CN106565605A - Method for preparing tri(1-phenyl-isoquinoline) iridium (III) - Google Patents
Method for preparing tri(1-phenyl-isoquinoline) iridium (III) Download PDFInfo
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- isoquinolin
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 30
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 20
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 title abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 19
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 3
- 238000000746 purification Methods 0.000 claims abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 8
- 230000001681 protective effect Effects 0.000 claims description 8
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 6
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 6
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical class N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 238000000926 separation method Methods 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- NKVDKFWRVDHWGC-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical compound [Ir+3].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NKVDKFWRVDHWGC-UHFFFAOYSA-N 0.000 abstract 2
- 238000010923 batch production Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 21
- -1 chloromethanes Alkane Chemical class 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000012805 post-processing Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 241000555268 Dendroides Species 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention discloses a method for preparing tri(1-phenyl-isoquinoline) iridium (III) through one step. The method comprises the following steps: adding IrCl3.3H2O, 1-phenyl-isoquinoline and Na2CO3 or K2CO3 into a container filled with solvent, carrying out stirring reflux under the condition of nitrogen protection and microwave, cooling to the room temperature, filtering to obtain solid, washing and drying the solid, and adopting a chromatographic column to carry out separation and purification to obtain pure tri(1-phenyl-isoquinoline) iridium (III). According to the method, the raw materials are available, the yield is high, the operation is simple, the reaction time is greatly shortened, the treatment is simple after reaction, the product purity is high, the impurity content is low, and batch production of tri(1-phenyl-isoquinoline) iridium (III) is suitable.
Description
Technical field
The present invention relates to a kind of luminous material of metal iridium organic coordination compound electroluminescent phosphorescence that can apply to electroluminescent field
Material, specifically one kind prepare the method that three (1- phenyl-isoquinolin) close iridium (III).
Background technology
Organic electroluminescence device (Organic Electroluminescence Device or Organic Light-
Emitting Diode, abbreviation OLED), also known as light emitting diode, it is the device lighted under electrical pumping using organic material,
It is the display screen of preferable mobile phone, colour TV etc..It has it is all solid state, from main light emission, brightness height, visual angle width, thickness of thin, can use
The advantages of flexible base board, low in energy consumption, operating temperature range width.And, the device making technics based on organic material are simple, it is easy to
Prepared by large area, environmental friendliness, and the method for manufacturing thin film that operation temperature can be adopted relatively low, low manufacture cost make OLED new one
The unrivaled advantage having in terms of for flat panel display and solid-state illumination and huge application potential, are considered newest one
The solid state light emitter of new generation of " green energy conservation " Display Technique in generation and most competition potential.
Organic phosphorescent material is to study a class phosphor material earlier.In phosphorescent metal complex, due to heavy metal original
The introducing of son, will produce stronger Quantum geometrical phase between metal and part, has mixed the singletstate and triplet state of coordination compound
Energy level, so that the triplet state prohibited originally is achieved to the transition of ground state, substantially increases the luminous efficiency of material.And
Complex of iridium for other heavy metal complexes is easy to process and glow color is easy to adjustment, cause both at home and abroad
The extensive concern of scholars and research.
Relative to high performance green luminescent material, the progress of red illuminating material substantially falls behind, mainly due to HONGGUANG
The defects such as less, the stronger electric charge transfer of the compound energy level difference of transmitting.But as red illuminating material is to realize panchromatic showing
Show one of requisite three primary colours material, and compare the material for lacking at present, so for the research of red phosphorescence material
It is very active always.Through research in recent years, red light material has obtained developing on a large scale very much, is broadly divided into organic molecule main body material
Material, dendroid material of main part and macromolecule material of main part, as the iridium of dendroid material of main part and macromolecule material of main part coordinates
Thing prepare it is more complicated, therefore study at present it is more be the nitrogen heterocyclic that the aryl with iridium as kernel replaces small molecule
Material of main part, while also having obtained many such as Ir (piq)3、Ir(tiq)3、Ir(fliq)3Red phosphorescent emission material, wherein Ir
(piq)3It is the ideal material for realizing saturation HONGGUANG.
