Organic compounds, organic electroluminescent devices and electronic devices

Abstract

This application relates to the field of organic electroluminescent materials technology, providing an organic compound and an organic electroluminescent device and electronic device comprising the same. The compound of this application uses silanefluorenyl and carbazole as its core structure. When this compound is used as the host material of the light-emitting layer, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance the luminous efficiency and lifetime of the device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to organic compounds and organic electroluminescent devices and electronic devices containing the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Organic light-emitting diodes (OLEDs) 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, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, driving voltages also increase, and luminous efficiency and current efficiency need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] 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 same, wherein the organic compound used in the organic electroluminescent device can improve the performance of the device.

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

[0006]

[0007] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0008] L is a substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms;

[0009] Each of R1, R2, and R3 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, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0010] n1 is selected from 0, 1, 2, 3 or 4;

[0011] n2 is selected from 0, 1, 2, 3 or 4;

[0012] n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0013] The substituents in L, Ar1, and Ar2 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, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar2 form a ring.

[0014] 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.

[0015] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0016] The compound structure of this application contains a silane fluorene core connected to carbazole via a dibenzo5-membered ring. The silane fluorene core and the two substituents at position 9 are located in three different planes, resulting in a relatively large molecular twist and a high glass transition temperature, enabling the compound to form a good amorphous thin film. In particular, the connection between silane fluorene and carbazole via the dibenzo5-membered heterocycle gives the entire molecule a high first excited triplet energy level. When this compound is used as a hole transport material in a hybrid blue light-emitting substrate, on the one hand, the high first excited triplet energy level improves the energy transfer efficiency from the substrate to the blue light-emitting dopant, increasing the device's luminous efficiency; on the other hand, the high glass transition temperature ensures the formation of a good amorphous thin film and that the film morphology remains unchanged during long-term device operation, thus improving device lifetime. Attached Figure Description

[0017] 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.

[0018] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0019] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0020] Figure Labels

[0021] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0022] 321. Hole transport layer; 322. Electron blocking layer; 330. Organic light-emitting layer; 340. Electron transport layer

[0023] 350, Electron injection layer; 400, Electronic device Detailed Implementation

[0024] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of 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.

[0025] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0026]

[0027] Ar1 and Ar2 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms.

[0028] L is selected from substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;

[0029] Each of R1, R2, and R3 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, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms;

[0030] n1 is selected from 0, 1, 2, 3 or 4;

[0031] n2 is selected from 0, 1, 2, 3 or 4;

[0032] n3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0033] The substituents in L, Ar1, and Ar2 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, deuterated alkyl with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, triphenylsilyl, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 3 to 20 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents in Ar2 form a ring.

[0034] In this application, the terms "optionally" and "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, it includes both the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. As another example, "optionally, any two adjacent substituents in Ar2 form a ring" means that any two adjacent substituents in Ar2 are connected to each other to form a ring, or that any two adjacent substituents in Ar2 can exist independently. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0035] In this application, the descriptive phrases "each...independently is" and "...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 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.

[0036] 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, halogen groups, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, deuterylalkyl, deuterylaryl, haloaryl, cycloalkyl, etc. The number of substituents can be one or more.

[0037] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0038] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0039] 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 L is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0040] 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 single bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon single bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon single bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon single 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, phenyl-naphthyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthyl, etc. Base, etc.

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

[0042] In this application, terphenyl includes

[0043] 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.

[0044] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, or 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 40 carbon atoms; in other embodiments, it is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in still other embodiments, it is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; and in yet another embodiment, it is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0045] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0046] In this application, the aryl groups used as substituents for L, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0047] 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 single bonds in conjugation. Each 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, benzothiopheneyl, dibenzothiopheneyl, thiophenothiopheneyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiazinyl, silfluorenyl, dibenzofuranyl, etc.

[0048] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0049] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group (hybrid aryl group) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 40; in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 3 to 30; and in still other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with a total carbon number of 5 to 12.

[0050] In this application, the heteroaryl groups used as substituents for L, Ar1, and Ar2 include, but are not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenantholinyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzothiophene, and dibenzofuranyl.

[0051] 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.

[0052] 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.

[0053] In this application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.

[0054] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0055] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0056] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0057] In this application, deuterated aryl refers to an aryl group containing deuterium substitution, such as, but not limited to, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, etc.

[0058] In this application, halogenated aryl refers to an aryl group with a halogen substituent, such as, but not limited to, fluorophenyl, fluoronaphthyl, fluorobiphenyl, etc.

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

[0060] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects 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 traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0061]

[0062] For another example, as shown in equation (X'), the dibenzofuran 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 shown in equations (X'-1) to (X'-4) is included.

[0063]

[0064] In this application, a non-orienting 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-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0065]

[0066] In some embodiments, the organic compound is selected from the structures shown in formula (1-1), (1-2), or (1-3):

[0067]

[0068] In some embodiments, Ar2 is selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.

