Organic compound, organic electroluminescence device, and electronic device

Abstract

The application belongs to the technical field of organic materials, and provides an organic compound, a structure of the organic compound is shown as formula 1. The application also provides an organic electroluminescent device and an electronic device containing the organic compound. The organic compound as a hole transport layer material can effectively reduce the driving voltage of the organic electroluminescent device, improve the light-emitting efficiency thereof and prolong the service life thereof.

Description

Technical Field

[0001] This application relates to the field of organic materials technology, and in particular to an organic compound, an organic electroluminescent device, and an electronic device. Background Technology

[0002] Currently, research on organic electroluminescent materials has been widely carried out in academia and industry, and a large number of high-performance organic electroluminescent materials have been developed. Overall, the future direction of organic electroluminescent devices is the development of high-efficiency, long-lifetime, and low-cost white light devices and full-color display devices; however, the industrialization process of this technology still faces many key challenges. Therefore, designing and finding a stable and efficient compound as a novel material for organic electroluminescent devices to overcome its shortcomings in practical applications is a key focus and future research trend in organic electroluminescent device materials research. With the development of electronic technology and the progress of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. These electronic components typically include a cathode and an anode arranged opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists 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.

[0003] Typically, hole transport materials have poor stability and low transport efficiency. When used in organic electroluminescent devices, they cannot truly balance hole-electron transport, resulting in reduced device luminous efficiency and shortened lifespan.

[0004] Currently, although a large number of high-performance organic electroluminescent materials have been developed, this technology still faces many challenges. Therefore, designing new materials with better performance to reduce the driving voltage of organic electroluminescent devices, improve their luminous efficiency, and extend their lifespan is a pressing issue that needs to be addressed in this field. Summary of the Invention

[0005] The purpose of this application is to overcome the shortcomings of the prior art and provide an organic compound and an organic electroluminescent device and electronic device containing the same, which can improve luminous efficiency and extend device life.

[0006] To achieve the above-mentioned objectives, the first aspect of this application provides an organic compound, the structure of which is shown in Formula 1:

[0007]

[0008] In this formula, one of ring A and ring B is selected from the structure shown in Formula 2, and the other is a benzene ring. The asterisk (*) in Formula 2 indicates that Formula 2 is different from Formula 1. or The positions where they overlap;

[0009] X is selected from C(R1R2), O, or S;

[0010] R1 and R2 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms or deuterated alkyl groups having 1 to 10 carbon atoms;

[0011] R3 and R4 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms or aryl groups having 6 to 12 carbon atoms;

[0012] L, L1, and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene with 3 to 30 carbon atoms.

[0013] Ar1 and Ar2 may be the same or different, and are 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.

[0014] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, or deuterated alkyl groups with 1 to 10 carbon atoms;

[0015] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0016] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising the organic compound described in the first aspect of this application.

[0017] A third aspect of this application provides an electronic device, which includes the organic electroluminescent device described in the second aspect of this application.

[0018] Through the above technical solution, the chemical structure of the organic compound in this application includes benzo[a]fluorene, furan, thiophene-fused oxaphenanthrene, and triarylamine. In the oxaphenanthrene group, both methyl groups and oxygen can donate electrons to the benzene ring through conjugation / hyperconjugation effects, thus giving the group a high conjugated electron cloud density. When combined with triarylamine, it exhibits a high hole mobility, thereby improving the luminous efficiency of the device when used as the hole transport layer in an organic electroluminescent device. While possessing a relatively planar structure, the oxaphenanthrene group exhibits greater asymmetry and steric hindrance compared to typical planar conjugated groups, resulting in lower crystallinity and good film-forming properties. This effectively extends the lifespan of the electroluminescent device when applied to it.

[0019] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0020] The accompanying drawings, which are incorporated in and form part of this specification, illustrate embodiments consistent with this application and, together with the description, serve to explain the principles of this application.

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

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

[0023] Explanation of reference numerals in the attached figures

[0024] 100, Anode; 200, Cathode; 300, Functional layer; 310, Hole injection layer; 321, Hole transport layer; 322, Electron blocking layer; 330, Organic electroluminescent layer; 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device.

