CN111072641B - Orange photo-thermal activation delay fluorescent material and synthetic method and application thereof - Google Patents
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Abstract
The invention discloses an orange photo-thermal activation delay fluorescent material, a synthesis method and application thereof, and belongs to the technical field of organic photoelectric materials and devices. The orange photo-thermal activation delay fluorescent material is DV-Cz-DCPP, is a thermal crosslinking TADF molecule, can avoid the use of metal catalysts in the polymerization process, does not need further purification treatment, and simplifies the polymer synthesis and purification process. In the application, the in-situ polymerization method can avoid the re-dissolution process of the polymer, integrate the polymer synthesis process with the luminescent layer film manufacturing process, and simplify the device manufacturing process; and the proportion of the main guest content can be accurately controlled, which is beneficial to improving the stability and the luminous quality of the white light device. The polymer film after in-situ crosslinking by using DV-Cz-DCPP has the characteristics of good film forming performance, good stability, strong solvent erosion resistance and the like, is convenient for further spin coating of an electron transport material, provides guarantee for an all-wet method device, improves the utilization rate of the material, reduces the cost and improves the productivity.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials and devices, and particularly relates to an orange light thermal activation delay fluorescent material, a synthesis method and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) have the advantages of high efficiency, low power consumption, wide viewing angle, flexibility, capability of realizing large-area display, and the like, and become the main development direction of next-generation solid-state lighting and information display. Through the efforts of scientific researchers for decades, the luminous efficiency and stability of the OLED have met the requirements of small and medium-sized displays, and the OLED is widely applied to instruments and meters and high-end smart phones, and meanwhile, large-sized curved-surface OLED televisions have entered the market. At present, the OLED capable of meeting the commercial application requirements is realized based on a multi-layer device, the structure is relatively complex, a preparation process of vapor deposition is needed, the production cost is high, and heterojunction is easy to exist between functional layers; compared with the prior art, the device with a simple structure and capable of being processed by the full wet process can realize large-area display with low cost, and has wider application prospect.
Luminescent materials are the core part in OLEDs. The Thermal Activation Delayed Fluorescence (TADF) material realizes the utilization way of cheap triplet excitons by utilizing the all-organic material on the premise of no heavy metal atoms, thereby realizing 100% of theoretical internal quantum efficiency, creating a premise for the development of low-cost and high-efficiency devices and simultaneously bringing an innovative era for the development of OLED. Today, TADF materials have been considered as the third generation organic electroluminescent materials following conventional fluorescent and phosphorescent materials. Up to now, a great deal of efficient vapor deposition TADF materials have been successfully developed and have demonstrated unprecedented advantages. However, there are few TADF materials available for wet preparation, and therefore, the development of novel wettable TADF materials has important research significance for further reducing the production cost of OLED devices.
At present, the TADF polymer material has good wet film forming property and good solvent erosion resistance, and can be suitable for processing wet solution OLED devices. Andrey et al (adv. Mater.2015,27, 7236-7240) reported for the first time that the preparation of TADF polymeric materials by metal catalyzed polymerization of the host-guest components avoided the effects of phase separation and achieved 100% exciton utilization. Adachi et al (adv. Mater.2016,28, 4019-4024) report two TADF polymer materials that have green and yellow OLED maximum external quantum efficiencies as high as 8.1% and 9.3%. Subsequently, many researchers have used the preparation of high efficiency wet OLED devices by synthesizing TADF polymeric materials.
However, most of the currently reported TADF polymers employ metal catalytic systems, which makes the purification process very difficult, and at the same time, precise control of the host guest content in the TADF polymer is difficult to achieve. Meanwhile, the development of the high-efficiency orange light TADF is more backward than that of the blue light TADF, and the external quantum efficiency of the orange light TADF reported at present is far lower than that of the blue light TADF. In addition, the wet processing of the device is complicated, a proper solvent is required to be screened to dissolve the polymer, and then a thin film of the polymer is obtained by spin-coating and heating annealing, so that the research on the all-wet OLED device is further limited.
