CN104449664A - Organic semiconductor material, preparation method thereof and electroluminescent device - Google Patents

Organic semiconductor material, preparation method thereof and electroluminescent device Download PDF

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CN104449664A
CN104449664A CN201310438584.6A CN201310438584A CN104449664A CN 104449664 A CN104449664 A CN 104449664A CN 201310438584 A CN201310438584 A CN 201310438584A CN 104449664 A CN104449664 A CN 104449664A
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organic semiconductor
semiconductor material
compd
preparation
solution
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周明杰
张振华
王平
张娟娟
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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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Abstract

The invention provides an organic semiconductor material. The organic semiconductor material has the chemical formula represented by a formula shown in specifications. The organic semiconductor material provided by the invention has a relatively high triplet energy level, so that energy is effectively prevented from being transferred back to a main body material during luminescence; due to the phosphorescent main body material with electron transmission capability, the electron transmission capability is enhanced, the balance of current carrier transmission is facilitated, the luminescence efficiency is greatly increased, and the thermal stability is relatively high. The invention further provides a preparation method of the organic semiconductor material and an electroluminescent device containing the organic semiconductor material.

Description

A kind of organic semiconductor material, preparation method and electroluminescent device
Technical field
The invention belongs to field of photovoltaic materials, be specifically related to a kind of organic semiconductor material, preparation method and electroluminescent device.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide and changes luminescent properties by chemical structure fine setting makes rich color, easily realize the advantages such as resolving power is high, lightweight, large-area flat-plate display, 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 singlet and triplet excitons can all be caught by they, thus realize the internal quantum efficiency of 100%.But, because the excited state exciton lifetime of transition metal complex is relatively long, cause unwanted triplet state-triplet state (T 1-T 1) cancellation in device real work.In order to overcome this problem, triplet emission thing is often doped in organic host material by investigators.
In recent years, green and red phosphorescent OLED shows gratifying electroluminescent efficiency, but red phosphorescent device is little efficiently, and major cause lacks suitable material of main part.
Summary of the invention
For solving the problem, the invention provides a kind of organic semiconductor material and there is higher triplet, effectively prevent energy in luminescence process from returning to material of main part, there is the phosphorescent light body material of electron transport ability, electron transport ability is strengthened, and is conducive to carrier transport balance, greatly improves luminous efficiency, and have higher thermostability, organic semiconductor material of the present invention is that ruddiness phosphorescent light body material provides new selectable kind.Present invention also offers the preparation method of this organic semiconductor material, and comprise the electroluminescent device of this organic semiconductor material.
On the one hand, the invention provides a kind of organic semiconductor material, the chemical formula of described organic semiconductor material is as follows:
Second aspect, the invention provides a kind of preparation method of organic semiconductor material, comprises the steps:
Compd A is provided: and compd B: under an inert atmosphere, first compd A is dissolved in organic solvent, the concentration forming solution is 0.3mol/L ~ 0.5mol/L, then compd B, mineral alkali and catalyzer are added in reactant at 70 ~ 120 DEG C, carry out reaction 6 ~ 15 hours, the mol ratio of described compd A and compd B is 1:2 ~ 1:2.4, stopped reaction cool to room temperature, filter and wash with water and obtain pale solid, crude product adopts normal hexane to be that the chemical formula that leacheate obtains intermediate product through silica gel column chromatography separation is as follows:
Again described intermediate product is dissolved in the second solvent under zero degrees celsius condition, then m-chlorobenzoic acid is instilled in described second solvent, react 8 hours ~ 16 hours at ambient temperature, then add saturated NaHCO 3and stir 20 minutes ~ 40 minutes, be separated organic layer, the structural formula that anhydrous magnesium sulfate drying obtains organic semiconductor material is:
Preferably, the preparation method of described organic semiconductor material comprises post-processing step further, the preparation method of described organic semiconductor material comprises post-processing step further, described post-processing step is specially: stopped reaction is obtained organic semiconductor material and adopt toluene and alcohol mixed solvent to carry out recrystallization, namely vacuum-drying obtain target product.
