CN100532385C - Organic electrofluorescent iridium complex material - Google Patents
Organic electrofluorescent iridium complex material Download PDFInfo
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- CN100532385C CN100532385C CNB2007100485638A CN200710048563A CN100532385C CN 100532385 C CN100532385 C CN 100532385C CN B2007100485638 A CNB2007100485638 A CN B2007100485638A CN 200710048563 A CN200710048563 A CN 200710048563A CN 100532385 C CN100532385 C CN 100532385C
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Abstract
The present invention is organic electrofluorescent iridium complex material in the structure as shown and with radical possessing great steric hindrance introduced to the ligand. The organic electrofluorescent iridium complex material has reduced influence on the light emitting efficiency of device caused by phosphorescence quenching and phosphorescence life one time lowered than available similar material.
Description
Technical field
The invention belongs to the organic electromechanical phosphorescent material field, particularly organic electrofluorescent iridium complex material and synthetic method thereof.
Background technology
Organic electromechanical phosphorescent material can significantly improve luminous efficiency owing to can effectively utilize triplet exciton, therefore is subjected to extensive concern.1999, the Thompson professor of American South University of California and professor Forrest of Princeton University closed iridium (III) with three (2-phenylpyridines) and [are abbreviated as Ir (ppy)
3] being doped to 4,4 '-N is made into the green glow electro phosphorescent device in the N-two carbazole biphenyl (being abbreviated as BCP), and its highest external quantum efficiency reaches 8.0%[and sees Baldo M A, Lamansky S, BurrowsP E, Thompson M E, Forrest S R, Appl.Phys.Lett.1999,11,3709].Continue after, people such as Thompson have reported a series ofly have than the short (compound (C^N) that contains cyclic metal complexes (C^N) and single anion bidentate assistant ligand (LX) of phosphorescent lifetime τ=1～14us) of strong room temperature phosphorescence and phosphorescent lifetime
2Ir (LX).Owing to utilize short life triplet state luminescent material as the transmission ofenergy acceptor, the transmission ofenergy that can overcome between the subject and object luminescent material under high current density is obstructed, thereby solved the problem of device luminescent saturation degree under the high current density, therefore improved the business-like possibility of organic electro phosphorescent device greatly.
In recent years, heavy metal complex, particularly the performance study of the exploitation of complex of iridium class electromechanical phosphorescent material and device has become the focus of present organic electroluminescent area research.Wherein, methyl ethyl diketone root two (2-phenyl benzothiazole root) closes iridium (III) and [is abbreviated as (bt)
2Ir (acac)] and methyl ethyl diketone root two (1,2-phenylbenzene-1H-benzo [d] imidazoles root) close iridium (III) and [be abbreviated as (pbi)
2Ir (acac)] organic electromechanical phosphorescent material that belongs to excellent performance [sees Lamansky S, Djurovich P, Murphy D, Razzaq F A, Kwong R, Tsyba I, Bortz M, Mui B, Bau R, ThompsonM E, Inorg.Chem.2001,40,1704. with Huanng W S, Lin J T, Chen C H, Tao Y T, Sun S S, Wen YS, Chem.Mater., 2004,16,2480].But, organic electrophosphorescenpolymer metal complexes class material normally is entrained in finite concentration and makes luminescent device in the material of main part, because luminescent device can produce Jiao Erre when work, make originally homodisperse small molecules luminescent material produce gathering, crystallization, cause the concentration quenching of phosphor material thereby producing is separated, cause light-emitting device life period and stability to reduce.
Summary of the invention
The object of the present invention is to provide the organic electrofluorescent iridium complex material of novel texture, this type of phosphor material not only can reduce the influence of concentration quenching to luminous efficiency, improves the stability and the life-span of electro phosphorescent device, and has shorter phosphorescent lifetime.
