CN104560015A - Anthracene type blue-light organic electroluminescent material and preparation method and application thereof - Google Patents
Anthracene type blue-light organic electroluminescent material and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the field of organic electroluminescent materials and discloses an anthracene type blue-light organic electroluminescent material and a preparation method and application thereof. The material has a structural formula shown in descriptions. According to the anthracene type blue-light organic electroluminescent material disclosed by the invention, fluorene has relatively good rigidity and planarity and is good in thermal stability; carbazole is of an aza aromatic ring structure and has an excellent hole transport property; anthracene has high fluorescent quantum yield and is suitable for being used for preparing a blue-light material, and organic luminescent devices based on the blue-light material are relatively high in efficiency and good in thermal stability.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, particularly relate to a kind of anthracene blue-ray organic electroluminescent material and its preparation method and application.
Background technology
Since the first times such as C.W.Tang report Organic Light Emitting Diode (OLED), no matter be small molecules or polymer LED, all achieved huge development.Its potential application is full color flat-panel monitor and solid-state white illumination.In three primary colours, ruddiness and green diode are all close to the requirement of practical application, but blue light material is due to greater band gap, and lower highest occupied molecular orbital (HOMO) energy level, therefore there is larger carrier injection energy barrier; Meanwhile, because emitted energy is high, unstable, easily energy trasfer occurs and cause transmitting look impure, so development is relatively slow.The blue light emitting material of research and development high-level efficiency, high stable performance, remains a difficult problem.
In the exploitation of material, have two kinds of thinkings available, one is research and develop novel blue phosphor materials, and another is the blue fluorescent material of development of new.One large advantage of fluorescent material is stable, and efficiency decay is severe unlike phosphorescent devices.Although many blue light materials are in the news, high-level efficiency, the material that emitting performance is stable or few.
Anthracene derivant becomes the focus of research with the fluorescence quantum yield of its superelevation and excellent Electroluminescence Properties and electrochemical properties, be widely used in and build in Efficiency of Organic Electroluminescent Devices.In numerous anthracene derivative, 9,10-dinaphthyl anthracene (ADN) becomes the significant molecule of blue fluorescent material due to the photoluminescent property of excellence and good chemical property.But it can not form out high-quality film, and be easy to crystallization by the film of vapor deposition, cause surface irregularity, crystal boundary and pin hole, finally cause device failure.As a rule, have high second-order transition temperature amorphous material film, more can withstand decocting of heat, therefore device performance is stable many.Thus, have higher Tg luminescent material, in device use procedure, more can keep the stability of film morphology.
Summary of the invention
Problem to be solved by this invention is to provide a kind of good stability, the anthracene blue-ray organic electroluminescent material that luminous efficiency is high.
For achieving the above object, anthracene blue-ray organic electroluminescent material provided by the invention, its structure is such as formula shown:
i.e. 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole.
Another object of the embodiment of the present invention is to provide the preparation method of the anthracene blue-ray organic electroluminescent material that a kind of synthetic route is simple, material is cheap and easy to get, and described preparation method comprises the steps:
The compd A providing following structural formula to represent respectively and B,
Under oxygen-free environment, be dissolve mol ratio during the compd A of 1:1 ~ 1.2 and B are added into containing catalyzer and alkaline solution organic solvent, obtain mixing solutions, mixing solutions carries out Suzuki coupling reaction 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains the described anthracene blue-ray organic electroluminescent material that following structural formula represents:
Wherein, described catalyzer is organic palladium bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium; Or
Described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl; Mixture can be palladium and three (o-methyl-phenyl-) phosphine mixture or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl mixture;
The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
Described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and the alkali solute in described alkaline solution and the mol ratio of compd A are 20:1.
In a preferred embodiment, organic solvent is selected from solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
In a preferred embodiment, the temperature of reaction of described Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
In preferred embodiment, purified reaction liquid process also comprises step:
After Suzuki coupling reaction stops being cooled to room temperature, the organic phase extracting and obtain repeatedly also is merged with dichloromethane extraction reaction solution, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.
In described preparation method, oxygen-free environment is made up of at least one gas in nitrogen, argon gas.
Above-mentioned preparation method's principle is simple, easy and simple to handle, low for equipment requirements, can wide popularization and application.
Another object of the present invention is to provide the application of above-mentioned anthracene blue-ray organic electroluminescent material in organic electroluminescence device luminescent layer field.
