CN109438454B - Nano unfilled corner lattice, preparation method and photoelectric application thereof - Google Patents
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Abstract
The invention provides a nano unfilled corner lattice which is based on fluorene or azafluorene and has a rigid geometric structure
In the formula (I), the compound is shown in the specification,
is composed of 4-26 aromatic hydrocarbons or aromatic hydrocarbon structures containing hetero atoms, wherein ● is a hydrogen atom or a halogen atom. The nano unfilled-corner lattice is prepared by self-cyclization after Friedel-crafts-reaction, and has the advantages of mild reaction conditions, unique performance, cheap raw materials, simple operation, easy preparation, low toxicity and low cost.
Description
Technical Field
The invention relates to a nanometer unfilled corner lattice, a preparation method thereof and photoelectric application, in particular to a soluble annular nanometer unfilled corner lattice and a preparation method thereof, and relates to application of the materials in the fields of organic electroluminescence, organic electric storage, organic photoluminescence, photovoltaic cells, organic nonlinear optics, sensing, organic laser and the like, belonging to the fields of organic molecular semiconductor materials and high and new photoelectric technology.
Background
From the kodak company dungdong cloud research group of 1987 [ Tang, c.w.; van Slyke, s.a.appl.phys.lett.1987,51,913.] and 1990 Burroughes et al, cambridge university, england [ Burroughes, j.h.; bradley, d.d.c.; brown, a.b.; marks, r.n.; mackay, k.; friend, r.h.; burn, p.l.; holmes, a.b. nature 1990,347,539, discloses thin film type Organic electroluminescent devices (Organic Light-emitting Diodes) and polymer Light-emitting Diodes (polymer Light-emitting Diodes) made of Organic and polymer fluorescent materials, respectively, and Organic flat panel displays are considered to be a display product that is marketed next to liquid crystal displays. Meanwhile, other organic photoelectric fields have undergone great technological changes, including organic field effect transistors, organic solar cells, nonlinear optics, photoelectric sensing, lasers, and the like. The organic plastic electronic product has the advantages of low material preparation cost, simple device preparation process and capability of preparing flexible and large-area devices. Therefore, more and more scientific workers at home and abroad pay great attention to the development of novel organic photoelectric functional materials with practical market potential.
Up to now, the development of new highly stable carrier transport or capture materials and light emitting materials has become a key factor in improving the efficiency and lifetime of organic electronic, photonic, electro-optical and optoelectronic devices. The organic nano grid is a porous material and has unique photoelectric physicochemical properties, such as large specific surface area, low dielectric constant, low conductivity, unique photoelectric chemical properties and the like, so that the organic nano grid has good application prospects in the fields of gas adsorption, chemical separation, heterogeneous catalysis, sensing and the like, and is of great interest. How to prepare soluble organic porous compounds with regular structure and excellent performance is a popular topic in the field.
The search shows that the Chinese patent with the patent number of 201610029902.7 discloses a fluorenyl windmill grid and a preparation and application method thereof, the fluorenyl windmill grid is an at least ternary or more ternary ring grid when n is 1-10, and is also a thiophene-containing acceptor group grid compound, and the fluorenyl windmill grid is mainly applied to a larger storage window and has poor stability; the Chinese patent with the application number of 201711188236.2 discloses an organic nano grid, a nano polymer thereof and a preparation method thereof, wherein the organic nano grid is the nano grid with a middle bridge connecting group, the nano polymer is a one-dimensional azafluorene grid compound, and the synthesis method adopts a synthesis method that organic acid participates in supermolecule induced polymerization.
Disclosure of Invention
The invention aims to solve the technical problems that the defects of the prior art are overcome, the soluble nanometer unfilled corner lattice with a regular structure and excellent performance is provided, the preparation method and the photoelectric application of the soluble nanometer unfilled corner lattice are provided, the porous nanometer lattice has larger specific surface area, good solubility, thermal stability, electrochemical stability and spectral stability, the absorption spectrum and the luminescence spectrum of the porous nanometer lattice can be regulated and controlled by adjusting the electronic energy level of the porous nanometer lattice, and the porous nanometer lattice is an organic photoelectric functional material with a great application prospect.
