Organic light-emitting compound and application thereof

Abstract

The embodiment of the invention provides an organic light-emitting compound and application thereof. The organic light-emitting compound has a first structure, and the first structure is formed by bonding a first structural unit as shown in a formula (I) and a second structural unit as shown in a formula (II); according to the organic light-emitting compound provided by the embodiment of the invention, the first structural unit as shown in the formula (I) is used as a structural framework, and the structural framework is modified through the second structural unit as shown in the formula (II), so that relatively excellent light-emitting performance can be obtained, and blue light can be realized, and therefore, the organic light-emitting compound can be efficiently applied to organic electronic devices; the luminous efficiency and the service life of an organic electronic device are improved.

Description

Technical Field

[0001] Embodiments of the present application relate to the technical field of organic light-emitting materials, and in particular to an organic light-emitting compound, and a composition, a mixture, an organic electronic device, a display screen, and an electronic device comprising the organic light-emitting compound. Background Art

[0002] Organic light emitting diode (OLED) devices are widely used in display devices of terminal equipment due to their advantages such as self-luminescence, low driving voltage, wide viewing angle, high contrast, and high responsiveness. Organic light-emitting materials, as the core component of OLED devices, are of great significance to the performance of OLED devices.

[0003] With the development of display device technology, blue light organic light-emitting materials have become a research hotspot in the field of OLED devices. At present, blue light organic light-emitting materials mostly use traditional fluorescent materials such as pyrene, anthracene, and perylene. However, the full width at half maximum (FWHM) of the emission spectrum of this type of material is wide, the color purity is poor, and it is difficult to achieve deep blue light display effects. In addition, there are problems such as low luminous efficiency and short life in OLED devices. Therefore, blue light organic light-emitting materials with excellent luminous performance are still relatively scarce. Summary of the invention

[0004] The embodiments of the present application provide an organic light-emitting compound, and a composition, a mixture, an organic electronic device, a display screen and an electronic device comprising the organic light-emitting compound. The organic light-emitting compound can have relatively excellent light-emitting performance, which is conducive to the realization of blue light, and thus is conducive to efficient application in organic electronic devices, thereby improving the light-emitting efficiency and service life of the organic electronic devices.

[0005] In a first aspect, an organic light-emitting compound is provided, wherein the organic light-emitting compound has a first structure, wherein the first structure is a structure formed by bonding a first structural unit represented by formula (I) and a second structural unit represented by formula (II) to each other;

[0006]

[0007] Wherein, in the formula (I) and the formula (II),

[0008] Ring A, Ring B, and Ring K are each independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;

[0009] V is selected from boron atom, nitrogen atom, phosphorus atom, aluminum atom, >CR 1 -, >P(=O)-;

[0010] Each U and W are independently selected from -C(R 1 ,R 2 )-、-NR 1 -、-P(=O)R 1 Any one of -;

[0011] Each X, each Y and each Z are independently selected from nitrogen atoms, or >CR 1 -;

[0012] Among them, each R 1 and R 2 Each is independently selected from any one of a hydrogen atom, a deuterium atom, a halogen atom, a silyl group, a keto group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a formyl group, a carbamoyl group, a haloformyl group, a carbonyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms.

[0013] It should be understood that the embodiment of the present application uses the first structural unit shown in the above formula (I) as the structural skeleton of the organic light-emitting compound, and constructs the first structure by bonding the second structural unit shown in formula (II) to the first structural unit as the structural skeleton, that is, constructs the structure of the organic light-emitting compound.

[0014] In the above technical scheme, the organic light-emitting compound uses the first structural unit shown in formula (I) as the structural skeleton, and introduces the second structural unit shown in formula (II) to modify the structural skeleton. In this way, the organic light-emitting compound can obtain better luminescence performance, which is conducive to the realization of blue light, and can be efficiently applied to organic electronic devices to improve the luminescence efficiency and service life of organic electronic devices.

[0015] First, the second structural unit is a triphenylene unit, which has high rigidity, can suppress the large-scale molecular bond vibration in the excited state, and reduce the number of freely rotating phenyl groups in the organic light-emitting compound. This is conducive to narrowing the half-maximum full width of the luminescence spectrum of the organic light-emitting compound, improving the color purity and photoluminescence quantum yield of the organic light-emitting compound, and making the organic light-emitting compound have better luminescence performance, thereby helping to improve the luminescence efficiency and service life of organic electronic devices.

[0016] Secondly, the second structural unit can act as a steric hindering group to inhibit the intermolecular aggregation in the organic light-emitting compound in the solid state, which can reduce the aggregation quenching effect of the phosphor and increase the photoluminescence quantum yield of the organic light-emitting compound, thereby facilitating the improvement of the luminescence efficiency and service life of the organic electronic device.

[0017] Finally, the organic light-emitting compound constructed by the first structural unit and the second structural unit has a low degree of conjugation, and the second structural unit can be used as an electron-donating group to improve the electron-donating property of the organic light-emitting compound. This is conducive to adjusting the light color of the organic light-emitting compound, so that the light emission wavelength of the organic light-emitting compound moves toward the short-wave direction, thereby facilitating the realization of blue light, for example, achieving a deep blue light display effect.

[0018] Optionally, in some embodiments, each of the above R 1 and R 2 Each is independently selected from a keto group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted straight-chain alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain thioalkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic thioalkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted aryloxycarbonyl group having 7 to 20 carbon atoms.

[0019] In one example, the substituted linear alkyl group can be -CF3.

[0020] Optionally, in some embodiments, each of the above R 1 and R 2 They may also be each independently selected from crosslinkable groups.

[0021] In combination with the first aspect, in certain implementations of the first aspect, the first structural unit includes a skeleton and a ring structure connected to the skeleton, and the second structural unit is bonded to the ring structure via a connecting bond.

[0022] It should be understood that the first structural unit shown in formula (I) includes a skeleton and ring A, ring B and ring K connected to the skeleton, and the second structural unit shown in formula (II) can be bonded to any one of the rings A, B and K. For example, the second structural unit can be bonded to the ring K in the first structural unit via a connecting bond.

[0023] In combination with the first aspect, in certain implementations of the first aspect, the first structural unit includes a skeleton and a ring structure connected to the skeleton, and the second structural unit bonds to the first structural unit by replacing part of the ring structure.

[0024] It should be understood that the first structural unit shown in formula (I) includes a skeleton and ring A, ring B and ring K connected to the skeleton, and the second structural unit shown in formula (II) can be bonded to the first structural unit by replacing any one of the above rings A, B and K. For example, the second structural unit can be bonded to the first structural unit by replacing the ring A in the first structural unit.

[0025] It should also be understood that the second structural unit replacing part of the ring structure in the first structural unit may include the partial structure of the second structural unit replacing the partial ring structure connected to the skeleton in the first structural unit, or the partial structure of the second structural unit replacing the partial structure of the skeleton in the first structural unit.

[0026] In conjunction with the first aspect, in certain implementations of the first aspect, the general formula of the first structure is as follows: a )~Formula (i c ) as shown in any of the following:

[0027]

[0028] In combination with the first aspect, in certain implementations of the first aspect, the organic light-emitting compound has a formula (i a )~Formula (i c ) at least one of the first structures shown.

[0029] In the above technical scheme, the structure of the organic light-emitting compound can be flexibly adjusted according to actual production and design requirements, so that the organic light-emitting compound has at least one of the first structures shown in the above general formula, which is conducive to adjusting the luminescent properties of the organic light-emitting compound to meet different luminescent requirements.

[0030] In combination with the first aspect, in certain implementations of the first aspect, V is selected from a boron atom, and each U is independently selected from -NR 1 -.

[0031] In the above technical solution, the structural skeleton of the organic light-emitting compound can be a boron-nitrogen skeleton. The structure of the boron-nitrogen skeleton is relatively stable and simple to synthesize, which is conducive to obtaining a light-emitting material with a longer working life.

[0032] In a second aspect, a composition is provided, which comprises an organic solvent and at least one organic light-emitting compound as described in any one of the first aspects above.

[0033] In a third aspect, a mixture is provided, which comprises an organic functional material and at least one organic light-emitting compound as described in any one of the first aspect above; or, the mixture comprises an organic functional material and at least one composition as described in the second aspect above; wherein the organic functional material comprises at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminophore and a host material.

[0034] In a fourth aspect, an organic electronic device is provided, comprising: a first electrode and a second electrode arranged opposite to each other, and at least one functional layer located between the first electrode and the second electrode; wherein at least one functional layer comprises at least one organic light-emitting compound as described in any one of the first aspect; or comprises at least one composition as described in the second aspect; or comprises at least one mixture as described in the third aspect.

[0035] In some embodiments, the organic electronic device may be an organic solar cell, an organic field effect transistor, an organic thin film transistor, an organic optical detector, an organic sensor, an organic electroluminescent device, etc., which is not limited in the present application.

[0036] In combination with the fourth aspect, in certain implementations of the fourth aspect, the organic electronic device may be an organic electroluminescent device, at least one layer of which includes a light-emitting layer, and the light-emitting layer includes at least one organic light-emitting compound as described in any one of the first aspect above.

[0037] In some embodiments, the guest material in the light-emitting layer includes at least one organic light-emitting compound as described in any one of the first aspects above.