Technical scheme of the present invention is: be incorporated into existing complex of iridium organic electromechanical phosphorescent material (bt) having big sterically hindered radicals R
2Ir (acac) and (pbi)
2In the part of Ir (acac), reduce the intermolecular interaction of phosphor material by the spatial volume that increases the phosphorescent complexes molecule, thereby effectively stop the caused molecular aggregates when device heating of phosphor material molecule, the phosphorescence cancellation that reduction causes by being separated is to the influence of luminous efficiency.The structure of the novel organic electromechanical phosphorescent material that is synthesized is as follows:
In the said structure formula, R is the tertiary butyl or sec.-propyl, and X is sulphur atom or the nitrogen-atoms that is connected with phenyl substituent.
The assembly of R and X has four kinds of forms:
Or X is the S atom, and R is the tertiary butyl [C (CH
3)
3];
Or X is the S atom, and R is sec.-propyl [CH (CH
3)
2];
Or X is the N atom (ph-N) that is connected with phenyl substituent, and R is the tertiary butyl [C (CH
3)
3];
Or X is the N atom (ph-N) that is connected with phenyl substituent, and R is sec.-propyl [CH (CH
3)
2].
The organic electromechanical phosphorescent material of said structure, its preparation technology has two steps: first step is the preparation that has the part of big steric group; Second step is the preparation that part and trivalent iridium belong to ion and the formed metal complexes organic electromechanical phosphorescent material of methyl ethyl diketone.Above-mentioned technology is all carried out under normal pressure, and concrete operations and processing condition are illustrated by embodiment.
Complex of iridium class phosphor material of the present invention is mainly used in the making organic electro phosphorescent device, and its manufacture craft is that known, sophisticated technology [is seen Peng Q, Lu Z Y Lu, Huang Y, Xie M G et al, Macromolecules 2004,37,260-266], so be not described at this.
Organic electrofluorescent iridium complex material provided by the present invention has following beneficial effect:
1, owing to introduced steric group R, the spatial volume of the organic electrofluorescent iridium complex material that is provided increases, when being used to make the phosphorescence device, can effectively reduce intermolecular interaction, reduce molecule owing to being separated that thermal motion causes, thereby reduced the influence of concentration quenching luminous efficiency.
2, the embodiment of the invention 1 described methyl ethyl diketone root two [2-(to tert-butyl-phenyl) benzothiazole root] closes this title complex organic electrofluorescent material of iridium (III) (being called for short title complex 1) and the existing not similar phosphor material (bt) of carrying space steric group
2Ir (acac) compares, and the phosphorescence quantum yield is doubled approximately, and phosphorescent lifetime has reduced by one times approximately; The embodiment of the invention 3 described methyl ethyl diketone roots two [1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles root] close this title complex organic electrofluorescent material of iridium (III) (being called for short title complex 3) and the existing not similar phosphor material (pbi) of carrying space steric group
2Ir (acac) compares, and the phosphorescence quantum yield is basic identical, but phosphorescent lifetime reduced more than one times, and concrete data see Table 1:
Table 1 phosphorescence performance relatively
| The phosphor material kind | Phosphorescent emissions λ max(nm) | Phosphorescent lifetime τ (μ s) | Phosphorescence quantum yield Φ em |
| (bt) 2Ir(acac) | 566 | 1.8 | 0.26 |
| Title complex 1 | 564 | 1.1 | 0.51 |
| (pbi) 2Ir(acac) | 523 | 1.82 | 0.73 |
| Title complex 3 | 524 | 0.8 | 0.72 |
Annotate: above data all are 10
-5In the M dichloromethane solution, to record on similarity condition, the same instrument.Phosphorescent emissions spectrum records by JASCO FP-6200 spectrophotofluorometer; The phosphorescence quantum yield all is with Ir (ppy)
3Relative phosphorescence quantum yield for the standard substance gained; Phosphorescent lifetime is to record by the FLS920 spectrophotofluorometer (Edinburgh Instruments) that millisecond Xe photoflash lamp has been installed when 298K.
As can be seen from Table 1, with (bt)
2Ir (acac) and (pbi)
2Ir (acac) compares, and title complex 1 and title complex 3 be the better organic electromechanical phosphorescent material of performance beyond doubt.
