CN108586543A - A kind of blue light ionic type iridium complex and the preparation method and application thereof - Google Patents
A kind of blue light ionic type iridium complex and the preparation method and application thereof Download PDFInfo
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Abstract
The present invention relates to a kind of blue light ionic type iridium complex and the preparation method and application thereof, which is coordinated using complex of iridium as the centre of luminescence by main ligand and assistant ligand.The complex is formed using iridium as the centre of luminescence with main ligand and assistant ligand, has general structure as shown in Equation 1：Wherein, the structure of D is as shown in Equation 2；Assistant ligand N^N can be independently one kind in tetrabutyl ammonium cyanide, pyridine, 2,2' bipyridyls, 1,10 ferrosins；Wherein, 1≤n≤20, and n is natural number；* it is link position.Material preparation of the present invention is simple, and reaction process is easy to control, and product is easily purified separation, and yield and purity are higher.Such material dissolubility is good, can be used for solwution method and prepares efficient Organic Light Emitting Diode and organic light emission electrochemical cell device, the device of gained shows good thermal stability, film forming stability, had potential application in terms of organic luminescent device.
Description
Technical field
The invention belongs to field of photovoltaic materials, and in particular to a kind of electroluminescent organic material relates more specifically to a kind of indigo plant
Photoion type complex of iridium and the preparation method and application thereof.
Background technology
The internal quantum efficiency (IQE) of phosphor material theoretically can be with 100%, this greatly enhances device efficiency,
Application prospect is very wide.Complex of iridium in phosphor material is because luminescent color is adjustable, luminous quantum efficiency is high, thermal stability
The high and short advantage of luminescent lifetime, is widely applied to phosphorescent organic electroluminescent diode component (OLED).At present efficiently
Rate phosphor material is mostly complex of iridium small molecule, and the method for the method generally use vacuum evaporation of preparation can cause material in this way
The serious waste of material.Small molecule complex of iridium is not suitable for solwution method and prepares OLED.Obtain high efficiency red, green, blue three primary colours device
It is the basis for realizing high quality full-color display and white-light illuminating.The blue light emitting material of efficient stable is the hot spot and difficulty of research
The blue light complex of iridium of point, especially solution processable.
Invention content
The purpose of the present invention is to provide a kind of blue light ionic type iridium complexes and the preparation method and application thereof, improve blue light
Dissolubility, film forming, thermal stability of complex of iridium etc., to realize that solwution method prepares blue-light device.
To achieve the above object, the technical solution adopted in the present invention is：
A kind of blue light ionic type iridium complex, the complex is using iridium as the centre of luminescence, with main ligand and assistant ligand
It forms, there is general structure as shown in Equation 1：
Wherein, the structure of D is as shown in Equation 2；Assistant ligand N^N can be independently tetrabutyl ammonium cyanide, pyridine, 2,2'- connection
One kind in pyridine, 1,10- ferrosins；
Wherein, 1≤n≤20, and n is natural number；* it is link position.
The complex is one kind in formula 3, formula 4, structure shown in formula 5 or formula 6：
Wherein, 1≤n≤20, and n is natural number.
A kind of preparation method of blue light ionic type iridium complex, includes the following steps：
Step 1, the synthesis of dimer：Under the conditions of inert nitrogen gas, in cellosolvo dicyandiamide solution, by difluoro
Dipyridyl derivatives are reacted with more hydrated iridium trichlorides at 110~140 DEG C, obtain iridium (III) chlorine bridge dimer；
Step 2, the synthesis of complex of iridium：It, will in the presence of Anhydrous potassium carbonate in the dicyandiamide solution of dichloromethane and methanol
Iridium (III) chlorine bridge dimer is reacted with assistant ligand at 30~60 DEG C, obtains blue light iridium (III) complex.
In the step 1, the molar ratio of difluoro dipyridyl derivatives and more hydrated iridium trichlorides is 2.2:1.
In the step 2, the molar ratio of iridium (III) chlorine bridge dimer and assistant ligand is 1:1.5~10.
The assistant ligand is one kind in tetrabutyl ammonium cyanide, pyridine, 2,2'- bipyridyls or 1,10- ferrosins.