[0038] In combination with the fourth aspect, in certain implementations of the fourth aspect, at least one functional layer also includes at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer stacked in sequence, the light-emitting layer is located between the electron blocking layer and the hole blocking layer, and at least one of the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer and the electron transport layer includes at least one organic light-emitting compound as described in any one of the first aspect above.

[0039] In a fifth aspect, a display screen is provided, comprising a cover plate, a back plate, and the organic electronic device described in any one of the fourth aspects, wherein the organic electronic device is located between the back plate and the cover plate.

[0040] The organic electronic device may be an organic electroluminescent device.

[0041] In a sixth aspect, an electronic device is provided, comprising a housing assembly and the display screen described in the fifth aspect, wherein the display screen is located inside the housing assembly.

[0042] Among them, the beneficial effects of the second to sixth aspects mentioned above can refer to the beneficial effects of the first aspect mentioned above, and will not be repeated here. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] Figure 1 It is a structural schematic diagram of an electronic device provided in an embodiment of the present application.

[0044] Figure 2 It is a structural schematic diagram of a display screen provided in an embodiment of the present application.

[0045] Figure 3 It is a schematic diagram of the structure of an organic electronic device provided in an embodiment of the present application.

[0046] Figure 4 It is a schematic diagram of the structure of another organic electronic device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0047] To facilitate understanding of the embodiments provided in the present application, the following points are explained before introducing the embodiments of the present application.

[0048] In the description of the embodiments of the present application, a numerical range represented by “to” refers to a range that includes the numerical values ​​described before and after “to” as the lower limit and the upper limit.

[0049] In the description of the embodiments of the present application, "substituted group b having a carbon atom number" means that "substituent c (with no limited carbon atom number)" is substituted on "group b having a carbon atom number a", and the carbon atom number a is not the total carbon atom number of the substituent c and the group b.

[0050] In the description of the embodiments of the present application, a substituent may be further substituted by a substituent, and "substituted group a" may refer to group a being substituted by a substituent, and the substituent may be substituted by at least one further substituent or may be unsubstituted.

[0051] The technical solution in this application will be described below in conjunction with the accompanying drawings.

[0052] In order to facilitate a better understanding of the organic light-emitting compounds provided in the embodiments of the present application, the applicable application scenarios of the organic light-emitting compounds provided in the embodiments of the present application are first exemplified.

[0053] The organic light-emitting compounds provided in the embodiments of the present application can be applied to organic electronic devices, which may be organic electroluminescent devices, organic solar cells, organic field effect transistors, organic thin film transistors, organic optical detectors or organic sensors, etc., and the present application does not limit this.

[0054] For ease of description and understanding, an organic electroluminescent device in which an organic light-emitting compound is applied to electronic devices is used as an example for explanation below.

[0055] Figure 1 It is an electronic device 100 provided in the embodiment of the present application. The electronic device 100 may include but is not limited to mobile phones, tablet computers, e-readers, remote controllers, personal computers (PCs), laptop computers, personal digital assistants (PDAs), vehicle-mounted devices, network televisions, wearable devices, televisions, smart watches, smart bracelets and other products with display interfaces. The embodiment of the present application does not impose any special restrictions on the electronic device 100. It should be understood that for ease of description and understanding, Figure 1 The illustrated embodiment is described by taking the electronic device 100 as a mobile phone as an example.

[0056] like Figure 1 As shown, the electronic device 100 may include a housing assembly 10 and a display screen 20, wherein the display screen 20 may be located inside the housing assembly 10. The housing assembly 10 may be used to carry and protect the display screen 20, and the display screen 20 may be used for an active-matrix organic light-emitting diode or an active-matrix organic light-emitting diode (AMOLED) display scene or a micro-LED display scene, and the display screen 20 may be various self-luminous display screens, which are not limited in the present application.

[0057] along Figure 1 The AA cross section of the display module 20 can be observed. Figure 2 Schematic diagram of the cross-section structure shown.

[0058] like Figure 2As shown, the display screen 20 may include a cover plate 21, a display module 22 and a back plate 23. The display module 22 may be located between the cover plate 21 and the back plate 23. The cover plate 23 may protect the display module 22. For example, when the thickness of the display module 22 is small, the cover plate 23 may ensure the luminous performance and reliability of the display module 22, and may also ensure the bending performance of the display module 22 to avoid bending and fracture problems. The back plate 23 may play a supporting role to achieve a fixed setting of the display module 22. Exemplarily, the cover plate 21 and the display module 22 and the display module 22 and the back plate 23 may be fixed by bonding. For example, the cover plate 21 and the display module 22 and the display module 22 and the back plate 23 may be bonded by optically clear adhesive (OCA).

[0059] In some embodiments, the display module 22 may include a substrate 221 and an organic electroluminescent device (eg, an OLED device) 222 disposed on the substrate 221 .

[0060] Optionally, the substrate 221 may be a rigid substrate or a flexible substrate, which is not limited in the present application. When the substrate 221 is a rigid substrate, the material of the substrate 221 may include, but is not limited to, one or more of a glass substrate or a metal foil. When the substrate 221 is a flexible substrate, the material of the substrate 221 may include, but is not limited to, one or more of ethylene terephthalate, polyetheretherketone, polystyrene, polycarbonate, polyarylate, polyarylate, polyimide, polyvinyl chloride, polyethylene, or textile fiber.

[0061] The organic electroluminescent device 222 may be a current-driven light-emitting device using an organic light-emitting material as an active material, wherein the organic light-emitting material can emit light under the drive of an electric field through carrier injection and recombination drive.

[0062] At present, the research on organic light-emitting materials mainly focuses on blue light organic light-emitting materials. However, the existing blue light organic light-emitting materials mostly use traditional fluorescent materials such as pyrene, anthracene, and perylene. The FWHM of the emission spectrum of such materials is wide, the color purity is poor, and it is difficult to achieve deep blue light display effect. In addition, there are problems such as low luminous efficiency and short life in OLED devices (for example, in organic electroluminescent devices 222). Therefore, blue light organic light-emitting materials with excellent luminous performance are still relatively scarce.

[0063] Based on the above content, an embodiment of the present application provides an organic light-emitting compound, which can have relatively excellent light-emitting performance and is conducive to the realization of blue light, so that it can be efficiently applied to organic electronic devices to improve the light-emitting efficiency and service life of organic electronic devices.

[0064] The present application provides an organic light-emitting compound, which may have a first structure. The first structure may be a structure formed by bonding a first structural unit represented by the following formula (I) and a second structural unit represented by the following formula (II):

[0065]

[0066] In the above formulae (I) and (II), "A", "B" and "K" within a circle are symbols indicating the ring structure represented by the circle.

[0067] In the above formula (I) and the above formula (II), the A ring, the B ring and the K ring can be independently selected from substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups;

[0068] V can be selected from boron atoms, nitrogen atoms, phosphorus atoms, aluminum atoms, >CR 1 -, >P(=O)-;

[0069] Each U and W can be independently selected from -C(R 1 ,R 2 )-、-NR 1 -、-P(=O)R 1 Any one of -;

[0070] Each X, each Y and each Z can be independently selected from nitrogen atoms, or >CR 1 -;

[0071] Among them, each of the above R 1 and R 2 Each of the above groups may be independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a silyl group, a keto group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a formyl group, a carbamoyl group, a haloformyl group, a carbonyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms.

[0072] It should be noted that the above “>” represents two bonding bonds, for example, “>CR 1 -" indicates CR 1 With three bonding positions, CR 1 Can bond to three groups.

[0073] It should be understood that the embodiment of the present application uses the first structural unit as a skeleton and bonds the second structural unit to the first structural unit to construct a first structure, that is, to construct the structure of an organic light-emitting compound.

[0074] In the embodiment of the present application, the structure of the organic light-emitting compound is based on the first structural unit shown in formula (I) as the skeleton, and the skeleton is modified by introducing the second structural unit shown in formula (II). In this way, the organic light-emitting compound can obtain excellent light-emitting performance, which is conducive to the realization of blue light, and can be efficiently applied to organic electronic devices to improve the light-emitting efficiency and service life of organic electronic devices.

[0075] First, the second structural unit is a triphenylene unit, which has high rigidity, can suppress the large-scale molecular bond vibration in the excited state, and reduce the number of freely rotating phenyl groups in the organic light-emitting compound. This is conducive to narrowing the FWHM of the luminescence spectrum of the organic light-emitting compound, improving the color purity and photoluminescence quantum yield (PLQY) of the organic light-emitting compound, and making the organic light-emitting compound have better luminescence performance, thereby helping to improve the luminescence efficiency and service life of organic electronic devices.

[0076] Secondly, the second structural unit can act as a steric hindering group to inhibit the intermolecular aggregation in the organic light-emitting compound in the solid state. This can reduce the aggregation quenching effect of the phosphor and improve the PLQY of the organic light-emitting compound, thereby helping to improve the luminescence efficiency and service life of the organic electronic device.

[0077] Finally, the organic light-emitting compound constructed by the first structural unit and the second structural unit has a low degree of conjugation, and the second structural unit can be used as an electron-donating group to improve the electron-donating property of the organic light-emitting compound. This is conducive to adjusting the light color of the organic light-emitting compound, so that the light emission wavelength of the organic light-emitting compound moves toward the short-wave direction, thereby facilitating the realization of blue light, for example, achieving a deep blue light display effect.

