CN110760301A - Siloxane organic fluorescent powder and preparation method thereof - Google Patents
Siloxane organic fluorescent powder and preparation method thereof Download PDFInfo
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Abstract
The invention provides a siloxane organic fluorescent powder which is an environment-friendly pollution-free material, is easy to manufacture, and has high conversion efficiency, high color rendering property, wide color temperature range and excellent photoelectric property.
Description
Technical Field
The invention relates to an organic luminescent material, in particular to a preparation method and application of siloxane organic fluorescent powder.
Background
Phosphors generate fluorescence by electron transition. When the phosphor is stimulated by light, electrons in the phosphor are stimulated to an excited state of a high energy level and then return to an original state of a low energy level, and energy is radiated in the form of light.
So far, white light emitting diodes still mainly use blue light emitting diodes to excite yellow (inorganic) phosphor, such as YAG (yttrium aluminum garnet) phosphor in combination with blue light emitting diodes. Although the white light emitting diode manufactured in the way has higher luminous efficiency, the light emitted by the element is mostly cold white light with high color temperature and contains a large amount of blue light; besides, the color rendering property is low due to lack of red light wave band, and the health of human body is not benefited. In addition, most of the white light emitting diodes on the market use fluorescent materials doped with rare earth elements. Rare earth elements are expensive and not environmentally friendly. Moreover, the manufacturing method of the fluorescent powder adopts solid-state sintering (solid-state sintering), the temperature of the manufacturing process is higher than 1000 ℃, and hydrogen is required to be introduced to reduce rare earth elements, so that the manufacturing cost and the danger are high.
Taiwan patent application No. 102112135, filed 2013, 4/3, entitled "method for producing zinc sulfide nanoparticles doped with metal ions and method for performing photo-induced warming white light using the same", discloses a method for producing manganese-doped zinc sulfide nanoparticles (or quantum dots) by a solution method, which is used to replace the conventional fluorescent material doped with rare earth elements. However, the optimal absorption wavelength of manganese-doped zinc sulfide nanoparticles is at the uv wavelength (i.e., wavelength <400 nanometers (nm)), which has limited application.
In addition, manganese-doped ZnSe nanoparticles (ZnSe: Mn) have been developed in recent years to replace the conventional rare earth fluorescent materials. The synthesis method of the nano-particles is mostly nucleation doping, and metal organic compounds are used as the source of metal ions. In the nucleation doping process, the manganese ion precursor solution is injected into the selenium ion precursor solution, which is generally toxic, not environmentally friendly and expensive. In addition, the nucleation doping method requires two-stage growth of manganese selenide (MnSe) and zinc selenide (ZnSe), growth at a high temperature of about 300 ℃, the manufacturing process is difficult, and the prepared manganese-doped zinc selenide nanoparticles have poor dispersibility, resulting in poor luminous efficiency. In addition, the optimum absorption wavelength is in the ultraviolet band, and the application is limited.
Taiwan patent application No. 104104303, filed on 2015, 2/9, entitled "method for producing rare earth-free fluorescent material with strongest absorption wavelength between 410 nm and 470nm and method for photo-induced white light emission using the same", relates to a method for producing manganese-doped zinc selenide nanoparticles excited by blue light (440 + 470 nm) to emit yellow orange light with wavelength of 500 + 700 nm by using cheap and environment-friendly materials and by a simple and low-cost method. Furthermore, the non-rare earth fluorescent material and the organic material which is excited by blue light and emits green light or orange light are used for manufacturing white light fluorescent solution or white light fluorescent film, and white light which is suitable for daily illumination, has low color temperature and does not harm human bodies can be generated.
On the other hand, the prior art also uses organic fluorescent powder to manufacture white light diode devices. For example, two studies were conducted in a thesis published in 2008 as kitigenin at university success, namely "the application of organic phosphor C545P to packaging of white light emitting diodes": 1, a white light diode element for exciting C545P organic fluorescent powder by an ultraviolet light diode (380 nm); 2, a white light diode element in which a red/C545P mixed phosphor is excited with a blue diode (460 nm). The two methods can obtain the white light diode element with high color rendering and luminescence.
