CN109943320B - Thermal activation delayed fluorescent material, preparation method thereof and organic light-emitting device - Google Patents
Thermal activation delayed fluorescent material, preparation method thereof and organic light-emitting device Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 63
- 230000003111 delayed effect Effects 0.000 title claims abstract description 42
- 238000007725 thermal activation Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000126 substance Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 14
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- 229910052760 oxygen Inorganic materials 0.000 claims description 6
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- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical group C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 abstract description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 5
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002238 attenuated effect Effects 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 11
- -1 diphenylamine compound Chemical class 0.000 description 9
- 229940125782 compound 2 Drugs 0.000 description 7
- 229940126214 compound 3 Drugs 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 239000005457 ice water Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical group C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- HWTHOPMRUCFPBX-UHFFFAOYSA-N 9,9-diphenyl-10h-acridine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
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- 229960002796 polystyrene sulfonate Drugs 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The chemical structural formula of the thermal activation delayed fluorescent material is shown as
The R group is a diphenylamine group. By taking tetraphenyl ethylene as a core and connecting groups such as carbazole, phenoxazine and the like, the high-efficiency deep blue photo-thermal activation delayed fluorescent material is constructed, so that the external quantum efficiency of an organic electroluminescent device prepared based on the material is improved, the efficiency is slowly attenuated, and the service life of the organic electroluminescent device is further prolonged.
Description
Technical Field
The invention relates to the technical field of display, in particular to a thermal activation delayed fluorescent material, a preparation method thereof and an organic light-emitting device.
Background
An OLED (Organic Light-Emitting Diode) has a great application value in the fields of illumination, display and the like and is widely applied. The photoelectric conversion efficiency is one of important parameters for evaluating the performance of the OLED, and various fluorescent and phosphorescent light-emitting materials have been developed to improve the light-emitting efficiency of the OLED.
The OLED based on the fluorescent material has the characteristic of high stability, but is limited by the quantum statistics law, under the action of electric activation, the proportion of generated singlet excited state excitons and triplet excited state excitons is 1:3, so that the internal electroluminescence quantum efficiency of the fluorescent material is limited to 25%; the phosphorescent material has a spin-orbit coupling effect of heavy atoms, can simultaneously utilize singlet excited state excitons and triplet excited state excitons, and has an electron luminescence quantum efficiency of 100% in theory, but the phosphorescence-based OLED material mostly adopts noble metals, so that the cost is high, and the phosphorescence-based OLED material is not environment-friendly.
In order to overcome the disadvantages of these two materials, experts propose to utilize triplet excited excitons to return to singlet state by thermal activation and then radiatively transition back to ground state to emit light, so that the theoretical internal quantum efficiency reaches 100%. This allows the use of organic compounds which do not contain heavy metal atoms to achieve high efficiencies which are compatible with phosphorescent OLEDs. In recent years, although TADF (Thermally Activated Delayed Fluorescence) materials have been reported, the types of highly efficient and stable red, green and blue TADF materials are few, the selectivity of the materials is still insufficient, the efficiency of most materials in OLED devices is rapidly reduced, and the stability of the devices is still to be improved.
Disclosure of Invention
The invention provides a thermal activation delayed fluorescent material, which can solve the problems that the existing thermal activation delayed fluorescent material is lack of types, the efficiency attenuation in an OLED device is high, the stability of the device is not high, and the performance of the OLED device is further influenced.
In order to solve the above problems, the technical scheme provided by the invention is as follows:
the invention provides a thermal activation delayed fluorescent material, which has a chemical structural formula shown as a general formula (A):
In one embodiment of the present invention, the R group is selected from one of carbazole group and phenoxazine group.
In one embodiment of the invention, the R group is selected from one of the following groups:
the invention also provides a preparation method of the thermal activation delayed fluorescent material, wherein the chemical structural formula of the thermal activation delayed fluorescent material is shown as the general formula (A):
s10, mixing a first reactant, a second reactant and a catalyst in a container to obtain a first mixture, wherein the second reactant is a diphenylamine compound, and the chemical structural formula of the first reactant is shown as a general formula (D):
s20, placing the container in a vacuum glove box, and adding an alkaline compound and a solvent into the container in the glove box to obtain a second mixture;
s30, carrying out heat treatment on the container filled with the second mixture to obtain a reaction solution;
s40, cooling and extracting the reaction liquid to obtain an organic mixture;
s50, removing impurities from the organic mixture to obtain the thermally activated delayed fluorescence material.
