CN106892868B - A kind of 8-hydroxyquinoline Zn complex and preparation method thereof with one-dimensional catenary structure - Google Patents
A kind of 8-hydroxyquinoline Zn complex and preparation method thereof with one-dimensional catenary structure Download PDFInfo
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- CN106892868B CN106892868B CN201710114518.1A CN201710114518A CN106892868B CN 106892868 B CN106892868 B CN 106892868B CN 201710114518 A CN201710114518 A CN 201710114518A CN 106892868 B CN106892868 B CN 106892868B
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- hydroxyquinoline
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- 0 CC1=CC[C@@](C=Cc2nc(c(*3CC3)ccc3)c3cc2)C(Cl)=C1 Chemical compound CC1=CC[C@@](C=Cc2nc(c(*3CC3)ccc3)c3cc2)C(Cl)=C1 0.000 description 1
- LHPBMLISQCCPBM-UHFFFAOYSA-N Cc1cc(Cl)ccc1CCc1nc(c(O)ccc2)c2cc1 Chemical compound Cc1cc(Cl)ccc1CCc1nc(c(O)ccc2)c2cc1 LHPBMLISQCCPBM-UHFFFAOYSA-N 0.000 description 1
- FGEKSFQAAXPJHB-VMPITWQZSA-N Oc1cccc2c1nc(/C=C/c(c(Cl)c1)ccc1Cl)cc2 Chemical compound Oc1cccc2c1nc(/C=C/c(c(Cl)c1)ccc1Cl)cc2 FGEKSFQAAXPJHB-VMPITWQZSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/30—Metal salts; Chelates
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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Abstract
The application belongs to metal complex field, and in particular to a kind of 8 oxyquinoline Zn complexes and preparation method thereof with one-dimensional catenary structure.8 oxyquinoline Zn complex provided by the present invention, shown in its chemical constitution such as formula (I), with unique one-dimensional catenary structure, and good dissolubility, thermal stability and high luminous intensity are shown, can be used as wet processing and make associated light emitting device；In addition, the preparation method of the 8 oxyquinoline Zn complexes provided by the invention with one-dimensional catenary structure is easy to operate, raw material sources are extensively, it can be achieved that large-scale production, has wide Commercial Prospect.
Description
Technical field
The invention belongs to metal complex fields, and in particular to a kind of 8-hydroxyquinoline zinc with one-dimensional catenary structure is matched
Close object and preparation method thereof.
Background technology
Organic electroluminescence device (OLED) have visual angle is wide, low in energy consumption, fast response time, it is simple for process, can realize entirely
The advantages that color is shown, therefore have broad application prospects in FPD and solid light source field.From the U.S. in 1987
Since C.W.Tang is reported for the first time using three (8-hydroxyquinoline) aluminium (Alq3) making organic electroluminescence device, numerous is novel
Electroluminescent organic material (OELM, Organic Electroluminescence Materials) is successfully synthesized to meet
Improve the requirement of OLED device performance.
Luminescent material be the substance of lighting function is finally undertaken in device, therefore the luminous efficiency of luminescent material, shine the longevity
The properties such as life and luminescent chromaticity will all have a direct impact the performance of OLED.As the luminescent material in OLED should have as
Lower condition：1) there is efficient solid state fluorescence, without apparent concentration quenching phenomena；2) there is good chemical stability and heat
Stability does not react with electrode and carrier transmission material；3) it is easy to form fine and close noncrystalline membrane and is not easy to tie
It is brilliant；4) there is emission wavelength appropriate；5) there is good conductive characteristic and certain carrier transport ability.
8-hydroxyquinoline metal complex has good thermal stability, high fluorescence and its good electron-transport work(
Can, therefore become one of the material for being applied to most reliable electron-transport and transmitting in OLED.However, the metal complexes is molten
Solution property and film forming are poor, and preparation difficulty is big, limit such complex and are prepared in luminescent device as a kind of luminescent material
Scale application in field.
Invention content
In view of this, the present invention provides a kind of with the 8-hydroxyquinoline Zn complex of one-dimensional catenary structure and its preparation
Method, 8-hydroxyquinoline Zn complex provided by the present invention have higher luminous intensity, good thermal stability, Yi Jiliang
Good dissolubility.
The specific technical solution of the present invention is as follows：
The present invention provides a kind of 8-hydroxyquinoline Zn complexes with one-dimensional catenary structure, have as shown in formula I
Structure：
The present invention also provides a kind of preparation method of the above-mentioned 8-hydroxyquinoline Zn complex with one-dimensional catenary structure,
Including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, are obtained in reaction
Mesosome；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc and matches
Close object.
Preferably, reaction dissolvent described in step a) is acetic anhydride.
