CN101182412A - Amides Ir organometallic complex electroluminescent material and uses thereof - Google Patents
Amides Ir organometallic complex electroluminescent material and uses thereof Download PDFInfo
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- CN101182412A CN101182412A CNA2007101992663A CN200710199266A CN101182412A CN 101182412 A CN101182412 A CN 101182412A CN A2007101992663 A CNA2007101992663 A CN A2007101992663A CN 200710199266 A CN200710199266 A CN 200710199266A CN 101182412 A CN101182412 A CN 101182412A
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Abstract
The invention discloses amide Ir metal organic complex phosphorus optoelectronic material. The metal organic complex is the metal complex containing a 2-phenyl pyridine structure; the molecular structural formula is (L<2>)2Ir(ayl); in the formula, L<2> is bidentate ligand containing the 2-phenyl pyridine structure; ayl is bidentate ligand containing a amide structure. The iridium metal complex synthesized in the invention has strong luminous performance of phosphorescence in the solution at the room temperature, and can be used as the functional material for organic electroluminescence devices.
Description
Technical field
The present invention relates to a kind of amides metal complexes, be specifically related to amides Ir (III) a metal-organic complex phosphorescence electroluminescent material that a class can be used for the electroluminescent field.
Background technology
Organic electroluminescent (EL) is meant organic materials under electric field action, electric energy is converted into a kind of luminescence phenomenon of luminous energy.About organic electroluminescence device (OEL) is that the research of Organic Light Emitting Diode (OLED) originates in the fifties in last century.By 1987, people such as Eastern Kodak company's T ang have invented the device of sandwich structure in document and patent US4356429, adopt fluorescence efficiency very high, electron transport property and organic small molecule material-oxine aluminium (Alq that can usefulness vacuum plating arranged
3), make the high-quality thin film of even compact with aromatic diamine with hole transport characteristic, and make organic EL device, this material has premium propertiess such as high brightness, high-quantum efficiency, high-luminous-efficiency, make the research work of electroluminescent organic material enter a brand-new era, indicate that the organic electroluminescent field has entered the epoch of breeding practicability.But owing to be subjected to the restriction of spin statistical theory, the limit of the theoretic internal quantum efficiency of fluorescent material is 25%, how to utilize fully the phosphorescence that accounts for energy 75% with realize higher efficient become when thing suddenly.1997, Forrest etc. found the phosphorescence electro optical phenomenon, have broken through the electroluminescent organic material quantum yield and have been lower than 25% restriction, make the research of organic flat-panel display device enter another new period.
In the research of electroluminescent organic material subsequently, the ring title complex of small molecules doping type transition metal becomes the emphasis of people's research, as iridium, and ruthenium, the title complex of platinum etc.The advantage of this class title complex is that they can obtain very high emitted energy (M.A.Baldo, et al, Appl.Phys.Letters, 1999,74,4) from the triplet state of self.And metal iridium compound wherein, since the good stability of its compound, reaction conditions gentleness in building-up process, and have very high electroluminescent properties, in research process subsequently, accounting for leading status always.
Studies show that, the transition metal organic coordination compound belongs to the luminous organic coordination compound luminescent material of part of acceptor center atom perturbation, part plays a decisive role to its stability and spectrum property, therefore can obtain performance by ligand modified, the phosphor material that glow color is different, about the research of Ir title complex mainly is modification and modification to part, on part, introduce suction/electron donating group, change the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) of title complex, make the character of compound that change as luminescent material take place more to help.But modification and modification to part often need through complicated chemical reaction, and the difficulty that this will certainly increase chemical reaction on the one hand reduces the transformation efficiency of expecting final product from former on the other hand, increases the production cost of material.And in the existing research, new kind part is paid close attention to also few.
Summary of the invention
The purpose of this invention is to provide Ir (III) a metal-organic complex phosphorescence electroluminescent material that a class contains amide structure, this material can be plated in by the method for evaporation makes OLED on the ito glass, also can be aggregated on the polymer by the simple ligand modified metal complexes that will synthesize, make PLED by spin coating then, solving the decomposes that the small molecules luminescent material is prone in evaporate process, anti-crystallization such as can differ from shortcoming.