Disclosure of Invention
The technical problems to be solved are as follows: aiming at the technical problems, the invention provides an orange light thermal activation delay fluorescent material, a synthesis method and application thereof, wherein the orange light TADF is a thermal crosslinking TADF molecule, can be processed into a film on a hole transport layer through a solution, and is heated and annealed to form a polymer luminous layer film with excellent film forming performance and good solution corrosion resistance, so that an OLED device prepared by a full wet method can be obtained by further spin coating a wet electron transport material on the luminous layer.
The technical scheme is as follows: an orange light thermal activation delay fluorescent material has a structural formula:
the orange photo-thermal activation delay fluorescent material is DV-Cz-DCPP, and the molecular structure analysis result is as follows:
nuclear magnetic hydrogen spectrum (500 MHz, CDCl) 3 )：9.45(d,J＝8.6Hz,2H),8.79(s,2H),8.16(d,J＝8.4Hz,4H),7.61(d,J＝8.2Hz,8H),7.49-7.40(m,8H),7.35(t,J＝7.6Hz,4H),6.71-6.75(m,2H),5.74(d,J＝10.8Hz,2H),5.24-5.28(t,2H),5.18(s,4H)。
Mass spectrometry: 874.52.
elemental analysis: c:82.36, h:4.38, n:9.60.
the synthesis method of the orange light thermal activation delay fluorescent material comprises the following steps:
(1) Adding 5, 6-bis (4-bromophenyl) pyrazine-dinitrile into N, N-dimethylformamide, stirring and dissolving, respectively adding cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxycarbazole, wherein the molar ratio of the cuprous iodide to the 5, 6-bis (4-bromophenyl) pyrazine-dinitrile is 0.1, 2 and 2.2, the reaction is carried out under the protection of nitrogen, the temperature is 140 ℃, the reaction time is 24 hours, and after the reaction is finished, purifying the crude product by a column chromatography to obtain a product A:5, 6-bis (4- (3-methoxy-9-hydro-carbazolyl-9-yl) phenyl) pyrazine-2, 3-carbonitrile;
(2) Adding the product A obtained in the step (1) into chloroform, stirring and dissolving, and then dropwise adding a boron tribromide solution, wherein the molar ratio of the boron tribromide solution to the product A is 2:1, the reaction temperature is 0 ℃, the reaction time is 3 hours, the reaction is quenched by methanol solution, and the organic solvent is dried by spin to obtain a product B:5, 6-bis (4- (3-hydroxy-9-hydro-carbazolyl-9-yl) phenyl) pyrazine-2, 3-carbonitrile;
(3) Adding the product B obtained in the step (2) into dry N, N-dimethylformamide, stirring and dissolving, and adding the mixture into the mixture, wherein the molar ratio of the product B to the product B is 3:1 after 20 minutes of reaction, the molar ratio of added sodium hydride to product B was 4:1, wherein the reaction temperature is 60 ℃ and the reaction time is 24 hours; after the reaction is finished, purifying by column chromatography to obtain the orange light thermal activation delay fluorescent material;
the reaction formula is:
the orange light thermal activation delay fluorescent material is applied to preparing wet white light organic electroluminescent diodes.
Preferably, the application comprises the steps of:
(1) Cleaning the anode electrode, and respectively cleaning with distilled water, acetone and isopropanol; drying under dust-free conditions;
(2) Spin-coating a hole light-emitting layer on the anode at the rotating speed of 2000rpm, and heating and annealing in a glove box filled with nitrogen after spin-coating is completed;
(3) Spin-coating a mixed material containing a thermal crosslinking main unit, a blue light and orange light thermal activation delay fluorescent unit in different proportions on the hole transport layer, wherein the rotating speed is 1500-3000rpm, and heating and crosslinking are carried out in a glove box filled with nitrogen after spin-coating is completed;
(4) Spin-coating an alcohol-soluble electron transport material on the light-emitting layer as an electron transport layer, and evaporating a cathode to obtain the wet white light organic electroluminescent diode.
Preferably, the annealing temperature in the step (2) is 80-120 ℃.
Preferably, the temperature of the heating crosslinking in the step (3) is 150-250 ℃.
