CN113831315B - Organic luminescent material and preparation method and application thereof - Google Patents

Organic luminescent material and preparation method and application thereof Download PDF

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CN113831315B
CN113831315B CN202111432358.8A CN202111432358A CN113831315B CN 113831315 B CN113831315 B CN 113831315B CN 202111432358 A CN202111432358 A CN 202111432358A CN 113831315 B CN113831315 B CN 113831315B
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CN113831315A (en
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宋小贤
李成龙
王悦
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Ji Hua Laboratory
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Abstract

The invention relates to the technical field of organic photoelectric materials and devices, and discloses an organic luminescent material, a preparation method and application thereof, wherein the molecular structural formula of the organic luminescent material is any one of the following formulas (I) - (III):
Figure DEST_PATH_IMAGE001
a compound of the formula (I),
Figure 867410DEST_PATH_IMAGE002
a compound of the formula (II),
Figure DEST_PATH_IMAGE003
formula (III). According to the invention, the excellent optical property and the structural characteristic of easy modification of coumarin are combined, and the cyano-substituted benzocoumarin is used as an acceptor group to construct a novel long-wavelength TADF material.

Description

Organic luminescent material and preparation method and application thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials and devices, and mainly relates to an organic luminescent material, and a preparation method and application thereof.
Background
Organic light-emitting diodes (OLEDs) have made great progress over thirty years and have been widely used in small and medium-sized display products such as smart phones, wearable devices, and vehicle displays. Throughout the OLED industry chain, organic light emitting materials have always played a crucial role, being one of the highest technical barriers. However, the core patent and market share of high performance luminescent materials are mostly monopolized by foreign companies such as UDC, japan, Merck, germany, and the like, which severely restricts the healthy development of new display industries in our country, and it is imperative to develop new luminescent materials with independent intellectual property rights and promote the localization thereof.
According to the constraint of quantum mechanical transition law of electron spin conservation, the traditional fluorescent dye can only utilize 25% of energy of singlet excitons, and the limit of internal quantum efficiency is 25%. The second generation organic luminescent material is a phosphorescent material containing noble metals such as iridium and platinum, and the spin-orbit coupling effect induced by heavy metals such as iridium and platinum enables triplet excitons to return to a ground state directly through a radiation transition process to emit phosphorescence, and the theoretical internal quantum efficiency can reach 100%. However, the noble metals (such as iridium and platinum) in the metal complex phosphorescent material are scarce, the material cost is high, the realization of lower-cost OLED application is not facilitated, and most phosphorescent devices have a larger efficiency roll-off problem at high brightness because the material has a long triplet state life. Therefore, the development of a new generation of organic electroluminescent materials with low cost, high light-emitting efficiency and high exciton utilization rate is imminent.
In recent years, a Thermally Activated Delayed Fluorescence (TADF) material has received much attention because it combines features of 100% exciton utilization efficiency, low cost, and environmental friendliness. TADF is considered as a third generation organic electroluminescent material following phosphorescent materials, and has a wide application prospect in the field of future OLEDs. In recent years, TADF materials emitting light with wavelengths of blue light, green light, and the like have been developed rapidly, but long-wavelength light-emitting materials have a rapidly decreasing non-radiative transition rate with an increase in emission wavelength due to the limitation of the energy gap rule, and thus high-efficiency, low-roll-off TADF materials for red light and deep red light are still very rare. This limits the application of highly efficient TADF materials for full color displays and white light illumination.
Studies have shown that coumarin luminescent dyes have excellent photophysical and photochemical properties, but their emission wavelength is usually in the short-wavelength region, which limits their application range in the field of luminescence. Therefore, the coumarin has important application value in carrying out structural modification on the coumarin and developing coumarin luminescent materials emitting in a long wavelength region.
Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention aims to provide an organic light emitting material, a preparation method and an application thereof, wherein the organic light emitting material is a derivative of coumarin, and aims to provide a novel derivative of coumarin, and solve the problems of scarcity and low efficiency of the existing long-wavelength TADF material.
The technical scheme of the invention is as follows:
an organic light-emitting material, wherein the molecular structural formula of the organic light-emitting material is any one of the following formulas (I) - (III):
Figure 770291DEST_PATH_IMAGE001
a compound of the formula (I),
Figure 501486DEST_PATH_IMAGE002
a compound of the formula (II),
Figure 291588DEST_PATH_IMAGE003
formula (III);
m is independently an integer of 1 to 5;
r is an electron donating group, the electron donating group being substituted with one or more R1Substituted heteroaryl of C5 to C30, or substituted with one or more R1Substituted C6-C30 arylamine;
R1is hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, C1-C18 alkyl, C1-C18 alkoxy, C3-C10 cycloalkyl, substituted by one or more R2Substituted C6-C14 aryl, substituted by one or more R2Substituted heteroaryl of C5 to C30, or substituted with one or more R2A substituted aromatic amine group;
R2is hydrogen, fluorine, chlorine, C1-C18 alkyl, C1-C18 alkoxy, substituted by one or more R3Substituted C6-C14 aryl, substituted by one or more R3Substituted heteroaryl of C5 to C30, or substituted with one or more R3A substituted aromatic amine group;
R3is methyl, tert-butyl, methoxy or carbazolyl.
The organic light-emitting material is a derivative of coumarin, combines the excellent optical property and the structural characteristic of easy modification of the coumarin, and utilizes cyano-substituted benzocoumarin as a receptor group to construct a novel long-wavelength TADF material.
The organic light-emitting material, wherein R is selected from any one of the following groups:
Figure 609699DEST_PATH_IMAGE004
Figure 268082DEST_PATH_IMAGE005
Figure 417566DEST_PATH_IMAGE006
Figure 503203DEST_PATH_IMAGE007
Figure 43031DEST_PATH_IMAGE008
。
the compound constructed by connecting the electron donating group with the cyano coumarin nucleus has a twisted configuration, a donor acceptor has a larger twisted angle, the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of a molecule can be effectively separated, and the singlet-triplet energy level difference of the compound is reduced, so that the compound has TADF (TADF) properties.
The organic light-emitting material is characterized in that the molecular structural formula of the organic light-emitting material is any one of formulas 1-129:
Figure 177209DEST_PATH_IMAGE009
Figure 712358DEST_PATH_IMAGE010
Figure 906579DEST_PATH_IMAGE011
Figure 228976DEST_PATH_IMAGE012
Figure 617711DEST_PATH_IMAGE013
Figure 37060DEST_PATH_IMAGE014
Figure 293860DEST_PATH_IMAGE015
Figure 870597DEST_PATH_IMAGE016
Figure 815420DEST_PATH_IMAGE017
Figure 230220DEST_PATH_IMAGE018
Figure 533288DEST_PATH_IMAGE019
Figure 767960DEST_PATH_IMAGE020
Figure 47632DEST_PATH_IMAGE021
Figure 411879DEST_PATH_IMAGE022
Figure 587646DEST_PATH_IMAGE023
Figure 371931DEST_PATH_IMAGE024
Figure 894442DEST_PATH_IMAGE025
Figure 814993DEST_PATH_IMAGE026
Figure 161661DEST_PATH_IMAGE027
。
a method for preparing the organic light emitting material, comprising the following steps:
adding the first raw material, R-group substituted benzaldehyde and malononitrile into ethanol, adding triethylamine, heating to 75-85 ℃ in a nitrogen atmosphere, refluxing for 6-8 hours, and stopping heating after the reaction is finished;
the reaction system is automatically cooled to room temperature to precipitate solid, the solid is filtered, a filter cake is washed by ethanol, and a first solid is obtained after drying in an oven;
adding the obtained first solid and iodine into ethanol, heating to 75-85 ℃, refluxing for 10-14 h, and stopping heating after the reaction is finished;
the reaction system is automatically cooled to room temperature to precipitate solid, the solid is filtered, the filter cake is washed by ethanol, and the filter cake is dried by an oven;
wherein the first raw material is 1-naphthol, 2-naphthol or 9-phenanthrol.