[0069] In some embodiments, Ar2 is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0070] In some embodiments, the substituents in Ar2 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, deuteralkyl with 6 to 12 carbon atoms, heteroaryl with 5 to 12 carbon atoms, and trialkylsilyl with 3 to 8 carbon atoms; optionally, any two adjacent substituents in Ar2 form a 5 to 13-membered ring.

[0071] In some embodiments, Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, and substituted or unsubstituted carbazoleyl.

[0072] Optionally, the substituents in Ar2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, phenanthryl, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl; optionally, any two adjacent substituents in Ar2 form a benzene ring or a fluorene ring.

[0073] In some embodiments, Ar2 is selected from substituted or unsubstituted groups V; wherein the unsubstituted group V is selected from the following groups:

[0074]

[0075] The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, 9,9-dimethylfluorenyl, phenanthryl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl. When the number of substituents on group V is greater than 1, the substituents may be the same or different.

[0076] In some embodiments, Ar2 is selected from the group consisting of:

[0077]

[0078] In some embodiments, Ar2 is selected from the group consisting of:

[0079]

[0080]

[0081] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6 to 21 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0082] In some embodiments, Ar1 is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 or 21 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0083] In some embodiments, the substituents in Ar1 are each independently selected from deuterium, halogen groups, cyano groups, haloalkyl groups with 1 to 4 carbon atoms, deuteralkyl groups with 1 to 4 carbon atoms, alkyl groups with 1 to 4 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, aryl groups with 6 to 12 carbon atoms, deuteralkyl groups with 6 to 12 carbon atoms, heteroaryl groups with 5 to 12 carbon atoms, or trialkylsilyl groups with 3 to 8 carbon atoms.

[0084] In some embodiments, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiopheneyl.

[0085] Optionally, the substituents in Ar1 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, pentadeuterated phenyl, or naphthyl.

[0086] In some embodiments, Ar1 is selected from the group consisting of:

[0087]

[0088]

[0089] In some embodiments, Ar1 is selected from the group consisting of:

[0090]

[0091] In some embodiments, L is selected from substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms.

[0092] In some embodiments, L is selected from substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0093] Optionally, the substituents in L are each independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, trialkylsilyl with 3 to 8 carbon atoms, fluoroalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, phenyl, pentadeuterated phenyl, biphenyl or naphthyl.

[0094] In some embodiments, L is selected from substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted carbazolyl.

[0095] Optionally, the substituents in L may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, pentadeuterated phenyl, biphenyl or naphthyl.

[0096] In some embodiments, L is selected from the group consisting of:

[0097]

[0098] In some embodiments, L is selected from the group consisting of:

[0099]

[0100] In some embodiments, each of R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, cyano, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, phenyl, pentadeuterated phenyl, biphenyl, or naphthyl.

[0101] In some embodiments, the organic compounds of this application are selected from the group consisting of:

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] A second aspect of this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.

[0111] The organic compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0112] Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.

[0113] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked sequentially.

[0114] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0115] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0116]

[0117]

[0118] In one embodiment, the hole transport layer 321 may be composed of a BCFN.

[0119] In one embodiment, the electron blocking layer 322 is composed of SiCzCz.

[0120] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. The material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof;

[0121]

[0122] In one embodiment, the hole injection layer 310 is composed of HATCN.

[0123] In this application, the organic light-emitting layer 330 can be composed of a single light-emitting material, or it can include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0124] The host material of the organic light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises the organic compounds of this application. In some embodiments, the host light-emitting layer comprises the organic compounds of this application and BH-N.

[0125] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to,

[0126] In one embodiment of this application, the organic electroluminescent device is a blue organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application. The guest material is, for example, BD. In another embodiment, there is...

[0127] It is BD.

[0128] In one embodiment of this application, the organic electroluminescent device is a blue organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the organic compound of this application.

[0129] The electron transport layer 340 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, BTB, LiQ, mSiTrz, 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 340 include, but are not limited to, the following compounds:

[0130]

[0131] In one embodiment of this application, the electron transport layer 340 may be composed of mSiTrz and LiQ.

[0132] 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.

[0133] Optionally, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).

[0134] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0135] 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.

[0136] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.

[0137] Synthesis Examples

[0138] 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.

[0139] Synthesis of Sub-a1:

[0140]

[0141] Under a nitrogen atmosphere, 3-bromocarbazole (12.25 g, 50 mmol), RM-1 (27.55 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol), and N,N-dimethylformamide (280 mL) were added sequentially to a 500 mL three-necked flask. 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, filtered, and the filtrate was collected. The filtrate was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, 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 (18.70 g; yield 65%).

[0142] Referring to the synthesis of Sub-a1, Sub-a2 was synthesized by replacing 3-bromocarbazole with reactant A shown in Table 1 and replacing RM-1 with reactant B.

