Organic compound, electronic element using same, and electronic apparatus

Abstract

The present invention relates to an organic compound, an electronic element using same, and an electronic apparatus. The organic compound has a structure as represented by formula 1. When applied to an organic electroluminescent device, the organic compound can significantly improve the performance of the device.

Description

Organic compound, electronic element using the same, and electronic device

[0001] Cross Reference to Related Applications

[0002] This application claims priority to Chinese Patent Application No. 2024104621052, filed on April 17, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD

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

[0004] With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. The 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. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move to the organic light-emitting layer, and holes on the anode side also move to the organic light-emitting layer. The electrons and holes combine in the organic light-emitting layer to form excitons. The excitons in the excited state release energy to the outside, thereby causing the organic light-emitting layer to emit light.

[0005] Generally speaking, in a host material / dopant system, the selection of the host material is crucial because the host material has an important influence on the efficiency and lifetime of the light-emitting device. An excellent host material should have a suitable molecular weight, a high glass transition temperature and thermal decomposition temperature, a high electrochemical stability, and a good interface contact with the adjacent functional layer material. For a blue light host material, the material is required to have good carrier transport capability and a suitable triplet energy level to ensure that the energy can be effectively transferred from the host material to the guest material in the light-emitting process, thereby achieving high device efficiency. With people's continuous pursuit of high-quality electronic products, the update iteration speed of OLED screens is getting faster and faster, and at the same time, higher requirements are put forward for the performance of OLED devices. As one of the core materials of OLED devices, the development of new high-efficiency and long-life host light-emitting materials is imminent. SUMMARY

[0006] The purpose of the present application is to provide an organic compound, an electronic element using the same, and an electronic device. The use of the organic compound in an organic electroluminescent device can improve the performance of the device.

[0007] The first aspect of the present application provides an organic compound having a structure shown in Formula 1:

[0008] wherein each R1 is the same or different, and each is independently selected from hydrogen or deuterium;

[0009] Ar is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, or a substituted or unsubstituted O- or S-containing heteroaryl group having 3-30 carbon atoms;

[0010] each R2 is the same or different, and each is independently selected from hydrogen, a substituted or unsubstituted aryl group having 6-30 carbon atoms, or a substituted or unsubstituted O- or S-containing heteroaryl group having 3-30 carbon atoms;

[0011] the substituents in Ar and R2 are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3-12 carbon atoms, a haloalkyl group having 1-10 carbon atoms, an alkyl group having 1-10 carbon atoms, an aryl group having 6-20 carbon atoms, or an O- or S-containing heteroaryl group having 5-20 carbon atoms;

[0012] m represents the number of R1, and m is selected from 1, 2, or 3; when m is greater than 1, any two R1 are the same or different;

[0013] n represents the number of R2, and n is selected from 1, 2, 3, 4, or 5; when n is greater than 1, any two R2 are the same or different.

[0014] The second aspect of the present application provides an electronic element, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound described above.

[0015] The third aspect of the present application provides an electronic device comprising the electronic element described in the second aspect of the present application.

[0016] The compound of the present application is 9-([1,1':2',1"-terphenyl]-3-yl)-9H-3,9'-biscarbazole as a mother nucleus structure, wherein the substituents connected to positions 1 and the phenyl group at position 3 make the overall molecule have a good spatial configuration and stereogenicity, so that the compound has a high glass transition temperature and can be well maintained in an amorphous state after being evaporated into a film; in addition, the ortho-substituted structure of the biscarbazole and terphenyl in the mother nucleus has a good spatial configuration, which can reduce the concentration quenching phenomenon caused by the stacking of doped materials, and at the same time make the entire molecule have a high first excited triplet energy level, so that when the compound of the present application is used as a blue light host material, the energy transfer efficiency of the host material to the blue light doped material can be improved, the excitation generation and utilization efficiency can be improved, and the device luminous efficiency and service life can be improved.

[0017] Other features and advantages of the present application will be set forth in the following detailed description. BRIEF DESCRIPTION OF DRAWINGS

[0018] The accompanying drawings are included to provide a further understanding of the present application and are incorporated in and constitute a part of this specification, illustrate embodiments of the present application and together with the description serve to explain the principles of the present application.

[0019] FIG. 1 is a schematic diagram of an organic electroluminescent device according to an embodiment of the present application.

[0020] FIG. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.

