Organic compounds, electronic component using same and electronic apparatus

Abstract

The present application relates to organic compounds, an electronic component using same and an electronic apparatus. The organic compounds have structures as shown in formula I, and applying the organic compounds to organic electroluminescent devices can significantly improve the performance of the devices.

Description

Organic compound and electronic component and electronic device using the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. 202310693446.6 filed on June 12, 2023. The entire contents of the above Chinese patent application are incorporated into this application by reference. Technical Field

[0003] The present application relates to the technical field of organic electroluminescence, and in particular to an organic compound and an electronic component and an electronic device using the same. Background Art

[0004] With the development of electronic technology and advancements in materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly widespread. Such electronic components generally include a cathode and an anode arranged in opposite directions, and a functional layer disposed between the cathode and the anode. This functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer located between the energy conversion layer and the anode, and an electron transport layer located between the energy conversion layer and the cathode.

[0005] Taking an organic electroluminescent device as an example, it generally consists of an anode, a hole transport layer, an electroluminescent layer (which serves as an energy conversion layer), an electron transport layer, and a cathode, all stacked in sequence. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of this electric field, electrons on the cathode side migrate toward the electroluminescent layer, and holes on the anode side also migrate toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, causing the electroluminescent layer to emit light outward.

[0006] However, the efficiency, service life and other performance of organic electroluminescent devices still need to be further improved compared with the application requirements of products. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices.

[0007] Summary of the Invention

[0008] 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.

[0009] The first aspect of the present application provides an organic compound having a structure shown in Formula I:

[0010] wherein X is selected from O, S or N(R3);

[0011] R3 is selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 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;

[0012] L, 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0013] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0014] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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] Each R is 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0016] n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

[0017] 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.

[0018] A third aspect of the present application provides an electronic device comprising the electronic component described in the second aspect of the present application.

[0019] The main structural feature of the organic compound of the present application is a dibenzo five-membered heterocyclic ring. The same benzene ring is trisubstituted, wherein the substituents at positions 1 and 2 of the dibenzo pentacyclic ring are both phenyl, and the 3rd or 4th position is connected to the aromatic amine group. In this connection mode, on the one hand, the connection of phenyl groups at positions 1 and 2 of the dibenzo pentacyclic ring can enhance the spatial stereoscopic properties of the molecule and improve the carrier mobility of the compound; on the other hand, the connection of aromatic amine at positions 3 or 4 of the dibenzo pentacyclic ring increases the degree of molecular conjugation, effectively improves the transmission efficiency of the compound, and makes the compound have a high Tg, so when the OLED device is driven, the compound can be prevented from crystallizing, thereby improving the service life of the device. When the compound of the present application is used as a hole transport material, the carrier balance in the organic light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the device efficiency and life can be improved.

[0020] Other features and advantages of the present application will be described in detail in the subsequent detailed description. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] 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.

[0022] FIG1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0023] FIG2 is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0024] FIG3 is a schematic structural diagram of a photoelectric conversion device according to an embodiment of the present application.

[0025] FIG4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0026] Description of Reference Numerals

[0027] 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 320, hole transport layer; 321, first hole transport layer; 322, second hole transport layer; 330, organic light-emitting layer; 340, electron transport layer; 350, electron injection layer; 360, photoelectric conversion layer; 400, first electronic device; 500, second electronic device. DETAILED DESCRIPTION

[0028] 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.

[0029] In a first aspect, the present application provides an organic compound having a structure shown in Formula I:

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

[0031] R3 is selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 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;

[0032] L, 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, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0033] Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0034] The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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;

[0035] Each R is 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0036] n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

[0037] In this application, the terms "optionally" and "optionally" mean that the subsequently described event or circumstance may but need not occur, and the description includes situations where the event or circumstance occurs or does not occur. For example, "optionally, two adjacent substituents form a ring" means that the two substituents may form a ring but do not need to form a ring, including situations where the two adjacent substituents form a ring and situations where the two adjacent substituents do not form a ring.