The stability of fluorescent materials applied to Light Emitting Diodes (LEDs) is usually considered in terms of environmental stability and thermal stability. However, the white light diode element made of organic fluorescent powder can not meet the requirements in these characteristics, and can not be applied in industry in practice. There is still a need in the industry to develop a new fluorescent material that meets the requirements of environmental protection, easy manufacturing process, high conversion efficiency (energy-conversion efficiency), high color rendering, wide color temperature range, good reliability and photoelectric properties.
Disclosure of Invention
The invention relates to a preparation method and application of siloxane organic fluorescent powder.
According to an embodiment of the present invention, a siloxane organic phosphor includes an organic dye, a siloxane compound, and an organic layer. The organic dye can absorb the short-wavelength excitation light and then emit the emission light with long wavelength. The siloxane bonds to the organic layer, which bonds to the organic dye. Therefore, the organic layer promotes the luminous efficiency of the organic dye, and the siloxane compound isolates the external environment.
The silicone organic phosphor, wherein the siloxAne compound comprises siloxAne (siloxAne), silicA (silicaa) or other polymers containing silane groups.
In the above siloxane organic phosphor, a structure of the siloxane bonded to the organic layer includes silicon alkoxide (siloxide).
In the siloxane organic phosphor, the structure of the siloxane compound bonded to the organic layer includes tetramethyldisiloxane, hexamethyldisiloxane, hexamethylcyclotrisiloxane, or tetramethylcyclotetrasiloxane.
The siloxane organic phosphor, wherein the structure of the siloxane bonded to the organic layer comprises one or more of the following functional groups: hydrosilyl (Si-H), silyl (Si-R), siloxy (Si-O).
The aforementioned silicone organic phosphor, wherein the siloxane compound comprises the structure:
the silicone organic phosphor, wherein the organic dye comprises at least one of the following functional groups: ester, Nitrile.
The silicone organic phosphor, wherein the organic dye comprises C545T, C545P, Alq3, BA-NPB, TPA, DCJTB, DCQTB, PtOEP, Ir (dpm) (piq)2, or Ru (dtb-bpy)3 (PF 6).
According to another embodiment of the present invention, a method for manufacturing a siloxane organic phosphor comprises the steps of: drying the polymer solution of the siloxane compound to form polymer powder of the siloxane compound, wherein the polymer of the siloxane compound is bonded with the organic layer; dissolving a polymer powder of the siloxane compound and an organic base powder in a solvent to form a first solution; dissolving organic dye powder in the first solution; removing the solvent in the first solution to form a solid, and grinding the solid to form the siloxane organic fluorescent powder.
The method for producing a siloxane organic phosphor, wherein the organic base powder comprises: sodium methoxide, potassium ethoxide, potassium tert-butoxide, butyl lithium, phenyl lithium, or an organic compound containing an amino group in the molecule.
According to the siloxane organic fluorescent powder provided by the embodiment of the invention, the siloxane compound can isolate the environment and increase the powder volume so as to improve the dispersibility of the organic dye, the organic layer can improve the photoelectric characteristic and reliability of the prepared siloxane organic fluorescent powder, and the conversion efficiency of the prepared siloxane organic fluorescent powder is at least higher than 90%.
According to another embodiment of the present invention, a siloxane organic phosphor comprises a first organic dye and a second organic dye. The first organic dye can absorb the blue excitation light and then emit green light. The second organic dye can absorb the blue excitation light and then emit red light. Wherein the first organic dye and the second organic dye are respectively bonded with the organic layer, and the organic layer is bonded with the siloxane compound. Therefore, after being excited by blue light, the siloxane organic fluorescent powder can emit warm white light with the color rendering property higher than 95 and the wide color temperature range of 2500K-4000K.
Drawings
FIG. 1 is a flow chart showing a method for preparing a siloxane organic phosphor according to one embodiment of the present invention.
