Organic compounds, organic electroluminescent devices and electronic devices

Abstract

This application belongs to the field of organic electroluminescence technology, and relates to an organic compound and an organic electroluminescent device and electronic device using the same. The organic compound has a structure as shown in Formula 1. Using the organic compound in an organic electroluminescent device can significantly improve the performance of the organic electroluminescent device.

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] In this case, one of X and Y is O, and the other is... ;

[0009] L1 and L2 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.

[0010] 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.

[0011] The substituents in L1, L2, 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, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl 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;

[0012] Each R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 5 to 18 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0013] n1 represents the number of R1s, which can be selected from 0, 1, or 2. When n1 is greater than 1, all R1s may be the same or different.

[0014] 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.

[0015] 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.

[0016] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0017] The core structure of the organic compound in this application is a group formed by the simultaneous fusion of oxazole and benzofuran groups onto a phenyl group in a specific manner. This group, combined with a triazine group, yields the novel compound of this application. This type of structure exhibits a high aromatic conjugation effect, resulting in high electron mobility, and consequently, excellent energy transport characteristics, more suitable energy level characteristics, and high molecular structural stability. When this type of compound is applied to the organic light-emitting layer in an organic electroluminescent device, it can effectively improve the device's driving voltage and luminous efficiency while maintaining good lifetime characteristics.

[0018] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0019] 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.

[0020] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0021] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0022] Figure Labels

[0023] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0024] 320, First hole transport layer; 330, Second hole transport layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0025] 360°, electron injection layer 400°, electronic device Detailed Implementation

[0026] 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.

[0027] According to a first aspect of this application, an organic compound is provided having a structure as shown in Formula 1:

[0028]

[0029] Formula 1

[0030] In this case, one of X and Y is O, and the other is... ;

[0031] L1 and L2 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.

[0032] 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.

[0033] The substituents in L1, L2, 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, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl 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;

[0034] Each R1 and R2 may be the same or different, and each is independently selected from deuterium, halogen group, cyano, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, deuterated aryl with 6 to 20 carbon atoms, haloaryl with 6 to 20 carbon atoms, heteroaryl with 5 to 18 carbon atoms, or cycloalkyl with 3 to 10 carbon atoms;

[0035] n1 represents the number of R1s, which can be selected from 0, 1, or 2. When n1 is greater than 1, all R1s may be the same or different.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0040] 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.

[0041] 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.

[0042] In this application, terphenyl includes and .

[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 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.

[0045] 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.

[0046] In this application, aryl groups used as substituents for L, L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, 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 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0052] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0053] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0054] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0055] 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.

[0056] 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.

[0057]

[0058] .

[0059] 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.

[0060] .

[0061] In some embodiments of this application, X is O, and Y is .

[0062] In other embodiments of this application, X is Y is O.

[0063] In some embodiments of this application, the organic compound is selected from compounds represented by formula A or formula B:

[0064]

[0065] In some embodiments of this application, the organic compound is selected from compounds represented by Formula 1-1, Formula 1-2, Formula 1-3, or Formula 1-4:

[0066]

[0067] In some embodiments of this application, the organic compound is selected from compounds represented by formula A1, A2, A3, A4, A5, A6, B1, B2, B3, B4, B5, or B6:

[0068]

[0069] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0070] Optionally, the substituents in L1 and L2 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.

[0071] 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 12 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 18 carbon atoms, respectively.

[0072] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0073] Optionally, 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.

[0074] 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:

[0075]

[0076] 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.

[0077] 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:

[0078]

[0079] .

[0080] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups with 12 to 24 carbon atoms.

[0081] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and may be 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.

[0082] In other embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophene.

[0083] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl.

[0084] 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 groups W are selected from the group consisting of:

[0085]

[0086]

[0087] 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.

[0088] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0089]

[0090]

[0091]

[0092]

[0093] .

[0094] Specifically, Ar1 and Ar2 may be the same or different, and are each independently selected from the group consisting of the following groups:

[0095]

[0096]

[0097]

[0098]

[0099] .

[0100] In some embodiments of this application, Ar3 is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

[0101] Optionally, the substituents in the Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, alkyl with 1 to 5 carbon atoms, pentadeuterated phenyl or phenyl.

[0102] In some embodiments of this application, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl.

[0103] Optionally, the substituents in the 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.

[0104] Specifically, Ar3 is selected from the group consisting of the following groups:

[0105] .

[0106] In some embodiments of this application, and Each group is independently selected from the group consisting of the following groups:

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] .

