Organic compound, electronic element and electronic device

Abstract

The invention relates to an organic compound, an electronic element, and an electronic device. The organic compound provided by the invention has a structure as shown in the formula I. When the organic compound is applied to an electronic element, the performance of the device can be remarkably improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic electroluminescence, in particular to an organic compound, an electronic element and an electronic device. BACKGROUND

[0002] An organic electroluminescence phenomenon refers to a phenomenon of converting electrical energy into light energy by using an organic substance. An organic electroluminescence display device generates excitons through the transfer and recombination of carriers between various functional layers, and relies on high quantum efficiency organic compounds or metal complexes to emit light. Among them, as a new generation of display technology, an organic light-emitting diode (OLED) has been increasingly applied in people's daily life, such as smart phones, smart watches, portable notebooks, etc. These daily use equipment all use OLED display technology. Compared with other display technologies, OLED technology has the advantages of wide viewing angle, fast response speed, low driving voltage, wide display temperature range, full-color display in the blue to red spectral region, etc.

[0003] The structure of an OLED element generally includes an anode, a cathode, and an organic functional layer therebetween. In order to improve the efficiency and life of the OLED element, the organic functional layer generally has a multi-layer structure, such as a hole injection layer, a hole transport layer, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, etc. These different functional layers all contain different organic substances. Among them, the organic hole transport material applied to the hole transport layer plays an important role in transferring the holes injected from the anode to the light-emitting layer. On the one hand, a hole transport material with excellent hole mobility is conducive to the injection balance of carriers in the device, thereby achieving a reduced device driving voltage. On the other hand, since the excitons generated in the organic light-emitting layer move to the hole transport layer, eventually causing light emission at the interface between the hole transport layer and the light-emitting layer, resulting in color deviation and reduced light-emitting efficiency. Therefore, in order to improve the efficiency of the light-emitting layer as much as possible, prevent efficiency roll-off, and improve the stability of the device, it is crucial to design a reasonable functional layer structure and design and match new high-performance organic compound materials. SUMMARY

[0004] The purpose of the present application is to provide an organic compound, an electronic element and an electronic device, and the use of the organic compound in an organic electroluminescence device can improve the performance of the device.

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

[0006]

[0007] wherein R is selected from substituted or unsubstituted alkyl having a carbon number of 1-10;

[0008] each L is identical or different, and each is independently selected from a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 40 carbon atoms;

[0009] n is the number of L groups connected in series, and n is selected from 1, 2, or 3;

[0010] L1and L2are identical or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 40 carbon atoms;

[0011] Ar1and Ar2are identical or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;

[0012] the substituents in R are identical or different, and each is independently selected from deuterium, a halogen group, a cyano group;

[0013] the substituents in L, L1, L2, Ar1, and Ar2are identical or different, and each is 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 halogenated alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a deuterated heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, or a triarylsilyl group having 18 to 24 carbon atoms.

[0014] A 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] A third aspect of the present application provides an electronic device comprising the electronic element described in the second aspect.

[0016] The core structure of the organic compound of the present application is that the 2,2-position of adamantyl is simultaneously connected with arylamine groups and alkyl groups. This connection, on the one hand, effectively reduces the overall symmetry of the molecule while increasing the molecular weight, so that the glass transition temperature is higher, the molecular rigidity is reduced, the film-forming property of the molecule is significantly improved, the evaporation form is more excellent, and the service life of the material is significantly prolonged. On the other hand, the triarylamine compound designed by the present application has the structural feature that the 2,2-position of adamantyl is simultaneously connected with alkyl and arylamine groups. Due to the connection of the small-volume alkyl substituent and the conjugated arylamine substituent through the same carbon atom, the area of the non-conjugated region in the molecule is increased, and the rigidity of the molecule is effectively improved. The organic compound of the present application is used for preparing an OLED device, and the compound can quickly respond when the device is working, adjust the balance of hole transmission and injection, avoid the formation of hole transmission traps, so that the device has higher light-emitting efficiency and service life.

[0017] Other features and advantages of the present application will be described in detail in the following specific embodiments. BRIEF DESCRIPTION OF DRAWINGS

[0018] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used together with the following specific embodiments to explain the present application, but do not constitute a limitation on the present application.

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

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

[0021] Figure 3 is a structural schematic diagram of a photoelectric conversion device according to an embodiment of the present application.

[0022] Figure 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.

[0023] EXPLANATION OF REFERENCE NUMERALS

[0024] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0025] 320, hole transport layer 321, light-emitting adjustment layer 330, organic light-emitting layer 340, electron transport layer

[0026] 350, electron injection layer 360, photoelectric conversion layer 400, first electronic device 500, second electronic device DETAILED DESCRIPTION

[0027] Example implementations will now be described more fully with reference to the accompanying drawings. Example implementations, however, can be implemented in many different forms and should not be construed as limited to the examples set forth herein; rather, these implementations are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the example implementations to those skilled in the art. The described features, structures, or characteristics can be combined in one or more implementations. In the following description, numerous specific details are provided to give a thorough understanding of implementations of the application.

