CN104059630A - Novel red phosphorescent material and synthetic method thereof - Google Patents
Novel red phosphorescent material and synthetic method thereof Download PDFInfo
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- CN104059630A CN104059630A CN201310111762.4A CN201310111762A CN104059630A CN 104059630 A CN104059630 A CN 104059630A CN 201310111762 A CN201310111762 A CN 201310111762A CN 104059630 A CN104059630 A CN 104059630A
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- bromo
- phenylpyridine
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Abstract
The invention discloses a novel red phosphorescent material which has a structural formula as shown in the description. The red phosphorescent material of the invention has the advantages that: metal iridium complex is introduced into the red phosphorescent material, which improves the rigidity and stability of the phosphorescent material, and a beta-heptadione ligand is introduced, which improves the dissolvability of the iridium complex phosphorescent material, thereby enabling the phosphorescent material to be easier to coat and process. Meanwhile, the material also exhibits good thermal stability. In the meantime, a bromine-containing group is introduced into the structure, which enables the material to be subjected to copolymerization with other compounds with special functional groups, and thus enables the material to be used as a polymerization monomer for preparation of polymer luminescent materials. In addition, the synthetic method is simple, and strong in practicality, and the material can be used as a red phosphorescent material and used in luminescent materials.
Description
Technical field
The invention belongs to photoelectric material technical field, relate in particular to a kind of novel red phosphorescence material and synthetic method thereof.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide, easily realizes the advantages such as resolving power is high, lightweight, large-area flat-plate demonstration, is described as " 21 century flat panel display ".Organic electromechanical phosphorescent material can utilize singlet and Triplet exciton simultaneously, has luminous efficiency advantages of higher, becomes the focus of Recent study.
With respect to high-performance and ripe green and blue phosphorescent material day by day, the progress of red light material is obviously backward.Early stage representative complexes of red light iridium is from the Btp of Forrest group design
2ir (acac), glow peak is positioned at 616nm, and its maximum external quantum efficiency reaches 7% left and right.2005, Rayabrapu D K developed 3 kinds of red phosphorescence material based on alkane thiazolinyl quinoline, and the glow peak of its device is positioned at 620-650nm, and external quantum efficiency reaches as high as 7.23%, and luminosity is 26400cd/m
2, the design that is developed as phosphor material of this type of material provides thinking (Adv Mater., 2005,17:349-353).
Still there is the problem that luminous quantum efficiency is low, purity of color is poor in red phosphorescent complex of iridium at present.The main cause of this situation is because the red light comes from the energy gap between the energy of a narrow jump , while the heavy metal complexes of narrow band gap in the design of ligands certain difficulties, the second red light in the material system there is a strong PI PI bond interaction, between ligand charge transfer characteristics of a strong, so that the narrow band gap exists in more radiationless relaxation channel, intensified quenching for phosphor, reduces the amount of red light system when zi chan rate.Therefore the red phosphorescence material of the synthetic high comprehensive performance of design, will become the important topic of electroluminescent organic material research.
Summary of the invention
The object of the invention is to, provide a kind of complex of iridium that contains with good stability, film-forming properties and luminescent properties, for red phosphorescence material provides new alternative kind.
Novel red phosphorescence material structural formula of the present invention is:
Described red phosphorescence material is reacted and is made with β-heptadione by complex of iridium dimer under the condition of protection of inert gas, and solvent for use is ethylene glycol ethyl ether or N-Methyl pyrrolidone, and alkali is Na
2cO
3or K
2cO
3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 125-130 DEG C, the reaction times is 16-24h.
Described complex of iridium dimer is 4-(the bromo-thiophene of 4-)-phenylpyridine iridium dimer; make under the condition of protection of inert gas by 4-(the bromo-thiophene of 4-)-phenylpyridine and three hydration iridium chlorides; solvent for use is ethylene glycol ethyl ether; rare gas element is nitrogen; temperature of reaction is 125-130 DEG C, reaction times 24-30h.
