CN114560879B - Fluorescent compound, mixture and light-emitting device - Google Patents

Fluorescent compound, mixture and light-emitting device Download PDF

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CN114560879B
CN114560879B CN202210199520.4A CN202210199520A CN114560879B CN 114560879 B CN114560879 B CN 114560879B CN 202210199520 A CN202210199520 A CN 202210199520A CN 114560879 B CN114560879 B CN 114560879B
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CN114560879A (en
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相烨鹏
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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Abstract

Disclosed are a fluorescent compound, a mixture, and a light emitting device. The fluorescent compound is a boron-nitrogen narrow-luminescence pure organic thermal activation delayed fluorescent material, and molecules of the fluorescent compound have the dual characteristics of chiral luminescence and dominant dipole moment orientation, so that the surface plasmon mode in a luminescent device can be effectively reduced, and the device efficiency is further improved.

Description

Fluorescent compound, mixture and light-emitting device
Technical Field
The application relates to the technical field of display, in particular to a fluorescent compound, a mixture and a light-emitting device.
Background
Organic light-emitting diodes (OLEDs) have the advantages of no need of backlight source for active light emission, high light emitting efficiency, large visual angle, high response speed, large temperature application range, relatively simple production and processing technology, low driving voltage, small energy consumption, lighter and thinner flexible display and the like, and huge application prospects, attract the attention of numerous researchers, and are commercially produced on a large scale and applied to various display products. However, in addition to the further improvement in luminous efficiency, a large pain spot that plagues OLED products is the problem of "burn-in" caused by aging. Surface plasmon modes (SPPs) in the vicinity of the electrodes of OLED devices are generally considered to be a loss because exciton energy is dissipated in the form of heat by non-radiative surface plasmon modes. Efficiency and stability improvements have been an important advance in OLED technology.
Therefore, it is desirable to provide a fluorescent compound that can effectively reduce the surface plasmon modes within the device to improve the device efficiency.
Disclosure of Invention
The application aims to provide a fluorescent compound which can effectively reduce surface plasmon modes in a device and can avoid the phenomenon of ageing of the device caused by heat loss.
The embodiment of the application provides a fluorescent compound, which has a structure shown in a general formula (I):
wherein X is 1 、X 2 Are independently selected from N-R 1 、CR 2 R 3 、O、S、SiR 4 R 5 Any one of them; r is R 1 -R 5 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group;
A 1 、A 2 are respectively and independently selected from N, CR 6 、SiR 7 、GeR 8 、PR 9 R 10 Any one of them; r is R 6 -R 10 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group;
y contains chiral groups selected from any one of substituted or unsubstituted alkyl groups containing 1 to 30 carbon atoms, substituted or unsubstituted aryl groups containing 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups containing 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups containing 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane groups containing 1 to 30 carbon atoms, substituted or unsubstituted arylsilane groups containing 6 to 50 carbon atoms, cyano groups, nitro groups and halogen groups;
z is selected from any one of B or p=o.
Optionally, in some embodiments of the application, Y is selected from one of the following structures:
wherein is the site of attachment.
Optionally, in some embodiments of the application, the fluorescent compound is selected from one of the following structures:
alternatively, in some embodiments of the application, R 11 And R is 12 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group.
Alternatively, in some embodiments of the application, R 11 And R is 12 Is a different group.
Alternatively, in some embodiments of the application, X 1 、X 2 Each independently selected from one of the following structures:
wherein is the site of attachment.
Alternatively, in some embodiments of the application, A 1 、A 2 Each independently selected from one of the following structures:
wherein is the site of attachment.
Optionally, in some embodiments of the application, the fluorescent compound is selected from at least one of the following structures:
accordingly, embodiments of the present application also provide a mixture comprising at least one fluorescent compound as described above, and at least one other organic functional material.
Optionally, in some embodiments of the present application, the organic functional material is selected from at least one of a luminescent material, a host material, and an organic dye.
Alternatively, in some embodiments of the present application, the functional material is primarily used for carrier transport and energy transfer.
Correspondingly, the embodiment of the application also provides a light-emitting device, which comprises a substrate base plate, and an anode, a functional layer and a cathode which are arranged on the substrate base plate; wherein the functional layer comprises a light emitting layer comprising a fluorescent compound as described above.