[0078] Optionally, in some embodiments, each of the above R 1 and R 2Each is independently selected from a keto group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted straight-chain alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain alkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted branched-chain thioalkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted cyclic thioalkoxy group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted aryloxycarbonyl group having 7 to 20 carbon atoms.

[0079] In one example, the substituted linear alkyl group can be -CF3.

[0080] Optionally, in some embodiments, each of the above R 1 and R 2 They may also be each independently selected from crosslinkable groups.

[0081] In some embodiments, in the first structural unit shown in formula (I), the first structural unit may include a skeleton and a ring structure connected to the skeleton. Specifically, the first structural unit may include a skeleton and an A ring, a B ring and a K ring connected to the skeleton, and the skeleton may include a connection position V and two connection positions U.

[0082] In a possible implementation, the second structural unit represented by formula (II) can be bonded to the ring structure in the first structural unit represented by formula (I) via a connecting bond.

[0083] In one example, a partial structure in the second structural unit can be bonded to any one of the rings A, B and K through a connecting bond. For example, the general formula of the structure of the organic light-emitting compound, that is, the general formula of the first structure can be as follows (i a ) or formula (i b ) as shown:

[0084]

[0085] For the above formula (i a ) is equivalent to the structure formed by the W in the second structural unit shown in formula (II) being bonded to the K ring in the first structural unit shown in formula (I) through a connecting bond.

[0086] For the above formula (i b ) is equivalent to the structure formed by the W in the second structural unit shown in formula (II) being bonded to the A ring in the first structural unit shown in formula (I) through a connecting bond.

[0087] In another example, a partial structure in the second structural unit can also be bonded to any two rings of the A ring, the B ring, and the K ring through a connecting bond. For example, W in the second structural unit shown in formula (II) can be bonded to the A ring and the K ring in the first structural unit shown in formula (I) through a connecting bond to form the first structure. That is, W in the second structural unit can be bonded to the first structural unit by replacing the connecting position U on the skeleton in the first structural unit.

[0088] It can be understood that the connecting bond may refer to a single bond, a double bond, a triple bond or a connecting group, and the present application does not impose any limitation on this.

[0089] In another possible implementation, the second structural unit represented by formula (II) can be bonded to the first structural unit by replacing part of the ring structure connected to the skeleton in the first structural unit represented by formula (I).

[0090] In one example, the second structural unit can be bonded to the first structural unit by replacing any one of the A ring, the B ring and the K ring. For example, the general formula of the structure of the organic light-emitting compound, that is, the general formula of the first structure can be as follows (i c ) as shown:

[0091]

[0092] For the above formula (i c ) is equivalent to the structure formed by the second structural unit shown in formula (II) by replacing the A ring in the first structural unit shown in formula (I) to bond with the first structural unit.

[0093] It can be understood that the replacement of a portion of the ring structure in the first structural unit by the second structural unit can include the replacement of a portion of the ring structure in the first structural unit connected to the skeleton by a portion of the second structural unit, and can also include the replacement of a portion of the skeleton structure in the first structural unit by a portion of the second structural unit. c ), W in the second structural unit shown in formula (II) also replaces the connection position U on the skeleton in the first structural unit shown in formula (I).

[0094] It should be noted that, formula (i a )~Formula (i c ) shown in the first structure, that is, formula (i a )~Formula (i cThe structure of the organic light-emitting compound shown in formula (I) is only an example, which can be adjusted according to the actual preparation. The present application does not impose any restrictions on this. It is sufficient to ensure that the structure of the organic light-emitting compound is a structure formed by the first structural unit shown in formula (I) and the second structural unit shown in formula (II) are bonded to each other.

[0095] In some embodiments, the organic light-emitting compound may include the above-mentioned formula (i a )~Formula (i c ) is at least one of the first structures shown in ). For example, the organic light-emitting compound may only include the formula (i a ), formula (i b ) or formula (i c ) shown in the first structure; or, the organic light-emitting compound may include (i a ), formula (i b ) and formula (i c ) is not limited to the first structure shown in the present application.

[0096] It is understandable that in the embodiments of the present application, the structure of the organic light-emitting compound can be flexibly prepared according to actual production and design requirements, so that the organic light-emitting compound has the above general formula (i a )~Formula (i c ) is at least one of the first structures shown, which is beneficial to adjust the luminescent properties of the organic luminescent compound to meet different luminescent requirements.

[0097] In one example, in the first structural unit represented by formula (I), V can be selected from a boron atom, and two U can be independently selected from -NR 1 -. That is, the first structural unit can be a boron nitrogen skeleton. The boron nitrogen skeleton has a stable structure and is simple to synthesize, which is conducive to obtaining a luminescent material with a long life.

[0098] In some embodiments, the first structure may be specifically as follows:

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] The meaning of the atomic groups involved in the above-mentioned application is explained below. It should be understood that, unless otherwise indicated, the following atomic groups have the following meanings. Any undefined atomic groups have their technically recognized meanings.

[0110] In the embodiments of the present application, "substituted or unsubstituted" may refer to being unsubstituted or substituted by one or more substituents selected from the following: deuterium atoms, halogen groups, cyano groups, isocyano groups, keto groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amide groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, formyl groups, carbamoyl groups, haloformyl groups, phosphine oxide groups, alkyl groups, cycloalkyl groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfonyl groups, arylsulfonyl groups, alkenyl groups, silyl groups, boron groups, amine groups, arylphosphino groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups or heterocyclic groups. Alternatively, "substituted or unsubstituted" may also refer to being unsubstituted or substituted by substituents connected by at least two substituents in the above-mentioned substituents. For example, "a substituent in which at least two of the substituents exemplified above are connected" may be a biphenyl group, which may be considered as an aryl group in the embodiments of the present application, and may also be understood as a substituent in which two phenyl groups are connected.

[0111] In the embodiments of the present application, "ring atoms" may refer to the number of atoms constituting the ring itself in a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) obtained by bonding atoms to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. For example, the number of ring atoms of a benzene ring is 6, the number of atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

[0112] The halogen atom may refer to a fluorine atom (F), a chlorine atom (Cl), a bromine atom (Br), or an iodine atom (I).

[0113] Silyl groups can be represented by the group -SiR a R b R c Indicates. Among them, R a , R b and R cCan be independently selected from any one of hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl, and the application is not limited to this. The example of silyl group can include but is not limited to trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl etc.

[0114] The keto group may refer to a -(C=O)- group. In the present embodiment, the number of carbon atoms in the keto group is not limited. For example, the number of carbon atoms in the keto group is preferably 1 to 20.

[0115] Cyano, which may also be called "nitrile," may refer to the group -CN.

[0116] Isocyano may refer to the group -NC.

[0117] Isocyanate group may refer to the group -NCO.

[0118] Thiocyanate group may refer to the group -S—C≡N.

[0119] Isothiocyanate may refer to the group -N=C=S.

[0120] Formyl may refer to the group -CHO.

[0121] Carbamoyl may refer to the group -CONH2.

[0122] The haloformyl group may refer to the group -COX (X may refer to F, Cl, Br, or I halogen elements).

[0123] Nitro may refer to the group -NO2.

[0124] Hydroxyl may be referred to as the group -OH.

[0125] The carbonyl group may refer to a -CO- group. In the embodiments of the present application, the number of carbon atoms in the carbonyl group is not limited. For example, the number of carbon atoms in the carbonyl group is preferably 1 to 20.

[0126] The ester group may refer to a -COO- group. The ester group may include, for example, a carbonate group, a sulfonate group, a phosphate group, etc. The ester group may be substituted or unsubstituted, such as an alkyl ester group, an alkenyl ester group, an aryl ester group, etc.

[0127] Boryl can be represented by the group -BR a R b Indicates. Among them, R a and R bEach of the boryl groups may be independently selected from hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, and the present application does not limit this. Examples of boryl groups may include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc.

[0128] Alkyl can refer to a monovalent saturated aliphatic hydrocarbon group with carbon atoms, and the alkyl group can be straight or branched, and the number of carbon atoms in the alkyl group is not limited. Exemplarily, the number of carbon atoms of the alkyl group can be 1 to 40. Further, the number of carbon atoms of the straight-chain alkyl group can be preferably 1 to 20, and the number of carbon atoms of the straight-chain alkyl group can be preferentially 3 to 20. Further, the number of carbon atoms of the straight-chain alkyl group can be preferably 1 to 10, and the number of carbon atoms of the branched alkyl group can be preferentially 3 to 10. Examples of alkyl groups can include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, etc. Substituted alkyl groups can include, but are not limited to -CF3.

[0129] Cycloalkyl may refer to a cyclic alkyl having a single ring or a polycyclic cyclic alkyl including a fused, bridged, and spiro ring system. In the present embodiment, the number of carbon atoms in the cycloalkyl is not limited, and illustratively, the number of carbon atoms in the cycloalkyl may be 3 to 40. Further, the number of carbon atoms in the cycloalkyl may preferably be 3 to 20. Exemplarily, examples of cycloalkyl may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, etc.