In one embodiment of the present invention, the second reactant is selected from one of the following structural formulas:
in an embodiment of the invention, in S30, the temperature of the heat treatment is 110 degrees celsius, and the time of the heat treatment is 24 hours.
In one embodiment of the invention, the basic compound is sodium tert-butoxide and the solvent is toluene stripped of water oxygen.
In an embodiment of the present invention, the S40 includes:
s401, cooling the reaction liquid to room temperature, and pouring the reaction liquid into ice water;
s402, extracting for three times by using dichloromethane, combining organic phases, and spinning into silica gel to obtain the organic mixture.
In an embodiment of the present invention, the S50 includes:
s501, separating the organic mixture by using a column chromatography method to obtain light blue powder;
s502, purifying the light blue powder by using a sublimator to obtain the thermal activation delayed fluorescent material.
The invention also provides an organic light-emitting device which comprises a substrate, and an anode, a light-emitting layer and a cathode which are sequentially arranged on the substrate, wherein the light-emitting layer comprises the thermal activation delayed fluorescence material prepared by the preparation method.
The invention has the beneficial effects that: according to the invention, the tetraphenyl ethylene is used as the core and is connected with the carbazole, the phenoxazine and other groups, so that the high-efficiency deep-blue photo-thermal activation delayed fluorescent material is constructed, the external quantum efficiency of the organic electroluminescent device prepared based on the material is improved, the efficiency is slowly attenuated, and the service life of the organic electroluminescent device is further prolonged.
Drawings
In order to illustrate the embodiments or the technical solutions in the prior art more clearly, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the invention, and it is obvious for a person skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a flow chart illustrating the steps of a method for preparing a thermally activated delayed fluorescence material of the present invention;
fig. 2 is a schematic structural view of an organic light emitting device of the present invention;
FIG. 3 is an electroluminescence spectrum of compound 1, compound 2 and compound 3 at room temperature under atmospheric pressure.
Detailed Description
The following description of the various embodiments refers to the accompanying drawings that illustrate specific embodiments in which the invention may be practiced. The directional terms mentioned in the present invention, such as [ upper ], [ lower ], [ front ], [ rear ], [ left ], [ right ], [ inner ], [ outer ], [ side ], are only referring to the directions of the attached drawings. Accordingly, the directional terms used are used for explanation and understanding of the present invention, and are not used for limiting the present invention. In the drawings, elements having similar structures are denoted by the same reference numerals.
The invention aims at the problems that the stability of an OLED device is not high and the performance of the OLED device is influenced because the types of the existing thermal activation delayed fluorescent materials are lack, the selectivity of the materials is not much, and the efficiency attenuation of the materials applied to the OLED device is high.
The invention provides a thermal activation delayed fluorescent material, which has a chemical structural formula shown as a general formula (A):
Specifically, the R group is selected from one of carbazole group, phenoxazine group or other diphenylamine group.
The R group may be selected from one of the following groups:
by taking tetraphenylethylene as a core and connecting groups such as carbazole, phenoxazine and the like, the high-efficiency deep blue light D-A-D type TADF material is constructed, and the organic electroluminescent device prepared from the material has high external quantum efficiency and slow efficiency attenuation.
As shown in fig. 1, the present invention further provides a method for preparing the thermally activated delayed fluorescent material, comprising the following steps:
s10, mixing a first reactant, a second reactant and a catalyst in a container to obtain a first mixture, wherein the second reactant is a diphenylamine compound, and the chemical structural formula of the first reactant is shown as a general formula (D):
s20, placing the container in a vacuum glove box, and adding an alkaline compound and a solvent into the container in the glove box to obtain a second mixture;
s30, carrying out heat treatment on the container filled with the second mixture to obtain a reaction solution;
s40, cooling and extracting the reaction liquid to obtain an organic mixture;
s50, removing impurities from the organic mixture to obtain the thermally activated delayed fluorescence material.
