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A solution processable delayed fluorescent polymer material and its application
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A polymer material, delayed fluorescence technology, applied in the field of organic light-emitting materials, can solve the problems of delayed fluorescence material solubility, poor film formation, unsuitable for spin coating, etc. Sexual and penetrating effects
Active Publication Date: 2019-06-25
山西穿越光电科技有限责任公司
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[0006] Therefore, the technical problem to be solved by the present invention is to overcome the defects of poor solubility and film-forming properties of the retarded fluorescent material in the prior art, which are not suitable for the spin-coating method, so as to provide a solution-processable retardation film suitable for the spin-coating method. Fluorescent polymer materials and their applications
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Embodiment 1
[0032] This example provides a method for preparing a solution-processable delayed fluorescence polymer material I-1, and the specific steps are:
[0033] (1) Preparation of Intermediate 1
[0034]
[0035] Under a nitrogen atmosphere, add 0.146g (0.75mmol) of acridone to 20mL of anhydrous tetrahydrofuran and stir to dissolve, slowly add 0.5mL of 1.6M (0.8mmol) n-BuLi dropwise under an ice bath, react for 30 minutes, and add to the resulting suspension Add 0.22g (0.8mmol) 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.046g (0.04mmol) 10mL tetrahydrofuran slowly into the turbid liquid The solution was heated under reflux at 65°C for 12 hours, and cooled to room temperature after the reaction. Sequentially add dichloromethane and saturated sodium chloride for extraction, collect the organic layer, remove the organic solvent by rotary evaporation, and recrystallize with 10 mL of toluene to obtain 0.224 g of solid, with a yield of 70%.
[0036] 1 H NMR (400MHz, CDCl 3 ,δ):8.36(...
Embodiment 2-4
[0053] The preparation method of compound I-2, I-3, and I-4 of embodiment 2-4 is the same as that of compound I-1 in embodiment 1, and its difference is that R in R-Br or R-Cl is 2~ The substituent shown in 4 replaces the compound I-1 in Example 1, and the specific process will not be repeated.
[0054]
[0055] In order to better illustrate the performance of the thermally activated delayed fluorescence of the compounds of the present invention, the calculations of compounds I-2, I-3, and I-4 in Examples 2-4 were obtained by the simulation method as described in Example 1. For energy data, see Table 1 below for specific results.
[0056] Table 1 Physical test data of materials
[0057]
[0058] In Table 1, HOMO means: the highest occupied molecular orbital;
[0059] LUMO means: the lowest unoccupied molecular orbital;
[0060] S 1 Represents: excited singlet energy;
[0061] T 1 Represents: excited triplet energy;
[0062] ΔE ST Indicates: the energy difference ...
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Abstract
The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a solution-processable delayed fluorescent polymer material and an application thereof. Its structure is represented by formula (I), with spiroacridine as the core as the hole transport unit, and the electron transport unit R represented by diphenyltriazine is connected through a saturated N single bond. 1 , using the method of copolymerization, the small molecule and the side chain containing the solubilizing side chain R 2 The fluorene units of the polymer are connected together to form a polymer, which makes the polymer have good solubility and wettability, which is conducive to its processing into a film by solution. Due to the thermally induced delayed fluorescence characteristics of this kind of material, the triplet energy can be utilized, which can greatly improve the device efficiency, and at the same time, it does not require expensive noble metals and can effectively reduce the production cost of the product.
Description
technical field [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a solution-processable delayed fluorescent polymer material and an application thereof. Background technique [0002] Organic Light Emitting Devices (OLEDs) are a display technology that utilizes organic materials as semiconductor materials in light emitting diodes. OLEDs display technology has the characteristic of self-luminescence. The principle of luminescence is that when a forward bias voltage is applied, holes (holes) and electrons (electrons) are injected into the organic layer from the anode and cathode, respectively, and then driven by an electric field in the organic layer. Migrating to the respective electrodes, holes and electrons are captured by organic light-emitting molecules when migrating to the organic functional layer with light-emitting properties, forming excitons (exciton). Excitons in an unstable energy state will quic...
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