Organic compound, organic electroluminescence device, and electronic device

Abstract

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

Description

Technical Field

[0001] This application relates to the field of organic electroluminescence technology, and more specifically, to an organic compound and an organic electroluminescent device and electronic apparatus using the same. Background Technology

[0002] In recent years, self-emissive organic light-emitting diodes (OLEDs), which can be driven by low voltage, have attracted much attention as a next-generation display element compared to mainstream flat panel displays, namely liquid crystal displays (LCDs), due to their superior performance in viewing angle and contrast, ease of achieving thinner and lighter designs without the need for backlights, low power consumption, and wide color reproduction range. To date, many materials suitable for use in OLEDs have been disclosed. However, OLEDs using currently known materials are not easily commercialized due to their high driving voltage, low efficiency, and short lifespan. Therefore, it is necessary to develop materials with excellent properties to achieve OLEDs that can be driven by low voltage while possessing high brightness and long lifespan. Summary of the Invention

[0003] The purpose of this application is to provide an organic compound and an organic electroluminescent device and electronic device using the same, which have high luminous efficiency and long service life.

[0004] To achieve the above objectives, the first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0005]

[0006] Among them, 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 12 to 30 carbon atoms.

[0007] Ar1 and Ar2 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 12 to 40 carbon atoms, respectively.

[0008] 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, aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0009] n1 represents the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, any two R1s are the same or different.

[0010] n2 represents the number of substituents R2, and n2 is selected from 0, 1 or 2. When n2 is greater than 1, any two R2s are the same or different.

[0011] n3 represents the number of substituents R3, and n3 is selected from 0, 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different.

[0012] The substituents in L1, L2, 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, aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0013] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0014] A second aspect of 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 comprises the organic compound described in the first aspect of this application;

[0015] Preferably, the functional layer includes an organic light-emitting layer, the organic light-emitting layer containing the organic compound;

[0016] Preferably, the organic electroluminescent device is a red organic electroluminescent device.

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

[0018] The organic compound structure of this application contains a dibenzoindolo[3,2-B]carbazole with specific fusion positions. The two benzene rings are fused with indolo[3,2-B]carbazole via carbon atoms at positions 1,2 and 7,8, respectively. This unique fusion method endows the dibenzoindolo[3,2-B]carbazole core with a large conjugated area, facilitating intermolecular stacking and thus improving the compound's hole transport performance. Furthermore, this specific fusion method ensures the compound possesses a suitable first excited triplet energy level, making it suitable for use as a host material for the luminescent layer (especially for hole-transporting materials in hybrid red light). Therefore, using the compound of this application as a hole-transporting material in hybrid red light host materials can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and ultimately enhance the device's luminous efficiency and lifetime.

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

[0020] The accompanying drawings are provided to further illustrate the present application and form part of the specification. They are used together with the following detailed description to explain the present application, but do not constitute a limitation thereof. In the drawings:

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

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

[0023] Figure Labels

[0024] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0025] 320, Hole transport layer 320, First hole transport layer 330, Second hole transport layer 340, Organic light-emitting layer

[0026] 350, Electron transport layer; 360, Electron injection layer; 400, Electronic device Detailed Implementation

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

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

[0029]

[0030] Among them, 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 12 to 30 carbon atoms.

[0031] Ar1 and Ar2 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 12 to 40 carbon atoms, respectively.

[0032] 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, aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0033] n1 represents the number of substituents R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6. When n1 is greater than 1, any two R1s are the same or different.

[0034] n2 represents the number of substituents R2, and n2 is selected from 0, 1 or 2. When n2 is greater than 1, any two R2s are the same or different.

[0035] n3 represents the number of substituents R3, and n3 is selected from 0, 1, 2, 3, 4, 5 or 6. When n3 is greater than 1, any two R3s are the same or different.

[0036] The substituents in L1, L2, 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, aryl with 6 to 20 carbon atoms, heteroaryl with 12 to 20 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms;

[0037] Optionally, any two adjacent substituents in Ar1 and Ar2 can form a ring.

[0038] In this application, the terms "optional" or "optionally" mean that the event or situation described below may occur but does not have to occur, and the description includes the possibility that the event or situation may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may form a ring but are not required to form a ring, including both scenarios where the two adjacent substituents form a ring and scenarios where the two adjacent substituents do not form a ring.