The preparation method of the organic luminescent material comprises the following steps of (1) enabling the molar ratio of the first raw material to the R-group-substituted benzaldehyde and the malononitrile to be 1.1-1.3: 1: 1.1-1.3;
adding the first raw material, R-group-substituted benzaldehyde and malononitrile into ethanol, and adding triethylamine, wherein in the step of adding triethylamine, 20-30 mL of ethanol is added into each millimole of the first raw material, and 2-3 drops of triethylamine are added into each millimole of the first raw material.
The preparation method of the organic luminescent material comprises the following steps of (1) preparing a first solid, wherein the molar ratio of the first solid to iodine is 1: 1.1-1.3;
in the step of adding the obtained first solid and iodine into ethanol, 30-50 mL of ethanol is added per millimole of iodine.
The preparation method of the organic luminescent material is characterized in that the molecular structural formula of the benzaldehyde substituted by the R group is selected from any one of the following formulas b1-b 43:
Figure 997024DEST_PATH_IMAGE028
Figure 979017DEST_PATH_IMAGE029
Figure 285234DEST_PATH_IMAGE030
Figure 26970DEST_PATH_IMAGE031
Figure 989110DEST_PATH_IMAGE032
Figure 211012DEST_PATH_IMAGE033
。
use of an organic light emitting material as claimed in any preceding claim, wherein the organic light emitting material is used in the manufacture of an organic electroluminescent device.
The organic electroluminescent device is composed of a cathode, an organic compound layer and an anode from top to bottom in sequence; the organic compound layer at least comprises a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer; the light-emitting layer contains the organic light-emitting material.
The organic light-emitting material is applied, wherein the light-emitting layer comprises a main material and a doping material, and the doping material is the organic light-emitting material.
Has the advantages that: the organic luminescent material provided by the invention combines the excellent optical property and the structural characteristic of easy modification of coumarin, utilizes cyano-substituted benzocoumarin as a receptor group to construct a novel long-wavelength TADF material, has a simple and feasible preparation method, and can be applied to an organic electroluminescent device.
Drawings
FIG. 1 is a graph showing absorption and emission spectra of Compound 1 in example 1 of the present invention.
FIG. 2 shows the absorption and emission spectra of Compound 3 of example 1 of the present invention.
FIG. 3 is a graph showing absorption and emission spectra of Compound 5 in example 1 of the present invention.
FIG. 4 is a graph showing absorption and emission spectra of Compound 11 in example 1 of the present invention.
Fig. 5 is a schematic structural view of an organic electroluminescent device in embodiment 2 of the present invention.
Detailed Description
The invention provides an organic luminescent material, a preparation method and an application thereof, and the invention is further described in detail below in order to make the purpose, technical scheme and effect of the invention clearer and more clear. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The following disclosure provides many different embodiments or examples for implementing different features of the invention. To simplify the disclosure of the present invention, the components and arrangements of specific examples are described below. Of course, they are merely examples and are not intended to limit the present invention. Furthermore, the present invention may repeat reference numerals and/or letters in the various examples, such repetition is for the purpose of simplicity and clarity and does not in itself dictate a relationship between the various embodiments and/or configurations discussed. In addition, the present invention provides examples of various specific processes and materials, but one of ordinary skill in the art may recognize applications of other processes and/or uses of other materials.
The invention provides an organic luminescent material, which is a derivative of coumarin, and the molecular structural formula of the organic luminescent material is any one of the following formulas (I) - (III):
Figure 607621DEST_PATH_IMAGE001
a compound of the formula (I),
Figure 296091DEST_PATH_IMAGE002
a compound of the formula (II),
Figure 43730DEST_PATH_IMAGE003
formula (III).