Preferably, the condition of the step a) reactions is：It is heated to reflux under the protection of inert gas；
The inert gas includes nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
Preferably, step b) first heating stirrings after pyridine is added, then add water and are heated at reflux.
It is furthermore preferred that the temperature of the heating stirring is 132~135 DEG C, the time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
Preferably, zinc salt described in step c) includes：It is one or more in zinc perchlorate, zinc nitrate and zinc chloride；
The molar ratio of the ligand and zinc salt is (3~5):(8~12).
Preferably, the step c) reaction dissolvents are the mixed solution of n,N-Dimethylformamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(100~150) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is (1~4):(0.5~2).
Preferably, the temperature reacted described in step c) is 60~80 DEG C, and the time is for 24 hours.
The present invention provides a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure, chemical constitution such as formulas
(I) shown in, there is unique one-dimensional catenary structure, and show good thermal stability, dissolubility and high luminous intensity, can makees
For a kind of performance is good, cost is relatively low, the specific novel soluble small light-emitting molecules of space structure；The present invention passes through in 8- hydroxyl quinolines
Chlorine atom is introduced in quinoline group, improves the dissolubility and film forming of complex, wet processing can be used and make associated light device
Part is avoided using complicated preparation process and making apparatus, and manufacturing cost is cheap, and raw material sources are extensively, it can be achieved that large-scale
Production has wide Commercial Prospect.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The embodiment of invention for those of ordinary skill in the art without creative efforts, can also basis
The attached drawing of offer obtains other attached drawings.
Fig. 1 is the nuclear magnetic resonance spectroscopy of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 2 is the crystal structure figure of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 3 is the one-dimensional catenary structure figure of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 4 is the PXRD figures of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 5 is the ultraviolet spectra for titration figure of ligand and zinc salt coordination in embodiment 1；
Fig. 6 is the fluorescence titration spectrogram of Zn complex and ligand in embodiment 1；
Fig. 7 is the fluorescence spectra of the 8-hydroxyquinoline Zn complex and ligand that are obtained in embodiment 1；
Fig. 8 is the fluorescence lifetime curve and matched curve figure of the Zn complex obtained in embodiment 1；
Fig. 9 is the thermogravimetric analysis figure (TGA) of the 8-hydroxyquinoline Zn complex obtained in embodiment 1.
Specific implementation mode
The present invention provides a kind of 8-hydroxyquinoline Zn complexes with one-dimensional catenary structure, have as shown in formula I
Structure：
In the present invention, the 8-hydroxyquinoline Zn complex crystal belongs to centrosymmetric monoclinic system, space group
It is C2/c, is one-dimensional space paradigmatic structure, structural unit includes two ligands of Zn (II) atomic nucleus of a hexa-coordinate.
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline Zn complex, including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, are obtained in reaction
The chemical name of mesosome, the reaction intermediate is (E) -2- [2,4- Dichloro-phenyl vinyl] -8- acetoxyl group quinoline；
Wherein, the reaction equation involved in step a) is as follows：
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand, the chemical name of the ligand
For (E) -2- [2,4- Dichloro-phenyls vinyl] -8-hydroxyquinoline；
Wherein, the reaction equation involved in step b) is as follows：
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc and matches
Object is closed, molecular formula is Zn (C17H11Cl2NO)2；
Wherein, the reaction equation involved in step c) is as follows：
In the present invention, the reaction dissolvent employed in step a) is preferably acetic anhydride；
The condition of the reaction is：It is heated to reflux under the protection of inert gas.
Further, the temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h；
The inert gas is preferably nitrogen, argon gas or helium, more preferably nitrogen；
The molar ratio of 2- methyl -8-hydroxyquinoline and 2,4 dichloro benzene formaldehyde is preferably (1~1.5):1.
In the present invention, in step b) after pyridine is added first heating stirring, then add water and be heated at reflux.
Further, the temperature of the heating stirring is 132~135 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
In the present invention, zinc salt described in step c) is preferably one kind or more in zinc perchlorate, zinc nitrate and zinc chloride
Kind, more preferably zinc perchlorate；The reaction dissolvent is preferably the mixed solution of N,N-dimethylformamide and methanol.
Further, the molar ratio of the ligand and zinc salt is preferably (3~5):(8~12), more preferably 4:10；
The ratio of the ligand and N,N-dimethylformamide is preferably 1mmol:(100~150) mL, more preferably
1mmol:125mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is preferably (1~4):(0.5~2), more preferably
2:1；
The temperature of the reaction is 60~80 DEG C, and the time is for 24 hours.