[0025] The accompanying drawings illustrate specific embodiments of this application, which will be described in more detail below. These drawings and descriptions are not intended to limit the scope of the concept in any way, but rather to illustrate the concept of this application to those skilled in the art through reference to particular embodiments. Detailed Implementation

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, they are provided so that this application will be more comprehensive and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0027] For clarity, the thickness of regions and layers may be exaggerated in the figures. The same reference numerals in the figures denote the same or similar structures, and therefore their detailed descriptions will be omitted.

[0028] The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. Numerous specific details are provided in the following description to give a thorough understanding of embodiments of this application.

[0029] The first aspect of this application provides an organic compound, the structure of which is shown in Formula 1:

[0030]

[0031] In this formula, one of ring A and ring B is selected from the structure shown in Formula 2, and the other is a benzene ring. The asterisk (*) in Formula 2 indicates that Formula 2 is different from Formula 1. or The positions where they overlap;

[0032] X is selected from C(R1R2), O, or S;

[0033] R1 and R2 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms or deuterated alkyl groups having 1 to 10 carbon atoms;

[0034] R3 and R4 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms or aryl groups having 6 to 12 carbon atoms;

[0035] L, L1, and L2 may be the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene with 3 to 30 carbon atoms.

[0036] Ar1 and Ar2 may be the same or different, and are 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.

[0037] The substituents in L, L1, L2, Ar1, and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, heteroaryl groups with 12 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, haloaryl groups with 6 to 20 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, triarylsilyl groups with 18 to 24 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, or deuterated alkyl groups with 1 to 10 carbon atoms;

[0038] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0039] In this application, the terms "optional" or "optionally" mean that the event or situation described below may occur but does not have to occur, and the description includes the possibility that the event or situation may or may not occur. For example, "optionally, two adjacent substituents form a ring;" means that the two substituents may form a ring but are not required to form a ring, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0040] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...independently selected from" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, " In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0041] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. The term "" indicates that one end of the linker bond can connect to any position in the ring system that the bond penetrates, while the other end connects to the rest of the compound molecule.

[0042] For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule by two non-positional linkages that span the bicyclic ring, which means that any possible connection mode is shown as in equations (f-1) to (f-10).

[0043]

[0044] .

[0045] For another example, as shown in equation (X'), the phenanthrene group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode is shown in equations (X'-1) to (X'-4).

[0046] .

[0047] In this application, a non-positional substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-positional linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7).

[0048]

[0049] .

[0050] In this application, the number of carbon atoms in L, L1, L2, Ar1, and Ar2 refers to the total number of carbon atoms. For example, if L1 is selected from a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12. For example, Ar1 is... Therefore, its carbon number is 7; L1 is It has 12 carbon atoms.

[0051] In this application, unless otherwise specifically defined, "heteroatom" means a functional group comprising at least one heteroatom such as B, N, O, S, Se, Si, or P, with the remaining atoms being carbon and hydrogen. An unsubstituted alkyl group may be a "saturated alkyl group" without any double or triple bonds.

[0052] In this application, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group can have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, the alkyl group is selected from alkyl groups having 1 to 5 carbon atoms, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and pentyl.

[0053] In this application, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 3 to 10 carbon atoms; in this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it may contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0054] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, 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, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, phenyl, etc. The "substituted or unsubstituted aryl group" of this application may contain 6-30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-25; in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-20; in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-18; and in other embodiments, the number of carbon atoms in the substituted or unsubstituted aryl group may be 6-15. For example, in this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 18, 20, 24, 25, or 30. Of course, the number of carbon atoms can also be other numbers, which will not be listed here. In this application, biphenyl can be understood as a phenyl-substituted aryl group or an unsubstituted aryl group.

[0055] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0056] In this application, the substituted aryl group may be one or more hydrogen atoms of the aryl group that are replaced by groups such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, etc.

[0057] It should be understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and its substituents is 18.

[0058] In this application, aryl groups used as substituents include, but are not limited to, phenyl, naphthyl, anthraceneyl, phenanthryl, dimethylfluorenyl, biphenyl, etc.

[0059] In this application, the fluorene group may be substituted, and two substituents may combine with each other to form a spirostructure. Specific embodiments include, but are not limited to, the following structures:

[0060] .

