CN106397494A - Iridium complex as well as preparation method and electroluminescence device with iridium complex - Google Patents
Iridium complex as well as preparation method and electroluminescence device with iridium complex Download PDFInfo
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- CN106397494A CN106397494A CN201610800807.2A CN201610800807A CN106397494A CN 106397494 A CN106397494 A CN 106397494A CN 201610800807 A CN201610800807 A CN 201610800807A CN 106397494 A CN106397494 A CN 106397494A
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- iridium
- pyrazine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
Abstract
The invention relates to an iridium complex which comprises novel main ligand and 2-(5-phenyl-1,3,4-thiadiazole-2-)phenol or 2-(5-(3-pyridine)yl-1,3,4-thiadiazole-2-)phenol as auxiliary ligand, wherein the main ligand of the series of the iridium complex is any one of 2,3-diphenyl quinoxaline, 2,3-diphenyl pyridine[2,3-b]pyrazine, 2,3-diphenyl pyrazine[2,3-b]pyrazine, dibenzo[a,c]phenazine and dipyridino[3,2-a:2',3'-c]phenazine derivatives. The iridium complex provided by the invention has the advantages of being high in light emission efficiency, stable in chemical property, easy to sublimate and purify, and the like, and is excellent in device property. By modifying the molecular structure of the ligand, the light emission intensity and the light emission efficiency of the ligand can be adjusted within an infrared wavelength range, and thus convenience can be brought to design and production of electroluminescence displays and illumination light sources.
Description
【Technical field】
The present invention relates to organic electroluminescence device technical field, more particularly, to one class complex of iridium and preparation method thereof and
Apply the luminescent device of described complex of iridium.
【Background technology】
Under the overall background that global energy requirements are growing and ecological environment causes anxiety, national governments greatly develop base in succession
In high-tech energy sustainability technology and industry.Organic electroluminescence device (OLEDs) is because its visual angle is wide, brightness is high, energy consumption
Low and many advantages, such as flexible device can be prepared, and receive much attention, it is referred to as to dominate the key technology in the following display world.Closely
Nian Lai, numerous studies show, in numerous heavy metal element coordination compounds, complex of iridium be considered as OLEDs phosphor material
Ideal chose.There is 5d76s2The iridium atom of outer electronic structure, after formation+trivalent cation, has 5d6Electron configuration, has
Stable hexa-coordinate octahedral structure, makes material have higher chemical stability and heat stability.Meanwhile, Ir (III) has
Larger spin orbit coupling constant (ξ=3909cm-1), be conducive to improving the interior quantum yield of coordination compound and reducing the luminous longevity
Life, thus improve the overall performance of luminescent device.
As phosphor material, complex of iridium typically has Microsecond grade, easily causes the triplet-triplet of complex of iridium
And the phosphorescence of triplet-intensify between son is quenched.In addition, in current conventional material, the hole of hole mobile material
Mobility is far above the electron mobility of electron transport material, and conventional material of main part is also based on hole transport, and this can lead
Cause the gathering in luminescent layer and electric transmission bed boundary for the hole of great quantities of spare.These factors all can lead to the reduction of efficiency and tight
The efficiency roll-off of weight.Research shows, if complex of iridium has higher electron transport ability, can effectively increase electronics and exist
The transmission of luminescent layer and distribution, the region widening electron-hole, the quantity in balance electronic-hole pair, greatly improve device
Efficiency, reduces roll-offing of efficiency.
Therefore, it is necessary to provide a kind of complex of iridium with high-luminous-efficiency and electron mobility.
【Content of the invention】
It is an object of the invention to provide a class contains new main part, with 2- (5- phenyl -1,3,4- thiadiazoles -2-)
Phenol or 2- (5- (3- pyridine) base -1,3,4- thiadiazoles -2-) phenol are complexes of red light iridium and its preparation side of assistant ligand
Method, such coordination compound can be applied in organic electroluminescence device as the centre of luminescence.
The present invention provides a kind of complex of iridium, and it contains four parts and an assistant ligand, and described main part is 2,3-
Diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c]
Azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] any one in phenazene derivative, described assistant ligand be 2- (5- phenyl -1,
3,4- thiadiazoles -2-) phenol or 2- (5- (3- pyridine) base -1,3,4- thiadiazoles -2-) phenol.
Preferably, described 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine
[2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] phenazene derivative is selected from：In containing substituent group any one.
