Organic compound, organic electroluminescence device, and electronic device

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic compound, an organic electroluminescent device using the same and an electronic device. The organic compound has a structure as shown in formula 1. When the organic compound is used in an organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

Technical Field

[0001] This application relates to the field of organic compound technology, and more particularly to an organic compound and an organic electroluminescent device and electronic device containing the organic compound. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components for realizing electroluminescence is becoming increasingly wide. These electronic components typically include a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer located between the organic light-emitting layer and the anode, and an electron transport layer located between the organic light-emitting layer and the cathode. Taking an organic electroluminescent device as an example, it generally includes an anode, a hole transport layer, an organic light-emitting layer, an electron transport layer, and a cathode stacked sequentially. When a voltage is applied to the anode and cathode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the organic light-emitting layer, and holes on the anode side also move towards the organic light-emitting layer. Electrons and holes combine in the organic light-emitting layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light.

[0003] Existing technologies disclose host materials for fabricating organic light-emitting layers in organic electroluminescent devices. However, it remains necessary to continue developing novel materials to further improve the performance of electronic components. Summary of the Invention

[0004] To address the aforementioned problems, this application aims to provide an organic compound and an organic electroluminescent device and electronic device comprising the organic compound, wherein the organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0005] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0006]

[0007] Formula 1

[0008] Among them, ring A is a benzene ring or a naphthalene ring;

[0009] X1 is O, S, or X2 is O, S or And one of X1 and X2 is O or S, and the other is ;

[0010] L1, L2, and L3 may be the same or different, and are 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.

[0011] L is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0012] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0013] The substituents of L, L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 5 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0014] Optionally, any two adjacent substituents may form a ring;

[0015] Each R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 5 to 18 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0016] n1 represents the number of R1s, which can be selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, all R1s may be the same or different.

[0017] n2 represents the number of R2s, which can be selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, all R2s are either the same or different.

[0018] According to a second aspect of this application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned organic compound.

[0019] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0020] The core group of the organic compound in this application is a benzoxazole-fused carbazole group. This core group has a large conjugated system, which connects with a triazine group to form a new compound. The substituent at the 2-position of the benzoxazole is spatially parallel to the triazine group, which on the one hand enhances intermolecular forces and improves the carrier mobility of the compound; on the other hand, it helps to reduce the molecular volume and lower the evaporation temperature. When the organic compound of this application is used as the electron transport host material in a hybrid host material, it can improve the carrier balance in the light-emitting layer, widen the carrier recombination region, improve exciton generation and utilization efficiency, and improve the luminous efficiency and lifetime of the device.

[0021] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0022] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0023] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0024] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0025] Figure Labels

[0026] Detailed Implementation

[0027] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device containing the organic compound. The organic compound can improve the performance of the organic electroluminescent device and electronic device, such as reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0028] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0029]

[0030] Formula 1

[0031] Among them, ring A is a benzene ring or a naphthalene ring;

[0032] X1 is O, S, or X2 is O, S or And one of X1 and X2 is O or S, and the other is ;

[0033] L1, L2, and L3 may be the same or different, and are 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.

[0034] L is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0035] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0036] The substituents of L, L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteryl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuteryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 5 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0037] Optionally, any two adjacent substituents may form a ring;

[0038] Each R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 5 carbon atoms, haloalkyl with 1 to 5 carbon atoms, deuterated alkyl with 1 to 5 carbon atoms, aryl with 6 to 18 carbon atoms, deuterated aryl with 6 to 18 carbon atoms, heteroaryl with 5 to 18 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0039] n1 represents the number of R1s, which can be selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, all R1s may be the same or different.

[0040] n2 represents the number of R2s, which can be selected from 0, 1, 2, 3 or 4. When n2 is greater than 1, all R2s are either the same or different.

[0041] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" 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 the formula Q-1, 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.

[0042] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, cyano, halogen group, alkyl, haloalkyl, deuterated alkyl, aryl, deuterated aryl, haloaryl, heteroaryl, cycloalkyl, etc. The number of substituents can be one or more.

