Organic material, organic electroluminescent device, and electronic device

Abstract

The application belongs to the technical field of organic electroluminescence, and relates to an organic material, an organic electroluminescent device and an electronic device. The organic material has a structure as shown in formula 1. When the organic material 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 particularly to an organic material, an organic electroluminescent device comprising the same, and an electronic device thereof. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence 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, a light-emitting modulation 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] The main problems with existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. As displays become larger, the driving voltage also increases. The organic light-emitting layer material has the most significant impact on lifespan and efficiency in OLEDs; therefore, continuous improvement of the organic light-emitting layer material is necessary to enhance luminous efficiency and lifespan.

[0004] Therefore, it is necessary to continue developing new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] In view of the above-mentioned problems in the prior art, the purpose of this application is to provide an organic material, an organic electroluminescent device containing the organic material, and an electronic device, wherein the use of the organic material in the organic electroluminescent device can improve the performance of the device.

[0006] A first aspect of this application provides an organic material having a structure as shown in Formula 1:

[0007]

[0008] Where X is selected from C(R1R2), N(R3), O or S;

[0009] R1, R2, and R3 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, or deuterated aryl groups having 6 to 30 carbon atoms.

[0010] L is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0011] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0012] D represents deuterium;

[0013] b, b, c, m, and n are the number of D; a and c are the same or different, and are independently selected from 0, 1, 2, and 3 respectively; b is selected from 0, 1, or 2;

[0014] n is selected from 0, 1, 2, 3, 4 or 5; m is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0015] 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 material disclosed in the first aspect of this application.

[0016] A third aspect of this application provides an electronic device including the organic electroluminescent device disclosed in the second aspect of this application.

[0017] This application provides an organic material composed of a carbazobenzothiophene in a specific fusion configuration and a phenyl-substituted dibenzo5-membered ring at a specific position, wherein the carbazobenzothiophene in the specific fusion configuration and the phenyl-substituted dibenzo5-membered ring at the specific position are connected by an arylene group. The carbazobenzothiophene in the specific fusion configuration exhibits excellent hole transport properties, and the connection between the arylene group and the phenyl-substituted dibenzo5-membered ring at the specific position results in a high T1 energy level for the compound. Therefore, when the compound of this application is used as the host material for organic electroluminescent devices, it can significantly improve the luminous efficiency and lifetime of the device.

[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 2This 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, Hole transport layer; 330, Luminescent adjustment layer; 340, Organic light-emitting layer; 350, Electron transport layer

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

[0026] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0027] A first aspect of this application provides an organic material having a structure as shown in Formula 1:

[0028]

[0029] Where X is selected from C(R1R2), N(R3), O or S;

[0030] R1, R2, and R3 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, or deuterated aryl groups having 6 to 30 carbon atoms.

[0031] L is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms;

[0032] The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms.

[0033] D represents deuterium;

[0034] c, b, c, m, and n are the number of D; a and c are the same or different, and are independently selected from 0, 1, 2, and 3 respectively; b is selected from 0, 1, or 2;

[0035] n is selected from 0, 1, 2, 3, 4 or 5; m is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0036] In this application, D represents deuterium.

[0037] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...independently selected from" 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.

[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, halogen groups, cyano, alkyl, deuterated alkyl, cycloalkyl, aryl, deuterated aryl, etc. The number of substituents can be one or more.

[0039] In this application, a non-positioned linker bond refers to a single bond extending from the ring system. This means that one end of the linking bond can connect to any position in the ring system that the bond passes through, and the other end connects to the rest of the compound molecule.

[0040] 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 linkages that span the bicyclic ring. This means that any possible connection mode is shown in equations (f-1) to (f-10).

[0041]

[0042] 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.

[0043]

[0044] In this application, the number of carbon atoms in L refers to the total number of carbon atoms. For example, if L is selected from 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, "alkyl" can include straight-chain alkyl or branched alkyl. An alkyl group can have 1 to 10 carbon atoms. In this application, numerical ranges such as "1 to 10" refer to integers within a given range; for example, "1 to 10 carbon atoms" means an alkyl group that may contain 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, etc.

