CN113178539A - Organic electroluminescence circular polarization light-emitting device based on achiral polymer - Google Patents
Organic electroluminescence circular polarization light-emitting device based on achiral polymer Download PDFInfo
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- C—CHEMISTRY; METALLURGY
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- 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
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Abstract
The invention provides an organic electroluminescent circular polarization light-emitting device based on an achiral polymer, which comprises an anode, a hole injection layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially overlapped, wherein the light-emitting layer is made of poly (9, 9-dihexylfluorene-co-benzothiadiazole) induced by circularly polarized light irradiation. The invention provides an OLED which can directly and preferentially emit left-handed or right-handed circularly polarized light based on an achiral polymer (F6 BT); the spiral response of the OLED is easy to control, and is shown not only in handedness of induced circular polarized light but also in wavelength of induced circular polarized light. The OLED provided by the invention provides a simpler and more convenient and efficient design method for realizing circular polarization luminescence of the traditional achiral compound, and lays a foundation for preparing a large-area high-quality chiral micro-nano photoelectric device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent circular polarization light-emitting devices, in particular to an organic electroluminescent circular polarization light-emitting device based on an achiral polymer.
Background
Organic Light Emitting Diodes (OLEDs) have gained scientific and commercial attention due to their unique properties of excellent light emitting properties, high contrast, wide viewing angle \ low power consumption, etc., and are widely used in flat panel display and solid state lighting systems. Circular polarization light emission is becoming the core of a series of display and photonic technologies such as high-efficiency backlight, optical spintronics, quantum information technology and the like. The use of quarter-wave plates, polarizers or beam splitters as passive devices in OLEDs is a typical method of producing circularly polarized light, but it requires the addition of many complex optical components in the optical path, which results in reduced brightness and more complex and bulky device structures. In contrast, the conventional OLED emission layer (EML) can directly generate circularly polarized light through electroluminescence, has the advantages of simplicity, compactness, high efficiency, easy implementation, and the like, and has attracted great interest. Therefore, the study of the connection of chiral side chains to the backbone of non-chiral conjugated polymers, and the study of methods using single chiral small molecule additives to blend with non-chiral luminescent polymers, have become important.
Nevertheless, these methods have several limitations, the former generally requiring extensive custom material synthesis and complex equipment optimization work, and the latter wherein the introduction of chiral additives generally affects the uniformity of the active layer, affecting the emitter performance. The direct implementation of circularly polarized electroluminescence without chiral additives, utilizing the inherent properties of the electroluminescent material, is a simple and effective method, but presents significant challenges.
Circularly polarized light is considered a true chiral species and is also the origin of chirality in biomolecules. Under irradiation of single-chiral circularly polarized light, a large number of enantiomers are produced in a racemic material by asymmetric photochemical reactions including photolysis and photosynthesis. The polyfluorene and the derivatives thereof have the advantages of high fluorescence efficiency, wide forbidden band, excellent thermal stability and chemical stability, easy performance adjustment through substitution and copolymerization and the like, and are the most promising active materials in organic optoelectronic devices.
Disclosure of Invention
The invention solves the technical problem of providing an organic electroluminescent circular polarized light-emitting device which has left-handed or right-handed circularly polarized light.
In view of the above, the present application provides an organic electroluminescent circular polarization light-emitting device based on an achiral polymer, which includes an anode, a hole injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked, where the light-emitting layer is made of poly (9, 9-dihexylfluorene-co-benzothiadiazole) induced by circular polarization illumination.
Preferably, the circularly polarized light is right-handed circularly polarized light with the wavelength of 450-532 nm or left-handed circularly polarized light with the wavelength of 450-532 nm.
Preferably, the induction time of the circularly polarized light is 30-60 min.
Preferably, the light intensity of the induced circular polarized light is 30-100 mW.
Preferably, the thickness of the light-emitting layer is 50-100 nm.
