CN103497219A - Red-light iridium complexes and application thereof in organic white or red electroluminescence device - Google Patents
Red-light iridium complexes and application thereof in organic white or red electroluminescence device Download PDFInfo
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Abstract
The invention discloses red-light iridium complexes and application thereof in an organic white or red electroluminescence device. Ligands are bidentate ligands formed by using C and N coordination sites and metal iridium; the complexes have a structural formula shown in the specification, wherein R1 is selected from hydrogen, fluorine, trifluoromethyl, cyan, C1-C20 alkyl or alkoxy, aryl or heteroaryl; R2 can be hydrogen or an aromatic structure unit; an iridium (III) complex is doped into a host material by using a spin coating method, so as to construct a white or red light device with a single light-emitting layer and further realize efficient emission. The iridium complexes are easy to synthesize and purify; and corresponding complexes keep high light emitting efficiency and can be used as alternative materials for preparing red light materials in the white light device.
Description
Technical field
The invention belongs to the organic electroluminescent field, be specifically related to based on applying in a class complexes of red light iridium and the white or red luminescent device of organic electroluminescence thereof.
Background technology
White light emitting diode (WOLEDs) is caused enough attention owing to having broad application prospects on flat pannel display and solid state lighting.Because the fluorescence and phosphorescence material may be used to prepare WOLEDs, up to the present variously for the method that improves device performance, be in the news out, in these methods, the WOLEDs of full phosphorescence doping is considered to effective means.
The transition metal atoms title complex is applied to can overcome in Organic Light Emitting Diode the efficiency upper limit of fluorescent device.Because the strong spin orbital coupling of transition metal title complex can produce singlet and triplet excitons makes internal quantum efficiency can reach 100% in theory simultaneously.Many transition metals, for example the title complex of iridium, ruthenium, osmium, palladium has been synthesized for the preparation of high-level efficiency phosphorescent OLED s(PHOLEDs).Change and can make glow color be regulated in wider scope by simple part, and can change chemical property.Yet, owing to having the coupling of outstanding spin metal and high radiative relaxation, the title complex that contains metal iridium remains the potential phosphorescence luminophore of tool.
Summary of the invention
The purpose of this invention is to provide a kind of luminous selection that depends on part of iridium metal complex, can be by selecting suitable part or taking the adjustment of part to obtain in high efficiency phosphorescent complexes one class complexes of red light iridium and the white or red luminescent device of organic electroluminescence thereof to part and apply.
The present invention designs and has synthesized a series of 2-naphthalene benzothiazoles n-heterocyclic ligands, with the coordination of transition metal iridium, forms title complex, and by the method for doping, that such is complex doped in material of main part, and structure individual layer ruddiness and white light parts are realized efficiently emission.
Synthetic iridium (III) title complex of the present invention has the hexa-coordinate structure, and structure is as follows:
Part adopts C, two haptos of N and metal iridium to form double coordination, and wherein the general formula of 2-naphthalene benzothiazoles bitooth ligand has following structure:
The concrete structure formula is:
Wherein, R
1be selected from hydrogen, fluorine, trifluoromethyl, cyano group, C
1-C
20alkyl or alkoxyl group, aryl, heteroaryl;
R
2be selected from a kind of in hydrogen or following aromatic structure unit:
Wherein, the R in described aromatic structure unit
3, R
4for C
1-C
20alkyl or alkoxyl group, aryl, heteroaryl.
All prepared by intramolecular cyclization reaction by all parts, this reacts with K
3fe (CN)
6with NaOH be catalyzer, take water as solvent, react 6h under 80-90 ℃.
All complex of iridium all make by two reactions.At first C
∧the N part reacts the dimer that generates chloride bridge with iridous chloride hydrate; Then, the chlorine bridge is replaced and generates complex of iridium by methyl ethyl diketone (acac).