[0043] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0044] In this application, the number of carbon atoms in substituted or unsubstituted functional groups refers to the total number of carbon atoms. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0045] 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, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, phenyl, spirodifluorenyl, etc. In this application, the arylene group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0046] In this application, terphenyl includes and .

[0047] In this application, the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to a total number of 18 carbon atoms in the aryl group and the substituents.

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, 30, 31, 32, 33, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0049] In this application, the fluorene group can be replaced by one or more substituents, wherein any two adjacent substituents can combine with each other to form a ring structure. When the fluorene group is replaced as described above, the substituted fluorene group can be: , , , etc., but not limited to this.

[0050] In this application, aryl groups used as substituents for L, L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, etc.

[0051] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0052] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 5 to 20 carbon atoms, and in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 18 carbon atoms.

[0053] 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 atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms of the heteroaryl group and the substituents on the heteroaryl group.

[0054] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0055] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0056] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0057] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0058] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0059] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0060] In this application, the single bond extending from the loop system involved in the non-positioning link is not specified. The term "" indicates that one end of the linker can be connected to any position in the ring system that the linker penetrates, and the other end is connected to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that penetrate the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0061]

[0062] .

[0063] For another example, as shown in the following formula (X'), the dibenzofuran group represented by formula (X') is connected to other positions of the molecule through a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in formulas (X'-1) to (X'-4) is included.

[0064] .

[0065] In some embodiments of this application, X1 is 0, and X2 is... .

[0066] In other embodiments of this application, X1 is X2 is 0.

[0067] In some embodiments of this application, the organic compound is selected from compounds represented by Formula 1-A or Formula 1-B:

[0068]

[0069] In some embodiments of this application, the organic compound is selected from compounds represented by formula 1-1, formula 1-2, formula 1-3, formula 1-4, formula 1-5, formula 1-6, formula 1-7, or formula 1-8:

[0070]

[0071] In some embodiments of this application, L is selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0072] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0073] Further optionally, L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0074] In other embodiments of this application, L is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazolyl.

[0075] 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, and phenyl.

[0076] Further optionally, L is selected from single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0077] Optionally, L is selected from the group consisting of single bonds or the following groups:

[0078] .

[0079] Specifically, L is selected from the group consisting of single bonds or the following groups:

[0080]

[0081] .

[0082] In some embodiments of this application, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0083] Optionally, the substituents in L1, L2 and L3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms.

[0084] Further optionally, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms.

[0085] Further optionally, L3 is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0086] In other embodiments of this application, L1, L2, and L3 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 fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0087] Optionally, the substituents in L1, L2 and L3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0088] Further optionally, L3 is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene.

[0089] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single-bonded, substituted or unsubstituted groups V, wherein the unsubstituted group V is selected from the group consisting of:

[0090]

[0091] in, The substituted group V represents a chemical bond; the substituted group V contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V contains multiple substituents, the substituents may be the same or different.

[0092] 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:

[0093]

[0094]

[0095] .

[0096] In some embodiments of this application, L3 is selected from single-bonded, substituted, or unsubstituted groups V1, and the unsubstituted groups V1 are selected from the group consisting of:

[0097]

[0098] in, The substituted group V1 represents a chemical bond; the substituted group V1 contains one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; and when the substituted group V1 contains multiple substituents, the substituents may be the same or different.

[0099] Optionally, L3 is selected from the group consisting of single bonds or the following groups:

[0100] .

[0101] Specifically, L3 is selected from the group consisting of single bonds or the following groups:

[0102]

[0103] .

[0104] In some embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 24 carbon atoms.

[0105] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, haloalkyl groups with 1 to 5 carbon atoms, deuterated alkyl groups with 1 to 5 carbon atoms, pentadeuterated phenyl groups or phenyl groups.

[0106] Optionally, in Ar1 and Ar2, any two adjacent substituents form a ring with 5 to 13 carbon atoms. For example, in Ar1 and Ar2, any two adjacent substituents form cyclohexane (… ), cyclopentane ( ), adamantane ( ), benzene ring, naphthalene ring or fluorene ring ( ).

[0107] 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.

[0108] Further optionally, Ar3 is selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or substituted or unsubstituted heteroaryl groups having 12 to 20 carbon atoms.