Wherein m is independently an integer of 1 to 5;
r is an electron donating group which may be one or more R1Substituted heteroaryl of C5 to C30, or substituted with one or more R1Substituted C6-C30 arylamine;
R1can be hydrogen, deuterium, fluorine, chlorine, bromine, iodine, cyano, C1-C18 alkyl, C1-C18 alkoxy, C3-C10 cycloalkyl, substituted by one or more R2Substituted C6-C14 aryl, substituted by one or more R2Substituted heteroaryl of C5 to C30, or substituted with one or more R2A substituted aromatic amine group;
R2can be hydrogen, fluorine, chlorine, C1-C18 alkyl, C1-C18 alkoxy, substituted by one or more R3Substituted C6-C14 aryl, substituted by one or more R3Substituted heteroaryl of C5 to C30, or substituted with one or more R3A substituted aromatic amine group;
R3can be methyl, tert-butyl, methoxy or carbazolyl.
In particular, said R may be selected from the following groups:
Figure 210269DEST_PATH_IMAGE004
Figure 225498DEST_PATH_IMAGE005
Figure 914231DEST_PATH_IMAGE006
Figure 945903DEST_PATH_IMAGE034
Figure 181712DEST_PATH_IMAGE008
。
the compound constructed by connecting the electron donating group with the cyano coumarin nucleus has a twisted configuration, a donor acceptor has a larger twisted angle, the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of a molecule can be effectively separated, and the singlet-triplet energy level difference of the compound is reduced, so that the compound has TADF (TADF) properties.
The acceptor group of the organic luminescent material has the following 3 characteristics: (1) is benzocoumarin, (2) is cyano-substituted benzocoumarin, and (3) is connected with an electron-donating group through a phenyl group. The benzocoumarin expands the conjugated area of the coumarin, and a large planar pi-conjugated receptor structure is beneficial to long-wavelength luminescence; cyano is a typical electron-withdrawing substituent, the electron-withdrawing capability of an acceptor is enhanced by introducing the cyano, the property of the compound D-A is more obvious, and the luminescence wavelength can be further red-shifted.
Most of the developed coumarin stays in the research on the basic photophysical properties of compounds, and is mainly in a short-wavelength region, the luminescent wavelength of the derivative of the coumarin is red-shifted compared with that of the traditional coumarin, and the derivative can be applied to organic electroluminescent devices.
In the scheme of the preferred embodiment of the invention, the molecular structural formula of the organic light-emitting material can be any one of formulas 1-129. Wherein the compounds with the numbers 1-34, 103-111 belong to the compounds of the formula (I), the compounds with the numbers 35-68, 112-120 belong to the compounds of the formula (II), and the compounds with the numbers 69-102, 121-129 belong to the compounds of the formula (III):
Figure 51448DEST_PATH_IMAGE035
Figure 645503DEST_PATH_IMAGE036
Figure 335110DEST_PATH_IMAGE037
Figure 407233DEST_PATH_IMAGE038
Figure 334738DEST_PATH_IMAGE039
Figure 535912DEST_PATH_IMAGE040
Figure 745439DEST_PATH_IMAGE041
Figure 588630DEST_PATH_IMAGE042
Figure 636221DEST_PATH_IMAGE043
Figure 8296DEST_PATH_IMAGE044
Figure 185679DEST_PATH_IMAGE045
Figure 301403DEST_PATH_IMAGE046
Figure 734658DEST_PATH_IMAGE047
Figure 575837DEST_PATH_IMAGE048
Figure 930595DEST_PATH_IMAGE049
Figure 850010DEST_PATH_IMAGE050
Figure 809876DEST_PATH_IMAGE051
。
the invention also provides a preparation method of the organic luminescent material, which comprises the following steps:
adding the first raw material, benzaldehyde and malononitrile substituted by R groups into ethanol according to a molar ratio of 1.1-1.3: 1: 1.1-1.3, adding a few drops of triethylamine, heating to 75-85 ℃ in a nitrogen atmosphere, refluxing for 6-8 hours, and stopping heating after the reaction is finished; adding 20-30 mL of ethanol into each millimole of the first raw material, and adding 2-3 drops of triethylamine into each millimole of the first raw material;
the reaction system is automatically cooled to room temperature to precipitate solid, the solid is filtered, the filter cake is washed by ethanol, and the solid is obtained after drying in an oven; wherein the drying temperature can be 85-100 ℃;
adding the obtained first solid and iodine into ethanol according to the molar ratio of 1: 1.1-1.3, heating to 75-85 ℃, refluxing for 10-14 h, and stopping heating after the reaction is finished; wherein, 30-50 mL of ethanol is added into each millimole of iodine;
and (3) automatically cooling the reaction system to room temperature to separate out a second solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain a solid product.
