CN104119383A - Organic semiconductor material, preparation method thereof and electroluminescent device - Google Patents
Organic semiconductor material, preparation method thereof and electroluminescent device Download PDFInfo
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- CN104119383A CN104119383A CN201310147682.4A CN201310147682A CN104119383A CN 104119383 A CN104119383 A CN 104119383A CN 201310147682 A CN201310147682 A CN 201310147682A CN 104119383 A CN104119383 A CN 104119383A
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- JLCODVSWSDAKDU-UHFFFAOYSA-N Brc1ccc(C(C2c3ccccc3)C2c2ccccc2)cc1 Chemical compound Brc1ccc(C(C2c3ccccc3)C2c2ccccc2)cc1 JLCODVSWSDAKDU-UHFFFAOYSA-N 0.000 description 1
- PQJHJZKSUMQPQZ-YAZXXGGHSA-N C/C=C(\C1=C/C)/c2cc(-c(cc3)cc(c4ccccc44)c3[n]4-c(cc3)ccc3P(c3ccccc3)(c3ccccc3)=O)ccc2N1c(cc1)ccc1P(c1ccccc1)(c1ccccc1)=O Chemical compound C/C=C(\C1=C/C)/c2cc(-c(cc3)cc(c4ccccc44)c3[n]4-c(cc3)ccc3P(c3ccccc3)(c3ccccc3)=O)ccc2N1c(cc1)ccc1P(c1ccccc1)(c1ccccc1)=O PQJHJZKSUMQPQZ-YAZXXGGHSA-N 0.000 description 1
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Abstract
The invention provides an organic semiconductor material, which has a chemical formula shown as below. The organic semiconductor material has bipolar carrier transmission capability to reach hole transport and electron transport balance in a luminescent layer; and the organic semiconductor material also has high triplet state energy level and excellent thermal stability, and effectively prevents back passing of energy to the host material in the luminescence process, thus greatly improving the luminous efficiency. The invention also provides a preparation method of the organic semiconductor material, and an electroluminescent device containing the organic semiconductor material.
Description
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 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 unwanted 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.
In recent years, green and red phosphorescent OLED device exhibits goes out gratifying electroluminescent efficiency.And blue phosphorescent device is little efficiently, major cause is to lack to have good carrier transmission performance and higher triplet (E simultaneously
t) material of main part.
Summary of the invention
For addressing the above problem, the invention provides a kind of organic semiconductor material, this organic semiconductor material has bipolarity carrier transport ability, makes hole and electric transmission balance in luminescent layer; Also there is higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, organic semiconductor material of the present invention provides new selectable kind for bipolarity blue emitting phosphor material of main part.The present invention also provides the preparation method of this organic semiconductor material, and the electroluminescent device that comprises 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 inert atmosphere, first compd A is dissolved in organic solvent, then compd B, mineral alkali and catalyzer are added in reactant and at 70~120 DEG C, reacted 6~15 hours, the mol ratio of described compd A and compd B is 1:2~1:2.4, and it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
Preferably, the preparation method of described organic semiconductor material further comprises post-processing step, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: using stopped reaction obtain organic semiconductor material adopt normal hexane solvent as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
Preferably, described organic solvent is selected from least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF.
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, and wherein material of main part is organic semiconductor material as follows:
guest materials is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
Preferably, the mass percent of described material of main part and described guest materials is 5%~15%.
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 bipolarity carrier transport ability, make hole and electric transmission balance in luminescent layer; Also have higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, synthetic method is simple, can be used for blue emitting phosphor material of main part.
Brief description of the drawings
Fig. 1 is the thermogravimetic analysis (TGA) figure of the organic semiconductor material that makes in embodiment 1;
The structural representation of Fig. 2 organic electroluminescence device that to be organic semiconductor material to make in embodiment 1 make as material of main part.
Embodiment
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 monomer A, monomers B are all bought and are obtained from the market.
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 bipolarity carrier transport ability, makes hole and electric transmission balance in luminescent layer; Also have higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, therefore organic semiconductor material of the present invention has bipolarity blue emitting phosphor material of main part.
