CN104262282A - Blue light semiconductor material containing indenophenoxazine, preparation method of blue light semiconductor material, and organic luminescent device made of blue light semiconductor material - Google Patents
Blue light semiconductor material containing indenophenoxazine, preparation method of blue light semiconductor material, and organic luminescent device made of blue light semiconductor material Download PDFInfo
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- 0 *c1cccc(*)c1 Chemical compound *c1cccc(*)c1 0.000 description 1
- DLXLZFKLHDWLGG-UHFFFAOYSA-N Nc(cc1c2c3cccc2C=C1)c3Oc1ccccc1Br Chemical compound Nc(cc1c2c3cccc2C=C1)c3Oc1ccccc1Br DLXLZFKLHDWLGG-UHFFFAOYSA-N 0.000 description 1
- PJRZXHZMAKYCCN-UHFFFAOYSA-N O=C(c1cc(C=CCC2)c2cc1)OC(c1cc(cccc2)c2cc1)=O Chemical compound O=C(c1cc(C=CCC2)c2cc1)OC(c1cc(cccc2)c2cc1)=O PJRZXHZMAKYCCN-UHFFFAOYSA-N 0.000 description 1
- BBIOXNBRSNVNLM-UHFFFAOYSA-N O=C(c1cc2ccccc2cc1)N1c2c(cccc3C=C4)c3c4cc2Oc2ccccc12 Chemical compound O=C(c1cc2ccccc2cc1)N1c2c(cccc3C=C4)c3c4cc2Oc2ccccc12 BBIOXNBRSNVNLM-UHFFFAOYSA-N 0.000 description 1
- UAPLYKYZBBBFQP-UHFFFAOYSA-N O=C(c1ccc(cccc2)c2c1)Nc(cc1c2c3cccc2C=C1)c3Oc(cccc1)c1Br Chemical compound O=C(c1ccc(cccc2)c2c1)Nc(cc1c2c3cccc2C=C1)c3Oc(cccc1)c1Br UAPLYKYZBBBFQP-UHFFFAOYSA-N 0.000 description 1
- JKXWWYRGEGSRDB-UHFFFAOYSA-N [O-][N+](c1cc(C=Cc2ccc3)c2c3c1I)=O Chemical compound [O-][N+](c1cc(C=Cc2ccc3)c2c3c1I)=O JKXWWYRGEGSRDB-UHFFFAOYSA-N 0.000 description 1
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- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
The invention relates to a blue light semiconductor material containing indenophenoxazine, a preparation method of the blue light semiconductor material, and an organic luminescent device made of the blue light semiconductor material, for solving the technical problems that an existing EL device which is made of a polymer and emits blue light is low in color purity, high in driving voltage and low in efficiency. The blue light semiconductor material containing indenophenoxazine is prepared by reacting 2-bromo-phenol and 1-iodine-2-nitro acenaphthene as raw materials to generate 5-(2-bromophenoxy)-4-acenaphthenyl amino; further reacting with acid anhydride with an R substituted group to generate N-(5-(2-bromophenoxy)-4-acenaphthenyl)-4-benzyl formamide; and continuously performing cyclization reaction. The prepared material is high in light emitting efficiency, so that the compound can be used as a light emitting material or a light emitting main body material, particularly can be used as a phosphorescence blue light main body material and has the advantages of high efficiency, high brightness, short service life and relatively low manufacturing cost when being used in organic electroluminescent devices, and the manufacturing cost of the organic electroluminescent devices is lowered.
Description
Technical field
The present invention relates to organic photoelectrical material field, particularly a kind of organic luminescent device containing blue-light semiconductor material of indeno Phenazoxine and preparation method thereof and be made up of this material.
Background technology
Since the C.W.Tang of Eastman Kodak company has reported since each layer has multilayer organic field luminescence (EL) device of appointed function, because this device has lightweight, thin, that color is many, switching speed is fast and luminescent properties is high under low driving voltage advantage, last decade has carried out the much research about organic electroluminescenoe device.Due to these effort, its performance obtains significant improvement within short duration: balance electric charge input by multilayered structure, by adding additive adjustable colors and improving quantum yield, etc.Also find that the novel electrode be made up of alloy can be used for organic luminescent device in addition.