Specifically, the X group may be a bromine atom, and the second reactant may be selected from one of the following structural formulas:
in S30, the heat treatment temperature is 110 ℃, and the heat treatment time is 24 hours.
The alkaline compound is sodium tert-butoxide, and the solvent is toluene from which water and oxygen are removed.
The S40 includes: firstly, cooling the reaction solution to room temperature, and then pouring the reaction solution into ice water; and extracting with dichloromethane for three times, combining organic phases, and spinning into silica gel to obtain the organic mixture.
The S50 includes: firstly, separating the organic mixture by using a column chromatography method to obtain light blue powder; and purifying the light blue powder by using a sublimation instrument to obtain the thermal activation delayed fluorescent material.
The preparation method is described in detail below with reference to specific examples.
Example one
The structural formula of the thermally activated delayed fluorescence material synthesized in this example is as follows:
first, into a 100 ml two-necked flask, 5 mmol (2.80 g) of (E) -1, 2-bis (4-bromophenyl) -1, 2-bis (3, 5-difluorophenyl) ethylene, 10 mmol (2.09 g) of 9,10 dihydro-9, 9-diphenylacridine, 0.4 mmol (90 mg) of palladium acetate (Pd (OAc))2) And 1.2 mmol (0.34 g) of tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF4) To obtain a first mixture.
Wherein, the palladium acetate is used as a catalyst, the tri-tert-butylphosphine tetrafluoroborate is used as a catalyst ligand, and the catalyst can also be other palladium catalysts.
Then, the two-necked flask was placed in a vacuum glove box, and 12 mmol (1.12 g) of sodium tert-butoxide (NaOt-Bu) and 40 ml of toluene from which water oxygen was removed were added to the two-necked flask to obtain a second mixture.
The vacuum glove box is filled with inert gas, the toluene is used as a solvent, the sodium tert-butoxide is an alkaline substance, and acidic substances in subsequent reaction products can be removed.
And then, heating the two-mouth bottle at constant temperature, and reacting at 110 ℃ for 24 hours to obtain a reaction solution.
The reaction solution was cooled to room temperature, poured into 50 ml of ice water, extracted three times with dichloromethane, the organic phases were combined and spun into silica gel to give an organic mixed mixture.
Then, the organic mixture was separated and purified by column chromatography to obtain 2.7 g of light blue powder with a yield of 67%.
Wherein the volume ratio of dichloromethane to n-hexane in column chromatography is 1: 5.
Finally, the pale blue powder was purified using a sublimator to give 2.1 g of compound 1.
The synthetic route of the thermally activated delayed fluorescence material in the embodiment is as follows:
the chemical molecular formula of the thermal activation delayed fluorescence material is C56H42F4N2The theoretical relative molecular mass is 818.96, and the relative molecular mass of the compound 1 measured by a mass spectrometer is 818.33, which is close to the theoretical value, indicating that the compound 1 is an ideal target compound.
Example two
The structural formula of the thermally activated delayed fluorescent material synthesized by the method is as follows:
first, a 100 ml two-neck flask was charged with 5 mmol (2.80 g) of (E) -1, 2-bis (4-bromophenyl) -1, 2-bis (3, 5-difluorophenyl) ethylene, 12 mmol (2.2 g) of phenoxazine, 0.4 mmol (90 mg) of palladium acetate (Pd (OAc)2) And 1.2 mmol (0.34 g) of tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF4) To obtain a first mixture.
Then, the two-necked bottle was placed in a vacuum glove box, and 12 mmol (1.12 g) of sodium tert-butoxide (NaOt-Bu) and 40 ml of toluene from which water oxygen was removed were added to the two-necked bottle to obtain a second mixture.
And then, heating the two-mouth bottle at constant temperature, and reacting at 110 ℃ for 24 hours to obtain a reaction solution.
The reaction solution was cooled to room temperature, poured into 50 ml of ice water, extracted three times with dichloromethane, the organic phases were combined and spun into silica gel to give an organic mixed mixture.
Then, the organic mixture was separated and purified by column chromatography to obtain 2.4 g of light blue powder with a yield of 63%.
Wherein the volume ratio of dichloromethane to n-hexane in column chromatography is 1: 4.
Finally, the pale blue powder was purified using a sublimator to give 1.9 g of compound 2.