The synthetic route of the step 1 and the specific steps are：
Step 11, compound 1, the borate of D, four triphenyl phosphorus palladiums are added in the reaction vessel being protected from light, substitute nitrogen
Tetrabutylammonium bromide, toluene, K are added after gas2CO3Solution reacts 24~48h at 85~100 DEG C, is cooled to after reaction
Room temperature is extracted and is concentrated through water and dichloromethane solution, and compound 2 is obtained by chromatography；
Step 12, by compound 2 and 2,6- difluoro pyridine -3- boric acid, four triphenyl phosphorus palladiums are put into and are protected from light in container,
Ethyl alcohol, toluene, K is added after substituting nitrogen2CO3Solution reacts 24~48h at 85~100 DEG C, is cooled to room after reaction
Wen Jingshui and dichloromethane solution are extracted and are concentrated, and compound 3 is obtained by chromatography；
Step 13, compound 3 and more hydrated iridium trichlorides are put into reaction vessel, 2- ethyoxyls is added after substituting nitrogen
Second alcohol and water reacts 24~48h at 110~140 DEG C, is cooled to room temperature after reaction, then through suction filtration and chromatography
Obtain dimer 4.
The synthetic route of the step 2 and the specific steps are：
Compound 4, assistant ligand and potassium carbonate powder are put into the reaction vessel being protected from light, dichloro is added after substituting nitrogen
Methane and methanol, at 30~60 DEG C react 12~for 24 hours, when reaction terminate be cooled to room temperature, then through extract and chromatography
Obtain the blue light ionic type iridium complex.
The blue light ionic type iridium complex of the present invention can be used as luminescent material in organic electroluminescence device, organic light emission
Application in electrochemical cell device.
When carrying out above application, following technical scheme specifically may be used：
A kind of organic electroluminescence device, including first electrode, second electrode, and first electrode and second electrode it
Between one or more layers organic function layer for being formed, it is characterised in that：Include at least one layer of organic function layer claim 1 or
Blue light ionic type iridium complex described in 2.
Advantageous effect:The blue light ionic type iridium complex of the present invention has the advantage of following several respects：1) in main ligand
Include a dimethyl benzene oxyalkyl chain in structure, can effectively limit conjugation so that the luminous of complex of iridium does not occur
Apparent red shift keeps effectively enhancing solubility property and filming performance while its blue emission characteristic；2) dimethyl benzene between introducing
Oxyalkyl chain not only increases material dissolubility, and has efficiently controlled intermolecular interaction, to inhibit triplet state-
Triplet state is buried in oblivion, and the luminous efficiency of material is improved, and obtains the device performance of enhancing；3) by with tetrabutyl ammonium cyanide, pyridine,
The assistant ligand that the strong electron-withdrawing groups such as bipyridyl group is used as, is conducive to the blue shift of spectrum, the blue light ionic cooperation being prepared
Object can promote carrier transport；4) blue light material provided by the invention is prepared simple, and reaction process is easy to control, and product holds
It is easily purified separation, and yield and purity are higher；5) such material dissolubility is good, can be used for solwution method prepare Nan dian Yao device and
Organic light emission electrochemical cell device.
Description of the drawings
Fig. 1 is D1Ir-CN's1H NMR spectras；
Fig. 2 is D1Ir-Py's1H NMR spectras；
Fig. 3 is D1Ir-BP's1H NMR spectras；
Fig. 4 is D1Ir-PM's1H NMR spectras；
Fig. 5 is the absorption spectrum of D1Ir-CN, D1Ir-Py, D1Ir-BP and D1Ir-PM in methylene chloride；
Fig. 6 is the emission spectrum of D1Ir-CN, D1Ir-Py, D1Ir-BP and D1Ir-PM in methylene chloride；
Fig. 7 is the thermogravimetric curve of D1Ir-CN, D1Ir-Py, D1Ir-BP and D1Ir-PM；
Fig. 8 is D1Ir-Py external quantum efficiencys-voltage curve；
Fig. 9 is the electroluminescent spectrum of D1Ir-Py.
