CN105418686A - Pyrazine phosphorescent iridium complex, preparation method and application thereof - Google Patents
Pyrazine phosphorescent iridium complex, preparation method and application thereof Download PDFInfo
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- CN105418686A CN105418686A CN201510987927.3A CN201510987927A CN105418686A CN 105418686 A CN105418686 A CN 105418686A CN 201510987927 A CN201510987927 A CN 201510987927A CN 105418686 A CN105418686 A CN 105418686A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention discloses a pyrazine phosphorescent iridium complex, a preparation method and an application thereof. The iridium complex is represented as the following chemical structure formula, wherein R1 is a C1-C6 alkyl group; and R2, R3, R4, R5, R6 and R7 independently are hydrogen or C1-C6 alkyl groups. According to the invention, when synthesis of the high-effective pyrazine tricyclic metal iridium complex is researched, a problem of requirement on column chromatography in after treatment of synthesis of the pyrazine iridium complex through a microwave method is solved. The pyrazine phosphorescent iridium complex has excellent effects when being used as an object material in a luminescent layer of a luminescent device.
Description
Technical field
The present invention relates to electromechanical phosphorescent material technical field, particularly relate to a kind of pyrazine phosphorescent iridium complex and its preparation method and application.
Background technology
Phosphor material octaethylporphyrin platinum (PtOEP) is entrained in Alq by Thomopson and F rrest in 1998 cooperation
3the middle luminescent layer as electroluminescent device, brings up to 4% and 23% respectively by external quantum efficiency and internal quantum efficiency, thus opens the frontier (Nature, 1998, vol.395,151-153) of electrophosphorescence.Since the early stage electrophosphorescence device taking PtOEP as twinkler demonstrates after electroluminescent device efficiency can be improved by the participation of the exciton of triplet state, research about electrophosphorescence material obtains development at full speed, Ir (III) title complex because phosphorescent lifetime is relatively short and luminous quantum efficiency is high, and becomes the focus of electroluminescent area research.
The principle of luminosity of organic electroluminescence device (OLED) is under forward voltage effect, and hole and electronics inject from anode and negative electrode respectively, and these two kinds of current carriers, through transmission compound in organic light emission merit layer, form exciton, produce radioluminescence.But in OLED, the electronic mobility of general organic materials is very low, and hole mobility is higher than electronic mobility, the electron-hole of such device inside is uneven, device efficiency can be caused to reduce, and efficiency decay is very fast, (the L.S.Hungetal such as stability reduction, Mater.Sci.Eng.R-Rep, 39 (2002) 143 – 222).Because pyrazine ligand has higher electron affinity than the pyridine only containing a nitrogen-atoms, be more suitable for as electron acceptor(EA) unit application in photoelectric material to improve electric transmission and the injection efficiency (MartinR.Bryceetal of material, J.Mater.Chem., 2005,15,94 – 107).Pyrazine complex of iridium, due to the impact of dinitrogen atom, has positive effect improving in the stability etc. of luminosity and title complex.We have done some researchs to Pyrazine complex of iridium, and delivered series of articles, and be obtained for good result (Guo Haiqing studying the luminescent device prepared under the level of understanding at that time, Zhang Guolin etc., SCI, (2004), Vol.25,397-400; Guo Haiqing, Zhang Guolin etc., Acta PhySico-Chimica Sinica, (2003), 19 (10): 889-891; HaiqingGuoetal, journaloforganometallicchemistry694 (2009) 3050-3057).The further research of luminescent device is being shown, is making the device of luminescent layer doping than Ir (C N) with three ring metal iridium complexes
2(acac) device doing to adulterate has higher stability, and device lifetime is longer, is more suitable for the application in fields such as illumination, displays.