This organic electroluminescenoe device can be classified according to the molecular weight of device material and manufacturing processed: the device manufactured with low-molecular weight compound and the device manufactured with macromolecule compound.Low-molecular weight compound easily can be purified to high purity by vacuum deposition layering.And, easily obtain colored pixels in lower molecular weight device.Although lower molecular weight organic electroluminescenoe device has these advantages, in actual applications, still await perfect further in such as quantum yield and in purity of color, and need to prevent lamellar crystalline.About the electroluminescent display of this use low-molecular weight compound has carried out various research actively, particularly in Japan and the U.S., first the such as Idemitsu-Kosan company limited of Japan put on display in 1997 and a kind ofly uses 10 of color changing media inches of panchromatic organic electroluminescence displays.The Pioneer Corporation of Japan illustrates a kind of 5 inches of panchromatic organic electroluminescence displays of passive substrate (PM).Recently, Pioneer Corporation and Motorola Inc.Sign about the agreement of batch production with the mobile telephone of organic electroluminescence display, this means that lower molecular weight electroluminescent display can appear on the market in the recent period.
The pi-conjugated alternating structure with singly-bound (σ-key) and double-strand (π-key), wherein π-electronics is uniformly distributed so that can moves freely in polymer chain.Therefore, pi-conjugated have semiconductive characteristic and by appropriate molecular designing, when described pi-conjugated be applied to the emission layer of luminescent device time, the light of the visible range can be with corresponding to HOMO-LUMO can be radiated.Can also form thin layer is present in the product of electroluminescent device, easily carries out spin coating or printing, and cost is low and have high glass transition temperature, this mechanical property good for thin layer provides.The El element of blue light-emitting is used to have the problems such as purity of color is low, driving voltage is high, efficiency is low.In order to solve these problems of El element, there has been active research, but still existing can improvements.
Summary of the invention
The El element that the present invention will solve the blue light-emitting of polymkeric substance in prior art has that purity of color is low, driving voltage is high, inefficient technical problem, the organic luminescent device providing a kind of blue-light semiconductor material containing indeno Phenazoxine and preparation method thereof and be made up of this material.
In order to solve the problems of the technologies described above, technical scheme of the present invention is specific as follows:
Containing a blue-light semiconductor material for indeno Phenazoxine, the structure expression of this material is:
In formula (I), R is phenyl, p-methylphenyl or naphthyl.
Containing a preparation method for the blue-light semiconductor material of indeno Phenazoxine, comprise the steps:
Step S1: add 2-bromophenol, 1-iodo-2-nitro acenaphthene and salt of wormwood in the reaction vessel after degassed, and by dissolution with solvents, fully generate 5-(2-bromine phenoxy group)-4-acenaphthenyl amine after reaction;
Step S2: above-mentioned 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and the anhydride reaction rolled into a ball containing R substituent are generated N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide;
Step S3: continue cyclization reaction and generate the blue-light semiconductor material containing indeno Phenazoxine.
In technique scheme, described step S1 is specially:
2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood is added in the reaction vessel after degassed, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, after being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.
In technique scheme, described step S2 is specially:
The acid anhydrides containing R substituent group of 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide.
In technique scheme, described step S3 is specially:
N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide and 2mmol salt of wormwood are added in reactor; under nitrogen protection; N is added by syringe; N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL; stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter; concentrated solution, obtains the blue-light semiconductor material containing indeno Phenazoxine by column chromatography.
A kind of by the described organic luminescent device made containing the blue-light semiconductor material of indeno Phenazoxine, it comprises the first electrode, the second electrode and is placed in the one or more organic compound layers between described first electrode, described second electrode, it is characterized in that, organic compound layer described at least one comprises the described blue-light semiconductor material containing indeno Phenazoxine.
A kind of blue-light semiconductor material containing indeno Phenazoxine provided by the invention and preparation method thereof and the beneficial effect of organic luminescent device be made up of this material are:
A kind of blue-light semiconductor material containing indeno Phenazoxine provided by the invention has hole, electron transfer rate relatively preferably, indeno Phenazoxine analog derivative has large conjugate planes structure thus can provide high electron mobility, therefore this compound has higher electronic transmission performance, good film-forming property, at room temperature have good stability, the device applied also has higher stability.