[0061] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms, wherein the heteroatoms can be at least one of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic or polycyclic heteroaryl group; in other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings conjugated by carbon-carbon bonds, and any aromatic ring system can be a single aromatic monocyclic ring or a fused aromatic ring. For example, heteroaryl groups may include thiophene, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, benzoxazolyl, and benzimidazole. The group includes, but is not limited to, benzothiazolyl, benzocarbazolyl, benzothiophenel, dibenzothiophenel, thienozothiophenel, benzofuranyl, phenanthrolinel, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silanyl, dibenzofuranyl, and N-arylcarbazolyl (such as N-phenylcarbazolyl), N-heteroarylcarbazolyl (such as N-pyridylcarbazolyl), and N-alkylcarbazolyl (such as N-methylcarbazolyl), etc. Among these, thiophenel, furanyl, and phenanthrolinel are heteroaryl groups of the single aromatic ring type, while N-arylcarbazolyl (such as N-phenylcarbazolyl) and N-heteroarylcarbazolyl are heteroaryl groups of the polycyclic system type linked by carbon-carbon conjugation. The "substituted or unsubstituted heteroaryl group" of this application may contain 3 to 30 carbon atoms. In some embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 3 to 27; in other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12 to 24; and in still other embodiments, the number of carbon atoms in the substituted or unsubstituted heteroaryl group may be 12 to 20. For example, the number of carbon atoms may be 3, 4, 5, 7, 12, 13, 18, or 20. Of course, the number of carbon atoms may also be other numbers, which will not be listed here.

[0062] In this application, the term "hybrid aryl" refers to a divalent group formed by the further loss of a hydrogen atom by a heteroaryl group.

[0063] In this application, the substituted heteroaryl group may be one or more hydrogen atoms of the heteroaryl group that are replaced by groups such as deuterium, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, etc.

[0064] It should be understood that the number of carbon atoms in a substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on it.

[0065] In this application, the heteroaryl group used as a substituent includes, but is not limited to, dibenzofuranyl, dibenzothiophenyl, carbazoyl, N-phenylcarbazoyl, etc.

[0066] In this application, halogen groups may include fluorine, iodine, bromine, chlorine, etc.

[0067] In this application, a deuterated aryl group may be one or more hydrogen atoms of an aryl group that are replaced by deuterium. Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl.

[0068] In this application, the halogenated aryl group can be one or more hydrogen atoms of the aryl group that are replaced by halogen atoms. Specific examples of halogenated aryl groups include, but are not limited to, fluorophenyl and chlorophenyl.

[0069] In this application, a haloalkyl group may be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

[0070] In this application, terphenyl includes and .

[0071] In some embodiments of this application, the organic compound has a structure shown in any one of Formulas 3 to 6:

[0072]

[0073] In other embodiments of this application, the organic compound has a structure shown in any one of the following formulas A to Z':

[0074]

[0075]

[0076] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

[0077] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, heteroaryl with 5 to 12 carbon atoms, aryl with 6 to 12 carbon atoms, deuterated aryl with 6 to 12 carbon atoms, or alkyl with 1 to 5 carbon atoms.

[0078] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring ( ).

[0079] Further optionally, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0080] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthracene, substituted or unsubstituted pyrene, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl or substituted or unsubstituted phenanthrolinel.

[0081] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl.

[0082] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0083]

[0084] The substituted group V has one or more substituents, and the substituents in the substituted group V are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl, and when the number of substituents on group V is greater than 1, the substituents are the same or different.

[0085] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096] .

[0097] In some embodiments of this application, L is selected from single bonds or substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0098] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, and alkyl or phenyl groups having 1 to 5 carbon atoms.

[0099] In other embodiments of this application, L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene.

[0100] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0101] Specifically, L is selected from the group consisting of single bonds or the following groups:

[0102] .

[0103] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, or substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0104] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, heteroaryl groups with 5 to 12 carbon atoms, aryl groups with 6 to 12 carbon atoms, deuterated aryl groups with 6 to 12 carbon atoms, or alkyl groups with 1 to 5 carbon atoms.

[0105] In other embodiments of this application, L1 and L2 may be the same or different, and are each independently selected from single-bonded, substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of:

[0106]

[0107] The substituted group W has one or more substituents, and the substituents in the substituted group W are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.

[0108] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophene.

[0109] Optionally, the substituents in phases L1 and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0110] Specifically, L1 and L2 may be the same or different, and are each independently selected from the group consisting of single bonds or the following groups:

[0111]

[0112]

[0113] .