Wherein, the first raw material can be 1-naphthol, 2-naphthol or 9-phenanthrol.
When the first raw material is 1-naphthol, the prepared organic luminescent material is shown in the formula (I), and the reaction is shown in the formula (IV):
Figure 821956DEST_PATH_IMAGE052
formula (IV).
When the first raw material is 2-naphthol, the prepared organic luminescent material is shown in the formula (II), and the reaction is shown in the formula (V):
Figure 929590DEST_PATH_IMAGE053
formula (V).
When the first raw material is 9-phenanthrol, the organic luminescent material shown in the formula (III) is prepared, and the reaction is shown in the formula (VI):
Figure 387116DEST_PATH_IMAGE054
formula (VI).
The invention also provides application of the organic light-emitting material, and the organic light-emitting material is used for preparing an organic electroluminescent device (OLED).
Further, the organic electroluminescent device is composed of a cathode, an organic compound layer and an anode from top to bottom in sequence; the organic compound layer at least comprises a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer; the light-emitting layer contains the organic light-emitting material. Further, the organic light emitting material serves as a dopant material together with the host material as a light emitting layer.
In the organic electroluminescent device, the transparent anode may be formed by using an electrode material known per se, that is, by vapor-depositing an electrode material having a large work function, such as ITO or gold, on a substrate (a transparent substrate, such as a glass substrate). Materials for the device of the present invention may be those known in the art for organic electroluminescent devices.
The organic electroluminescent device can be used for preparing organic electroluminescent displays, organic electroluminescent lighting sources, decorative light sources and the like.
The present invention is further illustrated by the following specific examples.
The starting materials used in the following examples are not particularly limited in their origin, and may be commercially available products or prepared by methods known to those skilled in the art.
In the following examples, the room temperature is 10-30 ℃.
Example 1: synthesis of Compounds
Compound 1 synthesis example:
1-naphthol (793 mg, 5.5 mmol), 4-diphenylaminobenzaldehyde (1367 mg, 5 mmol) and malononitrile (363 mg, 5.5 mmol) were added to 150 mL of ethanol, 5 drops of triethylamine were added, and the mixture was heated under reflux for 6 hours under a nitrogen atmosphere. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain the solid for the next reaction. The resulting solid (931 mg, 2 mmol) and iodine (558 mg, 2.2 mmol) were added to 100 mL of an ethanol solution and the reaction was heated under reflux for 12 h. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain a final solid product.
Compound 37 synthesis example:
2-Naphthol (793 mg, 5.5 mmol), 4- (9H-carbazol-9-yl) benzaldehyde (1357 mg, 5 mmol), and malononitrile (363 mg, 5.5 mmol) were added to 150 mL of ethanol, 5 drops of triethylamine were added, and the mixture was refluxed under nitrogen for 8 hours. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain the solid for the next reaction. The resulting solid (927 mg, 2 mmol) and iodine (558 mg, 2.2 mmol) were added to 100 mL of ethanol solution and heated under reflux for 12 h. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain a final solid product.