Preferably, the main unit of the thermal crosslinking in the step (3) is DV-CDBP, and the structural formula is as follows:
preferably, the blue light thermal activation delay fluorescent material in the step (3) is DV-MOC-DPS, and the structural formula is as follows:
the wet white light organic electroluminescent diode is prepared by applying the orange light thermal activation delay fluorescent material.
The beneficial effects are that: firstly, the orange light TADF is a thermal crosslinking molecule, can avoid the use of metal catalysts in the polymerization process, does not need further purification treatment, and simplifies the polymer synthesis and purification process. Secondly, the in-situ polymerization method can avoid the re-dissolution process of the polymer, integrate the polymer synthesis process with the luminescent layer film manufacturing process, and simplify the device manufacturing process. Thirdly, in the process of in-situ thermal polymerization, the proportion of the main guest content can be precisely controlled, which is beneficial to improving the stability and the luminous quality of the white light device. Fourth, the polymer film after in-situ crosslinking has the characteristics of good film forming performance, good stability, strong solvent erosion resistance and the like, is convenient for further spin coating of the electron transport material, provides guarantee for the all-wet method device, improves the utilization rate of the material, reduces the cost and improves the productivity.
Drawings
FIG. 1 is a schematic diagram of an in situ polymerization process for preparing a wet white light emitting layer;
FIG. 2 is a schematic diagram of the structure of the organic light emitting diode;
the numerical references in the drawings are as follows: an ITO anode; 2. a hole transport layer; 3. a light emitting layer; 4. an electron transport layer; 5. a metal cathode.
Detailed Description
The following description of the embodiments of the present invention will clearly and fully describe the technical solutions of the embodiments of the present invention in conjunction with the specific contents of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.
The materials used in the invention are as follows:
wherein the materials DV-MOC-DPS and DV-CDBP were synthesized by the inventors and published (J. Mater. Chem. C,2016,4,8973-8979), PEDOT: PSS and PO-T2T are commercially available.
Example 1
Preparation of orange light TADF:
the structural formula is as follows:
the synthesis method comprises the following steps:
(1) 3g of 5, 6-bis (4-bromophenyl) pyrazine-dinitrile is added into a 100mL eggplant-shaped bottle dissolved with 30mL of N, N-dimethylformamide, and stirred and dissolved, and then cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxycarbazole are respectively added, wherein the molar ratio of the potassium carbonate to the 5, 6-bis (4-bromophenyl) pyrazine-dinitrile is 0.1, 2 and 2.2, the reaction is carried out under the protection of nitrogen, the temperature is 140 ℃, and the reaction time is 24 hours. After the reaction is finished, purifying the crude product by a column chromatography method to obtain a product A: the eluent is petroleum ether and methylene dichloride mixed solution, and the yield is 64%.
(2) 1g of the product A obtained in the step (1) is added into a 100mL eggplant-shaped bottle dissolved with 30mL of chloroform, and after stirring and dissolution, the molar ratio of the dropwise addition to the product A is 2:1, the reaction temperature is 0 ℃ and the reaction time is 3 hours. Quenching the reaction with methanol solution, and spin-drying the organic solvent to obtain a product B with a yield of 95%: 5, 6-bis (4- (3-hydroxy-9-hydro-carbazolyl-9-yl) phenyl) pyrazine-2, 3-carbonitrile.
(3) Adding 0.8g of the product B obtained in the step (2) into a 100mL eggplant-shaped bottle dissolved with 30mL of dried N, N-dimethylformamide, stirring and dissolving, adding sodium hydride with the molar ratio of 3:1 to the product B for reaction for 20 minutes, and adding 4-chloro-methyl styrene with the molar ratio of 4:1 to the product B, wherein the reaction temperature is 60 ℃, and the reaction time is 24 hours. After the reaction is finished, purifying the crude product by a column chromatography method to obtain the orange light thermal activation delay fluorescent material, wherein the eluent is a mixed solution of petroleum ether and dichloromethane, and the yield is 45%.