[0114] In some embodiments of this application, and They may be the same or different, and each is independently selected from the group consisting of:

[0115]

[0116]

[0117]

[0118] Optionally, and They may be the same or different, and each is independently selected from the group consisting of:

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] .

[0135] In some embodiments of this application, both R1 and R2 are methyl groups.

[0136] In some embodiments of this application, R3 and R4 may be the same or different, and are independently selected from methyl or phenyl.

[0137] Optionally, the organic compound is selected from the group consisting of:

[0138]

[0139] This application does not specifically limit the synthesis methods of the provided organic compounds. Those skilled in the art can determine suitable synthesis methods based on the organic compounds provided in the preparation examples section of this application. Those skilled in the art can obtain all the organic compounds provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic compounds will not be detailed here, and should not be construed as limitations on this application.

[0140] A second aspect of this application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the cathode and the anode, the functional layer comprising the organic compound described in the first aspect of this application.

[0141] For example, such as Figure 1 As shown, the organic electroluminescent 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 the first aspect of this application.

[0142] In another specific embodiment of this application, the organic electroluminescent device may be, for example, a blue organic electroluminescent device.

[0143] In another specific embodiment of this application, the functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

[0144] In one specific embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an electron blocking layer 322, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 350, and a cathode 200 stacked sequentially.

[0145] In one specific embodiment, the anode 100 comprises the following anode materials, preferably materials with a large work function that facilitate hole injection into the functional layer. The anode materials specifically 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 and SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is also included.

[0146] In one specific embodiment, the hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. In one specific embodiment, the hole transport layer 321 is composed of organic compounds of this application.

[0147] In one specific embodiment, the electron blocking layer 322 may comprise one or more materials, selected from carbazole polymers or other types of compounds, without specific limitation in this application. In one specific embodiment, the electron blocking layer 322 is composed of the compound HT-12.

[0148] In this application, the electron transport layer 350 can be a single-layer structure or a multi-layer structure, and it can include one or more electron transport materials. The electron transport materials can also include those selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any special limitations on this. In one specific embodiment, the electron transport layer 350 is composed of compound LiQ and compound ET-01.

[0149] In this application, the organic electroluminescent layer 330 can be composed of a single luminescent material or of a host material and a guest material. Preferably, the organic electroluminescent layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic electroluminescent layer 330 can recombine in the organic electroluminescent layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0150] The host material of the organic electroluminescent layer 330 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. In one specific embodiment, the host material of the organic electroluminescent layer is composed of compound BH-1.

[0151] The guest material of the organic electroluminescent layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, and this application does not impose any special limitations on this. In one specific embodiment, the guest material is compound BD-1.

[0152] In one specific embodiment, the cathode 200 includes a cathode material that has a small work function, which facilitates electron injection into the functional layer. Specifically, examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto. Preferably, a metal electrode containing silver and magnesium serves as the cathode.

[0153] In this application, as Figure 1As shown, a hole injection layer 310 may also be disposed 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 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. In some embodiments of this application, the hole injection layer 310 may be composed of the compound HAT-CN.

[0154] In one specific implementation, such as Figure 1 As shown, an electron injection layer 360 may also be disposed between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. In one specific embodiment, the electron injection layer 360 may include ytterbium (Yb).

[0155] A third aspect of this application provides an electronic device, including the organic electroluminescent device provided in the second aspect of this application.

[0156] According to one implementation method, such as Figure 2 As shown, the electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. 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.

[0157] The following examples illustrate the synthesis method of the nitrogen-containing compounds of this application, but this application is not limited thereto.

[0158] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0159] Synthesis of intermediate IM a1-X

[0160] The synthesis of IM a1-X is illustrated using IM a1-1 as an example:

[0161]

[0162] (1) Methyl 2-bromo-5-chlorobenzoate (15.00 g, 60.12 mmol), 3-methoxydibenzofuran-2-boronic acid (14.55 g, 60.12 mmol), potassium carbonate (16.62 g, 120.25 mmol), tetrabutylammonium bromide (1.94 g, 6.01 mmol), toluene (75 mL), ethanol (45 mL), and deionized water (30 mL) were added to a three-necked flask. The mixture was stirred for 15 min under nitrogen protection, and then tetra(triphenylphosphine)palladium (0.70 g, 0.60 mmol) was added. The mixture was heated to 75-80°C and stirred for 5 h. The reaction mixture was cooled to room temperature, and toluene (100 mL) was added for extraction. The organic phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed from the organic phase under reduced pressure to obtain a yellow oily crude product. The crude product was purified by recrystallization using a dichloromethane / ethanol system to obtain an off-white solid IM. a1-a1 (15.90g, yield: 72.10%).

