CN104262282B - Blue-light semiconductor material containing indeno phenoxazine and preparation method thereof and the organic luminescent device being made up of this material - Google Patents
Blue-light semiconductor material containing indeno phenoxazine and preparation method thereof and the organic luminescent device being made up of this material Download PDFInfo
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- CN104262282B CN104262282B CN201410439791.8A CN201410439791A CN104262282B CN 104262282 B CN104262282 B CN 104262282B CN 201410439791 A CN201410439791 A CN 201410439791A CN 104262282 B CN104262282 B CN 104262282B
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
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Abstract
The present invention relates to a kind of blue-light semiconductor material containing indeno phenoxazine and preparation method thereof and the organic luminescent device being made up of this material.The El element of the blue light-emitting solving existing polymer has that excitation is low, driving voltage is high, inefficient technical problem.Blue-light semiconductor material containing indeno phenoxazine is to generate 5 (2 bromobenzene epoxide) 4 acenaphthenyl amine with 2 bromophenols and 1 iodine 2 nitro acenaphthene for raw material reaction；N (5 (2 bromobenzene epoxide) 4 acenaphthenyls) 4 benzyl Methanamides are generated again with the anhydride reaction rolled into a ball containing R substituent；Continue cyclization reaction to prepare.The material prepared has high luminous efficiency, show that this compound can be as luminescent material or light emitting host material, especially can be as phosphorescence blueness material of main part, high efficiency, high brightness, long-life is shown in organic electroluminescence device, there is the advantage that manufacturing cost is relatively low, reduce the manufacturing cost of organic electroluminescence device.
Description
Technical field
The present invention relates to organic photoelectrical material field, particularly to a kind of blue-light semiconductor containing indeno phenoxazine
Material and preparation method thereof and the organic luminescent device being made up of this material.
Background technology
Since the C.W.Tang of Eastman Kodak Company report each layer have specify function multilamellar organic
Since electroluminescent (EL) device, due to this device have lightweight, thin, color is many, conversion speed is fast and
The advantage that luminescent properties is high under low driving voltage, last decade has been carried out many about organic field cause
The research of optical device.Due to these effort, its performance has obtained significant improvement in the short term: pass through multilamellar
Constitutional balance electric charge input, by adding additive regulation color and improving quantum efficiency, etc..Additionally
Also find that the novel electrode being made up of alloy can be used for organic luminescent device.
This organic electroluminescenoe device can be classified according to the molecular weight of device material and manufacture process: with low
Compound molecular weight manufacture device and with macromolecule compound manufacture device.Low molecular weight compound can
To be layered by vacuum deposition and to be easily purified to high-purity.And, low-molecular-weight device is readily available
Colored pixels.Although low-molecular-weight organic electroluminescenoe device has these advantages, in actual applications, exist
Such as quantum efficiency aspect and excitation aspect still await the most perfect, and it also requires prevent thin layer
Crystallization.Electroluminescent display about this use low molecular weight compound has carried out various the most actively
Research, particularly in Japan and the U.S., the such as Idemitsu-Kosan company limited of Japan is first in 1997
A kind of 10 inches of panchromatic organic electroluminescence displays using color changing media are first put on display.Japan
Pioneer Corporation illustrates a kind of 5 inches of panchromatic organic electroluminescence displays of passive substrate (PM).
Recently, Pioneer Corporation and Motorola Inc.Sign about batch production with organic field
The agreement of the mobile phone of electroluminescent display, it means that low-molecular-weight electroluminescent display in the recent period can face
City.
The pi-conjugated alternating structure with singly-bound (σ-key) and double-strand (π-key), wherein π-electronics is uniformly distributed so that can
To move freely in polymer chain.Therefore, pi-conjugated have semiconductive characteristic and by appropriate molecule
Design, when described pi-conjugated be applied to luminescent device emission layer time, it is possible to radiation corresponding to HOMO-LUMO
The light of the visible range that can carry.Thin layer can also be formed be present in the product of electroluminescent device, easily
Carrying out spin coating or printing, low cost and have high glass transition temperature, this provides good for thin layer
Mechanical performance.The El element using blue light-emitting has the problems such as excitation is low, driving voltage is high, efficiency is low.
In order to solve these problems of El element, there has been active research, however it remains can improvements.
