CN103804276A - Bipolar red phosphorescent compound, preparation method thereof and organic electroluminescent device - Google Patents

Bipolar red phosphorescent compound, preparation method thereof and organic electroluminescent device Download PDF

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CN103804276A
CN103804276A CN201210443988.XA CN201210443988A CN103804276A CN 103804276 A CN103804276 A CN 103804276A CN 201210443988 A CN201210443988 A CN 201210443988A CN 103804276 A CN103804276 A CN 103804276A
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phosphorescent compound
preparation
compound
ruddiness phosphorescent
bipolarity ruddiness
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周明杰
王平
张振华
黄辉
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a bipolar red phosphorescent compound, a preparation method thereof and an organic electroluminescent device. The compound has a structural formula shown in the specification. The bipolar red phosphorescent compound has hole transport and electron transmission properties, so the hole and electron transfer balance in a luminous layer is realized, thereby the luminous efficiency of the compound can be substantially improved.

Description

Bipolarity ruddiness phosphorescent compound, its preparation method and organic electroluminescence device
Technical field
The present invention relates to organic semiconductor material, relate in particular to a kind of bipolarity ruddiness phosphorescent compound and preparation method thereof.The invention still further relates to and use the organic electroluminescence device of this bipolarity ruddiness phosphorescent compound as luminescent layer material of main part.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide and can be finely tuned and be changed luminescent properties and make rich color by chemical structure, easily realize the advantages such as resolving power is high, lightweight, large-area flat-plate demonstration, be described as " 21 century flat panel display ", become the focus of the subjects such as material, information, physics and flat pannel display area research.Following commercialization Organic Light Emitting Diode efficiently will contain organo-metallic phosphorescent substance possibly, because they can all catch singlet and triplet excitons, thereby realize 100% internal quantum efficiency.But, because the excited state exciton life-span of transition metal complex is relatively long, cause triplet state-triplet state (T 1-T 1) cancellation in device real work.In order to overcome this problem, investigators are often doped to triplet state shiner in organic main body material.Therefore,, for efficient Organic Light Emitting Diode, develop high performance material of main part and guest materials most important.As one of three primary colours, ruddiness is very crucial for panchromatic colour developing and solid-state illumination.But red phosphorescent device is little efficiently, major cause is to lack suitable material of main part.
At present, the material of main part that is widely used in red phosphorescent device is CBP(4,4 '-bis-(9-carbazyl) biphenyl), but the driving voltage that it requires is higher, second-order transition temperature (T g) low (T g=62 ℃), be easy to crystallization.In addition, CBP is a kind of p-shaped material, and hole mobility, far above electronic mobility, be unfavorable for carrier injection and transmission balance, and luminous efficiency is low.
Summary of the invention
One of problem to be solved by this invention is to provide a kind of bipolarity ruddiness phosphorescent compound of the luminous efficiency that can improve organic electroluminescence device.
Two of problem to be solved by this invention is to provide the preparation method of above-mentioned bipolarity ruddiness phosphorescent compound.
Three of problem to be solved by this invention is to provide the organic electroluminescence device of the above-mentioned bipolarity ruddiness phosphorescent compound of use as luminescent layer material of main part.
Technical scheme of the present invention is as follows:
A kind of bipolarity ruddiness phosphorescent compound, it has following structural formula:
Figure BDA00002375110400021
The preparation method of above-mentioned bipolarity ruddiness phosphorescent compound, comprises the steps:
S1, under oxygen-free environment, by structural formula be
Figure BDA00002375110400022
compd A dissolve in organic solvent, in organic solvent, add structural formula to be again subsequently
Figure BDA00002375110400023
compd B, then in organic solvent, add mineral alkali and catalyzer again, at 70～120 ℃, react 6～15 hours, stopped reaction cool to room temperature, obtain structural formula and be compound C; Wherein, the mol ratio of compd A and compd B is 1:2～1:2.4;
At S2,0 ℃, Compound C is dissolved in methylene dichloride, obtains mixed solution, again mixed solution is splashed into subsequently in the dichloromethane solution of m-chloro-benzoic acid, after dropwising, at room temperature react 12 hours, then add saturated NaHCO 3and stir 30 minutes, obtain structural formula and be bipolarity ruddiness phosphorescent compound.