[0038] In this application, the descriptions “each independently selected from” and “respectively independently selected from” are interchangeable 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.

[0039] 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 a 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 deuterated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, etc.

[0040] 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.

[0041] In this application, the substituent "D" represents deuteration.

[0042] 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.

[0043] In the present application, a substituted aryl group may be an aryl group in which one or more hydrogen atoms are replaced 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. 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 means that the total number of carbon atoms in the aryl group and the substituents is 18.

[0044] 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 a plurality of aromatic ring systems connected by conjugated 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.

[0045] In the present application, a substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced 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. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.

[0046] In the present application, the number of carbon atoms of the aryl group as a substituent may be 6 to 20, for example, the number of carbon atoms may be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, and specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, anthracenyl, base.

[0047] In the present application, the number of carbon atoms of the heteroaryl group as a substituent can be 3 to 20, for example, the number of carbon atoms can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20. 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.

[0048] 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.

[0049] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0050] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0051] In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0052] In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0053] 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):

[0054] 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):

[0055] In some embodiments of the present application, the organic compound has a structure shown in the following Formula 1 to Formula 6:

[0056] In some embodiments of the present application, R3 is selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, deuterated phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0057] In some embodiments of the present application, each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0058] In some embodiments of the present application, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms. For example, L, 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, and a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0059] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

[0060] In some embodiments of the present application, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted carbazolyl group.

[0061] Alternatively, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

[0062] In some embodiments of the present application, L, L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0063] In some embodiments of the present application, L is selected from the group consisting of a single bond or the following groups:

[0064] In some embodiments of the present application, L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0065] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms. For example, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 10, 20, 21, 22, 23, 24 or 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0066] Optionally, the substituents in Ar1 and Ar2 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, or a heteroaryl group having 5 to 12 carbon atoms.

[0067] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted cyclopentanespirofluorene, substituted or unsubstituted cyclohexanespirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.

[0068] Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

[0069] In some embodiments of the present application, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

[0070] Further optionally, Ar1 and Ar2 are each independently selected from the group consisting of the following groups:

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

[0072] In some embodiments of the present application, Each is independently selected from the group consisting of:

[0073] Specifically, the organic compound is selected from the group consisting of the following compounds:

[0074] 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.

[0075] Optionally, the functional layer includes a hole transport layer, and the hole transport layer includes the organic compound of the present application.

[0076] Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device. Further optionally, the organic electroluminescent device is a red organic electroluminescent device.

[0077] 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.

[0078] In one embodiment, the electronic component is an organic electroluminescent device. As shown in FIG1 , the organic electroluminescent device may include a stacked anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200. The first hole transport layer 321 and the second hole transport layer 322 constitute the hole transport layer 320.

[0079] 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.

[0080] 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:

[0081] In one specific embodiment, the first hole transport layer 321 is compound HT-21.

[0082] Optionally, the second hole transport layer 322 is an organic compound of the present application.

[0083] 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.

[0084] The host 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 specific restrictions on this. The host material can be a single host material or a mixed host material. In one embodiment of the present application, the host material of the organic light-emitting layer 330 is CBP.

[0085] 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,

[0086] In one embodiment of the present application, the guest material of the organic light-emitting layer 330 is Ir(piq)2(acac).

[0087] Optionally, the electron transport layer 340 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 and / or 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-21, 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 340 is composed of ET-21 and LiQ.

[0088] 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.

[0089] Optionally, as shown in FIG1 , 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:

[0090] In a specific embodiment of the present application, the hole injection layer 310 is F4-TCNQ.

[0091] Optionally, as shown in FIG1 , an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include 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 compound. For example, the electron injection layer 350 includes LiQ.

[0092] According to 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 each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes the organic compound provided in this application.

[0093] According to a specific embodiment, as shown in Figure 3, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200 stacked in sequence. Optionally, the hole transport layer 320 comprises the organic compound of the present application.

[0094] 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.

[0095] In a third aspect, the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.