For achieving the above object, in a preferred embodiment of the present invention, described compound is (CF
3bT-N)
2ir (acac):
(CF
3BT-N)
2Ir(acac)
another object of the present invention is a kind ofwhite or the red light-emitting device of organic electroluminescence, between the anode of the white or red light-emitting device of described organic electroluminescence and negative electrode, be provided with contain above-mentioned
complexes of red light iridiumemission layer and form supplementary layer by hole injection layer and electron injecting layer; Wherein, described emission layer consists of simple layer.
a kind ofthe application of organic electroluminescence white hair optical device specifically comprises the following steps:
Step 1: conducting polymer composite is spin-coated on to the ITO conductive glass surface cleaned, annealing makes it to form the hole transmission layer of 40-60nm;
Step 2: above-mentioned complexes of red light iridium is doped to according to a certain percentage in the mixing material of material of main part and electron transport material and is dissolved in organic solvent and forms solution, described solution is spun on described hole transmission layer as emission layer, and the spin coating rotating speed is 1000-4000r/min;
Step 3: and then direct electrode evaporation on described luminescent layer; Wherein, in described emission layer, various material mixture ratios are that in described emission layer, various material mixture ratios are material of main part: electron transport material: blue phosphorescent material: green phosphorescent material: complexes of red light iridium=100:40:10:0.3:Y, 0<Y≤3.
a kind ofthe application of the red luminescent device of organic electroluminescence specifically comprises the following steps:
Step 1: conducting polymer composite is spin-coated on to the ITO conductive glass surface cleaned, annealing makes it to form the hole transmission layer of 40-60nm;
Step 2: above-mentioned complexes of red light iridium is doped to according to a certain percentage in the mixing material of material of main part and electron transport material and is dissolved in organic solvent and forms solution, described solution is spun on described hole transmission layer as emission layer, and the spin coating rotating speed is 1000-4000r/min;
Step 3: and then direct electrode evaporation on described luminescent layer; Wherein, in described emission layer, various material mixture ratios are complexes of red light iridium=100:40:X, X=1-10
Organic solvent is selected from benzene, chlorobenzene or orthodichlorobenzene; Polymer as material of main part comprises: the derivative of polystyrene, polyhenylene, polyvinyl carbazole (PVK), polycarbazole, poly-fluorenes or poly-fluorenes, also can be selected from small molecule material comprises: 1,3-bis-(carbazole-9-yl) benzene (mCP), 4,4', 4'' – tri-(carbazole-9-yl) triphenylamine (TCTA), 4,4'-bis-(carbazole-9-yl) diphenyl (CBP) etc., preferably polyethylene carbazole (PVK).Electron transfer layer can be selected from following material: 2,2'-(1, the 3-phenyl) two [5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazoles] (OXD-7), 1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) benzene (TPBi), 3-(4-phenylbenzene)-5-(4-tert-butyl-phenyl)-4 (4-ethylphenyls)-1,2,4-triazole (TAZ) etc., preferably 2,2'-(1, the 3-phenyl) two [5-(4-tert-butyl-phenyl)-1,3,4-oxadiazoles] (OXD-7).Hole injection layer is selected from: PEDOT (poly-(3, the 4-Ethylenedioxy Thiophene)): the oxide compound of PSS (poly styrene sulfonate) or molybdenum, preferred PEDOT (poly-(3,4-Ethylenedioxy Thiophene)): PSS (poly styrene sulfonate).The green glow complex of iridium is selected from: three (2-phenylpyridines) close iridium (Ir (ppy)
3), acetopyruvic acid two (2-phenylpyridine) iridium (Ir (ppy)
2(acac)), preferred acetopyruvic acid two (2-phenylpyridine) iridium (Ir (ppy)
2(acac)).The blue light complex of iridium is selected from: two (4,6-difluorophenyl pyridine-N, C2) the pyridine formyl closes iridium (Firpic), two (2,4-difluorophenyl pyridine) four (1-pyrazolyl) boric acid iridium (III) (FIr6), preferred two (4,6-difluorophenyl pyridine-N, C2) the pyridine formyl closes iridium (Firpic).
The invention has the beneficial effects as follows: owing to adopting technique scheme, the compounds of this invention structure has the white light parts of individual layer luminescent layer, realizes efficiently emission.Such complex of iridium has the synthetic and characteristics of being easy to of purifying, and title complex has kept higher luminous efficiency accordingly, can be used as the candidate materials for preparing red light material in white light parts.
