CN111116871A - Preparation method of efficient blue-light polyfluorene spherical crystal material - Google Patents
Preparation method of efficient blue-light polyfluorene spherical crystal material Download PDFInfo
- Publication number
- CN111116871A CN111116871A CN201911388753.3A CN201911388753A CN111116871A CN 111116871 A CN111116871 A CN 111116871A CN 201911388753 A CN201911388753 A CN 201911388753A CN 111116871 A CN111116871 A CN 111116871A
- Authority
- CN
- China
- Prior art keywords
- preparation
- polymer
- light
- polyfluorene
- crystal material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/11—Homopolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
- C08G2261/1424—Side-chains containing oxygen containing ether groups, including alkoxy
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/18—Definition of the polymer structure conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
- C08G2261/5222—Luminescence fluorescent electrofluorescent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/59—Stability
- C08G2261/592—Stability against heat
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
Abstract
The invention belongs to the technical field of organic photoelectric materials and information display, and particularly relates to a preparation method of a high-efficiency blue-light polyfluorene spherical crystal material, which comprises the following specific preparation steps: s1: preparing a polymerized monomer; s2: preparing a polymer; s3: the preparation of polymer spherulites, thermogravimetric analysis and differential thermal analysis tests of the polymer material prove that the polymer photoelectric functional material shows good thermal stability, and the electrochemical property represented by cyclic voltammetry shows that the oxidation potential is not obviously changed, so that the good electroluminescent capability of 9, 9-diaryl fluorene is maintained; the invention provides a method for growing the conjugated polymer PEODPF into spherulites on the basis of material preparation, so that PLEDs and an organic laser can obtain stable deep blue emission, and the conjugated polymer PEODPF can be used as a high-efficiency stable blue light main body material in the display fields of polymer organic light-emitting diodes and the like.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials and information display, in particular to a preparation method of a high-efficiency blue-light polyfluorene spherical crystal material.
Background
Information technology is one of the core fields of the whole modern science and technology, and information display technology is an important link of the information technology. Since small molecule and polymer electroluminescent diodes (OLED/PLED) were invented by Tang research group of Kodak corporation in 1987 and by Friend and Heeger, Cambridge university of England in 1990, the OLED/PLED has become a research hotspot for people due to the advantages of low preparation cost, abundant material types, high structure selectivity, adjustable performance, simple preparation process, low-cost manufacture, biocompatibility, device miniaturization, ultrathin flexibility and the like. At present, polymer organic semiconductors are widely applied to organic optoelectronic fields such as polymer light emitting diodes, organic lasers, polymer solar cells, thin film transistors and the like. Conjugated Polymers (CPs) have gained increased attention in recent decades due to their potential application in solution processed plastic opto-electronic devices. Through precise control of electronic structures, many effective molecular design strategies are proposed to construct high-performance, stable CPs. However, in addition to customizable molecular p-n engineering, the aggregation behavior and thin film morphology of CPs also play a key role in controlling photophysical processes, exciton diffusion, and charge transport. In this regard, control of the condensed superstructure of light-emitting conjugated polymers (LCPs) is a key factor in achieving high-performance, stable organic opto-electronic devices. The precise balance of interchain aggregation and steric hindrance in LCPs is the primary factor in inducing chain conformation and aggregation behavior abundant in solution state. Among all structural elements, the side chains are key factors in controlling interchain aggregation and regulating solution and membrane-state chain conformation.
Among them, polyfluorene organic semiconductors represented by poly-9, 9-dioctylfluorene (PFO) have been widely used in the fields of organic light emitting diodes and thin film transistors due to their advantages of high carrier mobility, relatively stable deep blue light emission, high fluorescence efficiency, and the like. However, the organic light emitting diode using poly-9, 9-dioctyl fluorene material as the light emitting layer can emit green light band between 510nm and 580nm in long-term use, and this defect seriously affects the light emitting stability and the service life of the device.