[0113] Specifically, and Each group is independently selected from the group consisting of the following groups:

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] .

[0120] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129] .

[0130] Specifically, in Equation 1 Selected from the group consisting of the following groups:

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] .

[0141] 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.

[0142] In some embodiments of this application, both n1 and n2 are 0.

[0143] In some embodiments of this application, the organic compound is selected from the group consisting of:

[0144]

[0145] 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.

[0146] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device.

[0147] In other embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device.

[0148] like Figure 1As 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.

[0149] 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.

[0150] 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 on this selection. In some embodiments of this application, the first hole transport layer 320 is HT-24, and the second hole transport layer 330 is HT-23 or HT-25.

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] .

[0157] 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;

[0158]

[0159]

[0160]

[0161] In some embodiments of this application, the hole injection layer 310 is composed of PD and HT-24.

[0162] 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.

[0163] 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.

[0164] In one embodiment of this application, the organic light-emitting layer 340 contains the organic compounds of this application.

[0165] Optionally, the organic compound of this application is used as the host material (electronic host material) of the organic light-emitting layer 340.

[0166] In some embodiments of this application, the hole-type host material of the organic light-emitting layer 340 is... (GH-P) or (RH-P)

[0167] The guest material of the organic light-emitting layer 340 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 restrictions on this. The guest material is also called a dopant or dopant.

[0168] Specific examples of green phosphorescent dopants used in green organic electroluminescent devices include, but are not limited to, those used in other green organic electroluminescent devices.

[0169]

[0170]

[0171] (GD).

[0172] Specific examples of red phosphorescent dopants used in red organic light-emitting devices include, but are not limited to, those used in red organic light-emitting devices.

[0173] (RD)

[0174]

[0175] .

[0176] In a more specific embodiment, the host material of the organic light-emitting layer 340 is the organic compound of this application and RH-P, and the guest material is RD.

[0177] In another, more specific embodiment, the host material of the organic light-emitting layer 340 is the organic compound of this application and GH-P, and the guest material is GD.

[0178] 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:

[0179]

[0180]

[0181] (ET-1).

[0182] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-1 and LiQ.

[0183] 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.

[0184] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0185] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0186] 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.

[0187] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0188] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0189] 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.

[0190] Synthesis Examples

[0191] 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.

[0192] Synthesis of intermediate a1-o:

[0193]

[0194] 3-Bromo-2-chlorodibenzofuran (15.0 g; 53.3 mmol), cuprous iodide (1.0 g; 5.3 mmol), 8-hydroxyquinalidine (1.7 g; 10.7 mmol), tetrabutylammonium hydroxide (41.5 g; 159.8 mmol), dimethyl sulfoxide (150 mL), and deionized water (200 mL) were added to a round-bottom flask under nitrogen protection, and the mixture was heated to 125 °C with stirring. o C-130 o C, react for 36 hours; cool to room temperature, add dichloromethane (500 mL) and deionized water (500 mL) to the reaction solution, separate the layers, wash the organic phase with water and dry with anhydrous magnesium sulfate, remove the solvent under reduced pressure; the crude product is purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate a1-o (8.4 g; yield: 72%).

[0195] Referring to the synthetic method of intermediate a1-o, reactant A in Table 1 was substituted for 3-bromo-2-chlorodibenzofuran to synthesize the intermediates shown in Table 1 below:

[0196] Table 1

[0197]

[0198] Synthesis of intermediate a1-c:

[0199]

[0200] Intermediate a1-o (8.1 g; 37.2 mmol), benzylamine (8.0 g; 74.3 mmol), 2,2,6,6-tetramethylpiperidine oxide (11.6 g; 74.3 mmol), ammonium persulfate (17.0 g; 74.3 mmol), and acetonitrile (70 mL) were added to a round-bottom flask under nitrogen protection and stirred at 50 °C.o C-55 o The reaction was carried out at C for 72 hours; then cooled to room temperature, and dichloromethane (150 mL) and deionized water (200 mL) were added to the reaction solution. The mixture was separated, and the organic phase was washed with water and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to obtain a white solid intermediate a1-c (5.0 g; yield: 42%).