The preparation method who the invention provides a kind of organic semiconductor material, comprises the steps:
Compd A is provided:
and compd B:
under inert atmosphere, first compd A is dissolved in organic solvent, then compd B, mineral alkali and catalyzer are added in reactant and at 70~120 DEG C, reacted 6~15 hours, the mol ratio of described compd A and compd B is 1:2~1:2.4, and it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
In specifically having implemented, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: using stopped reaction obtain organic semiconductor material adopt normal hexane as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
In specific embodiment, vacuum drying condition is to be dried 12~24 hours at 50~70 DEG C;
In specific embodiment, described organic solvent is selected from least one in tetrahydrofuran (THF) (THF), acetonitrile (MeCN), toluene (Tol) and DMF (DMF).
In specific embodiment, 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.
In specific embodiment, described copper (Cu) powder, cuprous iodide (CuI) or Red copper oxide (Cu
2o).
In specific embodiment, the mol ratio of described catalyzer and described compd A is 1:10~1:5.
Adopted better simply synthetic route, thereby reduced 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, and wherein material of main part is organic semiconductor material as follows:
guest materials is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
In specific embodiment, the mass percent of described guest materials and described material of main part is 5%~15%.
In specific embodiment, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
Organic luminescent device transmitting blue light based on this material, and luminous efficiency is high.
Embodiment 1:
9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, the preparation process preparation process of 3'-bis-carbazoles is as follows:
Under nitrogen protection; by 9H; 9'H-3,3'-bis-carbazoles (26.6g, 80mmol) are dissolved in 200mL N; in dinethylformamide (DMF) solution; then add (4-bromophenyl) diphenylphosphine oxygen (57.0g, 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, filter, with distilling washing solid three times, obtain product 9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3,3'-bis-carbazoles, then adopt leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid under vacuum.Productive rate is 82%.
Test data of experiment: mass spectrum: m/z884.3(M
++ 1); Ultimate analysis (%) C
60h
42n
4o
2p
2: theoretical value: C81.43, H4.78, N3.17, O3.62, P7.00; Measured value: C81.51, H4.73, N3.10, O3.75, P7.06..
Be the thermogravimetic analysis (TGA) figure of the organic semiconductor material prepared of the present embodiment referring to accompanying drawing 1, thermogravimetric curve (TGA) test is carried out on Perkin-Elmer Series7, and under nitrogen gas stream protection, heat-up rate is 10K/min.5% thermal weight loss temperature is 438 DEG C as seen from the figure.
By test for low temperature phosphorescence spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate its triplet state emission characteristic.Under the liquid nitrogen of 77K, bill of material reveals very strong blue emitting phosphor transmitting, and emission peak is at 428nm, and corresponding triplet energy state is 2.90eV, the triplet energy state (2.62eV) that is much higher than phosphor material FIrpic, test data result shows that our material can be used as blue phosphorescent material of main part.
Embodiment 2:
9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, the preparation process preparation process of 3'-bis-carbazoles is as follows:
Under nitrogen protection; by 9H; 9'H-3,3'-bis-carbazoles (26.6g, 80mmol) are dissolved in 200mL toluene (Tol) solution; then add (4-bromophenyl) diphenylphosphine oxygen (62.7g; 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, filter, with distilling washing solid three times, obtain product 9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3,3'-bis-carbazoles, then adopt leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid under vacuum.Productive rate is 82%.
Embodiment 3:
9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, the preparation process preparation process of 3'-bis-carbazoles is as follows:
Under nitrogen protection; by 9H; 9'H-3; 3'-bis-carbazoles (26.6g, 80mmol) are dissolved in 200mL acetonitrile (MeCN) solution, then add (4-bromophenyl) diphenylphosphine oxygen (68.4g; 192mmol); potassiumphosphate (39g, 184mmol) and Red copper oxide (2.3g, 16mmol).Reactant stirring reaction 12 hours at 90 DEG C.Stopped reaction is cooled to room temperature, filter, with distilling washing solid three times, obtain product 9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3,3'-bis-carbazoles, then adopt leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid under vacuum.Productive rate is 80%.
Embodiment 4:
9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, the preparation process preparation process of 3'-bis-carbazoles is as follows:
Under nitrogen protection; by 9H; 9'H-3; 3'-bis-carbazoles (26.6g, 80mmol) are dissolved in 200mL tetrahydrofuran (THF) (THF) solution, then add (4-bromophenyl) diphenylphosphine oxygen (65.5g; 184mmol); sodium carbonate (20.4g, 192mmol) and cuprous iodide (2.6g, 13.6mmol).Reactant stirring reaction 15 hours at 70 DEG C.Stopped reaction is cooled to room temperature, filter, with distilling washing solid three times, obtain product 9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3,3'-bis-carbazoles, then adopt leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid under vacuum.Productive rate is 80%.