Described 4-(the bromo-thiophene of 4-)-phenylpyridine, makes under the condition of protection of inert gas by the bromo-phenylpyridine boric acid of 4-and 2,5-dibromo thiophene, and solvent for use is toluene or dimethylbenzene, and catalyzer is Pd (PPh
3)
4, alkali is Na
2cO
3or K
2cO
3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 95-105 DEG C, reaction times 24-36h.
The bromo-phenylpyridine boric acid of described 4-, makes under the condition of protection of inert gas by the bromo-phenylpyridine of 4-and trimethyl borate, and reaction solvent is anhydrous THF; catalyzer is n-Butyl Lithium reagent; rare gas element is nitrogen, and temperature of reaction is subzero 50-78 DEG C, reaction times 12h.
By fluorescence, ultraviolet spectrometer is characterized its Photophysics, by the thermostability of thermogravimetric analysis test material.
Compared with prior art, the invention has the advantages that, described red phosphorescence material is near the saturated red phosphorescence material of a kind of emission wavelength 650nm.Introduce metal iridium complex, increased rigidity and the stability of phosphor material, introduced β-heptadione ligand simultaneously and improved the solvability of iridium complex phosphorescence material, thereby make this kind of phosphor material be easier to apply processing.In addition, its structure has been introduced band bromine group, can with other compound copolymerization with specific function group, therefore also can be used as polymerization single polymerization monomer and prepare polymer luminescent material.
Brief description of the drawings
Fig. 1 is the synthesis path of this red phosphorescence material;
Fig. 2 is the thermogravimetric curve of the prepared red phosphorescence material of embodiment 1.
Fig. 3 is the uv absorption spectra of the prepared red phosphorescence material of embodiment 1;
Fig. 4 is the fluorescence pattern of the prepared red phosphorescence material of embodiment 1.
Embodiment
Further illustrate synthetic (synthetic route is shown in Fig. 1) and the mensuration of physicals of red phosphorescence material of the present invention below by embodiment.
Embodiment 1:
(1) take the bromo-phenylpyridine (10g of 4-; 0.041mol) add in 150mL tri-neck round-bottomed flasks; under nitrogen protection, add 50mL tetrahydrofuran (THF) (by the sodium drying treatment that refluxes); system is placed in to ice bath (acetone-dry ice), keeps anhydrous and oxygen-free.In the time that temperature is down to approximately-78 DEG C, n-Butyl Lithium (24mL, 2.5M, 0.06mol) is splashed into reaction system slowly, the about 30min of whole process.Add rear maintenance temperature and stir 1h, then trimethyl borate (6.93mL, 0.06mol) is splashed into system slowly, after, at-78 DEG C of stable 2h that stir.Stop temperature control, equitemperature continues reaction 6h after rising to room temperature, and the termination reaction that adds water is acid with dilute hydrochloric acid modulation, continues to stir 2h.Tetrahydrofuran (THF) is removed in underpressure distillation, adds subsequently sodium chloride saturated solution, obtains the bromo-phenylpyridine boric acid of 4-, productive rate 80%.
(2) take the bromo-phenylpyridine boric acid of 4-(4g, 0.02mol), 2,5-dibromo thiophene (4.8g, 2.24mL0.02mol), Pd (PPh
3)
4(0.231g, 0.2mmol, 1%), K
2cO
3the aqueous solution (8g, 20mL), toluene (80mL) is placed in the three neck round-bottomed flasks of 150mL, is warming up to 95 DEG C, in the atmosphere of nitrogen, stirs 24h.After reaction finishes, be cooled to room temperature, remove by filter the indissoluble material in mixture, with the separating funnel extraction that adds water, remove water layer, the solvent in organic layer is removed in underpressure distillation, subsequently using methylene dichloride: sherwood oil=10: 1 as leacheate, obtain 4-(the bromo-thiophene of 4-)-phenylpyridine, productive rate 80% with silica gel column chromatography separating purification.