Literature survey shows, synthesis Ir (C N)
3the article delivered of general people 2003 such as employing MarkE.Thompson etc. in method (J.Am.Chem.Soc. (2003), 125,7377-7387).But the several method in this article often walks generally needs 24 hours, and faces the problem that raw material is expensive or step is many.Meanwhile, the method in article also faces generation face formula and the problem through formula isomers, needs post or recrystallization to purify, and is unfavorable for industrial production.Although the people such as ShinAoki make the generation face-type structural of reaction preference by other method, need circulating reaction 3 times, every secondary response 24 hours, spent time long (ShinAokietal, Inorg.Chem. (2011), 50,806 – 818).Although HideoKonno etc. are to microwave method synthesis Ir (ppy)
3carry out preliminary study (ChemistryLetters (2003); Vol.32; No.3; 252); but the people such as Zhang Guolin effect when trial microwave method synthesis Pyrazine three ring metal iridium complex is bad, and aftertreatment needed post (Guo-linZhangetal, Chin.J.Chem.Phys. (2010); 23,355; License notification number CN101161663B).This shows, the reaction conditions of microwave method synthesis Pyrazine three ring metal iridium complex also needs further optimization, simplifies last handling process, makes its applicable industrial production.
Summary of the invention
The object of the invention is the novel phosphorescence Pyrazine complex of iridium in order to synthesize a class with different emission wavelength.
Another object of the present invention is to provide a kind of method preparing Pyrazine complex of iridium, its synthesis step is simple, and aftertreatment is simple.
Another object of the present invention is to provide the organic electroluminescence device of a kind of above-mentioned pyrazine complex of iridium as luminescent material, and device detection result shows it and has excellent over-all properties.
The present invention adopts following technical scheme:
The chemical structural formula of pyrazine phosphorescent iridium complex of the present invention is as follows:
Wherein, R
1to be carbonatoms be 1 to 6 alkyl; R
2, R
3, R
4, R
5, R
6, R
7separate is H or carbonatoms is the alkyl of 1 to 6.
As one of preferred technical scheme: complex of iridium of the present invention is that three (2-methyl-3-phenyl pyrazines) close iridium, and chemical structural formula is as follows:
The preparation method of pyrazine phosphorescent iridium complex of the present invention comprises the following steps:
(1) chloro-for 2-3-methylpyrazine or derivatives thereof and phenyl-boron dihydroxide or derivatives thereof are joined in glycol dimethyl ether, then add 2MK
2cO
3(aq) and four (triphenyl phosphorus) palladium, reflux, reaction times 16-24 hour, obtained pyrazine ligand (L), structure is as follows:
React as follows:
Wherein, R
1carbonatoms is the alkyl of 1 to 6; R
2, R
3, R
4, R
5, R
6, R
7separate is H or carbonatoms is the alkyl of 1 to 6.
(2) by IrCl
33H
2o, corresponding part (L) and solvent join in there-necked flask, and gained solution filters by Microwave-assisted firing 1 ~ 2 hour under nitrogen protection, by washing with alcohol precipitation, target product.
In step (1), the mol ratio of 2-chloro-3-methylpyrazine or derivatives thereof and phenyl-boron dihydroxide or derivatives thereof is 1:1.2 ~ 2.
In step (1), four (three base phosphorus palladiums) are 1:40 ~ 50 with the mol ratio of 2-chloro-3-methylpyrazine or derivatives thereof.
Glycol dimethyl ether and 2MK in step (1)
2cO
3 (aq) volume ratio is 1:1 ~ 1.5.
IrCl in step (2)
33H
2the mol ratio of O and pyrazine ligand is 1:50 ~ 200.
In step (2), solvent for use is at least one in ethylene glycol, BDO.
In step (2), 1mmol pyrazine ligand adds the volume of solvent is 3 ~ 10ml.
Step (2) Heating temperature 200-230 DEG C.
Because pyrazine ligand has higher electron affinity than the pyridine only containing a nitrogen-atoms, be more suitable for as electron acceptor(EA) unit application in photoelectric material to improve electric transmission and the injection efficiency of material, so Pyrazine complex of iridium generally has higher luminescent properties.The present invention passes through the new Pyrazine phosphorescent iridium complex of design and synthesis, obtains the Pyrazine phosphorescent iridium complex of different emission wavelength, and successful optimum synthesis condition and last handling process, make its applicable industrial production.