The invention provides a nano unfilled corner lattice, which is based on fluorene or azafluorene and has a rigid geometric structure, and the structure of the nano unfilled corner lattice is shown as a structural general formula I:
in the formula (I), the compound is shown in the specification,
is composed of 4-26 aromatic hydrocarbons or aromatic hydrocarbon structures containing hetero atoms, wherein ● is a hydrogen atom or a halogen atom.
The nano unfilled corner lattice is a halogenated or halogen-free binary unfilled corner lattice, and is also a carbazole-containing donor group unfilled corner lattice compound, and the carbazole-containing binary unfilled corner lattice has a larger main application switch and better stability performance.
Hydrogen and carbon spectra by nuclear magnetic resonance (1H NMR、13C NMR), time of flight mass spectrometry (MALDI-TOF MS), etc. characterize the structure of the nanograms. The thermal stability of the materials is tested through thermogravimetric analysis and differential thermal analysis, the electrochemical properties of the materials are characterized through cyclic voltammetry, and the spectral stability of the materials is tested through a thin film high-temperature annealing mode.
The nano-unfilled corner lattices are tested by the means, and the result shows that the nano-unfilled corner lattices have good thermal stability, good electrochemical stability and good spectral stability. The nano unfilled-corner lattice has adjustable band gap and intramolecular stacking effect, and can be used as a high-efficiency host or guest material, a hole transport material or an electron transport material. The nanometer unfilled corner lattice can be processed in solution, and can be used in host-guest chemistry and organic field effect transistor memories; the nanometer unfilled corner lattice can also be applied to the fields of organic electroluminescence, organic transistor memories, organic photoluminescence, organic photovoltaic cells, organic nonlinear optics, organic lasers and the like.
In a further aspect of the present invention, ● is at least one of F, Cl, Br and I.
Further, the nano-unfilled corner lattice preferably has a fluorene structure, and the fluorene nano-unfilled corner lattice has the following structure:
in the formula, W is C or N, Y is H, F, Cl, Br or I, Ar1Is one of the following structures:
Ar2is one of the following structures:
in the above formulae, R1～R9An alkoxy group which is a hydrogen atom, a straight chain having 1 to 22 carbon atoms, a branched chain having 1 to 22 carbon atoms, a cyclic alkyl chain having 1 to 22 carbon atoms or a cyclic alkyl chain having 1 to 22 carbon atoms; x is O, S or Se.
The invention also provides a preparation method of the nanometer unfilled corner lattice, tertiary alcohol is subjected to Friedel-crafts reaction in acid catalysis, and self-cyclization is carried out to obtain the nanometer unfilled corner lattice material, wherein the reaction route is shown as a reaction formula (III):
wherein ● is H, F, Cl, Br or I.
The invention provides photoelectric application of a nanometer unfilled corner lattice, wherein the nanometer unfilled corner lattice is applied to an organic light-emitting diode, the organic light-emitting diode sequentially comprises a transparent anode, a light-emitting layer, an electron injection layer and a cathode, and the light-emitting layer consists of a host material and a doped object; the nano unfilled corner lattice is used as a host material or a doped guest material.
Further, the nanometer unfilled corner lattice is applied to an organic transistor storage device, and the organic transistor storage device is structurally characterized in that a low grid top contact is formed by sequentially arranging a substrate, a grid electrode, a tunneling layer, an organic semiconductor, a source electrode and a drain electrode; the nano unfilled corner lattice is used as a dielectric layer material and is prepared by vacuum evaporation, solution spin coating or ink-jet printing.
In short, the semiconductor material is applied to the photoelectric fields of organic field effect transistor memories, organic light emitting diodes, organic solar cells, explosive detection and the like.
Compared with the prior art, the invention adopting the technical scheme has the following technical effects:
1. the nano unfilled-corner lattice is prepared by self-cyclization after Friedel-crafts reaction, has mild reaction conditions, unique performance, cheap raw materials, simple operation, easy preparation, low toxicity and low cost;
2. the nano corner-lacking lattices have regular structure, large rigidity, good solubility and adjustable electronic energy level, and are convenient for nano film culture or solution processing to expand the application range of the material;
3. the nano unfilled corner lattice shows ring characteristics and unique and excellent photoelectric characteristics, and has excellent mechanical characteristics of nano materials;
4. the nano unfilled corner lattice as a dielectric material has excellent bipolar storage performance in an organic transistor, such as a large storage window and storage switching ratio, a lower operating voltage, a long storage life and the like;
5. the pore structure of the nano unfilled-corner lattice can perform host-guest interaction with an electron donor or an electron acceptor, and the performance of the device can be effectively regulated and controlled in an organic optoelectronic device;
6. the nanometer unfilled corner lattice has the advantages of high thermal, electrochemical stability, spectral stability and the like.
