An organic compound and its application

Abstract

This invention relates to an organic compound, belonging to the field of organic light-emitting materials technology, and also to the application of this compound and organic electroluminescent devices containing it. The organic compound of this invention has the structure shown in the following formula. When the compound of this invention is applied in organic electroluminescent devices, especially as a light-emitting layer material, it can ensure that the device achieves excellent results with high luminous efficiency and low start-up voltage.

Description

Technical Field

[0001] This invention relates to an organic compound, belonging to the field of organic light-emitting materials technology, and also to the application of this compound and organic electroluminescent devices containing it. Background Technology

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them ideal for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and stylish optoelectronic products, offering unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. OLEDs, in particular, have developed rapidly and have already achieved commercial success in the information display field. OLEDs can provide highly saturated red, green, and blue colors, and full-color displays made with them do not require an additional backlight, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] Various organic materials have been developed and combined with unique device structures to improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency, and delay device decay. For quantum mechanical reasons, common fluorescent emitters primarily utilize singlet excitons generated when electrons and empty blood combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously utilize triplet and singlet excitons for light emission, and are called phosphorescent emitters, with energy conversion efficiencies up to four times higher than traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the transition from triplet to singlet excitons, achieving high luminescence efficiency without the use of metal complexes, while still effectively utilizing triplet excitons.

[0005] Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the luminescent material through energy transfer, which can also achieve high luminescence efficiency.

[0006] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. Current OLED materials and device structures cannot fully solve the problems related to efficiency, lifespan, and cost of OLED products. Therefore, there is an urgent need in the field to develop an organic electroluminescent material that can improve device luminous efficiency, reduce driving voltage, and extend lifespan. Through careful consideration and continuous experimentation, the researchers of this invention have discovered an ingenious molecular design scheme, which is described in detail below. The compound disclosed in this invention is highly suitable for application in OLEDs and for improving device performance. Summary of the Invention

[0007] One of the objectives of this invention is to provide a compound, particularly an organic electroluminescent material, and especially an electron blocking layer material, wherein the compound, when applied to an organic electroluminescent device, can improve the device's luminous efficiency and reduce the driving voltage.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] This invention provides a compound having the structure shown in formula (1):

[0010]

[0011] In formula (1):

[0012] R 1 Each is independently selected from one of the following: substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino, and adjacent R 1 They can be connected to form a loop or not connected to form a loop;

[0013] Ar 1 and Ar 2 Each is independently selected from one of substituted or unsubstituted C6-C60 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups;

[0014] n is an integer from 0 to 2, m is an integer from 2 to 4, and the sum of m and n is an integer from 2 to 4;

[0015] D 1 For groups represented as in formula (D):

[0016]

[0017] In formula (D): The position of the bond that the group is attached to;

[0018] Ring B and ring C are each independently substituted or unsubstituted C6 to C60 aromatic rings;

[0019] p and q are each independent integers from 0 to 2, and p and q are not both 0 at the same time;

[0020] When ring B and ring C contain substituents, the substituents are independently selected from halogens, cyano groups, nitro groups, hydroxyl groups, amino groups, substituted or unsubstituted C1-C20 chain alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 silyl groups, substituted or unsubstituted C6-C60 arylamino groups, substituted or unsubstituted C3-C60 heteroarylamino groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroarylamino groups. The substitution of each of the above-mentioned substituted or unsubstituted groups is by a group selected from "halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C3-C60 heteroaryl" or a combination of at least two of the above groups, wherein the substituted group is independently connected to the connected aromatic ring or heteroaryl ring to form a ring or not connected to form a ring;

[0021] R 2 and R 3 Representing single substituents to the maximum permissible substituents, R 2 and R 3 Each is independently selected from one of the following: hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.