[0143] Table 1: Synthesis of Sub-a2

[0144]

[0145] Synthesis of Sub-b1:

[0146]

[0147] Under a nitrogen atmosphere, RM-2 (33.10 g, 70 mmol) and tetrahydrofuran (dried, 250 mL) were added to a 500 mL three-necked flask. The system was cooled to -78 °C, and a solution of n-butyllithium (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour. While maintaining the low temperature of -78 °C, trimethyl borate (10.91 g, 105 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C for another 1 hour, and then the system was allowed to warm up to room temperature naturally. Add dilute hydrochloric acid (2M, 58mL) dropwise to the reaction solution and stir for 30 minutes; extract with dichloromethane (100mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain crude product; slurry the crude product with n-heptane and filter to obtain white solid product Sub-b1 (19.0g, yield 62%).

[0148] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b3 were synthesized by replacing Sub-a1 with reactant C shown in Table 2 and replacing 7-bromo-1-iodo-2-hydroxynaphthalene with reactant C.

[0149] Table 2: Synthesis of Sub-b2 to Sub-b11

[0150]

[0151] Synthesis of Sub-c1:

[0152]

[0153] Under a nitrogen atmosphere, deuterated bromobenzene (8.05 g, 50 mmol) and tetrahydrofuran (dried, 80 mL) were added sequentially to a 500 mL three-necked flask. The system was cooled to -78 °C, and n-butyllithium solution (2.0 M n-hexane solution, 25 mL, 50 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour. RM-3 (12.5 g, 50 mmol) in tetrahydrofuran solution (125 mL) was added dropwise. After the addition was complete, the system was kept at -78 °C for another 1 hour, and then allowed to warm to room temperature naturally. The solvent was removed by filtration and vacuum distillation to obtain the crude product. The crude product was used directly in the next reaction without purification.

[0154] Sub-c2 to Sub-c6 were synthesized by replacing deuterated bromobenzene with reactant D as shown in Table 3, referring to Sub-c1.

[0155] Table 3: Synthesis of Sub-c2 to Sub-c6

[0156]

[0157] Synthesis of Sub-d1:

[0158]

[0159] Under a nitrogen atmosphere, 14.0 g (50 mmol) of 3-bromo-6-chlorodibenzofuran and 80 mL (dried) of tetrahydrofuran were added sequentially to a 500 mL three-necked flask. The system was cooled to -78 °C, and 25 mL (50 mmol) of 2.0 M hexane solution was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour. 150 mL of RM-4 (14.6 g, 50 mmol) of tetrahydrofuran solution was added dropwise. After the addition was complete, the system was kept at -78 °C for another hour, and then allowed to warm to room temperature naturally. The system was extracted with dichloromethane (100 mL × 3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate. The mixture was 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 dichloromethane / n-heptane as the mobile phase to obtain a white solid compound (15.35 g, yield 67%).

[0160] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d22 were synthesized by replacing RM-4 with reactant E shown in Table 4 and replacing 3-bromo-6-chlorodibenzofuran with reactant F.

[0161] Table 4: Synthesis of Sub-d2 to Sub-d26

[0162]

[0163]

[0164]

[0165] Synthesis of compound 14:

[0166]

[0167] Under a nitrogen atmosphere, Sub-d1 (9.16 g, 20 mmol), (9-phenyl-9H-carbazole-4-yl)boric acid (6.32 g, 22 mmol), palladium acetate (Pd(OAc)2, 0.045 g, 0.2 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (XPhos, 0.19 g, 0.4 mmol), anhydrous potassium carbonate (5.53 g, 40 mmol), toluene (100 mL), tetrahydrofuran (25 mL), and deionized water (25 mL) were added sequentially to a 250 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 16 h. After the 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 dichloromethane / n-heptane as the mobile phase to give compound 2 (10.7 g, yield 78%, m / z = 666.2 [M+H)) as a white solid. + ).

[0168] Referring to the synthesis of compound 14, reactant G was used instead of Sub-d1, and reactant H was used instead of 9-phenyl-9H-carbazole-4-yl)boronic acid as shown in Table 5 to synthesize the compounds of this application in Table 5.

[0169] Table 5: Synthesis of the compounds in this application

[0170]

[0171]

[0172]

[0173]

[0174] Synthesis of compound 229:

[0175]

[0176] Under a nitrogen atmosphere, RM-5 (14.0 g, 25 mmol) and tetrahydrofuran (dry, 80 mL) were added sequentially to a 250 mL three-necked flask. The system was cooled to -78 °C, and a solution of n-butyllithium (2.0 M n-hexane solution, 12.5 mL, 25 mmol) was added dropwise. After the addition was complete, the system was kept at -78 °C and stirred for 1 hour. RM-4 (7.3 g, 25 mmol) in a tetrahydrofuran solution (75 mL) was added dropwise. After the addition was complete, the system was kept at -78 °C for another 1 hour, and then allowed to warm to room temperature naturally. The system was extracted with dichloromethane (100 mL × 3 times), and 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 dichloromethane / n-heptane as the mobile phase to obtain a white solid compound 229 (8.80 g, yield 53%, m / z = 665.2 [M+H)). + ).