Compound 73 synthesis example:
9-Phenols (1069 mg, 5.5 mmol), 4- (10H-phenoxazin-10-yl) benzaldehydes (1437 mg, 5 mmol) and malononitrile (363 mg, 5.5 mmol) were added to ethanol, 5 drops of triethylamine were added, and the mixture was heated under reflux for 6 hours under a nitrogen atmosphere. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain the solid for the next reaction. The resulting solid (959 mg, 2 mmol) and iodine (558 mg, 2.2 mmol) were added to 100 mL of ethanol solution and the reaction was heated under reflux for 12 h. And after the reaction is finished, stopping heating, automatically cooling the reaction system to room temperature to precipitate a solid, filtering, washing a filter cake with ethanol, and drying in an oven to obtain a final solid product.
According to the synthetic route, the product compounds 1-129 are respectively obtained through carbon-carbon coupling and carbon-nitrogen coupling reactions, and the product data are summarized as shown in tables 1-4. R group-substituted benzaldehydes required for the preparation of compounds 1-129 are shown below as formulas b1-b 43.
Figure 499690DEST_PATH_IMAGE055
Figure 650049DEST_PATH_IMAGE056
Figure 713820DEST_PATH_IMAGE057
Figure 240616DEST_PATH_IMAGE058
Figure 942118DEST_PATH_IMAGE059
Figure 263378DEST_PATH_IMAGE060
Figure 80025DEST_PATH_IMAGE061
。
TABLE 1
Figure 879353DEST_PATH_IMAGE062
TABLE 2
Figure 966520DEST_PATH_IMAGE063
TABLE 3
Figure 458681DEST_PATH_IMAGE064
TABLE 4
Figure 497045DEST_PATH_IMAGE065
Wherein, the absorption and emission spectra of the prepared compounds 1, 3, 5 and 11 are respectively shown in figures 1-4. Wherein Abs in ToL is the absorption spectrum of the compound in toluene solution, PL in Tol is the emission spectrum of the compound in toluene solution, and PL of Solid is the emission spectrum of the compound Solid. Fig. 1 to 4 are representations of basic photophysical properties of the luminescent compound, and it can be seen from fig. 1 to 4 that the luminescent wavelength of the compound solid is in the yellow and red regions.
Example 2: preparation of organic electroluminescent device
The compound 5 and the compound 11 prepared in the example 1 are used for preparing an organic electroluminescent device, and the specific device preparation process and the device performance test experiment operation are as follows:
the transparent ITO glass is used as a transparent substrate for preparing a device, the transparent ITO glass is subjected to ultrasonic treatment for 30 min by using a washing solution, then ultrasonic washing is sequentially carried out by using distilled water (2 times), acetone (2 times) and isopropanol (2 times), and finally the ITO glass is stored in the isopropanol. Before each use, the surface of the ITO glass is carefully wiped by using an acetone cotton ball and an isopropanol cotton ball, and after the ITO glass is washed by isopropanol and dried, the ITO glass is treated by plasma for 5 min. Preparation of device by vacuum evaporation process using vacuum coating equipmentCompleting the vacuum evaporation system when the vacuum degree reaches 5 x 10-4And starting evaporation when the pressure is lower than Pa, monitoring the deposition rate by a Saynes film thickness instrument, and sequentially depositing various organic layers, a LiF electron injection layer and an Al metal cathode on the ITO glass by utilizing a vacuum evaporation process. The specific device structure is shown in fig. 5, and comprises an ITO glass 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, an electron transport layer 5, an electron injection layer 6, and a metal cathode 7 in sequence from bottom to top.