[0022] When the above R 2 and R 3 When substituents are present, the substituents are selected from one or a combination of at least two of the following: halogens, C1-C20 chain alkyl groups, C3-C20 cycloalkyl groups, C1-C20 alkoxy groups, C1-C20 silyl groups, cyano groups, nitro groups, hydroxyl groups, amino groups, C6-C30 arylamino groups, C3-C30 heteroarylamino groups, C6-C60 aryl groups, and C3-C60 heteroaryl groups.

[0023] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0024] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0025] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0026] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0027] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0028] The heteroatoms in the heteroaryl group of this invention generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0029] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0030] In this invention, the substituted or unsubstituted C6-C30 aryl groups include monocyclic aryl groups and fused-ring aryl groups, with C6-C20 aryl groups being more preferred. A monocyclic aryl group refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily such as phenyl, biphenyl, and terphenyl. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl group refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0031] In this invention, the substituted or unsubstituted C3-C30 heteroaryl groups include monocyclic heteroaryl groups and fused-ring heteroaryl groups, more preferably C4-C20 heteroaryl groups, and more preferably C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridyl. A fused-ring heteroaryl group refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share a group consisting of two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0032] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferably substituted or unsubstituted C1-C16 chain alkyl groups, and more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Substituted or unsubstituted C3-C30 cycloalkyl groups are preferably substituted or unsubstituted C3-C20 cycloalkyl groups, and more preferably substituted or unsubstituted C3-C10 cycloalkyl groups, such as: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, tert-pentyl, cyclohexyl, adamantyl, etc.

[0033] Furthermore, the compounds of the present invention have structures as shown in formula (1-1) or formula (1-2):

[0034]

[0035] In equations (1-1) and (1-2), R 1 Ar 1 Ar 2 m, n, D 1 The definitions are the same as those in equation (1).

[0036] Preferably, the organic compounds of the present invention have the structure shown in formula (1-1).

[0037] More preferably, in equations (1), (1-1), and (1-2), m is 2.

[0038] More preferably, in equations (1), (1-1), and (1-2), n is 0.

[0039] More preferably, in equations (1), (1-1), and (1-2), m is 2 and n is 0.

[0040] Furthermore, the compounds of the present invention have a structure as shown in any of formulas (2) to (10):

[0041]

[0042] In equations (2) to (10), Ar 1 Ar 2 D 1 The definitions are the same as those in equation (1), D 1’ Definition and D 1 Same, D 1 With D 1’ The structures chosen by each may be the same or different.

[0043] Preferably, the organic compound of the present invention has a structure as shown in any of formula (2), formula (3) or formula (4); more preferably, the organic compound of the present invention has a structure as shown in formula (2).

[0044] Furthermore, in the organic compounds of the present invention, in formula (D), the sum of p and q is 1, or the sum of p and q is 2;

[0045] Preferably, p is 0 and q is 1; or preferably, p is 0 and q is 2; or preferably, p is 1 and q is 1.

[0046] The optimal value is p = 1 and q = 1.

[0047] Furthermore, in the organic compounds of the present invention, formula (D) is selected from any one of the following substituted or unsubstituted groups:

[0048] More preferably, formula (D) is selected from any one of the substituted or unsubstituted groups shown below:

[0049]

[0050] When the above groups contain substituents, the substituents are selected from one of the following: halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, and C3-C60 heteroaryl.

[0051] Furthermore, in equation (D), the R 2 and R 3 Each group is independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, naphthyl, anthracene, phenanthrene, indene, fluoranyl, triphenylene, pyrene, perylene, One of the following: 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl, benzo[a]fluorenyl, furanyl, thiopheneyl, pyrroleyl, benzo[a]furanyl, benzo[a]thiopheneyl, isobenzo[a]furanyl, indolyl, dibenzo[a]furanyl, dibenzo[a]thiopheneyl, carbazoyl, acridineyl, isobenzo[a]furanyl, isobenzo[a]thiopheneyl, acridineyl, pyridyl, benzo[a]carbazoyl, azacarbazoyl, phenothiazinyl, phenothiazinyl;

[0052] When the above-mentioned substituted or unsubstituted groups have substituted groups, the substituted groups are selected from one of halogens, C1-C10 chain alkyl groups, C1-C10 alkoxy groups, C3-C10 cycloalkyl groups, C6-C30 aryl groups, and C3-C30 heteroaryl groups.