[0109] In other embodiments of this application, Ar1, Ar2, and Ar3 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 phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0110] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.

[0111] Further optionally, Ar3 is 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 triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene.

[0112] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted groups W; wherein, the unsubstituted group W is selected from the group consisting of:

[0113]

[0114] ;

[0115] in, It represents a chemical bond; the substituted group W has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on group W is greater than 1, the substituents may be the same or different.

[0116] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0117]

[0118]

[0119]

[0120] .

[0121] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] .

[0128] In some embodiments of this application, Ar3 is selected from substituted or unsubstituted groups W1; wherein, the unsubstituted group W1 is selected from the group consisting of:

[0129]

[0130] ;

[0131] in, It represents a chemical bond; the substituted group W1 has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl, and when the number of substituents on group W1 is greater than 1, the substituents may be the same or different.

[0132] Alternatively, Ar3 is selected from the group consisting of:

[0133]

[0134] .

[0135] Specifically, Ar3 is selected from the group consisting of the following groups:

[0136]

[0137]

[0138] .

[0139] In some embodiments of this application, and Each group is independently selected from the group consisting of the following groups:

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] .

[0146] Specifically, and Each group is independently selected from the group consisting of the following groups:

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] .

[0157] In some embodiments of this application, Selected from the group consisting of the following groups:

[0158]

[0159] .

[0160] Specifically, Selected from the group consisting of the following groups:

[0161]

[0162]

[0163] .

[0164] In some embodiments of this application, Selected from the group consisting of the following groups:

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] .

[0182] In some embodiments of this application, R1 and R2 may be the same or different, and are independently deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl.

[0183] In some embodiments of this application, both n1 and n2 are 0.

[0184] In some embodiments of this application, the organic compound is selected from the group consisting of:

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] 。

[0226] According to a second aspect of this application, this application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the organic compound of this application.

[0227] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light-emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially.

[0228] Optionally, the anode 100 includes an anode material that is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, indium tin oxide (ITO) is included as the transparent electrode for the anode.

[0229] Optionally, the first hole transport layer 320 and the second hole transport layer 330 include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. Those skilled in the art can refer to existing technologies for selection, and this application does not impose any special limitations in this regard. In some embodiments of this application, the first hole transport layer 320 is HT-22, and the second hole transport layer 330 is HT-23.

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] .

[0236] Optionally, a hole injection layer 310 may be provided between the anode 100 and the first hole transport layer 320 to enhance the ability to inject holes into the first hole transport layer 320. The hole injection layer 310 may be selected from benzidine derivatives, starburst-like aryl amine compounds, phthalocyanine derivatives, or other materials; this application does not impose any special limitations on this. The material of the hole injection layer 310 may, for example, be selected from the following compounds or any combination thereof;

[0237]

[0238]

[0239] .

[0240] In some embodiments of this application, the hole injection layer 310 is composed of PD and HT-22.

[0241] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting layer material, or it may include a host material and a dopant material. Optionally, the organic light-emitting layer 340 is composed of a host material and a dopant material. Holes and electrons injected into the organic light-emitting layer 340 can recombine in the organic light-emitting layer 340 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the dopant material, thereby enabling the dopant material to emit light.

[0242] The main material of the organic light-emitting layer 340 can be a metal chelate compound, a bis(styrene) derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. This application does not impose any special restrictions on this.

[0243] In one embodiment of this application, the organic light-emitting layer 340 contains the organic compounds of this application.

[0244] Optionally, the organic compound of this application is used as the host material (electronic host material) of the organic light-emitting layer 340.

[0245] In some embodiments of this application, the hole-type host material of the organic light-emitting layer 340 is... (RH-P)

[0246] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also referred to as a dopant or dopant. Specific examples of red phosphorescent dopants used in red organic electroluminescent devices include, but are not limited to, […].

[0247]

[0248] (RD)

[0249] .

[0250] In a more specific embodiment, the host material of the organic light-emitting layer 340 is the organic compound and RH-P of this application, and the guest material is RD.

[0251] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials. The electron transport materials can be selected from, but are not limited to, ET-01, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The materials of the electron transport layer 350 include, but are not limited to, the following compounds:

[0252]

[0253] (ET-01).

