CN103804360A - Bipolar blue phosphorescent compound, and preparation method and application thereof - Google Patents
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- CN103804360A CN103804360A CN201210444207.9A CN201210444207A CN103804360A CN 103804360 A CN103804360 A CN 103804360A CN 201210444207 A CN201210444207 A CN 201210444207A CN 103804360 A CN103804360 A CN 103804360A
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- UBASCOPZFCGGAV-UHFFFAOYSA-N CC1(C)OB(c(cc2c3ccccc33)ccc2[n]3-c2ccccc2)OC1(C)C Chemical compound CC1(C)OB(c(cc2c3ccccc33)ccc2[n]3-c2ccccc2)OC1(C)C UBASCOPZFCGGAV-UHFFFAOYSA-N 0.000 description 1
- LWEOIBODAFUVEF-UHFFFAOYSA-N c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c1cc(-c2nc3ccccc3[n]2-c2ccccc2)ccc1 Chemical compound c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1ccc2-c1cc(-c2nc3ccccc3[n]2-c2ccccc2)ccc1 LWEOIBODAFUVEF-UHFFFAOYSA-N 0.000 description 1
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- 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 blue phosphorescent compound, and a preparation method and an application thereof. The compound has a structural formula shown in the specification. The bipolar blue phosphorescent compound simultaneously has hole transport and electron transmission properties, so the hole and electron transfer balance in the luminous layer of an organic electroluminescent device is realized, thereby the luminous efficiency of the device can be substantially improved; and the compound has a high triplet energy level, so the return of energy to a host material in a luminescence process can be effectively prevented, thereby the luminous efficiency can also be improved.
Description
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of bipolarity blue emitting phosphor compound and its preparation method and application.
Background technology
Recent two decades comes, and organic electroluminescence device (OLED), because having efficient, low voltage drive, is easy to the advantages such as big area preparation and panchromatic demonstration and has broad application prospects, and has obtained people's extensive concern.The research of organic light emission starts from eighties of last century sixties, until the Tang of Kodak in 1987 etc. adopt sandwich device architecture in patent US4356429Z, the OLDE device of developing luminosity under 10V direct voltage drive reaches 1000cd/m
2, make OLED obtain epoch-making development.
Organic electroluminescent is mainly divided into fluorescence and phosphorescence, but according to spin quantum statistical theory, singlet state exciton and triple probability of state are 1:3, are 25% from the theoretical limit of the fluorescence of singlet state exciton radiative transition, and the theoretical limit of the fluorescence of triplet exciton radiative transition is 75%.How to utilize the energy of 75% triplet excitons to be called the task of top priority.1998, phosphorescent coloring octaethylporphyrin platinum (PtOEP) is entrained in Alq by Forrest group of Princeton university of the U.S.
3middle as electroluminescent material, the external quantum efficiency of device is brought up to 4%.Meanwhile, the people such as professor Ma Yuguang of Jilin University of China adopts double-core metal complexes [Au
2(dppm) Cl
2] be ITO/Au as luminescent layer making structure
2(dppm) Cl
2the individual layer El element of/Al, has also observed the transmitting from triplet state.The frontier of electrophosphorescence has been opened up in these researchs.From then on, people have carried out a large amount of research to phosphor material.
The device that organic light emission is conventional is host-guest system structure, and the triplet that the material of main part of phosphor material is had relatively high expectations, to prevent the revolution of guest materials energy.Conventional phosphorescent light body material is mainly containing carbazoles material, and because it has higher triplet, but carbazole only has good hole transport character, does not possess electronic transport property.Carbazoles as the main recombination region, electron hole of material of main part device near electron transfer layer and luminescent layer interface, if material of main part possesses good hole and electron transport ability simultaneously, the luminous efficiency of device, at the luminescent layer of whole organic electroluminescence device, is improved greatly in recombination region.