Disclosure of Invention
The invention aims to provide a preparation method of a high-efficiency blue-light polyfluorene spherical crystal material, which aims to solve the problem that the defect that the light-emitting stability and the service life of a device are seriously influenced because an organic light-emitting diode which is provided in the background technology and takes a poly-9, 9-dioctyl fluorene material as a light-emitting layer shows green light band emission between 510nm and 580nm in long-time use.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of a high-efficiency blue-light polyfluorene spherical crystal material comprises the following specific preparation steps:
s1: preparation of polymerized monomers:
a: preparing lactone from 2, 7-dibromo-9-fluorenone through Bayer-Virgille rearrangement reaction;
b: preparing 2, 7-dibromodiol from lactone through Grignard reaction;
c: alkyl substitution reaction of 4-position alcohol group of 2, 7-dibromodiol;
d: the main polymer monomer is prepared by Friedel-crafts reaction of the product obtained in the previous step;
s2: preparation of the polymer: taking the same amount of bipyridine and nickel catalyst Ni (COD)2In full of N2The two-neck flask is then activated for 20min in DMF solution at 75 ℃, then added with polymerization monomer solution dissolved by toluene, refluxed for 3 days at 85 ℃, then capped by 0.1ml of dry bromobenzene, finally quenched by THF and hydrazine hydrate, and the silicon-based metal remover is used for removing residual nickel catalyst in the post-treatment process, and then evaporated and settled by absolute methanol, and finally extracted by absolute methanol for 3 days, and then dried in vacuum to obtain a powdery product, namely a polymer;
s3: preparation of polymer spherulites: the polymer in step S2 may be grown into spherulites.
Preferably, the reaction in a in S1 is specifically carried out by reacting 2, 7-dibromofluorenone for 72h at room temperature under the conditions of trifluoroacetic acid and sodium percarbonate.
Preferably, in the step b of S1, 2, 7-dibromolactone reacts with 4-6 times of equivalent of bromobenzene Grignard reagent, the solvent is toluene, and the reaction is carried out at 85 ℃ for 24 hours under the protection of nitrogen.
Preferably, c in S1 is specifically 2, 7-dibromodiol and 1.5 times of equivalent of 1-bromo-hexylcarbazole, and the compound is prepared by reacting for 24 hours at room temperature and under an alkaline condition with acetone as a solvent.
Preferably, d in S1 is the product obtained in the previous step, which is dissolved in anhydrous dichloromethane and reacted for 2h under the catalysis of boron trifluoride-diethyl ether to obtain the polymerized monomer.
Preferably, the specific steps of S3 are as follows:
step 1: taking a weighing bottle, putting a bracket in the weighing bottle, and putting a silicon wafer on the bracket;
step 2: taking a proper amount of chloroform solution of the polymer by a pipette, dripping the chloroform solution on a silicon wafer, and sucking the chloroform solution in a proper amount in a weighing bottle by a rubber head dropper;
and step 3: the temperature of the drying oven is set to be 40 ℃, the weighing bottle is carefully placed in the drying oven, the drying oven is closed until the solvent in the weighing bottle is volatilized, and the time is 12 hours.
Compared with the prior art, the invention has the beneficial effects that:
1) the polymer material is proved to show good thermal stability by thermogravimetric analysis and differential thermal analysis tests, and the electrochemical property represented by cyclic voltammetry shows that the oxidation potential is not obviously changed, so that the good electroluminescent capability of the 9, 9-diaryl fluorene is maintained;
2) the invention provides a method for growing the conjugated polymer PEODPF into spherulites on the basis of material preparation, so that PLEDs and an organic laser can obtain stable deep blue emission, and the conjugated polymer PEODPF can be used as a high-efficiency stable blue light main body material in the display fields of polymer organic light-emitting diodes and the like.