The accompanying drawing explanation
Fig. 1: provide title complex (N-CF
3bT)
2the UV, visible light of Ir (acac) in methylene dichloride and toluene absorbs (UV-vis) spectrum and fluorescent emission (PL) spectrum.
The electricity of the ruddiness organic electroluminescent LED of Fig. 2: embodiment 2 preparations causes emmission spectrum (EL).
Current density-the voltage of the ruddiness Organic Light Emitting Diode of Fig. 3: embodiment 2 preparations-brightness curve.
The luminous efficiency of the ruddiness Organic Light Emitting Diode of Fig. 4: embodiment 2 preparations is with the curve of current density change.
The electricity of white light organic electroluminescence diode under different voltage of Fig. 5: embodiment 3 preparations causes emmission spectrum (EL).
Current density-the voltage of the white organic LED of Fig. 6: embodiment 3 preparations-brightness curve.
The luminous efficiency of the white organic LED of Fig. 7: embodiment 3 preparations is with the curve of current density change.
Embodiment
Following examples are described the present invention in detail, but following examples do not limit the present invention.
Embodiment 1: title complex (N-CF
3bT)
2ir's (acac) is synthetic:
Under concrete synthesis step is shown in:
1: part CF
3bT-N's is synthetic
1 synthesize: by 4-5 amido benzotrifluoride (10.15g, 63mmol), 1-naphthoyl chloride (12.00g 63mol), triethylamine (9.6mL) is dissolved in the 100ml trichloromethane.Under 0 ℃, under argon shield, after reaction 30min, transfer under room temperature and continue reaction 6h, except desolventizing, use ethyl alcohol recrystallization, obtain white cotton-shaped solid 18.8g (95%).1H?NMR?(400?MHz,?CDCl3):?δ?(ppm)?9.13?(s,?1H),?8.38?–?8.22?(m,?1H),?7.92?(d,?J?=?8.2?Hz,?2H),?7.87?(d,?J?=?8.3?Hz,?1H),?7.85?–?7.77?(m,?1H),?7.74?(d,?J?=?7.0?Hz,?1H),?7.53?(d,?J?=?8.5?Hz,?2H),?7.51?–?7.45?(m,?2H),?7.42?(t,?J?=?7.7?Hz,?1H).?13C?NMR?(101?MHz,?CDCl3)?δ?168.02,?141.72,?133.77,?133.67,?131.05,?130.19,?128.39,?127.31,?126.53,?126.09,?126.05,?125.97,?125.28,?124.79,?122.87,?119.92.
2 synthesize: by 1(9.94g, 30mol), lawesson reagent (18.4g, 50mol) is dissolved in 60mL toluene, vacuumizes/lead to argon gas 3 times repeatedly, the lower reaction 20h that refluxes, except desolventizing, the product obtained obtains yellow solid 8.5g(86% with the column chromatography purification).1H?NMR?(400?MHz,?CDCl3):?δ?(ppm)?8.19?–?8.11?(m,?1H),?8.07?(d,?J?=?8.4?Hz,?2H),?7.89?(dd,?J?=?8.7,?5.4?Hz,?2H),?7.70?(d,?J?=?8.5?Hz,?2H),?7.65?(d,?J?=?6.4?Hz,?1H),?7.59?–?7.46?(m,?3H),?3.86?(d,?J?=?6.0?Hz,?1H).?13C?NMR?(101MHz,?CDCl3)?δ?199.82,?142.50,?141.50,?133.79,?130.12,?128.66,?128.63,?127.43,?126.61,?126.38,?126.35,?125.21,?124.95,?124.35,?122.50,?121.61.
3 synthesize: by product 2(3.3g, 10.2mmol) wetting with a small amount of ethanol, drip 30% NaOH solution (8eq), then be diluted with water to NaOH and become 10%.To in this suspension 5min, be added drop-wise to and contain 20%K
3fe (CN)
6(4eq) in solution (80-90 ℃), after reaction 6h, be cooled to room temperature, with HCl solution neutralization solution, then, with the CH2Cl2 extraction, solvent evaporated is purified and is obtained faint yellow solid 2.4g (72%) with column chromatography.