Synthesis step is: be obtained by reacting pyrazine ligand by Suzuki, by pyrazine ligand, IrCl
33H
2o and glycolic solvents under nitrogen protection Microwave-assisted firing are obtained by reacting target product.
In addition, pyrazine phosphorescent iridium complex of the present invention can be used as the organic electroluminescence device of luminescent material, as the guest materials of the luminescent layer of organic electroluminescence device.
The invention provides a kind of electroluminescent device, comprise Conducting Glass layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, cathode layer, the luminescent material of luminescent layer comprises pyrazine phosphorescent iridium complex of the present invention.
Positively effect of the present invention is as follows:
The present invention is when studying synthesizing efficient rate Pyrazine complex of iridium, solve the problem that the aftertreatment of microwave method synthesis Pyrazine complex of iridium needed post simultaneously, the pyrazine phosphorescent iridium complex synthesized the most at last is used as the guest materials in the luminescent layer of emitting components, achieves very well comparatively fruit.
The present invention, by changing the substituting group of part, changes the level structure of material, obtains the Pyrazine phosphorescent iridium complex with different emission.Because pyrazine ligand has higher electron affinity than the pyridine only containing a nitrogen-atoms, be more suitable for as electron acceptor(EA) unit application in photoelectric material to improve electric transmission and the injection efficiency of material, so Pyrazine complex of iridium generally has higher luminescent properties, facilitate its practical and commercialization process.
In addition, adopt Microwave-assisted firing can obtain target phosphorescent iridium complex fast, experimental period and save energy can be shortened.Meanwhile, the part in experiment and solvent can recycle, and are eco-friendly, meet the environmental protection policy that National Industrial is produced, facilitate its process of industrialization.
Accompanying drawing explanation
Fig. 1 is yellow phosphorescence pyrazine complex of iridium Ir (MPPZ) provided by the invention
3at CH
2cl
2in ultraviolet-visible absorption spectroscopy figure;
Fig. 2 is yellow phosphorescence complex of iridium Ir (MPPZ) provided by the invention
3at CH
2cl
2in photoluminescence spectra (ex=330nm);
Fig. 3 is yellow phosphorescence pyrazine complex of iridium Ir (MPPZ) provided by the invention
3nuclear magnetic spectrogram;
Fig. 4 is the organic electroluminescence device structural representation of example 5;
Fig. 5 is the electroluminescent spectrum of the organic electroluminescence device of example 5;
Fig. 6 is the Current density-voltage-brightness collection of illustrative plates of the organic electroluminescence device of example 5;
Fig. 7 is the device brightness-power efficiency collection of illustrative plates of the organic electroluminescence device of example 5;
Fig. 8 is the current efficiency-current density collection of illustrative plates of the organic electroluminescence device of example 5.
Embodiment
The following examples describe in further detail of the present invention.
Embodiment 1: three (2-methyl-3-phenyl pyrazines) closes the synthesis of iridium, called after Ir (MPPZ)
3
Concrete structure formula is as follows:
(1) preparation of 2-methyl-3-phenyl pyrazines (MPPZ):
In 1000ml there-necked flask, add the chloro-3-methylpyrazine of 32.25g2-, 36.57g phenyl-boron dihydroxide, 250ml glycol dimethyl ether, 6.01g tetra-(triphenyl phosphorus) palladium successively, 340ml2MK
2cO
3(aq), under nitrogen protection, reflux 18 hours, is cooled to room temperature, is extracted with ethyl acetate, anhydrous magnesium sulfate drying, revolve steaming.Tlc take silica gel as stationary phase, by ethyl acetate: sherwood oil=1:4 crosses post, obtains 33.51 grams of 2-methyl-3-phenyl pyrazines (MPPZ), yield 78%.
