CN101280186A - Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof - Google Patents
Photophosphorescence material contain iridium complex of phenylquinoline and acidamide group and preparation thereof Download PDFInfo
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- CN101280186A CN101280186A CNA2008100241356A CN200810024135A CN101280186A CN 101280186 A CN101280186 A CN 101280186A CN A2008100241356 A CNA2008100241356 A CN A2008100241356A CN 200810024135 A CN200810024135 A CN 200810024135A CN 101280186 A CN101280186 A CN 101280186A
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Abstract
Disclosed is iridium complex electrophosphorescent material which contains phenylquinoline and amide group and the preparation method, which belong to the organic electroluminescent material technical field. The invention discloses a class of electrophosphorescent material which contains the iridium complex composed of phenylquinoline and amide which are two types of bidentate ligands; the preparation method of the iridium complex electrophosphorescent material includes that: firstly, amide is obtained through the reaction of amine derivatives and acyl chloride; and then the amide and chloro-bridge dimerization complex (pq)2Ir(u-Cl)2Ir(pq)2 are processed with ligand exchange reaction under the existence of sodium alkoxide; and then the obtained powder product is processed with vacuum drying; the iridium complex electrophosphorescent material which contains phenylquinoline and amide group is obtained through column chromatography after night. The ligands which contain phenylquinoline and amide structure adopted by the iridium complex electrophosphorescent material has the advantages of easy synthesis, low cost, high production rate and easy modification; the synthesized iridium complex has strong phosphorescent emission performance in the solution with room temperature; the electrophosphorescent material in the invention can be used as the functional materials in the organic electroluminescent devices.
Description
Technical field
Contain the iridium complex electroluminescent phosphor material and the preparation thereof of phenylquinoline and amide group, belong to the electroluminescent organic material technical field.The present invention relates generally to organometallic complex luminescent material and the preparation thereof that iridium and acid amides and phenylquinoline form.
Background technology
Organic Light Emitting Diode (OLED) and the panel display screen that makes up thereof have been generally believed luminosity and luminous efficiency height, driving voltage is low, response speed is fast, operating temperature range is wide, forming process is more convenient, be convenient to numerous advantages such as extensive, big area production, have the type material that develop on a large scale very much potential and the market development are worth and become a class.The people such as Tang of Kodak company have invented a metal-organic complex oxine aluminium (Alq with sandwich structure in patent US4356429 in 1987
3), this material has premium propertiess such as high brightness, high-quantum efficiency, high-luminous-efficiency, and the organic electroluminescent field has been entered among the process of industrialization.Subsequently in 1997, Forrest etc. utilize the heavy atoms effect of transition metal, strong spin-track the coupling that produces, thus effective singlet increased to the intersystem crossing between the triplet state, made full use of all form of energy that comprise singlet and triplet state.From then on the research and development of organic flat-panel display device have entered a new period.
The common transition metal that electroluminescent material adopted mainly contains Ir (III), Pt (II), Re (I), Os (II) etc. at present.Metal iridium complex owing to its good stability, radiative lifetime is short and efficient highly becomes in the research of these transition metal at most, the most detailed.By ligand modified, the luminescent spectrum of complex of iridium can in very large range obtain modulation according to existing research.
The research of complex of iridium mainly is the selection and the modification of part, introduces suction/electron donating group on part, changes the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) of title complex, promptly changes the transition of electron energy level, thereby has changed luminescent spectrum.The part of complexes of red light iridium employing efficiently mainly contains benzothiophene kind and phenyl isoquinolin quinoline class at present.These part ubiquity synthetic method complexity, the cost costliness is difficult to carry out problems such as suitability for industrialized production.Therefore, the new good part of exploitation is used as complexes of red light iridium and seems important unusually.
Summary of the invention
The purpose of this invention is to provide the iridium complex electroluminescent phosphor material and the preparation thereof that contain phenylquinoline and amide group, design the iridium complex electroluminescent phosphor material that a class has phenylquinoline and amide structure, this material can be plated in by the method for evaporation makes OLED on the ito glass.The part that contains phenylquinoline and amide structure that the present invention is selected, have be easy to synthesize, cost is low, productive rate is high, be easy to advantages such as modification.The iridium metal complex that obtains at room temperature has stronger phosphorescence luminescent properties in the solution.