In order to obtain above-mentioned part, design of the present invention and technical scheme are as follows:
The selection of assistant ligand should be followed easily and metal-complexing and certain research application foundation is arranged is prerequisite, the contriver in synthetic study find after the various kinds of document, in existing research, nitrogen and Sauerstoffatom have very sophisticated research in metal complexes synthetic, but existing research generally all is to cooperate one five yuan or six-ring and metal-complexing with nitrogen oxygen, and comprises nitrogen oxygen and also do not occur with the report of tetra-atomic ring and metal-complexing.In research subsequently, the contriver finds to comprise the amide derivatives of nitrogen oxygen, although it has had long-term research as part in Organometallic Chemistry, but it does not also have any application in luminescent metal phosphor material synthetic, and it is again with tetra-atomic ring and metal-complexing, design imagination according to the invention is so it is the assistant ligand that the present invention relates to metal complexes that the contriver adopts amide derivatives; Since the good stability of complex of iridium, reaction conditions gentleness in building-up process, so the contriver adopts the metal iridium core of compounds for this reason; Main part contriver selects the phenylpyridine analog derivative, because it is cheap, and modifies easily.
Amides Ir organometallic complex phosphorescence electroluminescent material, this material are a kind of metal complexess of the 2-of containing phenylpyridine structure, and its molecular structural formula is (L
2)
2Ir (ayl), L in the formula
2Be the bidentate ligand that contains 2-phenylpyridine structure, ayl is the bidentate ligand that contains amide structure.
The described bidentate ligand ayl structure that contains amide structure is:
R
2Be hydrogen, alkyl, iso-alkyl, aromatic base or alkylene; R
1Be aromatic base or substituted aromatic base, described aromatic base is the group that phenyl, naphthyl etc. have aromaticity.Because aromatic base has big π key and inflexible structure, this is good for improving luminescent properties.Described alkyl carbon number is C
1-C
6, described iso-alkyl carbon number is C
3-C
6
Further, the above-mentioned bidentate ligand ayl that contains amide structure has following structure:
Wherein, R
3Be selected from hydrogen, hydroxyl, alkyl, iso-alkyl, alkoxyl group, halogen atom, aromatic base or alkylene, described alkyl and alkoxyl group carbon number are C
1-C
6, described iso-alkyl carbon number is C
3-C
6, described aromatic base is the group that phenyl, naphthyl etc. have aromaticity, described alkylene carbon number is C
2-C
6
The above-mentioned bidentate ligand that contains 2-phenylpyridine structure can for:
The present invention is selected contains amide structure second part, has syntheticly easily, and cost is low, and productive rate high advantage such as just can modify by simple chemical reaction, and the iridium metal complex that synthesizes at room temperature has stronger phosphorescence luminescent properties in the solution.
The used reaction conditions of the present invention only is the stirring under the alkaline condition when room temperature, need compare at nitrogen environment under the high temperature reflux with other same kind compounds, and huge improvement has been arranged.
Phosphor material of the present invention can be used as the functional material in the organic electroluminescence device; Metal iridium complex of the present invention can be connected on the polymer by polymerization.
Description of drawings
Fig. 1 is the crystalline structure figure of a metal-organic complex.
Embodiment
In order more to be expressly understood technical scheme of the present invention, below the present invention is described in further detail.
The preparation method of metal iridium complex of the present invention: be that solvent refluxes and obtains acid amides with acetic acid at first, again with 2-phenylpyridine derivative L by aniline or anils and acid anhydrides or acyl chlorides
2Two endo compound (L
2)
2Ir (μ-Cl)
2Ir (L
2)
2Under alkaline condition, carry out ligand exchange reaction, obtain target product (L
2)
2Ir (ayl).Concrete reaction is as follows:
(1) acid amides is synthetic:
Synthesizing of Acetanilide: with aniline, 4-monomethylaniline, 2,6-xylidine and diacetyl oxide are poured the solution that reaction obtains in the frozen water into after refluxing 4 hours in acetic acid at 1: 2 with mol ratio, separate out solid, suction filtration then, the solid that obtains recrystallization in ethanol can obtain.