In the preparation method's of above-mentioned bipolarity ruddiness phosphorescent compound step S1:
It is at least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF that described organic solvent is selected from solvent;
Described mineral alkali is selected from least one in sodium carbonate, salt of wormwood, cesium carbonate and potassiumphosphate; The mol ratio of described mineral alkali and described compd A is 2:1～2.5:1;
Described catalyzer is copper powder, cuprous iodide or Red copper oxide; The mol ratio of described catalyzer and described compd A is 1:10 ~ 1:5.
The preparation method of described bipolarity ruddiness phosphorescent compound, as preferred version, in step S1, after reaction stops, also comprising the purification process to Compound C:
After stopped reaction, by reacting liquid filtering, with after washing screening, be then drip washing screening with normal hexane, leacheate separates through silica gel column chromatography again, obtains the Compound C of purifying.
The preparation method of described bipolarity ruddiness phosphorescent compound, as preferred version, in step S2, after reaction stops, also comprising the purification process to bipolarity ruddiness phosphorescent compound:
After reaction stops, the organic phase in reaction solution is separated, and anhydrous magnesium sulfate drying organic phase, adopting subsequently volume ratio is the organic phase that the toluene of 5:1 and the mixed solvent recrystallization of ethanol composition were dried, and obtains the bipolarity ruddiness phosphorescent compound of purifying.
A kind of organic electroluminescence device, the material of its luminescent layer is three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) is doped to the doping mixing material forming in material of main part according to 15% mass ratio, and described material of main part is the bipolarity ruddiness phosphorescent compound with following structural formula:
Bipolarity ruddiness phosphorescent compound provided by the invention has hole transport character and electronic transport property simultaneously, makes the transmission balance of its hole and electronics in luminescent layer, greatly improves its luminous efficiency; Meanwhile, this compound has higher triplet, can effectively prevent that in luminescence process, energy returns to material of main part, thereby has also improved its luminous efficiency.
The preparation method of the bipolarity ruddiness phosphorescent compound that invention provides, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity ruddiness phosphorescent compound that makes of the present invention;
Fig. 2 is the structural representation of the organic electroluminescence device that makes of embodiment 6.
Embodiment
A kind of bipolarity ruddiness phosphorescent compound provided by the invention, it has following structural formula:
Figure BDA00002375110400042
This bipolarity ruddiness phosphorescent compound has hole transport character and electronic transport property simultaneously, makes the transmission balance of its hole and electronics in luminescent layer, greatly improves its luminous efficiency; Meanwhile, this compound has higher triplet, can effectively prevent that in luminescence process, energy returns to material of main part, thereby has also improved its luminous efficiency.
Fig. 1 is the thermogravimetic analysis (TGA) figure of bipolarity ruddiness phosphorescent compound; Thermogravimetic analysis (TGA) is completed by Perkin-Elmer Series 7 Thermo System measurements, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, the thermal weight loss temperature (T of this compound 5% d) be 396 ℃.