The present invention is that to find to comprise the amide derivatives of nitrogen oxygen be the ancient part of a class with bidentate structure testing the back in a large number, has advantage such as to be easy to synthesize, coordination ability is good.Simultaneously analysis-by-synthesis find behind a large amount of existing documents that the amides part that comprises nitrogen oxygen is very big to the title complex property effect with tetra-atomic ring and transition-metal coordination.So, the contriver adopts and is easy to synthetic phenylquinoline class part as main part, with the amides part is co-ligand, has synthesized the title complex that a class combines present common complex of iridium advantage, especially the complex of iridium that has great advantage on luminescent properties, synthetic method and production cost.
Technical scheme of the present invention: contain the iridium complex electroluminescent phosphor material of phenylquinoline and amide group, this material structure formula is as follows:
C^N is 2-phenylquinoline or (4-bromine)-2-phenylquinoline, R
1, R
2Be methyl, the tertiary butyl or phenyl.
The C^N structural formula is:
X is: H, Br
Described organic electrofluorescent iridium complex material, C^N are the 2-phenylquinoline, R
1Be phenyl, R
2Be methyl.
Described organic electrofluorescent iridium complex material, C^N are the 2-phenylquinoline, R
1Be phenyl, R
2Be the tertiary butyl.
Described organic electrofluorescent iridium complex material, C^N are the 2-phenylquinoline, R
1Be phenyl, R
2Be phenyl.
Described organic electrofluorescent iridium complex material, C^N are (4-bromine)-2-phenylquinoline, R
1Be phenyl, R
2Be methyl.
The preparation method of described iridium complex electroluminescent phosphor material: at first obtain acid amides by sulfonamide derivatives and acyl chloride reaction; Acid amides again with chlorine bridge dimerization title complex (pq)
2Ir (μ-Cl)
2Ir (pq)
2Under the condition that sodium alkoxide exists, carry out ligand exchange reaction: chlorine bridge dimerization complex of iridium and acid amides are dissolved in the cellosolvo N with 1: 2.5 mol ratio
2Environment adds down excessive sodium methylate, 90-100 ℃ following stirring reaction 8-24 hour, add elutriation and go out powder; After the powder vacuum-drying that obtains spent the night, column chromatography obtained containing the iridium complex electroluminescent phosphor material of phenylquinoline and amide group.
The application of described iridium complex electroluminescent phosphor material: be used to prepare organic electroluminescence device.
Beneficial effect of the present invention: the part that contains phenylquinoline and amide structure that the present invention is selected, have be easy to synthesize, cost is low, productive rate is high, be easy to advantages such as modification.The iridium metal complex that synthesizes at room temperature has stronger phosphorescence luminescent properties in the solution.Phosphor material of the present invention can be used as the functional material in the organic electroluminescence device.
Embodiment
The present invention is further illustrated below in conjunction with specific embodiment that the contriver provides.
The preparation method of metal iridium complex of the present invention: at first obtain acid amides, again with the chlorine bridge dimerization title complex (pq) of 2-phenylquinoline (pq) class part by sulfonamide derivatives and acyl chloride reaction
2Ir (μ-Cl)
2Ir (pq)
2Carry out ligand exchange reaction under certain condition, obtain target product.
(1) acid amides is synthetic:
Work as R
1=Me, R
2During=Ph, the synthetic method that is Acetanilide is: after aniline and diacetyl oxide were refluxed 4 hours in acetic acid with mol ratio at 1: 2, the solution that reaction obtains is poured in the frozen water, and the solid that suction filtration is separated out can obtain Acetanilide with the solid recrystallization in ethanol that obtains then.