Summary of the invention
The bipolarity blue emitting phosphor compound that provides a kind of luminous efficiency higher is provided problem to be solved by this invention.
Technical scheme of the present invention is as follows:
A kind of bipolarity blue emitting phosphor compound, has following structural formula:
The preparation method of this bipolarity blue emitting phosphor compound, comprises the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
b be added into and contain in the organic solvent that catalyzer and alkaline solution exist, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, obtain structural formula and be after separating-purifying
bipolarity blue emitting phosphor compound; Wherein, the mol ratio of compd A and compd B is 1:1～1.2.
The preparation method of described bipolarity blue emitting phosphor compound, wherein, described catalyzer is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, the mol ratio palladium that is 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
The preparation method of described bipolarity blue emitting phosphor compound, wherein, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
The preparation method of described bipolarity blue emitting phosphor compound, wherein, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
The preparation method of described bipolarity blue emitting phosphor compound, wherein, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, the reaction times is 24～36 hours.
The preparation method of described bipolarity blue emitting phosphor compound, wherein, the separating-purifying of described bipolarity blue emitting phosphor compound comprises the steps:
After Suzuki coupling reaction finishes, with dichloromethane extraction reaction solution repeatedly, then merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, it is that leacheate separates and obtains crystalline substance through silica gel column chromatography with the mixed solution of ethyl acetate that crude product adopts the sherwood oil that volume ratio is 10:1, subsequently crystalline substance after 50 ℃ of dry 24h, is obtained to described bipolarity blue emitting phosphor compound under vacuum.
Above-mentioned bipolarity blue emitting phosphor compound in organic electroluminescence device as the application of the material of main part of luminescent layer.
Bipolarity blue emitting phosphor compound of the present invention, has hole transport character and electronic transport property, makes hole in its organic electroluminescence device luminescent layer and the transmission balance of electronics, greatly improves luminous efficiency; Meanwhile, it has higher triplet, effectively prevents that in luminescence process, energy returns to material of main part, and this also can improve its luminous efficiency.In addition, this compound also has good thermostability.
The preparation technology of bipolarity blue emitting phosphor compound provided by the invention, has adopted better simply synthetic route, and synthetic method is simple, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced, and is suitable for widespread use.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of bipolarity blue emitting phosphor compound of the present invention;
Fig. 2 is the structural representation of the organic electroluminescence device of embodiment 5.
Embodiment
Bipolarity blue emitting phosphor compound provided by the invention, its structure suc as formula shown in:
This bipolarity blue emitting phosphor compound, has hole transport character and electronic transport property, makes hole in its organic electroluminescence device luminescent layer and the transmission balance of electronics, greatly improves luminous efficiency; Meanwhile, it has higher triplet, effectively prevents that in luminescence process, energy returns to material of main part, and this also can improve its luminous efficiency.In addition, this compound also has good thermostability.
Fig. 1 is the thermogravimetic analysis (TGA) figure of bipolarity blue emitting phosphor compound of the present invention; 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 1,5% thermal weight loss temperature (T
d) be 405 ℃.
The preparation method of above-mentioned bipolarity blue emitting phosphor compound, comprises the steps:
S1, respectively provide following structural formula to represent compd A and B,
S2, under oxygen-free environment (nitrogen, argon gas or nitrogen and argon gas gas mixture form), compd A and B are added in the organic solvent that contains catalyzer and alkaline solution existence, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, separating-purifying obtains structural formula and is
bipolarity blue light phosphorus compound; Wherein, the mol ratio of compd A and compd B is 1:1～1.2; Reaction formula is as follows:
In the preparation method of above-mentioned bipolarity blue light phosphorus compound, in step S2:
Preferably, described catalyzer is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, the mol ratio palladium that is 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
Preferably, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
Preferably, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
Preferably, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～36 hours.