Fig. 2 shows a structure of a siloxane compound according to an embodiment of the invention.
Fig. 3 and 4 are a raman spectrum and a fourier transform infrared spectroscopy (FTIR) spectrum of a siloxane after surface modification of a bonded organic layer according to an embodiment of the present invention.
FIG. 5 shows the PL excitation spectrum (left) and the PL emission spectrum (right) of the silicone organic phosphor prepared in example 1 and a comparative sample.
FIG. 6 shows the PL excitation spectrum (left) and the PL emission spectrum (right) of the silicone organic phosphor prepared in example 2 and a comparative sample.
FIG. 7 shows the PL excitation spectrum (left) and the PL emission spectrum (right) of the silicone organic phosphor prepared in example 3 and a comparative sample.
FIG. 8A shows the PL emission spectrum of a warm white-emitting silicone organic phosphor prepared in example 4.
FIG. 8B shows a color coordinate plot of a warm white-emitting silicone organic phosphor prepared in example 4.
FIG. 9 shows the photoelectric property test results of the siloxane organic fluorescent powder and the comparative sample.
[ description of main element symbols ]
10-14: preparation method of siloxane organic fluorescent powder
Detailed Description
The following detailed description of the embodiments of the present disclosure will be given with reference to the accompanying drawings. Aside from the detailed description, this invention is capable of general implementation in other embodiments and its several details are capable of modifications in various obvious respects, all without departing from the scope of the present application, and all such modifications and equivalents are intended to be encompassed within the claims appended hereto. In the description of the specification, numerous specific details are set forth in order to provide a more thorough understanding of the invention; however, the present invention may be practiced without some or all of these specific details. In other instances, well known process steps or elements have not been described in detail in order to not unnecessarily obscure the present invention.
The embodiment of the invention discloses siloxane organic fluorescent powder, which comprises an organic dye, a siloxane compound and an organic layer. The organic dye can absorb the short-wavelength excitation light and then emit the emission light with long wavelength. The surface of the siloxane compound is modified to bond with the organic layer, and the organic layer and the organic dye generate bonding or chemical reaction. Therefore, the organic layer promotes the luminous efficiency of the organic dye, and the siloxane compound isolates the external environment.
In some embodiments, the siloxane compound comprises siloxane (siloxane), silica (silica), or the like, or other silane-containing polymer.
In one embodiment, the structure of the modified siloxane-bonded organic layer comprises a silicon alkoxide (siloxide) having the formula R3SiOM, wherein R is an organic group and M is a metal.
In some embodiments, the structure of the modified siloxane-bonded organic layer comprises one or more of the following functional groups: hydrosilyl (Si-H), silyl (Si-R), siloxy (Si-O).
In some embodiments, the structure of the modified siloxane bonded organic layer comprises tetramethyldisiloxane (tetramethylradisiloxane), hexamethyldisiloxane, hexamethylcyclotrisiloxane, tetramethylcyclotetrasiloxane.
In one embodiment, the siloxane comprises a structure as shown in fig. 2.
In some embodiments, the organic dye comprises at least one of the following functional groups: ester, Nitrile.