[0039] In this application, the phrase "any two adjacent substituents forming a ring" can include two substituents on the same atom, or one substituent on each of two adjacent atoms. When two substituents are on the same atom, the two substituents can form a saturated or unsaturated ring with the atom they are connected to. When one substituent is on each of two adjacent atoms, the two substituents can fuse into a ring. For example, when Ar1 contains two or more substituents, the formation of a ring by any two adjacent substituents results in a saturated or unsaturated cyclic group, such as benzene rings, naphthalene rings, phenanthrene rings, anthracene rings, fluorene rings, cyclopentane, cyclohexane, adamantane, etc.

[0040] In this application, the fluorene group can be replaced by one or two substituents. Specifically, when the fluorene group is replaced, the following substitutions can be made: etc., but not limited to this.

[0041] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In 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.

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

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

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

[0045] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. Aryl, spirodifluorenyl, etc. In this application, the aryl group refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0046] In this application, terphenyl includes

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

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 25, or 30. 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 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms.

[0049] In this application, aryl groups used as substituents for L1, L2, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, etc.

[0050] 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.

[0051] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl group can be selected from 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 24 carbon atoms, while in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group with 12 to 18 carbon atoms.

[0052] 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 in the heteroaryl group and the substituents on the heteroaryl group.

[0053] 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.

[0054] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0055] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl groups.

[0056] In this application, specific examples of alkyl halogens include, but are not limited to, trifluoromethyl.

[0057] In this application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0058] 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.

[0059] 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 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.

[0060]

[0061] For 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.

[0062]

[0063] In some embodiments of this application, R1, R2, or R3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, or tert-butyl.

[0064] In some embodiments of this application, L1 and L2 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 15 carbon atoms, and substituted or unsubstituted heteroaryl groups with 12 to 20 carbon atoms.

[0065] 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.

[0066] In other 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 biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazolyl.

[0067] Optionally, the substituents in L1 and L2 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0068] 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:

[0069]

[0070] 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.

[0071] Specifically, L1 and L2 may be the same or different, and are independently selected from the group consisting of single bonds or groups of the following:

[0072]

[0073] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 24 carbon atoms.

[0074] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups or phenyl groups having 1 to 5 carbon atoms;

[0075] Optionally, in Ar1 and Ar2, any two adjacent substituents form a fluorene ring.

[0076] 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 fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, and substituted or unsubstituted spirodifluorenyl.

[0077] Optionally, the substituents in Ar1 and Ar2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.

[0078] In some embodiments of this application, Ar1 and Ar2 may be the same or different, and are independently selected from substituted or unsubstituted groups W, wherein the unsubstituted group W is selected from the group consisting of:

[0079]

[0080] The substituted group W has one or more substituents, which are independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl. When the number of substituents on the group W is greater than 1, the substituents may be the same or different.

[0081] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0082]

[0083]

[0084] Alternatively, Ar1 and Ar2 may be the same or different, and each may be independently selected from the group consisting of:

[0085]

[0086] In some embodiments of this application, Each is independently selected from the group consisting of the following groups:

[0087]

[0088]

[0089] Specifically, Each is independently selected from the group consisting of the following groups:

[0090]

[0091]

[0092] Further optional, At least one of the following groups is selected from the group consisting of:

[0093]

[0094]

[0095] In some specific embodiments of this application, organic compounds At least one of the groups is a phenyl group that links a dibenzo five-membered ring. When organic compounds containing such groups are used in the organic light-emitting layer of organic electroluminescent devices, the organic electroluminescent devices will have a longer lifespan.

[0096] In some specific embodiments of this application, organic compounds At least one of them is selected from the group consisting of:

[0097]

[0098] Using organic compounds containing the above-mentioned groups in the organic light-emitting layer of organic electroluminescent devices will result in higher efficiency for the organic electroluminescent devices.

[0099] In some embodiments of this application, the organic compound is selected from the group consisting of:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] 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.

[0109] In some embodiments of this application, the organic electroluminescent device is a red organic electroluminescent device. For example... Figure 1 As shown, an organic electroluminescent device may include an anode 100, a first hole transport layer 320, a second hole transport layer 330, an organic light-emitting layer 340, an electron transport layer 350, an electron injection layer 360, and a cathode 200, which are stacked sequentially.

[0110] 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.

[0111] 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 is HT-23, and the second hole transport layer is HT-24.