3, the embodiment of the invention 1 described title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [2-(to tert-butyl-phenyl) benzothiazole root] is closed iridium (III) (be called for short title complex 1) and the embodiment of the invention 3 described title complex organic electromechanical phosphorescent material methyl ethyl diketone roots two [1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles root] to be closed iridium (III) (abbreviation title complex 3) and has made electroluminescent device as dopant material, the device architecture that is adopted is ITO/PEDOT:PSS (50nm)/PVK (40nm)/PFO+30wt%PBD: title complex (80nm) (different concns doping)/Ba (4nm)/Al (150nm) [wherein, PVK is poly-(N-vinylcarbazole), PFO is poly-(9, the 9-dioctyl fluorene), PBD is 2-(4-xenyl)-5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazole].Experiment shows: title complex 1 can obtain maximum luminous external quantum efficiency so that the doped in concentrations profiled of 4wt% is in polymeric matrix, reaches 8.71%; In addition, this device is at high current density (100mA/cm
2) drive condition under external quantum efficiency still up to 5.54%, luminous efficiency reaches 5.75cd/A, brightness is 6103cd/m
2Title complex 3 can obtain maximum luminous external quantum efficiency so that the doped in concentrations profiled of 1wt% is in polymeric matrix, reaches 10.25%; In addition, this device is at high current density (100mA/cm
2) drive condition under external quantum efficiency still up to 7.21%, luminous efficiency reaches 7.19cd/A, brightness is 7678cd/m
2Above-mentioned experimental data explanation, the electro phosphorescent device of made has high luminous external quantum efficiency and luminous efficiency, and still has good luminous efficiency under big drive-current condition, and obtained device has good stability.
Embodiment
Embodiment 1
Organic electromechanical phosphorescent material in the present embodiment is orange red phosphor material, by introduce the purpose that the tertiary butyl realizes increasing molecular volume in the contraposition of the 2-phenyl of 2-phenyl benzothiazole part.Its structural formula is as follows:
In the said structure formula, X is S, and R is C (CH
3)
3
Preparation technology is:
1,2-is to the preparation of tert-butyl-phenyl benzothiazole (abbreviation ligand 1)
At room temperature, N
2Protection down; in the 100ml three-necked bottle that tail gas absorption and prolong are housed, add 0.1mol near amino thiophenols and 60ml1-N-methyl-2-2-pyrrolidone N-; drip 0.1mol to the tert.-butylbenzene formyl chloride with constant pressure funnel then; after dropwising, be heated to 100 ℃ of reactions 1 hour, after solution colour becomes brown by yellow; be cooled to room temperature; solution is poured in the deionized water, is regulated pH value to 8～9 with 7N ammoniacal liquor, the gained solid after filtration, after the washing, drying crude product.Can obtain light blue needle-like solid behind the ethyl alcohol recrystallization, for 2-to the tert-butyl-phenyl benzothiazole.Productive rate: 78.7%; ESI-MS:268.1 (M+1);
1HNMR (CDCl
3), δ (ppm): 1.3-1.4 (9H, t-BuH), 7.36-7.40 (2H, ArH), 7.47-7.6 (2H, ArH), 7.89-7.91 (2H, ArH), 8.0-8.1 (2H, ArH).
2, title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [2-(to tert-butyl-phenyl) benzothiazole root] closes iridium (III) preparation of (being called for short title complex 1)
At room temperature in the 50ml three-necked bottle, add 1mmol IrCl
33H
2O, 2mmol part l and ethylene glycol ethyl ether: the mixing solutions 10ml of water=3: 1 (volume ratio).Nitrogen protection refluxed 48 hours down.After reaction stopped, suction filtration obtained the μ-chlorine bridging dimer of target title complex.μ-chlorine bridging dimer dissolved in behind the 60ml ethylene glycol ethyl ether add 1.0g Na to reaction system again
2CO
3With the 2ml methyl ethyl diketone, nitrogen protection refluxed 16 hours down.After reaction is finished, add the 200ml deionized water, suction filtration promptly obtains red title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [2-(to tert-butyl-phenyl) benzothiazole root] and closes iridium (III).Productive rate: 74%; ESI-MS:847.3 (M+23), 863 (M+39);
1HNMR (CDCl
3), δ (ppm): 0.6-1.0 (18H, t-BuH), 1.4-1.8 (6H, acacH), 5.0-5.4 (1H, acacH), 6.2-6.4 (2H, ArH), 6.8-7.0 (2H, ArH), 7.3-7.5 (4H, ArH), 7.5-7.6 (2H, ArH), 7.8-8.0 (2H, ArH), 8.1-8.2 (2H, ArH); Ultimate analysis [C
39H
39IrN
2O
2S
2]: calculated value %:C, 56.84; H, 4.77; N, 3.40; S, 7.78; Measured value: C, 56.76; H, 4.82; N, 3.36; S, 7.84.