But red phosphorescent complex of iridium (C^N)3The synthesis of Ir, is generally adopted by the article that Huo S et al. are delivered
Method (Huo S et al. Inorganic Chemistry, 2006,45 (8):3155-7.), dibromo was prepared into before this
Endo compound is [(C^N)2IrBr]2Or the intermediate such as compound of part based on acetylacetone,2,4-pentanedione, then react with respective ligand again
Arrive, cause synthesize needs raw material amount it is larger, synthetic reaction is more complicated, and post processing is loaded down with trivial details, i.e. consumed energy, in addition it is also necessary to longer
Time, it is unfavorable to commercial production, hinder its application in OLED.Therefore, develop (C^N)3The new synthetic method of Ir, it is right
Promote its application in OLED that there is extremely important learning value and realistic meaning.
The content of the invention
It is an object of the present invention to provide one kind prepares three (1- phenyl-isoquinolin) closes iridium (III)（Ir(piq)3）Method, should
Synthetic method has relatively big difference with existing method；As existing method generally requires the reaction of more than two steps or two steps so that close
More complicated into reacting, post processing is loaded down with trivial details, i.e. consumed energy, in addition it is also necessary to longer time；And new method of the present invention realizes HONGGUANG
Iridium phosphorescent complexes Ir (piq) of transmitting3One-step synthesis, simplify synthesis step and post processing, reduce raw material dosage, it is bright
It is aobvious to shorten the response time, improve reaction efficiency.
Above-mentioned red emission iridium phosphorescent complexes Ir (piq)3Chemical structural formula is as follows：(CAS：435293-93-9)
。
The method uses IrCl3·3H2O is raw material, prepares iridium phosphorescent complexes Ir (piq) of red emission3；Simplify
Synthesis step and post processing, hence it is evident that shorten the response time, improve reaction efficiency.
The technical solution used in the present invention is：By IrCl3·3H2O, 1- phenyl isoquinolin quinoline (piq), Na2CO3Or K2CO3Plus
Enter in the there-necked flask equipped with glycerol or diethylene glycol monoethyl ether and stir, under nitrogen protective condition, in microwave power 290～
5～7min is stirred at reflux under the conditions of 300W, room temperature is cooled to, solid difference deionized water, absolute ethanol washing, obtain after filtration
Target product Ir (piq)3Crude product；The subtractive process of target product is as follows：After solid drying, with post separation is chromatographed, (chloroform is
Eluent), collect concentrate eluant, dry Ir (piq)3Sterling；Its chemical reaction route is：
。
IrCl in the step3·3H2O is 1 with 1- phenyl isoquinolin quinoline (piq) mol ratios:4~6；IrCl3·3H2O with
Na2CO3Or K2CO3Mol ratio is 1:5~9.
The glycerol or diethylene glycol monoethyl ether and IrCl3·3H2The volume mass of O is than m L:G is 20～50:1.
Compared with prior art, the beneficial effects are mainly as follows：
Existing organic metal complex of iridium Ir (piq)3Synthetic method, generally require two steps or reactions more than two steps, first
It is to be prepared into dibromo endo compound [(C^N)2IrBr]2Or the intermediate such as compound of part based on acetylacetone,2,4-pentanedione, then again with 1-
Phenyl isoquinolin quinoline (piq) reaction obtain, cause synthesize needs raw material amount it is larger, synthetic reaction is more complicated, and post processing is loaded down with trivial details,
That is consumed energy, in addition it is also necessary to longer time；New method of the present invention causes iridium phosphorescent complexes Ir (piq) of red emission3's
Synthesis realizes one-step synthesis, simplifies synthesis step and post processing, hence it is evident that shorten the response time, reduces raw material dosage,
Improve reaction efficiency.
Specific embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This.