[0096] According to one embodiment, as shown in FIG2 , the electronic device is a first electronic device 400, which includes the organic electroluminescent device described above. 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, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, and the like.

[0097] According to another embodiment, as shown in FIG4 , 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 photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0098] 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.

[0099] The compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.

[0100] Synthesis example

[0101] 1. Synthesis of IM e-1

[0102] A three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser was purged with nitrogen (0.100 L / min) for 15 minutes. The raw materials, 1,3,4-tribromo-2,5-dichlorobenzene (50 g, 130.3 mmol), phenylboric acid (35 g, 286.7 mmol), tetrakis(triphenylphosphine)palladium (0.75 g, 0.65 mmol), and potassium carbonate (71.9 g, 520.2 mmol), were added in sequence. A mixed solvent of toluene (400 mL), ethanol (200 mL), and water (100 mL) was also added. Stirring was initiated and the temperature was raised to 78°C–80°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature. The reaction mixture was washed with water, the organic phase separated, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent, yielding a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane to afford IM e-1 (20.7 g, 42% yield).

[0103] IM e-2 listed in Table 1 was synthesized in the same manner as IM e-1, except that raw material 1 was used instead of 1,3,4-tribromo-2,5-dichlorobenzene. The main raw materials used, the synthesized intermediates and their yields are shown in Table 1:

[0104] Table 1

[0105] 2. Synthesis of IM f-1

[0106] A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100 L / min) for 15 minutes. IM e-1 (20 g, 52.9 mmol), o-hydroxyphenylboronic acid (8 g, 58.0 mmol), tetrakis(triphenylphosphine)palladium (0.61 g, 0.53 mmol), and potassium carbonate (14.6 g, 105.8 mmol) were added in sequence. A mixed solvent of toluene (160 mL), ethanol (80 mL), and water (40 mL) was also added. Stirring was initiated and the temperature was raised to 78°C–80°C for 8 hours. After completion of the reaction, the mixture was cooled to room temperature. The reaction mixture was washed with water, the organic phase separated, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent, yielding a crude product. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain IM f-1 (17 g, 82% yield).

[0107] IM fx listed in Table 2 was synthesized in the same manner as IM f-1, except that raw material 2 was used instead of IM e-1, and raw material 3 was used instead of o-hydroxyphenylboronic acid. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 2:

[0108] Table 2

[0109] 3. Synthesis of IM G-1

[0110] A three-necked flask equipped with a mechanical stirrer, thermometer, and spherical condenser was purged with nitrogen (0.200 L / min) for 15 minutes. IM f-1 (17 g, 43.4 mmol), potassium carbonate (12 g, 86.8 mmol), and acetonitrile (150 mL) were then added sequentially. The mixture was refluxed for 5 hours. After completion of the reaction, the mixture was cooled to room temperature. The organic phase was extracted with dichloromethane and water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane to obtain IM G-1 (13.6 g, 88% yield).

[0111] IM F-2 listed in Table 3 was synthesized in the same manner as IM F-1, except that IM F-2 was used instead of IM F-1. The main raw materials used, the synthesized intermediates and their yields are shown in Table 3:

[0112] Table 3

[0113] 4. Synthesis of IM H-1

[0114] A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was replaced with nitrogen (0.200 L / min) for 15 min, and IM f-3 (15 g, 34.3 mmol) and sulfuric acid (50 mL) were added sequentially. The reaction was refluxed for 6 h. After the reaction was completed, 500 mL of 1 mol / L NaOH solution was added and stirred for 1 h. The generated solid was filtered and recrystallized from toluene to obtain IM H-1 (11 g, yield 86%).

