CN104119327A - Organic semiconductor material, preparation method and electroluminescent device - Google Patents

Organic semiconductor material, preparation method and electroluminescent device Download PDF

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Publication number
CN104119327A
CN104119327A CN201310148270.2A CN201310148270A CN104119327A CN 104119327 A CN104119327 A CN 104119327A CN 201310148270 A CN201310148270 A CN 201310148270A CN 104119327 A CN104119327 A CN 104119327A
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China
Prior art keywords
organic semiconductor
semiconductor material
compd
preparation
pyridine
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CN201310148270.2A
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Inventor
周明杰
张振华
王平
黄辉
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Priority to CN201310148270.2A priority Critical patent/CN104119327A/en
Publication of CN104119327A publication Critical patent/CN104119327A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • 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

Abstract

The invention provides an organic semiconductor material, which has a chemical formula shown as the following. The organic semiconductor material has a phosphorescence host material with a bipolar carrier transport ability, and at the same time has the hole transport property and electron transport property, and enables balanced hole and electron transport in a luminescent layer, greatly improves the luminescent efficiency, and has high thermal stability and high triplet state energy level. The invention also 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 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 the phosphorescent light body material of bipolarity carrier transport ability, there is hole transport character and electronic transport property simultaneously, make the transmission balance in hole and electronics in luminescent layer, greatly improve luminous efficiency, and have higher thermostability and higher triplet, 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 the organic solvent that contains compd A 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] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close 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%～20%.
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: the phosphorescent light body material with bipolarity carrier transport ability, there is hole transport character and electronic transport property simultaneously, make the transmission balance in hole and electronics in luminescent layer, greatly improve luminous efficiency, and have higher thermostability and higher triplet, synthetic method is simple, can be used for blue emitting phosphor material of main part.
Brief description of the drawings
The structural representation of Fig. 1 organic electroluminescence device that to be organic semiconductor material to make in embodiment 1 make as material of main part;
Fig. 2 is the organic electroluminescence device efficiency-brightness curve taking compound of the present invention as material of main part.
Fig. 3 is the thermogravimetic analysis (TGA) figure of the organic semiconductor material that makes in embodiment 1.
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 the phosphorescent light body material of bipolarity carrier transport ability, there is hole transport character and electronic transport property simultaneously, make the transmission balance in hole and electronics in luminescent layer, greatly improve luminous efficiency, and have higher thermostability and higher triplet, 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 the organic solvent that contains compd A 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] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close 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).
In specific embodiment, the mass percent of described guest materials and described material of main part is 5%～20%.
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:
2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3, the preparation process preparation process of 4-oxadiazole is as follows:
Under nitrogen protection; by 2,5-bis-(3-bromophenyl)-1,3; 4-oxadiazole (30.4g; 80mmol) be dissolved in 200mL DMF (DMF) solution, then add carbazole (26.7g; 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 2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3,4-oxadiazole, 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 85%.
Test data of experiment: mass spectrum m/z552.2(M ++ 1); Ultimate analysis (%) C 38h 24n 4o: theoretical value: C82.59, H4.38, N10.14, O2.90; Measured value: C82.64, H4.30, N10.16, O2.81.
Are thermogravimetic analysis (TGA) figure of the organic semiconductor material prepared of the present embodiment referring to accompanying drawing 3, 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 381 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, emission peak is at 449nm, corresponding triplet energy state is 2.76eV, be much higher than the triplet energy state (2.62eV) of phosphor material FIrpic, test data result shows that our material can be used as bipolarity blue phosphorescent material of main part.
Embodiment 2:
2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3, the preparation process preparation process of 4-oxadiazole is as follows:
Under nitrogen protection; by 2,5-bis-(3-bromophenyl)-1,3; 4-oxadiazole (30.4g; 80mmol) be dissolved in 200mL toluene (Tol) solution, then add carbazole (29.4g, 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, filter, with distilling washing solid three times, obtain product 2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3,4-oxadiazole, 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 3:
2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3, the preparation process preparation process of 4-oxadiazole is as follows:
Under nitrogen protection; by 2; 5-bis-(3-bromophenyl)-1,3,4-oxadiazole (30.4g; 80mmol) be dissolved in 200mL acetonitrile (MeCN) solution; then add carbazole (32.1g, 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 2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3,4-oxadiazole, 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 86%.
Embodiment 4:
2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3, the preparation process preparation process of 4-oxadiazole is as follows:
Under nitrogen protection; by 2; 5-bis-(3-bromophenyl)-1,3,4-oxadiazole (30.4g; 80mmol) be dissolved in 200mL tetrahydrofuran (THF) (THF) solution; then add carbazole (30.7g, 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 2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3,4-oxadiazole, 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 90%.
Embodiment 5:
2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3, the preparation process preparation process of 4-oxadiazole is as follows:
Under nitrogen protection; by 2,5-bis-(3-bromophenyl)-1,3; 4-oxadiazole (30.4g; 80mmol) be dissolved in 200mL DMF (DMF) solution, then add carbazole (28.1g; 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 2,5-bis-(3-(9H-carbazole-9-yl) phenyl)-1,3,4-oxadiazole, 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 79%.
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, 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 2 that luminescent layer 305 main body luminescent materials adopt the invention process 1 to prepare, 5-bis-(3-(9H-carbazole-9-yl) phenyl)-1, 3, 4-oxadiazole, and taking material of main part as benchmark the object luminescent material two [3 of doping mass percent as 15%, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-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.Test result demonstration, as shown in Figure 2, the maximum current efficiency of this organic electroluminescence device is 9.2cd/A, high-high brightness is 24710cd/m 2.Result shows that polymer body material property of the present invention is better, is a kind of very promising Blue-light emitting host material.
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 the organic solvent that contains compd A 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] close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) close 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, is characterized in that, the mass percent of described material of main part and described guest materials is 5%～20%.
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.
CN201310148270.2A 2013-04-25 2013-04-25 Organic semiconductor material, preparation method and electroluminescent device Pending CN104119327A (en)

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CN111484486A (en) * 2019-04-26 2020-08-04 广东聚华印刷显示技术有限公司 Organic compound and organic light emitting diode
CN114751900A (en) * 2022-04-24 2022-07-15 南京邮电大学 D-A type organic luminescent material and preparation method and application thereof

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Cited By (6)

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CN114751900A (en) * 2022-04-24 2022-07-15 南京邮电大学 D-A type organic luminescent material and preparation method and application thereof
CN114751900B (en) * 2022-04-24 2023-09-12 南京邮电大学 D-A type organic luminescent material and preparation method and application thereof

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Application publication date: 20141029