(2) microwave method boosting synthesis Ir (MPPZ)
3
By 0.101 gram of IrCl
33H
2o, 5.0 grams of MPPZ, 20ml ethylene glycol in 50ml there-necked flask, Microwave-assisted firing 220 under nitrogen protection
oreact 1 hour under C, gained solution is filtered, reclaim filtrate.Precipitation washing with alcohol, obtains 0.161 gram of Ir (MPPZ)
3.Yield 80%.
Fig. 1 is target product Ir (MPPZ)
3at CH
2cl
2in ultraviolet-visible absorption spectroscopy figure, therefrom visible, described title complex Ir (MPPZ)
3three absorption peaks are had at about 240nm, 320nm and 400nm.
Fig. 2 is target product Ir (MPPZ)
3at CH
2cl
2in photoluminescence spectra (ex=330nm), therefrom visible, described title complex Ir (MPPZ)
3emission peak be positioned at 580nm.
Fig. 3 is products therefrom
1hNMR nuclear magnetic spectrogram, its result shows that structure is correct, and data are as follows:
1HNMR(300MHz,CDCl
3)δ(ppm)=8.00(d,9H),7.30(d,3H),7.01(t,3H),6.88(d,3H),6.78(d,3H),3.06(s,9H)。
Embodiment 2: three (2-methyl-3-(4-aminomethyl phenyl) pyrazine) closes the synthesis of iridium
Concrete structure formula is as follows:
(1) preparation of 2-methyl-3-(4-aminomethyl phenyl) pyrazine:
In 250ml there-necked flask, add the chloro-3-methylpyrazine of 6.45g2-, 8.14g p-methylphenyl boric acid, 50ml glycol dimethyl ether, 1.20g tetra-(triphenyl phosphorus) palladium successively, 68ml2MK
2cO
3(aq), under nitrogen protection, reflux 18 hours, is cooled to room temperature, is extracted with ethyl acetate, anhydrous magnesium sulfate drying, revolve steaming.Tlc take silica gel as stationary phase, by ethyl acetate: sherwood oil=1:4 crosses post, obtains 6.78 grams of target products (1), yield 73%.
(2) microwave method boosting synthesis three (2-methyl-3-(4-aminomethyl phenyl) pyrazines) close iridium
By 0.101 gram of IrCl
33H
2o, 5.5 grams of 2-methyl-3-(4-aminomethyl phenyl) pyrazines (1), 20ml ethylene glycol in 50ml there-necked flask, Microwave-assisted firing 220 under nitrogen protection
oreact 1 hour under C, gained solution is filtered, reclaim filtrate.Precipitation washing with alcohol, obtains 0.175 gram of target product (2), yield 83%.
Embodiment 3: three (2-methyl-3-(4-ethylphenyl) pyrazine) closes the synthesis of iridium
Concrete structure formula is as follows:
(1) preparation of 2-methyl-3-(4-ethylphenyl) pyrazine:
In 250ml there-necked flask, add the chloro-3-methylpyrazine of 6.45g2-, 9.01g successively to ethylphenyl boric acid, 50ml glycol dimethyl ether, 1.20g tetra-(triphenyl phosphorus) palladium, 68ml2MK
2cO
3(aq), under nitrogen protection, reflux 18 hours, is cooled to room temperature, is extracted with ethyl acetate, anhydrous magnesium sulfate drying, revolve steaming.Tlc take silica gel as stationary phase, by ethyl acetate: sherwood oil=1:4 crosses post, obtains 7.05 grams of target products (3), yield 71%.
(2) microwave method boosting synthesis three (2-methyl-3-(4-ethylphenyl) pyrazines) close iridium
By 0.101 gram of IrCl
33H
2o, 5.5 grams of 2-methyl-3-(4-ethylphenyl) pyrazines (3), 20ml ethylene glycol in 50ml there-necked flask, Microwave-assisted firing 220 under nitrogen protection
oreact 1 hour under C, gained solution is filtered, reclaim filtrate.Precipitation washing with alcohol, obtains 0.178 gram of target product (4), yield 79%.