Preferably, the separating-purifying of described bipolarity blue emitting phosphor compound comprises the steps:
After Suzuki coupling reaction finishes, with dichloromethane extraction reaction solution repeatedly, then merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, it is that leacheate separates and obtains crystalline substance through silica gel column chromatography with the mixed solution of ethyl acetate that crude product adopts the sherwood oil that volume ratio is 10:1, subsequently crystalline substance after 50 ℃ of dry 24h, is obtained to described bipolarity blue emitting phosphor compound under vacuum.
Above-mentioned bipolarity blue emitting phosphor compound in organic electroluminescence device as the application of the material of main part of luminescent layer.
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
Embodiment 1
The bipolarity blue emitting phosphor compound of the present embodiment, i.e. 9-phenyl-3-(3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole, preparation process is as follows:
Under argon shield, by 9-phenyl-3-tetramethyl ethylene ketone boric acid ester-9H-carbazole (74mg, 0.2mmol), 2-(3-bromophenyl)-1-phenyl-1H-benzoglyoxaline (70mg, 0.2mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 ℃ and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 ℃ of dry 24h of vacuum.Productive rate is 82%.Mass spectrum: m/z 511.2 (M
++ 1); Ultimate analysis (%) C
37h
25n
3: theoretical value C 86.86, H 4.93, N 8.21; Measured value: C 86.71, H 4.90, N 8.25.
Embodiment 2
The bipolarity blue emitting phosphor compound of the present embodiment, i.e. 9-phenyl-3-(3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole, preparation process is as follows:
Under nitrogen and the protection of argon gas gas mixture; by 9-phenyl-3-tetramethyl ethylene ketone boric acid ester-9H-carbazole (111mg; 0.3mmol), 2-(3-bromophenyl)-1-phenyl-1H-benzoglyoxaline (115mg; 0.33mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein; after fully dissolving, add again sodium bicarbonate (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 ℃ and carry out Suzuki coupling reaction 48h again.Stopped reaction cool to room temperature, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 ℃ of dry 24h of vacuum.Productive rate is 88%.
Embodiment 3
The bipolarity blue emitting phosphor compound of the present embodiment, i.e. 9-phenyl-3-(3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole, preparation process is as follows:
Under nitrogen protection, by 9-phenyl-3-tetramethyl ethylene ketone boric acid ester-9H-carbazole (111mg, 0.3mmol), 2-(3-bromophenyl)-1-phenyl-1H-benzoglyoxaline (126mg, 0.36mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution leads to after the about 30min of nitrogen purge gas subsequently in flask; Flask is heated to 130 ℃ and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 ℃ of dry 24h of vacuum.Productive rate is 80%.
Embodiment 4
The bipolarity blue emitting phosphor compound of the present embodiment, i.e. 9-phenyl-3-(3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole, preparation process is as follows:
Embodiment 5
The present embodiment is organic electroluminescence device, and it adopts the material of main part of the arbitrary 9-phenyl-3-making of above-described embodiment 1 to 5 (3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole (representing with P) as luminescent layer.
This organic electroluminescence device, as shown in Figure 2, comprises substrate 1/ conductive anode layer 2/ hole injection layer 3/ hole transmission layer 4/ luminescent layer 5/ electron transfer layer 6/ electron injecting layer 7 cathode layers 8.
Functional layer material and the thickness of above-mentioned organic electroluminescence device are as follows:
Substrate 1 adopts glass;
Conductive anode layer 2 adopts ITO (tin indium oxide compound), thickness 150nm; ITO is prepared after glass surface, is called for short ito glass;
The material of hole injection layer 3, for poly-(3,4-Ethylenedioxy Thiophene) (being called for short PEDOT) and the polystyrolsulfon acid matrix material of (being called for short PSS), is expressed as PEDOE:PSS, and thickness is 30nm;
The material of hole transmission layer 4 is N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1, and 1 '-xenyl-4,4 '-diamines (NPD), thickness is 20nm;
The material of luminescent layer 5 is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (FIrpic) as object luminescent material, be doped to the doping mixing material obtaining in 9-phenyl-3-(3-(1-phenyl-1H-benzimidazolyl-2 radicals-yl) phenyl)-9H-carbazole (representing with P) material of main part according to 12% mass ratio, be expressed as P:FIrpic, thickness is 20nm;
The material of electron transfer layer 6 is oxine aluminium (Alq
3), thickness is 30nm;
The material of electron injecting layer 7 is lithium fluoride (LiF), and thickness is 1nm;
The material of cathode layer 8 is aluminium (Al), and thickness is 100nm.