The preparation method of above-mentioned bipolarity ruddiness phosphorescent compound, comprises the steps:
S1, under oxygen-free environment (by nitrogen, argon gas, or the gas mixture of nitrogen and argon gas composition), by structural formula be
Figure BDA00002375110400051
compd A (3, the iodo-9-phenyl-9H-of 6-bis-carbazole) dissolve in organic solvent, in organic solvent, add structural formula to be again subsequently
Figure BDA00002375110400052
compd B (being thiophenol), then in organic solvent, add mineral alkali and catalyzer again, at 70～120 ℃, react 6～15 hours, stopped reaction cool to room temperature, obtain structural formula and be
Figure BDA00002375110400053
compound C (, 9-phenyl-3,6-bis-(thiophenyl)-9H-carbazole); Wherein, the mol ratio of compd A and compd B is 1:2～1:2.4; Reaction formula is as follows:
At S2,0 ℃, Compound C is dissolved in methylene dichloride, obtains mixed solution, again mixed solution is splashed into subsequently m-chloro-benzoic acid (mCPBA) (structural formula is: ) methylene dichloride (DCM) solution in, after dropwising, at room temperature react 12 hours, then add saturated NaHCO 3and stir 30 minutes, obtain structural formula and be
Figure BDA00002375110400061
bipolarity ruddiness phosphorescent compound (being 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole); Reaction formula is as follows:
Figure BDA00002375110400062
In the preparation method's of above-mentioned bipolarity ruddiness phosphorescent compound step S1:
It is at least one in tetrahydrofuran (THF) (THF), acetonitrile (MeCN), toluene (Tol) and DMF (DMF) that described organic solvent is selected from solvent;
Described mineral alkali is selected from sodium carbonate (Na 2cO 3), salt of wormwood (K 2cO 3), cesium carbonate (Cs 2cO 3) and potassiumphosphate (K 3pO 4) at least one; The mol ratio of described mineral alkali and described compd A is 2:1～2.5:1;
Described catalyzer is copper (Cu) powder, cuprous iodide (CuI) or Red copper oxide (Cu 2o); The mol ratio of described catalyzer and described compd A is 1:10 ~ 1:5.
The preparation method of described bipolarity ruddiness phosphorescent compound, as preferred version, in step S1, after reaction stops, also comprising the purification process to Compound C:
After stopped reaction, by reacting liquid filtering, with after washing screening, be then drip washing screening with normal hexane, leacheate separates through silica gel column chromatography again, obtains the Compound C of purifying.
The preparation method of described bipolarity ruddiness phosphorescent compound, as preferred version, in step S2, after reaction stops, also comprising the purification process to bipolarity ruddiness phosphorescent compound:
After reaction stops, the organic phase in reaction solution is separated, and anhydrous magnesium sulfate drying organic phase, adopting subsequently volume ratio is the organic phase that the toluene of 5:1 and the mixed solvent recrystallization of ethanol composition were dried, and obtains the bipolarity ruddiness phosphorescent compound of purifying.
The preparation method of bipolarity ruddiness phosphorescent compound provided by the invention, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
A kind of organic electroluminescence device, its structure comprises the glass, conductive anode layer, hole injection layer, hole transport/electronic barrier layer (middle brace "/" represents to have hole transport function and electronic blocking function), luminescent layer, electric transmission/hole blocking layer (middle brace "/" represents to have electric transmission function and hole barrier function), electron injecting layer and the cathode layer that stack gradually; Wherein:
The material of conductive anode layer is tin indium oxide compound (ITO);
The material of hole injection layer is for gathering (3,4-Ethylenedioxy Thiophene) (PEDOT) and the matrix material (being expressed as PEDOT:PSS) of polystyrolsulfon acid (PSS);
The material of hole transport/electronic barrier layer is N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4,4'-diamines (TPD);
The material of luminescent layer is three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) (Ir (piq) 3) being doped to the doping mixing material forming in material of main part according to 15% mass ratio, described material of main part is the bipolarity ruddiness phosphorescent compound with following structural formula (representing with P):
Figure BDA00002375110400071
this doping mixing material is expressed as P:Ir (piq) 3;
The material of electric transmission/hole blocking layer is 4,7-phenylbenzene-1,10-phenanthroline (BPhen);
The material of electron injecting layer is LiF;
The material of cathode layer is Al.
The structure of this organic electroluminescence device is: glass/ITO/PEDOT:PSS/TPD/P:Ir (piq) 3/ BPhen/LiF/Al.
In order to understand better the content of patent of the present invention, further illustrate technology case of the present invention below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein compd A, compd B are all bought and are obtained from the market.