[0163]

[0164] (2) The intermediate IM a1-a1 (13.50 g, 36.80 mmol) and tetrahydrofuran (100 mL) were added to a three-necked flask and stirred. Under nitrogen protection, 3 M methyl magnesium bromide THF solution (24.50 mL, 73.60 mmol) was slowly added dropwise. After the addition was complete, the mixture was stirred at room temperature for 1 h. Then the temperature was raised to 60-66°C and stirred for 6 h. The reaction solution was cooled to room temperature, and dichloromethane (135 mL) was added. Deionized water (100 mL) was slowly added while stirring. The reaction solution was then slowly added to 1 mol / L dilute hydrochloric acid (100 mL). After stirring, the mixture was allowed to stand and separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The pale yellow oily substance IM a1-a2 (12.40 g, yield: 91.85%) was obtained.

[0165]

[0166] (3) Add intermediate IM a1-a2 (12.00 g, 32.71 mmol) and acetonitrile (100 mL) to a three-necked flask, start stirring and cool the system to 0~10°C, then add 1 M boron tribromide dichloromethane solution (32.71 mL, 32.71 mmol) dropwise, control the temperature at 0~10°C, and after 1 h, let the system rise naturally to room temperature and stir for about 5 h; then add deionized water (100 mL) and dichloromethane (100 mL) to the reaction solution, separate the liquid and dry the organic phase with anhydrous magnesium sulfate, filter, and remove the solvent under reduced pressure; the obtained yellow oily crude product is purified by silica gel column chromatography with n-heptane to obtain white solid intermediate IM a1-1 (7.60 g, yield: 69.42%).

[0167] Other IM a1-X listed in Table 1 were synthesized using the same method as IM a1-1, except that methyl 2-bromo-5-chlorobenzoate was used instead of methyl 2-bromo-5-chlorobenzoate in step (1), and 3-methoxydibenzofuran-2-boronic acid was used instead of methyl 2-bromo-5-chlorobenzoate in step (1). The structures of raw material 1, raw material 2 and IM a1-X, as well as the yield of the last step, are shown in Table 1.

[0168] Table 1

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] Synthesis of Compound 1-1

[0176]

[0177] (1) IM a1-1 (7.00 g, 20.91 mmol), 4-aminobiphenyl (3.54 g, 20.91 mmol), tris(dibenzylideneacetone)palladium (0.19 g, 0.21 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.17 g, 0.42 mmol) and sodium tert-butoxide (3.01 g, 31.36 mmol) were added to toluene (70 mL), heated to 108 °C under nitrogen protection, stirred for 2 h, and then cooled to room temperature. The reaction solution was washed with water and separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization using a dichloromethane / n-heptane system to obtain an off-white solid intermediate IM A1-a1 (7.20 g, 73.64%).

[0178]

[0179] (2) IMA1-a1 (6.00 g, 12.83 mmol), 4-bromobiphenyl (2.99 g, 12.83 mmol), tris(dibenzylacetone)dipalladium (0.12 g, 0.13 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.12 g, 0.26 mmol), and sodium tert-butoxide (1.85 g, 19.25 mmol) were added to toluene (60 mL). The mixture was heated to 108°C under nitrogen protection and stirred for 3 h. After cooling to room temperature, the reaction solution was washed with water and separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure. The crude product was purified by recrystallization from toluene to obtain a white solid compound, namely compound 1-1 (5.30 g, yield 66.7%). Mass spectrometry: m / z = 620.3 [M+H] + ;

[0180] The compounds listed in Table 4 were synthesized using the same method as compound 1-1, except that reactant 3 was used instead of IM a1-X, reactant 4 was used instead of 4-aminobiphenyl, and reactant 5 was used instead of 4-bromobiphenyl. The main reactants used, the synthesized compounds, the yield of the final step, and the mass spectrometry results are shown in Table 2.