Embodiment 1：
Title removes the IrCl of 5.0 g3·3H2The 1- phenyl isoquinolin quinolines of O, 11.66g, the Na of 7.53g2CO3It is placed in there-necked flask, adds
The glycerol of 100mL, under nitrogen protective condition, microwave heating (power 290W) backflow 5min, after being cooled to room temperature, is filtered, Gu
Body difference deionized water, absolute ethanol washing, use silica gel column chromatography post separation after solid drying（300-400 mesh）, three chloromethanes
Alkane is eluant, collects concentrate eluant, and vacuum drying had both obtained 11.26g Ir (piq)3, yield is 98.5%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
66.89%, H, 3.75%, N, 5.22% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.17；(3)
Proton nmr spectra1H NMR (500 MHz, CDCl3)：In ppm: 8.94 (m, 3H), 8.19 (d, 3H,J = 7.8
Hz), 7.71 (m, 3H), 7.60 (m, 6H), 7.34 (d, 3H, J =6.1Hz), 7.10 (d, 3H, J =
6.1Hz), 6.94–6.97 (m, 6H), 6.84 (t, 3H, J= 7.4 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Embodiment 2：
Title removes the IrCl of 5.0g3·3H2The 1- phenyl isoquinolins quinoline and the K of 11.76g of O, 13.12g2CO3It is placed in there-necked flask, adds
The glycerol of 135mL, under nitrogen protective condition, microwave heating (power 295W) backflow 6min, after being cooled to room temperature, is filtered, point
Other deionized water, washing with alcohol, use silica gel column chromatography post separation after the solid drying for obtaining（300-400 mesh）, chloroform is
Eluent, collects concentrate eluant, and vacuum drying had both obtained 11.3g Ir (piq)3, yield is 98.8%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
66.89%, H, 3.75%, N, 5.27% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.2；(3) core
Magnetic resonance hydrogen is composed1H NMR (500 MHz, CDCl3)：In ppm: 8.95 (m, 3H), 8.20 (d, 3H,J = 7.9
Hz), 7.73 (m, 3H), 7.61 (m, 6H), 7.31 (d, 3H, J =6.0Hz), 7.09 (d, 3H, J =
6.1Hz), 6.95–6.99 (m, 6H), 6.84 (t, 3H, J= 7.4 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Embodiment 3：
Title removes the IrCl of 5.0g3·3H2The 1- phenyl isoquinolins quinoline and the Na of 12.04g of O, 14.57g2CO3It is placed in there-necked flask, plus
Enter the diethylene glycol monoethyl ether of 200mL, under nitrogen protective condition, microwave heating (power 295W) backflow 6min is cooled to room temperature
Afterwards, filter, respectively deionized water, absolute ethanol washing, after the solid drying for obtaining, use silica gel column chromatography post separation（300-400
Mesh）, chloroform is eluent, collects concentrate eluant, and vacuum drying had both obtained 9.91g Ir (piq)3, yield is 86.7%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
67.07%, H, 3.79%, N, 5.19% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.20；(3)
Proton nmr spectra1H NMR (500 MHz, CDCl3)：In ppm: 8.93 (m, 3H), 8.21 (d, 3H,J = 7.9
Hz), 7.75 (m, 3H), 7.61 (m, 6H), 7.28 (d, 3H, J =6.1Hz), 7.11 (d, 3H, J =
6.2Hz), 6.94–6.98 (m, 6H), 6.78 (t, 3H, J= 7.2 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Embodiment 4：
Title removes the IrCl of 5.0g3·3H2The 1- phenyl isoquinolins quinoline and the Na of 12.04g of O, 14.57g2CO3It is placed in there-necked flask, plus
Enter the glycerol of 200mL, under nitrogen protective condition, microwave heating (power 300W) backflow 7min, after being cooled to room temperature, is filtered,
Deionized water, absolute ethanol washing, use silica gel column chromatography post separation after the solid drying for obtaining respectively（300-400 mesh）, trichlorine
Methane is eluent, collects concentrate eluant, and vacuum drying had both obtained 11.35g Ir (piq)3, yield is 99.3%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
67.11%, H, 3.74%, N, 5.22% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.22；(3)
Proton nmr spectra1H NMR (500 MHz, CDCl3)：In ppm: 8.96 (m, 3H), 8.17 (d, 3H,J = 7.8