Preferably, described organic solvent is selected from least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF, and described second solvent is selected from the one in methylene dichloride, trichloromethane, tetrahydrofuran (THF) and ether.
Preferably, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate, cesium carbonate solution and potassium phosphate solution, and the solute in described alkaline solution and the mol ratio of compd A are 2:1 ~ 2.5:1.
Preferably, described catalyzer is copper powder, cuprous iodide or Red copper oxide.
Preferably, the mol ratio of described catalyzer and described compd A is 1:10 ~ 1:5.
The third aspect, the invention provides a kind of electroluminescent device, comprise the substrate with anode, luminescent layer and the cathode layer that stack gradually, described luminescent layer is the mixture of material of main part and guest materials, the organic semiconductor material that wherein material of main part is as follows: guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close iridium, three [1-phenyl isoquinolin quinoline-C2, N] iridium or two [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium (III).
Preferably, the mass percent of described material of main part and described guest materials is 5% ~ 30%.
Preferably, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
The invention provides a kind of organic semiconductor material, preparation method and electroluminescent device, there is following beneficial effect: there is higher triplet, effectively prevent energy in luminescence process from returning to material of main part, have the phosphorescent light body material of electron transport ability, electron transport ability is strengthened, and is conducive to carrier transport balance, greatly improve luminous efficiency, and have higher thermostability, synthetic method is simple, can be used for ruddiness phosphorescent light body material.
Accompanying drawing explanation
Fig. 1 is the structural representation of the organic electroluminescence device obtained for material of main part with organic semiconductor material obtained in embodiment 1;
Fig. 2 is the thermogravimetic analysis (TGA) figure of organic semiconductor material obtained in embodiment 1.
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 monomer A, monomers B all commercially obtain.
The invention provides a kind of organic semiconductor material, the chemical formula of described organic semiconductor material is as follows:
This organic semiconductor material has higher triplet, effectively prevent energy in luminescence process from returning to material of main part, there is the phosphorescent light body material of electron transport ability, electron transport ability is strengthened, be conducive to carrier transport balance, greatly improve luminous efficiency, and have higher thermostability, therefore organic semiconductor material of the present invention has ruddiness phosphorescent light body material.
The invention provides a kind of preparation method of organic semiconductor material, comprise the steps:
Compd A is provided: and compd B: under an inert atmosphere, first compd A is dissolved in organic solvent, the concentration forming solution is 0.3mol/L ~ 0.5mol/L, then compd B, mineral alkali and catalyzer are added in reactant at 70 ~ 120 DEG C, carry out reaction 6 ~ 15 hours, the mol ratio of described compd A and compd B is 1:2 ~ 1:2.4, stopped reaction cool to room temperature, filter and wash with water and obtain pale solid, crude product adopts normal hexane to be that the chemical formula that leacheate obtains intermediate product through silica gel column chromatography separation is as follows:
Again described intermediate product is dissolved in the second solvent under zero degrees celsius condition, then m-chlorobenzoic acid is instilled in described second solvent, react 8 hours ~ 16 hours at ambient temperature, then add saturated NaHCO 3and stir 20 minutes ~ 40 minutes, be separated organic layer, the structural formula that anhydrous magnesium sulfate drying obtains organic semiconductor material is:
The preparation method of described organic semiconductor material comprises post-processing step further, and described post-processing step is specially: stopped reaction is obtained organic semiconductor material and adopt toluene and alcohol mixed solvent to carry out recrystallization, namely vacuum-drying obtain target product.
Described vacuum drying condition is 50 ~ 70 DEG C of dryings 12 ~ 24 hours;
Described organic solvent is selected from tetrahydrofuran (THF) (THF), acetonitrile (MeCN), toluene (Tol) and N, at least one in dinethylformamide (DMF), described second solvent is selected from the one in methylene dichloride, trichloromethane, tetrahydrofuran (THF) and ether.
Described alkaline solution 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 solute in described alkaline solution and the mol ratio of compd A are 2:1 ~ 2.5:1.
Described 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.