Drawings
FIG. 1 is a flow chart of a preparation method of the present invention;
FIG. 2 is a flow chart of the preparation of the polymerized monomers of the present invention;
FIG. 3 is a chemical formula diagram of a polymer of the present invention;
FIG. 4 is a graph showing an emission spectrum of a grown spherulite of the present invention;
FIG. 5 is a schematic structural diagram of a cultured spherulite according to the present invention;
FIG. 6 is an optical micrograph of a grown spherulite of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the description of the present invention, it is to be understood that the terms "upper", "lower", "front", "rear", "left", "right", "top", "bottom", "inner", "outer", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, are merely for convenience in describing the present invention and simplifying the description, and do not indicate or imply that the device or element being referred to must have a particular orientation, be constructed and operated in a particular orientation, and thus, should not be construed as limiting the present invention.
Referring to fig. 1-3, the present invention provides a technical solution: a preparation method of a high-efficiency blue-light polyfluorene spherical crystal material comprises the following specific preparation steps:
s1: preparation of polymerized monomers:
a: preparing lactone from 2, 7-dibromo-9-fluorenone through Bayer-Virgille rearrangement reaction;
b: preparing 2, 7-dibromodiol from lactone through Grignard reaction;
c: alkyl substitution reaction of 4-position alcohol group of 2, 7-dibromodiol;
d: the main polymer monomer is prepared by Friedel-crafts reaction of the product obtained in the previous step;
s2: preparation of the polymer: taking the same amount of bipyridine and nickel catalyst Ni (COD)2In full of N2The two-neck flask is then activated for 20min in DMF solution at 75 ℃, then added with polymerization monomer solution dissolved by toluene, refluxed for 3 days at 85 ℃, then capped by 0.1ml of dry bromobenzene, finally quenched by THF and hydrazine hydrate, and the silicon-based metal remover is used for removing residual nickel catalyst in the post-treatment process, and then evaporated and settled by absolute methanol, and finally extracted by absolute methanol for 3 days, and then dried in vacuum to obtain a powdery product, namely a polymer;
s3: preparation of polymer spherulites: the polymer in step S2 may be grown into spherulites.
Preferably, the reaction in a in S1 is specifically carried out by reacting 2, 7-dibromofluorenone for 72h at room temperature under the conditions of trifluoroacetic acid and sodium percarbonate.
Preferably, in the step b of S1, 2, 7-dibromolactone reacts with 4-6 times of equivalent of bromobenzene Grignard reagent, the solvent is toluene, and the reaction is carried out at 85 ℃ for 24 hours under the protection of nitrogen.
Preferably, c in S1 is specifically 2, 7-dibromodiol and 1.5 times of equivalent of 1-bromo-hexylcarbazole, and the compound is prepared by reacting for 24 hours at room temperature and under an alkaline condition with acetone as a solvent.
Preferably, d in S1 is the product obtained in the previous step, which is dissolved in anhydrous dichloromethane and reacted for 2h under the catalysis of boron trifluoride-diethyl ether to obtain the polymerized monomer.
Preferably, the specific steps of S3 are as follows:
step 1: taking a weighing bottle, putting a bracket in the weighing bottle, and putting a silicon wafer on the bracket;
step 2: taking a proper amount of chloroform solution of the polymer by a pipette, dripping the chloroform solution on a silicon wafer, and sucking the chloroform solution in a proper amount in a weighing bottle by a rubber head dropper;
and step 3: the temperature of the drying oven is set to be 40 ℃, the weighing bottle is carefully placed in the drying oven, the drying oven is closed until the solvent in the weighing bottle is volatilized, and the time is 12 hours.