(3) take 4-(the bromo-thiophene of 4-)-phenylpyridine (1.3g, 4.12mmol), IrCl
33H
2o (0.52g, 1.64mmol) adds in the round-bottomed flask of 100mL, adds subsequently ethylene glycol ethyl ether (45mL), H2O (15mL).Be warming up to 125 DEG C, lucifuge stirs 24h in the atmosphere of nitrogen.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless, obtains 4-(the bromo-thiophene of 4-)-thick product of phenylpyridine iridium dimer.
(4) take 4-(the bromo-thiophene of 4-)-phenylpyridine iridium dimer (1.18g, 0.69mmol), 2,2,6,6-tetramethyl--3,5-heptadione (0.317g, 1.72mmol0.36mL), Na
2cO
3(0.365g, 3.44mmol) adds in 100mL round-bottomed flask, adds subsequently ethylene glycol ethyl ether 40mL, is warming up to 125 DEG C, and lucifuge stirs 16h in the atmosphere of anhydrous and oxygen-free.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless.Use subsequently methylene dichloride and sherwood oil recrystallization, tentatively remove insoluble impurity, taking toluene: sherwood oil=2: 1 as leacheate, obtain red phosphorescence material, productive rate 50% with alumina column separation and purification.
Embodiment 2:
(1) take the bromo-phenylpyridine (10g of 4-; 0.041mol) add in 150mL tri-neck round-bottomed flasks; under nitrogen protection, add 50mL tetrahydrofuran (THF) (by the sodium drying treatment that refluxes); system is placed in to ice bath (acetone-dry ice), keeps anhydrous and oxygen-free.In the time that temperature is down to approximately-78 DEG C, n-Butyl Lithium (24mL, 2.5M, 0.06mol) is splashed into reaction system slowly, the about 30min of whole process.Add rear maintenance temperature and stir 1h, then trimethyl borate (6.93mL, 0.06mol) is splashed into system slowly, after, at-78 DEG C of stable 2h that stir.Stop temperature control, equitemperature continues reaction 6h after rising to room temperature, and the termination reaction that adds water is acid with dilute hydrochloric acid modulation, continues to stir 2h.Tetrahydrofuran (THF) is removed in underpressure distillation, adds subsequently sodium chloride saturated solution, obtains the bromo-phenylpyridine boric acid of 4-, productive rate 80%.
(2) take the bromo-phenylpyridine boric acid of 4-(4g, 0.02mol), 2,5-dibromo thiophene (4.8g, 2.24mL0.02mol), Pd (PPh
3)
4(0.231g, 0.2mmol, 1%), K
2cO
3the aqueous solution (8g, 20mL), toluene (80mL) is placed in the three neck round-bottomed flasks of 150mL, is warming up to 105 DEG C, in the atmosphere of nitrogen, stirs 24h.After reaction finishes, be cooled to room temperature, remove by filter the indissoluble material in mixture,, with the separating funnel extraction that adds water, remove water layer, the solvent in organic layer is removed in underpressure distillation, subsequently using methylene dichloride: sherwood oil=10: 1 as leacheate, obtain 4-(the bromo-thiophene of 4-)-phenylpyridine, productive rate 82% with silica gel column chromatography separating purification.
(3) take 4-(the bromo-thiophene of 4-)-phenylpyridine (1.3g, 4.12mmol), IrCl
33H
2o (0.52g, 1.64mmol) adds in the round-bottomed flask of 100mL, adds subsequently ethylene glycol ethyl ether (45mL), H
2o (15mL).Be warming up to 130 DEG C, lucifuge stirs 30h in the atmosphere of nitrogen.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless, obtains 4-(the bromo-thiophene of 4-)-thick product of phenylpyridine iridium dimer.
(4) take 4-(the bromo-thiophene of 4-)-phenylpyridine iridium dimer (1.18g, 0.69mmol), 2,2,6,6-tetramethyl--3,5-heptadione (0.317g, 1.72mmol0.36mL), Na
2cO
3(0.365g, 3.44mmol) adds in 100mL round-bottomed flask, adds subsequently ethylene glycol ethyl ether 40mL, is warming up to 130 DEG C, and lucifuge stirs 24h in the atmosphere of anhydrous and oxygen-free.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless.Use subsequently methylene dichloride and sherwood oil recrystallization, tentatively remove insoluble impurity, taking toluene: sherwood oil=2: 1 as leacheate, obtain red phosphorescence material, productive rate 58% with alumina column separation and purification.Other and embodiment 1 are similar.