[0254] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-01 and LiQ.

[0255] In this application, the cathode 200 may include a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0256] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0257] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0258] According to one implementation method, such as Figure 2 As shown, the provided 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 including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0259] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0260] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0261] 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.

[0262] Synthesis Examples

[0263] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the organic compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. The compounds synthesized by methods not mentioned in this application are all commercially available starting materials.

[0264] Synthesis of intermediate Sub-a1:

[0265]

[0266] Under nitrogen protection, 8-bromo-2-hydroxynaphthalene (11.1 g, 50 mmol), benzylamine (10.71 g, 100 mmol), ammonium persulfate (22.82 g, 100 mmol), 2,2,6,6-tetramethylpiperidine oxide (TEMPO, 15.63 g, 100 mmol), and acetonitrile (150 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were initiated, and the mixture was heated to 50 °C and stirred for 24 h. After the reaction system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using ethyl acetate / n-heptane as the mobile phase to obtain a grayish-white solid (8.24 g, yield: 51%).

[0267] Following the synthetic method of Sub-a1, intermediates Sub-a2 to Sub-a6 were synthesized by replacing benzylamine with reactant A shown in Table 1.

[0268] Table 1: Synthesis of intermediates Sub-a2 and Sub-a6

[0269]

[0270] Synthesis of intermediate Sub-b1:

[0271]

[0272] Under nitrogen protection, Sub-a1 (16.15 g, 50 mmol), o-chloroaniline (6.35 g, 50 mmol), tris(dibenzylacetone)palladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (200 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the reaction system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid Sub-b1 (12.58 g; yield: 68%).

[0273] Referring to Sub-b1, reactant B shown in Table 2 was used to replace Sub-a1, and reactant C was used to replace o-chloroaniline to synthesize intermediates Sub-b2 to Sub-b9.

[0274] Table 2: Synthesis of intermediates Sub-b2 to Sub-b9

[0275]

[0276] Synthesis of intermediate Sub-c1:

[0277]

[0278] Under nitrogen protection, Sub-b1 (18.50 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol), and N,N-dimethylacetamide (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid, Sub-c1 (12.0 g; yield: 72%).

[0279] Referring to the synthesis of Sub-c1, reactant D shown in Table 3 was used to replace Sub-b1 to synthesize intermediates Sub-c2 to Sub-c9.

[0280] Table 3: Synthesis of intermediates Sub-c2 to Sub-c9

[0281]

[0282] Synthesis of intermediate Sub-d1:

[0283]

[0284] Under nitrogen protection, 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (15.85 g, 50 mmol), 5-chloro-1-naphthoboric acid (11.33 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (160 mL), tetrahydrofuran (40 mL), and deionized water (40 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the reaction system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid (18.16 g, yield: 82%).

[0285] Referring to the synthesis of Sub-d1, reactant E was used instead of 2-chloro-4-(2-naphthyl)-6-phenyl-1,3,5-triazine, and reactant F was used instead of 5-chloro-1-naphthoboric acid, as shown in Table 4, to synthesize intermediates Sub-d2 to Sub-d6.

[0286] Table 4: Synthesis of intermediates Sub-d2 to Sub-d6

[0287]

[0288] Synthesis of compound 4:

[0289]

[0290] Under nitrogen protection, Sub-Cl (16.70 g, 50 mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (25.73 g, 75 mmol), and dry DMF (500 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to -10 °C, and sodium hydroxide (60% content, 2.2 g, 55 mmol) was quickly added. The mixture was stirred overnight. The reaction solution was poured into 500 mL of deionized water, stirred thoroughly for 30 min, filtered, and the filtrate was washed with deionized water until neutral, then rinsed with anhydrous ethanol (200 mL) to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid compound 4 (24.36 g, yield: 76%, m / z = 642.22 [M+H)). + ).

[0291] Following the synthetic method of compound 4, reactant G was used instead of Sub-c1, and reactant H was used instead of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, as shown in Table 5, to synthesize the compounds shown in Table 5.