Specific implementation mode
The blue light ionic type iridium complex of invention is coordinated using iridium as the centre of luminescence by main ligand and assistant ligand, by
Based on modified 2', bis- fluoro- 2,3'- bipyridyls (difluoro bipyridyl) of 6'- are main ligand, with tetrabutyl ammonium cyanide, pyridine, 2,
One kind in 2'- bipyridyls or 1,10- ferrosins is that auxiliary ligands are formed.With general structure as shown in Equation 1：
Wherein, the structure of D is as shown in Equation 2；Assistant ligand N^N can be independently tetrabutyl ammonium cyanide, pyridine, 2,2'- connection
One kind in pyridine, 1,10- ferrosins；O is oxygen atom；N is nitrogen-atoms；F is fluorine atom；
Wherein, 1≤n≤20, and n is natural number；* it is link position.
The blue light ionic type iridium complex can be one kind in formula 3, formula 4, structure shown in formula 5 or formula 6：
Wherein, 1≤n≤20, and n is natural number.
The preparation method of the blue light ionic type iridium complex of the present invention, includes the following steps：
Step 1, under the conditions of inert nitrogen gas, in cellosolvo dicyandiamide solution, by difluoro dipyridyl derivatives
With more hydrated iridium trichlorides in molar ratio 2.2:1 reacts at 110~140 DEG C, obtains iridium (III) chlorine bridge dimer；
Step 2, in the dicyandiamide solution of dichloromethane and methanol, in the presence of Anhydrous potassium carbonate, by iridium (III) chlorine bridge dimerization
A kind of in molar ratio 1 in body and tetrabutyl ammonium cyanide, pyridine, 2,2'- bipyridyls or 1,10- ferrosins:1.5~10 30~
It is reacted at 60 DEG C, obtains blue light iridium (III) complex.
Specifically, synthetic route and synthesis step are：
Step 11, compound 1, the borate of D, four triphenyl phosphorus palladiums are added in the reaction bulb being protected from light, substitute nitrogen
Tetrabutylammonium bromide, toluene, K are added afterwards2CO3Solution (2mol/L~4mol/L) reacts 24~48h, instead at 85~100 DEG C
It is cooled to room temperature after answering and extracts and concentrate through water and dichloromethane solution, compound 2 is obtained by chromatography.
Step 12：By compound 2 and 2,6- difluoro pyridine -3- boric acid, four triphenyl phosphorus palladiums are put into and are protected from light in bottle, take out
Ethyl alcohol, toluene, K is added after changing nitrogen2CO3Solution (2mol/L~4mol/L) reacts 24~48h, reaction at 85~100 DEG C
After be cooled to room temperature and extract and concentrate through water and dichloromethane solution, compound 3 is obtained by chromatography.
Step 13：Compound 3 and more hydrated iridium trichlorides are put into reaction bulb, 2- ethyoxyl second is added after substituting nitrogen
Alcohol and water reacts 24~48h at 110~140 DEG C, is cooled to room temperature after reaction, then is obtained with chromatography through filtering
To dimer 4.
Step 2：Dimer 4, tetrabutyl ammonium cyanide and potassium carbonate powder are put into the reaction tube being protected from light, after substituting nitrogen
Dichloromethane and methanol is added, reacts 12 at 30~60 DEG C~for 24 hours, terminates to be cooled to room temperature when reaction, then through extracting and color
Spectrum column purification obtains DIr-CN.Similar, same operating procedure, with one in pyridine, 2,2'- bipyridyls, 1,10- ferrosins
Kind is assistant ligand, can respectively obtain DIr-Py, DIr-BP and DIr-PM.
Wherein, K2CO3A concentration of 2mol/L~4mol/L of solution.
Below by way of several embodiments, the invention will be further described, but embodiment do not limit the present invention cover model
It encloses.
Embodiment 1：
The synthesis of dimer 4：
Specific steps are implemented as follows：
Step 1：By 4- (2- ethyl hexyl oxies) -2,6- dimethylphenyl boronic acids ester (7.2g, 19.98mmol), the chloro- 4- bromines of 2-
Pyridine (3.85g, 20.01mmol), four triphenyl phosphorus palladiums (0.693g, 0.61mmol) and TBAB (0.64g, 20mmol) are put into
In 250mL reaction bulbs, the K that 60mL toluene and a concentration of 2mol/L of 30mL are sequentially added after nitrogen is substituted2CO2250mL reactions are added
It in bottle, is reacted at 85 DEG C for 24 hours, waits for that concentrated after reaction and chromatography obtains weak yellow liquid (4.75g, 68.7%),
As compound 2.