[0021] BRIEF DESCRIPTION OF DRAWINGS 100, anode; 200, cathode; 300, functional layer; 310, hole injection layer; 321, hole transport layer; 322, electron blocking layer; 330, organic light emitting layer; 340, electron transport layer; 350, electron injection layer; 400, electronic device DETAILED DESCRIPTION

[0022] Example embodiments now will be described more fully hereinafter with reference to the accompanying drawings. Example embodiments, may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the example embodiments to those skilled in the art. The features, structures, or characteristics described in connection with the embodiments can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application. The specific

[0023] In a first aspect, the present application provides an organic compound having a structure represented by Formula 1:

[0024] wherein each R1 is the same or different, and each is independently selected from hydrogen or deuterium;

[0025] Ar is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted O- or S-containing heteroaryl group having 3 to 30 carbon atoms;

[0026] each R2 is the same or different, and each is independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted O- or S-containing heteroaryl group having 3 to 30 carbon atoms;

[0027] the substituents in Ar and R2are the same or different, and each is independently selected from the group consisting of 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, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an O- or S-containing heteroaryl group having 5 to 20 carbon atoms;

[0028] m represents the number of R1, and m is selected from 1, 2, or 3; when m is greater than 1, any two R1are the same or different;

[0029] n represents the number of R2, and n is selected from 1, 2, 3, 4, or 5; when n is greater than 1, any two R2are the same or different.

[0030] In the present application, the description "independently selected from" and "independently selected from" can be interchangeable, and should be interpreted broadly, which means that the specific options expressed by the same symbols in different groups do not affect each other, or the specific options expressed by the same symbols in the same group do not affect each other. For example, "R1and R2are each independently selected from the group consisting of hydrogen, 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, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an O- or S-containing heteroaryl group having 5 to 20 carbon atoms" means that R1and R2are each independently selected from the group consisting of hydrogen, 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, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an O- or S-containing heteroaryl group having 5 to 20 carbon atoms. wherein each q is independently 0, 1, 2, or 3, and each R" is independently selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, and the meaning is that: formula Q-1 represents that there are q substituents R" on the benzene ring, each R" can be the same or different, and each R" is selected independently; formula Q-2 represents that there are q substituents R" on each benzene ring of the biphenyl, 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 each R" is selected independently.

[0031] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can have or not have a substituent (hereinafter, the substituent will be collectively referred to as Rc for the sake of description). For example, "substituted or unsubstituted aryl" means an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent Rc, for example, can be deuterium, a halogen group, a cyano group, an alkyl group, a trialkylsilyl group, a haloalkyl group, an aryl group, a heteroaryl group, and the like.

[0032] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0033] In the present application, an aryl group refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, or two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be considered as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, In the present application, an aryl group refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, or two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be considered as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of the aryl group can include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene,

[0034] In the present application, a substituted aryl group can be an aryl group in which one or more hydrogen atoms in the aryl group is substituted with 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 haloalkyl group, a deuterated alkyl group, and the like. Specific examples of the heteroaryl-substituted aryl group include, but are not limited to, a dibenzofuranyl-substituted phenyl group, a dibenzothiophenyl-substituted phenyl group, a pyridyl-substituted phenyl group, and the like. It should be understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent group on the aryl group, for example, a substituted aryl group having 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituent group being 18.

[0035] In the present application, a heteroaryl group refers to a monovalent aromatic ring or its derivative 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. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon bond in conjugation, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl group can include a thienyl group, a furanyl 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 pyrimidinyl 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 benzothiophenyl group, a dibenzothiophenyl group, a thienothiophenyl 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, but is not limited thereto. In the present application, a heteroarylene group refers to a divalent group formed by further losing one hydrogen atom from the heteroaryl group.

[0036] In the present application, a substituted heteroaryl group can be a heteroaryl group in which one or more hydrogen atoms in the heteroaryl group is substituted with 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 halogenated alkyl group, a deuterated alkyl group, and the like. Specific examples of the aryl-substituted heteroaryl group include, but are not limited to, a phenyl-substituted dibenzofuranyl group, a phenyl-substituted dibenzothiophenyl group, a phenyl-substituted pyridyl group, and the like. It should be understood that the number of carbon atoms of the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituent group on the heteroaryl group.

[0037] In the present application, the number of carbon atoms of the aryl group as a substituent group can be 6 to 20, for example, the number of carbon atoms can 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 group include, but are not limited to, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group,

[0038] In the present application, the number of carbon atoms of the heteroaryl group as a substituent group 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, and specific examples of the heteroaryl group as a substituent group include, but are not limited to, a pyridyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, an isoquinolyl group.