[0115] IM H-2 listed in Table 4 was synthesized in the same manner as IM H-1, except that IM f-4 was used instead of IM f-3. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 4:

[0116] Table 4

[0117] 5. Synthesis of IM i-1

[0118] A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was purged with nitrogen (0.100 L / min) for 15 minutes. Then, 2-nitrobenzeneboronic acid (50.0 g, 277.82 mmol), reactant A (95.47 g, 277.82 mmol), bistriphenylphosphine palladium dichloride (0.975 g, 1.4 mmol), and potassium carbonate (95.99 g, 694.56 mmol) were added in sequence. A mixed solvent of ethylene glycol dimethyl ether (400 mL) and water (100 mL) was also added. Stirring was initiated, and the temperature was raised to 78°C to 80°C for 15 hours. After completion of the reaction, the mixture was cooled to room temperature. The reaction solution was washed with water, and the organic phase was separated. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product; the crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid IM i-1 (72.03 g, yield 65%).

[0119] IMj-1 listed in Table 5 was synthesized in the same manner as IM i-1, except that raw material 4 was used instead of reactant A. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 5:

[0120] Table 5

[0121] 6. Synthesis of IM i-2

[0122] IM i-1 (72 g, 186.6 mmol), triphenylphosphine (122.35 g, 466.5 mmol) and o-dichlorobenzene (720 mL) were added to a flask, heated to 175 ° C under nitrogen protection, stirred for 18 hours and then cooled to room temperature. The reaction solution was washed with water, separated, and the organic phase was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure to obtain a crude product; the crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane system to obtain a white solid IM i-2 (56.78 g, yield 88%).

[0123] IMj-2 listed in Table 6 was synthesized in the same manner as IM i-2, except that IMj-1 was used instead of IM i-1. The main raw materials used, the synthesized intermediates, and their yields are shown in Table 6:

[0124] Table 6

[0125] 7. Synthesis of IM I-1

[0126] IM i-2 (50 g, 141.3 mmol), bromobenzene (22.18 g, 141.3 mmol), cuprous iodide (2.69 g, 14.1 mmol), potassium carbonate (48.8 g, 353.3 mmol), 1,10-phenanthroline (5.6 g, 28.3 mmol), 18-crown-6-ether (3.7 g, 14.1 mmol), and dimethylformamide (50 mL) were added to a flask. The temperature was raised to 130°C under nitrogen and stirred for 12 h. The mixture was cooled to room temperature, and dichloromethane (500 mL) and water were added to the reaction mixture. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane and then recrystallized from toluene / n-heptane to obtain IM i-1 (30.37 g, 50% yield) as a white solid.

[0127] IM J-1 listed in Table 7 was synthesized in the same manner as IM I-1, except that IM j-2 was used instead of IM i-2. The main raw materials used, the synthesized intermediates and their yields are shown in Table 7.

[0128] Table 7

[0129] 8. Synthesis of Compound A-1-3

[0130] A three-necked flask equipped with a mechanical stirrer, a thermometer, and a spherical condenser was filled with nitrogen (0.200 L / min) for 15 min, and 3-bromo-9,9-dimethyl-1,2-diphenyl-9H-fluorene (5 g, 11.8 mmol), di(4-biphenylyl)amine (3.8 g, 11.8 mmol), tris(dibenzylideneacetone)dipalladium (0.11 g, 0.12 mmol), 2-bis(dicyclohexylphosphine)-2',6'-dimethoxybiphenyl (0.1 g, 0.24 mmol), sodium tert-butoxide (1.7 g, 17.7 mmol) and toluene (50 mL) were added in sequence. The mixture was refluxed at 105°C to 110°C for 4 h. After the reaction was completed, the mixture was cooled to room temperature. The organic phase was washed with water, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was distilled under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to obtain a white solid product, compound A-1-3 (5.4 g, yield 69%); mass spectrum (m / z) = 666.31 [M+H] + .

[0131] The compounds listed in Table 8 below were synthesized in the same manner as compound A-1-3, except that raw material 5 was used instead of 3-bromo-9,9-dimethyl-1,2-diphenyl-9H-fluorene, and raw material 6 was used instead of di(4-biphenyl)amine. The main raw materials used, the synthesized compounds, their yields, and mass spectra are shown in Table 8.