Summary of the invention
The invention solves the problems that in prior art that the El element of the blue light-emitting of polymer has that excitation is low, drive electricity
Press technical problem high, inefficient, it is provided that a kind of blue-light semiconductor material containing indeno phenoxazine and preparation thereof
Method and the organic luminescent device being made up of this material.
In order to solve above-mentioned technical problem, technical scheme is specific as follows:
A kind of blue-light semiconductor material containing indeno phenoxazine, the structure expression of this material is:
In formula (I), R is phenyl, p-methylphenyl or naphthyl.
The preparation method of a kind of blue-light semiconductor material containing indeno phenoxazine, comprises the steps:
Step S1: add 2-bromophenol, 1-iodo-2-nitro acenaphthene and carbonic acid in the reaction vessel after degassing
Potassium, and dissolve with solvent, fully generate 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine after reaction；
Step S2: by raw with the anhydride reaction containing R substituent group for above-mentioned 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine
Become N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide；
Step S3: continue cyclization reaction and generate the blue-light semiconductor material containing indeno phenoxazine.
In technique scheme, described step S1 particularly as follows:
To degassing after reaction vessel in add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and
2mmol potassium carbonate, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, after being cooled to room temperature, add
Entering a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains 5-(2-bromobenzene oxygen
Base)-4-acenaphthenyl amine.
In technique scheme, described step S2 particularly as follows:
By 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine and the anhydride mixing containing R substituent group of 5mmol, it is stirred at room temperature
Overnight, mixture adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies anhydrous sodium sulfate is done
Dry, after concentration, column chromatography obtains N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide.
In technique scheme, described step S3 particularly as follows:
N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide and 2mmol potassium carbonate are added reactor
In, under nitrogen protection, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL by syringe,
135 DEG C are stirred 24 hours, and reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, and concentrates solution, logical
Cross column chromatography and obtain the blue-light semiconductor material containing indeno phenoxazine.
A kind of by the described organic luminescent device made containing the blue-light semiconductor material of indeno phenoxazine, it includes
First electrode, the second electrode and be placed between described first electrode, described second electrode one or more
Organic compound layer, it is characterised in that at least one described organic compound layer comprises the described phenoxazine Han indeno
The blue-light semiconductor material of piperazine.
A kind of blue-light semiconductor material containing indeno phenoxazine and preparation method thereof that the present invention provides and by this material
The organic luminescent device that material is made provides the benefit that:
The present invention provide a kind of blue-light semiconductor material containing indeno phenoxazine have relatively good hole,
Electron transfer rate, indeno phenoxazine analog derivative has big conjugate planes structure such that it is able to provide
High electron mobility, therefore this compound has a higher electronic transmission performance, good film-forming property,
Having preferable stability under room temperature, the device applied also has higher stability.
The blue-light semiconductor material containing indeno phenoxazine of the present invention has high luminous efficiency, high luminous effect
Rate shows that this compound can be as luminescent material or light emitting host material, especially can be as phosphorescent blue
Color material of main part, shows high efficiency, high brightness, long-life in organic electroluminescence device,
There is the advantage that manufacturing cost is relatively low, reduce the manufacturing cost of organic electroluminescence device.
Detailed description of the invention
A kind of blue-light semiconductor material containing indeno phenoxazine that the present invention provides is with 2-bromophenol and 1-
Iodo-2-nitro acenaphthene is that raw material reaction generates 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine；Again by 5-(2-bromobenzene epoxide)-4-
Acenaphthenyl amine generates N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl first with the anhydride reaction containing R substituent group
Amide；Continue cyclization reaction and generate the blue-light semiconductor material containing indeno phenoxazine.Concrete synthetic route is as follows:
A kind of preparation method of the blue-light semiconductor material containing indeno phenoxazine particularly as follows:
Step S1: add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene in the reaction vessel after degassing
1.0mmol and 2mmol potassium carbonate, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, be cooled to
After room temperature, adding a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains
5-(2-bromobenzene epoxide)-4-acenaphthenyl amine.
Step S2: by 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine and the anhydride mixing containing R substituent group of 5mmol,
Stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies is with anhydrous
Sodium sulfate is dried, and after concentration, column chromatography obtains N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide.