Preferably, the poly (9, 9-dihexylfluorene-co-benzothiadiazole) is prepared by coupling reaction of an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene and an organic halide monomer of 2,1, 3-benzothiadiazole;
the preparation method of the organic boron compound of the 9, 9-dihexyl-2, 7-dibromofluorene comprises the following steps:
reacting 9, 9-dihexyl-2, 7-dibromofluorene and 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane in an organic solvent to obtain an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene;
the preparation method of the organic halide monomer of the 2,1, 3-benzothiadiazole specifically comprises the following steps:
heating and refluxing the 2,1, 3-benzothiadiazole and hydrogen halide, and then adding halogen elements for reaction to obtain the organic halide monomer of the 2,1, 3-benzothiadiazole.
Preferably, the preparation method of the poly (9, 9-dihexylfluorene-co-benzothiadiazole) specifically comprises the following steps:
reacting organic boron compound of 9, 9-dihexyl-2, 7-dibromo fluorene, organic halide monomer of 2,1, 3-benzothiadiazole and tetrakis (triphenylphosphine) palladium in toluene and potassium carbonate to obtain poly (9, 9-dihexyl fluorene-co-benzothiadiazole).
The application provides an organic electroluminescent circular polarization light-emitting device, wherein a light-emitting layer of the organic electroluminescent circular polarization light-emitting device comprises a double-normal-base side group fluorene-benzothiadiazole alternating copolymer F6BT, and circular polarization dichroism of F6BT can be endowed by directly using a circular polarization light induction method under the condition of not using any chiral reagent for doping; based on the results of the impartation of the light-induced circular polarization light emission characteristics, the organic light-emitting diode based on F6BT was designed and prepared, and the electric circular polarization light emission characteristics thereof were imparted using the same method.
Drawings
FIG. 1 is a surface topography of a freshly made F6BT film;
FIG. 2 is the F6BT ultraviolet-visible absorption and photoluminescence spectra;
FIG. 3 is a circular dichroism spectrum of a film sample;
FIG. 4 is a film sample UV-VIS absorption spectrum;
FIG. 5 is a graph of circular dichroism imparting and erasing;
FIG. 6 is a graph of circular dichroism imparting and erasing cycling performance;
FIG. 7 is a graph of the spectra of the samples induced to produce left-handed circularly polarized light at 450nm and 532 nm;
FIG. 8 is a graph of the spectrum of right-handed circularly polarized light produced by the 450nm and 532nm induced samples;
fig. 9 is a schematic diagram of the energy level structure of (a) device and (b) of the organic light emitting diode;
FIG. 10 is a pictorial photograph of an organic light emitting diode;
FIG. 11 is a current density-voltage-luminance graph of the performance of an organic light emitting diode;
FIG. 12 is an emission spectrum at different driving voltages;
FIG. 13 is an electric circularly polarized fluorescence spectrum.
Detailed Description
For a further understanding of the invention, reference will now be made to the preferred embodiments of the invention by way of example, and it is to be understood that the description is intended to further illustrate features and advantages of the invention, and not to limit the scope of the claims.
The embodiment of the invention discloses an organic electroluminescence circular polarization light-emitting device based on an achiral polymer, which comprises an anode, a hole injection layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially overlapped, wherein the light-emitting layer is made of poly (9, 9-dihexylfluorene-co-benzothiadiazole) (F6BT) induced by circularly polarized light.
Under the irradiation of circularly polarized light, the achiral F6BT is converted into a predicted spiral structure, and the influence of the handedness and wavelength of the driving circularly polarized light on the output light can be obtained. In the application, circularly polarized light induced by circularly polarized light of F6BT is specifically rightwise circularly polarized light with the wavelength of 450-532 nm or leftwise circularly polarized light with the wavelength of 450-532 nm; the induction time is 30-60 min, and the light intensity is 30-100 mW.