Synthesizing of 4-acetobromanilide: with the Acetanilide is raw material, toward wherein dripping excessive slightly bromine, under acetic acid, reflux, reaction obtains the solution cooling, add in the Sulfothiorine and excessive bromine, separate out solid after pouring frozen water then into, then suction filtration, the solid ethyl alcohol recrystallization that obtains gets the 4-acetobromanilide.
When acid amides is p-ayl, be raw material with the methacrylic acid earlier, and SOCl
2In solvent-free reaction down, generate the methacrylic isoxazolecarboxylic acid, being added drop-wise in the new steaming aniline, refluxed 4 hours with the acyl chlorides that obtains, add frozen water, separate out solid, suction filtration, solid ethyl alcohol recrystallization.Its structural formula is:
Synthesizing of (2) two endo compounds
Adopt document (S.Sprouse, K.A.King, P.J.Spellane, and R.J.Watts, J.Am..Chem.Soc.1984,106, two endo compounds (ppy) of the synthetic ppy of method 6647-6653)
2Ir (μ-Cl)
2Ir (ppy)
2Ppy and hydration iridous chloride were refluxed 24 hours under 100 ℃ in mixed solvent water and 2-methyl cellosolve (volume ratio 1: 3), and reaction finishes postcooling, and suction filtration obtains pressed powder.Powder ethanol and washing with acetone.
(3) final product is synthetic
Two endo compounds and acid amides (mol ratio 1: 2.5) are dissolved in the methylene dichloride, add excessive sodium methylate then, stirred 24 hours under the room temperature, drain solvent, the solid that obtains washes with water repeatedly, and thick product crystallization in methylene dichloride/normal hexane mixing solutions obtains final product.
Below be the specific embodiment that the contriver provides, need to prove, the invention is not restricted to these embodiment.
Embodiment 1: assistant ligand is an Acetanilide, and main part is the metal iridium complex (L of 2-phenylpyridine
2)
2Ir's (ayl) is synthetic, and its structural formula is as follows:
(1) preparation of Acetanilide:
In the 100ml round-bottomed flask, add new aniline and the 20ml acetic acid of steaming of 9.3 grams, and then stir Dropwise 5 .1 gram diacetyl oxide down, be heated to 120 degree and reflux, reflux after four hours, stop to reflux.Cooling is poured on reaction soln in the frozen water, separates out a large amount of white solids, suction filtration, and the white solid that obtains is dissolved in crystallization in the 100ml ethanol.Get colourless tabular crystal 10.9 grams (productive rate 81.0%), m.p=125 ℃
(2) two endo compounds (ppy)
2Ir (μ-Cl)
2Ir (ppy)
2Synthetic:
Get 0.568 hydration iridous chloride, 0.725 gram 2-phenylpyridine, join in the mixed solvent of 30 milliliters of cellosolvos and 10 ml waters, being heated to 100 degree under the nitrogen environment refluxed 24 hours, reaction finishes postcooling to room temperature, and suction filtration obtains yellow powder, powder gets product 0.732 gram (productive rate: 66.42%) with dehydrated alcohol and washing with acetone twice.
(3) metal iridium complex (ppy)
2Ir's (ayl) is synthetic:
Get 0.106 gram two endo compounds and 0.040 gram Acetanilide is dissolved in 20 milliliters of methylene dichloride, add 0.050 gram sodium methylate then, stirred 24 hours under the room temperature.After reaction finishes, drain solvent, the pressed powder that obtains deionized water wash 3 times, solid after the vacuum-drying washing, be dissolved in then in the mixed solvent that 10 milliliters of methylene dichloride and 20 milliliters of normal hexanes be made into, freezing and crystallizing, (productive rate: 61.91%), crystalline structure as shown in Figure 1 to get orange crystal 0.078 gram.IR(KBr)：3053m，2961?2926w，16041582s，1544m，1519?1453?1439?1411s，1305?1264?1226?1159?1059?1030?1007?964m，756s，732?697?670m.