Step S3: N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide and 2mmol potassium carbonate are added
Enter in reactor, under nitrogen protection, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene by syringe
1mL, stirs 24 hours at 135 DEG C, and reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, concentrates
Solution, obtains the blue-light semiconductor material containing indeno phenoxazine by column chromatography.
Embodiment 1:
Reaction vessel after degassing adds 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol
With 2mmol potassium carbonate, and with 10mLDMSO dissolve, at 100 DEG C heat 15 hours.It is cooled to room temperature
After, adding a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains 5-(2-
Bromobenzene epoxide)-4-acenaphthenyl amine.Mass spectrum: value of calculation is 338.20；Test value is 338.18.Elementary analysis: meter
Calculation 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.
5-(2-bromobenzene epoxide)-4-acenaphthenyl amine and 5mmol benzoyl oxide are mixed, stirred overnight at room temperature, mixing
Thing adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies anhydrous sodium sulfate is dried, after concentration
Column chromatography obtains N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl) Benzoylamide.Mass spectrum: value of calculation is 442.30；Test value
It is 442.32.Elementary analysis: value of calculation 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-bromobenzene epoxide)-4-acenaphthenyl) Benzoylamide and 2mmol potassium carbonate are added in reactor, nitrogen
Under gas shielded, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL by syringe.At 135 DEG C
Stirring 24 hours, reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, concentrates solution, pass through post
Chromatography obtains target compound (12H-indeno [7,1-AB] phenoxazine-12-base) (phenyl) ketone.Mass spectrum: meter
Calculation value is 361.39；Test value is 361.37.Elementary analysis: value of calculation 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:
Reaction vessel after degassing adds 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol
With 2mmol potassium carbonate, and with 10mLDMSO dissolve, at 100 DEG C heat 15 hours.It is cooled to room temperature
After, adding a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains 5-(2-
Bromobenzene epoxide)-4-acenaphthenyl amine.Mass spectrum: value of calculation is 338.20；Test value is 338.18.Elementary analysis: meter
Calculation 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-bromobenzene epoxide)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature,
Mixture adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies anhydrous sodium sulfate is dried, dense
After contracting, column chromatography obtains N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide.Mass spectrum: value of calculation is
456.33；Test value is 456.34.Elementary analysis: value of calculation 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-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide and 2mmol potassium carbonate are added reactor
In, under nitrogen protection, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL by syringe.?
135 DEG C are stirred 24 hours, and reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, concentrates solution,
Target compound (12H-indeno [7,1-AB] phenoxazine-12-base)-(p-methylphenyl) is obtained by column chromatography
Ketone.Mass spectrum: value of calculation is 375.42；Test value is 375.40.Elementary analysis: value of calculation 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:
Reaction vessel after degassing adds 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol
With 2mmol potassium carbonate, and with 10mLDMSO dissolve, at 100 DEG C heat 15 hours.It is cooled to room temperature
After, adding a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains 5-(2-
Bromobenzene epoxide)-4-acenaphthenyl amine.Mass spectrum: value of calculation is 338.20；Test value is 338.18.Elementary analysis: meter
Calculation 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-bromobenzene epoxide)-4-acenaphthenyl amine and 5mmol is mixed, stirred overnight at room temperature, mixing
Thing adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies anhydrous sodium sulfate is dried, after concentration
Column chromatography obtains N-(5 (2-bromobenzene epoxide)-4-acenaphthenyl)-2-naphthalenecarboxamide.Mass spectrum: value of calculation is 492.36；
Test value is 492.34.Elementary analysis: value of calculation 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-bromobenzene epoxide)-4-acenaphthenyl)-2-naphthalenecarboxamide and 2mmol potassium carbonate are added reactor
In, under nitrogen protection, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL by syringe.?
135 DEG C are stirred 24 hours, and reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, concentrates solution,
Target compound (12H-indeno [7,1-AB] phenoxazine-12-base) (2-naphthyl) ketone is obtained by column chromatography.
Mass spectrum: value of calculation is 411.45；Test value is 411.47.Elementary analysis: value of calculation 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.