[0132] Table 8

[0133] The NMR data of some compounds are shown in Table 9 below:

[0134] Table 9

[0135] Example 15: Fabrication of a red organic electroluminescent device

[0136] The anode was prepared by the following process: the thickness of The ITO / Ag / ITO substrate was cut into a size of 40 mm (length) × 40 mm (width) × 0.7 mm (thickness) and prepared into an experimental substrate with cathode and insulating layer patterns using a photolithography process. The surface was treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode (experimental substrate) and remove scum.

[0137] F4-TCNQ was vacuum evaporated on the experimental substrate (anode) to form a layer with a thickness of The hole injection layer is formed by vacuum evaporation of HT-21 to a thickness of The first hole transport layer.

[0138] Compound B-1-2 is vacuum-deposited on the first hole transport layer to form a layer having a thickness of a second hole transport layer.

[0139] On the second hole transport layer, CBP and Ir(piq)2(acac) were co-evaporated at an evaporation rate ratio of 95%:5% to form a layer with a thickness of organic light-emitting layer.

[0140] On the organic light emitting layer, ET-21 and LiQ were co-evaporated at an evaporation rate ratio of 1:1 to form a film with a thickness of LiQ is vacuum evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) are co-evaporated on the electron injection layer at an evaporation rate ratio of 1:9 to form a film with a thickness of cathode.

[0141] In addition, CP-1 is evaporated on the cathode to form a layer with a thickness of A cover layer (CPL) is formed on the organic light-emitting device to complete the manufacturing process.

[0142] Examples 16 to 35

[0143] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound B-1-2 was replaced by the compound shown in Table 11 when forming the second hole transport layer.

[0144] Comparative Examples 1 to 3

[0145] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, B, C, and D were used instead of compound B-1-2 when forming the second hole transport layer.

[0146] The main material structures used in the above embodiments and comparative examples are shown in Table 10 below:

[0147] Table 10

[0148] The performance tests of the devices prepared in the examples and comparative examples were carried out, wherein the IVL (operating voltage, current efficiency, color coordinates) data were obtained at 10 mA / cm 2 Tested under current density, T95 life is 20mA / cm 2 The results are shown in Table 11.

[0149] Table 11

[0150] According to the results in Table 11, Examples 15 to 35 using the organic compound of the present invention as the second hole transport material in the red organic electroluminescent device have a current efficiency improved by at least 10.63% and a lifespan improved by at least 11.2% compared to Comparative Examples 1 to 4 using the corresponding devices of the known compounds.

[0151] Therefore, the compound of the present invention has the characteristic of improving luminous efficiency.

[0152] 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.

Claims

1. An organic compound having a structure shown in Formula I: in, X is selected from O, S or N(R3); R3 is selected from an alkyl group having 1 to 5 carbon atoms, a deuterated alkyl group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 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; L, 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 substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The substituents in L, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl 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; Each R is 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms; n represents the number of R, and n is selected from 0, 1, 2, 3 or 4; when n is greater than 1, any two Rs are the same or different.

2. The organic compound according to claim 1, wherein Each R is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trimethylsilyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.

3. The organic compound according to claim 1, wherein R3 is selected from methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, deuterated phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.

4. The organic compound according to claim 1, wherein L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms; The substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, an alkyl group having 1 to 5 carbon atoms or a phenyl group.

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

6. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trialkylsilyl having 3 to 6 carbon atoms, haloalkyl having 1 to 5 carbon atoms, deuterated alkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.

7. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthryl, substituted or unsubstituted cyclopentanespirofluorene, substituted or unsubstituted cyclohexanespirofluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; The substituents in Ar1 and Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.

8. The organic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from the group consisting of:

9. The organic compound according to claim 1, wherein Each is independently selected from the group consisting of:

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

11. An electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; wherein: The functional layer contains the organic compound according to any one of claims 1 to 10.

12. The electronic component according to claim 11, wherein The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound; Optionally, the electronic component is an organic electroluminescent device or a photoelectric conversion device; Optionally, the organic electroluminescent device is a red organic electroluminescent device.

13. An electronic device comprising the electronic component according to claim 11 or 12.

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