Preferably, described 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrrole
Piperazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] phenazene derivative substituent group be fluorine or
Person's trifluoromethyl.
Preferably, described complex of iridium has that to number as follows be one of structure of RIr12-01 to RIr12-32：
A kind of preparation method of complex of iridium is provided in the present invention：By the iridium dimerization bridging coordination compound containing four main parts
With assistant ligand and sodium carbonate mixing, described main part is 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrrole
Piperazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] azophenlyene derive
Any one in thing；Add cellosolvo solution, carry out reacting by heating at 120-140 DEG C, response time 12-48h,
It is cooled to room temperature, vacuum distillation removes solvent, then with dichloromethane extraction, concentrate, through column chromatography for separation, obtain the thick of coordination compound
Product, obtain pure complex of iridium through distillation.
Preferably, the mol ratio of described iridium dimerization bridging coordination compound, assistant ligand and sodium carbonate is 1: 2: 5.
The present invention also provides a kind of electroluminescent device of this complex of iridium of application, and it includes substrate, anode, hole transport
Layer, organic luminous layer, electron transfer layer and negative electrode, described substrate is glass, and anode material is tin indium oxide (ITO)；Hole passes
Defeated layer uses 4,4 '-cyclohexyl two [N, N-- bis- (4- aminomethyl phenyl) aniline (TAPC), electron transport layer materials use 3,3 '-
(5 '-(3- (pyridin-3-yl) phenyl)-[1,1 '：3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines (TmPyPB), negative electrode employing
LiF/Al, organic luminous layer adopts the double emitting layers of doped structure, and described organic luminous layer includes material of main part and luminescent material,
Material of main part is to use 4,4 ', 4 respectively " double (3- (9- carbazyl) phenyl) pyrrole of-three (carbazole -9- base) triphenylamines (TcTa) and 2,6-
Pyridine (26DCzPPy), selected luminescent material is complex of iridium, mass fraction 5wt%.
Beneficial effects of the present invention：The complex of iridium that the present invention provides has luminous efficiency height, electron mobility is high and changes
Learn the features such as stable in properties, easy sublimation purification.The preparation method of described complex of iridium is simple, and yield is higher.Due to azacyclo-
Introduce, the electronic transmission performance of coordination compound can Effective Regulation, be the design of display of organic electroluminescence and lighting source
Production is provided convenience.
【Brief description】
Fig. 1 is used for the electroluminescent spectrum of organic electroluminescence device for the complex of iridium RIr12-01 that the present invention provides；
Fig. 2 is used for the brightness-voltage curve of organic electroluminescence device for the complex of iridium RIr12-01 that the present invention provides；
Fig. 3 is used for the current efficiency-brightness of organic electroluminescence device for the complex of iridium RIr12-01 that the present invention provides
Curve.
【Specific embodiment】
The present invention is described in further detail with reference to the accompanying drawings and examples.The term being used in the present invention, unless
It is otherwise noted, typically there is the implication of those of ordinary skill in the art's generally reason.
A kind of complex of iridium, it includes containing four main parts and an assistant ligand, and described main part is 2,3- hexichol
Base quinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene,
Two pyridos [3,2-a：2 ', 3 '-c] any one in phenazene derivative.Described 2,3- diphenylquinoxaline, 2,3- diphenyl
Pyridine [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ',
3 '-c] phenazene derivative is selected from： In containing substituent group appoint
Meaning is a kind of.Described assistant ligand is 2- (5- phenyl -1,3,4- thiadiazoles -2-) phenol or 2- (5- (3- pyridine) base -1,3,4- thiophenes
Diazole -2-) phenol.
The complex of iridium of the present invention all used in building-up process iridous chloride, ethylenediamine, 1,2-- diphenylamines derive
Thing, dibenzoyl derivant, phenanthrenequione and 1,10-Phenanthroline-5,6-Quinone etc., synthetic method is similar to.
By the iridium dimerization bridging coordination compound containing four main parts and assistant ligand and sodium carbonate mixing, described main part is
2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo
[a, c] azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] any one in phenazene derivative；Add cellosolvo solution,
Carry out reacting by heating, response time 12-48h at 120-140 DEG C, be cooled to room temperature, vacuum distillation removes solvent, then uses dichloro
Methane extracts, and concentrates, through column chromatography for separation, obtains the crude product of coordination compound, obtain complex of iridium through sublimation purification.Wherein, described
The mol ratio of iridium dimerization bridging coordination compound, assistant ligand and sodium carbonate is 1: 2: 5.