The poly (9, 9-dihexylfluorene-co-benzothiadiazole) is prepared by coupling reaction of an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene and an organic halide monomer of 2,1, 3-benzothiadiazole;
the preparation method of the organic boron compound of the 9, 9-dihexyl-2, 7-dibromofluorene comprises the following steps:
reacting 9, 9-dihexyl-2, 7-dibromofluorene and 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane in an organic solvent to obtain an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene;
the preparation method of the organic halide monomer of the 2,1, 3-benzothiadiazole specifically comprises the following steps:
heating and refluxing the 2,1, 3-benzothiadiazole and hydrogen halide, and then adding halogen elements for reaction to obtain the organic halide monomer of the 2,1, 3-benzothiadiazole.
The preparation method of the poly (9, 9-dihexylfluorene-co-benzothiadiazole) specifically comprises the following steps:
reacting organic boron compound of 9, 9-dihexyl-2, 7-dibromo fluorene, organic halide monomer of 2,1, 3-benzothiadiazole and tetrakis (triphenylphosphine) palladium in toluene and potassium carbonate to obtain poly (9, 9-dihexyl fluorene-co-benzothiadiazole).
In the application, the light-emitting layer comprises F6BT, and the specific thickness is 50-100 nm; more specifically, the thickness of the F6BT is 60-80 nm.
In the present application, the method for preparing the organic electroluminescent circular polarization light-emitting device is not particularly limited, and the organic electroluminescent circular polarization light-emitting device may be prepared according to a method well known to those skilled in the art.
The achiral F6BT in the absorption layer of the organic electroluminescent material can endow circular dichroism to the organic electroluminescent material only by a circular polarized light irradiation induction method under the condition of not using any chiral reagent for doping, and the endowed circular dichroism signal has good time stability, and no obvious signal attenuation phenomenon is seen even the organic electroluminescent material is continuously placed for 30 days in a dark and light-proof environment; the circularly polarized light dichroism imparting property of F6BT has reversibility: the circular dichroism of the F6BT can be repeatedly endowed and erased by circularly polarized light, and operations such as superposition, offset and inversion of the circular dichroism can be carried out on the basis of original signals of the sample by carefully adjusting illumination induction parameters. The method is simple and effective, has stable and controllable signals, and has wide application prospect in photonics and related fields.
For further understanding of the present invention, the following examples are given to illustrate the performance of the achiral polymer (F6BT) and the organic electroluminescent circular polarization light-emitting device provided by the present invention, and the scope of the present invention is not limited by the following examples.
The apparatus applied in the examples is specifically:
a Bruker Ascend 400MHz nuclear magnetic resonance spectrometer used for characterizing the molecular structure of F6BT and monomers thereof; with CDCl3TMS was used as an internal standard, ppm was used as a chemical shift unit, the number of small molecule scans was 16, and the number of polymer scans was 64.
A Waters 1515-; a chromatography pump model Waters 1515, a differential refractometer detector model Waters 2414. The molecular weight of narrow-distribution polystyrene is used as a standard sample, tetrahydrofuran is used as a mobile phase, the column temperature is 35 ℃, and the flow rate is 1.0mLmin-1。
The Shimadzu UV-2550 ultraviolet-visible spectrophotometer is used for measuring the absorption spectrum of a film sample; in the scanning speed, the absorbance of the test mode, the width of the slit is 1nm, and the sampling interval is 0.1 nm.
Shimadzu RF-5301PC fluorescence spectrophotometer is used for photoluminescence spectrum measurement of film samples.
The Bruker Dimension Icon atomic force microscope is used for surface topography analysis and film thickness measurement of the film sample; the surface morphology uses a Tapping mode, and the film thickness measurement uses a PeakForce mode.
The JASCO J-1500 circular dichroism spectrograph is used for circular dichroism spectrum measurement of the thin film sample; scanning speed of 200nm min-1The test mode was continuous scan with slit width 1nm and sampling interval 0.1 nm.
JASCO CPL-300 circular polarization fluorescence spectrometer is used for measuring circular polarization fluorescence spectrum.
Filmetrics F20-UV optical film thickness measuring instrument is used for measuring the thickness of an organic light-emitting diode functional layer.
The Ambios XP-100 step profiler is used for measuring the thickness of an Al electrode of an organic light emitting diode.