[0046] In this application, cycloalkyl refers to a group derived from a saturated cyclic carbon chain structure. A cycloalkyl group may have 3 to 10 carbon atoms; in this application, numerical ranges such as "3 to 10" refer to integers within a given range; for example, "5 to 10 carbon atoms" means that it may contain 5, 6, 7, 8, 9, or 10 carbon atoms. Optionally, specific embodiments of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, norbornyl, etc.

[0047] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group 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, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, triphenylene (also known as benzo[9,10]phenanthryl), perylene, pyrene, benzofluoranthyl, etc. Base, etc.

[0048] In this application, the number of carbon atoms in the substituted or unsubstituted aryl group can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, etc. In this application, biphenyl can be understood as either a phenyl-substituted aryl group or an unsubstituted aryl group.

[0049] In this application, the term "arylene" refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0050] In this application, a substituted aryl group refers to an aryl group in which one or more hydrogen atoms are replaced by other groups. For example, at least one hydrogen atom may be replaced by a deuterium, halogen group, cyano, alkyl, deuterated alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, or deuterated aryl group. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and its substituents. For example, L represents... Therefore, it has 12 carbon atoms.

[0051] In this application, aryl groups used as substituents include, but are not limited to, phenyl and naphthyl groups.

[0052] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0053] In this application, terphenyl includes

[0054] In this application, "deuterated" means that at least one hydrogen ("H") in a compound or group is replaced by deuterium ("D"); specifically, a deuterated compound or deuterated group can be a compound or group in which one, more or all of the available hydrogens have been replaced by deuterium.

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

[0056] In this application, a haloalkyl group can be an alkyl group in which one or more hydrogen atoms are replaced by halogen atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.

[0057] In this application, a deuterated alkyl group can be an alkyl group in which one or more hydrogen atoms are replaced by deuterium. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.

[0058] In this application, the deuterated aryl group can be one or more hydrogen atoms (H) of the aryl group that are replaced by deuterium (D). Specific examples of deuterated aryl groups include, but are not limited to, pentadeuterated phenyl, heptadeuterated naphthyl, and nonadeuterated biphenyl.

[0059] In some embodiments of this application, L is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms. For example, L is selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms.

[0060] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, deuterated phenyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 12 carbon atoms, and deuterated aryl groups with 6 to 12 carbon atoms.

[0061] In some embodiments of this application, L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, and substituted or unsubstituted biphenylene.

[0062] Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl or pentadeuterated phenyl.

[0063] In some embodiments of this application, L is selected from the group consisting of:

[0064]

[0065] Specifically, L is selected from the group consisting of the following groups:

[0066]

[0067] In some embodiments of this application, R1, R2 and R3 may be the same or different, and are independently selected from alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, and deuterated aryl groups having 6 to 12 carbon atoms.

[0068] In some embodiments of this application, R1, R2, and R3 may be the same or different, and are each independently selected from methyl, trideuterated methyl, phenyl, naphthyl, or pentadeuterated phenyl.

[0069] Optionally, R1 and R2 are the same and are selected from methyl, trideuterated methyl, phenyl or pentadeuterated phenyl.

[0070] Alternatively, R3 is selected from phenyl or pentadeuterated phenyl.

[0071] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0072]

[0073] Specifically, in Equation 1 Selected from the group consisting of the following groups:

[0074]

[0075]

[0076] In some embodiments of this application, in formula 1 Selected from the group consisting of the following groups:

[0077]

[0078] 10. Specifically, in Formula 1 Selected from the group consisting of the following groups:

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] Optionally, the organic material is selected from the group consisting of the following compounds:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] 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 material described in the first aspect of this application.

[0098] In one embodiment of this application, the organic electroluminescent device is a fluorescent device.