1H?MNR(in?CDCl
3)：δ2.17(s，3H，methyl)，6.17(d，2H，phenyl，6.52(d，phenyl，2H)，6.60(t，phenyl，1H)，6.69(t，1H，phenyl，)，6.77(t，1H，phenyl)，6.84(dd，2H，phenyl)，7.02(t，2H，pyridine)，7.17(t，2H，phenyl)，7.52(dd，2H，phenyl)，7.80(t，2H，pyridine)，7.92(d，2H，pyridine)，8.80(d，1H，pyridine)，8.89(d，1H，pyridine).
Embodiment 2: assistant ligand is the 4-acetobromanilide, and main part is metal iridium complex synthetic of 2-phenylpyridine, and its structural formula is as follows:
(1) preparation of 4-acetobromanilide
In 100 milliliters there-necked flask, add 1.530 gram Acetanilides, add 30 milliliters of acetate dissolutions, get 0.8 milliliter of liquid bromine, be dissolved in wiring solution-forming in 10 milliliters of acetic acid, 40 ℃ of bromine acetum temperature controls slowly are added drop-wise in the Acetanilide solution, dripped off in one hour.Be added dropwise to complete the back and keep 40 ℃ of reactions one hour, be warmed up to 60 ℃ then reaction two hours.Cooling is poured on reacted solution in the beaker, adds a small amount of Sulfothiorine to reaction solution and is colourless, then solution is poured in the frozen water, separates out a large amount of white solids.Suction filtration, the white solid that obtains crystallization in ethanol obtains white needle-like crystals 1.502 gram (productive rates: 61.68%).M.P＝169.2℃
(2) two endo compounds (ppy)
2Ir (μ-Cl)
2Ir (ppy)
2Preparation:
The preparation method is with embodiment 1.
(3) metal iridium complex (L
2)
2The preparation of Ir (Br-ayl):
0.106 restrain two endo compounds and 0.045 gram 4-acetobromanilide is dissolved in 20 milliliters of methylene dichloride, add 0.050 gram sodium methylate then, stirred 24 hours under the room temperature.Reaction is drained solvent after finishing, the pressed powder that obtains deionized water wash 3 times, solid after the vacuum-drying washing, be dissolved in then in the mixed solvent that 10 milliliters of methylene dichloride and 20 milliliters of normal hexanes be made into, freezing and crystallizing, orange crystal 0.082 gram (productive rate: 57.34%).IR(KBr)：3053m，2961?2926w，1605?1580s，1544m，151014521437?1411s，1305?1264?1226?1159?1059?1030?1007?964m，756s，732?697?670m.
1HMNR(in?CDCl
3)：δ2.17(s，3H，methyl)，6.16(d，2H，phenyl)，6.41(d，phenyl，2H)，6.60(t，phenyl，1H)，6.74(dd，1H，phenyl)，6.84(dd，2H，phenyl)，7.11(d，2H，pyridine)，7.17(t，2H，phenyl)，7.52(dd，2H，phenyl)，7.80(t，2H，pyridine)，7.94(d，2H，pyridine)，8.78(d，1H，pyridine)，8.94(d，1H，pyridine).