The Topcon SR-UL1R ultra-low brightness spectroradiometer is used for measuring the evaluation indexes of the optical characteristics of the organic light-emitting diode such as brightness, spectrum and the like.
A Keithley 2400 digital source meter for providing drive voltage and current measurements of the organic light emitting diodes.
Example 1
The synthesis method of the organic boride monomer I comprises
Adding 9, 9-dihexyl-2, 7-dibromofluorene (2.03mmol, 1.00g) into a reaction eggplant bottle in a glove box, adding refined tetrahydrofuran (THF, 40mL), sealing, taking out, protecting with inert gas (nitrogen, N2), and placing in a low-temperature constant-temperature tank at-78 ℃ for constant temperature; dropwise adding n-butyllithium/n-hexane solution (n-BuLi, 6.09mmol, 2.4M, 2.54mL) by using a disposable syringe, and continuously stirring at constant temperature for 1 hour after the dropwise addition; 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane (6.09mmol, 1.13g, 1.24mL) was injected in one portion with a single syringe and stirred at a constant temperature for 1 hour; then taking the whole reaction eggplant bottle out of the low-temperature constant-temperature tank, naturally heating, and stirring at room temperature for reaction overnight; adding a small amount of deionized water (10mL) to quench the reaction, removing the solvent by rotary evaporation, dissolving the product by adding dichloromethane (50mL), washing the product with deionized water for three times, drying the product with anhydrous magnesium sulfate, filtering out a drying agent, and removing the solvent by rotary evaporation; performing column chromatography separation and purification on the product by using silica gel as a stationary phase, wherein an eluent is petroleum ether at the temperature of 60-90 ℃ and dichloromethane (1: 1, v: v); removing the eluent by rotary evaporation of the target eluent to finally obtain a white powdery product;
the synthesis method of the organic halide monomer II comprises the following steps
2,1, 3-benzothiadiazole (20mmol, 2.72g) and hydrobromic acid (HBr, 40mmol, 5.43mL) were added to a three-necked flask, heated to reflux, followed by dropwise addition of bromine (Br2, 60mmol, 9.59g, 3.10mL) and reaction for 4 h; quenching reaction by using sodium hydroxide solution (1M, 50mL), extracting by using dichloromethane, drying by using anhydrous magnesium sulfate, filtering out a drying agent, removing a solvent by rotary evaporation, recrystallizing by using methanol, filtering out a liquid, washing by using methanol, and drying in vacuum to finally obtain a white fibrous crystalline product;
the synthesis method of F6BT comprises the following steps:
sequentially adding a monomer I (0.25mmol, 123mg), a monomer II (0.25mmol, 73mg), Toluene (Toluene, 4.5mL), a potassium carbonate aqueous solution (K2CO3, 2M, 2.5mL) and tetrakis (triphenylphosphine) palladium (0)) (Pd (PPh3)4, 5 x 10 < -3 > mmol, 6mg) into a thick-wall pressure-resistant tube, introducing nitrogen to remove oxygen, and carrying out tube sealing reaction at 95 ℃ for 72 hours; the reaction was stopped and the system was cooled to room temperature. Opening a sealed tube, precipitating by using methanol, filtering and drying; and (3) carrying out column chromatography by using neutral alumina as a stationary phase and tetrahydrofuran as an eluent to remove residual catalyst, precipitating again by using methanol, filtering, and drying in vacuum to finally obtain a yellow solid product.
Example 2
Fig. 1 is a surface topography of a film prepared using F6BT, as shown in fig. 1, and atomic force microscopy characterization shows: different concentrations (5, 10, 15 mg. mL)-1) The solution F6 BT/toluene can be respectively spin-coated (3000rpm) to obtain films with different thicknesses (25, 65 and 95nm) but smooth, flat, compact and uniform surfaces, and root mean square deviation (Rq) of the contour<1nm and does not change significantly with film thickness (Δ Rq)<0.25nm), indicating that F6BT has excellent film forming properties.