[0028] In the present application, the description "each of... is independently" and "each of... is independently" and "each of... is independently" can be interchangeable, and should be interpreted broadly, which can mean that the specific options expressed by the same symbols in different groups do not affect each other, or can mean that the specific options expressed by the same symbols in the same group do not affect each other. For example, "each of R1 and R2 is independently selected from the group consisting of hydrogen, deuterium, halogen, and cyano" can mean that R1 and R2 are independently selected from the group consisting of hydrogen, deuterium, halogen, and cyano, or R1 and R2 are independently selected from the group consisting of hydrogen, deuterium, and cyano. 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 independent of each other; formula Q-2 represents that there are q substituents R" on each benzene ring of the biphenyl, the number 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 independent of each other.

[0029] In the present application, the term "substituted or unsubstituted" means that the functional groups described after the term can have or not have substituents (hereinafter, the substituents will be collectively referred to as Rc for ease of description). For example, "substituted or unsubstituted aryl" means aryl with substituents Rc or aryl without substitution. The above-mentioned substituents, i.e., Rc, for example, can be deuterium, a halogen group, a cyano group, an alkyl group, a deuterated alkyl group, a halogenated alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, a deuterated aryl group, a deuterated heteroaryl group, a trialkylsilyl group, a triaryl silyl group, and the like. The number of substitutions can be one or more.

[0030] In the present application, the indefinite position connecting bond refers to a single bond extending from the ring system which means that one end of the connecting bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the molecule.

[0031] For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions of the molecule through two indefinite position connecting bonds that pass through the bicyclic ring, and the meaning represented thereby includes any possible connection mode as shown in formula (f-1) to formula (f-10).

[0032]

[0033] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to the rest of the molecule through an unspecified bond extending from the middle of one of the phenyl rings, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (X'-1) to (X'-4).

[0034]

[0035] In the present application, an unspecified substituent refers to a substituent connected through a single bond extending from the center of a ring system, and the meaning represented thereby includes any of the possible connection modes as shown in formulae (Y-1) to (Y-7).

[0036]

[0037] In the present application, the number of carbon atoms of R, L, L1, L2, Ar1, Ar, L3, L4, L5, Ar3, and Ar4 refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene group having a total of 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0038] In the present application, "alkyl" can include straight-chain alkyl groups or branched-chain alkyl groups. Alkyl groups can have 1 to 10 carbon atoms, and in the present application, numerical ranges such as "1 to 10" refer to each integer in the given range; for example, "1 to 10 carbon atoms" means that the alkyl group can contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples thereof include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.

[0039] In the present application, a cycloalkyl group refers to a group derived from a saturated cyclic carbon chain structure. Cycloalkyl groups can have 3 to 10 carbon atoms, and in the present application, numerical ranges such as "3 to 10" refer to each integer in the given range; for example, "5 to 10 carbon atoms" means that the cycloalkyl group can contain 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, or 10 carbon atoms. Alternatively, specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, and the like.

[0040] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorenyl, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthrene, biphenyl, terphenyl, perylene, pyrene, benzofluoranthyl, etc. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40, etc. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0041] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0042] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom may be replaced by a deuterium, halogen group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, deuterated heteroaryl, trialkylsilyl, or triarylsilyl group. It is understood that the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example, Ar1 is... Therefore, it has 10 carbon atoms.

[0043] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, and biphenyl groups.

[0044] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0045] In this application, terphenyl includes

[0046] In the present application, heteroaryl refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms can be at least one of B, O, N, P, Si, Se and S. The heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any aromatic ring system is an aromatic monocyclic ring or an aromatic fused ring. For example, the heteroaryl can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl (such as benz [B] carbazolyl ), benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), N-alkylcarbazolyl (such as N-methylcarbazolyl), spiro (fluorene-9, 9'-xanthene) group xanthene group , and the like, but not limited thereto. Among them, thienyl, furanyl, phenanthrolinyl and the like are single aromatic ring system type heteroaryl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl are polycyclic system type heteroaryl connected by carbon-carbon bonds. For example, in the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc.

[0047] In the present application, the heteroaryl group referred to is a divalent group formed by further losing one hydrogen atom from the heteroaryl group.

[0048] In the present application, the substituted heteroaryl can be one or more hydrogen atoms in the heteroaryl group substituted by groups such as deuterium, halogen group, cyano group, alkyl group, deuterated alkyl group, halogenated alkyl group, cycloalkyl group, aryl group, heteroaryl group, deuterated aryl group, deuterated heteroaryl group, trialkylsilyl group, triarylsilyl group, etc.

[0049] It should be understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and the substituents on the heteroaryl.

[0050] In the present application, specific examples of the heteroaryl group as a substituent include, but are not limited to, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, N-phenylcarbazolyl group, and the like.

[0051] In the present application, "deuterated" means that at least one hydrogen ("H") in a compound or a group is replaced with deuterium ("D"); specifically, a deuterated compound or a deuterated group can be a compound or a group in which one, more, or all available hydrogens have been replaced with deuterium.

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

[0053] In the present application, the haloalkyl group can be an alkyl group in which one or more than two hydrogen atoms are replaced with a halogen atom, and specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl group.

[0054] In the present application, the deuterated alkyl group can be an alkyl group in which one or more than two hydrogen atoms are replaced with deuterium, and specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl group.

[0055] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group.

[0056] In the present application, specific examples of the triarylsilyl group include, but are not limited to, triphenylsilyl group.