[0130] Alkoxy can refer to group-O-alkyl, wherein alkyl is as defined above in the embodiment of the present application.Alkoxy can be straight chain, branched or cyclic, and the number of carbon atoms in the alkoxy is not limited. Exemplarily, the number of carbon atoms in a straight chain alkoxy can be 1 to 40, the number of carbon atoms in a branched chain alkoxy can be 3 to 40, and the number of carbon atoms in a cyclic alkoxy can be 3 to 40. Further, the number of carbon atoms in a straight chain alkoxy can be preferably 1 to 20, the number of carbon atoms in a branched chain alkoxy can be preferentially 3 to 20, and the number of carbon atoms in a cyclic alkoxy can be preferentially 3 to 20. The example of alkoxy includes but is not limited to methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc.

[0131] Alkoxycarbonyl may refer to a group -COO-alkyl, wherein alkyl is as defined above in the examples of the present application. In the examples of the present application, the number of carbon atoms in the alkoxycarbonyl is not limited, and illustratively, the number of carbon atoms in the alkoxycarbonyl is preferably 2 to 20.

[0132] Alkenyl can refer to a straight or branched hydrocarbon group having carbon atoms and at least 1 and preferably 1 to 2 double bond unsaturated sites. Alkenyl can be straight or branched, and there is no restriction on the number of carbon atoms in the alkenyl. Exemplarily, the number of carbon atoms in the alkenyl can be 2 to 20. Further, the number of carbon atoms in the alkenyl can preferably be 2 to 6.

[0133] Alkynyl may refer to a straight or branched monovalent hydrocarbon group having carbon atoms and having at least 1 and preferably 1 to 2 triple bond unsaturated sites. Alkynyl may be straight or branched, and there is no limitation on the number of carbon atoms in the alkynyl. Exemplarily, the number of carbon atoms in the alkynyl may preferably be 2 to 20. Further, the number of carbon atoms in the alkynyl may preferably be 2 to 6.

[0134] Aryl may refer to a monovalent aromatic carbocyclic group having a single ring (such as present in phenyl) or a ring system having multiple condensed rings (examples of such aromatic ring systems include naphthyl, anthracenyl and indenyl), and the above condensed rings may or may not be aromatic, provided that the attachment point is through the atoms of the aromatic ring. The embodiments of the present application do not limit the number of ring atoms in the aryl group. Exemplarily, the aryl group has 5 to 60 ring atoms. Moreover, the embodiments of the present application do not limit the number of carbon atoms in the aryl group. Exemplarily, the number of carbon atoms in the aryl group is 6 to 60. Furthermore, the number of carbon atoms in the aryl group may preferably be 6 to 30. Exemplarily, examples of monocyclic aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, etc., and examples of polycyclic aryl groups may include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, indenyl, phenylene, fluorenyl, triphenylene, etc.

[0135] In the embodiments of the present application, the above description of the aryl group can also be applied to the aryl groups in the arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamine group, arylalkenyl group, alkylaryl group, arylamine group and arylheteroarylamine group.

[0136] Heteroaryl may refer to an aromatic group having carbon atoms and heteroatoms selected from at least one group consisting of O, N, P, S, Si and Se in the ring, and the heteroaryl may have a monocyclic ring or multiple condensed rings (including fused, bridged and spirocyclic ring systems). The present application embodiment does not limit the number of ring atoms in the heteroaryl. Exemplarily, the heteroaryl has 5 to 60 ring atoms. And, the present application embodiment does not limit the number of carbon atoms in the heteroaryl. Exemplarily, the number of carbon atoms in the heteroaryl can be 6 to 40. Further, the number of carbon atoms in the heteroaryl can be 3 to 30. Such heteroaryl can have a monocyclic ring (such as pyridyl, imidazolyl or furanyl) or multiple condensed rings in the ring system (for example, in groups such as indolizinyl, quinolyl, benzofuran, benzimidazolyl or benzothiophenyl), wherein at least one ring in the ring system is aromatic.

[0137] Illustrative examples of heterocyclic and heteroaryl groups include, but are not limited to, pyridinyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, quinolizinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinoline, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, dioxathinyl, pyrid ... azanaphthyl, triazaindenyl, indolyl, indolinyl, azinyl, acridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolinoindolyl, phthalazinyl, imidazopyrimidinyl, phenothiazinyl, piperidinyl, piperazinyl, imidazopyridinyl, indolizinyl, and the like.

[0138] Aryloxy can refer to the group -O-aryl, wherein aryl is as defined above for aryl in the embodiments of the present application. The embodiments of the present application do not limit the number of ring atoms in the aryloxy. Exemplarily, the aryloxy has 5 to 60 ring atoms. For example, aryloxy includes phenoxy, naphthoxy, and the like.

[0139] Aryloxycarbonyl may refer to an aryl group connected to a carbonyl group, wherein the aryloxy group and the carbonyl group are as defined above in the embodiments of the present application. The embodiments of the present application do not limit the number of carbon atoms in the aryloxycarbonyl group. Exemplarily, the number of carbon atoms in the aryloxycarbonyl group may be 7 to 40. Further, the number of carbon atoms in the aryloxycarbonyl group may preferably be 7 to 20.

[0140] Thioalkoxy can refer to group -OSR (R can be alkyl or aryl), wherein alkyl and aryl are as defined above in the embodiments of the present application for alkyl and aryl.Thioalkoxy can be straight chain, straight chain or cyclic, and the number of carbon atoms in the thioalkoxy is not limited. Exemplarily, the number of carbon atoms in a straight chain thioalkoxy can be 1 to 40, the number of carbon atoms in a branched chain thioalkoxy can be 3 to 40, and the number of carbon atoms in a cyclic thioalkoxy can be 3 to 40. Further, the number of carbon atoms in a straight chain thioalkoxy can be preferably 1 to 20, the number of carbon atoms in a branched chain thioalkoxy can be preferentially 3 to 20, and the number of carbon atoms in a cyclic thioalkoxy can be preferentially 3 to 20.

[0141] The present application provides a composition, which includes an organic solvent and at least one organic light-emitting compound as described above. For example, the composition can be used as a coating or printing ink when preparing an organic electronic device.

[0142] In some embodiments, the organic solvent may include at least one selected from aromatics, heteroaromatics, esters, aromatic ketones, aromatic ethers, olefin compounds, and borate compounds. Exemplary, aromatic or heteroaromatic solvents may include, but are not limited to, p-diisopropylbenzene, pentylbenzene, tetralin, cyclohexylbenzene, chlorobenzene, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, o-xylene, p-xylene, phenylacetone, benzophenone, diphenyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, 1,2,3,4-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 2-phenylpyridine, N-methyldiphenylamine, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, 2-methylfuranate, etc.

[0143] An embodiment of the present application provides a mixture, which includes an organic functional material and at least one of the above-mentioned organic light-emitting compounds; or, the mixture includes an organic functional material and at least one of the above-mentioned combinations.

[0144] Among them, the organic functional material may include at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, and a luminescent body host material.

[0145] It is understood that the above mixture can be used as a functional material in the functional layer of an organic electronic device. The functional layer can be, for example, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer and a light emitting layer.

[0146] In one example, the mixture provided in the embodiment of the present application may include the organic light-emitting compound and the hole transport material described above, and the mixture may be applied to the hole transport layer.

[0147] In one example, the mixture provided in the embodiment of the present application may include the organic light-emitting compound and the electron transport material described above, and the mixture may be applied to the electron transport layer.

[0148] The above-mentioned organic functional materials will be further described in the organic electronic devices below and will not be elaborated here.

[0149] The present application also provides an organic electronic device prepared based on the above organic light-emitting compound, composition or mixture. The organic electronic device may be, for example, but not limited to, an organic electroluminescent device, an organic solar cell, an organic field effect transistor, an organic thin film transistor, an organic laser, an organic self-selected electronic device, etc.

[0150] For ease of description and understanding, the following description is made by taking an organic electronic device as an organic electroluminescent device as an example.

[0151] Figure 3 and Figure 4 The organic electronic device 300 is a schematic diagram of a structure of an organic electronic device 300 provided in an embodiment of the present application. It can be understood that the organic electronic device 300 can be Figure 2 An organic electroluminescent device 222 is shown.

[0152] Combination Figure 3 and Figure 4 The organic electronic device 300 may be disposed on a substrate 400, which may be Figure 2 The substrate 221 is shown.

[0153] The organic electronic device 300 may include a first electrode 310 and a second electrode 330 disposed opposite to each other, and at least one functional layer 320 located between the first electrode 310 and the second electrode 330. The first electrode 310 may be located on a substrate 400, and the at least one functional layer 320 may include at least one of the organic light-emitting compounds described above, or at least one of the compositions described above, or at least one of the mixtures described above.

[0154] In some embodiments, the at least one functional layer 320 may include a light-emitting layer 324 , and the light-emitting layer 324 may include the organic light-emitting compound provided in the above-mentioned embodiment of the present application.

[0155] The light emitting layer 324 may be a layer in the organic electronic device 300 for collecting electrons and holes of a certain concentration and providing a site for exciton formation and light emission.

[0156] In some embodiments, the light-emitting layer 324 may include one or more of a light-emitting material, a guest material, and a host material. Optionally, the guest material may include at least one of the organic light-emitting compounds provided in the above embodiments of the present application, or the host material may also include at least one of the organic light-emitting compounds provided in the above embodiments of the present application.