[0053] Furthermore, the general formula compounds of the present invention are preferably the following specific compounds, but the present invention is not limited to the specific compounds L1-L220 shown below:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] A second objective of the present invention is to provide an application of the compound described in the first objective, wherein the compound is used in an organic electroluminescent device, preferably as a light-emitting layer material of the organic electroluminescent device.

[0065] The preparation process of the compound of this invention is simple and easy, the raw materials are readily available, it is suitable for mass production and scale-up, and it is very suitable for industrial applications.

[0066] The compound provided by this invention employs both cyano and triazine groups as electron-withdrawing groups on the benzene ring of the parent nucleus of general formula (1), which causes the compound to exhibit a red shift in luminescence, while group D... 1 By employing benzocarbazole-based donor groups, the excited-state energy levels of the compounds can be lowered, thereby enhancing their rigidity, luminescent efficiency, and carrier transport performance. When used in organic electroluminescent devices, the compounds of this invention achieve high luminescent efficiency. Furthermore, due to their excellent carrier transport efficiency, the device voltage can be reduced, making them suitable for use as luminescent dyes, particularly as orange luminescent dyes. The compounds of this invention can also act as sensitizers, working together with the host material and dye to achieve a good luminescent layer. Applications include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, organic thin-film solar cells, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper, with organic electroluminescent devices being preferred.

[0067] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and at least one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layers contain at least one compound described in the present invention.

[0068] The organic electroluminescent device of the present invention has a structure consistent with existing devices, for example including an anode layer, multiple light-emitting functional layers and a cathode layer; the multiple light-emitting functional layers include at least a light-emitting layer, wherein the light-emitting layer contains the above-mentioned organic compound of the present invention.

[0069] OLED devices prepared using the compounds of this invention have low start-up voltage, high luminous efficiency, and better lifespan, which can meet the current requirements of panel and display manufacturers for high-performance materials.

[0070] Specifically, another technical solution of the present invention provides an organic electroluminescent device, including a substrate, and an anode layer, a plurality of light-emitting functional layers and a cathode layer sequentially formed on the substrate; the light-emitting functional layers include at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer and an electron transport layer, wherein the electron blocking layer contains at least one of the above-mentioned compounds.

[0071] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0072] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0073] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0074] Organic material layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic material layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0075] The hole transport region is located between the anode and the light-emitting layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), wherein the electron blocking layer uses the compound represented by Formula I of this invention.

[0076] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include compounds shown below HT-1 to HT-51; or any combination thereof.

[0077]

[0078]

[0079]

[0080] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0081]

[0082] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0083] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0084] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of pH-1 to pH-85.

[0085]

[0086]

[0087]

[0088]

[0089] In this invention, the light-emitting layer dopant is one or more of the TADF materials represented by general formula (1).

[0090] In this invention, the TADF material represented by general formula (1) can not only be used as a luminescent material, but also as a sensitizer for fluorescent dyes. That is, in addition to the main material, the luminescent layer also includes dopant one and dopant two. Dopant one is selected from one or more combinations of the TADF materials represented by general formula (1).

[0091] Dopant 2 may be selected from, but is not limited to, one or more combinations of the following:

[0092]

[0093]

[0094] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0095] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0096]

[0097]

[0098]

[0099]

[0100] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Yb, Li or Ca.

[0101] Compared with the prior art, the present invention has the following beneficial effects:

[0102] This invention provides a solution.

[0103] In addition, the preparation process of the compounds of the present invention is simple and easy to implement, the raw materials are readily available, and it is suitable for mass production scale-up. Detailed Implementation

[0104] The technical solution of the present invention will be further described in more detail below. Those skilled in the art should understand that the embodiments described are merely illustrative of the invention and should not be considered as specific limitations thereof.