Have employed better simply synthetic route, thus reduce technical process, starting material are cheap and easy to get, and manufacturing cost is reduced.
The invention provides a kind of electroluminescent device, comprise the substrate with anode, luminescent layer and the cathode layer that stack gradually, described luminescent layer is the mixture of material of main part and guest materials, the organic semiconductor material that wherein material of main part is as follows: guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close iridium, three [1-phenyl isoquinolin quinoline-C2, N] iridium or two [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium (III).
The mass percent of described guest materials and described material of main part is 5% ~ 30%.
Described anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
Based on the organic luminescent device red-emitting of this material, and luminous efficiency is high.
Embodiment 1:
The preparation process preparation process of 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes is as follows:
Under nitrogen protection; by 9; 9-bis-(4-bromophenyl)-9H-fluorenes (38.1g; 80mmol) be dissolved in 200mLN, in dinethylformamide (DMF) solution, then add thiophenol (17.6g; 160mmol); salt of wormwood (22.1g, 160mmol) and cuprous iodide (1.52g, 8mmol).Reactant stirring reaction 6 hours at 120 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to be separated through silica gel column chromatography and obtains intermediate product.Productive rate is 87%.
Under ice bath, intermediate product (21.4g, 40mmol) is dissolved in methylene dichloride (DCM) solution of 120mL, is then instilled in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).Mixture at room temperature stirring reaction after 12 hours, then add 300mL saturated sodium bicarbonate solution and stir 30 minutes.Be separated organic layer, anhydrous magnesium sulfate drying.Crude product adopts toluene and alcohol mixed solvent, and toluene and ethanol contend are than being 5:1, recrystallization, then 50 DEG C of dry 24h product 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes under vacuo, productive rate 95%.
Test data of experiment: mass spectrum: m/z598.1(M ++ 1); Ultimate analysis (%) C 37h 26o 4s 2: theoretical value: C74.22, H4.38, O10.69, S10.71; Measured value: C74.27, H4.34, O10.75, S10.68.
See the thermogravimetic analysis (TGA) figure that accompanying drawing 2 is organic semiconductor material prepared by the present embodiment, thermogravimetric curve (TGA) test is carried out on Perkin-Elmer Series7, and under nitrogen gas stream protection, heat-up rate is 10K/min.The thermal weight loss temperature of 5% is 372 DEG C as seen from the figure.
By test for low temperature phosphorescence spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate its triplet emission characteristic.Under the liquid nitrogen of 77K, bill of material reveals very strong red light phosphorescent emissions, and emission peak is at 602nm, and corresponding triplet energy state is 2.06eV, is much higher than phosphor material Ir (piq) 3triplet energy state (1.97eV), test data result shows that our material can be used as bipolarity red phosphorescent material of main part.
Adopt transition time (TOP) method to test the hole mobility of organic semiconductor material prepared by the present embodiment, test result is 4.7 × 10 -4cm 2/ Vs.
Embodiment 2:
The preparation process preparation process of 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes is as follows:
Under nitrogen protection; by 9; 9-bis-(4-bromophenyl)-9H-fluorenes (38.1g; 80mmol) be dissolved in 267mL toluene (Tol) solution, then add thiophenol (19.4g, 176mmol); cesium carbonate (57.2g; 176mmol), copper powder (0.768g, 12mmol).Reactant stirring reaction 9 hours at 110 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to be separated through silica gel column chromatography and obtains intermediate product.Productive rate is 90%.
Under ice bath, intermediate product (21.4g, 40mmol) is dissolved in the chloroform soln of 120mL, is then instilled in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).Mixture at room temperature stirring reaction after 8 hours, then add 300mL saturated sodium bicarbonate solution and stir 20 minutes.Be separated organic layer, anhydrous magnesium sulfate drying.Crude product adopts toluene and alcohol mixed solvent, and toluene and ethanol contend are than being 5:1, recrystallization, then 50 DEG C of dry 24h product 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes under vacuo, productive rate 85%.
Embodiment 3:
The preparation process preparation process of 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes is as follows:
Under nitrogen protection; by 9; 9-bis-(4-bromophenyl)-9H-fluorenes (38.1g; 80mmol) be dissolved in 160mL acetonitrile (MeCN) solution; then thiophenol (21.1g, 192mmol) is added, potassiumphosphate (39g; 184mmol) with Red copper oxide (2.3g, 16mmol).Reactant stirring reaction 12 hours at 90 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to be separated through silica gel column chromatography and obtains intermediate product.Productive rate is 95%.