Adopt above-mentioned anthracene blue-ray organic electroluminescent material to obtain organic electroluminescence device, its structure comprise stack gradually substrate, anode layer, hole injection layer, hole transport/electronic barrier layer, luminescent layer, electric transmission/hole blocking layer, electron injecting layer and cathode layer; Wherein, the material of each functional layer is as follows:
Substrate is glass;
The material of anode layer, for adopting tin indium oxide, i.e. ITO, after ITO is combined with glass, again referred to as ito glass, or is directly called for short ITO;
The material of hole injection layer is PEDOT: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 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole (representing with P);
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 above-mentioned organic electroluminescence device also can be expressed as:
ITO/PEDOT:PSS/TPD/P/BPhen/LiF/Al; Wherein, brace represents laminate structure.
In anthracene blue-ray organic electroluminescent material provided by the invention, fluorenes has good rigidity and planarity, and thermal stability is good; Carbazole is nitrogen heteroaromatic rings structure, has excellent hole transport performance; Anthracene has high fluorescence quantum yield, is applicable to doing blue light material, and the organic luminescent device efficiency based on described blue light material is higher, and Heat stability is good.
Separately, the preparation method of above-mentioned blue-ray organic electroluminescent material, have employed better simply synthetic route, thus reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the differential scanning calorimetric curve of the anthracene blue-ray organic electroluminescent material that embodiment 1 obtains;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 5 obtains.
Embodiment
In order to understand the content of patent of the present invention better, technology case of the present invention is further illustrated 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 purchased from lark prestige Science and Technology Ltd..
Embodiment 1: the anthracene blue-ray organic electroluminescent material of the present embodiment, for: 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole, preparation process is as follows:
Under argon shield, by bromo-for 9-10-(9H-fluorenes-9-base) anthracene (84mg, 0.2mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (74mg, 0.2mmol) add in the flask filling 10ml toluene solvant, after abundant dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then bis-triphenylphosphipalladium palladium dichloride (5.6mg, 0.008mmol) is added; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.Productive rate is 81%.Mass spectrum: m/z583.2(M
++ 1); Ultimate analysis (%) C
45h
29n: theoretical value C92.59, H5.01, N2.40; Measured value: C92.67, H5.12, N2.24.
Fig. 1 is the differential scanning calorimetric curve of the anthracene blue-ray organic electroluminescent material that embodiment 1 obtains; Differential scanning calorimetric curve (DSC) is completed by the measurement of Perkin-Elmer DSC-7 Thermo System, and all measurements all complete in atmosphere at room temperature.As shown in Figure 1, second-order transition temperature (T
g) be 130 DEG C.
Embodiment 2: the anthracene blue-ray organic electroluminescent material of the present embodiment, for: 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole, preparation process is as follows:
Under nitrogen and argon gas gas mixture are protected; by bromo-for 9-10-(9H-fluorenes-9-base) anthracene (126mg; 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (122mg; 0.33mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after the gas mixture air-discharging passing into nitrogen and argon gas after abundant dissolving is about 20min; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein; sodium bicarbonate (3mL, 2mol/L) solution is added again after abundant dissolving.After the gas mixture air-discharging of fully logical nitrogen and argon gas is about 10min again, two-mouth bottle is joined 70 DEG C and carry out Suzuki coupling reaction 48h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.Productive rate is 86%.
Embodiment 3: the anthracene blue-ray organic electroluminescent material of the present embodiment, for: 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole, preparation process is as follows:
Under nitrogen protection, by bromo-for 9-10-(9H-fluorenes-9-base) anthracene (126mg, 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (133mg, 0.36mmol), palladium (3.5mg, 0.015mmol) He three (o-methyl-phenyl-) phosphine (21mg, 0.06mmol) join the N filling 12mL, in the flask of dinethylformamide, salt of wormwood (3mL is added after abundant dissolving, 2mol/L) solution, after in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.Productive rate is 80%.
Embodiment 4: the anthracene blue-ray organic electroluminescent material of the present embodiment, for: 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole, preparation process is as follows:
Under nitrogen protection; by bromo-for 9-10-(9H-fluorenes-9-base) anthracene (126mg; 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (133mg; 0.36mmol), three or two argon benzyl acetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N filling 12mL; in the flask of dinethylformamide; sodium carbonate (3mL, 2mol/L) solution is added after abundant dissolving.After in flask, logical nitrogen purge gas is about 30min subsequently; Flask is heated to 90 DEG C and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.Productive rate is 86%.
Embodiment 5:
The present embodiment is organic electroluminescence device, its anthracene blue-ray organic electroluminescent material obtained with the embodiment of the present invention 1, namely 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole is as emitting layer material.