Described complex of iridium has that to number as follows be one of structure of RIr12-01 to RIr12-32：
Below with wherein one embodiment, numbering be RIr12-01 complex of iridium as a example illustrate present invention, lead to
Cross following embodiments to will be helpful to further understand the present invention, but do not limit present disclosure.
The synthetic method of coordination compound RIr12-01
Dibenzoyl (5.00mm0l) and 1,2- phenylenediamine (5.00mmol) are dissolved in 50mL ethanol and flow back at 80 DEG C
24 hours, column chromatographic isolation and purification obtained the main part 2 of white, 3- diphenylquinoxaline (4.43mmol, yield：88.6%).
Main part (13.08mmol) and iridous chloride (6.23mmol) are dissolved in 15mL cellosolvo, 130 DEG C of mixture is anti-
Answer 12h, be subsequently adding assistant ligand (12.46mmol) and sodium carbonate (31.15mmol), continue 130 DEG C of reaction 24h.System is cold
But, water and dichloromethane are added, organic layer concentrates column chromatography and obtains yellow solid RIr12-01, its yield is 45%.
Remaining method numbering the complex of iridium being RIr12-02～32 and structure and above-mentioned numbering are the iridium of RIr12-01
Coordination compound is similar, will not be described here.
The present invention with 2,3- diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,
3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] any one in phenazene derivative be as master
Part, design has synthesized a series of complexes of red light iridium.By designing part or complex structure, and by simple on part
Chemical substituents modification, reach regulation and control coordination compound light and electron mobility purpose.
Described azacyclo- is all the group having stronger electron-transporting, is conducive to injection and the transmission of equilbrium carrier.
Described complex of iridium has higher luminous efficiency and electron mobility, after optimized checking, its preparation method letter
Single, and yield is higher.
The preparation of organic electroluminescence device
Present invention also offers a kind of organic electroluminescence device, it comprises any of the above-described numbering is RIr12-01～32
Complex of iridium.
As a example below organic electroluminescence device being prepared as luminescent material using RIr12-01, organic electroluminescence of the present invention is described
The preparation of luminescent device.The structure of OLEDs device includes：Substrate, anode, hole transmission layer, organic luminous layer and electric transmission
Layer/negative electrode.
In the element manufacturing of the present invention, substrate is glass, and anode material is tin indium oxide (ITO)；Hole transmission layer uses
4, [N, N- bis- (4- aminomethyl phenyl) aniline (TAPC), electron transport layer materials use 3,3 '-(5 '-(3- (pyrrole to 4 '-cyclohexyl two
Pyridine -3- base) phenyl)-[1,1 ': 3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines (TmPyPB), thickness is 60nm, evaporation speed
Rate is 0.05nm/s；Negative electrode adopts LiF/A1.Organic luminous layer adopt doped structure double emitting layers, it include material of main part and
Luminescent material, material of main part is to use 4,4 ', 4 respectively "-three (carbazole -9- base) triphenylamines (TcTa) and double (3- (the 9- carbazole of 2,6-
Base) phenyl) pyridine (26DCzPPy), selected luminescent material is described complex of iridium RIr12-01, and mass fraction is preferred
5wt%.
Different materials structure in the present invention is as follows：
The present invention selects a kind of HONGGUANG coordination compound to prepare organic electroluminescence device.See also Fig. 1, Fig. 2 and Fig. 3,
Fig. 1 is used for the electroluminescent spectrum of organic electroluminescence device for the complex of iridium that the present invention provides, Fig. 2 and Fig. 3 is the present invention
The complex of iridium providing is used for the photoelectric properties of organic electroluminescence device.As shown in Figures 2 and 3, described organic electroluminescent
The startup voltage of device is 3.8V, and its maximum power efficiency and current efficiency are respectively 57.04cd/A, high-high brightness 64589cd/
m2.By studying photophysical property, show that this kind of phosphorescent iridium complex containing azacyclo- has higher device efficiency, aobvious
The field such as show and illuminate and there is actual application value.
Such phosphor material that the present invention provides can be applied to the emission layer of phosphorescent OLED s as the centre of luminescence, by setting
Meter part or complex structure, and by modifying to the chemical substituents of described part, invention achieves regulation and control cooperation
Thing glow color and the purpose of efficiency.
Above-described is only embodiments of the present invention, it should be noted here that for those of ordinary skill in the art
For, without departing from the concept of the premise of the invention, improvement can also be made, but these belong to the protection model of the present invention
Enclose.
