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 and an electronic device. The organic compound has a structure as shown in formula 1. When the organic compound is used in an organic electroluminescent device, the performance of the organic electroluminescent device can be significantly improved.

Description

Technical Field

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

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

[0003] Existing technologies disclose host materials for fabricating organic light-emitting layers in organic electroluminescent devices. However, it remains necessary to continue developing novel materials to further improve the performance of organic electroluminescent devices. 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. The organic compound can improve the performance of the organic electroluminescent device and electronic device, for example, by reducing the driving voltage of the device and improving the device efficiency and lifespan.

[0005] In a first aspect, this application provides an organic compound having the structure shown in Formula 1:

[0006]

[0007] Among them, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0008] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0009] R1 is a deuterated aryl group with 6 to 12 carbon atoms;

[0010] The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms.

[0011] 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.

[0012] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0013] The core structure of the organic compound in this application is composed of an aryl-substituted triazine group and indolo[2,3-A]carbazole, with a deuterated aryl group attached to a specific site on the indolo[2,3-A]carbazole. This attachment of the deuterated aryl group to the specific site on the indolo[2,3-A]carbazole enhances steric hindrance and reduces material crystallinity, thereby improving device lifetime. In this compound, the triazine group is directly bonded to the nitrogen atom of the indolo[2,3-A]carbazole, resulting in a higher first triplet energy level. The compound exhibits high electron mobility and a high first triplet energy level, along with high energy transfer efficiency, making it suitable as a host material (especially an electronic host material) in organic electroluminescent devices. Organic electroluminescent devices using this material as the host material can significantly improve device performance.

[0014] Other features and advantages of this application will be described in detail in the following detailed description section. Attached Figure Description

[0015] 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.

[0016] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to this application.

[0017] Figure 2 This is a schematic diagram of the structure of an electronic device according to this application.

[0018] Figure Labels

[0019] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0020] 320, Hole transport layer; 330, Hole adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

[0021] 360°, electron injection layer 400°, electronic device Detailed Implementation

[0022] 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.

[0023] A first aspect of this application provides an organic compound having the structure shown in Formula 1:

[0024]

[0025] Among them, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0026] Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0027] R1 is a deuterated aryl group with 6 to 12 carbon atoms;

[0028] The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms.

[0029] 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.

[0030] 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 groups, alkyl, haloalkyl, deuterylalkyl, aryl, deuterylaryl, haloaryl, cycloalkyl, etc. The number of substituents can be one or more.

[0031] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0032] 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.

[0033] 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.

[0034] In this application, terphenyl includes

[0035] 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.

[0036] 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 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.

[0037] In this application, aryl groups used as substituents for L1, L2, L3, Ar1, Ar2, and Ar3 include, but are not limited to, phenyl, naphthyl, etc.

[0038] 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.

[0039] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0040] In this application, deuterated aryl refers to an aryl group containing at least one deuterated substituent. Specific embodiments of deuterated aryl include, but are not limited to, pentadeuterated phenyl and pentadeuterated biphenyl.

[0041] 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.

[0042] 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.

[0043]

[0044] 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.

[0045]

[0046] In some embodiments of this application, L1, L2, and L3 may be the same or different, and are each independently selected from single bonds and substituted or unsubstituted aryl groups with 6 to 12 carbon atoms.

[0047] Optionally, the substituents in L1, L2 and L3 may be the same or different, and may be independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.

[0048] In other embodiments of this application, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0049] Optionally, the substituents in L1, L2 and L3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0050] Further optionally, L1, L2, and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene.

[0051] In some embodiments of this application, L1, L2, and L3 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of:

[0052]

[0053] Specifically, L1, L2, and L3 may be the same or different, and are each independently selected from the group consisting of single bonds or groups consisting of the following:

[0054]

[0055]

[0056] In some embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0057] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups having 1 to 5 carbon atoms, phenyl groups or pentadeuterated phenyl groups.

[0058] In other embodiments of this application, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted terphenyl.

[0059] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl or pentadeuterated phenyl.

[0060] Further optionally, Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl.