Work as R
1=Ph, R
2During=Ph, promptly benzanilide is synthetic: be raw material with the phenylformic acid earlier, at the excessive SOCl of solvent-free adding down
2Reaction generates Benzoyl chloride, takes out excessive sulfur oxychloride.And add the 20mL ether at twice and be evacuated to constant weight once more, obtain pure acyl chlorides.Drop in the new steaming aniline with the acyl chlorides that obtains then, drip the solid that after washing is separated out, adopt ethyl alcohol recrystallization to obtain benzanilide.Its structural formula is:
(2) chlorine bridge dimerization complex of iridium is synthetic
Press document (S.Sprouse, K.A.King, P.J.Spellane, and R.J.Watts, J.Am..Chem.Soc.1984,106, the chlorine bridge dimerization complex of iridium (pq) of method synthesis of phenyl quinoline (pq) 6647-6653)
2Ir (μ-Cl)
2Ir (pq)
2Phenylquinoline and iridous chloride were refluxed 24 hours in water and cellosolvo (volume ratio 1: 3) mixed solvent, and reaction finishes postcooling to room temperature (5 ℃-25 ℃), adds 10%HCl solution, filters and obtains red powder.And use methanol wash, vacuum-drying gets target product.
(3) final product is synthetic
Chlorine bridge dimerization complex of iridium and acid amides (mol ratio 1: 2.5) are dissolved in the cellosolvo N
2Environment adds down excessive sodium methylate, 90-100 ℃ following stirring reaction 8-24 hour.Add elutriation and go out powder, after the powder vacuum-drying that obtains is spent the night.Silica gel column chromatography obtains final product.
Below be the specific embodiment that the contriver provides:
Embodiment 1: part is complex of iridium synthetic of Acetanilide and phenylquinoline.Its structural formula is as follows:
(1) preparation of Acetanilide:
Add 9.3g (0.1mol) aniline and 20mL (0.05mol) acetic acid in the 250mL round-bottomed flask, Dropwise 5 .1g (0.05mol) diacetyl oxide under agitation is heated to backflow then, after 4 hours, stops to reflux.Reaction soln is poured in the frozen water, separated out a large amount of white solids, the white solid that suction filtration obtains is collected white solid and is carried out recrystallization with about 90mL dissolve with ethanol.Obtain white plates crystal 10.9g (productive rate 81.0%), m.p=114 ℃.
(2) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2Synthetic:
Get 0.352g (0.05mmol) hydration iridous chloride, 0.625g (0.12mmol) the 2-phenylquinoline is in the 100mL there-necked flask, nitrogen environment adds in the mixed solvent of 15mL2-ethoxy ethanol and 5mL water down, reflux 24 hours, reaction finishes postcooling to room temperature, add 20mL10%HCl solution and separate out red precipitate, the powder that obtains after the filtration gets product 0.869g (productive rate: 68.42%) with methyl alcohol and petroleum ether.
(3) metal iridium complex is synthetic:
Get 0.063g (0.5mmol) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2And 0.04g (1.25mmol) Acetanilide is dissolved in the 10mL ethoxy ethanol, adds the 0.05g sodium methylate then, is warming up to 100 ℃ of reactions 24 hours under the nitrogen environment.After reaction finishes, add 30mL water, filter the pressed powder that obtains separating out.Vacuum-drying is spent the night.Carry out column chromatography with methylene dichloride and sherwood oil (volume ratio 5: 4) system and purify, obtain red solution drain 0.058g (productive rate: 51.91%).IR(KBr)：3069m，29612930w，1453?1439?1411?s，1094?1024?s，756?s，732?697?670?m.1H?NMR(400MHz)d(CDCl
3)：1.92(s，3H，-CH
3)，5.7-8.5(-ArH)。
Embodiment 2: part is metal iridium complex synthetic of benzanilide and phenylquinoline, and its structural formula is as follows:
(1) preparation of benzanilide
Add 12.4g (0.1mol) phenylformic acid in the single port flask of 250mL, add 25mL (1.05mol) sulfur oxychloride, reflux absorbs the tail gas that produces with aqueous sodium hydroxide solution.React after 1 hour, phenylformic acid all dissolves, and stops heating, takes out sulfur oxychloride excessive in the dereaction solution to the flask constant weight.And add the 20mL ether at twice and be evacuated to constant weight once more, obtain Benzoyl chloride 24.2mL.Drop among the aniline 9.3g (0.1mol) with the Benzoyl chloride that obtains then, drip the solid that after washing is separated out, adopt ethyl alcohol recrystallization to obtain benzanilide, obtain white needle-like crystals 35.5g (productive rate: 89.62%).m.p＝163.2℃。
(2) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2Synthetic:
The preparation method is with embodiment 1.