Optionally, in some embodiments of the application, the functional layer is disposed between the anode and the cathode, and the functional layer further comprises:
a hole function layer disposed between the anode and the light emitting layer; and/or
And an electron functional layer disposed between the cathode and the light emitting layer.
Optionally, in some embodiments of the application, the hole-functional layer includes a hole-injecting layer and/or a hole-transporting layer. The electron functional layer includes an electron injection layer and/or an electron transport layer.
In addition, the embodiment of the application also provides a display device which comprises the light-emitting device.
The application has the beneficial effects that:
the fluorescent compound is a boron-nitrogen narrow-luminescence pure organic thermal activation delayed fluorescent material, and molecules of the fluorescent compound have the dual characteristics of chiral luminescence and dominant dipole moment orientation, so that the surface plasmon mode in a luminescent device can be effectively reduced, and the device efficiency is further improved.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural view of a light emitting device according to an embodiment of the present application;
fig. 2 is a schematic diagram of a second structure of a light emitting device according to an embodiment of the present application;
FIG. 3 is a circular dichromatic absorption curve of the compound of example 1 of the present application.
Detailed Description
The following description of the embodiments of the present application will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to fall within the scope of the application. In addition, in the description of the present application, the term "comprising" means "including but not limited to". The terms first, second, third and the like are used merely as labels, and do not impose numerical requirements or on the order of construction. Various embodiments of the application may exist in a range of forms; it should be understood that the description in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the application; it is therefore to be understood that the range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, a description of a range from 1 to 6 should be considered to have specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as single numbers within the range, such as 1, 2, 3, 4,5, and 6, as applicable regardless of the range. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
In the course of research and practice of the prior art, the inventors of the present application have found that surface plasmon modes (SPPs) in the vicinity of the electrodes of OLED devices are generally considered to be a loss, as exciton energy is dissipated thermally by non-radiative surface plasmon modes, and should be avoided as much as possible. But if the light is s polarized light, the surface plasmon mode in the OLED can be effectively reduced, and the efficiency is improved. s-polarized light can be obtained by chiral luminescent molecules or luminescent molecules with dominant transition dipole moments. Meanwhile, the device with chiral luminescence property can be effectively combined with a product without a light filter (Pol-less), and has wider application prospect.
Aiming at the problems, the application adopts the boron-nitrogen narrow-luminescence pure organic Thermal Activation Delayed Fluorescence (TADF) material, and the molecule has the dual characteristics of chiral luminescence and dominant dipole moment orientation through ingenious molecular design, so that the SPP mode in the device is effectively reduced, and the device efficiency is improved.
The embodiment of the application provides a fluorescent compound, a mixture and a light-emitting device. The following will describe in detail. The following description of the embodiments is not intended to limit the preferred embodiments.
In the present application, "substituted" means that a hydrogen atom in a substituent is replaced with a substituent.
In the present application, the same substituent may be independently selected from different groups when it appears multiple times. Containing a plurality of R as shown in the general formula 1 R is then 1 May be independently selected from different groups.
In the present application, "substituted or unsubstituted" means that the defined group may or may not be substituted.
In a preferred embodiment, the aryl group is selected from: benzene, naphthalene, anthracene, fluoranthene, phenanthrene, benzophenanthrene, perylene, naphthacene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; heteroaryl is selected from the group consisting of triazines, pyridines, pyrimidines, imidazoles, furans, thiophenes, benzofurans, benzothiophenes, indoles, carbazoles, pyrroloimidazoles, pyrrolopyrroles, thienopyrroles, thienothiophenes, furopyrroles, furofurans, thienofurans, benzisoxazoles, benzisothiazoles, benzimidazoles, quinolines, isoquinolines, phthalazines, quinoxalines, phenanthridines, primary pyridines, quinazolines, quinazolinones, dibenzofurans, dibenzothiophenes, carbazoles, and derivatives thereof.
In the present application, "×" indicates a ligation site.
In the present application, when no attachment site is specified in a group, an optionally attachable site in the group is represented as an attachment site.
In the present application, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.gR in (C) is connected with any substitutable site of benzene ring.