Under ice bath, intermediate product (21.4g, 40mmol) is dissolved in the tetrahydrofuran solution of 120mL, is then instilled in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).Mixture at room temperature stirring reaction after 14 hours, then add 300mL saturated sodium bicarbonate solution and stir 40 minutes.Be separated organic layer, anhydrous magnesium sulfate drying.Crude product adopts toluene and alcohol mixed solvent, and toluene and ethanol contend are than being 5:1, recrystallization, then 50 DEG C of dry 24h product 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes under vacuo, productive rate 91%.
Embodiment 4:
The preparation process preparation process of 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes is as follows:
Under nitrogen protection; by 9; 9-bis-(4-bromophenyl)-9H-fluorenes (38.1g; 80mmol) be dissolved in 178mL tetrahydrofuran (THF) (THF) solution; then thiophenol (20.2g, 184mmol) is added, sodium carbonate (20.4g; 192mmol) with cuprous iodide (2.6g, 13.6mmol).Reactant stirring reaction 15 hours at 70 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to be separated through silica gel column chromatography and obtains intermediate product.Productive rate is 88%.
Under ice bath, intermediate product (21.4g, 40mmol) is dissolved in the diethyl ether solution of 120mL, is then instilled in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).Mixture at room temperature stirring reaction after 16 hours, then add 300mL saturated sodium bicarbonate solution and stir 30 minutes.Be separated organic layer, anhydrous magnesium sulfate drying.Crude product adopts toluene and alcohol mixed solvent, and toluene and ethanol contend are than being 5:1, recrystallization, then 50 DEG C of dry 24h product 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes under vacuo, productive rate 89%.
Embodiment 5:
The preparation process preparation process of 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes is as follows:
Under nitrogen protection; by 9; 9-bis-(4-bromophenyl)-9H-fluorenes (38.1g; 80mmol) be dissolved in 229mLN, in dinethylformamide (DMF) solution, then add thiophenol (18.5g; 168mmol); potassiumphosphate (42.4g, 200mmol) and copper powder (1g, 16mmol).Reactant stirring reaction 15 hours at 100 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to be separated through silica gel column chromatography and obtains intermediate product, and productive rate is 86%.
Under ice bath, intermediate product (21.4g, 40mmol) is dissolved in methylene dichloride (DCM) solution of 120mL, is then instilled in the dichloromethane solution of the m-chloro-benzoic acid of 90mL (mCPBA).Mixture at room temperature stirring reaction after 10 hours, then add 300mL saturated sodium bicarbonate solution and stir 30 minutes.Be separated organic layer, anhydrous magnesium sulfate drying.Crude product adopts toluene and alcohol mixed solvent, and toluene and ethanol contend are than being 5:1, recrystallization, then 50 DEG C of dry 24h product 9,9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes under vacuo, productive rate 93%.
Application Example
Organic electroluminescence device 300, as Fig. 1, it comprises substrate 301 to its structure, anode 302, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308.
The material of substrate 301 in the present embodiment is glass, vacuum plating anode 302 successively in substrate 301, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electron injection buffer layer 307, negative electrode 308, anode 302 adopts square resistance to be the tin indium oxide of 10 ~ 20 Ω/, thickness is 150nm, hole injection layer 303 adopts CuPc, thickness is 30nm, hole transmission layer 304 adopts N, N '-phenylbenzene-N, N '-(1-naphthyl)-1, 1 '-biphenyl-4, 4 '-diamines, thickness is 20nm, the compound 9 that luminescent layer 305 main body luminescent material adopts the invention process 1 to prepare, 9-bis-(4-(phenylSulphon) phenyl)-9H-fluorenes, and to take material of main part as benchmark doping mass percent be 25% guest emitting material three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) Ir(piq) 3, luminescent layer 305 thickness is 20nm, and electron transfer layer 306 adopts 4,7-phenylbenzene-1,10-phenanthroline, and thickness is 30nm, and electron injection buffer layer 307 adopts lithium fluoride, and thickness is 1nm, and negative electrode 308 adopts metallic aluminium, and thickness is 100nm.
Organic layer and metal level all adopt thermal evaporation process to deposit, and vacuum tightness is 10 -3~ 10 -5pa, the thickness of film adopts film thickness monitoring instrument to monitor, except guest materials, the vaporator rate of all organic materialss is second, the vaporator rate of lithium fluoride is second, the vaporator rate of metallic aluminium is second.
This electroluminescent device has higher luminous efficiency, can be widely used in the illumination field such as redness or white.Current versus brightness-the voltage characteristic of device is all completed in atmosphere at room temperature by all measurements completed with Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) correcting silicon photoelectric diode.Result shows: the trigger voltage of device is 3.7V, at 1000cd/m 2brightness under, luminous efficiency is 8.2lm/W.
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.