1H?NMR?(400?MHz,?CDCl
3):?δ?(ppm)?8.95?(d,?J?=?8.5?Hz,?1H),?8.26?(d,?J?=?7.7?Hz,?2H),?8.02?(d,?J?=?8.2?Hz,?1H),?7.98?–?7.90?(m,?2H),?7.78?(d,?J?=?8.4?Hz,?1H),?7.68?–?7.60?(m,?1H),?7.60?–?7.54?(m,?2H).?13C?NMR?(101?MHz,?CDCl3)?δ?170.88,?156.07,?135.46,?134.07,?131.79,?130.48,?130.18,?129.84,?128.56,?127.95,?127.63,?126.73,?125.69,?125.02,?123.88,?123.30,?123.27,?119.16.
2. title complex (CF
3bT-N)
2ir's (acac) is synthetic:
By product 3 (0.6586g, 2mmol), IrCl3 3H
2o (0.2820g, 0.8mmol), 2-ethoxyethanol: H
2o=15mL: 5mL joins in round-bottomed flask, vacuumize/applying argon gas three times repeatedly, back flow reaction 20h, be cooled to room temperature, add a large amount of water, the precipitation that filtration obtains with obtain the dipolymer powder of red chlorine bridging with ethanol, normal hexane washing, need not be purified respectively.By this product and methyl ethyl diketone (0.12g, 1.2mmol), Na2CO3 (0.424g, 4mmol) mixes, and then adds 10mL 2-ethoxyethanol, and 24h refluxes under argon shield.1H NMR (400 MHz, CDCl3): δ (ppm) 8.52 (d, J=8.4 Hz, 2H), 8.26 (s, 2H), 8.14 (d, J=8.7 Hz, 2H), 7.68 – 7.63 (m, 4H), 7.61 (d, J=7.3 Hz, 2H), 7.35 (t, J=7.4 Hz, 2H), 7.05 (d, J=8.5 Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 5.10 (s, 1H), 1.74 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 186.26, 180.36, 161.86, 151.56, 135.30, 133.82, 131.61, 131.47, 130.88, 130.52, 130.21, 127.90, 126.96, 126.63, 125.51, 124.60, 123.48, 121.39, 119.48, 101.58, 53.40, 28.28. MS (matrix-assisted laser desorption ionization time-of-ight (MALDI-TOF)): m/z:M+ C
41h
25f
6irN
2o
2s
2theoretical value: 948.0, measured value: 948.0.Ultimate analysis C
41h
25f
6irN
2o
2s
2theoretical value C 51.95, and H 2.66, and N 2.96; Measured value: C 51.76, H 2.83, and N 2.75.
embodiment 2: the preparation of ruddiness organic light-emitting device diode
The structure of device is: ITO/PEDOT:PSS (40nm)/PVK:OXD-7:(CF
3bT-N)
2ir (acac) (40nm)/Ca (10nm)/Al (100nm), the preparation technology of device is as follows:
On anode ITO with 3000r/min spin coating conducting polymer PEDOT:PSS, the 1h that anneals under 120 ℃, form the thick hole injection layer of 40nm;
2. by PVK:OXD-7: (CF
3p-N)
2ir (acac) is made into the solution of 15 mg/ml with 100:40:10, with the rotating speed of 2000 rev/mins, be spin-coated on PEDOT:PSS upper, in nitrogen, anneals 10 minutes for 120 ℃;
On luminescent layer evaporation Ca (10nm)/Al (100nm) as negative electrode.
The performance of gained ruddiness El element is as follows: open bright voltage: 10.4V, high-high brightness: 6930cd/m
2, top efficiency: 5.34 cd/A (19.8V), chromaticity coordinates (0.64,0.34).
embodiment 3: the preparation of the diode of the device of ruddiness organic light emission
The structure of device is: ITO/PEDOT:PSS (40nm)/PVK:OXD-7:(CF
3bT-N)
2ir (acac) (40nm)/Ca (10nm)/Al (100nm), the preparation technology of device is as follows:
On anode ITO with 3000r/min spin coating conducting polymer PEDOT:PSS, the 1h that anneals under 120 ℃, form the thick hole injection layer of 40nm;
2. by PVK:OXD-7: (CF
3p-N)
2ir (acac) is made into the solution of 15 mg/ml with 100:40:5, with the rotating speed of 2000 rev/mins, be spin-coated on PEDOT:PSS upper, in nitrogen, anneals 10 minutes for 120 ℃;
On luminescent layer evaporation Ca (10nm)/Al (100nm) as negative electrode.