Embodiment 1
The bipolarity ruddiness phosphorescent compound of the present embodiment, for: 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole, structural formula is as follows:
Figure BDA00002375110400081
The preparation technology of this compound is as follows:
The preparation of the first step, Compound C
Figure BDA00002375110400082
Under nitrogen protection; by 3; the iodo-9-phenyl-9H-carbazole of 6-bis-(39.6g, 80mmol) is dissolved in 200mLN, in dinethylformamide (DMF) solution; then add thiophenol (44.0g; 160mmol), salt of wormwood (22.1g, 160mmol); cuprous iodide (1.52g, 8mmol).Mixture stirring reaction 6 hours at 120 ℃.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid Compound C through silica gel column chromatography.Productive rate is 94%.
Second step, 9-phenyl-3, the preparation of 6-bis-(phenyl sulfonyl)-9H-carbazole
Figure BDA00002375110400083
Under 0 ℃ of bath, Compound C (18.4g, 40mmol) is dissolved in methylene dichloride (DCM) solution of 120mL, is then splashed in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).At room temperature stirring reaction after 12 hours of mixture, then add 300mL saturated sodium bicarbonate solution to stir 30 minutes.Separate organic layer, anhydrous magnesium sulfate drying.Crude product adopts solvent toluene/ethanol (5:1) recrystallization to obtain white solid product 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole.Productive rate 83%.
Mass spectrum: m/z 523.1(M ++ 1); Ultimate analysis (%) C 30h 21nO 4s 2: theoretical value C 68.81, H 4.04, N 2.67, O 12.22, S 12.25; Measured value: C 68.79, H 4.10, N 2.68, O 12.17, S 12.29.
Embodiment 2
The bipolarity ruddiness phosphorescent compound of the present embodiment, for: 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole, structural formula is as follows:
Figure BDA00002375110400091
The preparation technology of this compound is as follows:
The preparation of the first step, Compound C
Figure BDA00002375110400092
Under argon shield, iodo-3,6-bis-9-phenyl-9H-carbazole (39.6g, 80mmol) is dissolved in 200mL toluene (Tol) solution; then add thiophenol (48.4g, 176mmol), cesium carbonate (57.2g; 176mmol), copper powder (0.768g, 12mmol).Mixture stirring reaction 9 hours at 110 ℃.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid Compound C through silica gel column chromatography.Productive rate is 95%.
Second step, 9-phenyl-3, the preparation of 6-bis-(phenyl sulfonyl)-9H-carbazole
This step is identical with the second step in embodiment 1.
Embodiment 3
The bipolarity ruddiness phosphorescent compound of the present embodiment, for: 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole, structural formula is as follows:
Figure BDA00002375110400101
The preparation technology of this compound is as follows:
The preparation of the first step, Compound C
Figure BDA00002375110400102
Under nitrogen and the protection of argon gas gas mixture; by 3; the iodo-9-phenyl-9H-of 6-bis-carbazole (39.6g; 80mmol) be dissolved in 200mL acetonitrile (MeCN) solution, then add thiophenol (52.8g, 192mmol); potassiumphosphate (39g; 184mmol), Red copper oxide (2.3g, 16mmol).Mixture stirring reaction 12 hours at 90 ℃.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid Compound C through silica gel column chromatography.Productive rate is 87%.
Second step, 9-phenyl-3, the preparation of 6-bis-(phenyl sulfonyl)-9H-carbazole
This step is identical with the second step in embodiment 1.
Embodiment 4
The bipolarity ruddiness phosphorescent light body material of the present embodiment, its structure is: 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole, structural formula is as follows:
Figure BDA00002375110400111
The preparation technology of this compound is as follows:
The preparation of the first step, Compound C
Figure BDA00002375110400112
Under nitrogen protection; by 3; the iodo-9-phenyl-9H-of 6-bis-carbazole (39.6g; 80mmol) be dissolved in 200mL tetrahydrofuran (THF) (THF) solution, then add thiophenol (50.6g, 184mmol); sodium carbonate (20.4g; 192mmol), cuprous iodide (2.6g, 13.6mmol).Mixture stirring reaction 15 hours at 70 ℃.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid Compound C through silica gel column chromatography.Productive rate is 91%.
Second step, 9-phenyl-3, the preparation of 6-bis-(phenyl sulfonyl)-9H-carbazole
This step is identical with the second step in embodiment 1.