[0181] Table 2

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] The synthesized compounds were subjected to proton nuclear magnetic resonance (NMR) spectroscopy analysis, and the data are shown in Table 3 below:

[0192] Table 3

[0193]

[0194] Example 1: Fabrication of a blue organic electroluminescent device

[0195] The anode is prepared by the following process: an ITO substrate with an ITO / Ag / ITO thickness of 110 / 1000 / 70Å is cut into dimensions of 40mm (length) × 40mm (width) × 0.7mm (thickness). The substrate is then prepared into an experimental substrate with cathode, anode and insulating layer patterns by photolithography. The surface can be treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can be cleaned with organic solvents to remove impurities and oil stains.

[0196] On the experimental substrate (anode), HAT-CN and compound HT-11 were co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 Å. Then, compound 1-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 990 Å.

[0197] HT-12 was vacuum-deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0198] On the electron blocking layer, compound BH-1 (doped host) and compound BD-1 (doped guest) were co-deposited at a thickness ratio of 98%:2% to form an organic electroluminescent layer (EML) with a thickness of 220 Å.

[0199] On the light-emitting layer, compound ET-01 and LiQ are mixed in a 1:1 thickness ratio and deposited together to form a 350 Å thick electron transport layer (ETL). Yb is deposited on the electron transport layer to form a 15 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:10 deposition rate and vacuum deposited on the electron injection layer to form a 115 Å thick cathode.

[0200] Furthermore, a CP-1 layer with a thickness of 650 Å was vacuum-deposited onto the aforementioned cathode, thereby completing the fabrication of the blue organic electroluminescent device.

[0201] Examples 2-42

[0202] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compounds in Table 5 were used instead of compounds 1-1 in Example 1 when preparing the hole transport layer.

[0203] Comparative Examples 1-3

[0204] Organic electroluminescent devices were prepared using the same method as in Example 1, except that compounds in Table 5 were used instead of compounds 1-1 in Example 1 when preparing the hole transport layer.

[0205] The performance of the blue organic electroluminescent devices prepared in Examples 1-42 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 15 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 5 below.

[0206] The material structures used in the above embodiments and comparative examples are shown in Table 4 below:

[0207] Table 4

[0208]

[0209] Table 5

[0210]

[0211] As shown in Table 5, the organic electroluminescent devices of Examples 1-42 exhibit significantly improved performance compared to those of Comparative Examples 1-3. Specifically, the current efficiency of Examples 1-42 was improved by at least 19.0%, and the lifetime was improved by at least 17.0%.

Claims

1. An organic compound, characterized in that, The organic compound has a structure represented by any one of the following formulas: Among them, R1, R2, R3 and R4 are methyl groups; L represents a single bond; L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, substituted or unsubstituted dibenzothiophene groups, substituted or unsubstituted dibenzofuran groups, or substituted or unsubstituted carbazolyl groups. The substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6 to 12 carbon atoms, deuterated aryl groups with 6 to 12 carbon atoms, or alkyl groups with 1 to 5 carbon atoms. Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms. The substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, aryl groups with 6 to 12 carbon atoms, deuterated aryl groups with 6 to 12 carbon atoms, or alkyl groups with 1 to 5 carbon atoms. Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

2. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, substituted or unsubstituted dibenzothiophene groups, substituted or unsubstituted dibenzofuran groups, or substituted or unsubstituted carbazolyl groups.

3. The organic compound according to claim 1, characterized in that, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of: The substituted group W has one or more substituents, and the substituents in the substituted group W are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.

4. The organic compound according to claim 1, characterized in that, In Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

5. The organic compound according to claim 1, characterized in that, Ar1 and Ar2 may be the same or different, and are each independently selected from substituted or unsubstituted groups V, wherein the unsubstituted groups V are selected from the group consisting of: The substituted group V has one or more substituents, and the substituents in the substituted group V are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl or pentadeuterated phenyl, and when the number of substituents on group V is greater than 1, the substituents are the same or different.

6. The organic compound according to claim 1, characterized in that, and They may be the same or different, and each is independently selected from the group consisting of:

7. The organic compound according to claim 1, characterized in that, The organic compound is selected from the group consisting of the following compounds:

8. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and at least one functional layer disposed between the anode and the cathode, the functional layer comprising an organic compound as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The functional layer includes a hole transport layer, and the hole transport layer includes the organic compound.

10. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 8 or 9.

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