The performance of gained ruddiness El element is as follows: open bright voltage: 10.4V, high-high brightness: 6930cd/m
2, top efficiency: 5.34 cd/A (19.8V), chromaticity coordinates (0.64,0.34).
embodiment 4: the preparation of the diode of white organic light emitting device
Use complexes of red light iridium (CF
3bT)
2ir (acac), blue phosphorescent emissive material Firpic and green phosphorescent emissive material Ir (ppy)
2(acac) be entrained in the mixing material of PVK and OXD-7 as emission layer.Device architecture is: ITO/PEDOT:PSS (40nm)/PVK:OXD-7:FIrpic:Ir (ppy)
2(acac): (CF
3bT-N)
2ir (acac) (40nm)/Ca (10nm)/Al (100nm), detailed preparation process is as follows:
1. take ITO as anode, hole injection layer PEDOT:PSS solution, with 3000 rev/mins, is spun to the ITO surface, anneal 1 hour under 120 ℃ in vacuum drying oven.
2. by PVK:OXD-7: Firpic:Ir (ppy)
2(acac): (CF
3p-CF
3bT)
2ir (acac) is dissolved in chlorobenzene according to the ratio of 100:40:10:0.3:1, makes its total concn reach 15 mg/ml, is spun to the surface of PEDOT:PSS with the rotating speeds of 2000 rev/mins, in nitrogen, anneals 10 minutes for 120 ℃;
On electron transfer layer evaporation Ca (10nm)/Al (100nm) as negative electrode.
The performance of the electroluminescent white light Organic Light Emitting Diode of gained is as follows: opening bright voltage is 8.2 V, and high-high brightness is: 27283cd/m
2, maximum luminous efficiency is 14.1cd/A (10.2V), under 12.5V, chromaticity coordinates is (0.35,0.36).
embodiment 5: the preparation of the diode of white organic light emitting device
Use complexes of red light iridium (CF
3bT)
2ir (acac), blue phosphorescent emissive material Firpic and green phosphorescent emissive material Ir (ppy)
2(acac) be entrained in the mixing material of PVK and OXD-7 as emission layer.Device architecture is: ITO/PEDOT:PSS (40nm)/PVK:OXD-7:FIrpic:Ir (ppy)
2(acac): (CF
3bT-N)
2ir (acac) (40nm)/Ca (10nm)/Al (100nm), detailed preparation process is as follows:
1. take ITO as anode, hole injection layer PEDOT:PSS solution, with 3000 rev/mins, is spun to the ITO surface, anneal 1 hour under 120 ℃ in vacuum drying oven.
2. by PVK:OXD-7: Firpic:Ir (ppy)
2(acac): (CF
3p-CF
3bT)
2ir (acac) is dissolved in chlorobenzene according to the ratio of 100:40:10:0.3:3, makes its total concn reach 15 mg/ml, is spun to the surface of PEDOT:PSS with the rotating speeds of 2000 rev/mins, in nitrogen, anneals 10 minutes for 120 ℃;
On electron transfer layer evaporation Ca (10nm)/Al (100nm) as negative electrode.
The above preparation to Ir provided by the invention (III) title complex and should be used as detailed introduction in ruddiness and white organic LED.Quoted specific case herein principle of the present invention and embodiment are set forth, but these examples are not limited to the present invention.Under the premise without departing from the principles of the invention any, the present invention is carried out to simple modification and also belong in the protection domain of claim of the present invention.
Claims (6)
1. a class complexes of red light iridium, this compound part adopts C, two haptos of N and metal iridium formation double coordination, it is characterized in that, and this compound has structural formula:
Wherein, R
1be selected from hydrogen, fluorine, trifluoromethyl, cyano group, C
1-C
20alkyl or alkoxyl group, aryl or heteroaryl; R
2be selected from a kind of in hydrogen or following aromatic structure unit:
Wherein, R
3, R
4for C
1-C
20alkyl or alkoxyl group, aryl, heteroaryl.