Technical scheme of the present invention is clearly and completely described below in conjunction with the specific embodiment of the invention, it is clear that
Described embodiment is a part of the embodiment of the present invention, instead of all the embodiments.Those skilled in the art should manage
Solution, modifies to specific embodiments of the present invention or is replaced on an equal basis to some technical characteristics, without departing from the present invention
The spirit of technical solution should all cover in the scope of protection of the invention.
Embodiment 1
(1) preparation of intermediate
A, weigh 2- methyl -8-hydroxyquinoline 1.75g and 2,4- dichlorobenzaldehydes 1.74g in the round-bottomed flask of 100mL,
The acetic anhydride dissolving of 10mL is added, obtains mixed liquor；
B, by the mixed liquor that step A is obtained carried out under the protection of nitrogen magnetic agitation, 145 DEG C be heated to reflux 20h, with
The progress of reaction, the color of reaction solution are gradually deepened, and switch to brown by the beginning light yellow, reaction solution is in opaque muddy
Turbid state is also precipitated with a small amount of solid in reaction process；
C, reaction solution is poured into the ice water of 100mL after reaction solution is cooled to room temperature, yellow solid, filtrate is precipitated
Three times with dichloromethane extraction, merge the organic phase of extraction gained three times；The acetic acid in organic phase is washed away with distilled water, is then used
Anhydrous sodium sulfate is dried, then organic phase is concentrated under reduced pressure and obtains crude product；
D, it uses petrol ether/ethyl acetate to carry out silica gel column layer as eluant, eluent and is separated by decantation to 3.46g intermediates, yield is
88%.
(2) preparation of ligand
The intermediate of 1g is dissolved in the 100mL round-bottomed flasks equipped with 10mL pyridines, is added after 133 DEG C of heating stirring 30min
Enter 5mL water, while water is added, solution quickly becomes dark cloudy state；Continue heating reflux reaction after 4 hours, obtains oil
The dope of shape stops reaction.A large amount of crude product solid is precipitated after cooling, uses petrol ether/ethyl acetate as eluant, eluent point
From obtaining yellow powder ligand, yield 93.6%.
(3) preparation of 8-hydroxyquinoline Zn complex
Above-mentioned ligand (0.004mmol) is dissolved in DMF (0.5mL), MeOH (0.25mL) is added, is eventually adding Zn
(ClO4)2The DMF solution of (0.01mmol), is sealed in the vial of 10mL, and for 24 hours, cooling collect obtains red bar for 80 DEG C of heating
Shape crystal, is washed with MeOH, dry at 30 DEG C, obtains product, yield 86%.Wherein, the volume ratio of DMF and MeOH is 2:1.
(4) Structural Identification of 8-hydroxyquinoline Zn complex
Using MRI scan complex hydrogen signal and its hydrogen signal is pointed out, the results are shown in Figure 1；
The ir data of product, characteristic waves (cm are measured using Fourier Transform Infrared Spectrometer-1) it is 3050,2930,
2830,1620,1550,1500,1030,1280.
The crystal structure of the complex product is measured using German Brooker X single crystal diffractometers, measuring temperature 298K is adopted
With the Mo-K alpha rays through graphite monochromator monochromatizationIrradiation is collected diffraction data using scan mode, is used
SAINT programs carry out data convert and integrate to obtain crystal structure figure, as a result as shown in figures 2-3, Advances in crystal X-ray diffraction tables of data
Bright complex crystal of the present invention belongs to monoclinic system, and space group C2/c is one-dimensional space paradigmatic structure, and structural unit includes
The Zn (II) and two ligands of one hexa-coordinate.Zn (II) atom at center receives N and O from two different ligands, simultaneously
Adjacent center metal Zn is linked into the space structure of one dimensional infinite extension by the phenol oxygen atom of other ligands.Wherein,
ZnZn distances areThe Zn-N being centered around around Zn atoms isZn-O isWithThere is weaker C-HO hydrogen bond actions (hydroxyl O atom in 3 intramolecular of complex
C-H groups on vinyl),∠ C-HO=128.9 °, Zn of these hydrogen bonds in polymer
Important function has been played in structural unit.
The complex is measured using PXRD, as shown in figure 4, the PXRD p-wires and simulation curve energy of complex
It is preferable to coincide, illustrate that 8-hydroxyquinoline class Zn complex is single pure phase.