[0039] ​In the present application, the number of carbon atoms of an alkyl group having 1 to 10 carbon atoms 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, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0040] In the present application, a halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0041] In the present application, specific examples of a trialkylsilyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.

[0042] In the present application, specific examples of a haloalkyl group include, but are not limited to, a trifluoromethyl group.

[0043] In the present application, specific examples of a deuterated alkyl group include, but are not limited to, a trideuteromethyl group.

[0044] In the present application, an unspecified position connecting bond is a single bond extending from a ring system which indicates that one end of the connecting bond can be connected to any position in the ring system through which the bond extends, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions in the molecule through two unspecified position connecting bonds extending through the bicyclic ring, and the meaning represented thereby includes any of the possible connection modes shown in formulae (f-1) to (f-10):

[0045] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule through one unspecified position connecting bond extending from the middle of one of the benzene rings, and the meaning represented thereby includes any of the possible connection modes shown in formulae (X'-1) to (X'-4):

[0046] In some embodiments of the present application, Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted O- or S-containing heteroaryl group having 12 to 18 carbon atoms. For example, Ar is selected from the group consisting of a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and a substituted or unsubstituted O- or S-containing heteroaryl group having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0047] Optionally, the substituents in Ar are the same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl group having 3 to 6 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms, or O- or S-containing heteroaryl group having 5 to 12 carbon atoms.

[0048] In some embodiments of the application, Ar is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0049] Optionally, the substituents in Ar are the same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl group having 3 to 6 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms, or O- or S-containing heteroaryl group having 5 to 12 carbon atoms.

[0050] In some embodiments of the application, Ar is selected from the group consisting of:

[0051] In some embodiments of the application, Ar is selected from the group consisting of:

[0052] In some embodiments of the application, each R2 is the same or different, and each is independently selected from hydrogen, substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and O- or S-containing heteroaryl group having 12 to 18 carbon atoms. For example, each R2 is independently selected from hydrogen, substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and O- or S-containing heteroaryl group having 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0053] Optionally, the substituents in R2 are the same or different, and each is independently selected from deuterium, fluorine, cyano, trialkylsilyl group having 3 to 6 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms, or O- or S-containing heteroaryl group having 5 to 12 carbon atoms.

[0054] In some embodiments of the present application, each R2is the same or different, and each is independently selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.

[0055] Optionally, the substituents in R2are the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, and dibenzothiophenyl.

[0056] In some embodiments of the present application, each R2is the same or different, and each is independently selected from the group consisting of hydrogen or the following group:

[0057] In some embodiments of the present application, each R2is the same or different, and each is independently selected from the group consisting of hydrogen or the following group:

[0058] In particular, the organic compound is selected from the group consisting of the following compounds:

[0059] In a second aspect, the present application provides an electronic element, comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.

[0060] Optionally, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound of the present application.

[0061] Optionally, the electronic element is an organic electroluminescent device.

[0062] In an embodiment, the electronic element is an organic electroluminescent device. As shown in FIG. 1, the organic electroluminescent device can comprise an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic light-emitting layer 330, an electron transport layer 340, and a cathode 200 arranged in sequence.

[0063] In a particular embodiment, the organic electroluminescent device is a blue organic electroluminescent device.

[0064] Optionally, the anode 100 comprises an anode material, which is optionally a material with a large work function (work function) that facilitates hole injection into the functional layer. Specific examples of the anode material 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, the transparent electrode comprises an anode comprising indium tin oxide (ITO).

[0065] Optionally, the hole transport layer 321 comprises one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, which can be selected by those skilled in the art with reference to the prior art. For example, the material of the hole transport layer is selected from the group consisting of the following compounds:

[0066] In one specific embodiment, the hole transport layer 321 is HT-20.

[0067] Optionally, the electron blocking layer 322 comprises one or more electron blocking materials, which can be selected from carbazole polymers or other types of compounds, which are not specifically limited in the present application. In one specific embodiment, the electron blocking layer 322 is SiCzCz.

[0068] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting layer material, or can comprise a host material and a dopant material. Optionally, the organic light-emitting layer 330 is composed of a host material and a dopant material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 can recombine to form excitons in the organic light-emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the dopant material, and the dopant material is capable of emitting light.

[0069] The host material of the organic light-emitting layer 330 can be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not specifically limited in the present application. The host material can be a single host material, or can be a mixed host material.

[0070] In one embodiment of the present application, the host material of the organic light-emitting layer 330 is a compound BH-N and the organic compound of the present application.