[0061] In some embodiments of this application, Ar1 and Ar2 are each independently selected from the group consisting of:

[0062]

[0063] Specifically, the substituents in Ar1 and Ar2 may be the same or different, and are independently selected from the group consisting of the following groups:

[0064]

[0065] In some embodiments of this application, Ar3 is selected from the group consisting of:

[0066]

[0067] Specifically, Ar3 is selected from the group consisting of the following groups:

[0068]

[0069] In some embodiments of this application, and Whether identical or different, each is independently selected from the group consisting of the following groups:

[0070]

[0071] Specifically, and Whether identical or different, each is independently selected from the group consisting of the following groups:

[0072]

[0073] Some implementations of this application are placed in the middle. Selected from the group consisting of the following groups:

[0074]

[0075] Specifically, Selected from the group consisting of the following groups:

[0076]

[0077] In some embodiments of this application, in formula 1 Selected from groups consisting of the following structures:

[0078]

[0079]

[0080] In some embodiments of this application, R1 is selected from... In some preferred embodiments of this application, R1 is Specifically, R1 is selected from the group consisting of the following groups:

[0081]

[0082] In some embodiments of this application, the organic compound is selected from the group consisting of:

[0083]

[0084]

[0085]

[0086]

[0087]

[0088] In a second aspect, this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the organic compound described in the first aspect of this application.

[0089] The organic compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0090] Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic compound. The organic light-emitting layer may be composed of the organic compound provided in this application, or it may be composed of the organic compound provided in this application and other materials.

[0091] Optionally, the functional layer further includes a hole transport layer located between the anode and the organic light-emitting layer.

[0092] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, an organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, a hole adjustment layer (also known as a hole auxiliary layer or 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.

[0093] Optionally, the anode 100 comprises an anode material, preferably one with a high work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0094] In this application, the hole transport layer may include one or more hole transport materials. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0095]

[0096]

[0097] In one embodiment, the hole transport layer 320 may be composed of HT-25.

[0098] Optionally, the hole adjustment layer 330 may include one or more hole transport materials, which may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds. This application does not impose any specific limitations on these materials. For example, in some embodiments of this application, the hole adjustment layer 330 is composed of HT-26.

[0099] 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 321. 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;

[0100]

[0101]

[0102] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-25.

[0103] Optionally, the organic light-emitting layer 340 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 340 is composed of a host material and a guest material. Holes injected into the organic light-emitting layer 330 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 guest material, thereby enabling the guest material to emit light.

[0104] The host material of the organic light-emitting layer 340 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. Optionally, the host material comprises the organic compounds of this application.

[0105] The guest material of the organic light-emitting layer 340 can be a compound or its derivative having a condensed aryl ring, a compound or its derivative having a heteroaryl ring, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. For example, specific examples of phosphorescent dopant include, but are not limited to,

[0106]

[0107] In some embodiments of this application, the compounds of this application are used as electronic host materials for organic electroluminescent layers.

[0108] In one embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 340 comprises the organic compound of this application and GH-P, and the guest material is GD-01.

[0109] 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-2, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials. This application does not impose any specific limitations on these materials. The material of the electron transport layer 350 includes, but is not limited to, the following compounds:

[0110]

[0111] In one embodiment of this application, the electron transport layer 350 may be composed of ET-2 and LiQ.

[0112] 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.

[0113] Optionally, an electron injection layer 350 may be disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 may include ytterbium (Yb).

[0114] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0115] 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.

[0116] The following examples illustrate the synthesis method of the organic compounds of this application, but this disclosure is not limited thereto.

[0117] Synthesis Examples

[0118] 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.

[0119] Synthesis of intermediate IM-a:

[0120]

[0121] 2,3-Dichloronitrobenzene (15.0 g; 78.1 mmol), carbazole 2-borate (16.5 g; 78.1 mmol), tetrakis(triphenylphosphine)palladium (1.8 g; 1.6 mmol), potassium carbonate (21.6 g; 156.3 mmol), tetrabutylammonium bromide (5.0 g; 15.6 mmol), toluene (120 mL), ethanol (30 mL), and deionized water (30 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 75–80 °C and stirred for 48 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to give a white solid intermediate IM-a (14.9 g; yield: 59%).