Therefore, the nano-lattice is expected to become a new generation and novel practical organic molecule photoelectric material, and the nano-lattice has good application prospect in the fields of organic electronics, magnetoelectronics, photoelectrons, mechano-electronics, nanobiology and the like.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a nano-sized unfilled corner lattice I of the present invention.
FIG. 2 is a carbon spectrum of the nano-sized corner-lacking lattice I of the present invention.
FIG. 3 shows the ultraviolet absorption and fluorescence emission spectra of the nano-sized unfilled corner grids I of the present invention.
Fig. 4a is a schematic view of a layer structure of the device with the nano-unfilled corner lattice I as the dielectric layer in the invention.
Fig. 4b is a transfer diagram of an organic transistor memory device with a nano-unfilled corner lattice I as a dielectric layer device according to the present invention.
Fig. 5a is a memory graph of an organic transistor memory with a nano-unfilled corner lattice I as a dielectric layer according to the present invention.
Fig. 5b is a graph of the forward write for an organic transistor memory with the nano-unfilled corner lattice I as the dielectric layer in the present invention.
Fig. 6 is a graph showing positive and negative write and erase curves of an organic transistor memory in which a nano-lattice I is used as a dielectric layer according to the present invention.
Detailed Description
The technical scheme of the invention is further explained in detail by combining the attached drawings:
the invention provides a nano unfilled corner lattice, which is based on fluorene or azafluorene and has a rigid geometric structure, and the structure of the lattice is shown as a structural general formula I:
in the formula (I), the compound is shown in the specification,
is composed of 4-26 aromatic hydrocarbons or aromatic hydrocarbon structures containing hetero atoms, wherein ● is a hydrogen atom or a halogen atom (F, Cl, Br or I). The preferable nanometer unfilled corner lattice is a fluorene structure, and the fluorene nanometer unfilled corner lattice has the following structure:
in the formula, W is C or N, Y is H, F, Cl, Br or I, Ar1Is one of the following structures:
Ar2is one of the following structures:
in the above formulae, R1～R9To hydrogen atomsAn alkoxy group of a straight chain having 1 to 22 carbon atoms, a branched chain having 1 to 22 carbon atoms, a cyclic alkyl chain having 1 to 22 carbon atoms or a cyclic alkyl chain having 1 to 22 carbon atoms; x is O, S or Se.
A preparation method of nanometer unfilled corner lattice is characterized in that tertiary alcohol is subjected to Friedel-crafts reaction in acid catalysis, and self-cyclization is carried out to obtain the nanometer unfilled corner lattice material, wherein the reaction route is shown as a reaction formula (III):
wherein ● is H, F, Cl, Br or I.
In the nano unfilled corner lattice of the present invention, when W is C, Ar1Is p-octyloxybenzene, Y is Br or H, Ar2When the nano-crystal is N-ethyl carbazole or 2,2' -bithiophene, the structures of the nano-crystal lattice are respectively as follows:
the key steps of the preparation method of the nanometer unfilled corner lattice are Suzuki coupling reaction and acid-catalyzed Friedel-crafts reaction, and the preparation of the nanometer unfilled corner lattice IV is taken as an example. The specific reaction is as follows:
in the first step, 1,4 dioxane is used as a reaction solvent, Br-EtCz is adopted to react with pinacol diboron to prepare CzBO, DBrFO is utilized to prepare brominated fluorenol monomer DBrFOH through Grignard reaction, the prepared CzBO and DBrFOH are utilized to obtain brominated BrCzFOH through SuZuKi reaction, and the brominated BrCzFOH is subjected to Friedel reaction under dilute concentration to obtain a ring closure product BrCzGrid with high yield and good solubility. The specific synthetic route is as follows:
example 1
And (3) drying the washed three-mouth reaction bottle (containing a magnetic stirrer) and the condenser pipe in an oven, taking out the reaction bottle and the condenser pipe after drying for 12h, tightly connecting the reaction bottle and the condenser pipe, and removing air in the refined 1, 4-dioxane bubbles by using a nitrogen balloon. Br-EtCz (10g,36.6mmol) and pinacol diboron (OMDOB) (12g,37.36mmol) and Pd (OAc)2(0.256g,1.12mmol), DPPF (1.22g,2.196mmol), KOAc (11g,0.115mol) and the like were put into a reaction flask, the reaction flask was closed and then put into an oil bath, 200mL of 1, 4-dioxane was further injected into the reaction flask, and the oil bath was heated to 110 ℃ under stirring and refluxed for 15 hours to obtain a white solid sample CzBO (8g, 80%). The detection result of the sample CzBO is as follows:1H NMR(400MHz,CDCl3)δ8.62(s,1H),8.15(d,J＝7.8Hz,1H),7.94(dd,J＝8.2,1.2Hz,1H),7.51-7.44(m,1H),7.42(d,J＝8.2Hz,2H),7.29-7.22(m,1H),4.38(q,J＝7.2Hz,2H),1.48-1.38(m,15H).13C NMR(100MHz,CDCl3)δ142.12,140.06,132.19,127.87,125.68,123.25,122.74,120.68,119.27,108.53,107.89,94.23,83.51,37.57,24.99,13.91.