[0071] The dopant material of the organic light-emitting layer 330 can be selected according to the prior art, for example, can be selected from iridium (III) organometallic complex, platinum (II) organometallic complex, ruthenium (II) complex, etc. Specific examples of the dopant material include, but are not limited to,

[0072] In an embodiment of the present application, the dopant material of the organic light-emitting layer 330 is BD.

[0073] 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, which can generally include metal complex and / or nitrogen-containing heterocyclic derivatives, wherein the metal complex material can be selected from LiQ, Alq3, Bepq2, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring with a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound with 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 ET-21, Bphen, NBphen, DBimiBphen, BimiBphen, or nitrogen-containing heteroaryl anthracene compounds, triazine compounds or pyrimidine compounds with the following structure. In an embodiment of the present application, the electron transport layer 340 is composed of ET-21 and LiQ.

[0074] In the present application, the cathode 200 can include a cathode material, which is a material with small work function that helps electron injection material into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or their alloys; or multi-layer 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 included as the cathode.

[0075] Optionally, as shown in FIG. 1, a hole injection layer 310 can also be provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from diphenylamine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specially limited in the present application. For example, the hole injection layer 310 contains a compound selected from the group consisting of the following compounds:

[0076] In a specific embodiment of the present application, the hole injection layer 310 is HT-20 and PD-1.

[0077] Optionally, as shown in FIG. 1, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability of injecting electrons into the electron transport layer 340. The electron injection layer 350 can include inorganic materials such as alkali metal sulfides, alkali metal halides, or can include complexes of alkali metals and organic substances. In one specific embodiment of the present application, the electron injection layer 350 is Yb.

[0078] The third aspect of the present application provides an electronic device comprising the electronic element provided by the second aspect of the present application.

[0079] According to one embodiment, as shown in FIG. 2, the electronic device is a first electronic device 400 comprising the organic electroluminescent device described above. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. The synthesis method of the organic compound of the present application will be specifically described below in combination with a synthesis example, but the present application is not limited in any way by this.

[0080] The compounds of the present application not mentioned in the synthesis method are all raw material products obtained by commercial channels.

[0081] 1. Synthesis of intermediate Sub-a:

[0082] Under a nitrogen atmosphere, 3,9'-bicarbazole (20.00 g, 60.17 mmol), m-bromophenylboronic acid (12.08 g, 60.17 mmol) and 200 mL of toluene were sequentially added to a 500 mL three-necked flask, which was then warmed to 110°C and condensed to reflux for 1 h. The temperature was then lowered to 90°C, and sodium tert-butoxide (8.76 g, 90.26 mmol), S-phos (0.49 g, 1.20 mmol) and Pd2(dba2)3(0.55 g, 0.60 mmol) were sequentially added, and the reaction was warmed to 110°C and condensed to reflux for 10 h. After the temperature of the system was lowered to room temperature, the reaction solution was poured into 1000 mL of deionized water, extracted with toluene, dried with anhydrous sodium sulfate, and concentrated to obtain the crude product. The crude product was then subjected to silica gel column chromatography using toluene as the eluent to remove inorganic salts and excess catalyst and other impurities, and concentrated by rotary evaporation to obtain the crude product. The crude product was recrystallized with n-heptane / dichloromethane to obtain the intermediate Sub-a (20.41 g, yield 75%) as a white solid.

[0083] 2. Synthesis of intermediate Sub-b:

[0084] Into a 500 mL three-necked flask, 1-chloro-2, 6-dibromobenzene (20.00 g, 73.98 mmol), deuterated trifluoromethanesulfonic acid (20.00 g, 132.38 mmol) and deuterated benzene (200 mL) were sequentially added under nitrogen atmosphere, and the reaction was stirred at 50 °C to reflux for 10 h. After the temperature of the system dropped to room temperature, the reaction solution was neutralized with aqueous sodium bicarbonate solution until it was neutral, 200 mL of deionized water was added and stirred for 5 min, and the organic phase was separated and extracted with dichloromethane (200 mL x 3). The obtained organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the intermediate Sub-b as a white solid (18.32 g, yield 90.6%).

[0085] 3. Synthesis of intermediate Sub-b1:

[0086] Into a 500 mL three-necked flask, 1-chloro-2, 6-dibromobenzene (20.00 g, 73.98 mmol), deuterated trifluoromethanesulfonic acid (20.00 g, 132.38 mmol) and deuterated benzene (200 mL) were sequentially added under nitrogen atmosphere, and the reaction was stirred at 50 °C to reflux for 10 h. After the temperature of the system dropped to room temperature, the reaction solution was neutralized with aqueous sodium bicarbonate solution until it was neutral, 200 mL of deionized water was added and stirred for 5 min, and the organic phase was separated and extracted with dichloromethane (200 mL x 3). The obtained organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the intermediate Sub-b as a white solid (18.32 g, yield 90.6%).