Complex of iridium organic electromechanical phosphorescent material in the present embodiment can at room temperature send orange red phosphorescence.It is entrained in the device for preparing in the polymeric matrix can obtains the electroluminescent phosphorescence that emission wavelength is positioned at 564nm.When adopting following electroluminescent device structure: ITO/PEDOT:PSS (50nm)/PVK (40nm)/PFO+30wt%PBD: title complex 1 (4wt%) (80nm)/Ba (4nm)/Al (150nm), under direct voltage drive, can obtain 8.71% maximum luminous external quantum efficiency.In addition, this device is at high current density (100mA/cm
2) drive condition under luminous external quantum efficiency still up to 5.54%, luminous efficiency reaches 5.75cd/A, brightness is 6103cd/m
2
Embodiment 2
Organic electromechanical phosphorescent material in the present embodiment is orange red phosphor material, by introduce the purpose that sec.-propyl realizes increasing molecular volume in the contraposition of the 2-phenyl of 2-phenyl benzothiazole part.Its structural formula is as follows:
In the said structure formula, X is S, and R is CH (CH
3)
2
Preparation technology is:
1, the preparation of 2-p-isopropyl phenyl benzothiazole (being called for short part 2)
Technical process is with that related parameter is arranged is identical with embodiment 1, and raw material is substantially the same manner as Example 1, and difference from Example 1 is in the raw material tert.-butylbenzene formyl chloride to be become the cumic aldehyde formyl chloride.Employed cumic aldehyde formyl chloride is by cuminic acid and the backflow of excessive thionyl chloride are made.
2, title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [2-(p-isopropyl phenyl) benzothiazole root] closes iridium (III) preparation of (being called for short title complex 2)
Technical process is with that related parameter is arranged is identical with embodiment 1, and raw material is substantially the same manner as Example 1, and difference from Example 1 is that the ligand 1 in the raw material is become part 2.Productive rate: 78%; ESI-MS:833.3 (M+23);
1HNMR (CDCl
3), δ (ppm): 0.6-1.0 (12H, CH
3), 2.3 (2H, phCH), 1.4-1.8 (6H, acacH), 5.0-5.4 (1H, acacH), 6.2-6.4 (2H, ArH), 6.8-7.0 (2H, ArH), 7.3-7.5 (4H, ArH), 7.5-7.6 (2H, ArH), 7.8-8.0 (2H, ArH), 8.1-8.2 (2H, ArH); Ultimate analysis [C
38H
37IrN
2O
2S
2]: calculated value %:C, 56.30; H, 4.57; N, 3.46; S, 7.90; Measured value: C, 56.36; H, 4.56; N, 3.38; S, 7.84.
Complex of iridium organic electromechanical phosphorescent material in the present embodiment can send orange red phosphorescence.When adopting structure is ITO/PEDOT:PSS (50nm)/PVK (40nm)/PFO+30wt%PBD: title complex 2 (4wt%) (80nm)/under direct voltage drive, can obtain 6.21% maximum luminous external quantum efficiency during the electroluminescent device of Ba (4nm)/Al (150nm).