[0099] In one specific embodiment of this application, the organic electroluminescent device is a green organic electroluminescent device.

[0100] In some embodiments of this application, the organic electroluminescent device sequentially includes an anode (ITO substrate), a hole transport layer, a light-emitting adjustment layer, an organic light-emitting layer, an electron transport layer, an electron injection layer, a cathode (Mg-Ag mixture), and an organic capping layer.

[0101] In one specific embodiment of this application, such as Figure 1 As shown, the organic electroluminescent device of this application includes an anode 100, a cathode 200, and at least one functional layer 300 between the anode layer and the cathode layer. The functional layer 300 includes a hole injection layer 310, a hole transport layer 320, a light emission adjustment layer 330, an organic light emission layer 340, an electron transport layer 350, and an electron injection layer 360.

[0102] 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.

[0103] Optionally, the hole transport layer 320 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 transport layer 320 is composed of the compound HT-1.

[0104] Optionally, the luminescence adjustment layer 330 (also referred to as a hole adjustment layer, electron blocking layer, hole auxiliary layer, hole buffer layer, luminescence auxiliary layer, or second hole transport layer) may include one or more hole transport materials. The hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds; this application does not impose any special limitations on this. For example, in some embodiments of this application, the luminescence adjustment layer 330 is composed of the compound HT-2.

[0105] 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 and electrons injected into the organic light-emitting layer 330 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.

[0106] 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, and this application does not impose any special restrictions on this.

[0107] In some embodiments of this application, the organic material is a TADF (Thermally Activated Delayed Fluorescence) material.

[0108] In some embodiments of this application, the organic electroluminescent device is a green organic electroluminescent device, which includes an organic light-emitting layer, and the organic light-emitting layer includes the organic material of this application, compound GH-1, and guest material GD-01.

[0109] 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 benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any special limitations on them. For example, in some embodiments of this application, the electron transport layer 350 can be composed of compounds ET-1 and LiQ.

[0110] Optionally, the cathode 200 comprises a cathode material having a small work function that 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. Preferably, a metal electrode comprising silver and magnesium is included as the cathode.

[0111] Optionally, an organic coating layer is also provided on the cathode 200.

[0112] 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. In some embodiments of this application, the hole injection layer 310 may be composed of compound PD-1 and compound HT-1.

[0113] Optionally, an electron injection layer 360 may be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In some embodiments of this application, the electron injection layer 360 may include ytterbium (Yb).

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

[0115] For example, such as Figure 2 As shown, the electronic device provided in this application is a first electronic device 400, which includes any of the organic electroluminescent devices described in the above-described embodiments. This electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc. Since the first electronic device 400 has the aforementioned organic electroluminescent device, it has the same beneficial effects, which will not be repeated here.

[0116] The present application will now be described in detail with reference to embodiments. However, the following description is intended to explain the present application and not to limit the scope of the present application in any way.

[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. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0119] Synthesis of intermediate Sub-I-a1

[0120]

[0121] Under nitrogen protection, 1-bromo-8-chlorodibenzofuran (35.0 g, 124.3 mmol), phenylboronic acid (16.7 g, 136.8 mmol), tetra(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (34.4 g, 248.6 mmol), tetrabutylammonium bromide (2.0 g, 6.2 mmol), toluene (280 mL), ethanol (140 mL), and deionized water (70 mL) were added to a round-bottom flask. The reaction 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 give a white solid intermediate, Sub-I-a1 (22.9 g, yield: 66%).

[0122] Following the synthetic method of intermediate Sub-I-a1, reactant a was used to replace 1-bromo-8-chlorodibenzofuran, and reactant b was used to replace phenylboronic acid, to synthesize the intermediates shown in Table 1 below.