[0087] The intermediates Sub-bx (x is 4-21) shown in Table 1 were synthesized according to the method of intermediate Sub-b1, except that reactant A was used instead of 1-chloro-2, 6-dibromobenzene, and reactant B was used instead of 2-biphenylboronic acid. The main raw materials used, the intermediates synthesized, and their yields are shown in Table 1.

[0088] Table 1

[0089] 4. Synthesis of intermediate Sub-c1:

[0090] Into a 500 mL three-necked flask, were added sequentially intermediate Sub-b1 (20.00 g, 58.20 mmol), 1-boronic acid dibenzofuran (13.58 g, 64.02 mmol), potassium carbonate (20.08 g, 145.5 mmol), tetrakis(triphenylphosphine)palladium (0.34 g, 0.30 mmol), toluene (200 mL), ethanol (100 mL) and water (20 mL) under nitrogen atmosphere, the reaction mixture was heated to 100 °C to reflux and stirred for 4 h. After the temperature of the system was decreased to room temperature, 200 mL of deionized water was added and stirred for 5 min, the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3), the combined organic phase was dried over anhydrous sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as eluent to give intermediate Sub-c1 (15.05 g, yield 60%) as a white solid.

[0091] The intermediates Sub-cx (x is 2-40) shown in Table 2 were synthesized according to the method of intermediate Sub-c1, except that the reactant C was used instead of Sub-b1 and the reactant D was used instead of 1-boronic acid dibenzofuran, wherein the main raw materials used, the intermediates synthesized and their yields are shown in Table 2.

[0092] Table 2

[0093] Synthesis Example 1: Synthesis of compound 5

[0094] Into a 250 mL three-necked flask, were added sequentially Sub-a (10.00 g, 22.11 mmol), Sub-c19 (9.53 g, 22.11 mmol), potassium carbonate (7.63 g, 55.28 mmol), tetrakis(triphenylphosphine)palladium (0.13 g, 0.11 mmol), toluene (200 mL), ethanol (100 mL) and water (20 mL) under nitrogen atmosphere, the reaction mixture was heated to 100 °C to reflux and stirred for 4 h. After the temperature of the system was decreased to room temperature, 200 mL of deionized water was added and stirred for 5 min, the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3), the combined organic phase was dried over anhydrous sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as eluent to give compound (12.43 g, yield 70%) as a white solid; mass (m / z) = 803.3 [M+H] + .

[0095] The compounds shown in Table 3 were synthesized by referring to the method of compound 5, except that reactant E was used instead of Sub-c19. The main raw materials used, the synthesized compounds, their mass spectra and yields are shown in Table 3.

[0096] Table 3

[0097] NMR data of compound 1: 1 H-NMR(400MHz,MethyleneChloride-d2)δppm8.55(d,2H),8.19(d,2H),8.06(d,2H),7.94-7.96(m,4H),7.35-7.79(m,23H),7.16-7.20(m,3H).

[0098] NMR data of compound 5: 1 H-NMR(400MHz,MethyleneChloride-d2)δppm8.55(d,2H),8.19(d,2H),7.94-8.08(m,9H),7.31-7.79(m,22H),7.16-7.20(m,3H).

[0099] Example 1: Blue organic electroluminescent device

[0100] 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.

[0101] On the experimental substrate (anode), compounds HT-20 and PD-1 were co-evaporated at an evaporation rate ratio of 98%:2% to form a film with a thickness of hole injection layer.

[0102] On the hole injection layer, compound HT-20 was evaporated to form a layer with a thickness of hole transport layer.

[0103] On the hole transport layer, the compound SiCzCz is evaporated to form a layer with a thickness of electron blocking layer.

[0104] On the electron blocking layer, compound 1, BH-N and BD were co-evaporated at a rate ratio of 60%:40%:10% to form an organic light-emitting layer with a thickness of .

[0105] On the organic light-emitting layer, compound ET-21 and LiQ were co-evaporated at a rate ratio of 50%:50% to form an electron transport layer with a thickness of .

[0106] On the electron transport layer, Yb was evaporated to form an electron injection layer with a thickness of . Then, on the electron injection layer, magnesium (Mg) and silver (Ag) were co-evaporated at a rate ratio of 10%:90% to form a cathode with a thickness of .