Embodiment 3:
(1) take the bromo-phenylpyridine (10g of 4-; 0.041mol) add in 150mL tri-neck round-bottomed flasks; under nitrogen protection, add 50mL tetrahydrofuran (THF) (by the sodium drying treatment that refluxes); system is placed in to ice bath (acetone-dry ice), keeps anhydrous and oxygen-free.In the time that temperature is down to approximately-78 DEG C, n-Butyl Lithium (24mL, 2.5M, 0.06mol) is splashed into reaction system slowly, the about 30min of whole process.Add rear maintenance temperature and stir 1h, then trimethyl borate (6.93mL, 0.06mol) is splashed into system slowly, after, at-78 DEG C of stable 2h that stir.Stop temperature control, equitemperature continues reaction 6h after rising to room temperature, and the termination reaction that adds water is acid with dilute hydrochloric acid modulation, continues to stir 2h.Tetrahydrofuran (THF) is removed in underpressure distillation, adds subsequently sodium chloride saturated solution, obtains the bromo-phenylpyridine boric acid of 4-, productive rate 80%.
(2) take the bromo-phenylpyridine boric acid of 4-(4g, 0.02mol), 2,5-dibromo thiophene (4.8g, 2.24mL0.02mol), Pd (PPh
3)
4(0.231g, 0.2mmol, 1%), K
2cO
3the aqueous solution (8g, 20mL), toluene (80mL) is placed in the three neck round-bottomed flasks of 150mL, is warming up to 95 DEG C, in the atmosphere of nitrogen, stirs 36h.After reaction finishes, be cooled to room temperature, remove by filter the indissoluble material in mixture, with the separating funnel extraction that adds water, remove water layer, the solvent in organic layer is removed in underpressure distillation, subsequently using methylene dichloride: sherwood oil=10: 1 as leacheate, obtain 4-(the bromo-thiophene of 4-)-phenylpyridine, productive rate 82% with silica gel column chromatography separating purification.
(3) take 4-(the bromo-thiophene of 4-)-phenylpyridine (1.3g, 4.12mmol), IrCl
33H
2o (0.52g, 1.64mmol) adds in the round-bottomed flask of 100mL, adds subsequently ethylene glycol ethyl ether (45mL), H
2o (15mL).Be warming up to 125 DEG C, lucifuge stirs 24h in the atmosphere of nitrogen.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless, obtains 4-(the bromo-thiophene of 4-)-thick product of phenylpyridine iridium dimer.
(4) take 4-(the bromo-thiophene of 4-)-phenylpyridine iridium dimer (1.18g, 0.69mmol), 2,2,6,6-tetramethyl--3,5-heptadione (0.317g, 1.72mmol0.36mL), Na
2cO
3(0.365g, 3.44mmol) adds in 100mL round-bottomed flask, adds subsequently N-Methyl pyrrolidone 40mL, is warming up to 125 DEG C, and lucifuge stirs 16h in the atmosphere of anhydrous and oxygen-free.After reaction finishes, be cooled to room temperature, underpressure distillation is except desolventizing, and underpressure distillation is except desolventizing, and the sedimentation that adds water, filters, and filter cake is washed till filtrate with methyl alcohol and is colourless.Use subsequently methylene dichloride and sherwood oil recrystallization, tentatively remove insoluble impurity, taking toluene: sherwood oil=2: 1 as leacheate, obtain product, productive rate 45% with alumina column separation and purification.Other and embodiment 1 are similar.
Embodiment 4:
Other synthesize 4-(the bromo-thiophene of 4-)-phenylpyridine with embodiment 1, and solvent for use is dimethylbenzene, and alkali is Na
2cO
3, other and embodiment 1 are that similarly productive rate is 76%.