[0157] It should be noted that the first electrode 310 may be an anode, and the second electrode 330 may be a cathode, or the first electrode 310 may be a cathode, and the second electrode 330 may be an anode. For ease of description and understanding, in the embodiment of the present application, the first electrode 310 is an anode, and the second electrode 330 is a cathode.

[0158] It is understood that in the organic electronic device 300, when a bias voltage is applied to the first electrode 310 and the second electrode 330, electrons are injected from the second electrode 330 (cathode) into the light-emitting layer 324 and transferred from the light-emitting layer 324 to the first electrode 310 (anode), or holes are injected from the light-emitting layer to the first electrode 310 (anode). When holes and electrons are combined in the light-emitting layer 324 to form singlet or triplet excitons, light emission is generated.

[0159] In some embodiments, Figure 3 As shown, the at least one functional layer 320 may further include a hole injection layer 321, a hole transport layer 322, an electron blocking layer 323, a hole blocking layer 325, an electron transport layer 326, and an electron injection layer 327 which are stacked in sequence. The hole injection layer 321 may be located on the side of the first electrode 310 facing the second electrode 330, and the electron injection layer 327 may be located on the side of the second electrode 330 facing the first electrode 310. The light emitting layer 324 may be located between the electron blocking layer 323 and the hole blocking layer 325.

[0160] Among them, the hole injection layer 321 can be a layer in the organic electronic device 300 that contacts the anode and promotes holes to enter the light-emitting layer 324 from the anode. This layer can also prevent the excitons generated in the light-emitting layer 324 from moving to the electron injection layer 327. The hole transport layer 322 can be a layer in the organic electronic device 300 that promotes holes from the anode to the charge recombination site, and this layer may not need to contact the anode. The electron blocking layer 323 can be a layer in the organic electronic device 300 that is used to block electrons from the cathode at the interface of the light-emitting layer 324 to increase the electron concentration at the interface of the light-emitting layer 324. The hole blocking layer 325 can be a layer in the organic electronic device 300 that is used to block holes from the anode at the interface of the light-emitting layer 324 to increase the hole concentration at the interface of the light-emitting layer 324. The electron transport layer 326 can be a layer in the organic electronic device 300 that promotes electrons from the cathode to the charge recombination site. This layer may not need to contact the cathode and often may not be an effective hole transporter, so it can be used to block holes from moving to the cathode. The electron injection layer 327 may be a layer that contacts the cathode in the organic electronic device 300 and facilitates electrons to enter the light emitting layer 324 from the cathode.

[0161] Specifically, in some embodiments, at least one of the hole injection layer 321, the hole transport layer 322, the electron blocking layer 323, the hole blocking layer 325, the electron transport layer 326, and the electron injection layer 327 may include at least one organic light-emitting compound provided in the above-mentioned embodiment of the present application. For example, the hole injection layer 321 and the electron blocking layer 323 may include at least one organic light-emitting compound provided in the above-mentioned embodiment of the present application. For another example, the hole transport layer 323 and the electron injection layer 327 may include at least one organic light-emitting compound provided in the above-mentioned embodiment of the present application.

[0162] It should be noted that in the embodiment of the present application, the organic electronic device 300 may not be limited to the above structure. For example, at least one functional layer 320 may only include a light-emitting layer 324, or at least one functional layer 320, in addition to the light-emitting layer 324, may also include at least one of a hole injection layer 321, a hole transport layer 322, an electron blocking layer 323, a hole blocking layer 325, an electron transport layer 326 and an electron injection layer 327.

[0163] For example, in some embodiments, Figure 4 As shown, at least one functional layer 320 may include an electron blocking layer 323 and a light-emitting layer 324 stacked in sequence. The electron blocking layer 323 may be located on the side of the first electrode 310 facing the second electrode 330, and the light-emitting layer 323 may be located on the side of the second electrode 330 facing the first electrode 310. Exemplarily, the electron blocking layer 323 may include at least one organic light-emitting compound provided in the above-mentioned embodiment of the present application.

[0164] In another example, at least one functional layer 320 may include a hole transport layer 322, an electron blocking layer 323, a light emitting layer 324, and an electron transport layer 326, which are stacked in sequence. The hole transport layer 322 may be located on the side of the first electrode 310 facing the second electrode 330, and the electron transport layer 325 may be located on the side of the second electrode 330 facing the first electrode 310. Exemplarily, at least one of the hole transport layer 322, the electron blocking layer 323, and the electron transport layer 326 may include at least one organic light emitting compound provided in the above-mentioned embodiment of the present application.

[0165] It can be understood that the specific structure of the at least one functional layer 320 is merely an example and not a limitation to the present application.

[0166] It should be noted that in the organic electronic device 300 provided in the embodiment of the present application, in addition to at least one functional layer 320 including at least one organic light-emitting compound provided in the embodiment of the present application, the organic electronic device 300 can be manufactured using materials and methods known in the technical field.

[0167] The following is an exemplary method for preparing the organic electronic device 300 .

[0168] In one example, the organic electronic device 300 can be prepared by sequentially stacking a first electrode 310 (anode), at least one functional layer 320, and a second electrode 330 (cathode) on a substrate 400. Specifically, a physical vapor deposition method (such as sputtering or electron beam evaporation) can be used to deposit a metal or a conductive metal oxide or alloy on the substrate 400 to form the first electrode 310 (anode), and then the same method can be used to sequentially deposit a hole injection layer 321, a hole transport layer 322, an electron blocking layer 323, a light emitting layer 324, a hole blocking layer 325, an electron transport layer 326, and an electron injection layer 327 on the first electrode 310, and finally the cathode material is deposited on the electron injection layer 326 to form the second electrode 330 (cathode).

[0169] In another example, the organic electronic device 300 may be prepared by sequentially stacking a second electrode 330 (cathode), at least one functional layer 320 , and a first electrode 330 (anode) on a substrate 400 .

[0170] It can be understood that the above-mentioned method for preparing the organic electronic device 300 is only an example, and the embodiment of the present application can also prepare the organic electronic device 300 by other preparation methods, and the present application does not limit this.

[0171] Next, the materials of each layer structure in the organic electronic device 300 are specifically introduced.

[0172] Materials suitable for the anode may include electrode materials with high power functions, for example, the electrode material may include metals such as vanadium, chromium, copper, zinc, gold or their alloys, or may include metal oxides such as zinc oxide, indium oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide, antimony oxide, zinc indium tin oxide, or may include combinations of metals and oxides such as ZnO:AL or SnO2:Sb; or may include conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene], polypyrrole, polyaniline, etc., and the present application does not limit this. Preferably, ITO is often used as an anode because it is transparent to the propagation of light and thus helps the light emitted by the electroactive organic layer to leave.

[0173] Materials suitable for the cathode may include electrode materials with a small power function, for example, the electrode material may include metals such as lithium, sodium, cesium, magnesium, calcium, strontium, barium, aluminum, silver, gold, indium, tin, zinc, zirconium, scandium, yttrium, or alloys and mixtures thereof. Alloy materials suitable for the cathode may exemplarily include silver-magnesium, aluminum-lithium, indium-magnesium, aluminum-calcium, and aluminum-gold alloys. Layered non-alloy structures may also be used in the cathode, for example, a layer of zero-valent metal (such as aluminum or silver) is covered on a thin layer of calcium or metal fluoride (such as lithium fluoride). Preferably, the cathode may be composed of a single zero-valent metal, such as aluminum metal.

[0174] Materials suitable for the hole injection layer 321 (i.e., hole injection materials) include materials with hole injection properties, the highest occupied molecular orbital of which may be between the work function of the anode material and the highest occupied molecular orbital of the surrounding organic material layer (e.g., the electron blocking layer 323). The materials of the hole injection layer 321 may include, for example, but are not limited to metal porphyrins, oligothiophenes, organic materials based on arylamines, and conductive polymers based on polythiophenes. It is understood that the organic luminescent compound having the first structure provided in the embodiment of the present application may replace or be added to the above-mentioned substances.

[0175] Materials suitable for the hole transport layer 322 (i.e., hole transport materials) may include materials having hole transport properties, such as, but not limited to, compounds containing m-carbazolylphenyl, various triphenylamine trimers and tetramers, etc. It is understood that the organic luminescent compound having the first structure provided in the embodiment of the present application may replace or be added to the above substances.

[0176] Materials suitable for the electron blocking layer 323 may include compounds having an electron blocking effect, such as but not limited to carbazole derivatives, compounds having triphenylmethane silyl and triarylamine structures, monoamine compounds with high electron blocking properties, various triphenylamine dimers, and other compounds having an electron blocking effect. It is understood that the organic light-emitting compound having the first structure provided in the embodiment of the present application may replace or be added to the above substances.

[0177] The light emitting layer 324 may include at least one of a light emitting body, a host material, and a guest material, wherein the triplet energy of the host material may be greater than the triplet energy of the dopant material.

[0178] The host material may include but is not limited to thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, heterocyclic compounds having an indole ring as a partial structure of a condensed ring, etc. It is understood that the organic light-emitting compound having the first structure provided in the embodiment of the present application can be added to the above substances.

[0179] In the embodiment of the present application, the guest material may include an organic luminescent compound having a first structure, wherein the first structure may be a structure formed by bonding a first structural unit represented by the following formula (I) and a second structural unit represented by the following formula (II):

[0180]

[0181] In some embodiments, in addition to the organic light-emitting compound having the first structure, the guest material may also be mixed with other substances, for example, including but not limited to aromatic amine derivatives, styrylamine compounds, metal complexes, etc.