Step 2：Will by step 1 gained compound 2 (3.5g, 10.12mmol), 2,6- difluoro pyridine -3- boric acid (1.93g,
12.14mmol), four triphenyl phosphorus palladiums (0.346g, 0.3mmol) are put into 250mL reaction bulbs, are sequentially added after substituting nitrogen
The K of a concentration of 4mol/L of 30mL toluene, 10mL2CO2It with 10mL ethyl alcohol in 250mL reaction bulbs, is reacted at 85 DEG C for 24 hours, waits reacting
After concentrated and chromatography obtain weak yellow liquid (2.3g, 54.1%), as compound 3.
Step 3：By step 2 gained compound 3 (2.1g, 4.94mmol), more hydrated iridium trichlorides (0.67g,
It 2.25mmol) is sequentially placed into 100mL reaction bulbs, 15mL ethylene glycol ethyl ethers and 5mL H is sequentially added after substituting nitrogen 3 times2O in
In 100mL reaction bulbs, is reacted at 110 DEG C and wait for removing high boiling solvent using the method for vacuum distillation after reaction for 24 hours, added
The methanol for entering 100mL has faint yellow solid (2.3g, 54.1%), as dimer 4.
The synthesis of D1Ir-CN：
Reaction condition：Dimer 4 (100mg, 0.048mmol) and tetrabutyl ammonium cyanide (63.47mg, 0.24mmol) are put
In 50mL reaction tubes, after substituting nitrogen, reaction tube is added in 10mL dichloromethane and 5mL methanol, reacts 12h at room temperature, waited for anti-
Concentrated and chromatography obtains D1Ir-CN (52mg, 50.6%) after answering.
D1Ir-CN:1H NMR(400MHz,CDCl3,δ):9.76 (d, J=6.0Hz, 2H), 8.06 (s, 1H), 7.05 (d, J
=5.6Hz, 1H), 6.77 (s, 2H), 5.74 (s, 1H), 3.91 (d, J=5.3Hz, 2H), 3.45-3.33 (m, 4H), 2.17 (s,
6H), 1.28 (s, 5H), 0.96 (d, J=7.6Hz, 6H)
Embodiment 2：
The synthesis step of dimer 4 is the same as embodiment 1；
The synthesis of D1Ir-Py：
Specific steps are implemented as follows：
Reaction condition：Dimer 4 (100mg, 0.048mmol) and pyridine (37.66mg, 0.48mmol) are put into 50mL reactions
10mL dichloromethane and 5mL methanol after substituting nitrogen, are added reaction tube, react 12h at room temperature, wait for after reaction by Guan Zhong
Concentrated and chromatography obtains D1Ir-Py (43mg, 45.5%).D1Ir-Py:1H NMR(400MHz,CDCl3,δ):8.48
(d, J=5.7Hz, 2H), 8.09 (s, 1H), 7.16 (dd, J=5.9,1.7Hz, 1H), 6.76 (d, J=3.3Hz, 2H), 5.68
(s, 1H), 3.90 (d, J=5.1Hz, 2H), 2.17 (d, J=15.4Hz, 6H), 1.91 (s, 3H), 1.75 (dd, J=11.8,
5.8Hz, 1H), 1.54-1.42 (m, 4H), 1.40-1.31 (m, 5H), 0.94 (dd, J=13.0,7.3Hz, 6H)
Embodiment 3：
The synthesis of D1Ir-BP：
Specific steps are implemented as follows：
Reaction condition：By dimer 4 (100mg, 0.048mmol) and 2,2- bipyridyls (37.49mg, 0.24mmol) are put
In 50mL reaction tubes, after substituting nitrogen, reaction tube is added in 10mL dichloromethane and 5mL methanol, reacts 12h at room temperature, waited for anti-
Concentrated and chromatography obtains D1Ir-BP (47mg, 48.3%) after answering.