2. complexes of red light iridium as claimed in claim 1, is characterized in that, this compound has following structural formula:
3.
a kind ofwhite or the red light-emitting device of organic electroluminescence, is characterized in that, between the anode of the white or red light-emitting device of described organic electroluminescence and negative electrode, be provided with contain as claimed in claim 1 or 2
complexes of red light iridiumemission layer and form supplementary layer by hole injection layer and electron injecting layer; Wherein, described emission layer consists of simple layer.
4.
a kind ofthe application of organic electroluminescence white hair optical device, is characterized in that, specifically comprises the following steps:
Step 1: conducting polymer composite is spin-coated on to the ITO conductive glass surface cleaned, annealing makes it to form the hole transmission layer of 40-60nm;
Step 2: the described complexes of red light iridium of claim 1 or 2 is doped to according to a certain percentage in the mixing material of material of main part and electron transport material and is dissolved in organic solvent and forms solution, described solution is spun on described hole transmission layer as emission layer, and the spin coating rotating speed is 1000-4000r/min;
Step 3: and then direct electrode evaporation on described luminescent layer; Wherein, in described emission layer, various material mixture ratios are that in described emission layer, various material mixture ratios are material of main part: electron transport material: blue phosphorescent material: green phosphorescent material: complexes of red light iridium=100:40:10:0.3:Y, 0<Y≤3.
5.
a kind ofthe application of the red luminescent device of organic electroluminescence, is characterized in that, specifically comprises the following steps:
Step 1: conducting polymer composite is spin-coated on to the ITO conductive glass surface cleaned, annealing makes it to form the hole transmission layer of 40-60nm;
Step 2: the described complexes of red light iridium of claim 1 or 2 is doped to according to a certain percentage in the mixing material of material of main part and electron transport material and is dissolved in organic solvent and forms solution, described solution is spun on described hole transmission layer as emission layer, and the spin coating rotating speed is 1000-4000r/min;
Step 3: and then direct electrode evaporation on described luminescent layer; Wherein, in described emission layer, various material mixture ratios are complexes of red light iridium=100:40:X, X=1-10.
6. the application of the white or red luminescent device of organic electroluminescence as described as claim 4 or 5, it is characterized in that, described material of main part is selected from poly-fluorenes class and derivative thereof, polyvinyl carbazole and derivative thereof, mCP (1,3-bis-(carbazole-9-yl) benzene), TCTA (4,4', 4 " tri-(carbazole-9-yl) triphenylamine), any one in CBP (4; 4'-bis-(carbazole-9-yl) diphenyl), 26DczPPy (2,6-bis-(3-(9H-carbazole-9-yl) phenyl) pyridine);
Described electron transport material is selected from: OXD-7 (1,3-bis-[2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole-5-yl] benzene), TPBi (1,3,5-tri-(phenyl benzimidazolyl-) benzene), PBD (2-(4-xenyl)-5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazole), any one in TAZ (3-(4-xenyl)-4-phenyl-5-tert-butyl-phenyl l-1,2,4-triazole);
Described hole injection layer is selected from: a kind of in the oxide compound of PEDOT (poly-(3,4-Ethylenedioxy Thiophene)), PSS (poly styrene sulfonate) or molybdenum;
Described green phosphorescent material is selected from three (2-phenylpyridines) and closes iridium (Ir (ppy)
3), acetopyruvic acid two (2-phenylpyridine) iridium (Ir (ppy)
2(acac) a kind of); Described blue phosphorescent material thing is selected from two (4,6-difluorophenyl pyridine-N, C2) the pyridine formyl closes a kind of in (FIr6) of iridium (Firpic), two (2,4 difluorobenzene yl pyridines) four (1-pyrazolyl) boric acid iridium (III).