Claims (7)
1. it is characterised in that it includes four main parts and an assistant ligand, described main part is 2,3- to a kind of complex of iridium
Diphenylquinoxaline, 2,3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c]
Azophenlyene, two pyridos [3,2-a：2 ', 3 '-c] any one in phenazene derivative, described assistant ligand be 2- (5- phenyl -1,
3,4- thiadiazoles -2-) phenol or 2- (5- (3- pyridine) base -1,3,4- thiadiazoles -2-) phenol.
2. complex of iridium according to claim 1 is it is characterised in that described 2,3- diphenylquinoxaline, 2,3- diphenyl
Pyridine [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ',
3 '-c] phenazene derivative is selected from： In containing substituent group appoint
Meaning is a kind of.
3. complex of iridium according to claim 1 is it is characterised in that described 2,3- diphenylquinoxaline, 2,3- diphenyl
Pyridine [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,2-a：2 ',
3 '-c] phenazene derivative substituent group be fluorine or trifluoromethyl.
4. complex of iridium according to claim 1 is it is characterised in that described complex of iridium has one of following structure：
5. a kind of preparation method of the complex of iridium as described in any one as claim 1-4 is it is characterised in that will be containing four masters
The iridium dimerization bridging coordination compound of part and assistant ligand and sodium carbonate mixing, described main part is 2,3- diphenylquinoxaline, 2,
3- hexichol yl pyridines [2,3-b] pyrazine, 2,3- diphenyl pyrazine [2,3-b] pyrazine, dibenzo [a, c] azophenlyene, two pyridos [3,
2-a：2 ', 3 '-c] any one in phenazene derivative；Add cellosolvo solution, heated at 120-140 DEG C
Reaction, response time 12-48h, it is cooled to room temperature, vacuum distillation removes solvent, then with dichloromethane extraction, concentrate, through post layer
Analysis separates, and obtains the crude product of coordination compound, obtains pure complex of iridium through distillation.
6. complex of iridium according to claim 5 preparation method it is characterised in that described iridium dimerization bridging coordination compound and
The mol ratio of sodium carbonate is 1: 5.
7. a kind of electroluminescent device of application complex of iridium as described in claim 1-3 any one, it includes substrate, sun
Pole, hole transmission layer, organic luminous layer, electron transfer layer and negative electrode, described substrate is glass, and anode material is tin indium oxide；
Hole transmission layer uses 4,4 '-cyclohexyl two [N, N- bis- (4- aminomethyl phenyl) aniline, electron transport layer materials use 3,3 '-
(5 '-(3- (pyridin-3-yl) phenyl)-[1,1 '：3 ', 1 "-triphenyl] -3,3 "-diyl) two pyridines, negative electrode adopts LiF/Al,
Organic luminous layer adopts the double emitting layers of doped structure, and described organic luminous layer includes material of main part and luminescent material, main body material
Material is to use 4,4 ', 4 respectively "-three (carbazole -9- base) triphenylamines and double (3- (9- carbazyl) phenyl) pyridine of 2,6-, selected
Luminescent material is complex of iridium, mass fraction 5wt%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134550A (en) * | 2018-10-23 | 2019-01-04 | 常州大学 | D-A-D type ring metal iridium complex near-infrared light-emitting material and application based on aryl and quinoxaline |
| WO2020136496A1 (en) * | 2018-12-28 | 2020-07-02 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting device, light-emitting apparatus, electronic instrument, and illumination apparatus |
| US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1890255A (en) * | 2003-12-02 | 2007-01-03 | 株式会社半导体能源研究所 | Organic metal complex and light-emitting device using same |
-
2016
- 2016-09-02 CN CN201610800807.2A patent/CN106397494A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1890255A (en) * | 2003-12-02 | 2007-01-03 | 株式会社半导体能源研究所 | Organic metal complex and light-emitting device using same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11390639B2 (en) | 2018-04-13 | 2022-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN109134550A (en) * | 2018-10-23 | 2019-01-04 | 常州大学 | D-A-D type ring metal iridium complex near-infrared light-emitting material and application based on aryl and quinoxaline |
| WO2020136496A1 (en) * | 2018-12-28 | 2020-07-02 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting device, light-emitting apparatus, electronic instrument, and illumination apparatus |
| US11820783B2 (en) | 2019-09-06 | 2023-11-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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Application publication date: 20170215 |