D1Ir-BP:1H NMR(400MHz,CDCl3,δ):9.78 (d, J=7.5Hz, 2H), 8.48 (t, J=7.3Hz,
2H), 8.16 (s, 2H), 8.03 (d, J=5.2Hz, 2H), 7.68-7.58 (m, 4H), 7.07 (d, J=5.7Hz, 2H), 6.72
(s, 5H), 5.70 (s, 2H), 3.87 (d, J=5.5Hz, 2H), 2.10 (t, J=39.7Hz, 9H), 1.36-1.32 (m, 4H),
1.27 (s, 1H), 0.94 (dd, J=13.1,5.6Hz, 6H)
Embodiment 4：
The synthesis of D1Ir-PM：
Specific steps are implemented as follows：
Reaction condition：By dimer 4 (100mg, 0.048mmol) and 1,10- ferrosins (47.57mg, 0.24mmol) are put
In 50mL reaction tubes, after substituting nitrogen, reaction tube is added in 10mL dichloromethane and 5mL methanol, reacts 12h at room temperature, waited for anti-
Concentrated and chromatography obtains D1Ir-PM (46mg, 47.2%) after answering.
D1Ir-PM:1H NMR(400MHz,CDCl3,δ):8.32 (d, J=5.9Hz, 2H), 8.06 (s, 2H), 7.08 (dd,
J=5.8,1.7Hz, 2H), 6.75 (d, J=13.9Hz, 4H), 5.88 (s, 2H), 5.62 (s, 1H), 3.89 (d, J=5.7Hz,
2H), 2.21 (s, 3H), 2.03 (s, 3H), 1.39-1.32 (m, 6H), 1.25 (s, 6H), 0.94 (d, J=10.8Hz, 15H)
Embodiment 5：
It is entrained in 4,4', 4 "-three (carbazole -9- bases) triphenylamines (TCTA) and 2,6- using 2 complex D1Ir-Py of embodiment
Organic electroluminescence is manufactured in bis- ((9H- carbazole -9- bases) -3,1- phenylenes) pyridine (26DCzPPy) hybrid agent materials
Part.First, in the conducting polymer (PEDOT of the glass surface spin coating 40nm coated with tin indium oxide:PSS) hole is used as to inject
Layer；Then, on hole injection layer spin coating doping D1Ir-Py 4,4', 4 "-three (carbazole -9- bases) triphenylamines (TCTA) and 2,
Bis- ((9H- carbazole -9- bases) -3,1- phenylenes) pyridine (26DCzPPy) hybrid agents of 6- form the luminescent layer of 40nm；Then, according to
Electron transfer layer 1,3,5- tri- [(3- pyridyl groups) -3- phenyl] benzene, the boundary layer LiF and 100nm of 0.8nm of secondary deposition 60nm is cloudy
Pole aluminium.Bis- ((9H- carbazole -9- the bases) -3,1- phenylenes) pyridines of 2,6-
External quantum efficiency-voltage curve of device is as shown in figure 8, when complex D1Ir-Py doping concentrations are 12%, device
Part can reach better performance, and maximum external quantum efficiency is 2.35%.Test device electroluminescent spectrum as shown in figure 9,
Emission peak is located at 458nm and 480nm, chromaticity coordinates CIE value X=0.18, Y=0.27.
Claims (10)
1. a kind of blue light ionic type iridium complex, which is characterized in that the complex is using iridium as the centre of luminescence, by main ligand and auxiliary
Ligand coordinates, and has general structure as shown in Equation 1：
Wherein, the structure of D is as shown in Equation 2；Assistant ligand N^N can be independently tetrabutyl ammonium cyanide, pyridine, 2,2'- bipyridyls,
One kind in 1,10- ferrosins；
Wherein, 1≤n≤20, and n is natural number；* it is link position.
2. blue light ionic type iridium complex according to claim 1, it is characterized in that being, which is formula 3, formula 4, formula
5 or formula 6 shown in one kind in structure：
Wherein, 1≤n≤20, and n is natural number.