In this embodiment, ITO glass is used as a transparent substrate, NPB is used as a hole transport layer, TCTA is used as an electron blocking layer, a light emitting layer (EML) uses CBP as a host, 5 wt% of compound 5 or compound 11 as an object, TPBI is used as an electron transport layer, LiF is used as an electron injection layer, and Al is used as a metal cathode; the structure of the organic electroluminescent device is [ ITO/NPB (335nm)/TCTA (5nm)/EML (25nm)/TPBI (40 nm)/LiF (1 nm)/Al (100 nm) ], and EML represents a light-emitting layer. A device 1 was prepared using compound 5 as the light-emitting layer guest material, a device 2 was prepared using compound 11 as the light-emitting layer guest material, a device 3 was prepared using compound 39 as the light-emitting layer guest material, a device 4 was prepared using compound 45 as the light-emitting layer guest material, a device 5 was prepared using compound 73 as the light-emitting layer guest material, and a device 6 was prepared using compound 79 as the light-emitting layer guest material.
Wherein the molecular structural formula of NPB is
Figure 100064DEST_PATH_IMAGE066
The molecular structural formula of TCTA is
Figure 104055DEST_PATH_IMAGE067
The molecular structural formula of CBP is
Figure 501538DEST_PATH_IMAGE068
TPBI has a molecular structural formula of
Figure 292776DEST_PATH_IMAGE069
。
The characteristics of the device such as current, voltage, brightness, light-emitting spectrum and the like are synchronously tested by a PR655 spectral scanning luminance meter and a Keithley K2400 digital source meter system. After the device is packaged, the basic performance indexes of the OLED device are represented by a conventional method, including the starting voltage, the light-emitting peak position, the light-emitting maximum brightness and the device efficiency (%), and the results are shown in Table 5.
TABLE 5
Figure 168329DEST_PATH_IMAGE070
According to the existing experimental data, the electron donating group in the organic luminescent material is preferably two R1Substituted heteroaryl of C12-C25 or substituted heteroaryl with two R1Substituted C12-C25 aromatic amine radical, R1The organic light-emitting material can be methyl, tert-butyl or phenyl, and the efficiency of a device prepared by the organic light-emitting material can reach more than 13%.
In conclusion, the novel long-wavelength TADF material is constructed by using cyano-substituted benzocoumarin as an acceptor group in combination with the excellent optical property and the structural characteristic of easy modification of coumarin. The above embodiments show that the coumarin derivative can be synthesized by a simple and feasible synthesis scheme, and can be applied to organic electroluminescent devices, so as to solve the technical problems of scarcity and low efficiency of long-wavelength TADF materials in the prior art.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.

Claims (10)

1. An organic light-emitting material is characterized in that the molecular structural formula of the organic light-emitting material is any one of the following formulas (I) - (III):
Figure 699551DEST_PATH_IMAGE001
a compound of the formula (I),
Figure 413429DEST_PATH_IMAGE002
a compound of the formula (II),
Figure 239171DEST_PATH_IMAGE003
formula (III);
m is independently an integer of 1 to 5;
r is an electron donating group, the electron donating group being substituted with one or more R1Substituted heteroaryl of C5 to C30, or substituted with one or more R1Substituted C6-C30 arylamine;
R1is hydrogen, deuterium, chlorine, bromine, iodine, C1-C18 alkyl, C1-C18 alkoxy, C3-C10 cycloalkyl, substituted by one or more R2Substituted C6-C14 aryl, substituted by one or more R2Substituted heteroaryl of C5 to C30, or substituted with one or more R2A substituted aromatic amine group;
R2is hydrogen, chlorine, C1-C18 alkyl, C1-C18 alkoxy, substituted by one or more R3Substituted C6-C14 aryl, substituted by one or more R3Substituted heteroaryl of C5 to C30, or substituted with one or more R3A substituted aromatic amine group;
R3is methyl, tert-butyl, methoxy or carbazolyl.
