CN104073247A - Side-chain aryl conjugated organic light-emitting material and preparation method thereof - Google Patents
Side-chain aryl conjugated organic light-emitting material and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a side-chain aryl conjugated organic light-emitting material and a preparation method thereof and relates to an organic light-emitting material. The preparation method comprises the steps of synthesizing polycarbosilane; removing polycarbosilane small molecule; and synthesizing side chain aryl conjugated polycarbosilane. The method specifically comprises the steps of reacting poly(dimethylsiloxane) as a raw material in a high pressure reaction kettle to obtain polycarbosilane, then defoaming polycarbosilane small molecules, and then reacting a small amount of aryl (Pn) organic matters and defoamed polycarbosilane to obtain the solid side-chain aryl conjugated polycarbosilane. The antioxidant crosslinking performance, anti-ultraviolet aging performance and thermal stability are improved. Although the reacted system has a conjugated structure, no rigid planar structure and is lack of an electron donating group, the reaction system still shows relatively strong luminescent performance. After a synthesized product is excited by ultraviolet light of which the wavelength is 350nm, the synthesized product has blue-violet light emission at 410nm, the emission purity is high, no miscellaneous peak is generated and good antioxidant crosslinking performance, anti-ultraviolet aging performance and thermal stability are achieved.
Description
Technical field
The present invention relates to luminous organic material, especially relate to a kind of side chain aryl conjugation luminous organic material and preparation method thereof.
Background technology
Luminescent material is applied in the historical long river of human civilization from start to finish, and it is widely used in the high-tech areas such as communication, satellite, radar, demonstration, record, optical computer and probe biomolecule.Particularly entered today of information age, met various information and show that the Development of Photo And Cathodoluminescent Materials of demand is particularly rapid.Luminescent material can be divided into phosphor and the large class of luminous organic material two.Compare with inorganic materials, organic materials has higher luminous efficiency and wider glow color range of choice, and has the superiority of easy big area film forming.In recent years, about the research of luminous organic material, more and more cause people's interest.
Photoluminescence is a kind of quite important and general phenomenon, and the research that inorganics is luminous and application have had longer history, but the shortcoming that phosphor exists some to be difficult to overcome: kind is few, controllability is little, working conditions is harsh, and energy efficiency is not high, is difficult to obtain blue light etc.Therefore it will be very important exploring new luminescent material.There is the organic molecule of large conjugated system under the exciting of electricity or light, easily produce the transition of electronic level, send the light of different wave length.Of a great variety due to organic compound, structure is varied, can meet various purposes, and in luminous field, the research of organic materials is subject to people's attention in recent years day by day.
The research of luminous organic material starts from the sixties in 20th century, and professor Pope in 1963 finds anthracene (anthracene) crystal to impose hundreds of volt voltage, the luminescence phenomenon that observable is faint.Yet, until the use such as the C.W.Tang of research laboratory of U.S. Eastern Kodak company in 1987 are selected, there is the very oxine aluminium (Alq of high fluorescence efficiency and extremely strong electron transport ability
3) as luminescent material, be developed into Organic Light Emitting Diode (OLED), greatly improved the performance of OLED.Nineteen ninety, the Cavendish of univ cambridge uk laboratory J.H.Burroughes etc. is applied to OLED by polymer p-phenylene vinylene, has developed polymer OLED.These two achievements in research have started the research boom of OLED in the whole world, opened up the new research field of luminous organic material.
Luminous organic material is one and relates to many multi-disciplinary research fields such as chemistry, physics, material, electronics.Its polychromatism and wider material range of choice make its development particularly rapid.Luminous organic material can be divided into organic micromolecule compound, organic high molecular polymer and metal complexes from molecular structure.No matter these luminescent materials are at luminescence mechanism, and physical and chemical performance still has feature separately in application, thereby has different application prospects.