Example (b):
the preparation method of the high-efficiency blue-light polyfluorene spherical crystal material comprises the following specific preparation steps:
s1: preparation of polymerized monomers:
a: lactone was prepared from 2, 7-dibromo-9-fluorenone by Bayer-Virgille rearrangement, and 2.8g (8.28mmol) of 2, 7-dibromofluorenone was dissolved in 30ml of dried dichloromethane, followed by addition of 25ml of trifluoroacetic acid. Adding sodium percarbonate Na every 15min under ice bath condition2CO41g, 5 times in total. Then the temperature is returned to room temperature and stirred for 72 hours, and after the reaction is completed, sodium bicarbonate NaHCO is used4The remaining trifluoroacetic acid was removed and extracted with dichloromethane followed by petroleum ether: purification on a dichloromethane (5:1) silica gel column to give a pale yellow powderSolid (85% yield);
b: the lactone is subjected to Grignard reaction to prepare 2, 7-dibromodiol, wherein 12ml of bromobenzene and magnesium chips (1.76g, 72.4mmol) are firstly taken to be reacted with one particle of iodine, and then tetrahydrofuran is added under ice bath and reacted for 2h under the protection of nitrogen until the magnesium chips are completely reacted. Then weighing 2, 7-dibromolactone (4.24g, 12mmol) and dissolving the 2, 7-dibromolactone in 60ml of anhydrous toluene, adding the prepared Grignard reagent, reacting at 85 ℃ for 24h, and reacting with saturated NH4The reaction was quenched with aqueous Cl, then extracted with dichloromethane, first with petroleum ether: dichloromethane 2:1, followed by petroleum ether: purification on a 6:1 silica gel column afforded a white solid (90% yield);
c: alkyl substitution reaction of the 4-position alcohol group of 2, 7-dibromodiol, weighing 2, 7-dibromodiol (2g, 4mmol), anhydrous potassium carbonate (1g, 7.2mmol), bromo-isooctane (1.5g, 7.8mmol), dissolving in 30ml acetone, then reacting for 24h at room temperature, then extracting with dichloromethane, drying and rotary steaming, and purifying with petroleum ether dichloromethane-8: 1 silica gel column to obtain transparent solid (yield 80%);
d: the product in the last step is prepared into a main polymer monomer by Friedel-crafts reaction, the product prepared in the step c is dissolved in anhydrous dichloromethane, then about 0.2ml of boron trifluoride ethyl ether is added for reaction for 2 hours at room temperature, then 5ml of water is added for extraction and quenching reaction, dichloromethane is used for extraction, drying and rotary evaporation are carried out, and petroleum ether dichloromethane (6: 1) is used for purification, so that a white solid is obtained, and the yield is (87%);
the above four steps are shown in fig. 2;
s2: preparation of the polymer: taking the same amount of bipyridine and nickel catalyst Ni (COD)2In full of N2The two-neck flask is then activated for 20min in DMF solution at 75 ℃, then added with polymerization monomer solution dissolved by toluene, refluxed for 3 days at 85 ℃, then capped by 0.1ml of dry bromobenzene, finally quenched by THF and hydrazine hydrate, and the silicon-based metal remover is used for removing residual nickel catalyst in the post-treatment process, and then evaporated and settled by absolute methanol, and finally extracted by absolute methanol for 3 days, and then dried in vacuum to obtain a powdery product, namely a polymer;
s3: preparation of polymer spherulites: the polymer in step S2 may be grown into spherulites:
step 1: taking a weighing bottle (50x30), putting a bracket in the weighing bottle, and putting a silicon wafer on the bracket;
step 2: taking a proper amount of chloroform solution (with the concentration of 10mg/ml) of the polymer by a pipette, dripping the chloroform solution on a silicon wafer, and sucking the chloroform solution into a weighing bottle (which cannot submerge a bracket) by a rubber head dropper;
and step 3: the temperature of the drying oven is set to be 40 ℃, the weighing bottle is carefully placed in the drying oven, the drying oven is closed until the solvent in the weighing bottle is volatilized, and the time is 12 hours.
The polymer spherulites prepared in the above examples were examined:
as shown in FIG. 4, the spectrum of the emitted light of the grown spherulites is shown;
FIG. 5 is a schematic diagram showing the structure of cultured spherulites;
FIG. 6 shows an optical micrograph of a grown spherulite.