Embodiment 5:
9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, the preparation process preparation process of 3'-bis-carbazoles is as follows:
Under nitrogen protection; by 9H; 9'H-3,3'-bis-carbazoles (26.6g, 80mmol) are dissolved in 200mL N; in dinethylformamide (DMF) solution; then add (4-bromophenyl) diphenylphosphine oxygen (59.8g, 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, filter, with distilling washing solid three times, obtain product 9,9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3,3'-bis-carbazoles, then adopt leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid under vacuum.Productive rate is 82%.
Application Example
Organic electroluminescence device 300, as Fig. 2, it comprises substrate 301 to its structure, anode 302, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electronic injection buffer layer 307, negative electrode 308.
In the present embodiment, the material of substrate 301 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, electronic injection buffer layer 307, negative electrode 308, it is the tin indium oxide of 10~20 Ω/ that anode 302 adopts square resistance, 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 materials adopt the invention process 1 to prepare, 9'-bis-(4-(diphenyl phosphine oxygen base) phenyl)-9H, 9'H-3, 3'-bis-carbazoles, and taking material of main part as benchmark the object luminescent material two (4 of doping mass percent as 7%, 6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (III), luminescent layer 305 thickness are 20nm, electron transfer layer 306 adopts 4, 7-phenylbenzene-1, 10-phenanthroline, thickness is 30nm, electronic injection buffer layer 307 adopts lithium fluoride, thickness is 1nm, negative electrode 308 adopts metallic aluminium, thickness is 100nm.
Organic layer and metal level all adopt thermal evaporation process deposits to complete, and vacuum tightness is 10
-3~10
-5pa, the thickness of film adopts film thickness monitoring instrument to monitor, and 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 luminous field such as blueness or white.Electric current-the brightness-voltage characteristic of device is that all measurements that completed by the Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) with correction silicon photoelectric diode all complete in atmosphere at room temperature.Result shows: the trigger voltage of device is 2.9V, at 1000cd/m
2brightness under, luminous efficiency is 7.8lm/W.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore 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 inert atmosphere, first compd A is dissolved in organic solvent, then compd B, mineral alkali and catalyzer are added in reactant and at 70~120 DEG C, reacted 6~15 hours, the mol ratio of described compd A and compd B is 1:2~1:2.4, and it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
3. preparation method as claimed in claim 2, it is characterized in that, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: using stopped reaction obtain organic semiconductor material adopt normal hexane solvent as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
4. preparation method as claimed in claim 2, is characterized in that, described organic solvent is selected from least one in tetrahydrofuran (THF), acetonitrile, toluene and DMF.
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, is characterized in that, described catalyzer is copper powder, cuprous iodide or Red copper oxide.
7. preparation method as claimed in claim 2, 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, and wherein material of main part is organic semiconductor material as follows:
guest materials is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
9. electroluminescent device as claimed in claim 8, is characterized in that, the mass percent of described material of main part and described guest materials is 5%~15%.
10. electroluminescent device as claimed in claim 8, 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.
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CN110204574A (en) * | 2019-06-27 | 2019-09-06 | 武汉华星光电半导体显示技术有限公司 | Bipolar host material and preparation method thereof, electroluminescent device and preparation method thereof |
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JP2011190239A (en) * | 2010-02-17 | 2011-09-29 | Chemiprokasei Kaisha Ltd | New bicarbazolyl derivative, host material comprising the same, and organic electroluminescent element using the same |
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2013
- 2013-04-25 CN CN201310147682.4A patent/CN104119383A/en active Pending
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JP2011190239A (en) * | 2010-02-17 | 2011-09-29 | Chemiprokasei Kaisha Ltd | New bicarbazolyl derivative, host material comprising the same, and organic electroluminescent element using the same |
Non-Patent Citations (1)
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HISAHIRO SASABE ET AL.: "3,3’-Bicarbazole-Based Host Materials for High-Efficiency Blue Phosphorescent OLEDs with Extremely Low Driving Voltage", 《ADV. MATER.》 * |
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CN110204574A (en) * | 2019-06-27 | 2019-09-06 | 武汉华星光电半导体显示技术有限公司 | Bipolar host material and preparation method thereof, electroluminescent device and preparation method thereof |
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Application publication date: 20141029 |