[0057] In the present application, the deuterated aryl group can be an aryl group in which one or more than two hydrogen atoms are replaced with deuterium, and specific examples of the deuterated aryl group include, but are not limited to, penta-deuteriophenyl group, hepta-deuteriophenyl group.

[0058] In the present application, the deuterated heteroaryl group can be a heteroaryl group in which one or more than two hydrogen atoms are replaced with deuterium, and specific examples of the deuterated heteroaryl group include, but are not limited to, hepta-deuterodibenzofuranyl group.

[0059] In the first aspect of the present application, an organic compound having a structure represented by Formula I is provided:

[0060]

[0061] wherein R is selected from a substituted or unsubstituted alkyl group having a carbon number of 1 to 10;

[0062] each L is the same or different, and each is independently selected from a substituted or unsubstituted arylene group having a carbon number of 6 to 40, or a substituted or unsubstituted heteroarylene group having a carbon number of 3 to 40;

[0063] n is the number of L groups connected in series, and n is selected from 1, 2, or 3;

[0064] L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having a carbon atom number of 6 to 40, a substituted or unsubstituted heteroarylene group having a carbon atom number of 3 to 40;

[0065] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon atom number of 6 to 40, a substituted or unsubstituted heteroaryl group having a carbon atom number of 3 to 40;

[0066] the substituents in R are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group;

[0067] the substituents in L, L1, L2, Ar1, and Ar2are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon atom number of 1 to 10, a deuterated alkyl group having a carbon atom number of 1 to 10, a halogenated alkyl group having a carbon atom number of 1 to 10, a cycloalkyl group having a carbon atom number of 3 to 10, an aryl group having a carbon atom number of 6 to 20, a heteroaryl group having a carbon atom number of 3 to 20, a deuterated aryl group having a carbon atom number of 6 to 20, a deuterated heteroaryl group having a carbon atom number of 3 to 20, a trialkylsilyl group having a carbon atom number of 3 to 12, or a triarylsilyl group having a carbon atom number of 18 to 24.

[0068] In some embodiments, R is selected from an alkyl group having a carbon atom number of 1 to 5. For example, R is selected from a substituted or unsubstituted alkyl group having a carbon atom number of 1, 2, 3, 4, or 5.

[0069] In some embodiments, R is selected from a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, an i-pentyl group, or a neopentyl group.

[0070] In some embodiments, each L is the same or different, and each is independently selected from a substituted or unsubstituted arylene group having a carbon atom number of 6 to 18. For example, each L is the same or different, and each is independently selected from a substituted or unsubstituted arylene group having a carbon atom number of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.

[0071] Optionally, the substituents in each L are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, an alkyl group having a carbon atom number of 1 to 5, a deuterated alkyl group having a carbon atom number of 1 to 5, a halogenated alkyl group having a carbon atom number of 1 to 5, an aryl group having a carbon atom number of 6 to 12, a deuterated aryl group having a carbon atom number of 6 to 12, or a trialkylsilyl group having a carbon atom number of 3 to 9.

[0072] In some embodiments, each L is the same or different, and each is independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group.

[0073] Optionally, the substituents in each L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, pentadeuterated phenyl or trimethylsilyl.

[0074] In some implementations... Selected from the group consisting of the following groups:

[0075]

[0076] In some implementations... Selected from the group consisting of the following groups:

[0077]

[0078] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms. For example, L1 and L2 may be the same or different, and each is independently selected from single-bonded substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0079] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms.

[0080] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted carbazolylene.

[0081] Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, pentadeuterated phenyl or trimethylsilyl.

[0082] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0083]

[0084] In some embodiments, L1and L2are the same or different and each is independently selected from the group consisting of a single bond or:

[0085]

[0086]

[0087] In some embodiments, Ar1and Ar2are the same or different and each is independently selected from a substituted or unsubstituted aryl group having a carbon atom count of 6 to 25, a substituted or unsubstituted heteroaryl group having a carbon atom count of 12 to 25. For example, Ar1and Ar2are the same or different and each is independently selected from a substituted or unsubstituted aryl group having a carbon atom count of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25, a substituted or unsubstituted heteroaryl group having a carbon atom count of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25.

[0088] Optionally, the substituents in Ar1and Ar2are the same or different and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon atom count of 1 to 5, a haloalkyl group having a carbon atom count of 1 to 5, a deuterated alkyl group having a carbon atom count of 1 to 5, a trialkylsilyl group having a carbon atom count of 3 to 8, an aryl group having a carbon atom count of 6 to 12, a deuterated aryl group having a carbon atom count of 6 to 12.

[0089] In some embodiments, Ar1and Ar2are the same or different and each is independently 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 phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted group:

[0090] Optionally, the substituents in Ar1and Ar2are the same or different and each is independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a phenyl group, a naphthyl group, a biphenyl group, a penta-deuterophenyl group.

[0091] In some embodiments, Ar1and Ar2are the same or different and each is independently selected from the group consisting of:

[0092]

[0093] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from the group consisting of:

[0094]

[0095]

[0096] In some embodiments, the same or different, and each is independently selected from the group consisting of:

[0097]

[0098]

[0099] In some embodiments, the same or different, and each is independently selected from the group consisting of:

[0100]

[0101]

[0102]

[0103] In particular, the organic compound represented by Formula I is selected from the group consisting of the compounds as shown in claim 8.