Embodiment 4: three (2-methyl-3-(4-tert-butyl-phenyl) pyrazine) closes the synthesis of iridium
(1) preparation of 2-methyl-3-(4-tert-butyl-phenyl) pyrazine:
In 250ml there-necked flask, add the chloro-3-methylpyrazine of 6.45g2-, 10.68g4-tert-butylphenylboronic acid, 50ml glycol dimethyl ether, 1.21g tetra-(triphenyl phosphorus) palladium successively, 70ml2MK
2cO
3(aq), under nitrogen protection, reflux 18 hours, is cooled to room temperature, is extracted with ethyl acetate, anhydrous magnesium sulfate drying, revolve steaming.Tlc take silica gel as stationary phase, by ethyl acetate: sherwood oil=1:4 crosses post, obtains 9.07 grams of target products (5), yield 80%.
(2) microwave method boosting synthesis three (2-methyl-3-(4-tert-butyl-phenyl) pyrazines) close iridium
By 0.101 gram of IrCl
33H
2o, 5.5 grams of parts (5), 20ml ethylene glycol in 50ml there-necked flask, Microwave-assisted firing 220 under nitrogen protection
oreact 1.5 hours under C, gained solution is filtered, reclaim filtrate.Precipitation washing with alcohol, obtains 0.21 gram of target product (6), yield 85%.
Embodiment 5: the present embodiment is organic electroluminescence device, adopts the Ir (MPPZ) of embodiment 1
3as the guest materials of luminescent layer
Organic electroluminescence device preparation and test parameter document (OrganicElectronics, (2014), 15,926 – 936).Concrete grammar is: (be less than 7 × 10 in high vacuum
-5pa) under condition, deposition of hole transport material, luminescent material, hole barrier materials, electron transport material and cathode material successively on ITO substrate.Before fabricate devices, ITO need clean successively, dry and ozonize.Device architecture obtained is in this way as follows: ITO/NPB (40nm)/Ir (MPPZ)
3: CBP (8%, 30nm)/TPBI (15nm)/Alq
3(30nm)/LiF (1nm)/Al (100nm), refers to the structural representation of Fig. 4.
Wherein, tin indium oxide (ITO) is as anode; N, N '-phenylbenzene-N, N '-(1-how base) 4,4 '-benzidine (NPB) is as hole injection layer; 4,4'-bis-(9-carbazole) biphenyl (CBP) as the material of main part of luminescent layer, Ir (MPPZ)
3as the guest materials of luminescent layer; 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene (TPBI) is as hole barrier materials and electron transport material; Oxine aluminium (Alq
3) as electron transfer layer; Lithium fluoride (LiF) is as electron injecting layer; Aluminium (Al) is as negative electrode.
Fig. 5 adopts title complex Ir (MPPZ)
3as the electroluminescent spectrum of the organic electroluminescence device of luminescent material, therefrom visible, the emission peak of described organic electroluminescence device is positioned at 556nm.
Fig. 6 adopts title complex Ir (MPPZ)
3as the Current density-voltage-height collection of illustrative plates of the organic electroluminescence device of luminescent material, the trigger voltage of described organic electroluminescence device is 2.4V, and when driving voltage reaches 10V, maximum luminosity reaches 115000cd/m
2.
Fig. 7 adopts title complex Ir (MPPZ)
3as the device brightness-power efficiency collection of illustrative plates of the organic electroluminescence device of luminescent material, therefrom visible, at 1000cd/m
2time, the power efficiency of device is 33lm/W.
Fig. 8 adopts title complex Ir (MPPZ)
3as the current efficiency-current density collection of illustrative plates of the organic electroluminescence device of luminescent material, therefrom visible, the maximum current efficiency of described organic electroluminescence device is 33cd/A.