(3) metal iridium complex is synthetic:
Get 0.063g (0.5mmol) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2And 0.054g (1.25mmol) benzanilide is dissolved in the 10mL ethoxy ethanol, adds the 0.05g sodium methylate then, is warming up to 100 ℃ of reactions 24 hours under the nitrogen environment.After reaction finishes, add 30mL water, filter the pressed powder that obtains separating out.Vacuum-drying is spent the night.Carry out column chromatography with methylene dichloride and sherwood oil (volume ratio 1: 1) system and purify, obtain red solution drain 0.023g (productive rate: 56.2%).IR(KBr)：3053m，29612926w，1453?1438?1412?s，1094?1024?s，756?s，732?700?670?m.1H?NMR(400MHz)d(CDCl
3)：5.7-8.5(-ArH)。
Embodiment 3: the metal iridium complex of part benzoyl TERTIARY BUTYL AMINE and 2-phenylquinoline synthetic.Its structural formula is:
(1) preparation of benzoyl TERTIARY BUTYL AMINE:
Add 12.4g (0.1mol) phenylformic acid in the single port flask of 250mL, add the 25mL sulfur oxychloride, reflux absorbs the tail gas that produces with aqueous sodium hydroxide solution.React after 1 hour, phenylformic acid all dissolves, and stops heating, takes out sulfur oxychloride excessive in the dereaction solution to the flask constant weight.And add the 20mL ether at twice and be evacuated to constant weight once more, obtain Benzoyl chloride 23mL.Drop in the dichloromethane solution of 7.3g (0.1mol) TERTIARY BUTYL AMINE with the Benzoyl chloride that obtains then, drain solvent after dripping, the solid that washing obtains adopts ethyl alcohol recrystallization to obtain the benzoyl TERTIARY BUTYL AMINE, obtains white needle-like crystals 15.5g (productive rate: 85%).m.p＝135.8℃。
(2) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2Synthetic: the preparation method is with embodiment 1.
(3) metal iridium complex is synthetic:
Get 0.063g (0.5mmol) chlorine bridge dimerization complex of iridium (pq)
2Ir (μ-Cl)
2Ir (pq)
2And 0.034g (1.25mmol) benzoyl TERTIARY BUTYL AMINE is dissolved in the 10mL ethoxy ethanol, adds the 0.05g sodium methylate then, is warming up to 100 ℃ of reactions 24 hours under the nitrogen environment.After reaction finishes, add 30mL water, filter the pressed powder that obtains separating out.Vacuum-drying is spent the night.Carry out column chromatography with methylene dichloride and sherwood oil (volume ratio 1: 1) system and purify, obtain red solution drain 0.032g (productive rate: 78.35%).IR(KBr)：3053m，29612926w，1458?1445?1410?s，1094?1025?s，756?s，732?697?m.1H?NMR(400MHz)d(CDCl
3)：1.8(s，9H，CH
3)，5.9-8.2(-ArH)。
Embodiment 4: the metal iridium complex of part benzoyl TERTIARY BUTYL AMINE and (4-bromine) 2-phenylquinoline synthetic.Its structural formula is:
(1) preparation of Acetanilide:
The preparation method is embodiment 1 roughly the same.
(2) band Br substituent chlorine bridge dimerization complex of iridium (Br-pq)
2Ir (μ-Cl)
2Ir (Br-pq)
2Synthetic:
The preparation method is embodiment 1 roughly the same.
(3) metal iridium complex is synthetic:
Get 0.082g (0.5mmol) band Br substituent chlorine bridge dimerization complex of iridium and 0.04g (1.25mmol) Acetanilide and be dissolved in the 10mL ethoxy ethanol, add the 0.05g sodium methylate then, be warming up to 90 ℃ of reactions 20 hours under the nitrogen environment.After reaction finishes, add 30mL water, filter the pressed powder that obtains separating out.Vacuum-drying is spent the night.Carry out column chromatography with methylene dichloride and sherwood oil (volume ratio 3: 1) system and purify, obtain solution drain 0.049g (productive rate: 54.44%).IR(KBr)：3026?3034?m，2958?w，1462?14381422?s，1096?1025?s，761?s，690?m.1H?NMR(400MHz)d(CDCl
3)：2.2(s，3H，CH
3)，5.6-8.3(-ArH)。
Claims (7)
1, the iridium complex electroluminescent phosphor material that contains phenylquinoline and amide group is characterized in that this material structure formula is as follows:
C^N is 2-phenylquinoline or (4-bromine)-2-phenylquinoline, R
1, R
2Be methyl, the tertiary butyl or phenyl.