[0104] 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.

[0105] Optionally, the functional layer of the electronic element comprises an emission adjusting layer, and the emission adjusting layer comprises the organic compound of the present application.

[0106] Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.

[0107] The electronic element provided by the present application further comprises a hole transport layer in the functional layer, and the hole transport layer comprises a carbazole compound represented by Formula II:

[0108]

[0109] wherein L3, L4and L5are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms.

[0110] ​Ar3and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 30, a substituted or unsubstituted heteroaryl group having a carbon number of 3 to 30;

[0111] the substituents in L3, L4, L5, Ar3, and Ar4are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon number of 1 to 10, a deuterated alkyl group having a carbon number of 1 to 10, a halogenated alkyl group having a carbon number of 1 to 10, a cycloalkyl group having a carbon number of 3 to 10, an aryl group having a carbon number of 6 to 20, a heteroaryl group having a carbon number of 3 to 20, a trialkylsilyl group having a carbon number of 3 to 12, or a triarylsilyl group having a carbon number of 18 to 24;

[0112] each R1, each R2, and each R3are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon number of 1 to 10, a deuterated alkyl group having a carbon number of 1 to 10, a halogenated alkyl group having a carbon number of 1 to 10, an aryl group having a carbon number of 6 to 20, a heteroaryl group having a carbon number of 3 to 20, a deuterated aryl group having a carbon number of 6 to 20, or a deuterated heteroaryl group having a carbon number of 3 to 20;

[0113] n1 is the number of R1, and n1 is selected from 0, 1, 2, 3, or 4;

[0114] n2 is the number of R2, and n2 is selected from 0, 1, 2, or 3;

[0115] n3 is the number of R3, and n3 is selected from 0, 1, 2, 3, 4, or 5.

[0116] In some embodiments, L3, L4, and L5are the same or different, and each is independently selected from a single bond, or a substituted or unsubstituted arylene group having a carbon number of 6 to 18. For example, L3, L4, and L5are the same or different, and each is independently selected from a single bond, or a substituted or unsubstituted arylene group having a carbon number of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.

[0117] Alternatively, the substituents in L3, L4, and L5are the same or different, and each is independently selected from deuterium, a halogen group, a cyano group, an alkyl group having a carbon number of 1 to 5, a halogenated alkyl group having a carbon number of 1 to 5, a deuterated alkyl group having a carbon number of 1 to 5, a phenyl group, or a trimethylsilyl group.

[0118] In some embodiments, L3, L4, and L5are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

[0119] Optionally, the substituents in L3, L4, and L5 are the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, trideuteromethyl, methyl, ethyl, isopropyl, tert-butyl, or phenyl.

[0120] In some embodiments, L3, L4, and L5 are the same or different, and each is independently selected from a single bond or a group consisting of:

[0121]

[0122] In some embodiments, L3, L4, and L5 are the same or different, and each is independently selected from a single bond or a group consisting of:

[0123]

[0124] In some embodiments, Ar3and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6 to 25, or a substituted or unsubstituted heteroaryl group having a carbon number of 12 to 18. For example, Ar3and Ar4are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having a carbon number of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25, a substituted or unsubstituted heteroaryl group having a carbon number of 12, 13, 14, 15, 16, 17, or 18.

[0125] Optionally, the substituents in Ar3and Ar4are the same or different, and each is independently selected from deuterium, a halogen group, cyano, an alkyl group having a carbon number of 1 to 5, a haloalkyl group having a carbon number of 1 to 5, a deuterated alkyl group having a carbon number of 1 to 5, a trialkylsilyl group having a carbon number of 3 to 8, an aryl group having a carbon number of 6 to 12, a heteroaryl group having a carbon number of 5 to 12.

[0126] In some embodiments, Ar3and Ar4are the same or different, and each is independently 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 phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0127] Optionally, the substituents in Ar3and Ar4are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl, or carbazolyl.

[0128] In some embodiments, Ar3 and Ar4 may be the same or different, and each is independently selected from the following groups:

[0129]

[0130] In some embodiments, Ar3 and Ar4 may be the same or different, and each is independently selected from the group consisting of:

[0131]

[0132]

[0133] In some implementations, in Formula II Each group is independently selected from the group consisting of the following groups:

[0134]

[0135] Specifically, in Formula II Each group is independently selected from the group consisting of the following groups:

[0136]

[0137]

[0138] In some embodiments, each R1, each R2, and each R3 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, and deuterated aryl with 6 to 12 carbon atoms.

[0139] In some embodiments, each of R1, each of R2 and each of R3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n-butyl, trifluoromethyl, trideuterated methyl, phenyl, pentadeuterated phenyl, naphthyl or biphenyl.

[0140] Specifically, the carbazole compounds represented by Formula II are selected from the group consisting of the compounds shown in claim 13.

[0141] In this application, the organic electroluminescent device can be a blue organic electroluminescent device, a red organic electroluminescent device, or a green organic electroluminescent device.

[0142] Alternatively, the organic electroluminescent device may be a red-light organic electroluminescent device.

[0143] In one embodiment, the electronic component is an organic electroluminescent device, such as... Figure 1As shown, the organic electroluminescent device can include an anode 100, a hole transport layer 320, an emission adjusting layer 321, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are arranged in a stack.