Experiments prove that the side chain branching not only can effectively inhibit planar conformational transition and improve the form stability, but also can improve the solubility and improve the film forming capability, so that PLEDs and organic lasers obtain stable deep blue emission, and the polymer organic photoelectric functional material is a potential polymer organic photoelectric functional material.
While there have been shown and described the fundamental principles and essential features of the invention and advantages thereof, it will be apparent to those skilled in the art that the invention is not limited to the details of the foregoing exemplary embodiments, but is capable of other specific forms without departing from the spirit or essential characteristics thereof; the present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein, and any reference signs in the claims are not intended to be construed as limiting the claim concerned.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. A preparation method of a high-efficiency blue-light polyfluorene spherical crystal material is characterized by comprising the following steps: the preparation method of the high-efficiency blue-light polyfluorene spherical crystal material comprises the following specific preparation steps:
s1: preparation of polymerized monomers:
a: preparing lactone from 2, 7-dibromo-9-fluorenone through Bayer-Virgille rearrangement reaction;
b: preparing 2, 7-dibromodiol from lactone through Grignard reaction;
c: alkyl substitution reaction of 4-position alcohol group of 2, 7-dibromodiol;
d: the main polymer monomer is prepared by Friedel-crafts reaction of the product obtained in the previous step;
s2: preparation of the polymer: taking the same amount of bipyridine and nickel catalyst Ni (COD)2In full of N2The two-neck flask is then activated for 20min in DMF solution at 75 ℃, then added with polymerization monomer solution dissolved by toluene, refluxed for 3 days at 85 ℃, then capped by 0.1ml of dry bromobenzene, finally quenched by THF and hydrazine hydrate, and the silicon-based metal remover is used for removing residual nickel catalyst in the post-treatment process, and then evaporated and settled by absolute methanol, and finally extracted by absolute methanol for 3 days, and then dried in vacuum to obtain a powdery product, namely a polymer;
s3: preparation of polymer spherulites: the polymer in step S2 may be grown into spherulites.
2. The preparation method of the high-efficiency blue-light polyfluorene spherical crystal material according to claim 1, which is characterized by comprising the following steps: the reaction in the step a in the S1 is specifically to react 2, 7-dibromofluorenone for 72 hours at room temperature under the conditions of trifluoroacetic acid and sodium percarbonate.
3. The preparation method of the high-efficiency blue-light polyfluorene spherical crystal material according to claim 1, which is characterized by comprising the following steps: in the step b of S1, 2, 7-dibromolactone reacts with 4-6 times of equivalent of a Grignard reagent of bromobenzene, a solvent is toluene, and the reaction lasts for 24 hours at 85 ℃ under the protection of nitrogen.
4. The preparation method of the high-efficiency blue-light polyfluorene spherical crystal material according to claim 1, which is characterized by comprising the following steps: the c in the S1 is specifically prepared by reacting 2, 7-dibromodiol with 1.5 times of equivalent of 1-bromo-hexylcarbazole in acetone as a solvent for 24 hours at room temperature under an alkaline condition.
5. The preparation method of the high-efficiency blue-light polyfluorene spherical crystal material according to claim 1, which is characterized by comprising the following steps: and d in the S1 is specifically that the product obtained in the previous step is dissolved in anhydrous dichloromethane and reacts for 2 hours under the catalysis of boron trifluoride-diethyl ether to prepare a polymerized monomer.