example 2
In N2The DBrFO (5g,11.07mmol) was dissolved in dry THF and the two were slowly stirred in an ice-water bath, and the prepared Grignard reagent, which was obtained by mixing p-bromooctyloxybenzene (9.4g,33.12mmol), magnesium turnings (0.82g,34.2mmol) and 50mL THF, was then withdrawn using a syringe and slowly added to the DBrFO dry tetrahydrofuran solution. Then, the reaction flask was moved to an oil bath and reacted at 70 ℃ for 8 hours with stirring. With saturated NH4Slowly dripping Cl aqueous solution for quenching, extracting by dichloromethane, and performing column chromatography (silica gel 200-300 mesh, eluent V)Petroleum ether:VMethylene dichloride2.5:1) gave DBrFOH (4.3g, 86%) as a pale yellow viscous product.
Example 3
According to Na2CO3(2mol/L)/KF (2mol/L)Preparing a mixed aqueous solution, and using 50mL (V) of 10mL of the prepared mixed aqueous solution mixed with 50mL of the organic phase solutionTol:VTHF1:1), and then continuously bubbling nitrogen gas for 4 hours to obtain a toluene/tetrahydrofuran mixed phase system. A500 mL three-necked flask, a stirrer and a spherical condenser tube were assembled. DBrFOH (3g,4.55mmol), CZBO (1.48g,4.6mmol), Pd (PPh)3)4Adding the mixture into three-mouth bottles in turn according to the feeding ratio and sealing the three-mouth bottles. Vacuumizing the device for nitrogen protection, then placing the device in an oil bath pot, injecting 50mL of toluene/tetrahydrofuran mixed phase system into a reaction bottle, heating and stirring at 90 ℃, injecting 10mL of aqueous solution into the system after reacting for about 20 minutes, and stopping the reaction after reacting for 36 hours. The reaction was quenched with water, extracted with dichloromethane and then subjected to column chromatography (silica gel 200-300 mesh, eluent V)Petroleum ether：VMethylene dichloride2.5:1) gave BrCzFOH (2.25g, 75%) as a pale yellow solid. The detection result of the product BrCzFOH is as follows:1H NMR(400MHz,CDCl3)δ8.29(d,J＝1.5Hz,1H),8.14(d,J＝7.7Hz,1H),7.76-7.71(m,2H),7.70-7.65(m,2H),7.50(ddd,J＝6.7,6.1,3.2Hz,4H),7.42(d,J＝8.6Hz,2H),7.38-7.32(m,2H),7.27(s,1H),7.24(d,J＝7.6Hz,1H),6.82(d,J＝8.9Hz,2H),4.37(q,J＝7.2Hz,2H),3.91(t,J＝6.6Hz,2H),2.54(s,1H),1.79-1.69(m,2H),1.47-1.37(m,5H),1.29(dd,J＝11.7,6.4Hz,9H),0.88(t,J＝6.6Hz,3H).13C NMR(100MHz,CDCl3)δ158.64,152.92,151.04,142.82,140.47,139.58,138.25,136.80,134.48,132.07,131.63,128.19,128.14,126.72,126.00,125.05,123.54,123.12,121.76,121.40,120.70,120.57,119.12,118.86,114.43,108.73,83.38,68.05,37.66,31.95,29.48,29.37,26.16,22.80,14.28,13.92.