The synthetic route of the thermally activated delayed fluorescence material in the embodiment is as follows:
the chemical molecular formula of the thermal activation delayed fluorescence material is C50H30F4N2O2The theoretical relative molecular mass is 766.80, and the relative molecular mass of the compound 2 measured by a mass spectrometer is 766.22, which is close to the theoretical value, indicating that the compound 2 is an ideal target compound.
EXAMPLE III
The structural formula of the thermally activated delayed fluorescence material synthesized in this example is as follows:
first, into a 100 ml two-necked flask, 5 mmol (2.80 g) of (E) -1, 2-bis (4-bromophenyl) -1, 2-bis (3, 5-difluorophenyl) ethylene, 11 mmol (3.67 g) of 9, 9-diphenyl-9, 10-dihydroacridine, 0.4 mmol (90 mg) of palladium acetate (Pd (OAc))2) And 1.2 mmol (0.34 g) of tri-tert-butylphosphine tetrafluoroborate ((t-Bu)3HPBF4) To obtain a first mixture.
Then, the two-necked flask was placed in a vacuum glove box, and 12 mmol (1.12 g) of sodium tert-butoxide (NaOt-Bu) and 40 ml of toluene from which water oxygen was removed were added to the two-necked flask to obtain a second mixture.
And then, heating the two-mouth bottle at constant temperature, and reacting at 110 ℃ for 24 hours to obtain a reaction solution.
The reaction solution was cooled to room temperature, poured into 50 ml of ice water, extracted three times with dichloromethane, the organic phases were combined and spun into silica gel to give an organic mixed mixture.
Then, the organic mixture was separated and purified by column chromatography to obtain 3.0 g of light blue powder with a yield of 56%.
Wherein the volume ratio of dichloromethane to n-hexane in column chromatography is 1: 6.
Finally, the pale blue powder was purified using a sublimator to give 2.6 g of compound 3.
The synthetic route of the thermally activated delayed fluorescence material in the embodiment is as follows:
the chemical molecular formula of the thermal activation delayed fluorescence material is C76H50F4N2The theoretical relative molecular mass is 1067.24, and the relative molecular mass of the compound 3 measured by a mass spectrometer is 1066.39, which is close to the theoretical value, indicating that the compound 3 is an ideal target compound.
The molecular energy levels of compound 1, compound 2, and compound 3 synthesized in the above 3 examples are shown in table 1 below.
TABLE 1
| Compound (I) | PL Peak(nm) | S1(eV) | T1(eV) | EST(eV) | HOMO(eV) | LUMO(eV) |
| |
434 | 2.86 | 2.81 | 0.05 | -4.96 | -1.96 |
| Compound 2 | 435 | 2.88 | 2.82 | 0.06 | -4.98 | -1.99 |
| Compound 3 | 432 | 2.85 | 2.80 | 0.05 | -4.95 | -1.94 |
Wherein PL Peak is the photoluminescence Peak, S1Lowest singlet energy level, T1Is the lowest triplet energy level, Est is the electrochemical energy level, HOMO is the highest occupied orbital level of the molecule, and LUMO is the lowest unoccupied orbital level of the molecule.
As shown in FIG. 3, the luminescence spectral curves of the three compounds are consistent and substantially coincident, and the photoluminescence peak of the three compounds is around 430 nm, which indicates that the synthesized compound is a deep blue material.
As can be seen from Table 1, the energy gaps of HOMO and LUMO of the three compounds are wide, and the energy gap between the two is about 3.0 eV.
S of three compounds1States being energetically higher than TIThe energy difference between the two states is about 0.05eV, the energy difference between the two states is small enough, reverse intersystem crossing occurs in the molecule, and delayed fluorescence is generated.
As shown in fig. 2, the present invention also provides an organic light emitting device 100, wherein the organic light emitting device 100 includes a substrate 10, an anode 20, a light emitting layer 30, and a cathode 40 sequentially disposed on the substrate. The luminescent layer comprises the thermal activation delayed fluorescent material prepared by the method
The substrate 100 may be a thin film transistor array substrate, and the light-emitting layer 30 includes a hole injection layer, a hole transport layer, an organic material layer, an electron transport layer, and an electron injection layer, which are sequentially disposed on the substrate 100.