According to the embodiment of the invention, the organic dye can absorb the short-wavelength excitation light and then emit the long-wavelength emission light, and different types of organic dyes are selected according to the required emission light color. For example, the organic dye for emitting green light may be selected from one or a combination of the following groups: C545T, C545P, Alq3, BA-NPB and TPA. The organic dye for emitting red light may be selected from one or a combination of the following groups DCJTB, DCQTB (C)28H31N3O)、PtOEP、Ir(dpm)(piq)2、Ru(dtb-bpy)3·2(PF6)。
The organic dye C545T has the Chinese name of 2-tert-butyl-4- (dicyanomethylene) -6- [2- (1,1,7,7-tetramethyljulolidin-9-yl) ethenyl]-4H-pyran, the english name 2-tert-Butyl-4- (dicyclomethylene) -6- [2- (1,1,7, 7-tetramethyljunolidin-9-yl) vinyl]-4H-pyran of formula C26H26N2O2And S. Alq3 is named as aluminum 8-hydroxyquinoline in Chinese, as Tris (8-quinolato) aluminum (III) in English, and has the chemical formula C27H18AlN3O3. The Chinese name of BA-NPB is N, N ' -di-1-naphthyl-N, N ' -diphenyl- [9,9' -bianthracene]10,10' -diamine with the English name N10, N10' -diphenylene-N10, N10' -dinaphhthalenyl-9, 9' -bianthracene-10,10' -diamine and the chemical formula C60H40N2. TPA is called triphenylamine in the name of Chinese, triphenylamine in the name of English, and has the chemical formula C18H15And N is added. DCJTB is referred to herein as 2-tert-butyl-4- (dicyanomethylene) -6- [2- (1,1,7,7-tetramethyljulolidin-9-yl) ethenyl]-4H-pyran, the english name 2-tert-Butyl-4- (dicyclomethylene) -6- [2- (1,1,7,7-tetramethyljulol idin-9-yl) vinyl]-4H-pyran，C30H36N3And O. Chemical formula of DCQTB is C28H31N3And O. The Chinese name of PtOEP is octaethylporphyrin platinum with the chemical formula C36H44N4And (3) Pt. Ir (dpm) (piq)2 of the formula C41H39IrN2O2. RU (DTB-BPY) 3.2 (PF6) has a chemical formula of C54H72F12N6P2Ru。
FIG. 1 is a flow chart showing a method of manufacturing a silicone organic phosphor according to the foregoing embodiment of the present invention. Referring to fig. 1, step 10, a polymer solution of siloxane compound is dried to form a polymer powder of siloxane compound, wherein the polymer of siloxane compound is surface modified and bonded to an organic layer. For example, the polymer solution of siloxane compound is placed in a vacuum oven and baked at a temperature of 150 to 180 ℃ for about 1 to 3 hours to form a polymer powder of siloxane compound including an organic layer.
As shown in fig. 1, in step 11, the polymer powder of the siloxane compound and the organic base powder are dissolved in a solvent to form a first solution. The solvent may include, but is not limited to, polar or non-polar solvents such as n-hexane, cyclohexanone, ethyl acetate, acetone, methanol, ethanol, isopropanol, tetrahydrofuran, and the like. An ultrasonic shaker may be used to accelerate the dissolution process. The organic base can balance the acidity of the polymer of siloxane compounds and improve the environmental stability, thermal stability and reliability of the prepared siloxane organic fluorescent powder. The organic base may include, but is not limited to: sodium methoxide, potassium ethoxide, potassium tert-butoxide, butyl lithium, phenyl lithium, or an organic compound containing an amino group in its molecule.
As shown in fig. 1, in step 12, an organic dye powder is dissolved in the first solution. As described above, the organic dye and the solvent capable of dissolving the organic dye and the polymer of the siloxane compound are suitably selected according to the emission wavelength band to be emitted. An ultrasonic shaker may be used to accelerate the dissolution process.
As shown in fig. 1, at step 13, the solvent in the first solution is removed to form a solid, and the solid is ground to form the siloxane organic phosphor. For example, the first solution is placed in a vacuum oven and baked at 100-180 ℃ for about 3-5 hours, and then ground into the siloxane organic fluorescent powder by a grinder after curing.
Fig. 3 and 4 are a raman spectrum and a fourier transform infrared spectroscopy (FTIR) spectrum of a siloxane after surface modification of a bonded organic layer according to an embodiment of the present invention. From the above-mentioned figures and experimental results, it is known that the Ester (Ester) RCOOR functional group of the organic dye reacts with the silicon oxide (Si — O) functional group of the modified siloxane compound to convert into the silicon-based Ester (Silyl Ester) RCOOSiR functional group of the siloxane organic phosphor.