Blue-light semiconductor material containing indeno Phenazoxine of the present invention has high luminous efficiency, high luminous efficiency shows that this compound can be used as luminescent material or light emitting host material, especially can as the blue material of main part of phosphorescence, for showing high-level efficiency, high brightness, long lifetime in organic electroluminescence device, there is the advantage that manufacturing cost is lower, reduce the manufacturing cost of organic electroluminescence device.
Embodiment
A kind of blue-light semiconductor material containing indeno Phenazoxine provided by the invention is for raw material reaction generates 5-(2-bromine phenoxy group)-4-acenaphthenyl amine with 2-bromophenol and 1-iodo-2-nitro acenaphthene; Again 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and the anhydride reaction rolled into a ball containing R substituent are generated N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide; Continue cyclization reaction and generate the blue-light semiconductor material containing indeno Phenazoxine.Concrete synthetic route is as follows:
A kind of preparation method of the blue-light semiconductor material containing indeno Phenazoxine is specially:
Step S1: add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood in the reaction vessel after degassed, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, after being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.
Step S2: the acid anhydrides containing R substituent group of 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide.
Step S3: N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide and 2mmol salt of wormwood are added in reactor; under nitrogen protection; N is added by syringe; N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL; stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter; concentrated solution, obtains the blue-light semiconductor material containing indeno Phenazoxine by column chromatography.
Embodiment 1:
In the reaction vessel after degassed, add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C.After being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.Mass spectrum: calculated value is 338.20; Test value is 338.18.Ultimate analysis: calculated value is C:63.92; H:3.58; Br:23.63; N:4.14; O:4.73; Test value is C:63.91; H:3.56; Br:23.64; N:4.15; O:4.75.
By 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and the mixing of 5mmol benzoyl oxide, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5-(2-bromine phenoxy group)-4-acenaphthenyl) benzamide.Mass spectrum: calculated value is 442.30; Test value is 442.32.Ultimate analysis: calculated value is C:67.89; H:3.65; Br:18.07; N:3.17; O:7.23; Test value is C:67.86; H:3.67; Br:18.05; N:3.19; O:7.24.
N-(5-(2-bromine phenoxy group)-4-acenaphthenyl) benzamide and 2mmol salt of wormwood are added in reactor, under nitrogen protection, adds N by syringe, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL.Stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter, concentrated solution, obtains target compound (12H-indeno [7,1-AB] Phenazoxine-12-base) (phenyl) ketone by column chromatography.Mass spectrum: calculated value is 361.39; Test value is 361.37.Ultimate analysis: calculated value is C:83.09; H:4.18; N:3.88; O:8.85; Test value is C:83.07; H:4.19; N:3.87; O:8.87; .
Embodiment 2:
In the reaction vessel after degassed, add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C.After being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.Mass spectrum: calculated value is 338.20; Test value is 338.18.Ultimate analysis: calculated value is C:63.92; H:3.58; Br:23.63; N:4.14; O:4.73; Test value is C:63.91; H:3.56; Br:23.64; N:4.15; O:4.75.
The 4-methyl benzoic anhydride of 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide.Mass spectrum: calculated value is 456.33; Test value is 456.34.Ultimate analysis: calculated value is C:68.43; H:3.98; Br:17.51; N:3.07; O:7.01; Test value is C:68.41; H:3.97; Br:17.52; N:3.09; O:7.00.
N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide and 2mmol salt of wormwood are added in reactor, under nitrogen protection, adds N by syringe, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL.Stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter, concentrated solution, obtains target compound (12H-indeno [7,1-AB] Phenazoxine-12-base)-(p-methylphenyl) ketone by column chromatography.Mass spectrum: calculated value is 375.42; Test value is 375.40.Ultimate analysis: calculated value is C:83.18; H:4.56; N:3.73; O:8.52; Test value is C:83.16; H:4.54; N:3.75; O:8.54.