[0144] Optionally, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include a metal such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; or a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but is not limited thereto. Preferably, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0145] Optionally, the hole transport layer includes one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds.

[0146] In one specific embodiment, the hole transport layer 320 is a carbazole compound as shown in Formula II of the present application.

[0147] In one specific embodiment, the emission adjusting layer 321 is an organic compound as shown in Formula I of the present application.

[0148] Optionally, the organic light emitting layer 330 can be composed of a single light emitting layer material, or can include a host material and a guest material. Optionally, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 can recombine to form an exciton in the organic light emitting layer 330, the exciton transfers energy to the host material, the host material transfers energy to the guest material, and the guest material emits light.

[0149] 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 particularly limited by the present application. The host material can be a single host material, or a mixed host material.

[0150] In one specific embodiment, the host material of the organic light emitting layer 330 is composed of p-RH-1 and n-RH-1 .

[0151] The guest material of the organic light-emitting layer 330 can be selected according to the prior art, for example, can be selected from iridium (III) organic metal complex, platinum (II) organic metal complex, ruthenium (II) complex, etc. Specific examples of the guest material include but are not limited to:

[0152]

[0153] In one specific embodiment, the guest material of the organic light-emitting layer 330 is RD-1.

[0154] 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 complexes or / and nitrogen-containing heterocyclic derivatives, wherein the metal complex material can be selected from LiQ, Alq3, 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 Bphen, NBphen, ET-1, BimiBphen, etc., or anthracene compounds, triazine compounds or pyrimidine compounds containing heteroaromatic groups with the following structures. Specific examples of nitrogen-containing heterocyclic derivatives used in electron transport materials include but are not limited to:

[0155]

[0156]

[0157] In one specific embodiment, the electron transport layer 340 is composed of ET-1 and LiQ.

[0158] In this 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.

[0159] Optionally, as shown in Figure 1 a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specially limited in this application. For example, the hole injection layer 310 contains a compound selected from the following group of compounds:

[0160]

[0161] In one specific embodiment, the hole injection layer 310 is composed of a carbazole compound represented by Formula II of this application and PD-1.

[0162] Optionally, such as Figure 1 As shown, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. For example, the electron injection layer 350 includes ytterbium (Yb).

[0163] Optionally, the cathode 200 also has an organic coating layer.

[0164] In one specific embodiment, the organic coating layer comprises compound CP-1.

[0165] In another implementation, the electronic component is a photoelectric conversion device. For example... Figure 3 As shown, the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the organic compound provided in this application.

[0166] According to a specific implementation method, such as Figure 3 As shown, the photoelectric conversion device includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340, and a cathode 200, which are stacked sequentially. Optionally, the hole transport layer 320 contains the organic compound of this application.

[0167] Optionally, the photoelectric conversion device can be a solar cell, especially an organic thin-film solar cell. For example, in one embodiment of this application, the solar cell includes an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode stacked sequentially, wherein the hole transport layer contains the organic compound of this application.

[0168] Thirdly, this application provides an electronic device including the electronic components provided in the second aspect of this application.

[0169] According to one implementation method, such as Figure 2As shown, the electronic device is a first electronic device 400, which includes the aforementioned organic electroluminescent device. The first electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0170] According to another implementation method, such as Figure 4 As shown, the electronic device is a second electronic device 500, which includes the aforementioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a photodetector, a fingerprint recognition device, an optical module, a CCD camera, or other types of electronic devices.

[0171] The following examples illustrate the synthesis methods of the organic compounds described in this application, but this application is not limited in any way as a result.

[0172] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0173] Synthesis example

[0174] 1. Synthesis of the organic compound shown in Formula I

[0175] 1.1 Synthesis of intermediate IN-AdP-01

[0176]

[0177] Under nitrogen protection, 2-hydroxy-2-methyladamantane (120.0 g, 721.76 mmol), bromobenzene (139.4 g, 887.77 mmol), and dry dichloromethane (CH2Cl2, 1200 mL) were added to a reaction flask. The mixture was stirred and the system temperature was controlled at -5℃ to 0℃ using a circulating cold bath. Concentrated sulfuric acid (98 wt%, 212.35 g, 2165.29 mmol) was slowly added dropwise. The mixture was stirred and kept at this temperature for 4 h. Then, the temperature was naturally raised to room temperature. The reaction solution was washed with water until neutral. The organic phases were combined after separation and purified by silica gel column chromatography to obtain intermediate IN-AdP-01 (150.7 g, yield: 68.4%).

[0178] 1.2 Synthesis of intermediate IN-AdP-x

[0179] IN-AdP-x in Table 1 was synthesized using the same method as IN-AdP-01, with the difference that 2-hydroxy-2-methyladamantane was replaced by reactant 1, and bromobenzene was replaced by reactant 2. The main reactants used, the intermediates synthesized, and their yields are listed in Table 1.