In the present application, adjacent groups may be cyclic to each other means that adjacent groups combine to form a substituted or unsubstituted aliphatic ring system, a substituted or unsubstituted aromatic ring system, a substituted or unsubstituted aliphatic heterocyclic system, or a substituted or unsubstituted heteroaromatic ring system; the ring system may be monocyclic or polycyclic.
The embodiment of the application provides a fluorescent compound, which has a structure shown in a general formula (I):
further, X 1 、X 2 Are independently selected from N-R 1 、CR 2 R 3 、O、S、SiR 4 R 5 Any one of the following.
For example, the fluorescent compound is selected from, but not limited to, one of the following structures:
further, R 1 -R 5 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group.
Further, A 1 、A 2 Are respectively and independently selected from N, CR 6 、SiR 7 、GeR 8 、PR 9 R 10 Any one of the following.
Further, R 6 -R 10 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group.
Further, Y is selected from any one of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a cyano group, a nitro group, and a halogen group. Further, Y contains a chiral group.
Further, Z is selected from any one of B or p=o.
For example, the fluorescent compound may be selected from one of the following structures:
in some embodiments of the application, Y is selected from one of the following structures:
wherein is the site of attachment.
Further, the fluorescent compound is selected from, but not limited to, one of the following structures:
further, R 11 And R is 12 Each independently selected from any one of hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted alkylsilane group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilane group having 6 to 50 carbon atoms, cyano group, nitro group, halogen group. Further, R 11 And R is 12 Is a different group.
In some embodiments of the application, X 1 、X 2 Each independently selected from one of the following structures:
wherein is the site of attachment.
Alternatively, in some embodiments of the application, A 1 、A 2 Respectively and independently selectFrom one of the following structures:
wherein is the site of attachment.
In some embodiments, the fluorescent compound is selected from, but is not limited to, one of the following structures:
/>
aiming at a surface plasmon (SPP) excimer mode in a device, the application adopts a boron-nitrogen narrow-luminescence pure organic Thermal Activation Delayed Fluorescence (TADF) material, and the molecule has the dual characteristics of chiral luminescence and dominant dipole moment orientation through ingenious molecular design, so that the SPP mode in the device is effectively reduced, and the device efficiency is improved.
The fluorescent compound provided by the application is a material with a narrow spectrum and an advantageous orientation and chiral structure.
Embodiments of the present application also provide a mixture comprising at least one fluorescent compound as described above, and at least one other organic functional material. Further, the organic functional material is selected from at least one of a light emitting material, a host material, and an organic dye.
The embodiment of the application also provides a light-emitting device, which comprises a substrate base plate, and an anode, a functional layer and a cathode which are arranged on the substrate base plate; wherein the functional layer comprises a light emitting layer. And, the light emitting layer includes a fluorescent compound as shown in formula (I). The structure of the fluorescent compound is shown with reference to the foregoing.
In some embodiments, the light emitting layer comprises: at least one fluorescent compound of the application and Host A, the structure of which is
Further, in the light emitting layer, the mass percentage of the fluorescent compound may be 1wt%, 2wt%, or 3wt%. For example, the mass ratio of the fluorescent compound to Host a is 4:196; the light-emitting layer may employ a fluorescent compound with Host a at 4:196 mass ratio was obtained by evaporation.
In some embodiments of the application, the functional layer is disposed between the anode and the cathode, and the functional layer further comprises:
a hole function layer disposed between the anode and the light emitting layer; and/or
And an electron functional layer disposed between the cathode and the light emitting layer.
Referring to fig. 1, the light emitting device 100 includes an anode 110, a hole function layer 120, a light emitting layer 130, an electron function layer 140, and a cathode 150 sequentially disposed on a substrate 101. Further, the hole function layer 120 includes a hole injection layer 121 and/or a hole transport layer 122. The electron functional layer 140 includes an electron injection layer 142 and/or an electron transport layer 141.
Referring to fig. 2, the light emitting device 100 may further include a cathode 150, an electron functional layer 140, a light emitting layer 130, a hole functional layer 120, and an anode 110 sequentially disposed on the substrate 101. Further, the hole function layer 120 includes a hole injection layer 121 and/or a hole transport layer 122. The electron functional layer 140 includes an electron injection layer 142 and/or an electron transport layer 141.