The anode 20 is made of indium tin oxide, and the thickness of the anode 20 is 50 nanometers.
The hole injection layer and the hole transport layer are a mixture of poly (3, 4-ethylenedioxythiophene) and polystyrene sulfonate, and the total thickness of the hole injection layer and the hole transport layer is 50 nanometers.
The organic material layer is the thermal activation delayed fluorescence material prepared by the method, and the thickness of the organic material layer is 40 nanometers.
The electron transport layer is 1,3, 5-tri (3- (3-pyridyl) phenyl) benzene, and the thickness of the electron transport layer is 40 nanometers.
The cathode 40 is a composite cathode and comprises a lithium fluoride film layer and an aluminum film layer, wherein the thickness of the lithium fluoride film layer is 1 nanometer, and the thickness of the aluminum film layer is 100 nanometers.
After the anode 10 is formed on the substrate 100, a mixture of poly 3, 4-ethylenedioxythiophene and polystyrene sulfonate, the above thermally activated delayed fluorescence material, and an aluminum material are sequentially spin-coated on the anode 10, and then 1,3, 5-tris (3- (3-pyridyl) phenyl) benzene, lithium fluoride, and an aluminum material are sequentially evaporated under a high vacuum condition, thereby preparing the organic light emitting device.
Taking the organic light emitting devices 1,2 and 3 prepared from the compound 1, the compound 2 and the compound 3 as examples, the current-luminance-voltage characteristics of the devices were measured at room temperature and atmospheric pressure, as shown in table 2.
TABLE 2
| Device with a metal layer | Maximum luminance (cd/m)2) | Starting voltage (V) | Chromaticity coordinate | Maximum external quantum efficiency (%) |
| Organic |
2103 | 4.4 | (0.14,0.13) | 12.3 |
| Organic light emitting device 2 | 2258 | 4.4 | (0.14,0.13) | 13.5 |
| Organic light emitting device 3 | 2079 | 4.5 | (0.14,0.12) | 12.1 |
Has the advantages that: by using tetraphenyl ethylene as a core and connecting groups such as carbazole, phenoxazine and the like, the high-efficiency deep blue photo-thermal activation delayed fluorescent material is constructed, so that the external quantum efficiency of an organic electroluminescent device prepared based on the material is improved, the efficiency is slowly attenuated, and the service life of the organic electroluminescent device is further prolonged.
In summary, although the present invention has been described with reference to the preferred embodiments, the above-described preferred embodiments are not intended to limit the present invention, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention, therefore, the scope of the present invention shall be determined by the appended claims.
Claims (6)
1. A thermally activated delayed fluorescence material, wherein the chemical structural formula of the thermally activated delayed fluorescence material is shown as a general formula (A):
2. a preparation method of a thermal activation delayed fluorescent material is characterized in that the chemical structural formula of the thermal activation delayed fluorescent material is shown as a general formula (A):
s10, mixing a first reactant, a second reactant and a catalyst in a container to obtain a first mixture, wherein the chemical structural formula of the first reactant is shown as the general formula (D):
s20, placing the container in a vacuum glove box, and adding an alkaline compound and a solvent into the container in the glove box to obtain a second mixture;
s30, carrying out heat treatment on the container filled with the second mixture to obtain a reaction solution;
s40, cooling and extracting the reaction liquid to obtain an organic mixture;
s50, removing impurities from the organic mixture to obtain the thermally activated delayed fluorescent material;
the second reactant is selected from one of the following structural formulas:
3. the method according to claim 2, wherein in the step S30, the heat treatment temperature is 110 degrees celsius, and the heat treatment time is 24 hours.
4. The method according to claim 2, wherein the basic compound is sodium tert-butoxide and the solvent is toluene from which water and oxygen are removed.
5. The method according to claim 4, wherein the S50 includes:
s501, separating the organic mixture by using a column chromatography method to obtain light blue powder;
s502, purifying the light blue powder by using a sublimator to obtain the thermal activation delayed fluorescent material.
6. An organic electroluminescent device, comprising a substrate, an anode, a light-emitting layer and a cathode sequentially disposed on the substrate, wherein the light-emitting layer comprises the thermally activated delayed fluorescent material prepared by the preparation method of any one of claims 2 to 5.
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