Embodiment 3: assistant ligand is the 4-exalgine, and main part is metal iridium complex synthetic of 2-phenylpyridine, and its structural formula is:
(1) preparation of 4-exalgine:
In the 100ml round-bottomed flask, add 10.7 gram 4-monomethylaniline and 20ml acetic acid, and then stir Dropwise 5 .1 gram diacetyl oxide down, be heated to 120 degree and reflux, reflux after four hours, stop to reflux.Cooling is poured on reaction soln in the frozen water, separates out a large amount of white solids, suction filtration, and the white solid that obtains is dissolved in crystallization in the 100ml ethanol.Get colourless tabular crystal 11.2 grams (productive rate 75.2%), m.p=149 ℃
(2) metal iridium complex (ppy)
2Ir's (Me-ayl) is synthetic:
0.106 restrain two endo compounds and 0.045 gram 4-exalgine is dissolved in 20 milliliters of methylene dichloride, add 0.050 gram sodium methylate then, stirred 24 hours under the room temperature.Reaction is drained solvent after finishing, the pressed powder that obtains deionized water wash 3 times, solid after the vacuum-drying washing, be dissolved in then in the mixed solvent that 10 milliliters of methylene dichloride and 20 milliliters of normal hexanes be made into, freezing and crystallizing, orange crystal 0.077 gram (productive rate: 59.32%).
Embodiment 4: assistant ligand is an Acetanilide, and main part is metal iridium complex synthetic of 2-phenyl (4-chlorine) pyridine, and its structural formula is as follows:
(1) 2-phenyl (4-chlorine) pyridine is synthetic:
Get 2,4-dichloropyridine 5 grams are dissolved in 10 milliliters of tetrahydrofuran (THF)s, phenylo boric acid 6 grams are dissolved in 20 milliliters of tetrahydrofuran (THF)s, nitrogen mixes down in two solution and the 250 milliliters of round-bottomed flasks, add 0.5 gram triphenyl phosphorus then, 0.1 the gram palladium is a catalyzer, adds 10 milliliters of 2mol/L sodium carbonate solutions at last, refluxed under nitrogen 16 hours.Cooling, separatory, water ethyl acetate extraction 3 times, ethyl acetate solution is backed oil phase then, and the solution of gained is washing 3 times with saturated nacl aqueous solution.Dry.Under normal temperature 80 degree, boil off solvent, the residue underpressure distillation that obtains, 0.1mm Hg collects 140 degree cuts down.Get 2-phenyl (4-chlorine) pyridine 4.8 grams.Productive rate: 75.0%
Synthesizing of (2) two endo compounds
Get 0.334 gram hydration iridous chloride, 0.525 gram 2-phenyl (4-chlorine) pyridine, join in the mixed solvent of 30 milliliters of cellosolvos and 10 ml waters, being heated to 100 degree under the nitrogen environment refluxed 24 hours, reaction finishes postcooling to room temperature, and suction filtration obtains yellow powder, powder gets product 0.422 gram (productive rate: 62.24%) with dehydrated alcohol and washing with acetone twice.
(3) metal iridium complex is synthetic
0.120 restrain two endo compounds and 0.040 gram Acetanilide is dissolved in 20 milliliters of methylene dichloride, add 0.050 gram sodium methylate then, stirred under the room temperature 24 hours.Reaction is drained solvent after finishing, the pressed powder that obtains deionized water wash 3 times, solid after the vacuum-drying washing, be dissolved in then in the mixed solvent that 20 milliliters of normal hexanes of 10 milliliters of methylene dichloride lotuses are made into, freezing and crystallizing, orange crystal 0.088 gram (productive rate: 61.11%).