The reaction formula is as follows:
wet white light OLED devices were prepared:
the structure of the device is shown in the schematic diagram that ITO/PEDOT is PSS (30 nm)/DV-CDBP is DV-MOC-DPS is DV-Cz-DCPP (40 nm)/PO-T2T (40 nm)/Cs 2 CO 3 (1 nm)/Al (100 nm) as shown in FIG. 2. The specific process for preparing the device is as follows:
1. cleaning an Indium Tin Oxide (ITO) glass substrate: respectively using a detergent, deionized water, ethanol, acetone and isopropanol to ultrasonically clean ITO, respectively using each solvent for 3 times, drying for 1 hour under the irradiation of an infrared lamp, and finally cleaning the ITO with ultraviolet ozone for half an hour for later use.
2. Spin coating of hole transport layer: spin-coating an anode buffer layer PEDOT on the surface of ITO at 3000 rpm: PSS (poly (3, 4-vinyldioxythiophene) -poly (styrenesulfonic acid)) was 40nm in film thickness. The substrate was then dried on a 120℃hot plate for 20min.
3. Preparation of the light-emitting layer: after cooling to room temperature, 1, 2-dichloroethane dissolved with luminescent material (DV-CDBP: DV-MOC-DPS: DV-Cz-DCPP in a mass ratio of 1:0.1:0.03, respectively) at a concentration of 10mg/mL was spin-coated on PEDOT: above PSS, the rotation speed was 2000rpm and the time was 30 seconds. Dried under nitrogen at 200 ℃ for 10 minutes and cooled to room temperature.
4. Spin coating of electron transport layer: an electron transport layer PO-T2T having a concentration of 5mg/mL was spin-coated on the surface of the light-emitting layer at 2000rpm, and the film thickness was 40nm. The substrate was then dried on a 120℃hot plate for 20min.
5. Vapor deposition of cathode: respectively by
And->
Is evaporated at a rate of Cs 2 CO 3 And Al as a cathode.
Performance test of the device: the brightness-current-voltage curve of the device was measured in a glove box using a Kethiey 2400 semiconductor performance test system connected to an ST-86LA screen brightness meter. Meanwhile, an electroluminescence spectrum and a color coordinate were measured using a PR655 type spectrometer.
The resulting device performance was as follows: the brightness-up voltage is 4.5V, and the maximum brightness is 5612cd/m 2 The color coordinates were (0.33,0.38) and the maximum external quantum efficiency was 5.6%.
Example 2
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.1:0.02 respectively.
The resulting device performance was as follows: the brightness-up voltage is 4.1V, and the maximum brightness is 6015cd/m 2 The color coordinates were (0.33,0.41) and the maximum external quantum efficiency was 6.5%.
Example 3
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.12:0.03 respectively.
The resulting device performance was as follows: the brightness-up voltage is 4.2V, and the maximum brightness is 8188cd/m 2 The color coordinates were (0.33,0.35) and the maximum external quantum efficiency was 8.1%.
Example 4
Orange TADF and OLED devices were prepared as in example 1, except that in the light emitting layer of the device, DV-CDBP: DV-MOC-DPS: the mass ratio of DV-Cz-DCPP is 1:0.12:0.02 respectively.
The resulting device performance was as follows: the brightness-up voltage is 4.5V, and the maximum brightness is 7223cd/m 2 The color coordinates were (0.33,0.39) and the maximum external quantum efficiency was 4.8%.
The orange light thermal activation delay fluorescent material, the synthesis method and the application thereof provided by the invention are described in detail. The polymer film is obtained only through in-situ heating and crosslinking in the process of manufacturing the luminous layer, so that the polymer synthesis and purification process and the device manufacturing process are simplified. Meanwhile, the proportion of the contents of the main body and the guest body can be accurately controlled, and the luminous quality of the white light device is effectively improved. The invention and embodiments are described herein with reference to specific examples, which are not intended to limit the invention. Any simple modifications of the present invention without departing from the principles of the invention shall fall within the scope of the appended claims.