[0105] Method for obtaining the compound of the present invention

[0106] The compounds represented by general formula (1) of this invention can be obtained by known methods, such as by known organic synthesis methods. An exemplary synthetic route is given below, but those skilled in the art can also obtain them by other known methods.

[0107] Synthesized compounds

[0108] Synthesis Example 1: Synthesis of L1

[0109]

[0110] Synthesis of intermediate L1-1:

[0111] At room temperature, add A (50g, 273mmol), B (87.8g, 328mmol), tetrakis(triphenylphosphine)palladium (1.0g, 2.73mmol), and potassium carbonate (75.5g, 546mmol) to a 2L single-necked flask, along with Dioxane / H2O (900ml / 300ml). Purge with nitrogen for protection, heat to 80°C, and react for 4 hours.

[0112] The reaction was stopped, the temperature was lowered, and column chromatography was performed. 92 g of a white solid was obtained. Mass spectrometry analysis determined the molecular ion mass to be 370.6 (theoretical value: 370.1).

[0113] Synthesis of compound L1:

[0114] At room temperature, L1-1 (5g, 13.5mmol), C (7.33g, 33.7mmol), cesium carbonate (17.6g, 54mmol), and DMF (200ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0115] The reaction was stopped, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 8.1 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 764.8 (theoretical value: 764.2).

[0116] Synthesis Example 2: Synthesis of L32:

[0117]

[0118] At room temperature, L1-1 (5g, 13.5mmol), D (10.7g, 33.7mmol), cesium carbonate (17.6g, 54mmol), and DMF (200ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0119] The reaction was stopped, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 9.2 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 964.7 (theoretical value: 964.3).

[0120] Synthesis Example 3: Synthesis of L37:

[0121]

[0122] At room temperature, L1-1 (5g, 13.5mmol), D (9.02g, 33.7mmol), cesium carbonate (17.6g, 54mmol), and DMF (200ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0123] The reaction was stopped, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 8.7 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 864.6 (theoretical value: 864.3).

[0124] Synthesis Example 4: Synthesis of L40:

[0125]

[0126] Synthesis of intermediate L40-1:

[0127] At room temperature, L1-1 (5g, 13.5mmol), F (3.25g, 12.15mmol), potassium carbonate (2.8g, 20.25mmol), and DMF (150ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 45 degrees Celsius. The reaction was carried out for 6 hours.

[0128] The reaction was stopped, the temperature was lowered, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 5.1 g of a yellow solid was obtained. The molecular ion mass determined by mass spectrometry was 617.4 (theoretical value: 617.2).

[0129] Synthesis of compound L40:

[0130] At room temperature, L40-1 (5g, 8.1mmol), D (3.25g, 12.14mmol), cesium carbonate (5.27g, 16.2mmol), and DMF (150ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0131] The reaction was stopped, the temperature was lowered, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 3.7 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 864.6 (theoretical value: 864.3).

[0132] Synthesis Example 5: Synthesis of L114

[0133]

[0134] Synthesis of intermediate L114-1:

[0135] At room temperature, M (50g, 273mmol), N (87.8g, 328mmol), tetraphenylphosphine palladium (1.0g, 2.73mmol), and potassium carbonate (75.5g, 546mmol), along with Dioxane / H2O (900ml / 300ml), were added to a 2L single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 80°C. The reaction was allowed to proceed for 4 hours.

[0136] The reaction was stopped, the temperature was lowered, and column chromatography was performed. 85 g of a white solid was obtained. The molecular ion mass determined by mass spectrometry was 370.6 (theoretical value: 370.1).

[0137] Synthesis of compound L114:

[0138] At room temperature, L114-1 (5g, 13.5mmol), K (9.02g, 33.7mmol), cesium carbonate (13.2g, 40.5mmol), and DMF (200ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0139] The reaction was stopped, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 7.5 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 864.8 (theoretical value: 864.3).