Embodiment described above only have expressed embodiments of the present invention, and it describes more concrete and detailed, but
Therefore the restriction to the scope of the claims of the present invention can not be interpreted as.It should be pointed out that, for this area
For those of ordinary skill, without departing from the inventive concept of the premise, it is also possible to make some deformation and change
Entering, these broadly fall into protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be with appended power
Profit requires to be as the criterion.
Comparative example:
Using the compound of chemical formula a as light emitting host material, the compound of chemical formula b is as doping
Material, 2-TNATA (4,4,4-tri-(N-naphthyl)-N-the phenyl amino)-triphenylamine that chemical formula c represents)
As hole-injecting material, α-NPD (N, N '-two (naphthyl)-N, N '-diphenyl connection that chemical formula d represents
Aniline) as hole mobile material, make the organic luminescent device of following structure:
The compound of the compound+chemical formula b of ITO/2-TNATA (80nm)/α-NPD (30nm)/chemical formula a
(30nm, wherein b content is 8%)/Alq3(30nm)/LiF(0.5nm)/Al(60nm).Wherein, Alq3
It is 8-hydroxyquinoline aluminum.
By Corning (healthy and free from worry) society 15 Ω/cm2 Ito glass substrate is cut into
The size of 50mm*50mm*0.7mm.Subsequently in microwave, successively at acetone, isopropanol, pure water
Middle clean respectively 15 minutes, clean again in ultraviolet 30 minutes.At thereon vacuum evaporation 80nm
The 2-TNATA of thickness, forms hole injection layer.Above hole injection layer, vacuum evaporation 30nm is thick
α-the NPD of degree, defines hole transporting layer.The change of vacuum evaporation 30nm thickness above hole transporting layer
Compound that formula a represents and the compound (doping rate 8%) that chemical formula b represents, define luminescence
Layer.The Alq of vacuum evaporation 30nm thickness above luminescent layer3, define electron supplying layer.Electronics is defeated
Send above layer vacuum evaporation LiF 0.5nm (electronics injection) and Al 60nm successively, make organic
Optical device.In the preparation embodiment of this comparative example and following organic luminescent device, use
The EL evaporator that DOV company manufactures carries out vacuum evaporation.
The preparation embodiment of organic luminescent device:
Use such as the method in comparative example, make the organic luminescent device with following structure, no
It is, as luminescent layer compound, to replace the compound of chemical formula a to use above-mentioned enforcement with part
The compound of example 1,2 or 3 preparation: ITO/2-TNATA (80nm)/α-NPD (30nm)/formula (I) is changed
The compound of compound+chemical formula b] (25nm, wherein b content is 8.0%)
/Alq3(30nm) organic luminescent device of the structure of/LiF (0.5nm)/Al (60nm).
Measurement embodiment: sending out of the preparation embodiment sample of comparative example's sample and organic luminescent device
Optical property:
Under similarity condition, measure sample and the preparation embodiment sample of organic luminescent device of comparative example
Product.Measuring and use KEITHLEY Keithley 235 type source measuring unit, SpectrascanPR650 spectrum is swept
Retouch colorimeter, to evaluate driving voltage, luminosity, luminous efficiency, glow color.Result is listed in table 1
In:
Table 1
According to table 1, above-mentioned sample shows that in 460-480nm wave-length coverage glow color is
Blue.The sample of preparation embodiment of organic luminescent device compares with the sample of comparative example, uses indenes
And the derivant of phenoxazine can have lower driving voltage, more as the organic luminescent device of organic layer
High brightness and higher efficiency.
Obviously, above-described embodiment is only for clearly demonstrating example, and not to embodiment
Limit.For those of ordinary skill in the field, can also be made it on the basis of the above description
The change of its multi-form or variation.Here without also cannot all of embodiment be given exhaustive.And by
What this was extended out obviously changes or changes among still in the protection domain of the invention.
Claims (6)
1. the blue-light semiconductor material containing indeno phenoxazine, it is characterised in that the structure representation of this material
Formula is:
In formula (I), R is phenyl, p-methylphenyl or naphthyl.