[0201] Referring to the synthetic method of intermediate a1-c, reactant B in Table 2 was used to replace intermediate a1-o, and reactant N was used to replace aniline to synthesize the intermediates shown in Table 2 below:

[0202] Table 2

[0203]

[0204] Synthesis of intermediate a1-b:

[0205]

[0206] Intermediate a1-c (4.9 g; 15.3 mmol), pinacol diboronate (5.8 g; 23.0 mmol), tris(dibenzylacetone)palladium (0.1 g; 0.2 mmol), 2-dicyclohexylphospho-2',4',6'-triisopropylbiphenyl (0.1 g; 0.3 mmol), potassium acetate (2.3 g; 23.0 mmol), and 1,4-dioxane (50 mL) were added to a round-bottom flask under nitrogen protection and stirred at 100 °C. o C-105 o The reaction was carried out at C for 24 hours; then cooled to room temperature, and dichloromethane (100 mL) and deionized water (150 mL) were added to the reaction solution. The mixture was separated, the organic phase was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as solvent to obtain a white solid intermediate a1-b (4.7 g; yield: 75%).

[0207] Referring to the synthesis method of intermediate a1-b, reactant C in Table 3 was used to replace intermediate a1-c to synthesize the intermediates shown in Table 3 below:

[0208] Table 3

[0209]

[0210] Synthesis of compound A1-1:

[0211]

[0212] Intermediate a1-b (4.5 g; 10.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g; 11.5 mmol), tetratriphenylphosphine palladium (0.3 g; 0.2 mmol), potassium carbonate (3.0 g; 21.9 mmol), tetrabutylammonium bromide (0.7 g; 2.2 mmol), toluene (40 mL), ethanol (10 mL), and deionized water (10 mL) were added to a round-bottom flask under nitrogen protection, and the mixture was heated to 75°C. o C-80 o C. Stir the reaction mixture for 16 hours; cool the reaction mixture to room temperature, add deionized water (80 mL), separate the layers, wash the organic phase with water, dry with anhydrous magnesium sulfate, and remove the solvent under reduced pressure; purify the crude product by silica gel column chromatography using a toluene / n-heptane solvent system, and then recrystallize it using a toluene / n-heptane solvent system to obtain a white solid compound A1-1 (3.8 g; yield: 67%).

[0213] Following the synthetic method of compound A1-1, by replacing intermediate a1-b with reactant D in Table 4 and 2-chloro-4,6-diphenyl-1,3,5-triazine with reactant E, the compounds shown in Table 4 were synthesized:

[0214] Table 4

[0215]

[0216] Mass spectrometry data of some compounds are shown in Table 5 below.

[0217] Table 5

[0218]

[0219] The NMR data of some compounds are shown in Table 6 below.

[0220] Table 6

[0221]

[0222] Fabrication of organic electroluminescent devices

[0223] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0224] The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 110Å / 1100Å / 90Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate is cleaned with organic solvent to remove impurities and oil stains.

[0225] On the experimental substrate (anode), PD:HT-24 were co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 120 Å. Then, HT-24 was vacuum-deposited on the hole injection layer to form a first hole transport layer with a thickness of 1150 Å.

[0226] Compound HT-23 was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of 350 Å.

[0227] On the second hole transport layer, compounds A1-1:GH-P:GD were co-deposited at a deposition rate of 47%:47%:6% to form an organic light-emitting layer (green light-emitting layer) with a thickness of 340 Å.

[0228] On the organic light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and vapor-deposited to form a 335 Å thick electron transport layer (ETL). Yb is vapor-deposited on the electron transport layer to form a 15 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:9 vapor deposition rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.

[0229] In addition, CP-1 is vacuum-deposited on the cathode to form an organic coating layer with a thickness of 810 Å, thereby completing the fabrication of the green organic electroluminescent device.

[0230] Examples 2-23

[0231] Organic electroluminescent devices were prepared using the same method as in Example 1, except that the compounds listed in Table 7 (collectively referred to as "Compound X") were used instead of Compound A1-1 in Example 1 when fabricating the light-emitting layer.

[0232] Comparative Examples 1-4

[0233] Except that, when fabricating the light-emitting layer, compounds I, II, III, and IV were used instead of compound A1-1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0234]

[0235] The performance of the green organic electroluminescent devices prepared in Examples 1-23 and Comparative Examples 1-4 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 15 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.

[0236] Table 7

[0237]

[0238] As can be seen from Table 7 above, compared with Comparative Examples 1 to 4, when the compound of this application is used as the host material of green organic electroluminescent device, the current efficiency of the device is increased by at least 12.8% and the T95 lifetime is increased by at least 14.7%.