[0140] Synthesis Example 6: Synthesis of L121

[0141]

[0142] Synthesis of compound L121:

[0143] At room temperature, L114-1 (5g, 13.5mmol), N (10.7g, 33.7mmol), cesium carbonate (13.2g, 40.5mmol), and DMF (200ml) were added to a 500ml single-necked flask. Nitrogen was used for purging and protection, and the temperature was raised to 100 degrees Celsius. The reaction was carried out for 16 hours.

[0144] The reaction was stopped, the reaction solution was injected into water, ammonium chloride solid was added, the mixture was stirred, the solid was filtered, and column chromatography was performed. 8.7 g of a red solid was obtained. The molecular ion mass determined by mass spectrometry was 964.8 (theoretical value: 964.3).

[0145] Example 1

[0146] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a acetone:ethanol mixed solvent, baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0147] The glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of <1×10⁻⁶. -5Pa, on the aforementioned anolyte film, a 10 nm HT-4:HI-3 (97 / 3, w / w) mixture was vacuum thermally deposited as a hole injection layer, a 60 nm HT-4 compound as a hole transport layer, and a 5 nm HT-51 compound as an electron blocking layer; a 40 nm PH54:L1:FD20 (100:40:1, w / w / w) ternary mixture was deposited as a light-emitting layer; a 5 nm PH-28 compound was deposited as a hole blocking layer; a 25 nm ET-69:ET-57 (50 / 50, w / w) compound was deposited as an electron transport layer; a 1 nm LiF compound was deposited as an electron injection layer; and a 150 nm aluminum alloy was deposited as a cathode. The total deposition rate of all organic layers and LiF was controlled at 0.1 nm / s, and the deposition rate of the metal electrode was controlled at 1 nm / s.

[0148] The fabrication process of the organic electroluminescent devices provided in Examples 2-6 and Comparative Examples 1-4 is the same as that in Example 1, except that the dye L1 in the light-emitting layer is replaced with the compounds shown in Table 1.

[0149] The molecular structural formulas of the comparative compounds M1, M2, M3, and M4 used in this invention are as follows:

[0150] M1 (CN109641880A), M2 (WO2021046523A), M3 (CN112334463A), M4 (US20190058130A).

[0151]

[0152] Device testing methods (including equipment and testing conditions):

[0153] The organic electroluminescent devices prepared by the above process were subjected to the following performance measurements:

[0154] Under the same brightness, the driving voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Examples 1-6 and Comparative Examples 1-4 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the measurement was performed when the brightness of the organic electroluminescent device reached 10000 cd / m². 2 The voltage at that time is the driving voltage; when measured with an integrating sphere, 1000 cd / m 2 The external quantum efficiency of the organic electroluminescent devices prepared in Examples 1-13 and Comparative Examples 1-4.

[0155] The performance data of the organic electroluminescent devices prepared in Examples 1-13 and Comparative Examples 1-4 are detailed in Table 1 below.

[0156] Table 1:

[0157] Comparative Example 1 M1 1000.00 5.7 18.6 Comparative Example 2 M2 1000.00 5.6 17.5 Comparative Example 3 M3 1000.00 5.8 18.1 Comparative Example 4 M4 1000.00 5.9 17.9 Example 1 L1 1000.00 4.5 21.1 Example 2 L9 1000.00 4.3 20.0 Example 3 L28 1000.00 4.8 19.6 Example 4 L32 1000.00 4.6 19.8 Example 5 L37 1000.00 4.7 20.7 Example 6 L40 1000.00 5.1 20.4 Example 7 L114 1000.00 4.6 19.6 Example 8 L121 1000.00 4.9 20.9 Example 9 L176 1000.00 5.3 19.0 Example 10 L184 1000.00 5.2 18.9 Example 11 L196 1000.00 5.3 19.0 Example 12 L204 1000.00 4.8 19.1 Example 13 L212 1000.00 4.9 19.7