[0122] Synthesis of intermediate b1:

[0123]

[0124] Intermediate IM-a (12.1 g; 37.5 mmol), bromobenzene (7.1 g; 45.0 mmol), tris(dibenzylacetone)palladium (0.3 g; 0.4 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.4 g; 0.7 mmol), sodium tert-butoxide (5.4 g; 56.2 mmol), and xylene (120 mL) were added to a round-bottom flask and reacted under nitrogen protection at 135 °C–140 °C for 24 hours with stirring. After cooling to room temperature, the reaction mixture was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as eluent to give a white solid intermediate b1 (11.2 g; yield: 75%).

[0125] Following the synthetic method for intermediate b1, using reactant A from Table 1 to replace bromobenzene, the intermediates shown in Table 1 were synthesized:

[0126] Table 1

[0127]

[0128]

[0129] Synthesis of intermediate c1:

[0130]

[0131] Intermediate b1 (10.0 g; 25.1 mmol), triphenylphosphine (16.4 g; 62.3 mmol), and o-dichlorobenzene (100 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 175 °C–180 °C with stirring and reacted for 16 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under high temperature and reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane system to give a white solid intermediate c1 (7.0 g; yield 76%).

[0132] Following the synthetic method of intermediate c1, reactant B in Table 2 was used to replace intermediate b1 to synthesize the intermediates shown in Table 2 below:

[0133] Table 2

[0134]

[0135]

[0136]

[0137] Synthesis of intermediate d1:

[0138]

[0139] Intermediate C1 (7.8 g; 21.3 mmol), D5-phenylboronic acid pinacol ester (4.7 g; 22.3 mmol), palladium acetate (0.1 g; 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.2 g; 0.4 mmol), cesium carbonate (10.4 g; 31.9 mmol), toluene (60 mL), ethanol (15 mL), and deionized water (15 mL) were added to a round-bottom flask under nitrogen protection. The mixture was heated to 75-80 °C and stirred for 8 hours. The reaction mixture was cooled to room temperature, deionized water was added, and the mixture was separated. The organic phase was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using a dichloromethane / n-heptane solvent system to obtain a white solid intermediate D1 (6.9 g; 78%).

[0140] Following the synthetic method of intermediate d1, reactant C in Table 3 was used to replace intermediate c1, and reactant D was used to replace pinacol ester D5-phenylboronic acid, to synthesize the intermediates shown in Table 3 below:

[0141] Table 3

[0142]

[0143]

[0144]

[0145] Synthesis of Compound 1:

[0146]

[0147] Intermediate d1 (5.0 g; 12.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g; 18.3 mmol), and N,N-dimethylformamide (50 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred and cooled to -5°C to 0°C. Sodium hydride (0.3 g; 14.5 mmol) was added, and the mixture was stirred at -5°C to 0°C for 1 hour. The reaction mixture was then heated to 20°C to 25°C and reacted for 16 hours. The reaction was stopped, and the reaction mixture was washed with water and separated. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using toluene / n-heptane as the eluent, and then purified by recrystallization using a toluene / n-heptane solvent system to obtain a white solid compound 1 (5.1 g; yield: 65%).

[0148] Following the synthetic method of compound 1, reactant E was substituted for intermediate d1, and reactant F was substituted for 2-chloro-4,6-diphenyl-1,3,5-triazine, as shown in Table 4 below, to synthesize the compounds shown in Table 4 below:

[0149] Table 4

[0150]

[0151]

[0152]

[0153]

[0154] Mass spectrometry data of some compounds are shown in Table 5 below.

[0155] Table 5

[0156]

[0157]

[0158] NMR data for some compounds are shown in Table 6 below.

[0159] Table 6

[0160]

[0161] Fabrication of organic electroluminescent devices

[0162] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0163] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Organic solvents are used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0164] Compound HT-25 and PD were co-deposited on the experimental substrate at a deposition ratio of 98%:2%, forming a thickness of [missing information]. A hole injection layer (HIL) is formed, and then compound HT-25 is vacuum-deposited onto the hole injection layer to form a thickness of [thickness missing]. The hole transport layer.

[0165] Compound HT-26 was vacuum-deposited onto the hole transport layer to form a thickness of [missing information]. Hole adjustment layer.

[0166] On the hole adjustment layer, compound 1:GH-P:GD-01 was co-deposited at a deposition rate of 40%:50%:10% to form a layer with a thickness of [missing information]. The organic light-emitting layer (green light-emitting layer).