[0180] Table 1

[0181]

[0182]

[0183] 1.3 Synthesis of intermediate IN-AdP-07:

[0184]

[0185] Under nitrogen protection, IN-AdP-01 (10.0 g, 32.76 mmol), 4-chlorophenylboronic acid (5.4 g, 34.53 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.80 g, 0.69 mmol), tetrabutylammonium bromide (TBAB, 2.11 g, 6.55 mmol), potassium carbonate (K2CO3, 9.96 g, 72.07 mmol), toluene (PhMe, 100 mL), ethanol (EtOH, 50 mL), and water (20 mL) were added to the reaction flask. After the addition was complete, stirring was started, and the mixture was heated to 70-75 °C and refluxed for 6 h. The reaction was then stopped, cooled to room temperature, extracted with dichloromethane, and the organic phase was washed with water until neutral. The solution was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The solution was purified by recrystallization from toluene / petroleum ether and dried to give a white solid intermediate IN-AdP-07 (9.2 g, yield: 83.4%).

[0186] 1.4 Synthesis of intermediate IN-AdP-y

[0187] IN-AdP-y in Table 2 was synthesized using the same method as IN-AdP-07, with the difference that raw material 3 was used instead of IN-AdP-01, and raw material 4 was used instead of 4-chlorophenylboronic acid. The main raw materials used, the intermediates synthesized, and their yields are listed in Table 2.

[0188] Table 2

[0189]

[0190]

[0191] 1.5 Synthesis of intermediate IN-NH-1:

[0192]

[0193] Under nitrogen protection, 2-bromo-9-([1,1'-biphenyl]-4-yl)carbazole (8.0 g, 20.08 mmol), 4-aminobiphenyl (3.57 g, 21.09 mmol), tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.37 g, 0.40 mmol), and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-PhOS, 0.38 g, 0.8 mmol) were added to the reaction flask. 0 mmol), sodium tert-butoxide (t-BuONa, 2.9 g, 30.17 mmol) and toluene (70 mL) were added, stirred, and heated to 108 °C for 2 h. The mixture was then cooled to room temperature, washed with water, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain a yellow solid crude product. The crude product was then purified by recrystallization using toluene / petroleum ether to obtain intermediate IN-NH-1 (7.9 g, yield: 80.9%).

[0194] 1.6 Synthesis of intermediate IN-NH-x

[0195] The method for preparing IN-NH-1 was used to synthesize IN-NH-x in Table 3, with the following differences: 2-bromo-9-([1,1'-biphenyl]-4-yl)carbazole was replaced with raw material 5, and 4-aminobiphenyl was replaced with raw material 6. The main raw materials used, the intermediates synthesized, and their yields are listed in Table 3.

[0196] Table 3

[0197]

[0198]

[0199]

[0200] 1.7 Synthesis Example 1: Preparation of Compound 9

[0201]

[0202] Under nitrogen protection, IN-AdP-01 (4.0 g, 13.10 mmol), IN-NH-1 (6.38 g, 13.10 mmol), tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.24 g, 0.26 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-PhOS, 0.22 g, 0.53 mmol), sodium tert-butoxide (1.9 g, 19.66 mmol), and toluene (50 mL) were added to a reaction flask. Stirring was started, and the mixture was heated to 108 °C for 4 h. After cooling to room temperature, the reaction solution was washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain a yellow crude solid. The crude solid was then purified by recrystallization from toluene / petroleum ether to obtain compound 9 (4.99 g, yield: 53.6%). Mass spectrometry (m / z) = 711.4 [M+H] + .

[0203] 1.8 Synthesis Example 2 to Synthesis Example 39:

[0204] The compounds listed in Table 4 were prepared using the same synthetic method as compound 9, except that reactant 7 was used instead of IN-AdP-01, and reactant 8 was used instead of IN-NH-1. The main reactants used, the synthesized compounds, their yields, and mass spectra are listed in Table 4.

[0205] Table 4

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] 2. Synthesis of carbazole compounds shown in Formula II 2.1 Synthesis of intermediate IN-Cz-01-b

[0212]

[0213] Under nitrogen protection, Sub-9HCz-01 (30.0 g, 93.11 mmol), iodobenzene (20.0 g, 98.04 mmol), tris(dibenzylacetone)palladium (1.7 g, 1.86 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.53 g, 3.72 mmol), sodium tert-butoxide (1.9 g, 19.66 mmol), and toluene (50 mL) were added to a reaction flask. Stirring was started, and the mixture was heated to 70–75 °C and refluxed for 6 h. The reaction was stopped, cooled to room temperature, and extracted with dichloromethane. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was purified by recrystallization from toluene / petroleum ether and dried to give a yellow solid intermediate IN-Cz-01-b (29.0 g, yield: 78.2%).

[0214] 2.2 Synthesis of intermediates IN-Cz-02-b and IN-Cz-03-b

[0215]

[0216] Under nitrogen protection, Sub-Cz-03 (15.0 g, 33.47 mmol), 1-naphthylboronic acid (5.8 g, 33.68 mmol), tetra(triphenylphosphine)palladium (0.77 g, 0.67 mmol), tetrabutylammonium bromide (TBAB, 2.2 g, 6.83 mmol), potassium carbonate (10.2 g, 73.81 mmol), toluene (150 mL), ethanol (70 mL), and water (35 mL) were added to a reaction flask. Stirring was started, and the mixture was heated to 70–75 °C and refluxed for 6 h. The reaction was stopped, cooled to room temperature, and extracted with dichloromethane. The organic phase was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The product was purified by recrystallization from toluene / petroleum ether and dried to give a white solid intermediate IN-Cz-03-b (10.1 g, yield: 67.3%).