[0158] As shown in Table 1, when the compounds of this invention are used as dye materials in the emitting layer of organic electroluminescent devices, they exhibit higher efficiency and lower voltage compared to comparative compounds M1, M2, and M4. This is likely because the dibenzo-carbazole structure can more effectively lower the excited-state energy level of the compound compared to carbazole, benzofuranocarbazole, and benzothiophenecarbazole, resulting in a better match between the sensitizer's luminescence and the dye's absorption spectrum, thus improving device efficiency. Simultaneously, the dibenzo-carbazole structure provides higher carrier mobility, leading to a lower voltage. Compared to comparative compound M3, M3 has only one benzo-carbazole electron-donating group, resulting in a more bluish light color and poorer matching with the dye, thus lower efficiency. Furthermore, the fewer conjugated groups lead to poorer carrier transport performance, resulting in a higher voltage than the compounds of this invention.

[0159] The present invention has been illustrated with the above embodiments to explain the detailed method of the present invention. However, the present invention is not limited to the detailed method described above, that is, it does not mean that the present invention must rely on the detailed method described above to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound having the structure shown in formula (1): （1） In formula (1): R 1 Selected from C1~C20 chain alkyl groups; Ar 1 and Ar 2 Each is independently selected from C6~C20 aryl groups; n is 0 or 1, m is an integer from 2 to 4, and the sum of m and n is an integer from 2 to 4; D 1 For groups represented as in formula (D): （D） In formula (D): The position of the bond that the group is attached to; Ring B and ring C are each independently a benzene ring; p and q are each independent integers from 0 to 2, and p and q are not both 0 at the same time; R 2 and R 3 Representing single substituents to the maximum permissible substituents, R 2 and R 3 Each is independently selected from one of hydrogen, C1~C20 chain alkyl, or C6~C60 aryl.

2. The organic compound according to claim 1, having a structure as shown in formula (1-1) or formula (1-2): （1-1） （1-2） In equations (1-1) and (1-2), R 1 Ar 1 Ar 2 m, n, D 1 The definitions are the same as those in equation (1).

3. The organic compound according to claim 2, having a structure as shown in formula (1-1).

4. The organic compound according to claim 1 or 2, wherein m is 2 in formula (1), formula (1-1) and formula (1-2).

5. The organic compound according to any one of claims 1, 2 or 3, wherein n is 0 in formula (1), formula (1-1) and formula (1-2).

6. The organic compound according to claim 1, having a structure as shown in any one of formulas (2) to (10): In equations (2) to (10), Ar 1 Ar 2 D 1 The definitions are the same as those in equation (1), D 1’ Definition and D 1 Same, D 1 With D 1’ The structures chosen by each may be the same or different.

7. The organic compound according to claim 6, having a structure as shown in any one of formula (2), formula (3) or formula (4).

8. The organic compound according to claim 6, having the structure shown in formula (2).

9. The organic compound according to claim 1, wherein in formula (D), the sum of p and q is 1, or the sum of p and q is 2.

10. The organic compound according to claim 1, wherein in formula (D), p is 0 and q is 1; or p is 0 and q is 2; or p is 1 and q is 1.

11. The organic compound according to claim 1, wherein formula (D) is selected from any one of the following substituted or unsubstituted groups: 。 12. The organic compound according to claim 11, wherein formula (D) is selected from any one of the following groups: 。 13. An organic compound having the structure shown below: 。 14. The use of the organic compound of any one of claims 1-13 as a functional material in an organic electronic device, wherein the organic electronic device is selected from organic electroluminescent devices, optical sensors, solar cells, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; The organic compound is used as a light-emitting layer material in organic electroluminescent devices.

15. The application according to claim 14, used as a luminescent dye in the luminescent layer of an organic electroluminescent device.

16. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and wherein the light-emitting layer contains an organic compound as described in any one of claims 1-13.

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