Chinese patent CN 102911656A provides a kind of novel large pi-conjugated aromatic hydrocarbon luminous organic material that contains, and contains benzopyran structure, has provided corresponding synthetic method and the application in organic luminescent device simultaneously.Aryl halide A-Br (A is aromatic group), aryl boric acid, alkali and solvent are added to reaction flask, utilize nitrogen bubble degassed to reaction system, add catalyzer, be warming up to 70～100 ℃, reaction 24～30h, suction filtration, washing and oven dry, finally obtain luminous organic material.Chinese patent CN 101481611A provides a kind of and has contained the novel organic luminescent material of carbazole cinnamenyl structure and synthetic method and application.This advanced luminescent material contains carbazole cinnamenyl derivant structure, synthetic be utilize Er Ge ylide group aromatic compound two to the coupling of carbazole phenyl aldehyde, directly obtain in organic solvent solvability better, have higher thermostability containing to carbazole cinnamenyl derivative.But the problems such as above-mentioned two kinds of method reaction times are longer, and reactant is more, and side reaction easily occurs, and productive rate is lower, are difficult to carry out suitability for industrialized production.
In recent years, people have carried out extensive and deep research to the luminosity of silica-base material, and these researchs not only comprise inorganic materials, and include organosilicon polymer, as Polycarbosilane (PCS).Polycarbosilane has the shortcomings such as fluorescence lifetime is short, fluorescence intensity is low, fluorescence emission peak narrow bandwidth.In order to improve the fluorescent characteristic of Polycarbosilane, there is relevant report to claim to introduce aromatic group to the side chain of Polycarbosilane, when aryl is directly connected with main chain, the red shift that the maximum absorption wavelength of Polycarbosilane in UV spectrum can not produce 15～25nm containing aryl Polycarbosilane relatively.Produce the reason of this phenomenon: when side chain aryl is directly connected with main chain, pi-conjugated system can and the main chain of σ delocalization there is further conjugation, can effectively reduce the energy gap width of Polycarbosilane, Here it is sigma-pi conjugated Polycarbosilane.Can predict, when introduce the side group of some large π delocalization on Polycarbosilane, can bring mysterious impact to the electronic structure of Polycarbosilane, can be used as luminescent material and obtain widespread use.
Chinese patent CN103102877A provides a kind of siliceous luminous organic material and its preparation method and application.Solved the problem on the luminous efficiency ground of blue light material.This material is to take two (4-bromophenyl) diphenyl silane with (A is C containing A substituting group
9-C
18fused ring aryl) anthracene class boric acid be raw material, add four (triphenyl phosphorus) palladium, sodium carbonate and tetrahydrofuran solvent, utilize nitrogen bubble degassed to reaction system, be warming up to 70～100 ℃, reaction 24～30h, cooling, suction filtration, washing and oven dry, finally obtain having the higher siliceous luminous organic material of luminous effect.But this method reflux time is long, and reactant is more, easily there is the problems such as side reaction, be difficult to carry out suitability for industrialized production.Chinese patent ZL 201010253114.9 provides a kind of organosilicon polymer luminescent material being comprised of metallorganics and Polycarbosilane and preparation method thereof.The polydimethyl silane of take is prepared Polycarbosilane as raw material, then, with metallorganics reaction, dissolves, and filters, and underpressure distillation, finally obtains pulverulent solids luminous organic material.But anti-oxidant crosslinked, anti-ultraviolet ageing and the thermal stability of the luminous organic material that this method obtains are lower, need further strengthen, and reach application purpose.
The synthetic side chain of direct method contains the Polycarbosilane of aryl due to the harshness of synthesis condition, can only introduce the substituting groups such as phenyl, naphthyl, do not allow to contain active group, and volume should not be excessive in order to avoid affect the polymerization of silane monomer on aryl.Therefore, the side group of introducing large π delocalization on the side chain of Polycarbosilane has larger difficulty for directly synthesizing, and the type of synthetic sigma-pi conjugated Polycarbosilane is limited.