[0112]

[0113]

[0114] Optionally, a hole injection layer 310 may be provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 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;

[0115]

[0116] In some embodiments of this application, the hole injection layer 310 is composed of PD and HT-23.

[0117] 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.

[0118] 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.

[0119] In one embodiment of this application, the organic light-emitting layer 340 comprises the organic material of this application.

[0120] Optionally, the organic material of this application is used as the host material in the organic light-emitting layer, and further, it is used as a hole-type host material.

[0121] In some embodiments of this application, the electron host material in the organic light-emitting layer is

[0122] The guest material of the organic light-emitting layer 340 can be a compound with a condensed aryl ring or its derivatives, a compound with a heteroaryl ring or its derivatives, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also referred to as a dopant or dopant. Specific examples of red phosphorescent dopants used in red organic electroluminescent devices include, but are not limited to, […].

[0123]

[0124] In a more specific embodiment, the host material in the organic light-emitting layer is the organic compound of this application and RH-N, and the guest material is RD.

[0125] The electron transport layer 350 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, ET-1, 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:

[0126]

[0127]

[0128] In some specific embodiments of this application, the electron transport layer 350 is composed of ET-1 and LiQ.

[0129] 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.

[0130] In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

[0131] A third aspect of this application provides an electronic device including the electronic components described in the second aspect of this application.

[0132] 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.

[0133] The following examples illustrate the synthesis method of the organic compounds of this application, but this application is not limited thereto.

[0134] Compounds synthesized using methods not mentioned in this application are all raw material products obtained through commercial means.

[0135] This application does not specifically limit the synthesis method of the provided organic materials. Those skilled in the art can determine a suitable synthesis method based on the organic materials and the preparation methods provided in the preparation examples section of this application. Those skilled in the art can obtain all the organic materials provided in this application based on these exemplary preparation methods. All specific preparation methods for these organic materials will not be detailed here, and should not be construed as limitations on this application.

[0136] Preparation of compounds

[0137] Synthesis of Sub-a1:

[0138]

[0139] Under nitrogen protection, 9-bromo-7H-benzo[C]carbazole (14.80 g, 50 mmol), 2-iododibenzothiophene (18.61 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 (250 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 gray-green solid (16.26 g; yield 68%).

[0140] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a3 were synthesized by replacing 2-iododibenzothiophene with reactant A shown in Table 1.

[0141] Table 1: Synthesis of Sub-a2 to Sub-a3

[0142]

[0143]

[0144] Synthesis of Sub-b1:

[0145]

[0146] Under nitrogen protection, 10-bromo-7-phenyl-7H-benzo[C]carbazole (18.61 g, 50 mmol), 1-chloro-2-naphthylamine (8.88 g, 50 mmol), tris(dibenzylacetone)palladium (0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol), and xylene (250 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, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid Sub-b1 (12.20 g; yield 52%).

[0147] Sub-b2 to Sub-b9 were synthesized by replacing 10-bromo-7-phenyl-7H-benzo[C]carbazole with reactant B shown in Table 2, as in Sub-c1.

[0148] Table 2: Synthesis of Sub-b2 to Sub-b9

[0149]

[0150]

[0151] Synthesis of Sub-c1:

[0152]

[0153] Under nitrogen protection, Sub-b1 (23.44 g, 50 mmol), palladium acetate (0.56 g, 2.5 mmol), tricyclohexylphosphine tetrafluoroborate (CAS: 58656-04-5, 1.84 g, 5 mmol), cesium carbonate (32.58 g, 100 mmol), and N,N-dimethylacetamide (260 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid Sub-c1 (10.38 g; yield 48%).

[0154] Sub-c2 to Sub-c9 were synthesized by replacing Sub-b1 with reactant C shown in Table 3, referring to Sub-c1.

[0155] Table 3: Synthesis of Sub-c2 to Sub-c9

[0156]

[0157]

[0158] Synthesis of Sub-c10:

[0159]

[0160] Under nitrogen protection, Sub-c1 (10.81 g, 25 mmol) and 200 mL of benzene-D6 were added to a 100 mL three-necked flask. The mixture was heated to 60 °C, and then trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The mixture was then heated to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, and the mixture was stirred for 10 minutes. A saturated aqueous solution of K3PO4 was then added to neutralize the reaction mixture. The organic layer was extracted with dichloromethane (50 mL × 3 times), and the combined organic phases were 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, Sub-c10 (7.92 g, yield 71%).