The light emitting devices of the embodiments of the present application may be fabricated according to methods known in the art, such as those disclosed in the references (adv. Mater.2003,15,277). The specific method comprises the following steps: and (3) sequentially evaporating the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode on the cleaned conductive glass (ITO) substrate under the high vacuum condition.
The embodiment of the application also provides a display device which comprises any one of the light emitting devices.
The application has been tested several times in succession, and the application will now be described in further detail with reference to a few test results, which are described in detail below in connection with specific examples.
Example 1
This example provides a fluorescent compound (compound 1), the synthetic route of which compound 1 comprises:
1) Synthesis of intermediate 1-a:
to a 250mL reaction flask were added 1, 3-dibromo-2, 5-dichlorobenzene (15.2 g,50 mmol), phenoxazine (19.20 g,105 mmol), tris (dibenzylideneacetone) dipalladium (920 mg,1 mmol), bis (2-diphenylphosphinophenyl) ether (1.1 g,2 mmol) and sodium t-butoxide (10.1 g,105 mmol), followed by three pump-throughs, 100mL of anhydrous toluene was purged under an argon atmosphere, and then reacted at 80℃for 24 hours. After the reaction is cooled to room temperature, the reaction solution is poured into 200mL of saturated saline water, and is filtered by suction and then separated and purified by column chromatography to obtain an intermediate 1-a (19.05 g, yield is 75%);
2) Synthesis of intermediate raw material 1:
to a 500mL reaction flask was added intermediate 1-a (19.05 g,37.5 mmol) and 200mL of t-butylbenzene, n-butyllithium (69.5 mL,111.2 mmol) was added dropwise at-78deg.C, followed by stirring at 60deg.C for 2 hours, and then the low boiling point solvent was distilled off under reduced pressure. Boron tribromide (27.9 g,111.2 mmol) was added dropwise at-78℃and stirred for 1 hour, and N, N diisopropylethylamine (14.6 g,111.2 mmol) was added dropwise at 0℃and stirred for 2 hours at 120 ℃. Cooling to room temperature, adding sodium acetate aqueous solution, stirring, extracting with ethyl acetate to obtain base layer, concentrating, separating and purifying by column chromatography to obtain raw material 1 (6.53 g, yield 20%); MS (EI) M/z: [ M ]] + 482.10；
3) Synthesis of target compound 1:
to a 250mL two-port flask were added raw material 1 (2.63 g,5 mmol),(s) -5- (sec-butyl) -1H-pyrrol-2 (5H) -one (284 mg,6 mmol), palladium acetate (45 mg,0.2 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17 g,0.6 mmol), and then NaOt-Bu (0.58 g,6 mmol) was added to the glove box, 100mL of toluene dehydrated and deoxygenated beforehand was injected under argon atmosphere, and reacted at 120℃for 24 hours. Cooling to room temperature, pouring the reaction solution into 200mL ice water, extracting with dichloromethane three times, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: n-hexane, v: v, 1:5) to obtain light green powder 1.3g, and the yield is 44%. MS (EI) M/z: [ M ] +:585.22.
The circular dichromatic absorption curve of compound 1 in this example is shown in FIG. 3. As can be seen from fig. 3, compound 1 in this example has a chiral group.
Example 2
This example provides a fluorescent compound (compound 2), the synthetic route of which compound 2 comprises:
to a 250mL two-necked flask were added raw material 1 (2.41 g,5 mmol),(s) -2- (9-isopropyl-7, 9-dimethyl-9H-fluoren-2-yl) -4, 5-tetramethyl-1, 3, 2-dioxaborane (1.10 g,6 mmol), tetrakis (triphenylphosphine) palladium (58 mg,0.05 mmol) and potassium carbonate (2.76 g,20 mmol), and 80mL of previously deoxygenated tetrahydrofuran and 40mL of previously deoxygenated water were injected under an argon atmosphere to react at 90℃for 24 hours. Cooling to room temperature, pouring the reaction solution into 200mL ice water, extracting with dichloromethane three times, combining organic phases, spinning into silica gel, separating and purifying by column chromatography (dichloromethane: n-hexane, v: v, 1:3) to obtain green powder 1.2g, and yield 36%. MS (EI) M/z: [ M ] +:682.31. Raw material 1 of this example was prepared by referring to the synthesis procedure in example 1.