Summary of the invention
Bad, the comprehensive luminous efficiency of less stable, film-forming properties that the object of the invention is to solve luminous organic material is low, emission wavelength region is limited and have the problems such as temperature cancellation characteristic, and a kind of side chain aryl conjugation luminous organic material and preparation method thereof is provided.
The general structure of described side chain aryl conjugation luminous organic material is as follows:
P wherein
na kind of in vinylbenzene, 2-vinyl naphthalene, 9-vinyl anthracene etc.
The preparation method of described side chain aryl conjugation luminous organic material, comprises the following steps:
1) Polycarbosilane (PCS) is synthetic
Polydimethylsiloxane (PMDS) is placed in airtight reactor, set heating schedule, protection of inert gas, vacuumizes insulation, then be filled with rare gas element and keep system internal gas pressure, set heating schedule again, then be incubated, question response temperature in the kettle naturally cools to after room temperature, add again normal hexane that product is dissolved, filter, vacuum is removed normal hexane, obtains flaxen solid-state Polycarbosilane (PCS);
2) small molecules of Polycarbosilane (PCS) removes
After solid-state Polycarbosilane (PCS) is ground, be soaked in dehydrated alcohol, insolubles is with dry after dehydrated alcohol drip washing;
3) side chain aryl conjugation Polycarbosilane (PP
nsynthesizing CS)
Then and aryl (P Polycarbosilane (PCS) grinding powder is dissolved in dimethylbenzene again,
n) organism mixing, then add catalyzer, be placed in three-necked bottle, under inert gas atmosphere, react, set heating schedule, insulation, then naturally cools to room temperature, again reacted solution is taken out and puts into single port bottle, negative pressure backspin steams except desolventizing, obtains faint yellow solid, then puts into vacuum drying oven insulation, finally obtain solid-state side chain aryl conjugation luminous organic material, i.e. Polycarbosilane (the PP of side chain aryl conjugation
ncS).
In step 1) in, setting heating schedule and preferably with 10 ℃/min, rise to 300～310 ℃, the time that vacuumizes insulation is preferably 2～3h, and system internal gas pressure is preferably 101Kpa; The described heating schedule that sets is again preferably 1 ℃/min and rises to 390～400 ℃, then the time of insulation is preferably 3h; Described rare gas element is preferably argon gas.
In step 2) in, described in preferably stir 12h after being soaked in dehydrated alcohol more than; Described dry temperature is preferably 60～70 ℃.
In step 3) in, described aryl (P
n) organism can be a kind of in vinylbenzene, 2-vinyl naphthalene, 9-vinyl anthracene etc.; Described catalyzer is preferably Platinic chloride (H
2ptCl
6), rare gas element is preferably argon gas, and the flow of argon gas is preferably 30～40ml/min; The described heating schedule that sets preferably rises to 100～120 ℃ with 5 ℃/min, insulation 1～10h; The temperature of described vacuum drying oven is preferably 180～200 ℃, and the time of insulation is preferably 2～4h.
The mass ratio of described polydimethylsiloxane and PCS can be 10: (1～2), is preferably 10: 1; The volume ratio of described aryl organism and dimethylbenzene can be 1: (1～3), being preferably 1: 3, the organic volume ratio of catalyzer and aryl can be (1～2): 10, preferably 1: 10.
It is raw material that polydimethylsiloxane (PMDS) is take in the present invention, obtains Polycarbosilane (PCS), then carries out the deaeration of Polycarbosilane (PCS) small molecules, then by a small amount of aryl (P by reaction in autoclave
n) Polycarbosilane (PCS) after organism (as vinylbenzene, 2-vinyl naphthalene, 9-vinyl anthracene etc.) and deaeration reacts, and finally obtains the Polycarbosilane (PP of solid-state side chain aryl conjugation
ncS).
The present invention reacts with si-h bond in system with a small amount of aryl organism, forms sigma-pi conjugated structure in system, has played the effect of end-blocking, has improved anti-oxidant crosslinked, anti-ultraviolet ageing and thermal stability.In reacted system, there is conjugated structure, but without the two dimensional structure of rigidity, lack again electron-donating group, but still show stronger luminescent properties simultaneously.