Fig. 5 is the ultraviolet spectra for titration figure of ligand and zinc salt coordination, simulates the process of ligand (L) and metallic zinc coordination,
It is gradually carried out with the instillation reaction of zinc solution, significant change occurs in absorption peak.Two major absorbance peaks of ligand are concentrated
Ultraviolet absorption peak at 300~400nm, 298nm is the signal peak of quinoline ring, and the UV absorption of 347nm or so is due to electricity
Caused by lotus shifts.In Figure 5, with the increase of the addition zinc ion ratio of zinc salt, acromion of the ligand at 347nm is with zinc
The addition of salt is gradually reduced, and maximum absorption wavelength occurs and apparent Red Shift Phenomena, absorption peak of the ligand at 304nm occurs
There is new complex absorption peak to 319nm at 448nm in red shift.Possible cause from absorption peak red shift is：Match in complex
The transfer of charge between body or between ligand inside so that the HOMO tracks on benzene oxygen ring and the LUMO interorbitals on pyridine ring
π → π * electron transitions occur.As shown in Figure 5, with the continuous instillation of zinc ion, the molar ratio moment generation of zinc ion and ligand
Variation, molar ratio are more than 1:When 2, no longer absorption curve changes, and illustrates that the reaction was complete between ligand and zinc ion.
In order to further detect the characteristics of luminescence of ligand and complex, we have tracked ligand and zinc salt in methanol solution
(10-4Mol/L the fluorescence titration process in).As shown in fig. 6, ligand, under the excitation of 340nm, fluorescent liquid emits
Wave crest is 464nm (blue)；Under the excitation of 340nm (orange-yellow), fluorescent liquid transmitting wave crest is complex
608nm.After ligand and zinc are coordinated as can see from Figure 6, apparent red shift has occurred in the wavelength of fluorescence of compound, we recognize
Have two for reason：First, the π track reverse coupleds after metal coordination between metal and ligand increase the flowing of main orbit electronics
Property, ionic bond is formed between metal ion and ligand；Second, metallic element, which is added to, after coordination increases the bond distance of hexatomic ring in ring
Add, forms a non-radiative track by inhibiting the flowing of phenyl ring electronics and increasing rigidity to reduce maximum system energy, and final
Lead to the reduction of π~π * orbital energies.
The photoluminescent property of ligands and complexes at ambient temperature is as shown in fig. 7, Zn complex has at 626nm emission peaks
Very strong luminescence generated by light, excitation wavelength are 360nm, emit stronger red light.(the λ em=compared with free ligand L1-L3
457nm), red shift most has occurred with big launch wavelength.This is derived from turning with the charge in vivo or between ligand for complex
It moves.
Fig. 8 is the fluorescence lifetime curve and matched curve figure of complex, is fitted to test data, by calculating to obtain this
The fluorescence lifetime of the 8-hydroxyquinoline Zn complex monokaryon crystal of embodiment is 2.90ns.
Thermogravimetric analysis further is carried out to 8-hydroxyquinoline class Zn complex monokaryon crystal.Determination condition is：Heating rate
For 10 DEG C/min, ranging from 20~1000 DEG C of measuring temperature, as shown in figure 9,8-hydroxyquinoline Zn complex monokaryon crystal is
For the weightless temperature range in one stage at 364 DEG C~422 DEG C, mass fraction reduces 14.97%.Illustrate the complex can compared with
Stablize relatively at high temperature, necessary condition is provided for vacuum evaporation process making devices.
In conclusion the soluble 8-hydroxyquinoline Zn complex crystal with one-dimensional catenary structure in DMSO with compared with
Good stability and solubility, can have can wet processing property；And there is relatively high luminous intensity and thermal stability, fit
Conjunction is used to prepare corresponding luminescent device.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention.For those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways.There is no necessity and possibility to exhaust all the enbodiments.It is all this
All any modification, equivalent and improvement etc., should be included in the claims in the present invention made by within the spirit and principle of invention
Protection domain within.
Claims (9)
1. a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure has the structure as shown in formula I：
2. a kind of preparation method of 8-hydroxyquinoline Zn complex described in claim 1, including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, obtain reaction intermediate；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc cooperation
Object.
3. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step a) is acetic anhydride.
4. preparation method according to claim 2, which is characterized in that the condition reacted described in step a) is：In inertia
It is heated to reflux under the protection of gas；
The inert gas is nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
5. preparation method according to claim 2, which is characterized in that in step b) after pyridine is added first heating stirring,
Then water is added to be heated at reflux.
6. preparation method according to claim 5, which is characterized in that the temperature of the heating stirring is 132~135 DEG C,
Time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
7. preparation method according to claim 2, which is characterized in that zinc salt is described in step c)：Zinc perchlorate, nitric acid
It is one or more in zinc and zinc chloride；
The molar ratio of the ligand and zinc salt is (3~5):(8~12).
8. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step c) is N, N- dimethyl
The mixed solution of formamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(100~150) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is (1~4):(0.5~2).
9. preparation method according to claim 2, which is characterized in that the temperature reacted described in step c) is 60~80
DEG C, the time is for 24 hours.
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