[0161] Synthesis of compound 5:

[0162]

[0163] Under nitrogen protection, Sub-Cl (10.81 g, 25 mmol), 2-bromophenanthrene (7.71 g, 30 mmol), tris(dibenzylacetone)dipalladium (0.46 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.41 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid (12.32 g; yield 81%, m / z = 609.2 [M+H)). + ).

[0164] Referring to the synthesis of compound 5, using reactant D as shown in Table 4 instead of Sub-c1 and reactant E instead of 2-bromophenanthroline, the following compounds of this application were synthesized.

[0165] Table 4: Synthesis of the compounds in this application

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] NMR data for some compounds are shown in Table 5 below.

[0173] Table 5

[0174]

[0175] Fabrication and evaluation of organic electroluminescent devices:

[0176] This application also provides an organic electroluminescent device, including an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes the aforementioned organic compound of this application. The organic electroluminescent device of this application will be described in detail below through embodiments. However, the following embodiments are merely examples of this application and are not intended to limit the scope of this application.

[0177] Example 1: Red Organic Electroluminescent Device

[0178] 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. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0179] On the experimental substrate (anode), PD and compound HT-23 were co-deposited at a deposition rate of 2%:98% to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed, and then compound HT-23 is vacuum-deposited onto the hole injection layer to form a layer with a thickness of [thickness missing]. The hole transport layer.

[0180] The compound HT-24 was vacuum-deposited on the first hole transport layer to form a thickness of [missing information]. The second hole transport layer.

[0181] Next, on the second hole transport layer, compound 5:RH-N:RD was co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light-emitting layer (EML)

[0182] On the light-emitting layer, compound ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio 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-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0183] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP-1 was used to complete the fabrication of a red organic electroluminescent device.

[0184] Examples 2-23

[0185] Except that, when fabricating the light-emitting layer, compound X from Table 6 is used instead of compound 5 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0186] Comparative Examples 1-3

[0187] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound 5 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0188] The performance of the red organic electroluminescent devices prepared in Examples 1-23 and Comparative Examples 1-3 was tested. Specifically, the IVL performance of the devices was tested under a condition of 10 mA / cm², and the T95 device lifetime was 20 mA / cm². 2 The test was conducted under the specified conditions, and the test results are shown in Table 6.

[0189] The compounds used in the preparation of the various examples and comparative examples have the following structures:

[0190] Table 6

[0191]

[0192]

[0193] Referring to Table 6 above, compared with Comparative Examples 1 to 3, using the organic compound of this application as the host material of the light-emitting layer (hole transport material in the hybrid red light host material) improves the current efficiency by at least 11.1% and the lifetime by at least 11.4%.

[0194] Other embodiments of this application will readily occur to those skilled in the art upon consideration of the specification and practice of the invention disclosed herein. This application is intended to cover any variations, uses, or adaptations of this application that follow the general principles of this application and include common knowledge or customary techniques in the art not disclosed herein. The specification and examples are to be considered exemplary only, and the true scope and spirit of this application are indicated by the following claims.

[0195] It should be understood that this application is not limited to the precise structure described above and shown in the accompanying drawings, and various modifications and changes can be made without departing from its scope. The scope of this application is limited only by the appended claims.

Claims

1. An organic compound characterized in that, The organic compound has a structure as shown in Formula 1: L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group; the substituents in L1and L2are the same or different, and each is independently selected from deuterium, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-butyl group, or a phenyl group; Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted spirobifluorenyl group; the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a t-butyl group, or a phenyl group; R1, R2, or R3is the same, and is selected from deuterium; n1represents the number of substituents R1, and n1is selected from 0, 1, 2, 3, 4, 5, or 6; n2represents the number of substituents R2, and n2is selected from 0, 1, or 2; n3represents the number of substituents R3, and n3is selected from 0, 1, 2, 3, 4, 5, or 6; and the organic compound is not 2. The organic compound according to claim 1, characterized by each independently selected from the group consisting of:

3. An organic compound characterized in that, the organic compound is selected from the group consisting of:

4. An organic electroluminescent device, characterized by comprising The organic electroluminescence device comprises an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1-3.

5. The organic electroluminescent device according to claim 4, characterized in that The functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound.

6. The organic electroluminescent device according to claim 4, wherein The organic electroluminescence device is a red organic electroluminescence device.

7. An electronic device, comprising: The organic electroluminescence device comprises an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound according to any one of claims 1-3.

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