2, iridium complex electroluminescent phosphor material according to claim 1 is characterized in that C^N is the 2-phenylquinoline, R
1Be phenyl, R
2Be methyl.
3, iridium complex electroluminescent phosphor material according to claim 1 is characterized in that C^N is the 2-phenylquinoline, R
1Be phenyl, R
2Be the tertiary butyl.
4, iridium complex electroluminescent phosphor material according to claim 1 is characterized in that C^N is the 2-phenylquinoline, R
1Be phenyl, R
2Be phenyl.
5, iridium complex electroluminescent phosphor material according to claim 1 is characterized in that C^N is (4-bromine)-2-phenylquinoline, R
1Be phenyl, R
2Be methyl.
6, the preparation method of the described iridium complex electroluminescent phosphor material of claim 1 is characterized in that: at first obtain acid amides by sulfonamide derivatives and acyl chloride reaction; Acid amides again with chlorine bridge dimerization title complex (pq)
2Ir (μ-Cl)
2Ir (pq)
2Under the condition that sodium alkoxide exists, carry out ligand exchange reaction: chlorine bridge dimerization complex of iridium and acid amides are dissolved in the cellosolvo N with 1: 2.5 mol ratio
2Environment adds down excessive sodium methylate, 90-100 ℃ following stirring reaction 8-24 hour, add elutriation and go out powder; After the powder vacuum-drying that obtains spent the night, silica gel column chromatography obtained containing the iridium complex electroluminescent phosphor material of phenylquinoline and amide group.
7, the application of the described iridium complex electroluminescent phosphor material of claim 1 is characterized in that: be used to prepare organic electroluminescence device.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPWO2010061625A1 (en) * | 2008-11-28 | 2012-04-26 | 独立行政法人理化学研究所 | New compounds and their use |
| CN103045233A (en) * | 2012-12-24 | 2013-04-17 | 江南大学 | Amido organometallic iridium complex luminescent material and preparation method thereof |
| CN105588822A (en) * | 2015-12-11 | 2016-05-18 | 江南大学 | Method for detecting tryptophan based on ionic iridium complex phosphorescence quenching |
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2008
- 2008-05-16 CN CNA2008100241356A patent/CN101280186A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2010061625A1 (en) * | 2008-11-28 | 2012-04-26 | 独立行政法人理化学研究所 | New compounds and their use |
| JP5549015B2 (en) * | 2008-11-28 | 2014-07-16 | 独立行政法人理化学研究所 | New compounds and their use |
| US8808878B2 (en) | 2008-11-28 | 2014-08-19 | Riken | Compound and use thereof |
| CN103045233A (en) * | 2012-12-24 | 2013-04-17 | 江南大学 | Amido organometallic iridium complex luminescent material and preparation method thereof |
| CN105588822A (en) * | 2015-12-11 | 2016-05-18 | 江南大学 | Method for detecting tryptophan based on ionic iridium complex phosphorescence quenching |
| CN105588822B (en) * | 2015-12-11 | 2018-08-07 | 江南大学 | A method of tryptophan is detected based on ionic type iridium complex phosphorescence quenching |
| CN109054035A (en) * | 2018-06-29 | 2018-12-21 | 中国科学院合肥物质科学研究院 | A kind of nano flower-like Ti-MOF fluorescence probe material and the preparation method and application thereof |
| CN109054035B (en) * | 2018-06-29 | 2020-11-10 | 中国科学院合肥物质科学研究院 | Nanometer flower-shaped Ti-MOF fluorescent probe material and preparation method and application thereof |
| CN110872329A (en) * | 2019-11-01 | 2020-03-10 | 深圳大学 | Iridium complex and preparation method and application thereof |
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