Embodiment 3
Organic electromechanical phosphorescent material in the present embodiment is the green phosphorescent material, by to 1, introduces the tertiary butyl in the contraposition of the 2-position phenyl of 2-phenylbenzene-1H-benzo [d] imidazole ligands and realizes increasing the purpose of molecular volume.Its structural formula is as follows:
In the said structure formula, X is ph-N, and R is C (CH
3)
3
Preparation technology is:
1, the preparation of 1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles (being called for short part 3)
At room temperature in the 250ml three-necked bottle, add adjacent nitro-N-phenylaniline 110mmol, zinc chloride 15mmol, benzene 100ml and to tert.-butylbenzene formyl chloride 100mol, reflux is 3 hours then.Reaction finishes, cool to room temperature, suction filtration.With the filtrate evaporate to dryness, promptly get resulting solid pure with ethyl alcohol recrystallization to the tertiary butyl-N-(2-nitrophenyl)-N-phenylbenzamaide.At room temperature in the 100ml three-necked bottle, add then the tertiary butyl-N-(2-nitrophenyl)-N-phenylbenzamaide 6mmol, iron powder 1g, acetic acid 20ml, stirring and refluxing 30 minutes.After reaction finishes, suction filtration.Filtrate is diluted with deionized water, uses saturated NaHCO
3Solution transfers to pH=7.Add CH
2Cl
2Extracted organic phase, anhydrous Na
2SO
4Dry.The yellow solid that obtains after the solvent evaporated is 1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles.Productive rate: 88%; ESI-MS:327.2 (M+1); 349.2 (M+23); 365.7 (M+39);
1HNMR (CDCl
3), δ (ppm): 1.02-1.50 (9H, t-BuH), 7.12-7.30 (2H, ArH), 7.30-7.40 (5H, ArH), 7.40-7.62 (5H, ArH), 7.8-8.0 (1H, ArH); IR:2959.0 (CH
3).
2, title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles root] closes iridium (III) preparation of (being called for short title complex 3)
At room temperature in the 50ml three-necked bottle, add 1mmol IrCl
33H
2O, 2mmol part 3 and ethylene glycol ethyl ether: the mixing solutions 10ml of water=3: 1 (volume ratio).Nitrogen protection refluxed 48 hours down.After reaction stopped, suction filtration obtained the μ-chlorine bridging dimer of target title complex.μ-chlorine bridging dimer dissolved in behind the 60ml ethylene glycol ethyl ether add Na to reaction system again
2CO
31.0g with methyl ethyl diketone 2ml, nitrogen protection refluxed 16 hours down.After reaction is finished, add 200ml water, suction filtration promptly gets green title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [1-phenyl-2-(to tert-butyl-phenyl)-1H-benzo [d] imidazoles root] and closes iridium (III).Productive rate: 98.1%; ESI-MS:965.3 (M+23), 981.2 (M+39);
1HNMR (CDCl
3), δ (ppm): 0.62-0.91 (18H, t-BuH), 1.51-1.94 (6H, acacH), and 5.08-5.44 (1H, acacH), 6.38-6.54 (5H, ArH), and 6.68-6.88 (2H, ArH), 7.08-7.15 (1H, ArH), and 7.24-7.35 (6H, ArH), 7.40-7.46 (1H, ArH), 7.52-7.72 (7H, ArH), and 7.74-7.88 (2H, ArH); Ultimate analysis [C
51H
49IrN
4O
2]: calculated value %:C, 65.01; H, 5.24; N, 5.95; Measured value: C, 64.89; H, 5.15; N, 6.04.
Complex of iridium organic electromechanical phosphorescent material in the present embodiment can send green glow.It is entrained in fabricate devices can obtain the electroluminescent phosphorescence that emission wavelength is positioned at 524nm in the polymeric matrix.When adopting following electroluminescent device structure: ITO/PEDOT:PSS (50nm)/PVK (40nm)/PFO+30wt%PBD: title complex 3 (1wt%) (80nm)/Ba (4nm)/Al (150nm), under direct voltage drive, can obtain 10.25% maximum luminous external quantum efficiency.In addition, this device is at high current density (100mA/cm
2) drive condition under luminous external quantum efficiency still up to 7.21%, luminous efficiency reaches 7.19cd/A, brightness is 7678cd/m
2
Embodiment 4:
Organic electromechanical phosphorescent material in the present embodiment is the green phosphorescent material, by to 1, introduces sec.-propyl in the contraposition of the 2-position phenyl of 2-phenylbenzene-1H-benzo [d] imidazole ligands and realizes increasing the purpose of molecular volume.Its structural formula is as follows:
In the said structure formula, X is ph-N, and R is CH (CH
3)
2
Preparation technology is:
1, the preparation of 1-phenyl-2-(p-isopropyl phenyl)-1H-benzo [d] imidazoles (being called for short part 4)
Technical process is with that related parameter is arranged is identical with embodiment 3, and raw material is substantially the same manner as Example 3, and difference from Example 3 is in the raw material tert.-butylbenzene formyl chloride to be become the cumic aldehyde formyl chloride.Employed cumic aldehyde formyl chloride is by cuminic acid and the backflow of excessive thionyl chloride are made.