Claims (10)

1. an organic semiconductor material, is characterized in that, the chemical formula of described organic semiconductor material is as follows:
2. a preparation method for organic semiconductor material, is characterized in that, comprises the steps:
Compd A is provided: and compd B: under an inert atmosphere, first compd A is dissolved in organic solvent, the concentration forming solution is 0.3mol/L ~ 0.5mol/L, then compd B, mineral alkali and catalyzer are added in reactant at 70 ~ 120 DEG C, carry out reaction 6 ~ 15 hours, the mol ratio of described compd A and compd B is 1:2 ~ 1:2.4, stopped reaction cool to room temperature, filter and wash with water and obtain pale solid, crude product adopts normal hexane to be that the chemical formula that leacheate obtains intermediate product through silica gel column chromatography separation is as follows:
Again described intermediate product is dissolved in the second solvent under zero degrees celsius condition, then m-chlorobenzoic acid is instilled in described second solvent, react 8 hours ~ 16 hours at ambient temperature, then add saturated NaHCO 3and stir 20 minutes ~ 40 minutes, be separated organic layer, the structural formula that anhydrous magnesium sulfate drying obtains organic semiconductor material is:
3. preparation method as claimed in claim 2, it is characterized in that, the preparation method of described organic semiconductor material comprises post-processing step further, described post-processing step is specially: stopped reaction is obtained organic semiconductor material and adopt toluene and alcohol mixed solvent to carry out recrystallization, namely vacuum-drying obtain target product.
4. preparation method as claimed in claim 2, it is characterized in that, described organic solvent is selected from least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF, and described second solvent is selected from the one in methylene dichloride, trichloromethane, tetrahydrofuran (THF) and ether.
5. preparation method as claimed in claim 2, it is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate, cesium carbonate solution and potassium phosphate solution, and the solute in described alkaline solution and the mol ratio of compd A are 2:1 ~ 2.5:1.
6. preparation method as claimed in claim 2, it is characterized in that, described catalyzer is copper powder, cuprous iodide or Red copper oxide.
7. preparation method as claimed in claim 2, it is characterized in that, the mol ratio of described catalyzer and described compd A is 1:10 ~ 1:5.
8. an electroluminescent device, is characterized in that, comprises the substrate with anode, luminescent layer and the cathode layer that stack gradually, and described luminescent layer is the mixture of material of main part and guest materials, the organic semiconductor material that wherein material of main part is as follows:
guest materials is two (4,6-difluorophenyl pyridinato-N, C2) pyridinecarboxylic closes iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close iridium, three [1-phenyl isoquinolin quinoline-C2, N] iridium or two [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium (III).
9. electroluminescent device as claimed in claim 8, it is characterized in that, the mass percent of described material of main part and described guest materials is 5% ~ 30%.
10. electroluminescent device as claimed in claim 8, it is characterized in that, described anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
CN201310438584.6A 2013-09-24 2013-09-24 Organic semiconductor material, preparation method thereof and electroluminescent device Pending CN104449664A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113979903A (en) * 2021-11-15 2022-01-28 杭州师范大学 Organic thermal activation delayed fluorescent material containing phenylsulfone-spirofluorene structural unit, preparation method and application

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113979903A (en) * 2021-11-15 2022-01-28 杭州师范大学 Organic thermal activation delayed fluorescent material containing phenylsulfone-spirofluorene structural unit, preparation method and application
CN113979903B (en) * 2021-11-15 2024-02-13 杭州师范大学 Organic thermal activation delayed fluorescence material containing phenylsulfone-spirofluorene structural unit, preparation method and application

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