[0123] Table 1

[0124]

[0125]

[0126] Synthesis of intermediate Sub-II-a1

[0127]

[0128] Intermediate Sub-I-a1 (20.0 g, 71.8 mmol), pinacol diborate (27.3 g, 107.6 mmol), tris(dibenzylacetone)palladium (0.6 g, 0.7 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.7 g, 1.4 mmol), potassium acetate (14.1 g, 143.5 mmol), and 1,4-dioxane (200 mL) were added to a round-bottom flask under nitrogen protection and reacted at 101 °C for 12 hours with stirring. After cooling to room temperature, dichloromethane and deionized water were added to the reaction solution. The mixture was separated, the organic phase was washed with water and dried over 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 Sub-II-a1 (18.3 g, yield: 69%).

[0129] Following the synthetic method of intermediate Sub-II-a1, reactant b was used to replace intermediate Sub-I-a1 to synthesize the intermediates shown in Table 2 below.

[0130] Table 2

[0131]

[0132]

[0133] Synthesis of intermediate Sub-a1

[0134]

[0135] Under nitrogen protection, Sub-II-a1 (18.0 g, 48.6 mmol), 4-bromochlorobenzene (10.2 g, 53.5 mmol), tetra(triphenylphosphine)palladium (1.1 g, 1.0 mmol), potassium carbonate (13.4 g, 97.2 mmol), tetrabutylammonium bromide (0.8 g, 2.4 mmol), toluene (144 mL), ethanol (72 mL), and deionized water (36 mL) were added to a round-bottom flask. The reaction mixture was heated to 75 °C–80 °C and stirred for 9 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, Sub-a1 (12.4 g, yield: 72%).

[0136] Following the synthesis method of intermediate Sub-a1, reactant d was used to replace intermediate Sub-II-a1, and reactant c was used to replace 4-bromochlorobenzene to synthesize the intermediates shown in Table 3 below.

[0137] Table 3

[0138]

[0139]

[0140]

[0141] Synthesis of compound A1

[0142]

[0143] Under nitrogen protection, Sub 1 (10.0 g, 36.6 mmol), intermediate Sub-a1 (13.6 g, 38.4 mmol), tris(dibenzylacetone)palladium (0.4 g, 0.4 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.3 g, 0.7 mmol), sodium tert-butoxide (7.0 g, 73.2 mmol), and xylene (100 mL) were added to a round-bottom flask. The mixture was stirred and reacted at 135 °C–140 °C for 8 hours. 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, and then purified by recrystallization using a toluene / n-heptane solvent system to obtain a white solid compound A1 (14.1 g, yield: 65%).

[0144] Following the synthetic method of compound A1, reactant d was used to replace Sub 1, and reactant e was used to replace Sub-a1 to synthesize the compounds shown in Table 4 below.

[0145] Table 4

[0146]

[0147]

[0148]

[0149] Mass spectrometry data of some compounds are shown in Table 5 below.

[0150] Table 5

[0151]

[0152]

[0153] The NMR data of some compounds are shown in Table 6 below.

[0154] Table 6

[0155]

[0156] Fabrication of organic electroluminescent devices

[0157] Example 1: Fabrication of Green Organic Electroluminescent Devices

[0158] 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 also used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0159] On the experimental substrate (anode), PD-1:HT-1 were co-deposited at a deposition rate ratio of 2%:98% to form a thickness of [missing information]. Hole injection layer.

[0160] HT-1 was vacuum-deposited onto the hole injection layer to form a layer with a thickness of [missing information]. The hole transport layer.

[0161] Compound HT-2 was vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. The light-emitting adjustment layer.

[0162] On the light-emitting adjustment layer, compounds A1:GH-1:GD-01 were co-deposited in a ratio of 60%:39%:1% to form a layer with a thickness of [missing information]. The organic light-emitting layer.

[0163] On the organic light-emitting layer, compounds ET-1 and LiQ were co-deposited at a 1:1 evaporation rate ratio to form... A thick electron transport layer.

[0164] Yb is deposited onto the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer 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.

[0165] The vacuum evaporation thickness on the aforementioned cathode is The CP-1 was used to complete the fabrication of green organic electroluminescent devices.