[0217]

[0218] IN-Cz-03-b was synthesized using the same method as IN-Cz-02-b, except that 1-naphthoboric acid was replaced with deuterated phenylboronic acid, while other conditions remained unchanged, to obtain intermediate IN-Cz-03-b (8.8 g, yield: 66.5%).

[0219] 2.3 Synthesis of intermediate IN-Cz-x

[0220] IN-Cz-z in Table 5 was synthesized using the same method as IN-AdP-07, with the difference that raw material 9 was used instead of IN-AdP-01, and raw material 10 was used instead of 4-chlorophenylboronic acid. The main raw materials used, the intermediates synthesized, and their yields are listed in Table 5.

[0221] Table 5

[0222]

[0223]

[0224] 2.4 Synthesis Example 40: Preparation of Compound H42

[0225]

[0226] Under nitrogen protection, 3-(4-bromophenyl)-9-phenylcarbazole (10.0 g, 25.11 mmol), IN-NH-21 (10.33 g, 25.11 mmol), tris(dibenzylacetone)dipalladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.21 g, 0.50 mmol), sodium tert-butoxide (3.62 g, 37.66 mmol), and toluene (100 mL) were added to a reaction flask. The mixture was stirred and heated to 108 °C for 4 h. After cooling to room temperature, the reaction solution was washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain a yellow crude solid. The crude solid was then purified by recrystallization from toluene / petroleum ether to obtain compound H42 (8.97 g, yield: 49.0%). Mass spectrometry (m / z) = 729.3 [M+H] + .

[0227] 2.5 Synthesis Example 41 to Synthesis Example 52

[0228] The compounds listed in Table 6 were prepared using the same synthetic method as compound H42, with the following differences: starting material 11 was used instead of 3-(4-bromophenyl)-9-phenylcarbazole, and starting material 12 was used instead of IN-NH-21. The main starting materials used, the synthesized compounds, their yields, and mass spectra are listed in Table 6.

[0229] Table 6

[0230]

[0231]

[0232]

[0233] 2.6 Compounds obtained with reference to existing technologies

[0234] Obtained according to the method described in prior art KR1020130106255A; Obtained according to the method described in prior art CN110903276A; Obtained according to the method described in prior art CN111732578A; Obtained according to the method described in existing technology WO2009072587A1; Obtained according to the method described in existing technology WO2009061145A1.

[0235] 3. NMR data for some compounds are shown in Table 7:

[0236] Table 7

[0237]

[0238] Fabrication and evaluation of organic electroluminescent devices

[0239] Example 1: Red Organic Electroluminescent Device

[0240] The anode is prepared through the following process: [The anode thickness is...] On the ITO / Ag / ITO experimental substrate, surface treatment was performed using ultraviolet light, ozone, and O2:N2 plasma to increase the work function of the anode, and the surface of the experimental substrate was cleaned with organic solvents to remove impurities and oil stains.

[0241] On the anode substrate, compound H12 and compound PD-1 were co-deposited at a deposition rate ratio of 98%:2% to form a layer with a thickness of [missing information]. Hole injection layer.

[0242] Compound H12 was deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0243] Compound 4 was deposited on the hole transport layer to form a thickness of [missing information]. The light-emitting adjustment layer.

[0244] On the light-emitting adjustment layer, compounds p-RH-1, n-RH-1, and RD-1 were co-deposited at a deposition rate ratio of 65%:35%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer.

[0245] On the red light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 50%:50% deposition rate to form a layer with a thickness of [missing information]. The electron transport layer.

[0246] Yb is deposited on the electron transport layer to form a thickness of The electron injection layer.

[0247] On the electron-injected layer, magnesium (Mg) and silver (Ag) are co-deposited at a deposition rate of 10%:90% to form a layer with a thickness of [thickness value missing]. The cathode.

[0248] Finally, compound CP-1 is deposited on the cathode to form a thickness of [thickness value missing]. An organic coating layer is applied to complete the fabrication of a red organic electroluminescent device.

[0249] Examples 2 to 39:

[0250] Organic electroluminescent devices were prepared using the same method as in Example 1, except that: when preparing the hole injection layer and hole transport layer, the hole transport layer material in Table 8 was used to replace compound H12 in Example 1; and when preparing the luminescence adjustment layer, the luminescence adjustment layer material in Table 8 was used to replace compound 4 in Example 1.

[0251] Comparative Examples 1 to 4:

[0252] Organic electroluminescent devices were prepared using the same method as in Example 1, except that: when preparing the luminescence adjustment layer, compounds A, B, and C from Table 8 were used to replace compound 4 in Example 1; and when preparing the hole transport layer, compounds H17, HTL-D, HTL-E, and HTL-F from Table 8 were used to replace compound H12 in Example 1.

[0253] In the fabrication of organic electroluminescent devices, the structures of the various materials used in the comparative and examples are as follows:

[0254]

[0255]

[0256] The performance of the red organic electroluminescent devices prepared in Examples 1-39 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the condition of 20 mA / cm. 2 The lifetime of the T95 device was tested under the following conditions, and the test results are shown in Table 8 below.