Embodiment 5: assistant ligand is p-ayl, the metal iridium complex of main part position 2-phenylpyridine synthetic, and its structural formula is as follows:
(1) p-ayl's is synthetic
Get 34.1 milliliters of methacrylic acids and down and in phosphorus trichloride and the 100 milliliters of round-bottomed flasks, keep temperature 65-70 degree reaction 12 hours earlier, be warmed up to 80 degree then and kept one hour solvent-free, be cooled to 50 spend about maintenance one hour.Stopped reaction comes down in torrents the upper strata stillness of night, and it is the methacrylic isoxazolecarboxylic acid.In 100 milliliters there-necked flask, load onto 20.1 milliliters of aniline and 43.4 milliliters of triethylamines, get methacrylic isoxazolecarboxylic acid 20.9 grams that obtain above, be added drop-wise in the reaction flask under the normal temperature, dripped off in one hour, be added dropwise to complete the back and reacted 3 hours under 50 degree, stopped reaction adds water washing, use ethyl acetate extraction then, organic layer extracts with dilute hydrochloric acid, is washing with water to neutrality, obtains a large amount of white solids.Ethyl alcohol recrystallization gets white plates crystal 2 5.1 grams, M.P=85 ℃ of productive rate (78.4%)
(2) metal iridium complex is synthetic
0.106 restrain two endo compounds and 0.040 gram p-ayl is dissolved in 20 milliliters of methylene dichloride, add 0.050 gram sodium methylate then, stirred under the room temperature 24 hours.Reaction is drained solvent after finishing, the pressed powder that obtains deionized water wash 3 times, solid after the vacuum-drying washing, be dissolved in then in the mixed solvent that 10 milliliters of methylene dichloride and 20 milliliters of normal hexanes be made into, freezing and crystallizing, orange crystal 0.084 gram (productive rate: 63.63%)
Amides Ir of the present invention (III) a metal-organic complex phosphorescence electroluminescent material can be received on the polymer by polymerization.
Claims (8)
1. amides Ir organometallic complex phosphorescence electroluminescent material, this material is a kind of metal complexes of the 2-of containing phenylpyridine structure, it is characterized in that, this luminescent material has following molecular structural formula:
(L
2)
2Ir(ayl)
In the following formula, L
2Be the bidentate ligand that contains 2-phenylpyridine structure, ayl is the bidentate ligand that contains amide structure.
2. according to the described amides Ir organometallic complex phosphorescence of claim 1 electroluminescent material, it is characterized in that the bidentate ligand ayl structure that contains amide structure is:
R
2Be hydrogen, alkyl, iso-alkyl, aromatic base or alkylene; R
1Be aromatic base or substituted aromatic base.
3. according to the described amides Ir organometallic complex phosphorescence of claim 2 electroluminescent material, it is characterized in that the bidentate ligand ayl that contains amide structure has following structure:
Wherein, R
3Be selected from hydrogen, hydroxyl, alkyl, iso-alkyl, alkoxyl group, halogen atom, aromatic base or alkylene.
4. according to claim 1 or 2 described amides Ir organometallic complex phosphorescence electroluminescent materials, it is characterized in that the bidentate ligand that contains 2-phenylpyridine structure is:
5. amides Ir organometallic complex phosphorescence electroluminescent material according to claim 1 and 2 is characterized in that this luminescent material has following molecular structural formula:
6. the preparation method of the described amides Ir organometallic complex of claim 1, it is characterized in that: amides Ir organometallic complex is with two endo compound (L
2)
2Ir (μ-Cl)
2Ir (L
2)
2React under alkaline condition with acid amides and to obtain L
2It is the bidentate ligand that contains 2-phenylpyridine structure.
7. according to the preparation method of the described amides Ir organometallic complex of claim 6, it is characterized in that: two endo compounds and acid amides react in methylene dichloride in the presence of sodium alkoxide.
8. the application of the described amides Ir organometallic complex of claim 1 in making organic electroluminescence device.
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| CN103896990B (en) * | 2014-03-12 | 2017-02-08 | 石家庄诚志永华显示材料有限公司 | organic electroluminescent material and application thereof |
| CN107207959A (en) * | 2015-02-18 | 2017-09-26 | 剑桥显示技术有限公司 | Organic luminescence polymer in the polymer backbone comprising luminous repeat unit and the device with it |
| CN107207959B (en) * | 2015-02-18 | 2023-04-18 | 剑桥显示技术有限公司 | Organic light emitting polymer including light emitting repeating unit in polymer main chain and device having the same |
| CN110872329A (en) * | 2019-11-01 | 2020-03-10 | 深圳大学 | Iridium complex and preparation method and application thereof |
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