Table 1 were synthesized by referring to the synthesis method of IM a1-1, except that raw material 1 was used instead of phenylboronic acid in the above step (2). The main raw materials used, the synthesis of IM a1-X, and the yield of the last step are shown in Table 1.

[0143] Table 1

[0144]

[0145] Synthesis Example 1: Synthesis of Compound 5

[0146]

[0147] IM a1-1 (6.00 g, 17.60 mmol), N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-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, The mixture was stirred for 3 h at room temperature, and the mixture was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate and filtered, and the filtrate was decompressed to remove the solvent. The crude product was recrystallized from toluene to obtain compound 5 (7.60 g, yield 64.85%) as a white solid; mass spectrum (m / z) = 666.3 [M+H] + .

[0148] The compounds listed in Table 2 were synthesized by referring to the method for compound 5, except that raw material 2 was used instead of IM a1-X, and raw material 3 was used instead of N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-3-amine. The main raw materials used, the synthesized compounds and their yields, and the mass spectrometry results are shown in Table 2.

[0149] Table 2

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] NMR data of compound 5

[0158] 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).

[0159] NMR data of compound 167

[0160] 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).

[0161] NMR data of compound 229

[0162] 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).

[0163] Example 1: Red organic electroluminescent device

[0164] First, the anode pretreatment is carried out through the following process: the thickness is The ITO / Ag / ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (height) and surface treated with ultraviolet light, ozone and O2:N2 plasma to increase the work function of the anode. The surface of the experimental substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the experimental substrate.

[0165] On the above substrate, compound HT-1 and NDP were co-evaporated at an evaporation rate ratio of 97%:3% to form a film with a thickness of hole injection layer.

[0166] Compound HT-1 was evaporated on the hole injection layer to form a layer with a thickness of The first hole transport layer.

[0167] Compound 5 is evaporated on the first hole transport layer to form a layer with a thickness of a second hole transport layer.

[0168] On the second hole transport layer, compound p-RH, compound n-RH, and compound RD were co-evaporated at an evaporation rate ratio of 63%:37%:2% to form a layer with a thickness of organic light-emitting layer.

[0169] Compound HB-1 is evaporated on the organic light emitting layer to form a layer with a thickness of hole blocking layer.

[0170] Compound ET-20 and LiQ were co-evaporated on the hole blocking layer at an evaporation rate ratio of 50%:50% to form a layer with a thickness of electron transport layer.

[0171] Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, on the electron injection layer, magnesium (Mg) and silver (Ag) are co-evaporated at an evaporation rate ratio of 10%:90% to form a thickness of cathode.

[0172] Finally, compound CP-1 is evaporated on the cathode to form a layer with a thickness of The cathode covering layer is formed, thereby completing the preparation of the red organic electroluminescent device.

[0173] Example 2 to Example 37:

[0174] An 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 when preparing the second hole transport layer.

[0175] Comparative Examples 1 to 4:

[0176] An 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 when preparing the second hole transport layer.

[0177] Among them, when preparing the devices of the above embodiments and comparative examples, the compound structures used are as follows:

[0178]

[0179] The performance of the red organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Examples 1 to 4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of 30mA / cm 2 The T95 device life was tested under the conditions of , and the test results are shown in Table 3 below.

[0180] Table 3

[0181]

[0182]

[0183] As shown in 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 is greatly improved, mainly manifested in that the luminous efficiency is increased by at least 13.6% and the T95 life is increased by at least 13.8%.

[0184] The preferred embodiments of the present application are described in detail above in conjunction with the accompanying drawings. However, the present application is not limited to the specific details in the above embodiments. Within the technical concept of the present application, various simple modifications can be made to the technical solution of the present application, and these simple modifications all fall within the scope of protection of the present application.

[0185] It should also be noted that the various specific technical features described in the above specific embodiments can be combined in any appropriate manner unless there is any contradiction. In order to avoid unnecessary repetition, this application will not further describe various possible combinations.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in Formula 1: wherein X is selected from C(R1R2), N(R3), O or S; R1, R2 and R3 are the same or different and are each independently selected from an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; or R1 and R2 form a saturated or unsaturated 3 to 15-membered ring; Ar is selected from an aromatic group having 6 to 12 carbon atoms; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a heteroarylene group having 3 to 30 carbon atoms; Ar1 is selected from a substituted or unsubstituted aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L1, L2 and Ar1 are each independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; Each R is selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in R are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 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 Rs are the same or different; or any two adjacent Rs form a saturated or unsaturated 3-15 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, trideuteromethyl, trifluoromethyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; or any two Rs form a benzene ring, a naphthalene ring or a phenanthrene ring.

3. The organic compound according to claim 1, wherein Ar1 is selected from a substituted or unsubstituted aryl group having 10 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, a trialkylsilyl group having 3 to 6 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms, a deuterated aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms.

4. The organic compound according to claim 1, wherein Ar1 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

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

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

7. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms; Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuteromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms, a phenyl group or a deuterated phenyl group.

8. The organic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group; Optionally, the substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trideuteromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or deuterated phenyl.

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

10. The organic compound according to claim 1, wherein R1, R2 and R3 are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, pyrimidinyl, pyrazinyl, dibenzofuranyl, dibenzothienyl or carbazolyl; or R1 and R2 form a fluorene ring.

11. The organic compound according to claim 1, 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 the organic compound according to 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 organic electroluminescent device.

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

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