Embodiment 3:
In the reaction vessel after degassed, add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C.After being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.Mass spectrum: calculated value is 338.20; Test value is 338.18.Ultimate analysis: calculated value is C:63.92; H:3.58; Br:23.63; N:4.14; O:4.73; Test value is C:63.91; H:3.56; Br:23.64; N:4.15; O:4.75.
The 2-naphthalene acid anhydride of 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5 (2-bromine phenoxy group)-4-acenaphthenyl)-2-naphthoamide.Mass spectrum: calculated value is 492.36; Test value is 492.34.Ultimate analysis: calculated value is C:70.74; H:3.68; Br:16.23; N:2.84; O:6.50; Test value is C:70.76; H:3.67; Br:16.24; N:2.85; O:6.47.
N-(5 (2-bromine phenoxy group)-4-acenaphthenyl)-2-naphthoamide and 2mmol salt of wormwood are added in reactor, under nitrogen protection, adds N by syringe, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL.Stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter, concentrated solution, obtains target compound (12H-indeno [7,1-AB] Phenazoxine-12-base) (2-naphthyl) ketone by column chromatography.Mass spectrum: calculated value is 411.45; Test value is 411.47.Ultimate analysis: calculated value is C:84.65; H:4.16; N:3.40; O:7.78; Test value is C:84.63; H:4.17; N:3.42; O:7.77.
The above embodiment only have expressed embodiments 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.
Comparative example:
Using the compound of chemical formula a as light emitting host material, the compound of chemical formula b is as dopant material, the 2-TNATA (4 that chemical formula c represents, 4, 4-tri-(N-naphthyl)-N-phenyl amino)-triphenylamine) as hole-injecting material, α-NPD (the N that chemical formula d represents, N '-two (naphthyl)-N, N '-diphenylbenzidine) as hole mobile material, make the organic luminescent device of structure below: the compound (30nm of the compound+chemical formula b of ITO/2-TNATA (80nm)/α-NPD (30nm)/chemical formula a, wherein b content is 8%)/Alq
3(30nm)/LiF (0.5nm)/Al (60nm).Wherein, Alq
3oxine aluminium.
By Corning (healthy and free from worry) society 15 Ω/cm
2(1000) ito glass substrate is cut into the size of 50mm*50mm*0.7mm.Subsequently in microwave, successively at acetone, Virahol, cleans 15 minutes in pure water respectively, in ultraviolet, clean 30 minutes again.At the 2-TNATA of thereon vacuum evaporation 80nm thickness, form hole injection layer.Above hole injection layer, the α-NPD of vacuum evaporation 30nm thickness, defines hole transporting layer.The compound that above hole transporting layer, the chemical formula a of vacuum evaporation 30nm thickness represents and the compound that chemical formula b represents (doping rate 8%), define luminescent layer.The Alq of vacuum evaporation 30nm thickness above luminescent layer
3, define electron supplying layer.Vacuum evaporation LiF 0.5nm (electron injection) and Al 60nm successively above electron supplying layer, has made organic luminescent device.In the preparation embodiment of this comparative example and following organic luminescent device, the EL evaporator adopting DOV company to manufacture carries out vacuum evaporation.
The preparation embodiment of organic luminescent device:
Adopt as the method in comparative example, make the organic luminescent device with structure below, difference is as luminescent layer compound, what replace the compound of chemical formula a to adopt is compound prepared by above-described embodiment 1,2 or 3: the compound of ITO/2-TNATA (80nm)/α-NPD (30nm)/formula (I) compound+chemical formula b] (25nm, wherein b content is 8.0%)/Alq
3(30nm) organic luminescent device of the structure of/LiF (0.5nm)/Al (60nm).
Measure embodiment: the luminescent properties of the preparation embodiment sample of comparative example's sample and organic luminescent device:
Under similarity condition, measure the sample of comparative example and the preparation embodiment sample of organic luminescent device.Measure and adopt KEITHLEY Keithley 235 type source measuring unit, SpectrascanPR650 spectral scan colourimeter, to evaluate driving voltage, luminosity, luminous efficiency, glow color.The results are shown in Table 1:
Table 1
Known according to table 1, above-mentioned sample shows glow color for blue in 460-480nm wavelength region.The sample of preparation embodiment of organic luminescent device compares with the sample of comparative example, uses the derivative of indeno Phenazoxine can have the efficiency of lower driving voltage, higher brightness and Geng Gao as the organic luminescent device of organic layer.