Normalized UV-visible absorption spectra (Normalized Abs) and Normalized photoluminescence spectra (Normalized PL) of F6BT are shown in FIG. 2; wherein curve 1 represents the absorption spectrum and curve 2 represents the fluorescence spectrum; as can be seen from the figure, the absorption spectrum (Abs) of F6BT covers almost the entire wavelength band from the near ultraviolet region of ultraviolet to the blue-violet region of visible light; the spectrum presents an obvious double-peak shape, the absorption spectrum peak positions are respectively at 320nm and 460nm, and the corresponding full widths at half maximum are respectively 54nm and 104 nm; wherein, the near ultraviolet band with the spectral peak position at 320nm can be attributed to the fluorene (F6) unit, and the blue-violet band with the spectral peak position at 460nm can be attributed to the Benzothiadiazole (BT) unit. The photoluminescence spectrum (PL) has a single peak shape, and mainly covers yellow and green light regions in a visible light region, the peak position of the fluorescence spectrum is 557nm, and the half-peak width is 53 nm. The photoluminescence spectrum covers a much narrower spectral range than the absorption spectrum, with the property of broad absorption and narrow emission. The fluorescence band can be assigned to the BT unit, and the fluorescence band belonging to the F6 unit is completely disappeared, which indicates that there is an efficient fluorescence resonance energy transfer between the F6 unit and the BT unit, and the transfer direction is from the F6 unit to the BT unit.
The circular dichroism endowing characteristics of F6BT circular dichroism and left-right direction dependence of induced circular polarized light are represented by circular dichroism spectrum, as shown in FIG. 3; wherein curve 1 represents the original light, curve 2 represents the left-hand polarized light, and curve 3 represents the right-hand polarized light; the results show that the new sample (Pristine) does not have any signal except the noise of the instrument itself in the wavelength range of 300-700 nm corresponding to the absorption of F6BT, indicating that the new sample does not have circular dichroism. Samples (L-CPL and R-CPL) induced by circularly polarized light irradiation (450nm, 30mW and 30min) show S-type characteristic spectral lines, the position of a spectral peak is about 485nm, the intensity of the spectral peak is 7.68mdeg, and a circular dichroism asymmetry factor | g _ CD | -, 7.46 multiplied by 10-4And has a clear circular dichroism signal, indicating that F6BT has a circular dichroism imparting property of circularly polarized light. Meanwhile, the circular dichroism spectrum of the right-handed circular polarized light irradiation induced sample (R-CPL) undergoes a positive-negative curve transformation process from long wavelength to short wavelength, and a remarkable negative Koton (Cotton) effect is shown, which indicates that the F6BT main chain(ii) a conformational surplus of the P helix; the samples induced by left-handed circular polarization illumination (L-CPL) exhibited a positive koton effect, which is exactly opposite to that of the right-handed circular polarization illumination-induced samples, indicating the excess of the M-helical conformation of the backbone of F6 BT. The samples induced by the left-handed and right-handed circular polarized lights respectively show completely opposite Keton effects, which shows that the circular polarized light dichroism endowing property of F6BT has the left-handed and right-handed direction dependence of induced circular polarized light.
The uv-vis absorption trace results show that, as shown in fig. 4, curves 1, 2, 3 represent the original light, the left-hand polarized light and the right-hand polarized light, respectively; as can be seen, the absorption spectra of the circularly polarized light irradiation induced samples (L-CPL and R-CPL) and the freshly prepared sample (Pristine) overlap well, indicating that the absorption of F6BT is not significantly changed by circularly polarized light irradiation induction; and the absorption spectra of the samples induced by the left-handed circularly polarized light and the right-handed circularly polarized light respectively are well overlapped, which shows that the absorption of the F6BT is not changed along with the change of the left-handed direction and the right-handed direction of the induced circularly polarized light.