[0292] Table 5: Synthesis of the compounds in this application

[0293]

[0294] Synthesis of compound 158:

[0295]

[0296] Under nitrogen protection, Sub-d1 (24.37 g, 55 g) was added sequentially to a 500 mL three-necked flask. Sub-c1 (16.70 g, 50 mmol), tris(dibenzylacetone)palladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-Phos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (250 mL) were added to a solution. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water and stirred thoroughly for 30 min. The mixture was then filtered, and the filter cake was washed with deionized water until neutral, followed by washing with anhydrous ethanol (200 mL). The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid compound 158 (24.83 g, yield: 67%, m / z = 742.24 [M+H)).+ ).

[0297] Following the synthetic method of compound 158, the compounds shown in Table 6 were synthesized by replacing Sub-d1 with reactant J shown in Table 6.

[0298] Table 6: Synthesis of the compounds in this application

[0299]

[0300] The NMR data of some compounds are shown in Table 7 below.

[0301] Table 7

[0302]

[0303] Fabrication of organic electroluminescent devices

[0304] Example 1: Fabrication of a red organic electroluminescent device

[0305] The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 100Å / 1000Å / 100Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0306] On the experimental substrate (anode), PD:HT-22 was co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 Å. Then, HT-22 was vacuum-deposited onto the hole injection layer to form a first hole transport layer with a thickness of 1065 Å. Finally, compound HT-23 was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of 890 Å.

[0307] On the second hole transport layer, compound 4: RH-P:RD was co-deposited at a deposition rate of 49% : 49% : 2% to form an organic light-emitting layer (EML) with a thickness of 400 Å.

[0308] On the organic light-emitting layer, compound ET-01 and LiQ are co-deposited at a 1:1 evaporation rate to form a 350 Å thick electron transport layer (ETL). Yb is deposited on the electron transport layer to form a 10 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:9 evaporation rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.

[0309] Furthermore, compound CP-1 is vacuum-deposited onto the aforementioned cathode to form an organic coating layer with a thickness of 800 Å, thereby completing the fabrication of the red organic electroluminescent device.

[0310] Examples 2-37

[0311] Except that, when fabricating the light-emitting layer, compound Y from Table 8 is used instead of compound 4 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0312] Comparative Examples 1-3

[0313] Except that when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound 4 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0314] The structural formulas of the materials used in Examples 1-37 and Comparative Examples 1-3 are as follows:

[0315]

[0316] The performance of the red organic electroluminescent devices prepared in Examples 1-37 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 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0317] Table 8

[0318]

[0319] As shown in Table 8 above, the organic compounds of this application, when used as organic electroluminescent devices, improve current efficiency by at least 11.4% and T95 lifetime by at least 11.1% compared to Comparative Examples 1-3.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Formula 1 Among them, ring A is a benzene ring or a naphthalene ring; X1 is 0, X2 is ; L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene; The substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, halogen groups, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl. L3 is selected from single bond, unsubstituted phenylene, and unsubstituted naphthylene; L is selected from single bond, unsubstituted phenylene, or unsubstituted naphthylene; 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 phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted dibenzofuranyl; The substituents in Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, methyl, pentadeuterated phenyl, or phenyl. Each R1 and R2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, or phenyl; n1 represents the number of R1s, and n1 is selected from 0; n2 represents the number of R2, and n2 is selected from 0.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from compounds shown in Formula 1-1, Formula 1-2, Formula 1-3 or Formula 1-4:

3. The organic compound according to claim 1, characterized in that, and Each group is independently selected from the group consisting of the following groups: 。 4. The organic compound according to claim 1, characterized in that, Selected from the group consisting of the following groups: 。 5. An organic compound, characterized in that, The organic compound is selected from the group consisting of the following compounds: 。 6. An organic electroluminescent device, characterized in that, It includes an anode and a cathode arranged opposite to each other, and a functional layer disposed between the anode and the cathode; The functional layer comprises the organic compound as described in any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that, The functional layer includes an organic light-emitting layer; the organic light-emitting layer contains the organic compound.

8. The organic electroluminescent device according to claim 6, characterized in that, The organic electroluminescent device is a red organic electroluminescent device.

9. An electronic device, characterized in that, Includes the organic electroluminescent device according to any one of claims 6 to 8.

Images