Example 1
In this example, the organic dye is C545T, and the Siloxane (Siloxane) shown in FIG. 2 is used to prepare the organic phosphor according to the method shown in FIG. 1. FIG. 5 shows the PL excitation spectrum (left) and the PL emission spectrum (right), i.e., the absorption spectrum, of the silicone organic phosphor prepared in example 1. The PL excitation spectrum (left) and the PL emission spectrum (right) of the simple organic dye C545T were also placed for comparison. As shown in FIG. 5, the optimal excitation range of the silicone organic phosphor prepared in example 1 is 440-470nm (the light emission range of a commercial blue LED), and the emission wavelength is 500-530 nm. The conversion efficiency of the green-emitting siloxane organic fluorescent powder is higher than 95%, and the luminous efficiency of the green-emitting siloxane organic fluorescent powder is superior to that of organic dye C545T.
Example 2
In this example, the organic dye is DCJTB, and a Siloxane compound (Siloxane) as shown in FIG. 2 is used to form a Siloxane organic phosphor as shown in FIG. 1. FIG. 6 shows the PL excitation spectrum (left) and the PL emission spectrum (right) of the silicone organic phosphor prepared in example 2. The PL excitation spectrum (left) and the PL emission spectrum (right) of the simple organic dye DCJTB were also placed for comparison. As shown in FIG. 6, the optimal excitation range of the silicone organic phosphor prepared in example 2 is 440-470nm (the light emission range of a commercial blue LED), and the emission wavelength is 600-630 nm. The conversion efficiency of the red-light-emitting siloxane organic fluorescent powder is higher than 90%, and the luminous efficiency of the red-light-emitting siloxane organic fluorescent powder is superior to that of organic dye DCJTB.
Example 3
In this example, the organic dye is TPA, and Siloxane (Siloxane) as shown in FIG. 2 is used to prepare the Siloxane organic phosphor as shown in FIG. 1. FIG. 7 shows the PL excitation spectrum (left) and the PL luminescence spectrum (right) of the silicone organic phosphor prepared in example 3. The PL excitation spectrum (left) and the PL emission spectrum (right) of the simple organic dye TPA were simultaneously placed for comparison. As shown in FIG. 7, the optimal excitation range of the silicone organic phosphor prepared in example 3 is 440-470nm (the light emission range of a commercial blue LED), and the light emission wavelength is 500-530 nm. The conversion efficiency of the green-emitting siloxane organic fluorescent powder is higher than 90%, and the luminous efficiency of the green-emitting siloxane organic fluorescent powder is superior to that of organic dye TPA.
Example 4 (application)
The siloxane organic fluorescent powder emitting green light prepared in example 1 and the siloxane organic fluorescent powder emitting red light prepared in example 2 are doped in a lens or coated on a substrate, and then a blue light LED emitting light with the wavelength of 440-470nm is used as an excitation light source, so that white light with the color rendering property higher than 95% can be obtained, and the conversion efficiency is higher than 90%. The mixing ratio of the green-light siloxane organic fluorescent powder to the red-light siloxane organic fluorescent powder is 1: 1-1: 3.4 (unit: g), and the siloxane organic fluorescent powder which has the color temperature range of 2500K-4000K and emits warm white light can be obtained.
FIG. 8A shows the PL emission spectrum of a warm white-emitting silicone organic phosphor prepared in example 4, in which the green-emitting silicone organic phosphor and the red-emitting silicone organic phosphor were mixed at a ratio of 1:3.4, and the wavelength of the excitation light was 450 nm. FIG. 8B shows the CIE-1931(X:0.4691, Y0.4735) color coordinate diagram of the warm white-emitting silicone organic phosphor prepared in example 4. (Green light siloxane organic fluorescent powder and red light siloxane organic fluorescent powder mixing ratio is 1: 3.4; color temperature: 3000K)
Characteristics of
According to the embodiment of the invention, the siloxane organic fluorescent powder is synthesized by using the surface modified siloxane compound, so that the dispersibility of the organic dye is increased, and the prepared siloxane organic fluorescent powder has good luminous efficiency.