2. The organic light-emitting material according to claim 1, wherein R is selected from any one of the following groups:
Figure 165539DEST_PATH_IMAGE004
Figure 776649DEST_PATH_IMAGE005
Figure 146582DEST_PATH_IMAGE006
Figure 210352DEST_PATH_IMAGE007
Figure 205990DEST_PATH_IMAGE008
。
3. the organic light-emitting material of claim 1, wherein the molecular structural formula of the organic light-emitting material is any one of formulas 1 to 129:
Figure 917945DEST_PATH_IMAGE009
Figure 708046DEST_PATH_IMAGE010
Figure 9846DEST_PATH_IMAGE011
Figure 543595DEST_PATH_IMAGE012
Figure 863718DEST_PATH_IMAGE013
Figure 605147DEST_PATH_IMAGE014
Figure 643510DEST_PATH_IMAGE015
Figure 466104DEST_PATH_IMAGE016
Figure 906312DEST_PATH_IMAGE017
Figure 772637DEST_PATH_IMAGE018
Figure 816073DEST_PATH_IMAGE019
Figure 426046DEST_PATH_IMAGE020
Figure 720761DEST_PATH_IMAGE021
Figure 39878DEST_PATH_IMAGE022
Figure 787254DEST_PATH_IMAGE023
Figure 466497DEST_PATH_IMAGE024
。
4. a method for preparing the organic light-emitting material according to any one of claims 1 to 3, comprising the steps of:
adding the first raw material, R-group substituted benzaldehyde and malononitrile into ethanol, adding triethylamine, heating to 75-85 ℃ in a nitrogen atmosphere, refluxing for 6-8 hours, and stopping heating after the reaction is finished;
the reaction system is automatically cooled to room temperature to precipitate solid, the solid is filtered, a filter cake is washed by ethanol, and a first solid is obtained after drying in an oven;
adding the obtained first solid and iodine into ethanol, heating to 75-85 ℃, refluxing for 10-14 h, and stopping heating after the reaction is finished;
the reaction system is automatically cooled to room temperature to precipitate solid, the solid is filtered, the filter cake is washed by ethanol, and the filter cake is dried by an oven;
wherein the first raw material is 1-naphthol, 2-naphthol or 9-phenanthrol.
5. The method for preparing an organic light-emitting material according to claim 4, wherein the molar ratio of the first raw material to the R group-substituted benzaldehyde to the malononitrile is 1.1 to 1.3: 1: 1.1 to 1.3;
adding the first raw material, R-group-substituted benzaldehyde and malononitrile into ethanol, and adding triethylamine, wherein in the step of adding triethylamine, 20-30 mL of ethanol is added into each millimole of the first raw material, and 2-3 drops of triethylamine are added into each millimole of the first raw material.
6. The method for preparing an organic light-emitting material according to claim 4, wherein the molar ratio of the first solid to the iodine is 1: 1.1 to 1.3;
in the step of adding the obtained first solid and iodine into ethanol, 30-50 mL of ethanol is added per millimole of iodine.
7. The method for preparing an organic light-emitting material according to claim 4, wherein the molecular structural formula of the R group-substituted benzaldehyde is selected from any one of the following formulas b1-b 43:
Figure 864986DEST_PATH_IMAGE025
Figure 869851DEST_PATH_IMAGE026
Figure 855256DEST_PATH_IMAGE027
Figure 72611DEST_PATH_IMAGE028
Figure 341918DEST_PATH_IMAGE029
Figure 521881DEST_PATH_IMAGE030
。
8. use of the organic light emitting material according to any one of claims 1 to 3 for the preparation of an organic electroluminescent device.
9. The use of the organic light-emitting material according to claim 8, wherein the organic electroluminescent device comprises, from top to bottom, a cathode, an organic compound layer, and an anode; the organic compound layer at least comprises a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer; the light-emitting layer contains the organic light-emitting material.
10. The use of the organic light-emitting material according to claim 9, wherein the light-emitting layer comprises a host material and a dopant material, and the dopant material is the organic light-emitting material.
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