Advantage of the present invention and technique effect are as follows:
(1) body of material is Polycarbosilane, by polydimethylsiloxane By Direct Pyrolysis, is made, and the doping in later stage is directly synthetic by one kettle way, preparation technology compare with general organic fluorescence materials have simple, can suitability for industrialized production etc. advantage.
(2) synthetic product softening temperature is between 260～280 ℃, soluble in organic solvents such as normal hexane, tetrahydrofuran (THF), dimethylbenzene, be applicable to various coating molding technique, coordinate the small-sized film machine melt spun film that spins can obtain self-supporting, the organic film that width and thickness is controlled.
(3) synthetic product, under the exciting of 350nm UV-light, has royal purple light emission in 410nm left and right, and transmitting purity is high, without assorted peak.
(4) synthetic product has well anti-oxidant crosslinked, anti-ultraviolet ageing and thermal stability than Polycarbosilane.
Accompanying drawing explanation
Fig. 1 is PCS, PP
1cS and PP
2the NMR (Nuclear Magnetic Resonance) spectrum of CS (
1h NMR) spectrogram.In Fig. 1, X-coordinate is chemical displacement value (ppm); Curve a is PCS, and curve b is PP
1cS, curve c is PP
2cS.
Fig. 2 is PCS, PP
1cS and PP
2infrared (FT-IR) spectrogram of CS.In Fig. 2, X-coordinate is wave number (cm
-1); Curve a is PCS, and curve b is PP
1cS, curve c is PP
2cS.
Fig. 3 is PCS, PP
1cS and PP
2the fluorescence of CS (PL) spectrogram.In Fig. 3, X-coordinate is emission wavelength (nm), and ordinate zou is relative intensity (a.u), and excitation wavelength (Ex) is 350nm; Curve a is PCS, and curve b is PP
1cS, curve c is PP
2cS.
Fig. 4 is PCS, PP
1cS and PP
2the thermogravimetric of CS (TG) figure.In Fig. 4, X-coordinate for send out a temperature (℃), ordinate zou is thermal weight loss (%); Curve a is PCS, and curve b is PP
1cS, curve c is PP
2cS.
Embodiment
Below by specific embodiments and the drawings, the present invention will be further described.
Embodiment 1
1) 50g polydimethylsiloxane (PMDS) is placed in airtight 300ml autoclave; under argon shield, with 10 ℃/min, rise to 300 ℃, vacuumize insulation 2h, then being filled with argon gas, to keep system internal gas pressure be 101KPa; then with 1 ℃/min, rise to 390 ℃, insulation 3h.After reaction finishes, question response temperature in the kettle naturally cools to after room temperature, then adds normal hexane that product is dissolved, and filters, and vacuum is removed normal hexane, finally obtains flaxen solid-state Polycarbosilane (PCS).
2) by step 1) in product be soaked in dehydrated alcohol after grinding, stir 12h, the product after filtration is dry at 60 ℃ of vacuum drying ovens after dehydrated alcohol drip washing three times, obtains pale yellow powder.
3) get 5g step 2) in product, after grinding powder, be dissolved in 30ml dimethylbenzene, then evenly mix with the vinylbenzene of 10ml, then add 1ml Platinic chloride, be placed in three-necked bottle.Whole system is substituted gas three times, makes it under argon gas atmosphere.After reaction starts, keeping argon gas flow is 40ml/min.Then with 5 ℃/min, rise to 100 ℃, insulation 1h, naturally cools to room temperature.Then reacted solution is taken out and puts into single port bottle, negative pressure backspin steams except desolventizing, obtains faint yellow solid, then puts into the vacuum drying oven insulation 3h of 200 ℃, finally obtains the Polycarbosilane (PP of solid-state side chain aryl conjugation
1cS).Reaction equation is as follows:
4) by step 3) middle PP
1cS solid, through further grinding, is put into F7000 fluorescence spectrophotometer and is carried out the sign of photoluminescence performance (seeing Fig. 3): under the ultraviolet excitation of 350nm, and PP
1cS is that about 410nm has that intensity is higher, the good royal purple light emission of purity at wavelength.By PP
1cS is dissolved in the scanning (seeing Fig. 1) of carrying out nucleus magnetic hydrogen spectrum in deuterochloroform, and result shows, PP
1in CS system, there is aromatic group.PP
1the infrared spectrum of CS (seeing Fig. 2) shows, has silica silicon, silicon hydrogen, silicon methyl, silicon-carbon silicon structure and aromatic group in system.PP
1the thermogravimetric of CS (TG) figure, referring to Fig. 4, shows PP
1the better heat stability of CS.