In sum, the present invention, by changing the substituting group of part, changes the level structure of material, obtains the complex of iridium with different emission peak.Because pyrazine ligand has higher electron affinity than the pyridine only containing a nitrogen-atoms, be more suitable for as electron acceptor(EA) unit application in photoelectric material to improve electric transmission and the injection efficiency of material, so Pyrazine complex of iridium generally has higher luminescent properties, facilitate its practical and commercialization process.
In addition, adopt Microwave-assisted firing can obtain target phosphorescent iridium complex fast, experimental period and save energy can be shortened.Meanwhile, the part in experiment and solvent can recycle, and are eco-friendly, meet the environmental protection policy that National Industrial is produced, facilitate its process of industrialization.
Although illustrate and describe embodiments of the invention, for the ordinary skill in the art, be appreciated that and can carry out multiple change, amendment, replacement and modification to these embodiments without departing from the principles and spirit of the present invention, scope of the present invention is by claims and equivalents thereof.
Claims (10)
1. a pyrazine phosphorescent iridium complex, is characterized in that: the chemical structural formula of described complex of iridium is as follows:
Wherein, R
1to be carbonatoms be 1 to 6 alkyl; R
2, R
3, R
4, R
5, R
6, R
7separate is H or carbonatoms is the alkyl of 1 to 6.
2. pyrazine phosphorescent iridium complex as claimed in claim 1, is characterized in that: described complex of iridium is that three (2-methyl-3-phenyl pyrazines) close iridium, and chemical structural formula is as follows:
。
3. prepare a method for pyrazine phosphorescent iridium complex as claimed in claim 1 or 2, it is characterized in that: comprising the following steps of described method:
(1) chloro-for 2-3-methylpyrazine or derivatives thereof and phenyl-boron dihydroxide or derivatives thereof are joined in glycol dimethyl ether, then add four (triphenyl phosphorus) palladium and 2MK
2cO
3(aq), reflux, reaction times 16-24 hour, obtained pyrazine ligand;
(2) by IrCl
33H
2o, pyrazine ligand and solvent join in reactor, Microwave-assisted firing 1 ~ 2 hour under nitrogen protection, are filtered by gained solution, by washing with alcohol precipitation, obtain target product.
4. preparation method as claimed in claim 3, it is characterized in that: in step (1), the mol ratio of 2-chloro-3-methylpyrazine or derivatives thereof and phenyl-boron dihydroxide or derivatives thereof is 1:1.2 ~ 2; Four (three base phosphorus palladiums) are 1:40 ~ 50 with the mol ratio of 2-chloro-3-methylpyrazine or derivatives thereof; Glycol dimethyl ether and 2MK
2cO
3(aq) volume ratio is 1:1 ~ 1.5.
5. preparation method as claimed in claim 3, is characterized in that: in step (2), IrCl
33H
2the mol ratio of O and pyrazine ligand is 1:50 ~ 200, and the volume that 1mmol pyrazine ligand correspondence adds solvent is 3 ~ 10ml.
6. preparation method as claimed in claim 3, it is characterized in that: in step (2), described solvent is at least one in ethylene glycol, BDO.
7. preparation method as claimed in claim 3, it is characterized in that: in step (2), Microwave-assisted firing temperature is 200-230 DEG C.
8. pyrazine phosphorescent iridium complex as claimed in claim 1 or 2 is used as the application of the organic electroluminescence device of luminescent material.
9. apply as claimed in claim 8, it is characterized in that: pyrazine phosphorescent iridium complex is used as the guest materials of the luminescent layer of organic electroluminescence device.
10. an electroluminescent device, comprises Conducting Glass layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, cathode layer, is characterized in that: the luminescent material of luminescent layer comprises the pyrazine phosphorescent iridium complex as described in the claims in the present invention 1 or 2.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108219791A (en) * | 2018-01-26 | 2018-06-29 | 温州大学 | A kind of fluorescent crystal material and its preparation process flow based on rare earth oxide |
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