[0167] On the organic light-emitting layer, compounds ET-2 and LiQ were 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.

[0168] Furthermore, CP-1 is vacuum-deposited onto the aforementioned cathode to form a thickness of [missing information]. The organic coating layer completes the fabrication of green organic electroluminescent devices.

[0169] Examples 2-31

[0170] Organic electroluminescent devices were prepared using the same method as in Example 1, except that the compounds listed in Table 7 below (collectively referred to as "Compound X") were used instead of Compound 1 in Example 1 when fabricating the light-emitting layer.

[0171] Comparative Examples 1-3

[0172] Except that, when fabricating the light-emitting layer, compounds A, B, and C were used instead of compound 1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0173]

[0174] The performance of the green organic electroluminescent devices prepared in Examples 1-31 and Comparative Examples 1-3 was tested, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.

[0175] Table 7

[0176]

[0177]

[0178] Referring to Table 7 above, when the compounds of this application are used as the host material of organic electroluminescent devices, the current efficiency of the devices is increased by at least 13% and the lifetime is increased by at least 11.8% compared with Comparative Examples 1 to 3.

[0179] When the compounds of this application are used as the host material for organic electroluminescent devices, compared with compound A, the driving voltage of the device is significantly reduced, and the luminous efficiency and lifetime are significantly improved. The reason for this may be that the triazine group in the compounds of this application adopts an aryl-type substituent, which, compared with the dibenzofuran-1-yl in compound A, gives the compounds of this application a higher first triplet energy level and a higher electron mobility.

[0180] When the compound of this application is used as the host material for organic electroluminescent devices, the luminous efficiency and lifetime of the device are significantly improved compared to compound B. The reason for this may be that the triazine group in the compound of this application is directly connected to the N atom of indolo[2,3-A]carbazole, thereby possessing a higher first triplet energy level.

[0181] When the compound of this application is used as the host material for organic electroluminescent devices, it significantly improves the device lifetime compared to compound C. The reason for this may be that the indolo[2,3-A]carbazole in the compound of this application is linked to a deuterated aryl group at a specific site, which increases the steric hindrance of the compound, thereby reducing the crystallinity of the material and improving its amorphous stability.

[0182] The embodiments of this application have been described in detail above with reference to the accompanying drawings. However, this application is not limited to the specific details of the above embodiments. Within the scope of the technical concept of this application, various simple modifications can be made to the technical solution of this application, and these simple modifications all fall within the protection scope of this application.

Claims

1. An organic compound, characterized in that, This organic compound has the structure shown in Formula 1: Among them, L1, L2 and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; R1 is selected from The substituents in L1, L2, L3, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, haloalkyl groups with 1 to 10 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, aryl groups with 6 to 20 carbon atoms, deuterated aryl groups with 6 to 20 carbon atoms, and haloaryl groups with 6 to 20 carbon atoms.

2. The organic compound according to claim 1, characterized in that, L1, L2, and L3 may be the same or different, and are independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene. The substituents in L1, L2, and L3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterated phenyl.

3. The organic compound according to claim 1, characterized in that, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted aryl groups with 6 to 20 carbon atoms; The substituents in Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, phenyl groups, or pentadeuterated phenyl groups.

4. The organic compound according to claim 1, characterized in that, Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted triphenyl. The substituents in Ar1, Ar2, and Ar3 may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, or pentadeuterated phenyl.

5. The organic compound according to claim 1, characterized in that, Whether identical or different, each is independently selected from the group consisting of the following groups:

6. The organic compound according to claim 5, characterized in that, Whether identical or different, each is independently selected from the group consisting of the following groups:

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

8. The organic compound according to claim 7, characterized in that, Selected from the group consisting of the following groups:

9. The organic compound according to claim 1, characterized in that, In Equation 1 Selected from groups consisting of the following structures:

10. The organic compound according to claim 1, characterized in that, R1 is selected from the group consisting of the following groups:

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

12. 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 11.

13. The organic electroluminescent device according to claim 12, characterized in that, The functional layer includes an organic light-emitting layer, which contains an organic compound as described in any one of claims 1 to 11.

14. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 12 or 13.

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