[0107] In addition, on the cathode, compound CP-1 was evaporated to form an organic capping layer with a thickness of , thereby completing the preparation of the blue organic electroluminescent device.

[0108] Examples 2-36

[0109] An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound in Table 4 below was used instead of compound 1 in Example 1 when forming the organic light-emitting layer.

[0110] Comparative Examples 1-4

[0111] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B, compound C and compound D were used instead of compound 1 in Example 1, respectively, when forming the organic light-emitting layer.

[0112] In the preparation of each of the examples and comparative examples, the compounds used had the following structures:

[0113] The blue organic electroluminescent devices prepared in Examples 1-36 and Comparative Examples 1-4 were tested for performance, and the voltage, efficiency and lifetime characteristics of the devices were tested at a brightness of 1000 nit, and the test results are shown in Table 4.

[0114] Table 4

[0115] As can be seen from Table 4 above, when the compounds of the present application are used as the host material of a blue organic electroluminescent device, the efficiency is at least 12.3% higher and the lifetime is at least 13.1% longer compared to the compounds of Comparative Examples 1-4.

[0116] The preferred embodiments of the present application are described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above-described embodiments. Various simple modifications can be made to the technical solutions of the present application within the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

[0117] In addition, it should be noted that each specific technical feature described in the above specific embodiments can be combined in any appropriate manner without contradiction. In order to avoid unnecessary repetition, various possible combinations are not described again in the present application.

Claims

1. Organic compound, characterized in that, The organic compound has a structure shown in Formula 1: wherein each R1is the same or different and each is independently selected from hydrogen or deuterium; Ar is selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 30, a substituted or unsubstituted O- or S-containing heteroaryl group having a carbon number of 3 to 30; each R2is the same or different and each is independently selected from hydrogen, a substituted or unsubstituted aryl group having a carbon number of 6 to 30, a substituted or unsubstituted O- or S-containing heteroaryl group having a carbon number of 3 to 30; the substituents in Ar and R2are the same or different and each is independently selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having a carbon number of 3 to 12, a haloalkyl group having a carbon number of 1 to 10, an alkyl group having a carbon number of 1 to 10, an aryl group having a carbon number of 6 to 20, or an O- or S-containing heteroaryl group having a carbon number of 5 to 20; m represents the number of R1, and m is selected from 1, 2, or 3; when m is greater than 1, any two R1are the same or different; n represents the number of R2, and n is selected from 1, 2, 3, 4, or 5; when n is greater than 1, any two R2are the same or different.

2. The organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 25, a substituted or unsubstituted O- or S-containing heteroaryl group having a carbon number of 12 to 18; optionally, the substituents in Ar are the same or different and each is independently selected from deuterium, fluorine, a cyano group, a trialkylsilyl group having a carbon number of 3 to 6, a haloalkyl group having a carbon number of 1 to 5, an alkyl group having a carbon number of 1 to 5, an aryl group having a carbon number of 6 to 12, or an O- or S-containing heteroaryl group having a carbon number of 5 to 12.

3. The organic compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; optionally, the substituents in Ar are the same or different and each is independently selected from deuterium, fluorine, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

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

5. The organic compound according to claim 1, wherein each R2is the same or different and each is independently selected from hydrogen, a substituted or unsubstituted aryl group having a carbon number of 6 to 25, a substituted or unsubstituted O- or S-containing heteroaryl group having a carbon number of 12 to 18; optionally, the substituents in R2are the same or different and each is independently selected from deuterium, fluorine, a cyano group, a trialkylsilyl group having a carbon number of 3 to 6, a haloalkyl group having a carbon number of 1 to 5, an alkyl group having a carbon number of 1 to 5, an aryl group having a carbon number of 6 to 12, or an O- or S-containing heteroaryl group having a carbon number of 5 to 12.

6. The organic compound according to claim 1, wherein each R2is the same or different and each is independently selected from hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; Optionally, the substituents in R2 are the same or different, and each is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.

7. The organic compound according to claim 1, wherein each R2is the same or different and each is independently selected from the group consisting of hydrogen or:

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

9. An electronic component, characterized by The electronic element comprises oppositely arranged anode and cathode, and a functional layer arranged between the anode and the cathode; wherein the functional layer comprises the organic compound in any one of claims 1-8.

10. The electronic component of claim 9, wherein, The functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound. Optionally, the electronic element is an organic electroluminescent device.

11. An electronic device, characterized by The electronic device comprises the electronic element of claim 9 or 10.

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