[0182] Materials suitable for the hole blocking layer 325 (i.e., hole blocking materials) may include compounds having hole blocking properties, such as, but not limited to, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi) and other phenanthroline derivatives, metal complexes such as quinolinol derivatives, and various rare earth complexes, oxazole derivatives, triazole derivatives and other compounds having space blocking effects. It is understood that the organic light-emitting compound having the first structure provided in the embodiment of the present application may replace or be added to the above substances.

[0183] Materials suitable for the electron transport layer 326 (i.e., electron transport materials) may include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, etc. It is understood that the organic light-emitting compound having the first structure provided in the embodiment of the present application may replace or be added to the above substances.

[0184] Materials suitable for the electron injection layer 327 (i.e., electron injection materials) may include materials having electron transport properties, such as, but not limited to, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives, etc. It is understood that the organic light-emitting compound having the first structure provided in the embodiment of the present application may replace or be added to the above substances.

[0185] According to the organic electronic device 300 provided in the embodiment of the present application, at least one functional layer 320 in the organic electronic device 300 may include at least one organic light-emitting compound as described above, or include at least one composition having the organic light-emitting compound as described above, or include at least one mixture having the organic light-emitting compound as described above. The organic light-emitting compound has a first structural unit as shown in formula (I) as a skeleton, and the skeleton is modified by introducing a second structural unit as shown in formula (II). This is conducive to obtaining a relatively excellent luminescent performance and realizing blue light, so that it can be efficiently applied to the organic electronic device 300, and the luminescent efficiency and service life of the organic electronic device 300 are improved.

[0186] The embodiment of the present application also provides a display screen, which may include a cover plate, a back plate and the organic electronic device 300 described above. The organic electronic device 300 may be located between the cover plate and the back plate. For a detailed description, please refer to Figure 2 The embodiments shown will not be described in detail here.

[0187] The present application also provides an electronic device, which may include a housing assembly and the above-mentioned display screen, and the display screen may be located inside the housing assembly. Figure 1 The embodiments shown will not be described in detail here.

[0188] The embodiments of the present application are further described in the following embodiments. It should be understood that the advantages of the embodiments of the present application will be partially described in the following description, and part of them will be obvious from the description, or can be learned through the implementation of the embodiments of the present application.

[0189] It should also be understood that the preparation method of the following organic light-emitting compound is only illustrative, and the present application does not limit the specific preparation method of the organic light-emitting compound, as long as the preparation method can protect the organic light-emitting compound provided in the above-mentioned embodiments of the present application.

[0190] [Example 1]

[0191] Synthesis of compound 1:

[0192]

[0193] The reactant 1 (1,3-dibromo-2-chloro-5-fluorobenzene) (100g), 4,4-di-tert-butyldiphenylamine (100g), tris(dibenzylideneacetone)dipalladium (16g), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (20g) and anhydrous sodium tert-butoxide (67g) were dissolved in toluene (500mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 1-1 (126g) with a yield of about 77%.

[0194] Dissolve intermediate 1-1 (100 g), 4H-naphtho[1,2,3,4-def]carbazole (75 g) and anhydrous cesium carbonate (150 g) in anhydrous N,N-dimethylformamide (500 mL). Heat the mixed reaction liquid to 100 ° C and stir at this temperature for 8 hours. After the mixed reaction liquid is cooled to room temperature, add a large amount of deionized water and dichloromethane to extract, and retain the organic phase. Dry the organic phase by vacuum distillation and purify it by silica gel column chromatography to obtain intermediate 1-2 (120 g) with a yield of about 83%.

[0195] Intermediate 1-2 (90 g), 3,6-di-tert-butylcarbazole (44 g), active copper powder (4.2 g), cuprous iodide (12.4 g), anhydrous potassium carbonate (36 g) and 2,2,6,6-tetramethyl-3,5-heptanedione (5 g) were mixed in 1,3-dimethylpropyleneurea (200 mL). The mixed reaction liquid was heated to 150 ° C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 1-3 (90 g) with a yield of about 78%.

[0196] Intermediate 1-3 (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyl lithium (16 mL, n-hexane solution) at a concentration of 1.3 M was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 100 ° C and stirred at this temperature for 2 hours. Subsequently, the mixed reaction solution was cooled to the ice bath temperature and boron tribromide (5.2 mL) was added dropwise. After the addition was completed, the mixed reaction solution was heated to 180 ° C and stirred at this temperature for 8 hours. Subsequently, N, N-diisopropylethylamine (24 mL) was continued to be added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 180 ° C and stirred at this temperature overnight. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 2.4 g of compound 1 with a yield of about 25%.

[0197] The results of MS analysis of compound 1 were MS[M+H] + =881.

[0198] Preparation of an organic electroluminescent device:

[0199] Transparent glass was used as the substrate, and ITO, Ag, and ITO with thicknesses of 15 nm, 150 nm, and 15 nm were sputtered in sequence to form an anode layer. The glass substrate with the anode layer was cleaned with strip liquid, pure water, and isopropanol ultrasonic cleaning in sequence, and then dried and treated with Ar2 ozone. The treated substrate was moved into a vacuum vapor deposition device, and the vacuum in the vacuum vapor deposition device was pumped to 1×10 -6 mPa;

[0200] On the anode layer, PD and HT-1 were mixed and evaporated at a mass ratio of 3:100 by vacuum evaporation to form a hole injection layer with a thickness of 10 nm;

[0201] HT-1 was deposited on the hole injection layer by vacuum evaporation to form a hole transport layer with a thickness of 140 nm;

[0202] HT-2 was deposited on the hole transport layer by vacuum evaporation to form an electron blocking layer with a thickness of 10 nm;

[0203] Compound 1 and BH were mixed and deposited at a mass ratio of 2:98 on the electron blocking layer by vacuum evaporation to form a light-emitting layer with a thickness of 25 nm, wherein compound 1 was used as a guest material and BH was used as a host material;

[0204] ET-1 was deposited on the light-emitting layer by vacuum evaporation to form a hole blocking layer with a thickness of 2 nm;

[0205] On the hole blocking layer, ET-2 and Liq were mixed and evaporated at a mass ratio of 50:50 by vacuum evaporation to form an electron transport layer with a thickness of 35 nm;

[0206] Yb was evaporated on the electron transport layer by vacuum evaporation to form an electron injection layer with a thickness of 1.5 nm;

[0207] Mg and Ag are mixed and evaporated in a mass ratio of 1:9 on the electron injection layer by vacuum evaporation to form a cathode layer with a thickness of 17 nm. Finally, a CPL material layer with a thickness of 55 nm is evaporated on the cathode layer by vacuum evaporation to obtain an organic electroluminescent device.

[0208] The materials involved in the preparation of the organic electroluminescent device are shown in the following structure:

[0209]

[0210] [Example 2]

[0211] Preparation of compound 2:

[0212]

[0213]

[0214] The reactants 2 (1,3-dibromo-2-chloro-5-fluorobenzene) (100 g), 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophene-3-amine (100 g), tri(dibenzylideneacetone)dipalladium (16 g), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (20 g) and anhydrous sodium tert-butoxide (67 g) were dissolved in toluene (500 mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 2-1 (126 g) with a yield of about 77%.

[0215] Dissolve intermediate 2-1 (100 g), 4H-naphtho[1,2,3,4-def]carbazole (75 g) and anhydrous cesium carbonate (150 g) in anhydrous N,N-dimethylformamide (500 mL). Heat the mixed reaction liquid to 100 ° C and stir at this temperature for 8 hours. After the mixed reaction liquid is cooled to room temperature, add a large amount of deionized water and dichloromethane to extract, and retain the organic phase. Dry the organic phase by vacuum distillation and purify it by silica gel column chromatography to obtain intermediate 2-2 (120 g) with a yield of about 83%.

[0216] Intermediate 2-2 (90g), 3,6-di-tert-butylcarbazole (44g), active copper powder (4.2g), cuprous iodide (12.4g), anhydrous potassium carbonate (36g) and 2,2,6,6-tetramethyl-3,5-heptanedione (5g) were mixed in 1,3-dimethylpropyleneurea (200mL). The mixed reaction liquid was heated to 150°C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 2-3 (90g) with a yield of about 78%.

[0217] Intermediate 2-3 (10 g) was dissolved in tert-butylbenzene (300 mL), and tert-butyl lithium (16 mL, n-hexane solution) at a concentration of 1.3 M was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 100 ° C and stirred at this temperature for 2 hours. Subsequently, the mixed reaction solution was cooled to the ice bath temperature and boron tribromide (5.2 mL) was added dropwise. After the addition was completed, the mixed reaction solution was heated to 180 ° C and stirred at this temperature for 8 hours. Subsequently, N, N-diisopropylethylamine (24 mL) was continued to be added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 180 ° C and stirred at this temperature overnight. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water was added and extracted with dichloromethane, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 2.4 g of compound 2 with a yield of about 25%.

[0218] The results of MS analysis of compound 2 were MS[M+H] + =937.