example 4
BrCzFOH (1g,1.52mmol) was dissolved in dry dichloromethane (500mL) and BF added with stirring3·Et2O (1mL, 9.6mmol), followed by reaction at room temperature for 12h, quenching with water, separation of the organic and aqueous phases, column chromatography (eluent V petroleum ether: V dichloromethane ═ 2:1-5:1) afforded binary ring lattice BrCzGrid, which was a white solid (0.36g, 36%) with high solubility. The detection result of the product BrCzGrid is as follows:1H NMR(400MHz,CDCl3)δ8.61(s,2H),8.31(s,2H),8.06(s,2H),7.58(dd,J＝16.3,4.3Hz,8H),7.27(d,J＝6.6Hz,4H),7.10(d,J＝7.5Hz,4H),6.95(d,J＝8.6Hz,4H),6.78-6.68(m,6H),3.90-3.80(m,4H),3.21(s,4H),1.33(d,J＝47.3Hz,36H).13C NMR(100MHz,CDCl3)δ158.16,153.82,152.12,140.30,139.32,139.11,138.98,137.06,134.93,130.40,129.95,129.24,124.12,124.12，123.12,122.64,121.86,120.74,119.96,116.61,114.37,108.17,107.07,77.30,77.04,76.72,67.62,65.17,36.74,31.91,29.98，29.08,26.16,22.65,14.10,13.84,13.37.
example 5
An organic transistor memory device for realizing bipolar storage by light assistance has a structure of Si/SiO2(320 nm)/nanogrid (15nm)/Pentacene (50 nm)/Cu. The device includes: gate, insulator, dielectric, hole transport layer, source, drain. Wherein the gate is made of Si, and the insulator is made of SiO with a thickness of 320nm2The thickness of the dielectric BrCzgrid is 15nm, the thickness of the hole transport layer Pentacene is 50nm, and the source electrode and the drain electrode are made of Cu, so that the organic transistor memory device with good memory performance is obtained. At a negative gate voltage (-24V), a 5.32V memory window is achieved. Under the gate voltage and illumination of the positive direction (12V), the device can write in the negative direction, and has a larger storage window, but cannot write in the positive direction, which indicates that the binary carbazole-based lattices can store holes but cannot store electrons. Preferably, the on-off ratio remains 10 after 10000 seconds4Above, the device has better stability, and the cycle of reading and writing is comparatively stable.
The above description is only an embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can understand that the modifications or substitutions within the technical scope of the present invention are included in the scope of the present invention, and therefore, the scope of the present invention should be subject to the protection scope of the claims.
Claims (2)
1. A nanometer unfilled corner lattice is characterized in that the structural general formula is as follows:
2. the photovoltaic application of the nano-unfilled corner lattice in claim 1, wherein the nano-unfilled corner lattice is applied to an organic transistor memory device comprising a gate electrode, an insulator, a dielectric, a hole transport layer, a source electrode and a drain electrode, wherein the gate electrode is made of Si, and the insulator is made of SiO with a thickness of 320nm2The thickness of the dielectric BrCzgrid is 15nm, the thickness of the hole transport layer Pentacene is 50nm, and the source electrode and the drain electrode are made of Cu.
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| CN106496527A (en) * | 2016-09-20 | 2017-03-15 | 南京邮电大学 | A kind of fluorenyl is to receptor type nanometer polymer, preparation method and applications |
| CN106518892A (en) * | 2016-09-20 | 2017-03-22 | 南京邮电大学 | Donor-acceptor type fluorenyl nanometer grid material, preparation method and application thereof |
| CN107955135A (en) * | 2017-11-11 | 2018-04-24 | 南京邮电大学 | It is conjugated organic grid nanometer polymer and its methods for making and using same |
| CN107973797A (en) * | 2017-11-24 | 2018-05-01 | 南京邮电大学 | A kind of organic nano lattice, its nanometer polymer and preparation method thereof |
| CN108517030A (en) * | 2018-04-23 | 2018-09-11 | 南京邮电大学 | Fluorenyl nano grids polymer and its preparation method and application |
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