Embodiment 5:
Other synthesize described red phosphorescence material with embodiment 1, and solvent for use is N-Methyl pyrrolidone, and alkali is K
2cO
3, other and embodiment 1 are that similarly productive rate is 52%.
Embodiment 6: by fluorescence, ultraviolet spectrometer is characterized its Photophysics, by the thermostability of thermogravimetric analysis test material.Figure of description is shown in by collection of illustrative plates.
Claims (5)
1. a red phosphorescent luminescent material, its structural formula is:
2. the synthetic method of a novel red phosphorescence material; it is characterized in that: described red phosphorescence material is reacted and made with β-heptadione by complex of iridium dimer under the condition of protection of inert gas; solvent for use is ethylene glycol ethyl ether or N-Methyl pyrrolidone, and alkali is Na
2cO
3or K
2cO
3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 125-130 DEG C, the reaction times is 16-20h.
3. the synthetic method of a kind of novel red phosphorescence material according to claim 2; it is characterized in that: complex of iridium dimer is 4-(the bromo-thiophene of 4-)-phenylpyridine iridium dimer; make under the condition of protection of inert gas by 4-(the bromo-thiophene of 4-)-phenylpyridine and three hydration iridium chlorides; solvent for use is ethylene glycol ethyl ether; rare gas element is nitrogen; temperature of reaction is 125-130 DEG C, reaction times 24-30h.
4. the synthetic method of a kind of novel red phosphorescence material according to claim 3; it is characterized in that: 4-(the bromo-thiophene of 4-)-phenylpyridine is by the bromo-phenylpyridine boric acid of 4-and 2; 5-dibromo thiophene makes under the condition of protection of inert gas; solvent for use is toluene or dimethylbenzene, and catalyzer is Pd (PPh
3)
4, alkali is Na
2cO
3or K
2cO
3the aqueous solution, rare gas element is nitrogen, temperature of reaction is 95-105 DEG C, reaction times 24-36h.
5. the synthetic method of described a kind of novel red phosphorescence material according to claim 4; it is characterized in that: the bromo-phenylpyridine boric acid of 4-makes under the condition of protection of inert gas by 4-(the bromo-thiophene of 4-)-phenylpyridine and trimethyl borate; reaction solvent is anhydrous THF; catalyzer is n-Butyl Lithium reagent; rare gas element is nitrogen; temperature of reaction is subzero 50-78 DEG C, reaction times 12h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859787A (en) * | 2015-01-20 | 2016-08-17 | 上海和辉光电有限公司 | Soluble phosphorescence OLED material and polymer used as luminescent material |
| CN113801170A (en) * | 2021-10-14 | 2021-12-17 | 东莞理工学院 | Bromine atom modified blue light absorption enhanced iridium (III) complex and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101186624A (en) * | 2007-08-16 | 2008-05-28 | 清华大学 | Iridium metal complex and application thereof |
| CN102516310A (en) * | 2011-10-26 | 2012-06-27 | 中国科学院苏州纳米技术与纳米仿生研究所 | Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application |
-
2013
- 2013-03-19 CN CN201310111762.4A patent/CN104059630B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101186624A (en) * | 2007-08-16 | 2008-05-28 | 清华大学 | Iridium metal complex and application thereof |
| CN102516310A (en) * | 2011-10-26 | 2012-06-27 | 中国科学院苏州纳米技术与纳米仿生研究所 | Cyclometalated iridium complex organic electrophosphorescent material, its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| HONGYU ZHEN 等: "Novel light-emitting electrophosphorescent copolymers based on carbazole with an Ir complex on the backbone", 《J. MATER. CHEM.》, vol. 17, 30 March 2007 (2007-03-30) * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105859787A (en) * | 2015-01-20 | 2016-08-17 | 上海和辉光电有限公司 | Soluble phosphorescence OLED material and polymer used as luminescent material |
| CN113801170A (en) * | 2021-10-14 | 2021-12-17 | 东莞理工学院 | Bromine atom modified blue light absorption enhanced iridium (III) complex and preparation method thereof |
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