[0219] [Example 3]

[0220] Synthesis of compound 3:

[0221]

[0222] The reactant 3 (1,3-dibromo-2-chloro-5-fluorobenzene) (100g), 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophene-3-amine (100g), tri(dibenzylideneacetone)dipalladium (16g), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (20g) and anhydrous sodium tert-butoxide (67g) were dissolved in toluene (500mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added for extraction, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 3-1 (126g) with a yield of about 77%.

[0223] Intermediate 3-1 (100 g), 4H-naphtho[1,2,3,4-def]carbazole (50 g), active copper powder (6.5 g), cuprous iodide (20 g), anhydrous potassium carbonate (60 g) and 2,2,6,6-tetramethyl-3,5-heptanedione (10 g) were mixed in 1,3-dimethylpropyleneurea (200 mL). The mixed reaction liquid was heated to 150 ° C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 3-2 (110 g) with a yield of about 82%.

[0224] Dissolve intermediate 3-2 (100 g), 3,6-di-tert-butylcarbazole (45 g) and anhydrous cesium carbonate (100 g) in anhydrous N,N-dimethylformamide (500 mL). Heat the mixed reaction solution to 100 ° C and stir at this temperature for 8 hours. After the mixed reaction solution is cooled to room temperature, add a large amount of deionized water and dichloromethane to extract, and retain the organic phase. Dry the organic phase by vacuum distillation and purify it by silica gel column chromatography to obtain intermediate 3-3 (130 g) with a yield of about 94%.

[0225] The intermediate 3-3 (10g) was dissolved in tert-butylbenzene (300mL), and tert-butyl lithium (16mL, n-hexane solution) of 1.3M concentration was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 100°C and stirred at this temperature for 2 hours. Subsequently, the mixed reaction solution was cooled to the ice bath temperature and boron tribromide (5.2mL) was added dropwise. After the addition was completed, the mixed reaction solution was heated to 180°C and stirred at this temperature for 8 hours. Subsequently, N,N-diisopropylethylamine (24mL) was continued to be added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated to 180°C and stirred at this temperature overnight. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water was added and extracted with dichloromethane, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 2.0g of compound 3 with a yield of about 21%.

[0226] The results of MS analysis of compound 2 were MS[M+H] + =881.

[0227] [Example 4]

[0228] Synthesis of compound 4:

[0229]

[0230] The reactant 4 (1,3-dibromo-5-(tert-butyl)benzene) (60g), 4H-naphtho[1,2,3,4-def]carbazole (50g), active copper powder (6.5g), cuprous iodide (20g), anhydrous potassium carbonate (60g) and 2,2,6,6-tetramethyl-3,5-heptanedione (10g) were mixed in 1,3-dimethylpropyleneurea (200mL). The mixed reaction liquid was heated to 150°C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 4-1 (63g) with a yield of about 63%.

[0231] Intermediate 4-1 (70g), 3,6-di-tert-butylcarbazole (44g), active copper powder (4.2g), cuprous iodide (12.4g), anhydrous potassium carbonate (36g) and 2,2,6,6-tetramethyl-3,5-heptanedione (5g) were mixed in 1,3-dimethylpropyleneurea (200mL). The mixed reaction liquid was heated to 150°C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 4-2 (72g) with a yield of about 72%.

[0232] The intermediate 4-2 (10 g) was dissolved in dichlorobenzene (300 mL), and boron tribromide (20 g) was added dropwise under ice bath conditions, and heated to reflux for 12 hours. Subsequently, the mixed reaction solution was cooled to ice bath temperature, and N, N-diisopropylethylamine (120 mL) was added dropwise. After the addition was complete, it was heated to reflux and then stirred for 12 hours. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 2.5 g of compound 4 with a yield of about 26%.

[0233] The results of MS analysis of compound 4 were as follows: MS[M+H] + =658.

[0234] [Example 5]

[0235] Synthesis of compound 5:

[0236]

[0237] The reactant 5 (1,3-dibromo-5-(tert-butyl)benzene) (60g), 4H-naphtho[1,2,3,4-def]carbazole (50g), active copper powder (6.5g), cuprous iodide (20g), anhydrous potassium carbonate (60g) and 2,2,6,6-tetramethyl-3,5-heptanedione (10g) were mixed in 1,3-dimethylpropyleneurea (200mL). The mixed reaction liquid was heated to 150°C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 5-1 (63g) with a yield of about 63%.

[0238] Intermediate 5-1 (50 g), 1-naphthaleneboric acid (20 g) and potassium carbonate (30 g) were mixed in a mixed solution of toluene, ethanol and water, and tetrakis(triphenylphosphine)palladium (3.5 g) was added under a nitrogen atmosphere. The mixed reaction solution was heated to reflux and then stirred overnight. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 5-2 (43 g) with a yield of about 78%.

[0239] The intermediate 5-2 (10 g) was dissolved in dichlorobenzene (300 mL), and boron tribromide (15 g) was added dropwise under ice bath conditions, and heated to reflux for 12 hours. Subsequently, the mixed reaction solution was cooled to ice bath temperature, and N, N-diisopropylethylamine (90 mL) was added dropwise. After the addition was complete, it was heated to reflux and then stirred for 12 hours. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 3.5 g of compound 5 with a yield of about 35%.

[0240] The results of MS analysis of compound 5 were MS[M+H] + =507.

[0241] [Example 6]

[0242] Synthesis of compound 6:

[0243]

[0244]

[0245] The reactant 6 (1,3-dibromo-5-(tert-butyl)benzene) (60g), 4H-naphtho[1,2,3,4-def]carbazole (50g), active copper powder (6.5g), cuprous iodide (20g), anhydrous potassium carbonate (60g) and 2,2,6,6-tetramethyl-3,5-heptanedione (10g) were mixed in 1,3-dimethylpropyleneurea (200mL). The mixed reaction liquid was heated to 150°C and stirred at this temperature for 24 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 6-1 (63g) with a yield of about 63%.

[0246] Intermediate 6-1 (50 g), thiophene boronic acid (20 g) and potassium carbonate (30 g) were mixed in a mixed solution of toluene, ethanol and water, and tetrakis (triphenylphosphine) palladium (3.5 g) was added under a nitrogen atmosphere. The mixed reaction solution was heated to reflux and then stirred overnight. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 6-2 (36 g) with a yield of about 65%.

[0247] The intermediate 6-2 (10 g) was dissolved in dichlorobenzene (300 mL), and boron tribromide (15 g) was added dropwise under ice bath conditions, and heated to reflux for 12 hours. Subsequently, the mixed reaction solution was cooled to ice bath temperature, and N, N-diisopropylethylamine (90 mL) was added dropwise. After the addition was complete, it was heated to reflux and then stirred for 12 hours. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 2.4 g of compound 6 with a yield of about 24%.

[0248] The result of MS analysis of compound 6 was MS [M+H] + =518.

[0249] [Example 7]

[0250] Synthesis of compound 7:

[0251]

[0252] The reactant 7 (1-bromo-4-fluoronaphthalene) (100 g), 3,6-dimethylcarbazole (60 g), and anhydrous cesium carbonate were dissolved in N,N'-dimethylformamide (500 mL). The mixed reaction solution was heated to 120 ° C and stirred at this temperature overnight. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 7-1 (84 g) with a yield of about 72%.

[0253] Dissolve the intermediate 7-1 (50g) in anhydrous tetrahydrofuran (500mL), and add 1.3M concentration of n-butyl lithium (100mL) at -78°C. After the mixed reaction solution is kept warm for 2 hours, add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (25g). After the addition is completed, slowly return to room temperature and monitor the reaction progress by thin plate chromatography. After the reaction is completed, add a large amount of deionized water and dichloromethane to extract, and retain the organic phase. Dry the organic phase by vacuum distillation and purify it by silica gel column chromatography to obtain intermediate 7-2 (46g) with a yield of about 83%.

[0254] Intermediate 7-2 (30 g) and potassium carbonate (20 g) were mixed in a mixed solution of toluene, ethanol and water, and tetrakis (triphenylphosphine) palladium (2.5 g) was added under a nitrogen atmosphere. The mixed reaction solution was heated to reflux and then stirred overnight. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract the organic phase. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain intermediate 7-3 (33 g) with a yield of about 72%.

[0255] The intermediate 7-3 (10 g) was dissolved in dichlorobenzene (300 mL), and boron tribromide (10 g) was added dropwise under ice bath conditions, and heated to reflux for 12 hours. Subsequently, the mixed reaction solution was cooled to ice bath temperature, and N, N-diisopropylethylamine (60 mL) was added dropwise. After the addition was complete, it was heated to reflux and then stirred for 12 hours. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water was added and extracted with dichloromethane, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain 1.1 g of compound 7 with a yield of about 11%.

[0256] The result of MS analysis of compound 7 was MS [M+H] + =705.

[0257] To highlight the beneficial effects of the embodiments of the present application, the following comparative examples are provided.

[0258] [Comparative Example]

[0259] Preparation of comparative compound 1:

[0260]

[0261] The comparative reaction product 1 (tribromobenzene) (50g), 4,4-di-tert-butyldiphenylamine (180g), tri(dibenzylideneacetone)dipalladium (24g), tri-tert-butylphosphine tetrafluoroborate (30g) and anhydrous sodium tert-butoxide (100g) were dissolved in toluene (800mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain the intermediate comparative intermediate 1 (140g) with a yield of about 95%.