Embodiment 2
1) 50g polydimethylsiloxane is placed in airtight 300ml autoclave; under argon shield, with 10 ℃/min, rise to 300 ℃, vacuumize insulation 2h, then being filled with argon gas, to keep system internal gas pressure be 101KPa; then with 1 ℃/min, rise to 390 ℃, insulation 3h.After reaction finishes, question response temperature in the kettle naturally cools to after room temperature, then adds normal hexane that product is dissolved, and filters, and vacuum is removed normal hexane, finally obtains flaxen solid-state PCS.
2) by step 1) in product be soaked in dehydrated alcohol after grinding, stir 12h, the product after filtration is dry at 60 ℃ of vacuum drying ovens after dehydrated alcohol drip washing three times, obtains pale yellow powder.
3) get 5g step 2) in product, after grinding powder, be dissolved in 30ml dimethylbenzene, then evenly mix with the 2-vinyl naphthalene of 10ml, then add 1ml Platinic chloride, be placed in three-necked bottle.Whole system is substituted gas three times, makes it under argon gas atmosphere.After reaction starts, keeping argon gas flow is 40ml/min.Then with 5 ℃/min, rise to 100 ℃, insulation 1h, naturally cools to room temperature.Then reacted solution is taken out and puts into single port bottle, negative pressure backspin steams except desolventizing, obtains faint yellow solid, then puts into the vacuum drying oven insulation 3h of 200 ℃, finally obtains the Polycarbosilane (PP of solid-state side chain aryl conjugation
2cS).Reaction equation is as follows:
4) by step 3) middle PP
2cS solid, through further grinding, is put into F7000 fluorescence spectrophotometer and is carried out the sign of photoluminescence performance (seeing Fig. 3): under the ultraviolet excitation of 350nm, and PP
2cS is that 410nm left and right has intensity higher at wavelength, the good royal purple light emission of purity.By PP
2cS is dissolved in the scanning (seeing Fig. 1) of carrying out nucleus magnetic hydrogen spectrum in deuterochloroform, and result shows, PP
2in CS system, there is aromatic group.PP
2the infrared spectrum of CS (seeing Fig. 2) shows, has silica silicon, silicon hydrogen, silicon methyl, silicon-carbon silicon structure and aromatic group in system.PP
2the thermogravimetric of CS (TG) figure, referring to Fig. 4, shows PP
2the better heat stability of CS.
Claims (10)
1. a side chain aryl conjugation luminous organic material, is characterized in that its general structure is as follows:
P wherein
na kind of in vinylbenzene, 2-vinyl naphthalene, 9-vinyl anthracene.
2. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 1, is characterized in that comprising the following steps:
1) Polycarbosilane is synthetic
Polydimethylsiloxane is placed in airtight reactor, set heating schedule, protection of inert gas, vacuumizes insulation, then be filled with rare gas element and keep system internal gas pressure, set heating schedule again, then be incubated, question response temperature in the kettle naturally cools to after room temperature, add again normal hexane that product is dissolved, filter, vacuum is removed normal hexane, obtains flaxen solid-state Polycarbosilane;
2) small molecules of Polycarbosilane removes
After solid-state Polycarbosilane is ground, be soaked in dehydrated alcohol, insolubles is with dry after dehydrated alcohol drip washing;
3) side chain aryl conjugation Polycarbosilane is synthetic
Then and aryl (P Polycarbosilane grinding powder is dissolved in dimethylbenzene again,
n) organism mixing, then add catalyzer, be placed in three-necked bottle, under inert gas atmosphere, react, set heating schedule, insulation, then naturally cools to room temperature, again reacted solution is taken out and puts into single port bottle, negative pressure backspin steams except desolventizing, obtains faint yellow solid, then puts into vacuum drying oven insulation, finally obtain solid-state side chain aryl conjugation luminous organic material, i.e. the Polycarbosilane of side chain aryl conjugation.
3. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, it is characterized in that in step 1) in, setting heating schedule is to rise to 300～310 ℃ with 10 ℃/min, and the time that vacuumizes insulation is preferably 2～3h, and system internal gas pressure is preferably 101Kpa.
4. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 1) in, the described heating schedule that sets is again to rise to 390～400 ℃ with 1 ℃/min, then the time of insulation is preferably 3h; Described rare gas element is preferably argon gas.
5. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 2) in, described in stir 12h after being soaked in dehydrated alcohol more than; Described dry temperature is preferably 60～70 ℃.
6. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 3) in, described aryl (P
n) organism is a kind of in vinylbenzene, 2-vinyl naphthalene, 9-vinyl anthracene.
7. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 3) in, described catalyzer is Platinic chloride, and rare gas element is preferably argon gas, and the flow of argon gas is preferably 30～40ml/min.
8. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 3) in, described in to set heating schedule be to rise to 100～120 ℃ with 5 ℃/min, insulation 1～10h; The temperature of described vacuum drying oven is preferably 180～200 ℃, and the time of insulation is preferably 2～4h.
9. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 2, is characterized in that in step 3) in, the mass ratio of described polydimethylsiloxane and PCS is 10: (1～2); The volume ratio of described aryl organism and dimethylbenzene is 1: (1～3), the organic volume ratio of catalyzer and aryl is (1～2): 10.
10. a kind of preparation method of side chain aryl conjugation luminous organic material as claimed in claim 9, the mass ratio that it is characterized in that described polydimethylsiloxane and PCS is 10: 1; The volume ratio of described aryl organism and dimethylbenzene is 1: 3, and the organic volume ratio of catalyzer and aryl is 1: 10.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108727596A (en) * | 2018-06-26 | 2018-11-02 | 厦门大学 | The preparation method of organosilicon polymer luminescent material and its OLED device application |
| CN110511669A (en) * | 2019-07-12 | 2019-11-29 | 仲恺农业工程学院 | Organic silicon composition and curing method thereof |
| CN115926171A (en) * | 2023-01-03 | 2023-04-07 | 中国人民解放军陆军炮兵防空兵学院 | Polysilane-polysiloxane elastic fluorescent scintillator material and preparation method thereof |
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| CN101962534A (en) * | 2010-08-11 | 2011-02-02 | 厦门大学 | Organic luminous material and preparation method thereof |
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| CN101962534A (en) * | 2010-08-11 | 2011-02-02 | 厦门大学 | Organic luminous material and preparation method thereof |
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| 姚荣迁等: "先驱体法制备连续SiC自由薄膜及其发光性能", 《硅酸盐学报》, vol. 37, no. 2, 28 February 2009 (2009-02-28), pages 187 - 197 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108727596A (en) * | 2018-06-26 | 2018-11-02 | 厦门大学 | The preparation method of organosilicon polymer luminescent material and its OLED device application |
| CN110511669A (en) * | 2019-07-12 | 2019-11-29 | 仲恺农业工程学院 | Organic silicon composition and curing method thereof |
| CN115926171A (en) * | 2023-01-03 | 2023-04-07 | 中国人民解放军陆军炮兵防空兵学院 | Polysilane-polysiloxane elastic fluorescent scintillator material and preparation method thereof |
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