[0166] Examples 2-15

[0167] Except that when fabricating the organic light-emitting layer, "Compound X" in Table 7 is used instead of Compound A1 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0168] Comparative Examples 1-3

[0169] Except that, when fabricating the organic light-emitting layer, compounds A, B, and C were used instead of compound A1 in Example 1, respectively, the organic electroluminescent device was prepared using the same method as in Example 1.

[0170]

[0171]

[0172] The performance of the green organic electroluminescent devices prepared in Examples 1-15 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 10 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 7.

[0173] Table 7

[0174]

[0175] As shown in Table 7 above, compared with Comparative Examples 1-3, the organic materials of this application can significantly improve the performance of organic electroluminescent devices. Specifically, compared with Comparative Examples 1-3, the current efficiency of the devices in Examples 1-15 is improved by at least 13.6%, and the lifetime is improved by at least 20.7%.

[0176] 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. Organic material, characterized in that, The material has the structure shown in Formula 1: Where X is selected from C(R1R2), N(R3), O or S; R1, R2, and R3 may be the same or different, and are independently selected from alkyl groups having 1 to 10 carbon atoms, deuterated alkyl groups having 1 to 10 carbon atoms, aryl groups having 6 to 30 carbon atoms, or deuterated aryl groups having 6 to 30 carbon atoms. L is selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms; The substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano, alkyl with 1 to 10 carbon atoms, deuterated alkyl with 1 to 10 carbon atoms, cycloalkyl with 3 to 10 carbon atoms, aryl with 6 to 20 carbon atoms, or deuterated aryl with 6 to 20 carbon atoms. D represents deuterium; a, b, c, m, and n are the number of D; a and c are the same or different, and are independently selected from 0, 1, 2, and 3 respectively; b is selected from 0, 1, or 2; n is selected from 0, 1, 2, 3, 4 or 5; m is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

2. The organic material according to claim 1, characterized in that L is selected from substituted or unsubstituted aryl groups having 6 to 12 carbon atoms; Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 5 carbon atoms, deuterated phenyl groups with 1 to 5 carbon atoms, aryl groups with 6 to 12 carbon atoms, and deuterated aryl groups with 6 to 12 carbon atoms.

3. The organic material according to claim 1, characterized in that L is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene; Optionally, the substituents in L may be the same or different, and are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trideuterated methyl, phenyl, naphthyl or pentadeuterated phenyl.

4. The organic material according to claim 1, characterized in that, L is selected from the group consisting of the following groups:

5. The organic material according to claim 1, characterized in that, L is selected from the group consisting of the following groups:

6. The organic material according to claim 1, characterized in that, R1, R2, and R3 may be the same or different, and are independently selected from alkyl groups having 1 to 5 carbon atoms, deuterated alkyl groups having 1 to 5 carbon atoms, aryl groups having 6 to 12 carbon atoms, or deuterated aryl groups having 6 to 12 carbon atoms.

7. The organic material according to claim 1, characterized in that, R1, R2, and R3 may be the same or different, and are each independently selected from methyl, trideuterated methyl, phenyl, naphthyl, or pentadeuterated phenyl.

8. The organic material according to claim 1, characterized in that, In Equation 1 Selected from the group consisting of the following groups:

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

10. The organic material according to claim 1, characterized in that, In Equation 1 Selected from the group consisting of the following groups:

11. The organic material according to claim 1, characterized in that, In Equation 1 Selected from the group consisting of the following groups:

12. The organic material according to claim 1, characterized in that, The organic material is selected from the group consisting of the following compounds:

13. 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 material described in any one of claims 1 to 12; Optionally, the functional layer includes an organic light-emitting layer, which comprises the organic material according to any one of claims 1 to 12; Optionally, the functional layer further includes a hole injection layer, a hole transport layer, a light emission adjustment layer, an electron transport layer, and an electron injection layer; Optionally, the organic electroluminescent device is a green organic electroluminescent device.

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

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