[0262] The comparative intermediate 1 (10 g) was dissolved in o-dichlorobenzene (250 mL), and boron tribromide (8.2 g) was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated and stirred to reflux. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain comparative compound 1 (2 g) with a yield of about 22%.

[0263] Preparation of an organic electroluminescent device:

[0264] In Comparative Example 1, an organic electroluminescent device was prepared in the same manner as in Example 1, except that in this comparative example, comparative compound 1 and BH were mixed and evaporated in a mass ratio of 2:98 to form a light-emitting layer with a thickness of 25 nm.

[0265] [Comparative Example 2]

[0266] Synthesis of comparative compound 2:

[0267]

[0268] The comparative reaction product 2 (tribromobenzene) (50g), 4,4-di-tert-butyldiphenylamine (120g), tri(dibenzylideneacetone) dipalladium (16g), tri-tert-butylphosphine tetrafluoroborate (20g) and anhydrous sodium tert-butoxide (67g) were dissolved in toluene (500mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain the comparative intermediate 2-1 (100g) with a yield of about 87%.

[0269] The comparative intermediate 2-1 (100 g), 3,6-di-tert-butylcarbazole (50 g), cuprous iodide (5.5 g), anhydrous potassium carbonate (40 g) and 1,10-o-phenanthroline (5.5 g) were dissolved in anhydrous N,N-dimethylformamide (500 mL). The mixed reaction solution was heated to reflux and stirred for 24 hours. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain the comparative intermediate 2-2 (83 g) with a yield of about 67%.

[0270] The comparative intermediate 2-2 (10 g) was dissolved in o-dichlorobenzene (250 mL), and boron tribromide (8.2 g) was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated and stirred to reflux. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain comparative compound 2 (3.4 g) with a yield of about 35%.

[0271] [Comparative Example 3]

[0272] Synthesis of comparative compound 3:

[0273]

[0274] The comparative reactant 3 (tribromobenzene) (100g), 4,4-di-tert-butyldiphenylamine (120g), tri(dibenzylideneacetone)dipalladium (16g), tri-tert-butylphosphine tetrafluoroborate (20g) and anhydrous sodium tert-butoxide (67g) were dissolved in toluene (500mL). The mixed reaction liquid was heated to 90°C and stirred at this temperature for 2 hours. After the mixed reaction liquid was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain the comparative intermediate 3-1 (122g) with a yield of about 75%.

[0275] The comparative intermediate 3-1 (60g), 3,6-di-tert-butylcarbazole (100g), cuprous iodide (11g), anhydrous potassium carbonate (80g) and 1,10-o-phenanthroline (11g) were dissolved in anhydrous N,N-dimethylformamide (500mL). The mixed reaction solution was heated to reflux and stirred for 24 hours. After the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain the comparative intermediate 3-2 (70g) with a yield of about 65%.

[0276] The comparative intermediate 3-2 (10 g) was dissolved in o-dichlorobenzene (250 mL), and boron tribromide (8.2 g) was added dropwise under ice bath conditions. After the addition was completed, the mixed reaction solution was heated and stirred to reflux. After the reaction was completed, the mixed reaction solution was cooled to room temperature, a large amount of deionized water and dichloromethane were added to extract, and the organic phase was retained. The organic phase was dried by vacuum distillation and purified by silica gel column chromatography to obtain comparative compound 2 (3.5 g) with a yield of about 36%.

[0277] Furthermore, in order to strongly support the beneficial effects brought about by the technical solutions of the embodiments of the present application, a comparison of the optical properties of the organic light-emitting compounds prepared in Examples 1-7 of the present application and Comparative Examples 1-3 is provided, and the results are shown in Table 1.

[0278] In addition, the organic electroluminescent devices prepared in Example 1 and Comparative Example 1 were used as experimental objects, and the obtained organic electroluminescent devices were subjected to power-on tests. The obtained data results are shown in Table 2.

[0279] Table 1 Comparison of the performance of organic light-emitting compounds in Examples 1-5 and Comparative Examples 1-3

[0280] Luminescence peak(nm) Full width at half maximum FWHM (nm) Photoluminescence quantum yield PLQY (%) Example 1 461 22 90 Example 2 471 23 96 Example 3 456 19 93 Example 4 478 23 86 Example 5 498 24 98 Example 6 521 39 95 Example 7 489 33 58 Comparative Example 1 453 28 80 Comparative Example 2 465 30 81 Comparative Example 3 478 28 78

[0281] Table 2 Performance comparison of organic electroluminescent devices in Example 1 and Comparative Example 1

[0282]

[0283] In Table 2, the working life of the organic electroluminescent device at a brightness of 1000 may refer to the working time when the brightness loss of the organic electroluminescent device reaches 5% when the organic electroluminescent device works at a brightness of 1000.

[0284] It can be seen from the data in Table 1 that, compared with Comparative Examples 1-3, the organic light-emitting compounds in Examples 1-5 provided in the present application all exhibit narrower FWHM and higher PLQY, and the emission peaks of the organic light-emitting compounds in Examples 1-7 are all within the blue light wavelength range. This indicates that in the organic light-emitting compounds provided in the present application, by introducing the second structural unit to modify the first structural unit as the structural skeleton, the organic light-emitting compound can have a relatively excellent light-emitting performance and is conducive to the realization of blue light.

[0285] Further combined with the data in Table 2, compared with Comparative Example 1, the organic light-emitting compound in Example 1 provided in the embodiments of the present application exhibits higher luminous efficiency and narrower FWHM in the organic electroluminescent device, and compared with Comparative Example 1, the organic electroluminescent device using the organic light-emitting compound in Example 1 exhibits a longer working life at a brightness of 1000. This further shows that the organic light-emitting compound provided in the embodiments of the present application has excellent luminescent properties, can be efficiently applied to organic electronic devices, and improves the luminous efficiency and working life of organic electronic devices.

[0286] The above is only a specific implementation of the present application, but the protection scope of the present application is not limited thereto. Any person skilled in the art who is familiar with the present technical field can easily think of changes or substitutions within the technical scope disclosed in the present application, which should be included in the protection scope of the present application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

1. An organic light-emitting compound, characterized in that: The organic light-emitting compound has a first structure, wherein the first structure is a structure formed by bonding a first structural unit represented by formula (I) and a second structural unit represented by formula (II); Wherein, in the formula (I) and the formula (II), Ring A, Ring B, and Ring K are each independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; V is selected from boron atom, nitrogen atom, phosphorus atom, aluminum atom, >CR 1 -, >P(=O)-; Each U and W are independently selected from -C(R 1 ,R 2 )-、-NR 1 -、-P(=O)R 1 Any one of -; Each X, each Y and each Z are independently selected from nitrogen atoms, or >CR 1 -; Among them, each R 1 and R 2 Each is independently selected from any one of a hydrogen atom, a deuterium atom, a halogen atom, a silyl group, a keto group, a cyano group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a formyl group, a carbamoyl group, a haloformyl group, a carbonyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, and a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms.

2. The organic light-emitting compound according to claim 1, characterized in that: The first structural unit includes a skeleton and a ring structure connected to the skeleton, and the second structural unit is bonded to the ring structure via a connecting bond.

3. The organic light-emitting compound according to claim 1, characterized in that: The first structural unit includes a skeleton and a ring structure connected to the skeleton, and the second structural unit bonds to the first structural unit by replacing a part of the ring structure.

4. The organic light-emitting compound according to any one of claims 1 to 3, characterized in that: The general formula of the first structure is as follows: a )~Formula (i c ) as shown in any of the following:

5. The organic light-emitting compound according to claim 4, characterized in that: The organic light-emitting compound includes the formula (i a )~the formula (i c ) at least one of the first structures shown.

6. The organic light-emitting compound according to any one of claims 1 to 5, characterized in that The V is selected from a boron atom, and each U is independently selected from -NR 1 -.

7. A composition, characterized in that The method comprises an organic solvent and at least one organic light-emitting compound according to any one of claims 1 to 6.

8. A mixture, characterized in that The mixture comprises an organic functional material and at least one organic light-emitting compound according to any one of claims 1 to 6; or, The mixture comprises the organic functional material and at least one composition according to claim 7; The organic functional material includes at least one of a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminophore and a host material.

9. An organic electronic device, characterized in that: include: a first electrode and a second electrode disposed opposite to each other, and at least one functional layer located between the first electrode and the second electrode; The at least one functional layer comprises at least one organic light-emitting compound according to any one of claims 1 to 6, or comprises at least one composition according to claim 7, or comprises at least one mixture according to claim 8.

10. The organic electronic device according to claim 9, characterized in that: The organic electronic device is an organic electroluminescent device, the at least one functional layer comprises a light-emitting layer, and the light-emitting layer comprises at least one organic light-emitting compound.

11. The organic electronic device according to claim 10, characterized in that: The at least one functional layer further comprises at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer stacked in sequence, and the light-emitting layer is located between the electron blocking layer and the hole blocking layer. At least one of the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer, and the electron transport layer includes at least one of the organic light emitting compounds.

12. A display screen, characterized in that: The invention comprises a cover plate, a back plate and the organic electronic device according to any one of claims 9 to 12, wherein the organic electronic device is located between the back plate and the cover plate.

13. An electronic device, characterized in that: It comprises a housing assembly and a display screen as claimed in claim 13, wherein the display screen is located inside the housing assembly.

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