Example 3
This example provides a fluorescent compound (compound 3), the synthetic route of which compound 3 comprises:
to a 250mL two-necked flask were added raw material 1 (2.41 g,5 mmol),(s) -4 ([ 2.2] p-cycloalkyl) -4, 5-tetramethyl-1, 3, 2-dioxaborane (2.0 g,6 mmol), tetrakis (triphenylphosphine) palladium (58 mg,0.05 mmol) and potassium carbonate (2.76 g,20 mmol), and 80mL of previously deoxygenated tetrahydrofuran and 40mL of previously deoxygenated water were injected under argon atmosphere to react at 90℃for 24 hours. Cooling to room temperature, pouring the reaction solution into 200mL of ice water, extracting with dichloromethane three times, combining organic phases, spinning into silica gel, and separating and purifying by column chromatography (dichloromethane: n-hexane, v: v, 1:3) to obtain 1.6g of light yellow powder with the yield of 49%. MS (EI) M/z: [ M ] +:654.24.
Comparative example 1
This example provides a compound having the structure shown below:
experimental example 1 theoretical simulation calculation of target molecule:
the fluorescent compounds obtained in examples 1 to 3 of the present application were each investigated in this test example. The electrochemical energy levels of the fluorescent compounds are shown in table 1 below.
TABLE 1
Device example 1
The present embodiment provides a light emitting device including: glass and conductive glass (ITO) substrate layers (i.e., substrate substrates with anodes); hole injection layer HATCN:10nm; hole transport layer NPB:100nm; light-emitting layer 20nm (light-emitting layer material comprising compound 1 and Host a of example 1, and evaporated to give light-emitting layer at a ratio of 4:196); the electron transport layer is 30nm, and TPBI and LiQ are adopted for vapor deposition according to the proportion of 1:1; the electron injection layer is 1nm, and the material is LiQ; the cathode is 100nm, and the material is Al.
The preparation method of the light-emitting device of the embodiment may be: and (3) sequentially evaporating the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode on the cleaned conductive glass (ITO) substrate under the high vacuum condition.
The partial material structure in this embodiment is as follows:
device example 2
The present embodiment provides a light emitting device including: glass and conductive glass (ITO) substrate layers (i.e., substrate substrates with anodes); hole injection layer HATCN:10nm; hole transport layer NPB:100nm; light-emitting layer 20nm (light-emitting layer material comprises compound 2 and Host in example 2, and evaporation is performed according to the ratio of 4:196 to obtain a light-emitting layer); the electron transport layer is 30nm, and TPBI and LiQ are adopted for vapor deposition according to the proportion of 1:1; the electron injection layer is 1nm, and the material is LiQ; the cathode is 100nm, and the material is Al.
The preparation method of the light-emitting device of the embodiment may be: and (3) sequentially evaporating the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode on the cleaned conductive glass (ITO) substrate under the high vacuum condition.
Device example 3
The present embodiment provides a light emitting device including: glass and conductive glass (ITO) substrate layers (i.e., substrate substrates with anodes); hole injection layer HATCN:10nm; hole transport layer NPB:100nm; light-emitting layer 20nm (light-emitting layer material comprising compound 3 and Host in example 3, and evaporated to give light-emitting layer at a ratio of 4:196); the electron transport layer is 30nm, and TPBI and LiQ are adopted for vapor deposition according to the proportion of 1:1; the electron injection layer is 1nm, and the material is LiQ; the cathode is 100nm, and the material is Al.
The preparation method of the light-emitting device of the embodiment may be: and (3) sequentially evaporating the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode on the cleaned conductive glass (ITO) substrate under the high vacuum condition.
Device comparative example 1
The present embodiment provides a light emitting device including: glass and conductive glass (ITO) substrate layers (i.e., substrate substrates with anodes); hole injection layer HATCN:10nm; hole transport layer NPB:100nm; light-emitting layer 20nm (light-emitting layer material comprising compound BD-1 and Host a of comparative example 1, and vapor deposited at a ratio of 4:196 to give a light-emitting layer); the electron transport layer is 30nm, and TPBI and LiQ are adopted for vapor deposition according to the proportion of 1:1; the electron injection layer is 1nm, and the material is LiQ; the cathode is 100nm, and the material is Al.