Embodiment 5
The bipolarity ruddiness phosphorescent light body material of the present embodiment, its structure is: 9-phenyl-3,6-bis-(phenyl sulfonyl)-9H-carbazole, structural formula is as follows:
Figure BDA00002375110400113
The preparation technology of this compound is as follows:
The preparation of the first step, Compound C
Figure BDA00002375110400121
Under nitrogen protection; by 3; the iodo-9-phenyl-9H-carbazole of 6-bis-(39.6g, 80mmol) is dissolved in 200mLN, in dinethylformamide (DMF) solution; then add thiophenol (46.2g; 168mmol), potassiumphosphate (42.4g, 200mmol); copper powder (1g, 16mmol).Mixture stirring reaction 15 hours at 100 ℃.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid Compound C through silica gel column chromatography.Productive rate is 86%.
Second step, 9-phenyl-3, the preparation of 6-bis-(phenyl sulfonyl)-9H-carbazole
This step is identical with the second step in embodiment 1.
Embodiment 6:
The present invention is organic electroluminescence device, and its structure comprises the glass, conductive anode layer, hole injection layer, hole transport/electronic barrier layer, luminescent layer, electric transmission/hole blocking layer, electron injecting layer and the cathode layer that stack gradually; Wherein:
The material of conductive anode layer is tin indium oxide compound (ITO), and thickness is 150nm;
The material of hole injection layer for poly-(3,4-Ethylenedioxy Thiophene) (PEDOT) with polystyrolsulfon acid PSS) matrix material (being expressed as PEDOT:PSS), thickness is 30nm;
The material of hole transport/electronic barrier layer is N, N'-phenylbenzene-N, and N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4,4'-diamines (TPD), thickness is 20nm;
The material of luminescent layer is three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) (Ir (piq) 3) being doped to 9-phenyl-3 according to 15% mass ratio, in 6-bis-(phenyl sulfonyl)-9H-carbazole (representing with P), the doping mixing material of composition, is expressed as P:Ir (piq) 3, thickness is 20nm;
The material of electric transmission/hole blocking layer is 4,7-phenylbenzene-1,10-phenanthroline (BPhen), and thickness is 30nm;
The material of electron injecting layer is LiF, and thickness is 1nm;
The material of cathode layer is Al, and thickness is 100nm.
As shown in Figure 2, the structure of this organic electroluminescence device is: glass/ITO/PEDOT:PSS/TPD/P:Ir (piq) 3/ BPhen/LiF/Al.
The preparation technology of above-mentioned organic electroluminescence device is as follows:
First, use successively liquid detergent, deionized water, acetone, ethanol, the each ultrasonic cleaning 15min of Virahol, remove the organic pollutant on ito glass surface,
Secondly,, at ITO surface spin coating hole injection layer, material is PEDOT:PSS;
Then, stack gradually evaporation hole transmission layer/electronic barrier layer (material is TPD) on hole injection layer surface, (material is Ir (piq) to luminescent layer 3be doped to 9-phenyl-3 according to 15% mass ratio, in 6-bis-(phenyl sulfonyl)-9H-carbazole (representing with P), the doping mixing material of composition, is expressed as P:Ir (piq) 3), electron transfer layer/hole blocking layer (material is BPhen), electron injecting layer (material is LiF) and cathode layer (material is Al).
Electric current-the brightness-voltage characteristic of organic electroluminescence device is to be completed by the Keithley source measuring system with correction silicon photoelectric diode (Keithley 2400Sourcemeter, Keithley 2000Cuirrentmeter).
Test result is that the trigger voltage of organic electroluminescence device is 2.5V, at 1000cd/m 2brightness under, luminous efficiency is 15.8lm/W.
Should be understood that, the above-mentioned statement for preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, and scope of patent protection of the present invention should be as the criterion with claims.