[0257] Table 8

[0258]

[0259]

[0260] As can be seen from Table 8 above, compared with the organic electroluminescent devices of Comparative Examples 1 to 4, the organic electroluminescent devices of Examples 1 to 39 have significantly improved performance, mainly manifested in the following: the operating voltage of the device is reduced by at least 0.14V, the luminous efficiency is increased by at least 10.17%, and the T95 lifetime is increased by at least 14.96%.

[0261] The core structure of the organic compound in this application is: An aromatic amine group is simultaneously attached to the 2,2-position of the adamantyl group. When an alkyl group and an aromatic amine group are attached to the same carbon atom of an adamantyl alkyl group, the glass transition temperature of the material can be increased, molecular rigidity reduced, and vapor deposition properties optimized, thereby significantly extending the application life of the material and greatly improving molecular polarization. Furthermore, in the fabrication of organic electroluminescent devices, applying the above-mentioned organic compounds to the light-emitting adjustment layer, while using carbazole compounds with an aromatic amine substituent at the 3-position as the hole transport layer, can significantly improve device performance. The reason for this may be that, compared to the rigid planar aryl substituent in the comparative compounds or the structure where an aromatic amine is directly attached to the 1-position of adamantyl, the small-volume alkyl group can improve the rigidity of the adamantyl alkyl group and increase the area of ​​the non-conjugated region. When the adamantyl alkyl group is simultaneously attached to the conjugated aromatic amine group at the 2,2-position, the molecule has stronger electron blocking properties, which promotes the effect on both adjacent layers when used as the light-emitting adjustment layer. Specifically, when this organic compound is used in conjunction with a carbazole-based hole transport material containing a 3-position aromatic amine substituent with high mobility, it can promote the balance of hole transport and injection, and effectively block electrons and excitons, thereby increasing the recombination probability of excitons, thus improving device efficiency and lifetime. In addition, due to the increase in non-conjugated regions in the compound of this application, the orientation probability of its organic film layer is increased, the interface effect between the hole transport layer and the light-emitting adjustment layer is weakened, resulting in improved device performance.

[0262] The preferred embodiments of this application have been described in detail above. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Wherein, R is selected from substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms; Each L may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms; n is the number of L groups connected in sequence, and n is selected from 1, 2 or 3; L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms. The substituents in R may be the same or different, and each is independently selected from deuterium, halogen groups, and cyano groups; The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, deuterated heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms.

2. The organic compound according to claim 1, characterized in that, R is selected from alkyl groups having 1 to 5 carbon atoms; Optionally, R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, or neopentyl.

3. The organic compound according to claim 1, characterized in that, Each L may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms; The substituents in each L may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms; Optionally, L1 and L2 may be the same or different, and each may be independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms. The substituents in L1 and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or trialkylsilyl with 3 to 9 carbon atoms; Optionally, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 25 carbon atoms. The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, aryl with 6 to 12 carbon atoms, and deuterated aryl with 6 to 12 carbon atoms.

4. The organic compound according to claim 1, characterized in that, Each L may be the same or different, and each is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene; Optionally, the substituents in each L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, pentadeuterated phenyl or trimethylsilyl.

5. The organic compound according to claim 1, characterized in that, Selected from the group consisting of the following groups:

6. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and each is independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, or substituted or unsubstituted carbazolylene. Optionally, the substituents in L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, trifluoromethyl, phenyl, naphthyl, pentadeuterated phenyl or trimethylsilyl; Optionally, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

7. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, or substituted or unsubstituted groups of the following: The substituents in Ar1 and Ar2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, biphenyl, pentadeuterated phenyl; Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

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

9. An electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises any one of the organic compounds according to claims 1 to 8.

10. The electronic component according to claim 9, characterized in that, The electronic component is an organic electroluminescent device or a photoelectric conversion device; Optionally, the functional layer includes a light-emitting auxiliary layer, which contains the aforementioned organic compound.

11. The electronic component according to claim 9, characterized in that, The functional layer further includes a hole transport layer, which comprises a carbazole compound as shown in Formula II: Among them, L3, L4 and L5 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms. The substituents in L3, L4, L5, Ar3, and Ar4 may be the same or different, and each is independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, or triarylsilyl with 18 to 24 carbon atoms; Each R1, each R2, and each R3 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, or deuterated heteroaryl with 3 to 20 carbon atoms; n1 is the number of R1s, and n1 can be selected from 0, 1, 2, 3 or 4; n2 is the number of R2, and n2 is selected from 0, 1, 2 or 3; n3 is the number of R3s, and n3 is selected from 0, 1, 2, 3, 4 or 5.

12. The electronic component according to claim 11, characterized in that, L3, L4 and L5 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene. The substituents in L3, L4 and L5 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, trifluoromethyl, trimethylsilyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl or phenyl; Optionally, Ar3 and Ar4 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazolyl. The substituents in Ar3 and Ar4 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, naphthyl, dibenzofuranyl or dibenzothiophene or carbazoyl. Optionally, each of R1, each of R2 and each of R3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n-butyl, trifluoromethyl, trideuterated methyl, phenyl, pentadeuterated phenyl, naphthyl or biphenyl.

13. The electronic component according to claim 11, characterized in that, The carbazole compounds are selected from the group consisting of the following compounds:

14. An electronic device comprising the electronic element as described in any one of claims 9 to 13.

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