3. a kind of preparation method of blue light ionic type iridium complex described in claim 1, which is characterized in that including walking as follows
Suddenly：
Step 1, the synthesis of dimer：Under the conditions of inert nitrogen gas, in cellosolvo dicyandiamide solution, difluoro is joined into pyrrole
Piperidine derivatives are reacted with more hydrated iridium trichlorides at 110~140 DEG C, obtain iridium (III) chlorine bridge dimer；
Step 2, the synthesis of complex of iridium：In the dicyandiamide solution of dichloromethane and methanol, in the presence of Anhydrous potassium carbonate, by iridium
(III) chlorine bridge dimer is reacted with assistant ligand at 30~60 DEG C, obtains blue light iridium (III) complex.
4. the preparation method of blue light ionic type iridium complex according to claim 3, which is characterized in that in the step 1,
The molar ratio of difluoro dipyridyl derivatives and more hydrated iridium trichlorides is 2.2:1.
5. the preparation method of blue light ionic type iridium complex according to claim 3, which is characterized in that in the step 2,
The molar ratio of iridium (III) chlorine bridge dimer and assistant ligand is 1:1.5~10.
6. the preparation method of the blue light ionic type iridium complex according to claim 3 or 5, which is characterized in that the auxiliary
Ligand is one kind in tetrabutyl ammonium cyanide, pyridine, 2,2'- bipyridyls or 1,10- ferrosins.
7. the preparation method of blue light ionic type iridium complex according to claim 3, which is characterized in that the step 1
Synthetic route and the specific steps are：
Step 11, compound 1, the borate of D, four triphenyl phosphorus palladiums are added in the reaction vessel being protected from light, after substituting nitrogen
Tetrabutylammonium bromide, toluene, K is added2CO3Solution reacts 24~48h at 85~100 DEG C, is cooled to room temperature after reaction
It extracts and concentrates through water and dichloromethane solution, compound 2 is obtained by chromatography；
Step 12, by compound 2 and 2,6- difluoro pyridine -3- boric acid, four triphenyl phosphorus palladiums are put into and are protected from light in container, substitute
Ethyl alcohol, toluene, K are added after nitrogen2CO3Solution, at 85~100 DEG C react 24~48h, be cooled to room temperature after reaction through
Water and dichloromethane solution are extracted and are concentrated, and compound 3 is obtained by chromatography；
Step 13, compound 3 and more hydrated iridium trichlorides are put into reaction vessel, cellosolvo is added after substituting nitrogen
And water, 24~48h is reacted at 110~140 DEG C, is cooled to room temperature after reaction, then is obtained with chromatography through filtering
Dimer 4.
8. the preparation method of blue light ionic type iridium complex according to claim 3, which is characterized in that the step 2
Synthetic route and the specific steps are：
Compound 4, assistant ligand and potassium carbonate powder are put into the reaction vessel being protected from light, dichloromethane is added after substituting nitrogen
And methanol, react 12 at 30~60 DEG C~for 24 hours, terminate to be cooled to room temperature when reaction, then obtain with chromatography through extraction
The blue light ionic type iridium complex.
9. a kind of any blue light ionic type iridium complexes of claim 1-2 are as luminescent material in organic electroluminescence
Application in part, organic light emission electrochemical cell device.
10. a kind of organic electroluminescence device, including first electrode, second electrode, and first electrode and second electrode it
Between one or more layers organic function layer for being formed, which is characterized in that include at least one layer of organic function layer claim 1 or
Blue light ionic type iridium complex described in 2.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102712669A (en) * | 2009-11-02 | 2012-10-03 | 南加利福尼亚大学 | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes |
| CN103429370A (en) * | 2011-03-17 | 2013-12-04 | 住友化学株式会社 | Metal complex compositions and mixture thereof |
-
2018
- 2018-06-14 CN CN201810613864.9A patent/CN108586543A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102712669A (en) * | 2009-11-02 | 2012-10-03 | 南加利福尼亚大学 | Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes |
| CN103429370A (en) * | 2011-03-17 | 2013-12-04 | 住友化学株式会社 | Metal complex compositions and mixture thereof |
Non-Patent Citations (2)
| Title |
|---|
| 俞舟: "增溶性空间位阻基团对铱配合物光电性能的影响研究", 《中国优秀硕士学位论文全文数据库工程科技Ⅰ辑》 * |
| 赵吟屏: "蓝色磷光铱配合物的设计合成与光电性质研究", 《中国博士学位论文全文数据库工程科技Ⅰ辑》 * |
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