Claims (8)

1. a bipolarity ruddiness phosphorescent compound, is characterized in that, this compound has following structural formula:
Figure FDA00002375110300011
2. a preparation method for bipolarity ruddiness phosphorescent compound, is characterized in that, comprises the steps:
S1, under oxygen-free environment, by structural formula be
Figure FDA00002375110300012
compd A dissolve in organic solvent, in organic solvent, add structural formula to be again subsequently
Figure FDA00002375110300013
compd B, then in organic solvent, add mineral alkali and catalyzer again, at 70～120 ℃, react 6～15 hours, stopped reaction cool to room temperature, obtain structural formula and be
Figure FDA00002375110300014
compound C; Wherein, the mol ratio of compd A and compd B is 1:2～1:2.4;
At S2,0 ℃, Compound C is dissolved in methylene dichloride, obtains mixed solution, again mixed solution is splashed into subsequently in the dichloromethane solution of m-chloro-benzoic acid, after dropwising, at room temperature react 12 hours, then add saturated NaHCO 3and stir 30 minutes, obtain structural formula and be
Figure FDA00002375110300021
bipolarity ruddiness phosphorescent compound.
3. the preparation method of bipolarity ruddiness phosphorescent compound according to claim 2, is characterized in that, in step S1, it is at least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF that described organic solvent is selected from solvent.
4. the preparation method of bipolarity ruddiness phosphorescent compound according to claim 2, is characterized in that, in step S1, described mineral alkali is selected from least one in sodium carbonate, salt of wormwood, cesium carbonate and potassiumphosphate; The mol ratio of described mineral alkali and described compd A is 2:1～2.5:1.
5. the preparation method of bipolarity ruddiness phosphorescent compound according to claim 2, is characterized in that, in step S1, described catalyzer is copper powder, cuprous iodide or Red copper oxide; The mol ratio of described catalyzer and described compd A is 1:10 ~ 1:5.
6. the preparation method of bipolarity ruddiness phosphorescent compound according to claim 2, is characterized in that, in step S 1, after reaction stops, also comprising the purification process to Compound C:
After stopped reaction, by reacting liquid filtering, with after washing screening, be then drip washing screening with normal hexane, leacheate separates through silica gel column chromatography again, obtains the Compound C of purifying.
7. the preparation method of bipolarity ruddiness phosphorescent compound according to claim 6, is characterized in that, in step S2, after reaction stops, also comprising the purification process to bipolarity ruddiness phosphorescent compound:
After reaction stops, the organic phase in reaction solution is separated, and anhydrous magnesium sulfate drying organic phase, adopting subsequently volume ratio is the organic phase that the toluene of 5:1 and the mixed solvent recrystallization of ethanol composition were dried, and obtains the bipolarity ruddiness phosphorescent compound of purifying.
8. an organic electroluminescence device, the material of its luminescent layer is three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) is doped to the doping mixing material forming in material of main part according to 15% mass ratio, it is characterized in that, described material of main part is the bipolarity ruddiness phosphorescent compound with following structural formula:
Figure FDA00002375110300031
CN201210443988.XA 2012-11-08 2012-11-08 Bipolar red phosphorescent compound, preparation method thereof and organic electroluminescent device Pending CN103804276A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109748908A (en) * 2017-11-02 2019-05-14 广东阿格蕾雅光电材料有限公司 Bipolar host material and application based on 4,6- diphenyl sulphone (DPS) dibenzofurans
CN112321567A (en) * 2020-10-22 2021-02-05 安徽科技学院 Multi-stimulus response type material and preparation method and application thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109748908A (en) * 2017-11-02 2019-05-14 广东阿格蕾雅光电材料有限公司 Bipolar host material and application based on 4,6- diphenyl sulphone (DPS) dibenzofurans
CN109748908B (en) * 2017-11-02 2021-07-16 广东阿格蕾雅光电材料有限公司 Bipolar host material based on 4, 6-diphenyl sulfone dibenzofuran and application
CN112321567A (en) * 2020-10-22 2021-02-05 安徽科技学院 Multi-stimulus response type material and preparation method and application thereof
CN112321567B (en) * 2020-10-22 2023-01-13 安徽科技学院 Multi-stimulus response type material and preparation method and application thereof

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Application publication date: 20140521