The circular dichroism of example 3F6BT can be imparted not only by circularly polarized light but also erased by the same method
FIG. 5 shows the circular dichroism imparting and erasing curve characteristics of F6BT, where sample i with right-handed circular polarized illumination (450nm, 30mW) for 30min followed by left-handed circular polarized illumination (450nm, 30mW, 30min) for the same time period results in substantial disappearance of the circular dichroism signal of sample ii, and the subsequent right-handed circular polarized illumination (450nm, 30mW, 30min) for the same time period results in the return of the circular dichroism signal of sample iii to that of sample i. On the other hand, samples i, ii and iv are represented by curves 1, 2 and 3 in the figure, respectively; the left-handed circular polarized illumination (450nm, 30mW, 30min) followed at the same time on the basis of sample ii allows sample iv to assume the opposite signal state to that of sample i. The above results indicate that the circular dichroism of F6BT can be imparted not only by circularly polarized light but also erased by circularly polarized light, and that the subsequent light induction is added or cancelled based on the original signal of the sample, and that the circular dichroism imparting reversibility is exhibited.
By repeatedly switching the left-right rotation direction of the light-induced circularly polarized light, it is possible to realize a cycle of F6BT circular dichroism imparting and erasing. Specifically, based on the above samples i, ii and iv, 450nm right-handed circularly polarized light is further used to induce (450nm, 30mW) for 30min and 60min respectively to finally reach the circular dichroism signal state equivalent to that of the sample i, and then the cycle experiment is performed by taking the complete cycle and adopting the same circularly polarized light according to the induction flow. As a result, as shown in fig. 6, the circularly polarized circular dichroism imparting property of F6BT has good reversibility, and circular dichroism can be imparted, erased and reversed repeatedly by circularly polarized light. However, due to the memory effect, the signal intensity of the spectral peaks (green and blue) taken around 485nm is gradually attenuated and cannot be fully restored to the previous level, so that the improvement of the cycle performance needs to further optimize the light induction parameters on the basis of the gradual attenuation.
Example 4 circular dichroism imparted to F6BT by circularly polarized light is not only related to the left-right direction of induced circularly polarized light, but also to the wavelength thereof
Under the induction of left-handed circularly polarized light, if the wavelength of the induced light is 450nm, the induced sample will exhibit a positive coriolis effect as described above, but if the wavelength of the induced light is adjusted to 532nm, as shown in fig. 7, the completely opposite negative coriolis effect will be exhibited, wherein curve 1 represents the induced light of 450nm and curve 2 represents the induced light of 532 nm; for right-handed circularly polarized light induced samples, as shown in FIG. 8, when the induced light wavelength is adjusted from 450nm to 532nm, the circular dichroism spectrum is also reversed accordingly, wherein curve 1 represents the induced light at 450nm and curve 2 represents the induced light at 532 nm. On the other hand, in the circular dichroism imparting effect, the 450nm left-handed circularly polarized light and the 532nm right-handed circularly polarized light, and the 450nm right-handed circularly polarized light and the 532nm left-handed circularly polarized light are the same, and it is described that the same circular dichroism imparting effect can be achieved by adjusting the wavelength and the left-right direction of the light-induced circularly polarized light simultaneously, and the circular dichroism of F6BT imparts the left-right direction dependence and the wavelength dependence of the induced light independently from each other without interfering with each other.
Example 5
The structure of the organic light emitting diode device adopts [ ITO (185nm)/PEDOT: PSS (40nm)/F6BT (65nm)/TPBi (50nm)/LiF (1nm)/Al (100nm) ], and the structure of the device and the structure of the energy level are shown in figure 9. Wherein ITO and Al are used as anode and cathode materials, PEDOT, PSS and LiF are used as Hole Injection Layer (HIL) and Electron Injection Layer (EIL) materials, and TPBi and F6BT are used as Electron Transport Layer (ETL) and light-emitting layer (EML) materials. The resulting device is shown in fig. 10, in which (a) the light-emitting regions are indicated by the dotted line boxes, 8 light-emitting regions each having an area of 3 × 3mm2 are simultaneously formed on each substrate, and (b) shows a state in which the light-emitting regions are lit.