The preparation method of the blue-light semiconductor material containing indeno phenoxazine the most according to claim 1, its
It is characterised by, comprises the steps:
Step S1: add 2-bromophenol, 1-iodo-2-nitro acenaphthene and carbonic acid in the reaction vessel after degassing
Potassium, and dissolve with solvent, fully generate 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine after reaction；
Step S2: by above-mentioned 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine and benzoyl oxide, 4-methyl benzoic anhydride or 2-
Naphthalene anhydride reactant generation N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl) Benzoylamide, N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-
P-methylphenyl Methanamide or N-(5 (2-bromobenzene epoxide)-4-acenaphthenyl)-2-naphthalenecarboxamide；
Step S3: continue cyclization reaction and generate (12H-indeno [7,1-AB] phenoxazine-12-base) (phenyl) first
Ketone, (12H-indeno [7,1-AB] phenoxazine-12-base)-(p-methylphenyl) ketone or (12H-indeno [7,1-AB]
Phenoxazine-12-base) blue-light semiconductor material containing indeno phenoxazine of (2-naphthyl) ketone.
The preparation method of the blue-light semiconductor material containing indeno phenoxazine the most according to claim 2, its
Be characterised by, described step S1 particularly as follows:
To degassing after reaction vessel in add 2-bromophenol 1.0mmol, 1-iodo-2-nitro acenaphthene 1.0mmol and
2mmol potassium carbonate, and dissolve with 10mLDMSO, heat 15 hours at 100 DEG C, after being cooled to room temperature, add
Entering a large amount of water, be extracted with ethyl acetate three times, after organic facies washes three times, concentrate drying obtains 5-(2-bromobenzene oxygen
Base)-4-acenaphthenyl amine.
The preparation method of the blue-light semiconductor material containing indeno phenoxazine the most according to claim 2, its
Be characterised by, described step S2 particularly as follows:
By mixed to 5-(2-bromobenzene epoxide)-4-acenaphthenyl amine and the benzoyl oxide of 5mmol, 4-methyl benzoic anhydride or 2-naphthalene acid anhydride
Closing, stirred overnight at room temperature, mixture adds the aqueous solution of sodium carbonate, is extracted with ethyl acetate, and organic facies is used
Anhydrous sodium sulfate is dried, and after concentration, column chromatography obtains N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl) Benzoylamide, N-(5-(2-
Bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl Methanamide or N-(5 (2-bromobenzene epoxide)-4-acenaphthenyl)-2-naphthalenecarboxamide.
The preparation method of the blue-light semiconductor material containing indeno phenoxazine the most according to claim 2, its
Be characterised by, described step S3 particularly as follows:
N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl) Benzoylamide, N-(5-(2-bromobenzene epoxide)-4-acenaphthenyl)-p-methylphenyl
Methanamide or N-(5 (2-bromobenzene epoxide)-4-acenaphthenyl)-2-naphthalenecarboxamide and 2mmol potassium carbonate add reaction
In device, under nitrogen protection, add N, N'-dimethyl-ethylenediamine 0.1mmol and toluene 1mL by syringe,
135 DEG C are stirred 24 hours, and reactant liquor dissolves with dichloromethane after being cooled to room temperature, filters, and concentrates solution, logical
Cross column chromatography and obtain (12H-indeno [7,1-AB] phenoxazine-12-base) (phenyl) ketone, (12H-indeno
[7,1-AB] phenoxazine-12-base)-(p-methylphenyl) ketone or (12H-indeno [7,1-AB] phenoxazine-12-base)
The blue-light semiconductor material containing indeno phenoxazine of (2-naphthyl) ketone.
6. the organic illuminator being made up of the blue-light semiconductor material containing indeno phenoxazine described in claim 1
Part, it includes the first electrode, the second electrode and is placed between described first electrode, described second electrode
One or more organic compound layers, it is characterised in that at least one described organic compound layer comprises described
Blue-light semiconductor material containing indeno phenoxazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410439791.8A CN104262282B (en) | 2014-08-30 | 2014-08-30 | Blue-light semiconductor material containing indeno phenoxazine and preparation method thereof and the organic luminescent device being made up of this material |
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| CN201410439791.8A CN104262282B (en) | 2014-08-30 | 2014-08-30 | Blue-light semiconductor material containing indeno phenoxazine and preparation method thereof and the organic luminescent device being made up of this material |
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| Publication Number | Publication Date |
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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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| 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, method for producing same, photosensor, imaging device, and method for driving same |
| 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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