According to the embodiment of the invention, the siloxane compound bonded organic layer can effectively improve the photoelectric characteristics and the reliability of the prepared siloxane organic fluorescent powder. FIG. 9 shows the excitation spectrum and emission spectrum of a siloxane organic phosphor prepared from a conventional SOG silicon oxide (without an organic layer) and the siloxane compound with an organic layer. As shown in FIG. 9, the number of emitted photons (5638) of the silicone organic phosphor was increased by at least 70% compared to the number of emitted photons (17937) of the organic phosphor made of a conventional SOG silicon oxide (without organic layer). The result proves that the siloxane organic fluorescent powder prepared by modifying and bonding the siloxane compound of the organic layer can greatly improve the luminous efficiency of the siloxane organic fluorescent powder.
In addition, the novel siloxane organic fluorescent powder has high conversion efficiency, high color rendering property, good reliability, wide color temperature range and good thermal stability, and can make up the problems of insufficient color rendering property (for example, the color rendering property of YAG: Ce yellow fluorescent powder is only about 70), difficult color temperature adjustment, lack of partial light-emitting waveband and the like (for example, the light-emitting wavelength of β -SiAlON: Eu green fluorescent powder is 540-.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (11)
1. A silicone organic phosphor, comprising:
an organic dye which absorbs the short-wavelength excitation light and emits the long-wavelength emission light;
a siloxane compound; and
an organic layer, wherein the siloxane bonds to the organic layer, the organic layer bonds to the organic dye;
therefore, the organic layer promotes the luminous efficiency of the organic dye, and the siloxane compound isolates the external environment.
2. The silicone organic phosphor of claim 1, wherein: wherein the siloxane compound comprises siloxane, silica, or other silane-containing polymer.
3. The silicone organic phosphor of claim 1, wherein: wherein the structure of the siloxane bonded to the organic layer comprises a silicon alkoxide.
4. The silicone organic phosphor of claim 1, wherein: wherein the structure of the siloxane bonded to the organic layer comprises tetramethyldisiloxane, hexamethyldisiloxane, hexamethylcyclotrisiloxane, or tetramethylcyclotetrasiloxane.
5. The silicone organic phosphor of claim 1, wherein: wherein the structure of the siloxane bond to the organic layer comprises one or more of the following functional groups: hydrosilyl (Si-H), silyl (Si-R), siloxy (Si-O).
6. The silicone organic phosphor of claim 1, wherein: wherein the siloxane comprises the structure:
7. the silicone organic phosphor of claim 1, wherein: wherein the organic dye comprises at least one of the following functional groups: esters, nitriles.
8. The silicone organic phosphor of claim 1, wherein: wherein the organic dye comprises C545T, C545P, Alq3, BA-NPB, TPA, DCJTB, DCQTB, PtOEP, Ir (dpm) (piq)2, or Ru (dtb-bpy)3.(PF 6).
9. A method for preparing siloxane organic fluorescent powder is characterized by comprising the following steps:
drying the polymer solution of the siloxane compound to form polymer powder of the siloxane compound, wherein the polymer of the siloxane compound is bonded with the organic layer;
dissolving a polymer powder of the siloxane compound and an organic base powder in a solvent to form a first solution;
dissolving organic dye powder in the first solution;
removing the solvent in the first solution to form a solid, and grinding the solid to form the siloxane organic fluorescent powder.
10. The method for producing a silicone organic phosphor according to claim 9, characterized in that: wherein the organic base powder comprises: sodium methoxide, potassium ethoxide, potassium tert-butoxide, butyl lithium, phenyl lithium, or an organic compound containing an amino group in the molecule.
11. A silicone organic phosphor, comprising:
the first organic dye can absorb blue excitation light and then emit green light;
the second organic dye can absorb the blue excitation light and then emit red light;
wherein the first organic dye and the second organic dye are respectively bonded with an organic layer, and the organic layer is bonded with a siloxane compound;
therefore, after being excited by blue light, the siloxane organic fluorescent powder can emit white light with the color temperature ranging from 2500K to 4000K.
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