Hz), 7.72 (m, 3H), 7.63 (m, 6H), 7.31 (d, 3H, J =6.1Hz), 7.07 (d, 3H, J =
6.1Hz), 6.94–6.99 (m, 6H), 6.82 (t, 3H, J= 7.4 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Embodiment 5：
Title removes the IrCl of 5.0g3·3H2The 1- phenyl isoquinolins quinoline and the K of 15.68g of O, 14.57g2CO3It is placed in there-necked flask, adds
The diethylene glycol monoethyl ether of 250mL, under nitrogen protective condition, microwave heating (power 300W) backflow 7min, after being cooled to room temperature,
Filter, respectively deionized water, absolute ethanol washing, after the solid drying for obtaining, use silica gel column chromatography post separation（300-400 mesh）,
Chloroform is eluent, collects concentrate eluant, and vacuum drying had both obtained 9.56g Ir (piq)3, yield is 83.6%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
67.13%, H, 3.69%, N, 5.21% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.18；(3)
Proton nmr spectra1H NMR (500 MHz, CDCl3)：In ppm: 8.95 (m, 3H), 8.13 (d, 3H,J = 7.6
Hz), 7.76 (m, 3H), 7.59 (m, 6H), 7.33 (d, 3H, J =6.2Hz), 7.12 (d, 3H, J =
6.2Hz), 6.94–6.99 (m, 6H), 6.81 (t, 3H, J= 7.4 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Embodiment 6：
Title removes the IrCl of 5.0g3·3H2The 1- phenyl isoquinolins quinoline and the K of 13.55g of O, 17.49g2CO3It is placed in there-necked flask, adds
The glycerol of 250mL, under nitrogen protective condition, microwave heating (power 300W) backflow 7min, after being cooled to room temperature, is filtered, point
Other deionized water, absolute ethanol washing, use silica gel column chromatography post separation after the solid drying for obtaining（300-400 mesh）, three chloromethanes
Alkane is eluent, collects concentrate eluant, and vacuum drying had both obtained 11.27g Ir (piq)3, yield is 98.6%.
Feature structure parameter：(1) elementary analysiss：Theoretical value C, 67.14%, H, 3.76%, N, 5.22% and measured value C,
67.13%, H, 3.71%, N, 5.21% is consistent；(2) mass spectrum (EI):M/z theoretical values：805.21, measured value：805.18；(3)
Proton nmr spectra1H NMR (500 MHz, CDCl3)：In ppm: 8.94 (m, 3H), 8.19 (d, 3H,J = 7.8
Hz), 7.70 (m, 3H), 7.63 (m, 6H), 7.29 (d, 3H, J =6.1Hz), 7.08 (d, 3H, J =
6.1Hz), 6.94–6.98 (m, 6H), 6.84 (t, 3H, J= 7.4 Hz)；These parameters meet complex of iridium Ir
(piq)3Chemical constitution.
Claims (3)
1. one kind prepares the method that three (1- phenyl-isoquinolin) close iridium (III), it is characterised in that：By IrCl3·3H2O, 1- phenyl
Isoquinolin, Na2CO3Or K2CO3It is added in the container equipped with glycerol or diethylene glycol monoethyl ether, under nitrogen protective condition,
5～7min is stirred at reflux under the conditions of 290～300W of microwave power, after being cooled to room temperature, solid is filtered to obtain, is then spent respectively
Ionized water, absolute ethanol washing, obtain target product crude product；With chromatography column separating purification after crude product drying, chloroform is eluting
Liquid, collects concentrate eluant, obtains three (1- phenyl-isoquinolin) and close iridium (III) after being dried.
It is 2. according to claim 1 to prepare the method that three (1- phenyl-isoquinolin) close iridium (III), it is characterised in that：
IrCl3·3H2O is 1 with 1- phenyl isoquinolin quinolines mol ratio:4～6；IrCl3·3H2O and Na2CO3Or K2CO3Mol ratio is 1:5～
9。
It is 3. according to claim 1 to prepare the method that three (1- phenyl-isoquinolin) close iridium (III), it is characterised in that：The third three
Alcohol or diethylene glycol monoethyl ether and IrCl3·3H2The volume mass of O compares mL:G is 20～50:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610911216.2A CN106565605A (en) | 2016-10-20 | 2016-10-20 | Method for preparing tri(1-phenyl-isoquinoline) iridium (III) |
Applications Claiming Priority (1)
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