2, title complex organic electromechanical phosphorescent material methyl ethyl diketone root two [1-phenyl-2-(p-isopropyl phenyl)-1H-benzo [d] imidazoles root] closes iridium (III) preparation of (being called for short title complex 4)
Technical process is with that related parameter is arranged is identical with embodiment 3, and raw material is substantially the same manner as Example 3, and difference from Example 3 is that the part in the raw material 3 is become part 4.Productive rate: 94.3%; ESI-MS:951.3 (M+23), 967.2 (M+39);
1HNMR (CDCl
3), δ (ppm): 0.60-0.91 (18H, t-BuH), 1.52-1.96 (6H, acacH), and 5.06-5.41 (1H, acacH), 6.33-6.51 (5H, ArH), and 6.60-6.80 (2H, ArH), 7.06-7.12 (1H, ArH), and 7.20-7.33 (6H, ArH), 7.38-7.44 (1H, ArH), 7.50-7.70 (7H, ArH), and 7.71-7.85 (2H, ArH); Ultimate analysis [C
50H
47IrN
4O
2]: calculated value %:C, 64.65; H, 5.06; N, 6.03; Measured value: C, 64.69; H, 5.02; N, 6.04.
Complex of iridium organic electromechanical phosphorescent material in the present embodiment can send green glow.It is entrained in fabricate devices can obtain the electroluminescent phosphorescence that emission wavelength is positioned at 524nm in the polymeric matrix.When adopting following electroluminescent device structure: ITO/PEDOT:PSS (50nm)/PVK (40nm)/PFO+30wt%PBD: title complex 4 (1wt%) (80nm)/Ba (4nm)/Al (150nm), under direct voltage drive, can obtain 8.36% maximum luminous external quantum efficiency.
Claims (3)
1, organic electrofluorescent iridium complex material is characterized in that the structural formula of this phosphor material is as follows:
In the said structure formula, R is the tertiary butyl or sec.-propyl, and X is a sulphur atom.
2, organic electrofluorescent iridium complex material according to claim 1 is characterized in that R is the tertiary butyl.
3, organic electrofluorescent iridium complex material according to claim 1 is characterized in that R is a sec.-propyl.
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| CN102146099B (en) * | 2010-02-09 | 2013-10-16 | 广东阿格蕾雅光电材料有限公司 | Synthesis method of organic-metallic iridium compound |
| CN102153593B (en) * | 2011-02-21 | 2013-04-03 | 四川大学 | Red light organic electroluminescent phosphorescent iridium compound |
| CN102659846B (en) * | 2012-03-30 | 2015-07-15 | 中国科学院宁波材料技术与工程研究所 | N-substituted phenylbenzimidazole trivalent-iridium organometallic complex and its preparation method and use |
| CN103965878A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Green-yellow light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device |
| CN103965876A (en) * | 2013-01-30 | 2014-08-06 | 海洋王照明科技股份有限公司 | Green-yellow light-emitting organic electroluminescent material, its preparation method and organic electroluminescent device |
| GB2533268A (en) * | 2014-12-02 | 2016-06-22 | Cambridge Display Tech Ltd | Organic light-emitting device |
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| Synthesis and Characterization of PhosphorescentCyclometalated Iridium Complexes. Sergey Lamansky et al.Inorg. Chem.,Vol.40 . 2001 |
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| 基于铱配合物材料的高效高稳定性有机发光二极管. 王军，魏孝强，饶海波，成建波，蒋亚东.物理学报，第56卷第2期. 2007 * |
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