Claims (10)
1. The orange light thermal activation delay fluorescent material is characterized by comprising the following structural formula:
2. the synthesis method of the orange light thermal activation delay fluorescent material according to claim 1, which is characterized by comprising the following steps:
(1) Adding 5, 6-bis (4-bromophenyl) pyrazine-dinitrile into N, N-dimethylformamide, stirring and dissolving, respectively adding cuprous iodide, 1, 10-phenanthroline, potassium carbonate and 3-methoxycarbazole, wherein the molar ratio of the cuprous iodide to the 5, 6-bis (4-bromophenyl) pyrazine-dinitrile is 0.1, 2 and 2.2, the reaction is carried out under the protection of nitrogen, the temperature is 140 ℃, the reaction time is 24 hours, and after the reaction is finished, purifying the crude product by a column chromatography to obtain a product A:5, 6-bis (4- (3-methoxy-9-hydro-carbazolyl-9-yl) phenyl) pyrazine-2, 3-carbonitrile;
(2) Adding the product A obtained in the step (1) into chloroform, stirring and dissolving, and then dropwise adding a boron tribromide solution, wherein the molar ratio of the boron tribromide solution to the product A is 2:1, the reaction temperature is 0 ℃, the reaction time is 3 hours, the reaction is quenched by methanol solution, and the organic solvent is dried by spin to obtain a product B:5, 6-bis (4- (3-hydroxy-9-hydro-carbazolyl-9-yl) phenyl) pyrazine-2, 3-carbonitrile;
(3) Adding the product B obtained in the step (2) into dry N, N-dimethylformamide, stirring and dissolving, and adding the mixture into the mixture, wherein the molar ratio of the product B to the product B is 3:1 after 20 minutes of reaction, the molar ratio of added sodium hydride to product B was 4:1, wherein the reaction temperature is 60 ℃ and the reaction time is 24 hours; after the reaction is finished, purifying by column chromatography to obtain the orange light thermal activation delay fluorescent material;
the reaction formula of the method is as follows:
3. the method for synthesizing the orange light thermal activation delay fluorescent material according to claim 2, wherein the eluent in the column chromatography in the step (1) and the step (3) is a petroleum ether and dichloromethane mixed solution.
4. The application of the orange light thermal activation delay fluorescent material according to claim 1, wherein the orange light thermal activation delay fluorescent material is used for preparing a wet white light organic electroluminescent diode.
5. The use of an orange light thermal activation delay fluorescent material as claimed in claim 4, wherein said use comprises the steps of:
(1) Cleaning the anode electrode, and respectively cleaning with distilled water, acetone and isopropanol; drying under dust-free conditions;
(2) Spin coating of hole transport layer: spin-coating an anode buffer layer PEDOT on the surface of ITO at 3000 rpm: PSS (poly (3, 4-vinyldioxythiophene) -poly (styrenesulfonic acid)) film thickness 40nm; heating and annealing in a glove box filled with nitrogen after spin coating is completed;
(3) Spin-coating a mixed material containing a thermal crosslinking main unit, a blue light and orange light thermal activation delay fluorescent unit in different proportions on the hole transport layer, wherein the rotating speed is 1500-3000rpm, and heating and crosslinking are carried out in a glove box filled with nitrogen after spin-coating is completed;
(4) Spin-coating an alcohol-soluble electron transport material on the light-emitting layer as an electron transport layer, and evaporating a cathode to obtain the wet white light organic electroluminescent diode.
6. The use of an orange light-heat activated delayed fluorescence material according to claim 5, wherein the annealing temperature in step (2) is 80-120 ℃.
7. The use of an orange light heat activated delayed fluorescence material as defined in claim 5, wherein the temperature of heat crosslinking in said step (3) is 150-250 ℃.
8. The use of an orange light heat activated delayed fluorescence material according to claim 5, wherein the heat cross-linked host unit in step (3) is DV-CDBP, and has the following structural formula:
9. the use of an orange light heat activated delayed fluorescence material according to claim 5, wherein the blue light heat activated delayed fluorescence material in step (3) is DV-MOC-DPS, and has the following structural formula:
10. wet white light organic electroluminescent diode based on the use of an orange light thermally activated delayed fluorescence material as claimed in any of claims 4-9.
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