6. The preparation method of the high-efficiency blue-light polyfluorene spherical crystal material according to claim 1, which is characterized by comprising the following steps: the specific steps of S3 are as follows:
step 1: taking a weighing bottle, putting a bracket in the weighing bottle, and putting a silicon wafer on the bracket;
step 2: taking a proper amount of chloroform solution of the polymer by a pipette, dripping the chloroform solution on a silicon wafer, and sucking the chloroform solution in a proper amount in a weighing bottle by a rubber head dropper;
and step 3: the temperature of the drying oven is set to be 40 ℃, the weighing bottle is carefully placed in the drying oven, the drying oven is closed until the solvent in the weighing bottle is volatilized, and the time is 12 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911388753.3A CN111116871A (en) | 2019-12-30 | 2019-12-30 | Preparation method of efficient blue-light polyfluorene spherical crystal material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911388753.3A CN111116871A (en) | 2019-12-30 | 2019-12-30 | Preparation method of efficient blue-light polyfluorene spherical crystal material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111116871A true CN111116871A (en) | 2020-05-08 |
Family
ID=70504462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911388753.3A Pending CN111116871A (en) | 2019-12-30 | 2019-12-30 | Preparation method of efficient blue-light polyfluorene spherical crystal material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111116871A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115417975A (en) * | 2022-09-19 | 2022-12-02 | 南京工业大学 | Fluorenyl polymer film with spherical crystal structure and preparation method and application thereof |
-
2019
- 2019-12-30 CN CN201911388753.3A patent/CN111116871A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| JIN-YI LIN: "A Rational Molecular Design of β‑Phase Polydiarylfluorenes:Synthesis, Morphology, and Organic Lasers", 《MACROMOLECULES》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115417975A (en) * | 2022-09-19 | 2022-12-02 | 南京工业大学 | Fluorenyl polymer film with spherical crystal structure and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Jin et al. | Poly (fluorenevinylene) derivative by Gilch polymerization for light-emitting diode applications | |
| CN100427441C (en) | Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application | |
| CN107955135B (en) | Conjugated organic lattice nano polymer and preparation and application methods thereof | |
| US11201289B2 (en) | Thermally activated delayed fluorescence polymeric material and preparing method of same | |
| CN101492529B (en) | Soluble polythiophene derivative and application thereof in photoelectric component | |
| CN111116871A (en) | Preparation method of efficient blue-light polyfluorene spherical crystal material | |
| US11512245B2 (en) | Thermally activated delayed fluorescent deep-red light polymer material and method of fabricating same | |
| CN111777542A (en) | Solution-processable thermally-activated delayed fluorescent material and preparation method and application thereof | |
| RU2641103C2 (en) | Polymeric compound and its application in photovoltaic devices | |
| CN111454435B (en) | Phenanthroimidazole unit-based electroluminescent polymer and preparation method and application thereof | |
| EP2730600A1 (en) | Conjugated polymer compound comprising 1,2,3-Benzothiadiazole units and its use in photovoltaic devices | |
| Chen et al. | Germafluorene conjugated copolymer—synthesis and applications in blue-light-emitting diodes and host materials | |
| CN106967056A (en) | The new solution processable 9 of one class, the preparation of 9- diaryl fluorene small molecule emitter materials and photoelectric device | |
| CN112521934B (en) | Hyperbranched electroluminescent polymer, and polymerization monomer, preparation method and application thereof | |
| CN103288811B (en) | Containing dibenzothiophene sulphone organic semiconductor material, its preparation method and organic electroluminescence device | |
| CN109837082A (en) | A kind of electroluminescent material and the preparation method and application thereof | |
| EP2657226B1 (en) | Organic semiconductor material, preparation methods and uses thereof | |
| CN106866939A (en) | The preparation of the diaryl fluorene polymer light sulfate ferroelectric functional material of one class new 9,9 and photoelectric device application | |
| CN107936228B (en) | Electroluminescent polymer and polymerized monomer thereof, preparation method and application | |
| CN110698653A (en) | Side group branched blue-light polymer material, preparation method and application of luminescent device | |
| CN107245037B (en) | Ladder-shaped macromolecule derivative and preparation method and application thereof | |
| CN102807534B (en) | Organic semiconductor material and preparation method thereof | |
| KR101703118B1 (en) | Electron transport material and organic electroluminescent device using thereof | |
| Chao et al. | Effect of Side Chain Alkyl Length on the Electroluminescence Characteristics of Carbazole‐Based Light Emitting Polymers | |
| KR20130058542A (en) | Organic semiconductor compound, organic thin film including the organic semiconductor compound and electronic device including the organic thin film |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200508 |