Obviously, above-described embodiment is only for clearly example being described, and the restriction not to embodiment.For those of ordinary skill in the field, can also make other changes in different forms on the basis of the above description.Here exhaustive without the need to also giving all embodiments.And thus the apparent change of extending out or variation be still among the protection domain of the invention.
Claims (6)
1., containing a blue-light semiconductor material for indeno Phenazoxine, it is characterized in that, the structure expression of this material is:
In formula (I), R is phenyl, p-methylphenyl or naphthyl.
2. the preparation method of the blue-light semiconductor material containing indeno Phenazoxine according to claim 1, is characterized in that, comprise the steps:
Step S1: add 2-bromophenol, 1-iodo-2-nitro acenaphthene and salt of wormwood in the reaction vessel after degassed, and by dissolution with solvents, fully generate 5-(2-bromine phenoxy group)-4-acenaphthenyl amine after reaction;
Step S2: above-mentioned 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and the anhydride reaction rolled into a ball containing R substituent are generated N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide;
Step S3: continue cyclization reaction and generate the blue-light semiconductor material containing indeno Phenazoxine.
3. the preparation method of the blue-light semiconductor material containing indeno Phenazoxine according to claim 2, it is characterized in that, described step S1 is specially:
2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and 2mmol salt of wormwood is added in the reaction vessel after degassed, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, after being cooled to room temperature, add large water gaging, be extracted with ethyl acetate three times, after organic phase washes three times, concentrate drying obtains 5-(2-bromine phenoxy group)-4-acenaphthenyl amine.
4. the preparation method of the blue-light semiconductor material containing indeno Phenazoxine according to claim 2, it is characterized in that, described step S2 is specially:
The acid anhydrides containing R substituent group of 5-(2-bromine phenoxy group)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, be extracted with ethyl acetate, organic phase anhydrous sodium sulfate drying, after concentrated, column chromatography obtains N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide.
5. the preparation method of the blue-light semiconductor material containing indeno Phenazoxine according to claim 2, it is characterized in that, described step S3 is specially:
N-(5-(2-bromine phenoxy group)-4-acenaphthenyl)-4-phenmethyl methane amide and 2mmol salt of wormwood are added in reactor; under nitrogen protection; N is added by syringe; N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL; stir 24 hours at 135 DEG C, dissolve with methylene dichloride after reaction solution is cooled to room temperature, filter; concentrated solution, obtains the blue-light semiconductor material containing indeno Phenazoxine by column chromatography.
6. by the organic luminescent device made containing the blue-light semiconductor material of indeno Phenazoxine according to claim 1, it comprises the first electrode, the second electrode and is placed in the one or more organic compound layers between described first electrode, described second electrode, it is characterized in that, organic compound layer described at least one comprises the described blue-light semiconductor material containing indeno Phenazoxine.
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Citations (3)
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|---|---|---|---|---|
| US20110063485A1 (en) * | 2009-09-11 | 2011-03-17 | Fujifilm Corporation | Photoelectric conversion device, production method thereof, photosensor, imaging device and their drive methods |
| CN103805167A (en) * | 2012-11-14 | 2014-05-21 | 吉林奥来德光电材料股份有限公司 | Organic blue luminescent material, and preparation method and application thereof |
| CN103889952A (en) * | 2011-10-20 | 2014-06-25 | 默克专利有限公司 | Materials for organic electroluminescent devices |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110063485A1 (en) * | 2009-09-11 | 2011-03-17 | Fujifilm Corporation | Photoelectric conversion device, production method thereof, photosensor, imaging device and their drive methods |
| CN102024907A (en) * | 2009-09-11 | 2011-04-20 | 富士胶片株式会社 | Photoelectric conversion device, production method thereof, photosensor, imaging device and their drive methods |
| CN103889952A (en) * | 2011-10-20 | 2014-06-25 | 默克专利有限公司 | Materials for organic electroluminescent devices |
| CN103805167A (en) * | 2012-11-14 | 2014-05-21 | 吉林奥来德光电材料股份有限公司 | Organic blue luminescent material, and preparation method and application thereof |
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