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105837641A (en) * | 2016-05-07 | 2016-08-10 | 吉林奥来德光电材料股份有限公司 | Synthesizing and application of novel iridium metal complex phosphorescent material |
| CN105859794A (en) * | 2016-05-07 | 2016-08-17 | 吉林奥来德光电材料股份有限公司 | Synthesis and application thereof of phosphor materials of novel iridium metal complex |
| CN110698921A (en) * | 2018-07-09 | 2020-01-17 | 中国科学院苏州纳米技术与纳米仿生研究所 | Ink for manufacturing organic light-emitting layer based on solution method and preparation method and application thereof |
| WO2020251031A1 (en) * | 2019-06-13 | 2020-12-17 | 三菱ケミカル株式会社 | Composition for organic electroluminescent elements, organic electroluminescent element, display device and lighting device |
| CN113185557A (en) * | 2021-05-12 | 2021-07-30 | 南京工业大学 | Iridium complex organic photovoltaic material and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050176624A1 (en) * | 2003-08-07 | 2005-08-11 | Thompson Mark E. | Organometallic complexes as singlet oxygen sensitizers |
| CN1803783A (en) * | 2005-12-16 | 2006-07-19 | 武汉大学 | Halogen atom-containing bidentate ligand, its iridium complex and electrogenerated phosphorescence device |
| CN101410477A (en) * | 2006-03-27 | 2009-04-15 | 昭和电工株式会社 | An organic light-emitting device using a compound having a carrier transport property and a phosphorescent property |
-
2013
- 2013-10-12 CN CN201310474147.XA patent/CN103497219A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050176624A1 (en) * | 2003-08-07 | 2005-08-11 | Thompson Mark E. | Organometallic complexes as singlet oxygen sensitizers |
| CN1803783A (en) * | 2005-12-16 | 2006-07-19 | 武汉大学 | Halogen atom-containing bidentate ligand, its iridium complex and electrogenerated phosphorescence device |
| CN101410477A (en) * | 2006-03-27 | 2009-04-15 | 昭和电工株式会社 | An organic light-emitting device using a compound having a carrier transport property and a phosphorescent property |
Non-Patent Citations (2)
| Title |
|---|
| FEI XU等，: "High color rendering white organic light-emitting diodes fabricated using a broad-bandwidth red phosphorescent emitter for lighting applications", 《SYNTHETIC METALS》, vol. 162, 3 January 2013 (2013-01-03) * |
| SERGEY LAMANSKY等，: "Highly Phosphorescent Bis-Cyclometalated Iridium Complexes:Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes", 《J. AM. CHEM. SOC.》, vol. 123, no. 18, 13 April 2001 (2001-04-13) * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837641A (en) * | 2016-05-07 | 2016-08-10 | 吉林奥来德光电材料股份有限公司 | Synthesizing and application of novel iridium metal complex phosphorescent material |
| CN105859794A (en) * | 2016-05-07 | 2016-08-17 | 吉林奥来德光电材料股份有限公司 | Synthesis and application thereof of phosphor materials of novel iridium metal complex |
| CN105859794B (en) * | 2016-05-07 | 2019-02-01 | 吉林奥来德光电材料股份有限公司 | A kind of synthesis and its application of novel iridium metal complex phosphor material |
| CN105837641B (en) * | 2016-05-07 | 2019-03-22 | 吉林奥来德光电材料股份有限公司 | A kind of synthesis and its application of novel iridium metal complex phosphor material |
| CN110698921A (en) * | 2018-07-09 | 2020-01-17 | 中国科学院苏州纳米技术与纳米仿生研究所 | Ink for manufacturing organic light-emitting layer based on solution method and preparation method and application thereof |
| CN110698921B (en) * | 2018-07-09 | 2022-10-25 | 中国科学院苏州纳米技术与纳米仿生研究所 | Ink for manufacturing organic light-emitting layer based on solution method and preparation method and application thereof |
| WO2020251031A1 (en) * | 2019-06-13 | 2020-12-17 | 三菱ケミカル株式会社 | Composition for organic electroluminescent elements, organic electroluminescent element, display device and lighting device |
| CN113185557A (en) * | 2021-05-12 | 2021-07-30 | 南京工业大学 | Iridium complex organic photovoltaic material and preparation method and application thereof |
| CN113185557B (en) * | 2021-05-12 | 2022-08-30 | 南京工业大学 | Iridium complex organic photovoltaic material and preparation method and application thereof |
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