[0239] When the organic compounds of this application are used as light-emitting layer materials in green organic electroluminescent devices, they exhibit relatively lower driving voltages and higher efficiencies compared to compounds I and III. This is likely due to the direct connection between the triazine and the rigid core structure in these organic compounds, which allows for a wider conjugation range in the molecular structure. Furthermore, compared to compounds II and IV, the organic compounds of this application demonstrate higher efficiency at similar driving voltages. This is likely due to the higher first triplet energy level of the molecular structure resulting from the specific fusion mode between the groups in the core structure. In particular, the performance is optimal when the triazine group is attached to a benzene ring containing a fused oxazole.

[0240] Example 24: Fabrication of a red organic electroluminescent device

[0241] The anode pretreatment is first carried out through the following process: On ITO / Ag / ITO substrates with thicknesses of 110Å / 1000Å / 100Å respectively, the surface is treated with ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO / Ag / ITO substrate is cleaned with organic solvent to remove impurities and oil stains from the substrate surface.

[0242] On the experimental substrate (anode), PD:HT-24 was co-deposited at a deposition rate of 2%:98% to form a hole injection layer (HIL) with a thickness of 115 Å. Then, HT-24 was vacuum-deposited on the hole injection layer to form a first hole transport layer with a thickness of 1250 Å.

[0243] Compound HT-25 was vacuum-deposited onto the first hole transport layer to form a second hole transport layer with a thickness of 680 Å.

[0244] On the second hole transport layer, RH-P:compound A1-21:RD were co-deposited at a deposition rate of 49%:49%:2% to form an organic light-emitting layer (red light-emitting layer) with a thickness of 400 Å.

[0245] On the organic light-emitting layer, compound ET-1 and LiQ are mixed in a 1:1 weight ratio and vapor-deposited to form a 335 Å thick electron transport layer (ETL). Yb is vapor-deposited on the electron transport layer to form a 15 Å thick electron injection layer (EIL). Then, magnesium (Mg) and silver (Ag) are mixed at a 1:9 vapor deposition rate and vacuum-deposited on the electron injection layer to form a 130 Å thick cathode.

[0246] In addition, CP-1 is vacuum-deposited on the cathode to form an organic coating layer with a thickness of 800 Å, thereby completing the fabrication of the red organic electroluminescent device.

[0247] Examples 25-31

[0248] Organic electroluminescent devices were prepared using the same method as in Example 1, except that the compounds listed in Table 8 below (collectively referred to as "Compound X") were used instead of Compounds A1-21 in Example 1 when fabricating the light-emitting layer.

[0249] Comparative Examples 5-6

[0250] Except that compounds V and VI were used instead of compounds A1-21 in Example 20 when fabricating the light-emitting layer, the organic electroluminescent device was prepared using the same method as in Example 1.

[0251] The main compound structures used in the preparation of each example and comparative example are as follows:

[0252]

[0253] The performance of the red organic electroluminescent devices prepared in Examples 24-31 and Comparative Examples 4 and 5 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 15 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 8.

[0254] Table 8

[0255]

[0256] When the organic compounds of this application are used as the light-emitting layer material in a red organic electroluminescent device, compared with Comparative Examples 5 and 6, the current efficiency is increased by at least 19.0%, the lifetime is increased by at least 11.1%, and the driving voltage is reduced by at least 0.13V.

[0257] Compared to compound V, when the organic compounds of this application are used as the host material layer of the light-emitting layer in organic electroluminescent devices, the devices can have significantly lower driving voltage, higher efficiency, and longer T95 lifetime. The reason for this may be that triazine, as an electron transport group, has a higher aromatic conjugation effect and photoelectric stability than pyrimidine.

[0258] Compared to compound VI, when the organic compounds of this application are used as the main material layer of the light-emitting layer in organic electroluminescent devices, the devices can achieve higher luminous efficiency while maintaining a lower driving voltage. The reason for this may be that the special fusion mode between the specific groups in the core structure of the organic compounds of this application results in a higher first triplet energy level and a better match between the LUMO energy level and the adjacent layers.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Formula 1 In this case, one of X and Y is O, and the other 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, 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. 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 triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene. The substituents in Ar1 and Ar2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentadeuterated phenyl or phenyl; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl; The substituents in 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; Each R1 and R2 is the same, and is selected from deuterium; n1 represents the number of R1s, which can be selected from 0, 1, or 2. When n1 is greater than 1, all R1s may be the same or different. 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.

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, In Equation 1 Selected from the group consisting of the following groups: 。 5. The organic compound according to claim 1, characterized in that, The organic compounds are 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 5, 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 5, characterized in that, The organic electroluminescent device is a green / 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.

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