The performance of the freshly prepared OLED is shown in FIG. 11, where curve 1 represents the current density and curve 2 represents the fluorescence intensity. Starting voltage 4.2V, maximum luminance 1893cd m-2Maximum current efficiency of 0.32 cd. A-1The maximum external quantum efficiency is 0.11%. The organic light emitting diode emits obvious yellow fluorescence in the whole driving voltage range, the peak position of the fluorescence spectrum is 555nm, the corresponding CIE 1931 color coordinate (0.43, 0.53) is well matched with the photoluminescence result of F6BT, the high efficiency of exciton recombination in the electroluminescent process is illustrated, and the spectrum and the color coordinate with almost unchanged driving voltage from 5V to 8V illustrate that the electroluminescent is not interfered by the voltage change, as shown in FIG. 12.
As shown in fig. 13, curve 1 represents left-handed circular polarization and curve 2 represents right-handed circular polarization. The induced device has obvious electric circular polarization fluorescence signal, and the | g _ EL | at 554nm is 4.16 multiplied by 10-3And the circularly polarized light irradiation inducing devices with different left and right rotation directions present completely opposite electrically-induced circularly polarized fluorescence signals with different intensities, and are consistent with the photoinduced circularly polarized result.
In conclusion, the invention utilizes the excellent photoelectric properties of polyfluorene and derivatives thereof, and selects the achiral main chain conjugated polymer poly (9, 9-dihexylfluorene-co-benzothiazole) (F6BT) as a substrate for generating circularly polarized light. Under the irradiation of circularly polarized light, achiral F6BT can be converted into a predicted helical structure, and the influence of handedness and wavelength of the driving circularly polarized light on the output light can be obtained. The invention has good time stability and reversibility, is simple and effective, has stable and controllable signals, and has wide application prospect in photonics and related fields.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (7)
1. An organic electroluminescence circular polarization light emitting device based on an achiral polymer comprises an anode, a hole injection layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially overlapped, and is characterized in that the light emitting layer is made of poly (9, 9-dihexylfluorene-co-benzothiadiazole) induced by circularly polarized light irradiation.
2. The organic electroluminescent circular polarization light-emitting device according to claim 1, wherein the circularly polarized light is a right-handed circularly polarized light having a wavelength of 450 to 532nm or a left-handed circularly polarized light having a wavelength of 450 to 532 nm.
3. The organic electroluminescent circular polarization light-emitting device according to claim 1, wherein the induction time of the circularly polarized light is 30 to 60 min.
4. The organic electroluminescent circular polarization light-emitting device according to claim 1, wherein the intensity of the induced circular polarized light is 30 to 100 mW.
5. The organic electroluminescent circular polarization light-emitting device according to claim 1, wherein the thickness of the light-emitting layer is 50 to 100 nm.
6. The organic electroluminescent circular polarization light-emitting device according to claim 1, wherein the poly (9, 9-dihexylfluorene-co-benzothiadiazole) is prepared by coupling reaction of an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene and an organic halide monomer of 2,1, 3-benzothiadiazole;
the preparation method of the organic boron compound of the 9, 9-dihexyl-2, 7-dibromofluorene comprises the following steps:
reacting 9, 9-dihexyl-2, 7-dibromofluorene and 2-isopropoxy-4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborane in an organic solvent to obtain an organic boron compound of 9, 9-dihexyl-2, 7-dibromofluorene;
the preparation method of the organic halide monomer of the 2,1, 3-benzothiadiazole specifically comprises the following steps:
heating and refluxing the 2,1, 3-benzothiadiazole and hydrogen halide, and then adding halogen elements for reaction to obtain the organic halide monomer of the 2,1, 3-benzothiadiazole.
7. The organic electroluminescent circular polarization light-emitting device according to claim 6, wherein the preparation method of the poly (9, 9-dihexylfluorene-co-benzothiadiazole) specifically comprises:
reacting organic boron compound of 9, 9-dihexyl-2, 7-dibromo fluorene, organic halide monomer of 2,1, 3-benzothiadiazole and tetrakis (triphenylphosphine) palladium in toluene and potassium carbonate to obtain poly (9, 9-dihexyl fluorene-co-benzothiadiazole).
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