[0177] Referring to the synthesis of compound 229, the compounds of this application in Table 6 were synthesized by replacing RM-5 with reactant J shown in Table 6.

[0178] Table 6: Synthesis of compounds 239 and 242 of this application

[0179]

[0180] NMR of Compound 19: 1 H-NMR(400MHz,Methylene-Chloride-D2)δppm 8.03(d,2H),7.95(d,1H),7.91-7.87(m,2H),7.79-7371(m,5H),7.60-7.46(m,11H),7.43-7.25(m,10H).

[0181] Fabrication and evaluation of organic electroluminescent devices:

[0182] Example 1: Blue Organic Electroluminescent Device

[0183] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0184] HATCN was vacuum-deposited on the experimental substrate (anode) to form a thickness of [thickness value missing]. A hole injection layer (HIL) is formed, and then BCFN is vacuum-deposited on the hole injection layer to form a thickness of [thickness value missing]. The hole transport layer.

[0185] Next, SiCzCz is vacuum-deposited on the hole transport layer to form a thickness of [thickness value missing]. An electron blocking layer (EBL) was formed, and then compound 14:BH-N:BD was co-deposited at a rate of 60%:27%:13% to form a thickness of [missing information]. The blue light-emitting layer (EML).

[0186] On the light-emitting layer, compounds mSiTrz and LiQ are mixed in a 1:1 weight ratio and deposited by vapor deposition to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron injection layer (EIL) is formed, and then aluminum (Al) is vacuum-deposited onto the electron injection layer to form a layer with a thickness of [missing information]. The cathode is used to complete the fabrication of the blue organic electroluminescent device.

[0187] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0188]

[0189]

[0190] Examples 2-25

[0191] Except that, when fabricating the light-emitting layer, compound X in Table 7 is used instead of compound 14 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0192] Comparative Examples 1-3

[0193] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound 14 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0194] The performance of the blue organic electroluminescent devices prepared in Examples 1-25 and Comparative Examples 1-3 was tested. Specifically, the voltage, efficiency and lifetime characteristics of the devices were tested at a brightness of 1000 nits. The test results are shown in Table 7.

[0195] Table 7

[0196]

[0197]

[0198] As can be seen from Table 7 above, when the compounds of the present invention are used as the host material for blue organic electroluminescent devices, the efficiency is increased by at least 14.6% and the lifetime is increased by at least 15.2%.

[0199] The reason for this is that the compound structure contains a silane fluorene core connected to carbazole via a heteroaryl group. The silane fluorene core and the two substituents at position 9 are located in three different planes, resulting in a relatively large molecular twist and a high glass transition temperature, enabling the compound to form a good amorphous thin film. Furthermore, the silane fluorene and carbazole are connected by a dibenzo-5-membered ring, giving the entire molecule a high first excited triplet energy level. When this compound is used as a hole transport host material in a hybrid blue light host material, on the one hand, the high first excited triplet energy level improves the energy transfer efficiency from the host material to the blue light dopant, thus increasing the device's luminous efficiency; on the other hand, the high glass transition temperature ensures the formation of a good amorphous thin film in the light-emitting layer, thereby improving the device's lifetime.

[0200] The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings. However, the present invention is not limited to the specific details of the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the protection scope of the present invention.

Claims

1. An organic compound, characterized in that, It has the structure shown in Equation 1: Ar1 is selected from the group consisting of the following groups: Ar2 is selected from substituted or unsubstituted groups V; wherein, the unsubstituted group V is selected from the following groups: The substituted group V has one or more substituents, each of which is independently selected from deuterium, trimethylsilyl, trideuterated methyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazoyl, and when the number of substituents on group V is greater than 1, the substituents may be the same or different. L is selected from substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, or substituted or unsubstituted carbazolyl; The substituents in L may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, trimethylsilyl, phenyl, pentadeuterated phenyl, biphenyl or naphthyl; Each of R1, R2, and R3 may be the same or different, and each is independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, and pentadeuterated phenyl; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1, 2, 3 or 4; n3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7.

2. The organic compound of claim 1, wherein, Ar2 is selected from the group consisting of the following groups:

3. The organic compound according to claim 1, wherein, Ar1 is selected from substituted or unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted dibenzofuranyl, and unsubstituted dibenzothiopheneyl. The substituents in Ar1 are each independently selected from deuterium.

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

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

6. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises the organic compound according to 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, which contains the organic compound.

8. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 6 or 7.

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