The preparation method of the light-emitting device of the embodiment may be: and (3) sequentially evaporating the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the electron injection layer and the cathode on the cleaned conductive glass (ITO) substrate under the high vacuum condition.
The partial material structure in this embodiment is as follows:
test example 2
This test example performs light emission performance detection for the light emitting devices in device examples 1 to 3, respectively. The method comprises the following steps: at a current density of 10mA/cm 2 The luminescence characteristics of the prepared device were recorded under the conditions. The performance data of the devices are shown in Table 2.
TABLE 2
Device and method for manufacturing the same Light-emitting layer Voltage (V) Electroluminescent peak (nm) EQE(％) LT95(hr)
Device example 1 Compound 1 3.75 462 6.8 82
Device example 2 Compound 2 3.88 482 8.5 67
Device example 3 Compound 3 3.77 478 7.2 75
Device comparative example 1 BD-1 3.81 462 4.1 80
As can be seen from table 2, the efficiency of the device example of the present application can reach 8.5%, while the efficiency of the device comparative example is only 4.1%, and the efficiency of the device using the fluorescent compound of the present application is significantly higher than that of the device comparative example, so that the fluorescent compound of the present application can improve the light-emitting efficiency of the light-emitting material, and the beneficial effects are significant.
In summary, the fluorescent compound of the application realizes the synthesis of a narrow luminescent TADF material with the dual characteristics of chiral luminescence and dominant dipole moment orientation and the application thereof in luminescent devices. According to the application, through collocation of different chiral functional groups and narrow-luminescence TADF groups, a luminescent material with both chirality and dominant transition dipole moment orientation is designed. The application improves the synthesis efficiency of materials and realizes the preparation of high-efficiency organic electroluminescent devices through reasonable route design. Display devices and electronic devices based on the fluorescent compound may be manufactured. The fluorescent compound can be applied to high-efficiency luminescent materials, long-service-life OLED electroluminescent devices and display based on the electroluminescent devices.
In the foregoing embodiments, the descriptions of the embodiments are emphasized, and for parts of one embodiment that are not described in detail, reference may be made to related descriptions of other embodiments.
The above description of the present application provides a fluorescent compound, a mixture and a light-emitting device, and specific examples are applied to illustrate the principles and embodiments of the present application, and the above examples are only for helping to understand the method and core ideas of the present application; meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present application, the present description should not be construed as limiting the present application.

Claims (3)

1. A fluorescent compound, characterized in that the fluorescent compound is selected from the following structures:
。
2. a light emitting device comprising a substrate, and an anode, a functional layer, and a cathode disposed on the substrate; wherein the functional layer comprises a light-emitting layer comprising the fluorescent compound according to claim 1.
3. The light-emitting device according to claim 2, wherein the functional layer is provided between the anode and the cathode, and wherein the functional layer further comprises:
a hole function layer disposed between the anode and the light emitting layer; and/or
And an electron functional layer disposed between the cathode and the light emitting layer.
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Citations (4)

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Publication number Priority date Publication date Assignee Title
CN113072925A (en) * 2020-01-03 2021-07-06 罗门哈斯电子材料韩国有限公司 Organic electroluminescent materials and organic electroluminescent device comprising the same
CN113540369A (en) * 2020-04-13 2021-10-22 罗门哈斯电子材料韩国有限公司 Organic electroluminescent device
CN113788851A (en) * 2021-08-09 2021-12-14 深圳大学 Halogenated polycyclic aromatic compound containing boron atom and preparation method thereof
CN113999256A (en) * 2021-11-26 2022-02-01 中国科学技术大学 Boron-containing organic compound and light-emitting device

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113072925A (en) * 2020-01-03 2021-07-06 罗门哈斯电子材料韩国有限公司 Organic electroluminescent materials and organic electroluminescent device comprising the same
CN113540369A (en) * 2020-04-13 2021-10-22 罗门哈斯电子材料韩国有限公司 Organic electroluminescent device
CN113788851A (en) * 2021-08-09 2021-12-14 深圳大学 Halogenated polycyclic aromatic compound containing boron atom and preparation method thereof
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