As shown in Figure 2, this organic electroluminescence device comprises the substrate layer 1(ITO be made up of substrate of glass and the anode layer that is deposited on substrate of glass one surface and represents), hole injection layer 2(material is PEDOE:PSS), hole transport/electronic barrier layer 3(material is N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1, 1'-biphenyl-4, 4'-diamines (TPD)), luminescent layer 4(material is 9-(4-(10-(9H-fluorenes-9-base) anthracene-9-base) phenyl)-9H-carbazole (representing with P)), (material is 4 to electric transmission/hole blocking layer 5, 7-phenylbenzene-1, 10-phenanthroline (BPhen)), electron injecting layer 6(material is LiF) and cathode layer 7(material be Al).
The concrete grammar that this organic electroluminescence device makes is:
First, at anode layer (ITO) the spin coating PEDOT:PSS of the substrate layer through cleaning, dry, obtained hole injection layer;
Secondly, adopt hot evaporation process, on hole injection layer surface successively evaporation hole transport/electronic barrier layer (TPD), luminescent layer, electric transmission/hole blocking layer (BPhen), electron injecting layer (LiF) and cathode layer (Al);
After above-mentioned technique is complete, obtained organic electroluminescence device.
The structure of this organic electroluminescence device can be expressed as: ITO(150nm)/PEDOT:PSS (30nm)/TPD (40nm)/P(30nm)/BPhen (35nm)/LiF (1.5nm)/Al (150nm); Wherein, the thickness of each functional layer of numeric representation in bracket.
Test the current versus brightness-voltage characteristic of this organic electroluminescence device, test completes by with Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) correcting silicon photoelectric diode; Test result is: the maximum luminous efficiency of organic electroluminescence device is 7.3cd/A, and high-high brightness is 21840cd/m
2.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but therefore can not be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.9 -->
Claims (10)
1. an anthracene blue-ray organic electroluminescent material, is characterized in that, its structural formula is as follows:
2. a preparation method for anthracene blue-ray organic electroluminescent material as claimed in claim 1, is characterized in that, its following steps:
Under oxygen-free environment, be that the structural formula of 1:1 ~ 1.2 is by mol ratio
compd A and structural formula be
compd B be added into containing catalyzer and alkaline solution organic solvent in dissolve, obtain mixing solutions; This mixing solutions carried out Suzuki coupling reaction after 12 ~ 48 hours at 70 ~ 130 DEG C, stopped reaction cool to room temperature, and purified reaction liquid, obtaining structural formula is
described anthracene blue-ray organic electroluminescent material.
3. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 2, is characterized in that, described catalyzer is bis-triphenylphosphipalladium palladium dichloride or tetra-triphenylphosphine palladium, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
4. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 2, it is characterized in that, described catalyzer is mol ratio is the organic palladium of 1:4 ~ 8 and the mixture of organophosphorus ligand, and the mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 4, it is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums, described organophosphorus ligand is three (o-methyl-phenyl-) phosphines or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 2, it is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and the alkali solute in described alkaline solution and the mol ratio of compd A are 20:1.
7. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 2, is characterized in that, it is at least one in toluene, DMF, tetrahydrofuran (THF) that described organic solvent is selected from solvent.
8. the preparation method of anthracene blue-ray organic electroluminescent material according to claim 2, is characterized in that, the temperature of reaction of described Suzuki coupling reaction is 90 ~ 120 DEG C, and the reaction times is 24 ~ 36 hours.
9., according to the preparation method of the arbitrary described anthracene blue-ray organic electroluminescent material of claim 2 to 8, it is characterized in that, purified reaction liquid process also comprises step:
After Suzuki coupling reaction stops being cooled to room temperature, the organic phase extracting and obtain repeatedly also is merged with dichloromethane extraction reaction solution, then be spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, crude product adopts volume ratio to be sherwood oil and the ethyl acetate mixtures of 10:1 to be leacheate to be separated through silica gel column chromatography and obtains crystalline substance, after this crystalline substance being placed in vacuum state 50 DEG C of dry 24h of environment, obtain described anthracene blue-ray organic electroluminescent material.
10. the application of anthracene blue-ray organic electroluminescent material according to claim 1 in organic electroluminescence device luminescent layer field.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111925314A (en) * | 2020-07-23 | 2020-11-13 | 大同煤矿集团有限责任公司 | Carbazole and anthracene-based blue host material capable of emitting light from host |
| CN113105382A (en) * | 2021-03-26 | 2021-07-13 | 华南理工大学 | Biphenyl modified carbazole group anthracene-based deep blue light material and preparation and application thereof |
-
2013
- 2013-10-23 CN CN201310503815.7A patent/CN104560015A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111925314A (en) * | 2020-07-23 | 2020-11-13 | 大同煤矿集团有限责任公司 | Carbazole and anthracene-based blue host material capable of emitting light from host |
| CN113105382A (en) * | 2021-03-26 | 2021-07-13 | 华南理工大学 | Biphenyl modified carbazole group anthracene-based deep blue light material and preparation and application thereof |
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