Above-mentioned organic electroluminescence device can be expressed as:
Glass/ITO/PEDOE:PSS/NPD/P:FIrpic/Alq
3/ LiF/Al.
This organic electroluminescence device, its preparation technology is as follows:
First, prepare one deck ITO layer at the glass surface cleaning up by magnetron sputtering, obtain ito glass;
Secondly, ito glass is moved in vacuum evaporation equipment, stack gradually PEDOE:PSS, NPD, P:FIrpic, Alq on ITO layer surface
3, LiF, Al;
After above-mentioned processing step completes, obtain organic electroluminescence device.
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 3.2V, at 1000cd/m
2brightness under, luminous efficiency is 17.0lm/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 (9)
1. a bipolarity blue emitting phosphor compound, is characterized in that, this compound has following structural formula:
2. a preparation method for bipolarity blue emitting phosphor compound, is characterized in that, comprises the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
b be added into and contain in the organic solvent that catalyzer and alkaline solution exist, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, obtain structural formula and be after separating-purifying
bipolarity blue emitting phosphor compound; Wherein, the mol ratio of compd A and compd B is 1:1～1.2.
3. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, it is characterized in that, described catalyzer is that mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that the palladium of 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
6. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
7. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～36 hours.
8. the preparation method of bipolarity blue emitting phosphor compound according to claim 2, is characterized in that, the separating-purifying of described bipolarity blue emitting phosphor compound comprises the steps:
After Suzuki coupling reaction finishes, with dichloromethane extraction reaction solution repeatedly, then merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, it is that leacheate separates and obtains crystalline substance through silica gel column chromatography with the mixed solution of ethyl acetate that crude product adopts the sherwood oil that volume ratio is 10:1, subsequently crystalline substance after 50 ℃ of dry 24h, is obtained to described bipolarity blue emitting phosphor compound under vacuum.
Bipolarity blue emitting phosphor compound claimed in claim 1 in organic electroluminescence device as the application of the material of main part of luminescent layer.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104342124A (en) * | 2014-10-23 | 2015-02-11 | 上海道亦化工科技有限公司 | Benzimidazole based phosphorescent luminescent main body material |
| CN107540663A (en) * | 2017-07-31 | 2018-01-05 | 华南理工大学 | Soluble high glass-transition temperature bipolar host material and its preparation and application |
| WO2018166096A1 (en) * | 2017-03-16 | 2018-09-20 | 武汉华星光电技术有限公司 | Organic light-emitting device and method for manufacturing same |
-
2012
- 2012-11-08 CN CN201210444207.9A patent/CN103804360A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104342124A (en) * | 2014-10-23 | 2015-02-11 | 上海道亦化工科技有限公司 | Benzimidazole based phosphorescent luminescent main body material |
| WO2018166096A1 (en) * | 2017-03-16 | 2018-09-20 | 武汉华星光电技术有限公司 | Organic light-emitting device and method for manufacturing same |
| US10825994B2 (en) | 2017-03-16 | 2020-11-03 | Wuhan China Star Optoelectronics Technology, Ltd. | Organic light emitting device and preparation method thereof |
| CN107540663A (en) * | 2017-07-31 | 2018-01-05 | 华南理工大学 | Soluble high glass-transition temperature bipolar host material and its preparation and application |
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Application publication date: 20140521 |